Fla Van One

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5697 references were found containing "flavanone" as entered. Selected 1 of 2 candidate topics.

using the phrase "flavanone" 2 Research Topic candidates were identified in CAPLUS and MEDLINE.

Research Topic task started on Mon May 19, 2008 at 12:07 PM

Task History

19 May 2008 Page: 1SciFinder Scholar

flavanone

Abstract

Extracting of total flavanone from green pepper and its effects on cavenging of hydroxyl radicals. Fang, Xiao-yan; You, Ting-ting; Lin, Dan-ying; Huang, Suo-yi. Baise Agriculture School in Guangxi, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2008), 25(2), 46-47. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. AN 2008:588629 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

Bibliographic Information Answer 3:

There are several branch points in the flavonoid synthesis pathway starting from chalcone. Among them, the hydroxylation of flavanone is a key step leading to flavonol and anthocyanin. The flavanone 3-β-hydroxylase (GmF3H) gene was cloned from soybean (Glycine max cultivar Sinpaldal) and shown to convert eriodictyol and naringenin into taxifolin and dihydrokaempferol, resp. The major flavonoids in this soybean cultivar were found by LC-MS/MS to be kamepferol O-triglycosides and O-diglycosides. Expression of GmF3H and flavonol synthase (GmFLS) was induced by UV-B (UV-B) irradn. and their expression stimulated accumulation of kaempferol glycones. Thus, GmF3H and GmFLS appear to be key enzymes in the biosynthesis of the UV-protectant, kaempferol.

Abstract

Accumulation of flavonols in response to ultraviolet-B irradiation in soybean is related to induction of flavanone 3-β-hydroxylase and flavonol synthase. Kim, Bong Gyu; Kim, Jeong Ho; Kim, Jiyoung; Lee, Choonghwan; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Molecules and Cells (2008), 25(2), 247-252. Publisher: Korean Society for Molecular and Cellular Biology, CODEN: MOCEEK ISSN: 1016-8478. Journal written in English. AN 2008:594022 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanone 3β-hydroxylases (F3H) are key enzymes in the synthesis of flavonol and anthocyanin. In this study, three F3H cDNAs from Oryza sativa (OsF3H-1 .apprx.3) were cloned by RT-PCR and expressed in E. coli as glutathione S-transferase (GST) fusion proteins. The purified recombinant OsF3Hs used flavanone, naringenin and eriodictyol as substrates. The reaction products with naringen and eriodictyol were detd. by NMR spectroscopy to be dihydrokaempferol and taxifolin, resp. OsF3H-1 had the highest enzymic activity whereas the overall expression of OsF3H-2 was highest in all tissues except seeds. Flavanone 3β-hydroxylase could be a useful target for flavonoid metabolic engineering in rice.

Abstract

Flavanone 3β-hydroxylases from rice: key enzymes for favonol and anthocyanin biosynthesis. Kim, Jeong Ho; Lee, Yoon Jung; Kim, Bong Gyu; Lim, Yoongho; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Molecules and Cells (2008), 25(2), 312-316. Publisher: Korean Society for Molecular and Cellular Biology, CODEN: MOCEEK ISSN: 1016-8478. Journal written in English. AN 2008:594032 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Plant-derived polyphenols attenuate lipopolysaccharide-induced nitric oxide and tumour necrosis factor production in Bibliographic Information Answer 6:

To study the chem. constituents of the aerial part of Dryopteris sublaeta Ching et Hsu. The column of silica gel was employed for the isolation and purifn. of the compds. from Dryopteris sublaeta Ching et Hsu. The structures of the compds. were identified by physiochem. properties and spectral anal. Five compds. were isolated from the ether fraction of 70% acetone-exts., and their structures were identified as (2S)-5, 7-dihydroxy-6, 8-dimethyl flavanone (desmethoxy-matteucinol)(I), (2S)-5, 7-dihydroxy-4'-methoxyl-6, 8-dimethyl flavanone (matteucinol)(II), (2S)-5, 7, 2'-trihydroxy-6, 8-dimethyl flavanone(III), (2S)-5, 7, 4'-trihydroxy-6, 8-dimethyl-3'-methoxyl flavanone(IV), (2S)-5-hydroxy-6, 8-dimethyl-4'-methoxyl-7-O-β-D - glucosyl flavanone(V). All the compds. were isolated from the aerial part of this plant for the first time.

Abstract

Constituents of the aerial part of Dryopteris sublaeta Ching et Hsu. Zheng, Xiaoke; Dong, Sanli; Feng, Weisheng. Basic Medical College, Henan College of Traditional Chinese Medicine, Zhengzhou, Henan, Peop. Rep. China. Proceedings of the China Association for Science and Technology (2008), Volume Date 2007, 4(1), 873-874. Publisher: Science Press, CODEN: PCASCX Journal written in English. AN 2008:539691 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A facile strategy based on click chem. for prepn. of the structurally well-defined native β-cyclodextrin (β-CD) based chiral stationary phase (CSP) was proposed. The β-CD CSP was evaluated by enatiosepn. of benzoin, trans-stilbene oxide, Troger's base, bendroflumethiazide, ketoprofen, chlorthalidone, three flavanone compds. and two β-adrenergic blocking agents under reversed phase high performance liq. chromatog. The chromatog. results demonstrate the chiral sepn. ability of click β-CD CSP and illustrate the usefulness of click chem. in the prepn. of β-CD based CSP.

Abstract

Preparation of novel β-cyclodextrin chiral stationary phase based on click chemistry. Zhang, Yongping; Guo, Zhimou; Ye, Jinxing; Xu, Qing; Liang, Xinmiao; Lei, Aiwen. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, Peop. Rep. China. Journal of Chromatography, A (2008), 1191(1-2), 188-192. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. AN 2008:577844 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of green pepper, avoid wasting and approach the extn. of total flavanone of green pepper and its effects on scavenging of hydroxyl radicals. The flavonoids were extd. by ethanol as the solvent from green pepper with ultrasonic wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of green pepper. The effect of exts. on green pepper scavenging of hydroxyl radicals was studied. By this method getting the d. of the total flavanone of green pepper is C = 0.192 mg/mL and the rate of recovery is 100.9%. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone are all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone of green pepper. Total Flavanone from green pepper have effects on scavenging of hydroxyl radicals.


flavanone

Abstract

Characterization of interactions between polyphenolic compounds and human serum proteins by capillary electrophoresis. Diniz, Andrea; Escuder-Gilabert, Laura; Lopes, Norberto P.; Villanueva-Camanas, Rosa Maria; Sagrado, Salvador; Medina-Hernandez, Maria Jose. Departamento de Ciencias Farmaceuticas, CCS, Universidade Estadual de Londrina, Rod. Celso Garcia Cid, PR 445 km 380, Londrina-PR, Brazil. Analytical and Bioanalytical Chemistry (2008), 391(2), 625-632. Publisher: Springer, CODEN: ABCNBP ISSN: 1618-2642. Journal written in English. AN 2008:524915 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The major flavonoids in rice leaves were analyzed via LC-MS/MS after their total flavonoid exts. were hydrolyzed. The most abundant flavones were apigenin, luteolin, and tricetin. Of these, tricetin was methylated at its 3' and 5'-hydroxyl group to form tricin, which was probably O-glycosylated. Both 3'-O-methylated luteolin and luteolin were found in the C-glycosylated form while apigenin was C-glycosylated. We also cloned and characterized OsFNS, which catalyzes the reaction from flavanone (naringenin) to flavone (apigenin). Anal. of the reaction product with recombinant OsFNS showed that it indeed converts naringenin to apigenin.

Abstract

Analysis of flavonoids and characterization of the OsFNS gene involved in flavone biosynthesis in rice. Kim, Jeong Ho; Cheon, Young Min; Kim, Bong-Gyu; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Journal of Plant Biology (Seoul, Republic of Korea) (2008), 51(2), 97-101. Publisher: Botanical Society of Korea, CODEN: JPBIEZ ISSN: 1226-9239. Journal written in English. AN 2008:530865 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Lipopolysaccharides released during bacterial infections induce the expression of pro-inflammatory cytokines and lead to complications such as neuronal damage in the CNS and septic shock in the periphery. While the initial infection is treated by antibiotics, anti-inflammatory agents would be advantageous add-on medications. In order to identify such compds., we have compared 29 com. available polyphenol-contg. plant exts. and pure compds. for their ability to prevent LPS-induced up-regulation of NO prodn. Among the botanical exts., bearberry and grape seed were the most active prepns., exhibiting IC50 values of around 20 μg/mL. Among the pure compds., IC50 values for apigenin, diosmetin and silybin were 15, 19 and 12 μM, in N-11 murine microglia, and 7, 16 and 25 μM, in RAW 264.7 murine macrophages, resp. In addn., these flavonoids were also able to down-regulate LPS-induced tumor necrosis factor prodn. Structure-activity relationships of the flavonoids demonstrated three distinct principles: (i) flavonoid-aglycons are more potent than the corresponding glycosides, (ii) flavonoids with a 4'-OH substitution in the B-ring are more potent than those with a 3'-OH-4'-methoxy substitution, (iii) flavonoids of the flavone type (with a C2=C3 double bond) are more potent than those of the flavanone type (with a at C2-C3 single bond).

Abstract

murine microglia and macrophages. Shanmugam, Kirubakaran; Holmquist, Lina; Steele, Megan; Stuchbury, Grant; Berbaum, Katrin; Schulz, Oliver; Garcia, Obdulio Benavente; Castillo, Julian; Burnell, Jim; Rivas, Vernon Garcia; Dobson, Geoff; Munch, Gerald. Biochemistry and Molecular Biology, James Cook University, Townsville, Australia. Molecular Nutrition & Food Research (2008), 52(4), 427-438. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: MNFRCV ISSN: 1613-4125. Journal written in English. AN 2008:533397 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Anti-allergic effect of a combination of Citrus unshiu unripe fruits extract and prednisolone on picryl chloride-induced contact dermatitis in mice. Fujita, Tadashi; Shiura, Takehumi; Masuda, Megumi; Tokunaga, Masashi; Kawase, Atsushi; Iwaki, Masahiro; Gato, Takeshi; Fumuro, Masahiko; Sasaki, Katsuaki; Utsunomiya, Naoki; Matsuda, Hideaki. School of Pharmacy, Kinki University, 3-4-1 Kowakae, Higashiosaka, Osaka, Japan. Journal of Natural Medicines (2008), 62(2), 202-206. Publisher:


Et acetate (EtOAc) ext. from the stem bark of Erythrina fusca showed a antimalarial activity against the multi-drug-resistant strain (K1) of Plasmodium falciparum, and six flavonoids, lupinifolin (1), citflavanone (2), erythrisenegalone (3), lonchocarpol A (4), liquiritigenin (5), and 8-prenyldaidzein (6), were isolated from the ext. Diprenylated flavanone 4 showed a notable antimalarial activity (IC50; 1.6 μg/mL); however 1 and 3 did not show the activity, even though these compds. possessed prenylated substitution.

Abstract

In vitro antimalarial activity of prenylated flavonoids from Erythrina fusca. Khaomek, Pranorm; Ichino, Chikara; Ishiyama, Aki; Sekiguchi, Hitomi; Namatame, Miyuki; Ruangrungsi, Nijsiri; Saifah, Ekarin; Kiyohara, Hiroaki; Otoguro, Kazuhiko; Omura, Satoshi; Yamada, Haruki. Faculty of Science, Rangsit University, Pathumthani, Thailand. Journal of Natural Medicines (2008), 62(2), 217-220. Publisher: Springer Japan, CODEN: JNMOBN Journal written in English. AN 2008:506032 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The method for extn. and identification of total flavonoids of longan shell was studied. The flavonoids were extd. by ethanol as the solvent from longan shell with ultrasonic wave. Spectrophotometry was used to det. the flavanone of longan shell. The content of the total flavonoids of longan shell obtained by this method was C=1.204 mg/mL, and the rate of recovery was 98.29%. This text provided the extn. and purifn. methods to get outcome, and the purity of the flavonoids was high. This method was a purely phys. process and had no pollution, and it was an ideal way to ext. the flavonoids of longan shell.

Abstract

The total flavonoids of longan shell extraction and identification by ultrasonic wave. Huang, Suoyi; Liu, Haihua; Li, Haini; Tang, Yulian; Zhang, Jingxuan. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2007), 18(2), 461-462. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. AN 2008:511674 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The interaction of ten natural polyphenolic compds. (chlorogenic acid, apigenin, catechin, epicatechin, flavanone, flavone, quercetin, rutin, vicenin-2 and vitexin) with human serum albumin and mixts. of human serum albumin and α1-acid glycoprotein under near physiol. conditions is studied by capillary electrophoresis-frontal anal. Furthermore, the binding of these polyphenolic compds. to total plasmatic proteins is evaluated using ultrafiltration and capillary electrophoresis. In spite of the relatively small differences in the chem. structures of the compds. studied, large differences were obsd. in their binding behaviors to plasmatic proteins. The hydrophobicity, the presence/absence of some functional groups, steric hindrance and spatial arrangement seem to be key factors in the affinity of natural polyphenols towards plasmatic proteins.


flavanone

JP 2008096317 A 20080424 JP 2006-279333 20061012 Patent No. Kind Date Application No. Date Patent Family Information

Plant variety identification method by composition ratio of flavonoids which plant contains. Nakajima, Noriyuki; Shoji, Kazuaki. (Toyama Prefecture, Japan). Jpn. Kokai Tokkyo Koho (2008), 34pp. CODEN: JKXXAF JP 2008096317 A 20080424 Patent written in Japanese. Application: JP 2006-279333 20061012. Priority: . AN 2008:503213 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. compn. of kava (Piper methysticum) lactones and various phytochems. obtained following the sonication of ground kava roots extd. in the solvents hexane, chloroform, acetone, ethanol, methanol and water, resp., was analyzed. Eighteen kava lactones, cinnamic acid bornyl ester and 5,7-dimethoxy-flavanone, known to be present in kava roots, were identified, and seven compds., including 2,5,8-trimethyl-1-naphthol, 5-methyl-1-phenylhexen-3-yn-5-ol, 8,11-octadecadienoic acid-Me ester, 5,7-(OH)2-4'-one-6,8-dimethylflavanone, pinostrobin chalcone and 7-dimethoxyflavanone-5-hydroxy-4', were identified for the first time. Glutathione (26.3 mg/g) was found in the water ext. Dihydro-5,6-dehydrokavain (DDK) was present at a higher level than methysticin and desmethoxyyagonin, indicating that DDK is also a major constituent of kava roots. Acetone was the most effective solvent in terms of max. yield and types of kava lactones isolated, followed by water and chloroform, whereas hexane, methanol, and ethanol were less effective as solvents. Total phenolic and antioxidant activity varied among the extg. solvents, with acetone and chloroform producing the highest effects, followed by water, while methanol, ethanol and hexane were less effective.

Abstract

Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots. Xuan, Tran Dang; Fukuta, Masakazu; Wei, Ao Chang; Elzaawely, Abdelnaser Abdelghany; Khanh, Tran Dang; Tawata, Shinkichi. Department of Bioscience and Biotechnology, Faculty of Agriculture, University of the Ryukyus, Okinawa, Japan. Journal of Natural Medicines (2008), 62(2), 188-194. Publisher: Springer Japan, CODEN: JNMOBN Journal written in English. AN 2008:506021 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Effect of 50% ethanolic ext. of unripe fruits of Citrus unshiu (CU-ext) on type IV allergic reaction was examd. by inhibitory activity of ear swelling of picryl chloride-induced contact dermatitis (PC-CD) in mice. Oral administration of CU-ext and s.c. administration of prednisolone showed inhibition of ear swelling during both induction and effector phases of PC-CD. The inhibitory activities of combinations of CU-ext (p.o.) and prednisolone (s.c.) during induction phase of PC-CD were more potent than those of CU-ext alone and prednisolone alone. Successive oral administration of hesperidin, a major flavanone glycoside of CU-ext, inhibited ear swelling during induction phase of PC-CD. The inhibitory activities of combinations of hesperidin (p.o.) and prednisolone (s.c.) were more potent than those of hesperidin alone and prednisolone alone. These results indicated that the combinations of prednisolone and CU-ext or hesperidin exerted a synergistic effect.

Abstract

Springer Japan, CODEN: JNMOBN Journal written in English. AN 2008:506026 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

A reversed-phase high-performance liq. chromatog. (HPLC) method was developed for evaluating the chiral discrimination ability of Chiralpak IA chiral stationary phase (CSP) towards flavanone. The effect of the nature and pH buffer as well as nature of alc.

Abstract

High-performance liquid chromatography separation of enantiomers of flavanone and 2'-hydroxychalcone under reversed-phase conditions. Cirilli, Roberto; Ferretti, Rosella; De Santis, Emiliana; Gallinella, Bruno; Zanitti, Leo; La Torre, Francesco. Dipartimento del Farmaco, Istituto Superiore di Sanita, Rome, Italy. Journal of Chromatography, A (2008), 1190(1-2), 95-101. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. AN 2008:495223 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Antibacterial activities of various flavonoids, a group of natural plant substances, have been reported previously, however, there are contradictory data, published by various authors, regarding sensitivity of particular bacterial species to these compds. These problems arose apparently because of using different methods by various researchers. Here we tested sensitivity of several bacterial species (Gram-pos.: Bacillus subtilis, Micrococcus luteus, Sarcina sp. and Staphylococcus aureus; and Gram-neg.: Citrobacter freundii, Escherichia coli, Klebsiella pneumoniae, Proteus vulgaris, Pseudomonas aeruginosa, Salmonella enterica, Serratia marcescens and Vibrio harveyi) to various flavonoids: genistein and daidzein (isoflavones), apigenin (a flavone), naringenin (a flavanone) and kaempferol (a flavonol) by measurement of generation times of bacteria in liq. cultures. The presented results indicate that this simple method is adequate for unambiguous assessment of sensitivity of bacterial strains to flavonoids.

Abstract

Assessment of antibacterial effects of flavonoids by estimation of generation times in liquid bacterial cultures. Ulanowska, Katarzyna; Majchrzyk, Anna; Moskot, Marta; Jakobkiewicz-Banecka, Joanna; Wegrzyn, Grzegorz. Department of Molecular Biology, University of Gdansk, Gdansk, Pol. Biologia (Bratislava, Slovakia) (2007), 62(2), 132-135. Publisher: Slovak Academy of Sciences, CODEN: BLOAAO ISSN: 0006-3088. Journal written in English. AN 2008:497024 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A novel plant variety identification method is provided, which has been developed within a shorter time with less expense than the conventional method. A flavonoid-contg. ext. has been prepd. from an organ tissue (e.g., petal, leaf, fruit, seed, stalk, root) of a plant (e.g., tulip, chrysanthemum, rose, carnation, orchid, petunia, torenia, spinach, lettuce, rice plant, wheat) at various stages, and analyzed in comparison. As a result, it has been found that the kinds of various flavonoids (e.g., anthocyanin, flavonol, flavone, isoflavone, flavanone, flavanol, flavan-3,4-diol, flavan-3-ol, anthocyanidin, auron, chalcone, dihydrochalcone), and their relative amts. stay const. irresp. of a plant tissue and a plant growth step, but, vary depending on the plant variety. Therefore, the relative amts. of flavonoids in a flavonoid-contg. ext. could be used for identifying the plant variety.

Abstract JP 2006-279333 20061012Priority Application


flavanone


Seventeen compds. were isolated from the ext. of whole Rhododendron concinnum Hemsl. plant by petroleum ether and acetic ester and structurally identified by modern spectral technol. (MS, 1HNMR, 13CNMR, DEPT and CD) and chem. methodol. They were (2S)-4',5,7-trihydroxy-flavanone (1), (2R,3R)(+)taxifolin (2), avicularin (3), quercetin-3-O-α-L-rhamnoside (4), hyperoside (5), quercetin (6), 19-kaurene acid (7), isoscopoletin (8), ledol (9), stigmast-4-en-6β-ol-3-one (10), β-amyrin (11), α-amyrin (12), 28-hydroxy-β-amyrin (13), uvaol (14), oleanolic acid (15), β-sitosterol (16) and β-daucosterol (17). All of them were isolated from R. concinnum for the first time, in which (1), (7), (8), (9) and (10) were isolated from Rhododendron genus for the first time.

Abstract

Chemical components of Rhododendron concinnum. Yang, Shuhui; Tian, Xuan. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China. Xibei Zhiwu Xuebao (2007), 27(2), 364-370. Publisher: Kexue Chubanshe, CODEN: XZXUEV ISSN: 1000-4025. Journal written in Chinese. AN 2008:482521 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Four UDP-dependent glucosyltransferase (UGT) genes, UGT706C1, UGT706D1, UGT707A3, and UGT709A4 were cloned from rice, expressed in Escherichia coli, and purified to homogeneity. To find out whether these enzymes could use flavonoids as glucose acceptors, apigenin, daidzein, genistein, kaempferol, luteolin, naringenin, and quercetin were used as potential glucose acceptors. UGT706C1 and UGT707A3 could use kaempferol and quercetin as glucose acceptors and the major glycosylation position was the hydroxyl group of carbon 3 based on the comparison of HPLC retention times, UV spectra, and NMR spectra with those of corresponding authentic flavonoid 3-O-glucosides. UGT709A4 only used the isoflavonoids genistein and daidzein and transferred glucose onto 7-hydroxyl group. In addn., UGT706D1 used a broad range of flavonoids including flavone, flavanone, flavonol, and isoflavone, and produced at least two products with glycosylation at different hydroxyl groups. Based on their substrate preferences and the flavonoids present in rice, the in vivo function of UGT706C1, UGT706D1, and UGT707A3 is most likely the biosynthesis of kaempferol and quercetin glucosides.

Abstract

Four glucosyltransferases from rice: cDNA cloning, expression, and characterization. Ko, Jae Hyung; Kim, Bong Gyu; Kim, Jeong Ho; Kim, Hojung; Lim, Chae Eun; Lim, Jun; Lee, Chan; Lim, Yoongho; Ahn, Joong-Hoon. Division of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Journal of Plant Physiology (2008), 165(4), 435-444. Publisher: Elsevier GmbH, CODEN: JPPHEY ISSN: 0176-1617. Journal written in English. CAN 148:443295 AN 2008:489001 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


modifier on enantioselectivity was investigated. Comparative study of enantiosepn. in reversed-phase and polar org. conditions indicated a significative improvement in resoln. when aq.-based eluents were used. The developed reversed-phase chromatog. method was able to sep. the enantiomers of flavanone from its isomeric form, the 2'-hydroxychalcone. The stereochem. stability of flavanone was studied by classical off-column HPLC kinetic procedures in aq. and non-aq. media. It was clearly demonstrated that the 2'-hydroxychalcone was involved as intermediate in the on-column and off-column enantiomerization process of flavanone.


flavanone

Characterization of Phenolic Compounds in Rooibos Tea. Krafczyk, Nicole; Glomb, Marcus A. Institute of Chemistry Food Chemistry, Martin Luther University Halle-Wittenberg, Halle, Germany. Journal of Agricultural and Food Chemistry (2008), 56(9), 3368-3376. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. AN 2008:451107 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


We evaluated the neurotrophic activity of dietary polyphenols by using primary cultures of fetal rat hippocampal neurons in a serum-free medium. Among the tested compds., chlorogenic acid and its metabolite, m-coumaric acid, together with catechins and flavanone, were found to promote neuronal differentiation comparable to the phytochem., honokiol, which has been reported to show potent neurotrophic activity. The present findings may contribute to the development of further neurotrophic studies on dietary polyphenols and their metabolites.

Abstract

Chlorogenic acid and its metabolite m-coumaric acid evoke neurite outgrowth in hippocampal neuronal cells. Ito, Hideyuki; Sun, Xiu-Lan; Watanabe, Makiko; Okamoto, Motoi; Hatano, Tsutomu. Department of Pharmacognosy, Pharmaceutical Sciences, Dentistry and Pharmaceutical Sciences, Okayama University Graduate School of Medicine, Tsushima, Okayama, Japan. Bioscience, Biotechnology, and Biochemistry (2008), 72(3), 885-888. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. AN 2008:453077 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Anthocyanins are red, purple, or blue plant water-sol. pigments. In the past two decades, anthocyanins have received extensive studies for their anti-oxidative, anti-inflammatory, anti-cancer, anti-obesity, anti-diabetic, and cardioprotective properties. In the present study, anthocyanin biosynthetic enzymes from different plant species were characterized and employed for pathway construction leading from inexpensive precursors such as flavanones and flavan-3-ols to anthocyanins in Escherichia coli. The recombinant E. coli cells successfully achieved milligram level prodn. of two anthocyanins, pelargonidin 3-O-glucoside (0.98 mg/L) and cyanidin 3-O-gluside (2.07 mg/L) from their resp. flavanone precursors naringenin and eriodictyol. Cyanidin 3-O-glucoside was produced at even higher yields (16.1 mg/L) from its flavan-3-ol, (+)-catechin precursor. Further studies demonstrated that availability of the glucosyl donor, UDP-glucose, was the key metabolic limitation, while product instability at normal pH was also identified as a barrier for prodn. improvement. Therefore, various optimization strategies were employed for enhancing the homogenous synthesis of UDP-glucose in the host cells while at the same time stabilizing the final anthocyanin product. Such optimizations included culture medium pH adjustment, the creation of fusion proteins and the rational manipulation of E. coli metabolic network for improving the intracellular UDP-glucose metabolic pool. As a result, prodn. of pelargonidin 3-O-glucoside at 78.9 mg/L and cyanidin 3-O-glucoside at 70.7 mg/L was achieved from their precursor flavan-3-ols without supplementation with extracellular UDP-glucose. These results demonstrate the efficient prodn. of the core anthocyanins for the first time and open the possibility for their commercialization for pharmaceutical and nutraceutical applications.

Abstract

High-yield anthocyanin biosynthesis in engineered Escherichia coli. Yan, Yajun; Li, Zhen; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, NY, USA. Biotechnology and Bioengineering (2008), 100(1), 126-140. Publisher: John Wiley & Sons, Inc., CODEN: BIBIAU ISSN: 0006-3592. Journal written in English. AN 2008:469973 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The objective was to study the chem. constituents of the whole plant of Sarcandra glabra. The compds. were isolated by various chromatog. techniques and their structures were elucidated by their physicochem. properties and the anal. of their spectral data. Seven compds. were isolated and identified as isofraxidin(1), hemidesmin-1(2), (-)-(7S, 8R)-Dihydro-dehydrodiconiferyl alc.(3), N-trans- feruloyl tyramine(4), methy rosmarinate (5), Et rosmarinate(6), (+)-3, 3', 5, 5', 7-pentahydro flavanone(7). Compds. 2-4, 6, 7 were isolated from S.glabra for the first time.

Abstract

Studies on chemical constituents of sarcandra glabra. Zhu, Liping; Li, Yuan; Yang, Jingzhi; Zuo, Li; Zhang, Dongming. Ministry of Education Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peop. Rep. China. Zhongguo Zhongyao Zazhi (2008), 33(2), 155-157. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese. AN 2008:446437 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Anthocyanins are colorful plant pigments with promising applications as pharmaceuticals and colorants. In order to engineer efficient pigment biosynthesis in Escherichia coli, the activities of various dihydroflavonol 4-reductases (DFRs) were characterized for the three primary dihydroflavonol substrates. The biochem. assays demonstrated variable DFR activities for dihydroflavonol with one B-ring hydroxyl group, the precursor of pelargonidin derivs. In contrast, dihydroflavonols with two and three B-ring hydroxylation were metabolized with comparable efficiency. Furthermore, the catalysis of DFR for the secondary substrates, flavanones, also depended on the no. of B-ring hydroxyl groups. Engineering the expression of the DFR clones together with plant-specific 4-coumaroyl:CoA ligase, chalcone synthase, chalcone isomerase, and flavanone 3-hydroxylase in E. coli resulted in the synthesis of pelargonidin at various levels, from p-coumaric acids. The identification of a robust DFR from this study can also be used for engineering recombinant synthesis of other bioactive flavonoids, such as flavan-3-ols.

Abstract

Characterization of dihydroflavonol 4-reductases for recombinant plant pigment biosynthesis applications. Leonard, Effendi; Yan, Yajun; Chemler, Joseph; Matern, Ulrich; Martens, Stefan; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, the State University of New York at Buffalo, Buffalo, NY, USA. Biocatalysis and Biotransformation (2008), 26(3), 243-251. Publisher: Informa Healthcare, CODEN: BOBOEQ ISSN: 1024-2422. Journal written in English. AN 2008:446667 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Polyphenols present in rooibos, a popular herbal tea from Aspalathus linearis, were isolated in two steps. First, phenolic ingredients were sepd. by multilayer countercurrent chromatog. (MLCCC). Preparative high-performance liq. chromatog. (HPLC) was then applied to obtain pure flavonoids. The purity and identity of isolated compds. was confirmed by different NMR expts., HPLC-diode array detector (DAD), or gas chromatog.-mass spectrometry (GC-MS) anal. This strategy proved to be valid to isolate material in up to gram quantities and to verify known and previously not published polyphenol structures. In addn. the chem. of dihydrochalcones and related intermediates was studied. The dihydrochalcone aspalathin was oxidized to the corresponding flavanone-C-glycosides ((R)/(S)-eriodictyol-6-C-β-D-glucopyranoside and (R)/(S)-eriodictyol-8-C-β-D-glucopyranoside). Flavanone-6-C-β-D-glucopyranosides were further degraded to flavones isoorientin and orientin.

Abstract


flavanone

Abstract

Research progress of the protective effect of flavonoids on experimental liver injury of animals. Guo, Jingjing; Yang, Xiufen. Department of Pharmacology, School of Pharmaceutical Sciences, Guangxi Traditional Chinese Medical University, Nanning, Peop. Rep. China. Zhongguo Yaolixue Tongbao (2008), 24(1), 5-10. Publisher: Anhui Yike Daxue Linchuan Yaoli Yanjiuso, CODEN: ZYTOE8 ISSN: 1001-1978. Journal; General Review written in Chinese. AN 2008:412684 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chloropropyl functionalized mesoporous silicas with various structural phases such as hexagonal p6mm, cubic Ia3d, and cubic Im3m have been synthesized from the co-condensation of sodium metasilicate and 3-chloropropyltrimethoxysilane (CPTS) in a P123 or F127/HCl/H2O system. The mesostructural phase of the mesoporous silicas was closely related with the amt. of CPTS in the initial synthesis gels when P123 was used as the structure directing agent. On the other hand, the amt. of CPTS did not alter the mesostructure of the materials when F127 was used as the structure directing agent. The tetraalkyl quaternary ammonium hydroxide functionalized mesoporous silica catalysts were prepd. from the obtained chloropropyl-functionalized mesoporous silicas. Over these catalysts we conducted Claisen-Schmidt condensation of benzaldehyde and 2'-hydroxyacetophenone and subsequent Michael addn. to give a pharmaceutically important flavanone compd. The catalyst with Ia3d phase showed higher catalytic activity which was supposed due to the favorable diffusion and mass transfer of substrate mols. into the bicontinuous cubic interwoven pore structure than other cubic and hexagonal structures.

Abstract

Base catalysis via amine-functionalized mesoporous silicas with various structural phases. Sujandi; Park, Sang-Eon. Lab. of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Dep't of Chemistry, Inha University, Incheon, S. Korea. Studies in Surface Science and Catalysis (2007), 170B(From Zeolites to Porous MOF Materials), 1446-1453. Publisher: Elsevier B.V., CODEN: SSCTDM ISSN: 0167-2991. Journal written in English. AN 2008:428200 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


As a result of biotransformation of flavanone (1) by the strain Aspergillus niger MB (being the UV mutant) and by the wild strain Penicillium chermesinum 113 the products of hydroxylation at C-6 (2) and C-4' (5) were obtained. Addnl., three dihydrochalcones with hydroxyl groups at C-2' (4), C-2' and C-5' (3) and C-2' and C-4 (6) were formed.

Abstract

Microbial transformations of flavanone by Aspergillus niger and Penicillium chermesinum cultures. Kostrzewa-Suslow, Edyta; Dmochowska-Gladysz, Jadwiga; Bialonska, Agata; Ciunik, Zbigniew. Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, Wroclaw, Pol. Journal of Molecular Catalysis B: Enzymatic (2008), 52-53 34-39. Publisher: Elsevier B.V., CODEN: JMCEF8 ISSN: 1381-1177. Journal written in English. AN 2008:442489 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, MT, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW

WO 2008034718 A1 20080327 WO 2007-EP59240 20070904Patent No. Kind Date Application No. Date Patent Family Information

Process for the preparation of a cosmetic composition from a plant extract comprising polysaccharides. Chevalier, Veronique; Nguyen, Quang Lan. (L'Oreal, Fr.). PCT Int. Appl. (2008), 31pp. CODEN: PIXXD2 WO 2008034718 A1 20080327 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-EP59240 20070904. Priority: FR 2006-53838 20060920; US 2006-848368 20061002. CAN 148:362905 AN 2008:380912 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytochem. studies on the aerial parts of Dracocephalum rupestre led to the isolation of four groups of flavonoidal alkaloids, dracocephins A-D. They were elucidated as conjugates of flavanone with pyrrolidin-2-one on the basis of extensive spectroscopic anal. The two stereogenic centers rendered each group of the dracocephins as two pairs of enantiomers simultaneously. All of the sixteen isomers were sepd. successfully by chiral HPLC and their stereochem. features were detd. by their CD data and single-crystal X-ray diffraction anal. of one stereoisomer. The additive relation of the chiroptical contributions resulting from the two stereogenic centers was generalized. The CD contribution of the chiral carbon in the pyrrolidin-2-one ring was proposed by subtraction of their resp. contributions.

Abstract

Stereochemistry of flavonoidal alkaloids from Dracocephalum rupestre. Ren, Dong-Mei; Guo, Huai-Fang; Yu, Wen-Tao; Wang, Shu-Qi; Ji, Mei; Lou, Hong-Xiang. Department of Natural Products Chemistry, School of Pharmaceutical Sciences, Shandong University, Jinan, Peop. Rep. China. Phytochemistry (Elsevier) (2008), 69(6), 1425-1433. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. AN 2008:404202 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review with 35 refs. on the research progress of the protective effect of flavonoids (such as flavone, flavonol, flavanone, isoflavone, flavanol and so on) on exptl. liver injury of animals which is induced by chems., drugs, immunostimulation, alc. and hepatic ischemia reperfusion in some degree, and the kinds of protection are relevant to the function of flavonoids such as elimination of free radical, resistance of oxidn., resistance of lipid peroxidn., adjustment of immune function and so on.


flavanone

US 2006-848370P P 20061002FR 2006-53840 A 20060920Priority Application FR 2905865 A1 20080321 FR 2006-53840 20060920




Process for the preparation of a cosmetic composition having a lightening effect on the skin. Nguyen, Quang Lan; Chevalier, Veronique. (L'Oreal, Fr.). PCT Int. Appl. (2008), 28pp. CODEN: PIXXD2 WO 2008034700 A1 20080327 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-EP59008 20070829. Priority: FR 2006-53840 20060920; US 2006-848370 20061002. CAN 148:362902 AN 2008:380444 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This invention relates to process for the prepn. of a cosmetic compn. for topical application comprising a stage of percolation of plant exts. followed by the incorporation of this ext. in a concd. prepn. The plant substances comprising polysaccharides are chosen in particular from algae and plants comprising gums or pectin. The invention also relates to the compn. obtained and to its use in the cosmetics field, in particular on the skin. Thus, tea leaves 2 g and Laminaria digitata alga powder 3 g were placed in a capsule and the capsule was placed in a com. expresso machine. The steam produced by the machine subsequently passes through this pulverulent mixt. until an ext. of 59 mL was obtained. The ext. was collected in the following prepn. (O/W emulsion 41 g): PEG 8 isostearate 5.85 g, hydrogenated polyisobutene 12.7 g, cyclic silicone 10 g, disodium stearoylglutamate 0.15 g, and water 12.3 g.

Abstract US 2006-848368P P 20061002FR 2006-53838 A 20060920Priority Application FR 2905863 A1 20080321 FR 2006-53838 20060920


flavanone

OBJECTIVE To study assay method of total content in Potentilla discolor bunge. METHODS With AlCl3-NaNO2-NaOH as chromogenic agent, total flavanone content of Potentilla discolor bunge is detd. by UV spectrophotometry. RESULTS The optimal detective wavelength was 510 nm, and absorbility and mass concn. was satisfactory linear relationship at the mass concn. of rutin was in 20 .apprx. 50mg/L. The regression equation was y = 7.7457x + 0.0009 (r = 0.9996), and the av. recovery rate was 99.52% and

Abstract

Determination of total flavanone content in Potentilla discolor bunge by ultraviolet spectrophotometry. Jin, Quan; Lian, Li-hua; Luo, Hui-shan. Yanbian University College of Pharmacy, Yanji, Jilin, Peop. Rep. China. Yanbian Daxue Yixue Xuebao (2007), 30(4), 262-263. Publisher: Yanbian Daxue, CODEN: YDYXF5 Journal written in Chinese. AN 2008:365575 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This study was aimed to investigate the differential protective effect of dietary flavonoids against oxidative stress induced by proinflammatory stimuli in parenchymal liver cells. Chang Liver cells were incubated with a cytokine mixt. (CM) supplemented with the flavonols quercetin and kaempferol, the flavanone taxifolin and the flavone apigenin (5-50 μM). Concns. of oxidised and reduced glutathione, generation of different ROS/RNS, and expression of antioxidant enzymes were measured. Oxidised glutathione concn. and the oxidised/reduced glutathione ratio were increased by the CM. These effects were significantly prevented by quercetin, kaempferol and taxifolin at all tested concns. Effects of apigenin reached a lesser extent and were not significant at 25 μM. Treatment with quercetin and kaempferol prevented the prodn. of peroxides, superoxide anion and nitric oxide induced by CM. Taxifolin 50 μM and apigenin 25-50 μM caused a significant increase in peroxides and nitric oxide generation. Protein concn. of the different antioxidant enzymes was generally reduced by kaempferol and quercetin in comparison to CM, although quercetin 25 and 50 μM increased Mn SOD protein concn. GPx protein level was significantly increased by apigenin 25 and 50 μM. Changes in mRNA tended to be parallel to those in protein concn. Our study reveals that important differences exist between flavonoids with different structural features in their capacity to abrogate the generation of different ROS/RNS, and suggests that the modulation of antioxidant enzymes by flavonoids may be also important in their antioxidant effects in liver cells.

Abstract

Differential effects of dietary flavonoids on reactive oxygen and nitrogen species generation and changes in antioxidant enzyme expression induced by proinflammatory cytokines in Chang Liver cells. Crespo, Irene; Garcia-Mediavilla, Maria V.; Almar, Mar; Gonzalez, Paquita; Tunon, Maria J.; Sanchez-Campos, Sonia; Gonzalez-Gallego, Javier. Ciberehd and Institute of Biomedicine, University of Leon, Leon, Spain. Food and Chemical Toxicology (2008), 46(5), 1555-1569. Publisher: Elsevier Ltd., CODEN: FCTOD7 ISSN: 0278-6915. Journal written in English. AN 2008:366191 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This invention relates to a process for the prepn. of a compn. for topical application, characterized in that it comprises a stage of percolation of fluid under pressure through at least one plant substance in the solid or pasty form chosen from plant substances comprising coumarin sugar derivs. Plant substances comprising vitamin C can also be combined therewith. The invention also relates to the compn. obtained and to its use in the cosmetics field, in particular for lightening the skin.

Abstract


flavanone

The extraction and identification of total flavonoids from Houttuynia cordata Thunb. by ultrasonic wave. Huang, Suoyi; Wan, Chengjun; Zou, Yongfang; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(11), 2261-2262. Publisher: Shizhen Guoyi Guoyao Bianweihui,


Scavenging activities of seven natural flavonoids from Elsholtzia bodinieri vaniot and Artemisia ordosica kraschen for superoxide anion radicals was studied by single-sweep oscillopolarog. Results showed that the scavenging activities of the flavonoids for O2- were related with the no. of hydroxyl groups in the flavonoids. The more nos. of hydroxyl groups, the more active is the flavonoid. The C2-C3 double bond is also contributed to scavenging O2-. The glucoside of flavanone has reduced scavenging ability because of steric hindrance.

Abstract

Scavenging activities of seven natural flavonoids for superoxide anion radicals. Li, Mingjing; Qing, Weixia; Yang, Yuxia; Zhao, Dongbao; Liu, Xiuhua; Liu, Kuaizhi. College of Chemical and Chemical Engineering, Henan University, Kaifeng, Henan Province, Peop. Rep. China. Huaxue Yanjiu (2006), 17(4), 73-75. Publisher: Huaxue Yanjiu Bianjibu, CODEN: HUYAF4 ISSN: 1008-1011. Journal written in Chinese. CAN 148:347276 AN 2008:295542 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanone glycosides, such as naringin and neohesperidin, are distributed in some Citrus species and have a chiral center in the C-2 position of the flavanone moiety. Naringin and neohesperidin (2S-form) were sepd. from the corresponding C-2 epimers (2R-epi-form) by normal-phase HPLC using a polysaccharide-derived chiral stationary phases (CSPs), CHIRALPAK IB. The analyses of com. samples of naringin revealed that the relative ratios of naringin to the C-2 epimer were 29-89%. In the case of a com. sample of neohesperidin, the relative ratio of the neohesperidin (2S-form) is 84%. The HPLC application to Citrus species used as crude drugs in Japan (Kijitsu, Kikoku and Tohi) showed that the relative ratios of naringin to the C-2 epimer were 75-93% in Kijitsu, 74-79% in Kikoku and 54-64% in Tohi. However, there is a quite small ratio of the (2R)-epi-neohesperidin in Citrus. This result suggested that the avs. of relative ratio of (2S)-naringin in Citrus species reduced according to the maturity of fruits (Kijitsu < Kikoku < Tohi). Since the relative ratios of (2S)-naringin of dry exts. of 5 Kampo formulations (including Kijitsu or Kikoku) decreased to 42-54%, the conversion from naringin to the (2R)-epimer might be enhanced during the decoction process of the formulations.

Abstract

HPLC separation of naringin, neohesperidin and their C-2 epimers in commercial samples and herbal medicines. Uchiyama, Nahoko; Kim, Ik Hwi; Kikura-Hanajiri, Ruri; Kawahara, Nobuo; Konishi, Tenji; Goda, Yukihiro. National Institute of Health Sciences (NIHS), Tokyo, Japan. Journal of Pharmaceutical and Biomedical Analysis (2008), 46(5), 864-869. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. AN 2008:361176 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


RSD was 1.23%. CONCLUSION Using UV spectrophotometry to detect total flavanone content in Potentilla discolor bunge is simple, accurate, and sensitive.


flavanone

We indicated that two P450s (1A9 and 1C1) from Japanese eel (Anguilla japonica) metabolized 7-ethoxycoumarin, 7-ethoxyresorufin, and flavanone. At first, we constructed expression vectors for two types of P 450 (1A9 and 1C1). The reduced CO-difference spectra of Escherichia coli cells transformed with these plasmids showed Soret peaks (450 nm) that were typical of P450s. We

Abstract

Bioconversion by functional P450 1A9 and P450 1C1 of Anguilla japonica. Uno, Tomohide; Okamoto, Sota; Masuda, Satoko; Imaishi, Hiromasa; Nakamura, Masahiko; Kanamaru, Kengo; Yamagata, Hiroshi; El-Kady, Mohamed A. H.; Kaminishi, Yoshio; Itakura, Takao. Laboratory of Biological Chemistry, Department of Biofunctional Chemistry, Faculty of Agriculture, Kobe University, Nada-ku, Kobe, Hyogo, Japan. Comparative Biochemistry and Physiology, Part C: Toxicology & Pharmacology (2008), 147C(3), 278-285. Publisher: Elsevier B.V., CODEN: CBPPFK ISSN: 1532-0456. Journal written in English. CAN 148:420050 AN 2008:283125 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-5-O-β-D-glucopyranoside (1a, 1b), was successfully sepd. by RP-C18 high-performance liq. chromatog. from Balanophora involucrata Hook. f. Some other compds., including a pair of flavanone enantiomers, (2R)- and (2S)-eriodictyol (2a, 2b), and a pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-7-O-β-D-glucopyranoside(3a, 3b), were sepd. by capillary electrophoresis from the same plant. The abs. configurations at C-2 of 1a and 1b were detd. based on their CD spectra. Enzymic hydrolysis of 1a and 1b by β-D-glucosidase afforded (2R)- and (2S)-eriodictyol, resp., which were used as the authentic stds. for co-elution to det. the migration order of the enantiomers, 2a and 2b. We also report the first example of identifying the migration order of 2a and 2b and resolving the sepn. of 3a and 3b by capillary electrophoresis. In addn., 1a was unambiguously characterized for the first time by NMR spectra.

Abstract

Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column. Pan, Jianyu; Zhang, Si; Yan, Liushui; Tai, Jiandong; Xiao, Qiang; Zou, Kun; Zhou, Yuan; Wu, Jun. Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, Peop. Rep. China. Journal of Chromatography, A (2008), 1185(1), 117-129. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. AN 2008:288249 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of Houttuynia cordata Thunb., the extn. identification of total flavonoids of Houttuynia cordata Thunb. was approached. The flavonoids were extd. by ethanol as the solvent from Houttuynia cordata Thunb. with ultrasonic wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of Houttuynia cordata Thunb.. The content of total flavonoids of Houttuynia cordata Thunb. was C=6.48%, and the rate of recovery was 102.4%. The outcome and the purity of the flavanone were all very high. This method was a purely phys. process, and had not any pollution. It was an ideal way to ext. the flavonoids of Houttuynia cordata Thunb..

Abstract

CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. AN 2008:295415 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Phenolic acids, flavonoids, proanthocyanidins, and ellagitannins are polyphenols that may have beneficial effects on human health and provide protection against chronic diseases. To date, limited data exist on quant. intake of polyphenols. The aims of this study were to est. the quant. intakes of polyphenols by using analyzed concns. together with individual food consumption records and to det. major dietary sources. Analyzed concns. of phenolic acids, anthocyanidins, and other flavonoids, proanthocyanidins, and ellagitannins (44 total polyphenol compds.) were entered into the national food compn. database, Fineli. The abs. intakes of the polyphenols and the corresponding food sources were calcd. on the basis of 48-h dietary recalls of 2007 Finnish adults. The mean total intake of polyphenols was 863 ± 415 mg/d. Phenolic acids comprised the dominant group of polyphenols (75% of total intake) followed by

Abstract

Dietary intake and major food sources of polyphenols in Finnish adults. Ovaskainen, Marja-Leena; Torronen, Riitta; Koponen, Jani M.; Sinkko, Harri; Hellstrom, Jarkko; Reinivuo, Heli; Mattila, Pirjo. Department of Health Promotion and Chronic Disease Prevention, Nutrition Unit, National Public Health Institute, Helsinki, Finland. Journal of Nutrition (2008), 138(3), 562-566. Publisher: American Society for Nutrition, CODEN: JONUAI ISSN: 0022-3166. Journal written in English. CAN 148:354858 AN 2008:258364 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Completely deacetylated chitosan was prepd. by the treatment of com. chitosan with 50% aq. NaOH, and then derivatized into several new chitosan phenylcarbamate derivs. having a urea and an imide moiety at the 2-position of the glucosamine ring by the reaction with isocyanate and phthalic anhydride/isocyanate, resp. The chitosan derivs. were coated on macroporous silica gel and evaluated as chiral stationary phases (CSPs) for HPLC. The chiral recognition ability of the chitosan deriv. was improved using the completely deacetylated chitosan. Among the novel chitosan derivs., the 3,5-dimethyl-, 3,5-dichloro-, and 3,4-dichlorophenylcarbamate derivs. possess relatively high chiral resoln. abilities. The CSPs based on the chitosan phenylcarbamate-urea and -imide derivs. were stable in the presence of chloroform and Et acetate as a component of the eluents, and some racemates were better resolved by such eluents. The dichlorophenylcarbamate-imide derivs. showed a high chiral recognition for metal acetylacetonate complexes. The enantiomerization of Al(acac)3 was performed on the chitosan 3,5-dichlorophenylcarbamate-imide deriv. CSP and the resulting chromatogram showed a 26% (+)-isomer enrichment.

Abstract

Enantioseparation using urea- and imide-bearing chitosan phenylcarbamate derivatives as chiral stationary phases for high-performance liquid chromatography. Yamamoto, Chiyo; Fujisawa, Mari; Kamigaito, Masami; Okamoto, Yoshio. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Japan. Chirality (2008), 20(3/4), 288-294. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN 148:486007 AN 2008:269268 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


performed bioconversion expts. in which substrates were added directly to incubation medium. The resulting metabolite(s) were extd. and analyzed by high-performance liq. chromatog. and spectrofluorometer. Incubation of 50 nmol 7-ethoxyresorufin with P 450 1C1 yielded 0.773 nmol of deethylated product, whereas 50 nmol 7-ethoxycoumarin resulted in 4.76 nmol. P 450 1A9 metabolized 50 nmol of 7-ethoxyresorufin and 7-ethoxycoumarin to yield 6.54 and 20.9 nmol of deethylated product, resp. Incubation of 50 nmol flavanone with P 450 1C1 yielded 1.46 nmol and 0.69 nmol of products, whereas 50 nmol flavanone with P 450 1A9 resulted in 1.10 nmol. In this system, 4'-hydroxy flavanones were formed by P 450 1A9 and P 450 1C1. P 450 1A9 also metabolized 50 nmol of 17β-estradiol to yield 4.25 nmol of product. In this system, 2-hydroxy estradiol was formed by P 450 1A9 using 17β-estradiol as a substrate. This study is the first to identify the substrates that P 450 1C1 and 1A9 metabolize.


flavanone

Two new prenylated flavanones, 2S-3'-(2-hydroxy-3-methylbut-3-enyl)licoflavone-4'-Me ether (3)(I) and 2S-3'-(2-hydroxy-3-methylbut-3-enyl)abyssinone II (4)(II), and four known flavanones (1, 2, 5, 6) were isolated from the stem bark of Erythrina addisoniae. The structures were elucidated on the basis of their spectroscopic and physicochem. data. None of the compds. showed antioxidative properties. 4'-Methylabyssinone V (1) and abyssinoflavanone VII (6) showed moderate cytotoxic activity (IC50 = 5 and 3.5 μmol/L, resp.), but apoptosis (caspase-3/7-activation, nuclear fragmentation) was selectively induced by abyssinoflavanone VII (6).

Abstract

Prenylated Flavonoid Derivatives from the Bark of Erythrina addisoniae. Waetjen, W.; Suckow-Schnitker, A. K.; Rohrig, R.; Kulawik, A.; Addae-Kyereme, J.; Wright, C. W.; Passreiter, C. M. Institute of Toxicology, Heinrich-Heine-University, Duesseldorf, Germany. Journal of Natural Products (2008), 71(4), 735-738. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 148:398486 AN 2008:244407 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavones are synthesized from flavanones through the action of flavone synthases (FNSs). There are two FNSs, FNS I and II. FNS I is a sol. dioxygenase present in members of the Apiaceae family and FNS II is a membrane bound cytochrome P 450 enzyme that has been identified in numerous plant species. In this study, we cloned OsFNS I-1 from rice by RT-PCR, expressed it in E. coli, and purified the recombinant protein. By NMR anal., we found that OsFNS I-1 converted the flavanone (2S)-naringenin into the flavone, apigenin. Moreover, we found that the cofactors oxoglutarate, FeSO4, ascorbate and catalase are required for this reaction. OsFNS I-1 encodes a flavone synthase I. This is the first type I FNS I found outside of the Apiaceae family.

Abstract

Characterization of flavone synthase I from rice. Lee, Yoon Jung; Kim, Jeong Ho; Kim, Bong Gyu; Lim, Yoongho; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. BMB Reports (2008), 41(1), 68-71. Publisher: Korean Society for Biochemistry and Molecular Biology, CODEN: BRMEC2 ISSN: 1976-6696. Journal written in English. CAN 148:396763 AN 2008:258307 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


proanthocyanidins (14%) and anthocyanidins and other flavonoids (10%). Due to their high consumption and high concns. of phenolic acids, coffee and cereals were the main contributors to total polyphenol intake. Berries and berry products were the main source for anthocyanidins, ellagitannins, and proanthocyanidins, and fruits were the main source for flavonols, flavones, and flavanones. The results give addnl. support to the recommendations for a varied diet with fruits, berries, cereals, and vegetables.


flavanone

Answer 42:

SCF exts. of Eucalyptus globulus and its column chromatographed fractions were evaluated for antioxidant properties by DPPH, β-carotene-linoleic acid and ESR methods. The SCF ext. of eucalyptus is also found to be suitable as natural food dye in sweet prepns. Toxicol. tests of the crude ext. as well as the fractions show that these exts. are safe as food additives.

Abstract

Antioxidants from supercritical carbon dioxide fluid extracts(SCFE) of bark-peel of eucalyptus globulus. Vankar, Padma Shree; Tiwari, Vandana; Srivastava, Jyoti. Facility for Ecological and Analytical Testing (FEAT), Indian Institute of Technology, Kanpur, India. EJEAFChe, Electronic Journal of Environmental, Agricultural and Food Chemistry (2007), 6(11), 2550-2556. Publisher: EJEAFChe, CODEN: EEJEAT ISSN: 1579-4377. http://ejeafche.uvigo.es/index.php?option=com_docman&task=doc_download&gid=317&Itemid=33 Journal; Online Computer File written in English. AN 2008:242478 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Struthiolanone (1), a flavanone-resveratrol adduct, was isolated from Struthiola argentea. Its structure was detd. by highresoln. mass spectrometry and 1D- and 2D-NMR spectroscopic techniques. The abs. configuration was detd. by comparison of the CD spectrum of biflavonoids. This compd. appears to be the first example of a flavanoid-stilbene adduct.

Abstract

Struthiolanone: a flavanone-resveratrol adduct from Struthiola argentea. Ayers, Sloan; Zink, Deborah L.; Brand, Robert; Pretorius, Seef; Stevenson, Dennis; Singh, Sheo B. Natural Products Chemistry, Merck Research Laboratories, Rahway, NJ, USA. Natural Product Communications (2008), 3(2), 189-192. Publisher: Natural Product Inc., CODEN: NPCACO ISSN: 1934-578X. Journal written in English. AN 2008:242713 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

HO

R

Me Me

CH 2

Me

HO

R1

I R=OH, R 1=OMe

II R=H, R 1=OH


flavanone

Almond (Prunus dulcis [Mill.] D.A. Webb) skins have been proposed as a source of bioactive polyphenols. In this article, the phenolic compn. and antioxidant activity of almond skins obtained from different processes (blanching [freeze-drying], blanching + drying, and roasting) were studied. A total of 31 phenolic compds. corresponding to flavan-3-ols (33% to 56% of the total of phenolic compds. identified), flavonol glycosides (9% to 36%), hydroxybenzoic acids and aldehydes (6% to 26%), flavonol aglycons (1.7% to 18%), flavanone glycosides (3% to 7.7%), flavanone aglycons (0.69% to 5.4%), hydroxycinnamic acids (0.65% to 2.6%), and dihydroflavonol aglycons (0% to 2.8%) were detd. in the skins from 3 different varieties of almonds. The total contents of phenolic compds. identified were significantly (P < 0.05) higher (around 2-fold) in the roasted samples than in the blanched almonds (freeze-dried). Industrial drying (oven drying) of the blanched almond skins produced an increase (< 2-fold) in the contents of phenolic compds., although the results were only statistically significant (P < 0.05) for some samples. The antioxidant activity (ORAC values)

Abstract

Polyphenols and antioxidant properties of almond skins: influence of industrial processing. Garrido, I.; Monagas, M.; Gomez-Cordoves, C.; Bartolome, B. Inst. de Fermentaciones Industriales (CSIC), Madrid, Spain. Journal of Food Science (2008), 73(2), C106-C115. Publisher: Blackwell Publishing, Inc., CODEN: JFDSAZ ISSN: 0022-1147. Journal written in English. AN 2008:238696 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OMe

OHOH

HO

OMeO

OH

OH

I

A novel 2,3-dioxygenated flavanone, erigeroflavanone, as well as eight known flavonoids and two known γ-pyranone derivs., were isolated from an Et acetate-sol. ext. of the flowers of Erigeron annuus. The structure of compd. 1 was elucidated by interpretation of spectroscopic data. All of the isolates were subjected to in vitro bioassays to evaluate their inhibitory activity against advanced glycation end products formation and rat lens aldose reductase.

Abstract

Erigeroflavanone, a Flavanone Derivative from the Flowers of Erigeron annuus with Protein Glycation and Aldose Reductase Inhibitory Activity. Yoo, Nam Hee; Jang, Dae Sik; Yoo, Jeong Lim; Lee, Yun Mi; Kim, Young Sook; Cho, Jung-Hee; Kim, Jin Sook. Department of Herbal Pharmaceutical Development, Korea Institute of Oriental Medicine, Daejeon, S. Korea. Journal of Natural Products (2008), 71(4), 713-715. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 148:398484 AN 2008:239739 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

Bibliographic Information


flavanone

Tomato (Solanum lycopersicum) is one of a group of plants that accumulate chalcones and flavanones. However, the mol. diversity of chalcones, flavanones, and their conjugate metabolites has not been investigated intensively. Here, we report the profiling of chalcones and flavanones in fruits of the dwarf tomato cultivar Micro-Tom using liq. chromatog. Fourier transform ion cyclotron resonance mass spectrometry (LC-FTICR-MS). We identified eriodictyol chalcone and eriodictyol aglycons, along with naringenin chalcone and naringenin aglycons. To our knowledge, this is the first report that demonstrates the presence of eriodictyol chalcone and eriodictyol in tomato. We detected 26 conjugate metabolites of chalcones and flavanones. Chem. information obtained simultaneously by LC-FTICR-MS, including m/z values, MS/MS spectra, UV absorption spectra, and retention times, facilitated the elucidation of mol. formulas and conjugate structures of the metabolites. Eriodictyol chalcone and eriodictyol conjugates had the same modification patterns seen in naringenin chalcone and naringenin conjugates. Chalcones and flavanones were much more abundant in tomato fruit peel than flesh. Accumulation profiles during ripening were classified into three groups. The first group included metabolites that showed the highest accumulation levels at the breaker stage, and then decreased during ripening. The second group included metabolites that accumulated to the highest levels at the turning stage, and then decreased at the red stage. The third group

Abstract

Metabolite profiling of chalcones and flavanones in tomato fruit. Iijima, Yoko; Suda, Kunihiro; Suzuki, Tatsuya; Aoki, Koh; Shibata, Daisuke. Kazusa DNA Research Institute, Kisarazu, Japan. Journal of the Japanese Society for Horticultural Science (2008), 77(1), 94-102. Publisher: Japanese Society for Horticultural Science, CODEN: EGKZA9 ISSN: 1882-3351. Journal written in English. CAN 148:327000 AN 2008:225782 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chem. investigation of the methanol ext. of the viscous secretion on the surface of immature fruits of Paulownia tomentosa furnished nine geranylated flavanones, 6-geranyl-5,7-dihydroxy-3',4'-dimethoxyflavanone (1), 6-geranyl-3',5,7-trihydroxy-4'-methoxyflavanone (2), 6-geranyl-4',5,7-trihydroxy-3',5'-dimethoxyflavanone (3), 6-geranyl-4',5,5',7-tetrahydroxy-3'-methoxyflavanone (4), 6-geranyl-3,3',5,7-tetrahydroxy-4'-methoxyflavanone (5), 4',5,5',7-tetrahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]-3'-methoxyflavanone (6), 3,3',4',5,7-pentahydroxy-6-[6-hydroxy-3,7-dimethyl-2(E),7-octadienyl]flavanone (7), 3,3',4',5,7-pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]flavanone (8), and 3,4',5,5',7-pentahydroxy-3'-methoxy-6-(3-methyl-2-butenyl)flavanone (9), along with six known geranylated flavanones. Among these, compds. 4, 6-9 and the known 6-geranyl-3',4',5,7-tetraahydroxyflavanone (diplacone), 6-geranyl-3,3',4',5,7-pentahydroxyflavanone (diplacol) and 3',4',5,7-pentahydroxy-6-[7-hydroxy-3,7-dimethyl-2(E)-octenyl]flavanone showed potent radical scavenging effects towards DPPH radicals.

Abstract

Geranylated flavanones from the secretion on the surface of the immature fruits of Paulownia tomentosa. Asai, Teigo; Hara, Noriyuki; Kobayashi, Sawa; Kohshima, Shiro; Fujimoto, Yoshinori. Department of Chemistry and Materials Science, Graduate School of Science and Engineering, Tokyo Institute of Technology, Meguro, Tokyo, Japan. Phytochemistry (Elsevier) (2008), 69(5), 1234-1241. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 148:351349 AN 2008:236100 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


was higher for the roasted samples (0.803 to 1.08 mmol Trolox/g), followed by the samples subjected to blanching + drying (0.398 to 0.575 mmol Trolox/g) and then the blanched (freeze-dried) samples (0.331 to 0.451 mmol Trolox/g). Roasting is the most suitable type of industrial processing of almonds to obtain almond skin exts. with the greatest antioxidant capacity.


flavanone

Polynucleotides and polypeptides to produce transgenic plants with enhanced agronomic traits. Abad, Mark; Adams, Tom R.; Alvarez, Julie; Anuradha, Mahindra; Augustine, Alice Clara; Badami, Pranesh; Bell, Erin; Bennett, Kristen; Bensen, Robert; Castiglioni, Paolo; Cerny, R. Eric; Chen, Xianfeng; Chittoor, Jaishree; Deeba, Farah; Deikman, Jill; Deng, Molian; Duff, Stephen; Fabbri, Bradon; Fenner, Jason; Fernandes, Mary; Gabbert, Karen; Galligan, Megan; Goldman, Barry; Hawkins, Debbie; Heard, Jacqueline; Karunanandaa, Bala; Ke, Dangyang; Ledeaux, John; Lee, Gary; Madappa, Savitha; Nelson, Donald; Patty, Obed; Qi, Qungang; Rajani, M. S.; Ramachandra, Dhanalakshmi; Ramamohan, G.; Ruff, Thomas; Sanders, Rick; Sangeetha, S.; Savage, Thomas J.; Savidge, Beth; Shobha, Char; Sudarshana, Padmini; Suma, S. Navarathna; Sun, Jindong; Thompson, Rebecca; Val, Dale; Venkatachalayya, Srikanth; Venkatesh, T.; Vidya, Kr; Wu, Jingrui; Xie, Zhidong; Xu, Nanfei; Zheng, Wei. (Monsanto Technology, LLC, USA). PCT Int. Appl. (2008), 115pp. CODEN: PIXXD2 WO 2008021543 A2 20080221 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-US18368 20070817. Priority: US 2006-838415 20060817. CAN 148:231469 AN 2008:219158 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The title Exocarpium Citri Grandis ext. is prepd. by extg. effective components from Citrus grandis fruit. The Exocarpium Citri Grandis ext. comprises flavanone, rutin, naringin, nervonic acid, various vegetable amino acids, and trace elements. The Exocarpium Citri Grandis ext. has the advantages of high contents of effective components, no bitter taste, and no color, and can be used for producing health-care food, beautification product, and medicine.

Abstract CN 2007-10053279 20070913Priority Application CN 101124986 A 20080220 CN 2007-10053279 20070913 Patent No. Kind Date Application No. Date Patent Family Information

Preparation and application of Exocarpium Citri Grandis extract. Lin, Renhe; Liu, Deqin. (Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2008), 6pp. CODEN: CNXXEV CN 101124986 A 20080220 Patent written in Chinese. Application: CN 1005-3279 20070913. Priority: . CAN 148:307070 AN 2008:221646 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This result demonstrated that chalcones and flavanones undergo sequential modification as ripening progresses.

included metabolites that accumulated gradually during ripening, and showed the highest accumulation levels at the red stage. These accumulation profiles were mapped onto a putative modification pathway deduced from conjugate structures. Mapping revealed that the conjugate metabolites upstream of this pathway accumulated earlier, and those downstream accumulated later during ripening.


flavanone

Our recent study [S. Kobayashi, S. Tanabe, M. Sugiyama, Y. Konishi, Transepithelial transport of hesperetin and hesperidin in intestinal Caco-2 cell monolayers, Biochim. Biophys. Acta, 1778 (2008) 33-41] shows that the mechanism of absorption of hesperetin involves both proton-coupled active transport and transcellular passive diffusion. Here, as well as analyzing the cell permeability of hesperetin, we also study the transport of other flavanones, naringenin and eriodictyol, using Caco-2 cell monolayers. Similar to hesperetin mentioned, naringenin and eriodictyol showed proton-coupled polarized transport in apical-to-basolateral direction in non-saturable manner, const. permeation in the apical-to-basolateral direction (Jap → bl) irresp. of the transepithelial elec. resistance (TER), and preferable distribution into the basolateral side after apical loading in the presence of a proton gradient. Furthermore, the proton-coupled Jap → bl of hesperetin, naringenin and eriodictyol, were inhibited by substrates of the monocarboxylic acid transporter (MCT), such as benzoic acid, but not by ferulic acid. In contrast, both benzoic and ferulic acids have no stimulatory effect on Jap →

Abstract

Transepithelial transport of flavanone in intestinal Caco-2 cell monolayers. Kobayashi, Shoko; Konishi, Yutaka. Department of Food and Life-Science, Takasaki University of Health and Welfare, 37-1, Nakaorui, Takasaki, Gumma, Japan. Biochemical and Biophysical Research Communications (2008), 368(1), 23-29. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 148:369236 AN 2008:205370 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This invention provides transgenic plant cells with recombinant DNA for expression of proteins that are useful for imparting enhanced agronomic trait(s) to transgenic crop plants. This invention also provides transgenic plants and progeny seed comprising the transgenic plant cells where the plants are selected for having an enhanced trait selected from the group of traits consisting of enhanced water use efficiency, enhanced cold tolerance, increased yield, enhanced nitrogen use efficiency, enhanced seed protein, and enhanced seed oil. Three hundred fifty-eight polynucleotides and their encoded protein sequences are provided from corn, soybean cotton, canola, alfalfa, rice, and wheat. An addnl. 28,615 homolog sequences are identified by screening public and proprietary databases. Also disclosed are methods for manufg. transgenic seed and plants with enhanced traits.

Abstract US 2006-816086P P 20060623US 2006-838415P P 20060817Priority Application US 20080000405 A1 20080103 US 2007-765562 20070620



WO 2008021543 A2 20080221 WO 2007-US18368 20070817Patent No. Kind Date Application No. Date Patent Family Information


flavanone

Answer 51:

A combination of sample prepn. (ultrafiltration) and anal. techniques is proposed for the characterization of complex phenolic mixts. such as exts. from almond (Prunus dulcis (Mill.) D.A. Webb) skins. LC/ESI-MS anal. of the permeates obtained after ultrafiltration on semipermeable membranes (low mol.-mass phenolic fractions) allowed the identification of several benzoic acids and aldehydes, flavan-3-ol monomers and oligomers, and flavonol and flavanone glycosides in almond skins. MALDI-TOF and ESI-MS/MS anal. of the diafiltered concs. (high mol.-mass phenolic fractions) demonstrated the presence of proanthocyanidin oligomers up to decamers, composed of (epi)afzelechin, (epi)catechin and (epi)gallocatechin units linked by C-C bonds (type B) and by both C-C and C-O bonds (type A). This anal. protocol can be of utility in the study of low and high mol.-mass phenolic compds. in natural products.

Abstract

Ultrafiltration as alternative purification procedure for the characterization of low and high molecular-mass phenolics from almond skins. Prodanov, Marin; Garrido, Ignacio; Vacas, Visitacion; Lebron-Aguilar, Rosa; Duenas, Montserrat; Gomez-Cordoves, Carmen; Bartolome, Begona. Departamento de Agroalimentacion, IMIDRA, Madrid, Alcala de Henares, Spain. Analytica Chimica Acta (2008), 609(2), 241-251. Publisher: Elsevier B.V., CODEN: ACACAM ISSN: 0003-2670. Journal written in English. CAN 148:425231 AN 2008:198764 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Microglia are innate immune cells in the central nervous system. Activation of microglia plays an important role in the processes of several neurodegenerative diseases including Alzheimer's disease, Parkinson's disease, and HIV dementia. Activated microglia can produce various proinflammatory cytokines and nitric oxide (NO), which may exert neurotoxic effects. Inhibition of microglia activation may alleviate neurodegeneration under these conditions. To search for the novel therapeutic agents against neuroinflammatory diseases, we have screened a series of flavonoid compds. using a cell-based assay. Our studies showed that fisetin markedly suppressed the prodn. of tumor necrosis factor (TNF)-α, NO, and prostaglandin (PG) E2 in lipopolysaccharide (LPS)-stimulated BV-2 microglia cells or primary microglia cultures. Fisetin also inhibited the gene expression of TNF-α, interleukin (IL)-1β, cyclooxygenase (COX-2) and inducible nitric oxide synthase (iNOS) at both mRNA and protein levels. Fisetin significantly suppressed IκB degrdn., nuclear translocation of NF-κB, and phosphorylation of p38 mitogen-activated protein kinase (MAPKs) in the LPS-stimulated BV-2 microglia cells. In addn., fisetin reduced cytotoxicity of LPS-stimulated microglia toward B35 neuroblastoma cells in a co-culture system. These results indicate that fisetin has a strong anti-inflammatory activity in brain microglia, and could be a potential therapeutic agent for the treatment of neuroinflammatory diseases.

Abstract

Suppressive effects of flavonoid fisetin on lipopolysaccharide-induced microglial activation and neurotoxicity. Zheng, Long Tai; Ock, Jiyeon; Kwon, Byoung-Mog; Suk, Kyoungho. Department of Pharmacology, School of Medicine, Brain Science and Engineering Institute, CMRI, Kyungpook National University, Taegu, S. Korea. International Immunopharmacology (2008), 8(3), 484-494. Publisher: Elsevier B.V., CODEN: IINMBA ISSN: 1567-5769. Journal written in English. CAN 148:322913 AN 2008:205220 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


bl of each flavanone by trans-stimulation anal. These results indicates that proton-driven active transport is commonly participated in the absorption of flavanone in general, and that its transport is presumed to be unique other than MCT-mediated transport for absorption of phenolic acids (PAs), sodium-dependent MCT (SMCT) nor anion exchanger-mediated transport.


flavanone

written in English CAN 148:307212 AN 2008:178004 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))

Short and mid-term bioavailability of flavanones from oranges in humans. De Pascual-Teresa, S.; Sanchez-Moreno, C.; Granado, F.; Olmedilla, B.; De Ancos, B.; Cano, M. P. Instituto del Frio, CSIC, Madrid, Spain. Current Topics in Nutraceutical Research (2007), 5(2/3), 129-134. Publisher: New Century Health Publishers, LLC, CODEN: CTNRC3 ISSN: 1540-7535. Journal


Some natural compds. such as flavonoids are known to possess a moderate inhibitory activity against aromatase, this enzyme being an interesting target for hormone-dependent breast cancer treatment. It has been demonstrated that the modulation of flavonoid skeleton could increase anti-aromatase effect. Therefore, new 7,8-benzoflavanones were synthesized and tested for their activity toward aromatase inhibition. It was obsd. that the introduction of a benzo ring at position C-7 and C-8 on flavanone skeleton led to new potent aromatase inhibitors, the resulting 7,8-benzoflavanones being until nine times more potent than aminogluthetimide (the first aromatase inhibitor used clin.).

Abstract

New 7,8-benzoflavanones as potent aromatase inhibitors: Synthesis and biological evaluation. Yahiaoui, Samir; Fagnere, Catherine; Pouget, Christelle; Buxeraud, Jacques; Chulia, Albert-Jose. Faculte de Pharmacie, UPRES EA 4021 "Biomolecules et Therapies anti-tumorales", Limoges, Fr. Bioorganic & Medicinal Chemistry (2008), 16(3), 1474-1480. Publisher: Elsevier Ltd., CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 148:440250 AN 2008:181307 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In inflammation, bacterial products and proinflammatory cytokines induce the formation of large amts. of nitric oxide (NO) by inducible nitric oxide synthase (iNOS), and compds. that inhibit NO prodn. have anti-inflammatory effects. In the present study, we systematically investigated the effects of 36 naturally occurring flavonoids and related compds. on NO prodn. in macrophages exposed to an inflammatory stimulus (lipopolysaccharide, LPS), and evaluated the mechanisms of action of the effective compds. Flavone, the isoflavones daidzein and genistein, the flavonols isorhamnetin, kaempferol and quercetin, the flavanone naringenin, and the anthocyanin pelargonidin inhibited iNOS protein and mRNA expression and also NO prodn. in a dose-dependent manner. All eight active compds. inhibited the activation of nuclear factor-κB (NF-κB), which is a significant transcription factor for iNOS. Genistein, kaempferol, quercetin, and daidzein also inhibited the activation of the signal transducer and activator of transcription 1 (STAT-1), another important transcription factor for iNOS. The present study characterises the effects and mechanisms of naturally occurring phenolic compds. on iNOS expression and NO prodn. in activated macrophages. The results partially explain the pharmacol. efficacy of flavonoids as anti-inflammatory compds.

Abstract

Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and Nf-κB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only Nf-κB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. Hamalainen, Mari; Nieminen, Riina; Vuorela, Pia; Heinonen, Marina; Moilanen, Eeva. The Immunopharmacology Research Group Medical School and Tampere University Hospital, Research Unit, University of Tampere, Tampere, Finland. Mediators of Inflammation (2007), No pp. given. Publisher: Hindawi Publishing Corp., CODEN: MNFLEF ISSN: 0962-9351. http://www.hindawi.com/GetArticle.aspx?doi=10.1155/2007/45673 Journal; Online Computer File written in English. AN 2008:194620 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


Naringin was recovered from the effluent from the industrial processing of pomelo peel using extn. by acid, permeation through a membrane, and chromatog. with a macroporous resin. The adsorption characteristics on the resin of the soln. permeated through the membrane were found by HPLC to be identical to those of a direct alc. ext. of the effluent. Permeation of the soln. through the membrane, however, allowed the AB-8 macroporous resin to be reused at least 6 times without loss of performance. Usage of the resin in the treatment of the effluent is therefore viable in an industrial plant.

Abstract

Macroporous resin adsorption of the flavanone from the effluent in pomelo peel processing. Li, Wei; Zhong, ShiAn; Qiao, Rong; Yuan, ZhouLv; Du, JianPing. Department of Chemistry and Chemical Engineering, Central South University, Changsha Hunan, Peop. Rep. China. Beijing Huagong Daxue Xuebao, Ziran Kexueban (2007), 34(Suppl. 2), 28-31. Publisher: Beijing Huagong Daxue Xuebao, Ziran Kexueban Bianji Weiyuanhui, CODEN: BHDXAA ISSN: 1671-4628. Journal written in Chinese. AN 2008:169160 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present paper deals with the isolation Characterization of a new compd. along with Genkwanin and Kaempferol from the sapwood and anti-ematic activity detn. of 1. From the methanolic ext., genkwanin, kampferol, naringenin and a new derivs. 1 were isolated. The structure of the known compds. were detd. by spectroscopic methods and by direct comparision (m.m.p., co-TLC, Superimposible IR) with authentic samples. The new compd. 1 was purified by acetylated and characterized with the help of NMR and MS datas.

Abstract

New anti-emetic flavanone glycoside from cotoneaster affinis. Jangwan, J. S.; Tiwari, M. P. Department of Chemistry, H.N.B.Garhwal University, Tehri, India. Natural Products (2007), 3(3), 187-189. Publisher: Trade Science Inc., CODEN: NPAREX Journal written in English. AN 2008:169269 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanones are a group of flavonoids characteristic of citrus fruits that have been assocd. with hypocholesterolemic and antioxidative effects. Flavanones from oranges, mainly hesperetin and naringenin, have also been proved to be effective in the inhibition of chem. induced carcinogenesis in animal models. Although there are some studies regarding the bioavailability of flavanones from orange juice or pure compds., the levels of hesperetin and naringenin that may be reached in plasma after the consumption of oranges in a normal diet in humans is largely unknown. The purpose of this study was to investigate the effects of single and repeated intakes of a normal amt. of orange flavanones on hesperidin and naringin plasma concns. and antioxidant activity in humans. After ingestion of 400 g of minimally processed orange fruit the levels of plasma hesperetin increased gradually throughout the study period. The max. level of hesperetin reached in plasma was 148 nmol/L, whereas for naringenin the max. level was only 15 nmol/L. Plasma FRAP decreased slightly during the study, however this decrease was not significant. In the multiple-dose-response study the results showed a significant increase over the baseline levels of hesperetin in plasma after 7 and 14 days of daily ingestion of 200 g orange, thus indicating that the effect obtained after a single-dose ingestion is not predictive of the effect after a multiple-dose regimen.

Abstract


flavanone

Two new prenylated dihydroflavanoids have been isolated from the medicinal plant of Dolichos tenuicaulis (Baker) Craib. Their structures were elucidated as (2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethylpyrano)-3',4'-(2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (1) and

Abstract

Two new bioactive prenylated dihydroflavanoids from the medicinal plant Dolichos tenuicaulis (Baker) Craib. Peng, Jin-Yong; Dong, Fu-Qiu; Liu, Ke-Xin; Han, Xu; Xu, You-Wei; Qi, Yan; Xu, Qi-Wei; Xu, Li-Na. School of Pharmacy, Dalian Medical University, Dalian, Peop. Rep. China. Journal of Asian Natural Products Research (2008), 10(2), 169-175. Publisher: Taylor & Francis Ltd., CODEN: JANRFI ISSN: 1028-6020. Journal written in English. AN 2008:148330 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


[Objective] The objective of this study is to isolate and clone the genes of flavonoid biosynthesis in Brassica juncea. [Method] Homol.-based cloning strategy was used in this study. The primers were designed according to the sequences of homologous genes of the model plant Arabidopsis thaliana. The gene fragments were sequenced, and analyzed by BLAST. [Result] Seventeen gene copies were obtained by using 13 pairs of specific primers. These copies were shown to be homologous to 13 known Arabidopsis thaliana functional genes. The gene CHS (chalcone synthase) has three copies, while the genes PAP (prodn. of anthocyanin pigment) and CHI (chalcone isomerase) each has two copies. No data was found in GenBank about the DNA binding/transcription factor genes (TT2, TT8, TTG2, PAP) and flavanone 3-hydroxylase (TT6) gene of Brassica through BLAST anal. [Conclusion] The cloned copies of genes for flavonoid biosynthesis will provide further information on genetic regulation of seed coat color formation in Brassica juncea.

Abstract

Cloning and sequence analysis of flavonoid biosynthesis genes in Brassica juncea. Yan, Ming-li; Liu, Zhong-song; Guan, Chun-yun; Chen, She-yuan; Liu, Xian-jun; Yuan, Mou-zhi. Rapeseed Research Institute, Hunan Agricultural University, Changsha, Peop. Rep. China. Zhongguo Nongye Kexue (Beijing, China) (2007), 40(12), 2688-2695. Publisher: Zhongguo Nongye Kexue Bianjibu, CODEN: CKNYAR ISSN: 0578-1752. Journal written in Chinese. AN 2008:163113 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new 2',6'-dimethoxy-4',5'-(2'',2''-dimethyl)-pyranochalcone (1) and three known flavanones, namely 5-hydroxy-7-methoxy-8-(3,3-dimethylallyl)-flavanone (Me glabranin) (2), 5,7-dimethoxy-8-(3,3-dimethylallyl)-flavanone (candinone) (3) and 5-O-Me obovatin (pongachin) (4), have been isolated from the chloroform ext. of the roots of Tephrosia pulcherrima. The flavonoids were fully characterized by detailed 1D- and 2D-NMR spectroscopic investigations. The pyranochalcone 1 showed significant antimicrobial activity when tested against a series of microorganisms.

Abstract

A pyranochalcone and prenylflavanones from Tephrosia pulcherrima (Baker) Drumm. Ganapaty, Seru; Srilakshmi, Guttula V. K.; Pannakal, Steve T.; Laatsch, Hartmut. Pharmacognosy and Phytochemistry Division, College of Pharmaceutical Sciences, Andhra University, Visakhapatnam, India. Natural Product Communications (2008), 3(1), 49-52. Publisher: Natural Product Inc., CODEN: NPCACO ISSN: 1934-578X. Journal written in English. CAN 148:466904 AN 2008:164991 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Some dried citrus peels, more familiar as chenpi in China, have been widely used in traditional Chinese medicines from ancient times. This paper reports the efficiency of infusion cooking on extg. minerals and phenolic compds. (flavanone glycosides [FGs], polymethoxylated flavones [PMFs], and phenolic acids), and also antioxidant activity of hot water ext. of citrus peels. Peels of 2 citrus varieties, namely, Satsuma mandarin (C. unshiu Marc.) and Ponkan (C. poonensis Hort. ex Tanaka), which belong to C. reticulata, were selected. As a result, hot water extn. was efficient in extg. phenolic acids and some minerals. As for citrus flavonoids, narirutin, nobiletin, and tangeretin were easier to ext. than hesperidin. The result of antioxidant capacity assays indicated that for citrus peels, hot water ext. had almost the same capacity as the methanol ext. We suggested that Ponkan was more suitable as the source of chenpi, since its hot water ext. had much higher content of phenolic acids, FGs and PMFs, and higher antioxidant capacity than those of Satsuma mandarin. Generally, to raise the extn. temp. or to prolong the time could not yield higher content of phenolic compds. and stronger antioxidant capacity, though the content of minerals increased to some extent. Furthermore, a

Abstract

Minerals, phenolic compounds, and antioxidant capacity of citrus peel extract by hot water. Xu, G. H.; Chen, J. C.; Liu, D. H.; Zhang, Y. H.; Jiang, P.; Ye, X. Q. Dept. of Food Science and Nutrition, Zhejiang Univ., Hangzhou, Peop. Rep. China. Journal of Food Science (2008), 73(1), C11-C18. Publisher: Blackwell Publishing, Inc., CODEN: JFDSAZ ISSN: 0022-1147. Journal written in English. CAN 148:190787 AN 2008:131463 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The prenylated flavanone 2'-4'-dihidroxy-5'-(1'''-dimethylallyl)-6-prenylpinocembrin) (6PP), isolated from the roots of Dalea elegans, shows antimicrobial activity. The aim of this study was to evaluate mitochondrial toxicity and antioxidant properties of 6PP. Addn. of micromolar concns. of 6PP to rat liver mitochondria, stimulated O2 uptake in state 4 and inhibited it in state 3 when malate-glutamate was the respiratory substrate, and inhibited O2 uptake in state 3 when succinate was the substrate. Highest concn. of 6PP also inhibited O2 uptake in state 4 in the latter case; in both conditions, respiratory control index values were decreased. This flavanone collapsed the mitochondrial membrane potential in a concn.-dependent manner. 6PP also inhibited F0F1-ATPase activity in coupled mitochondria and in submitochondrial particles. In the latter, this compd. also inhibited NADH oxidase and succinate dehydrogenase activities. HEp-2 cells were incubated for 24 h with 6PP in presence or absence of 0.5% albumin. As measured by redn. of the mitochondrial-related probe MTT, in the albumin-free condition, 6PP was cytotoxic in a concn.-dependent manner; on the other hand, albumin decreased 6PP effect. In addn., in rat liver microsomes 6PP: (1) inhibited the enzymic lipid peroxidn., (2) exhibited significant scavenging activity, measured by DPPH redn. assay and (3) demonstrated significant antioxidant activity by decreasing the redn. of Mo(VI) to Mo(V). We suggest that 6PP impairs the hepatic energy metab. by acting as mitochondrial uncoupler and by inhibiting enzymic activities linked to the respiratory chain. 6PP also exerts both antioxidant and antiradical activities. Due to its cytotoxicity, this mol., and its future structure developments, can be considered as a potentially promising therapeutic agent, for instance in cancer chemotherapy.

Abstract

Mitochondrial toxicity and antioxidant activity of a prenylated flavonoid isolated from Dalea elegans. Elingold, Igal; Isollabella, M. Paula; Casanova, Marta B.; Celentano, Ana M.; Perez, Cristina; Cabrera, Jose Luis; Diez, Roberto A.; Dubin, Marta. Facultad de Medicina, Centro de Estudios Farmacologicos y Botanicos (CEFYBO), UBA-CONICET, Buenos Aires, Argent. Chemico-Biological Interactions (2008), 171(3), 294-305. Publisher: Elsevier Ireland Ltd., CODEN: CBINA8 ISSN: 0009-2797. Journal written in English. AN 2008:140188 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (2) on the basis of spectroscopic anal.


flavanone

A guaianolide sesquiterpene, a chromenone, and a flavanone from Ligularia macrophylla. Wang, Qi; Chen, Daofeng. Bibliographic Information Answer 63:

The aim of this study was to look for the chem. constituents from the rhizomes of Dryopteris sublaeta. The fresh plant was extd. twice with boiling water, and the ext. was concd. to small vol. under reduced pressure at 50°C. The concd. material was partitioned with ether, Et acetate and n-butanol. The fraction of Et acetate was repeatedly chromatographed over silica gel and Sephadex LH-20 columns. Structures of pure compds. were established on the basis of their physicochem. and spectral data. Nine compds. were obtained and identified as sublaetentin A (1), sublaetentin B (2), sublaetentin C (3), sublaetentin D (4), matteuorienate A, matteuorienate C (6), arbutin (7), 3-methoxy-4-hydroxyphenyl-1-O-β-D- glucopyranoside (8) and 3, 4-dimethoxyphenyl-1-O-β-D-glucopyranoside (9). Compds. 1-4 are new compds., and the others were isolated from this plant for the 1st time.

Abstract

Flavanone O-glycosides from the rhizomes of Dryopteris sublaeta. Feng, Weisheng; Cao, Xinwei; Kuang, Haixue; Zheng, Xiaoke. Henan College of Traditional Chinese Medicine, Zhengzhou, Peop. Rep. China. Yaoxue Xuebao (2007), 42(8), 867-871. Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in English. AN 2008:120022 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


We previously reported that poncirin, a flavanone glycoside isolated from the EtOAc ext. of the dried immature fruits of Poncirus trifoliata, is an anti-inflammatory compd. that inhibits PGE2 and IL-6 prodn. The present work was undertaken to investigate the mol. actions of poncirin in RAW 264.7 macrophage cell line. Poncirin reduced lipopolysaccharide (LPS)-induced protein levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) and the mRNA expressions of iNOS, COX-2, tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in a concn.-dependent manner, as detd. by Western blotting and RT-PCR, resp. Furthermore, poncirin inhibited the LPS-induced DNA binding activity of nuclear factor-κB (NF-κB). Moreover, this effect was accompanied by a parallel redn. in IκB-α degrdn. and phosphorylation that in by nuclear translocations of p50 and p65 NF-κB subunits. Taken together, our data indicate that anti-inflammatory properties of poncirin might be the result from the inhibition iNOS, COX-2, TNF-α and IL-6 expression via the down-regulation of NF-κB binding activity.

Abstract

Inhibition of LPS-induced iNOS, COX-2 and cytokines expression by poncirin through the NF-κB inactivation in RAW 264.7 macrophage cells. Kim, Jong-Bin; Han, Ah-Reum; Park, Eun-Young; Kim, Ji-Yeon; Cho, Woong; Lee, Jun; Seo, Eun-Kyoung; Lee, Kyung-Tae. Department of Pharmaceutical Biochemistry, College of Pharmacy, Kyung-Hee University, Seoul, S. Korea. Biological & Pharmaceutical Bulletin (2007), 30(12), 2345-2351. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 148:276403 AN 2008:128576 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


2nd-time extn. seemed necessary since considerable minerals and phenolic compds. could be obtained by doing so. Finally, we suggested that 2 times extn. at 100 °C for 30 min was proper to ext. the minerals and phenolic compds. in chenpi.


flavanone

Two prenylated flavanones have been isolated from the hexane ext. of Phyllanthus niruri plant. The structure of these flavanones were established as 8-(3-Methyl-but-2-enyl)-2-Ph chroman-4-one (I) and 2-(4-hydroxyphenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one (II) on the basis of spectral anal. These were evaluated for nematicidal activity against root-knot, Meloidogyne incognita, and reniform,

Abstract

Nematicidal prenylated flavanones from Phyllanthus niruri. Shakil, N. A.; Pankaj; Kumar, J.; Pandey, R. K.; Saxena, D. B. Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi, India. Phytochemistry (Elsevier) (2008), 69(3), 759-764. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 148:303519 AN 2008:109643 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytochem. investigation of the hexane and CH2CI2 exts. of Erythrina stricta roots and E. subumbrans stems led to the isolation of six pterocarpans, one flavanone, one isoflavone, two alkaloids, five triterpenes, six steroids and alkyl trans-ferulates. The structures of all known compds. were detd. on the basis of spectroscopic evidence. Sophoradiol (15), a mixt. of stigmast-4-en-3-one (19) and stigmasta-4,22-dien-3-one (20), lupeol (21), cycloeucalenol (22), a mixt. of 3β-hydroxystigmast-5-en-7-one (23) and 3β-hydroxystigmast-5,22-dien-7-one (24) and melilotigenin C (25) were first isolated from the genus Erythrina. The isolated compds. were evaluated for antiplasmodial activity, antimycobacterial activity and cytotoxicity. Among the tested compds., 5-hydroxysophoranone (8) exhibited the highest antiplasmodial activity against Plasmodium falciparum (IC50 2.5 μg/mL). Compd. 8, erystagallin A (5), erycristagallin (7) and erysubin F (10) showed the same level of antimycobacterial activity against Mycobacterium tuberculosis (MIC 12.5 μg/mL). For cytotoxicity, erybraedin A (2) showed the highest activity against the NCI-H187 and BC cells (IC50 2.1 and 2.9 μg/mL, resp.), whereas 10 exhibited the highest activity against the KB cells (IC50 4.5 μg/mL).

Abstract

Biological activities of the chemical constituents of Erythrina stricta and Erythrina subumbrans. Rukachaisirikul, Thitima; Saekee, Amporn; Tharibun, Chatchana; Watkuolham, Sudarut; Suksamrarn, Apichart. Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, Thailand. Archives of Pharmacal Research (2007), 30(11), 1398-1403. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 148:163654 AN 2008:117697 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Three new compds., (5β,9β)-guaia-6,10(14)-dien-9-ol (=rel-(1R,3aS,5R,8aR)-1,2,3,3a,4,5,6,8a-octahydro-1-methyl-4-methylene-7-(1-methylethyl)azulen-5-ol; 1), 6-acetyl-8-methoxy-2,3-dimethyl-chromen-4-one (=6-acetyl-8-methoxy-2,3-dimethyl-4H-1-benzopyran-4-one; 2), and (2S)-3'-hydroxy-5',7-dimethoxyflavanone (=(2S)-2,3-dihydro-2-(3-hydroxy-5-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one; 3) were isolated from the roots and rhizomes of Ligularia macrophylla, together with seven known compds. Their structures and configurations were elucidated by spectroscopic methods, including 2D-NMR techniques.

Abstract

Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, Peop. Rep. China. Helvetica Chimica Acta (2007), 90(12), 2432-2437. Publisher: Verlag Helvetica Chimica Acta, CODEN: HCACAV ISSN: 0018-019X. Journal written in English. CAN 148:163658 AN 2008:117980 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Natural ingredients used in cosmeceuticals. Dweck, Anthony C. Dweck Data, Salisbury, Wiltshire, UK. Editor(s): Walters, Kenneth A.; Roberts, Michael S. Dermatologic, Cosmeceutic, and Cosmetic Development (2008), 303-323. Publisher: Informa Healthcare, New York, N. Y CODEN: 69KKCH Conference; General Review written in English. AN 2008:107398 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Carcinoma of the stomach is reportedly the second most common cancerous condition affecting the general population. Administration of antioxidants is reported to effectively alleviate the risk of gastric carcinoma. Therefore, we assessed the protective role of naringenin, an antioxidant and naturally occurring citrus flavanone, on gastric carcinogenesis induced by MNNG (200mg/kg body wt.) and S-NaCl (1 mL per rat) in Wistar rats (obtained from the Central Animal House Facility, University of Madras, Taramani Campus, Chennai, India). The animals were divided into 5 groups, and the effects of naringenin on simultaneous and posttreated stages of MNNG were tested. Cancer risk was analyzed along with their antioxidant status. The LPO levels in the exptl. groups were assessed as an index of oxidative milieu. Altered redox status was subsequently investigated by assaying the superoxide and hydroxyl radicals, the enzymic antioxidants (SOD, CAT, GPx), and the nonenzymic antioxidants viz reduced GSH, vitamin C, and vitamin E. In the presence of MNNG, cancer incidence and LPO levels were significantly increased, whereas enzymic (SOD, CAT, and GPx) and nonenzymic antioxidant activities (GSH, Vitamins C, and E) were decreased in the treated rats compared with control rats. Administration of naringenin to gastric carcinoma-induced rats largely up-regulated the redox status to decrease the risk of cancer. We conclude that up-regulation of antioxidants by naringenin treatment might be responsible for the anticancer effect in gastric carcinoma.

Abstract

Naringenin reduces tumor size and weight lost in N-methyl-N'-nitro-N-nitrosoguanidine-induced gastric carcinogenesis in rats. Ekambaram, Ganapathy; Rajendran, Peramaiyan; Magesh, Venkataraman; Sakthisekaran, Dhanapal. Department of Medical Biochemistry, Dr A.L. Mudaliyar Postgraduate Institute of Basic Medical Sciences, University of Madras, Chennai, India. Nutrition Research (New York, NY, United States) (2008), 28(2), 106-112. Publisher: Elsevier Inc., CODEN: NTRSDC ISSN: 0271-5317. Journal written in English. CAN 148:440429 AN 2008:109297 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

MeMe

R

I R=H

II R=OH

Rotylenchulus reniformis, nematodes. Compd. 2 exhibited nematicidal activity at par with the std. carbofuran (LC50 3.3 and 3.1 ppm, resp.) when tested against reniform nematode. The LC50 value against root-knot nematode was found to be 14.5 ppm. Compd. 1 however, showed moderate activity against both the test nematodes.


flavanone


Flavonoids were extd. by ethanol as the solvent from papaya leaves with ultrasonic wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of papaya leaves. The d. of the total flavanone of papaya leaves was C = 0.9880 mg/mL and the rate of recovery was 97.79%. This method was a purely phys. process and had not any pollution. It was an ideal way to ext. the flavanone from papaya leaves.

Abstract

Extraction and identification of total flavanone from papaya leaves by ultrasonic wave. Huang, Suoyi; Liu, Haihua; Li, Haini; Tang, Yulian; Zhang, Jingxuan. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(10), 1863-1864. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:433472 AN 2008:103407 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Molasses of tangerine orange (Citrus unshiu Markovich) is obtained as a waste product in the course of tangerine orange juice prodn. This molasses is expected to be a useful source of org. compds. such as flavonoids and limonoids. To elucidate a use for this molasses waste, we isolated and identified its org. constituents. Two new flavanonol glycosides were isolated from tangerine orange molasses, along with several flavonoids such as hesperidine, narirutin, eriodictyol, 3',4',5,6,7,8-hexamethoxy-3-O-β-D-glucopyranosyloxyflavone, and 3',4',5,6,7,8-hexamethoxy- 3-β-D-[4-O-(3-hydroxy-3-methylglutaloyl)]-glucopyranosyloxyflavone, and limonoids such as limonin, nomilin, and cyclic peptide, citrusin III. The structures of the new flavanonol glycosides were detd. as (2R,3R)-7-O-(6-O-α-L-rahmnopyranosyl-β-D-glucopyranosyl)-aromadendrin and 7-O-(6-O-α- L-rahmnopyranosyl-β-D-glucopyranosyl)-3,3',5,7-tetrahydroxy-4'-methoxyflavanone by means of spectral analyses using 1H-NMR, 13C-NMR, and 2D-NMR. Of these compds., flavanone glycoside, hesperidin and narirutin were isolated as the main constituents. Thus, molasses is a promising source of flavonoid glycosides.

Abstract

Flavonoid glycosides and limonoids from Citrus molasses. Kuroyanagi, Masanori; Ishii, Hiromi; Kawahara, Nobuo; Sugimoto, Hiroyuki; Yamada, Hideo; Okihara, Kiyoshi; Shirota, Osamu. Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, Shobara, Hiroshima, Japan. Journal of Natural Medicines (2008), 62(1), 107-111. Publisher: Springer Japan, CODEN: JNMOBN Journal written in English. CAN 148:444846 AN 2008:104357 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The sources of data for products that may have topical cosmeceutical benefit were presented. The different chem. compds. present in plants were also discussed, specifically fatty acids, flavanoids, chalcones, flavones, flavanone glycoside, aurones, flavonols, isoflavones, phytosterols and related compds. and sugars, polysaccharides, and mucopolysaccharides. Various plants that are considered to be specialist plants because of their unique chem. entities were also conferred.

Abstract


flavanone

The anti-tumor activities of many plant phenolics at high concns. (>100 μmol/L) suggest their potential use as dietary supplements in cancer chemoprevention and cancer chemotherapy. However, it is not clear what impact phenolic compds. have at the physiol.

Abstract

Plant phenolics regulate neoplastic cell growth and survival: a quantitative structure-activity and biochemical analysis. Harris, Cory S.; Mo, Fan; Migahed, Lamiaa; Chepelev, Leonid; Haddad, Pierre S.; Wright, James S.; Willmore, William G.; Arnason, John T.; Bennett, Steffany A. L. Neural Regeneration Laboratory and Ottawa Institute of Systems Biology, Department of Biochemistry, Microbiology, and Immunology, University of Ottawa, Ottawa, ON, Can. Canadian Journal of Physiology and Pharmacology (2007), 85(11), 1124-1138. Publisher: National Research Council of Canada, CODEN: CJPPA3 ISSN: 0008-4212. Journal written in English. CAN 148:321834 AN 2008:88564 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Recently, there is a growing interest about unsatd. lecithin having excellent characteristics of skin affinity and absorbency. Accordingly, this study intended to develop a natural sulfuration material in order to enhance the stability of oxidn. of unsatd. lecithin and substitute existing sulfuration materials which indicate variability and toxicity. As sulfuration components, plenol acid family, 3,5-dihydroxybenzoic acid, and flavanone were analyzed. Total polyphenol content was higher in the root exts. (133.85 mg/g) than in the fruit exts. (53.5 mg/g). Above 100 ppm polyphenol content, the free radical removal efficiency and lipid oxidn. prevention of the root exts. were 20.1 and 19.2% superior compared with BHT resp. Also, the exts. indicated high survival rate of more than 95% below 1250 ppm, showing the stability. For the stability of liposome made from an unsatd. lecithin, the root exts. were superior to the fruit exts. Esp., 15.1 and 13.9% of sulfuration effect and zeta potential were improved with 9.3% reduced particle size compared with BHT as the control group, resp.

Abstract

Antioxidantive effectiveness of Trichosanthes kirilowii maximowicz extracts. Zhoh, Choon Koo; Uhm, Tae Yong; Kim, Joo Chan. Department of Chemical+Environmental Engineering, Soongsil University, Seoul, S. Korea. Kongop Hwahak (2007), 18(6), 625-629. Publisher: Korean Society of Industrial and Engineering Chemistry, CODEN: KOHWE9 ISSN: 1225-0112. Journal written in Korean. AN 2008:98447 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


After supercrit. fluid extn. (SFE), the volatile oil was sepd. by GC-MS and detd. by normalization method. Forty-four components from propoils by SFE were sepd. and identified, representing 93.12% of the total area. The main compds. of volatile oil were 9,12-octadecadienoic acid 23.91%, hexacosane 12.92%, nonacosane 7.44%, hexadecanoic acid 6.65%, tetracosane 5.23%, octadecadienoic acid, Me ester 4.58%, 9-Octadecenoic acid 3.94%, ergostero 3.90%, heneicosane 3.42% etc. Supercrit. extn. was not widely used yet, there would be more and more viewpoints that could justify it, as simple and convenient, high purity, residual solvent content.

Abstract

Supercritical carbon dioxide extraction of essential oil from propolis of Mount Meng and analysis by GC-MS. Li, Yajie; Ling, Jianya; Deng, Yong. School of Life Science, Shandong University, Jinan, Shandong Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(10), 1975-1976. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:433467 AN 2008:103168 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 75:

Diets rich in citrus and citrus-based products have been neg. correlated with the risk of cardiovascular disease, but so far no studies have been conducted to det. whether naringenin and hesperetin, two major flavanones in citrus plants, influence endothelium nitric oxide (NO) prodn. The aim of this study is to clarify estrogenic activities of naringenin and hesperetin and to examine whether they affect endothelial NO prodn. via estrogen receptor (ER) activation. Both naringenin and hesperetin were obsd. to promote growth of MCF-7 cells under greatly reduced estrogen conditions and to suppress estrogen-induced response. Naringenin activated both ERα and ERβ, whereas hesperetin exhibited stronger potential to activate ERα rather than ERβ. Hesperetin, but not naringenin, increased NO releases from human umbilical vein endothelial cells in a dose-dependent manner. Hesperetin-induce responses were suppressed by ICI 182 780 and actinomycin D. Real-time reverse transcription polymerase chain reaction (RT-PCR) and western-blotting anal. revealed that hesperetin up-regulated endothelium nitric oxide synthase (eNOS) expression. These results suggested that hesperetin exerts an antiatherogenic effect, in part, via ER-mediated eNOS expression and subsequent increase of endothelial NO prodn. Distinct effects of naringenin and hesperetin on NO prodn. also imply that ERα might play the major role in estrogen-induced eNOS expression. However, the inefficacy of naringenin on NO prodn. remains to be elaborately studied. Our findings add more proof to the mol. explanations for the health benefits of citrus used to prevent cardiovascular disease, esp. for postmenopausal women.

Abstract

Distinct Effects of Naringenin and Hesperetin on Nitric Oxide Production from Endothelial Cells. Liu, Li; Xu, Dong-mei; Cheng, Yi-yu. College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Peop. Rep. China. Journal of Agricultural and Food Chemistry (2008), 56(3), 824-829. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 148:253808 AN 2008:66722 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


5,7-Dihydroxy-flavanone was synthesized with cinnamic acid from benzaldehyde, whose yield amounted to 91%. Its structure was characterized and confirmed by IR, MS and 1H NMR. Meanwhile, bactericidal tests had been carried out, and the results of preliminary biol. test indicated that the compd. had excellent bactericidal activities against Escherichia coli, Bacillus subtilis, Staphylococcus aureus. The inhibition rate againsted Escherichia coli, Bacillus subtilis amounted to 100% at the dosage of 50 μg/mL.

Abstract

Synthesis and bactericidal activity of 5,7-dihydroxy-flavanone. Li, Jianfen; Chen, Hongmei. Department of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan, Peop. Rep. China. Nongyao (2006), 45(11), 733-734, 736. Publisher: Nongyao Bianjibu, CODEN: NONGFP ISSN: 1006-0413. Journal written in Chinese. AN 2008:80189 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


concns. obtained through consumption of high phenolic diets on neoplastic cells. In the present study, 54 naturally occurring phenolics were evaluated at physiol. relevant concns. for their capacity to alter PC12 cell viability in response to serum deprivation, the chemotherapeutic agent etoposide, and the apoptogen C2-ceramide. Surprisingly, novel mitogenic, cytoprotective, and antiapoptotic activities were detected. Quant. structure-activity relationship modeling indicated that many of these activities could be predicted by compd. lipophilicity, steric bulk, and (or) antioxidant capacity, with the exception of inhibition of ceramide-induced apoptosis. Where quant. structure-activity relationship anal. was insufficient, biochem. assessment demonstrated that the benzoate orsellinic acid blocked downstream caspase-12 activation following ceramide challenge. These findings demonstrate substantive mitogenic, cytoprotective, and antiapoptotic biol. activities of plant phenolics on neoplastic cells at physiol. relevant dietary concns. that should be considered in chemopreventive and chemotherapeutic strategies.


flavanone

Study on extracting processing of the total flavanone of melon by ultrasonic wave. Pang, Hong; Wen, Lue; Wang, Xiao-ping; Li, Lin; Huang, Suo-yi. Department of Chemistry, Guangxi Medicine School, Nanning, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(6), 49-50. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 148:448161 AN 2008:63238 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This study on the flavanone material extn. and purifn. which obtains to the tartary buckwheat liquor distiller's grain, then strengthen 38° & 53° buckwheat liquor, its DPPH free radical clearance percentage and total oxidn. resistance ability enhance sep. 90.35%, 31.69 U/mL and 85.64%, 24.92 U/mL, the effect is extremely remarkable. This strengthening process is good to the liquor feeling in the mouth reveals mellowly. But not to the liquor quality extremely affects.

Abstract

Development of oxidation resisting tartary buckwheat wine. Li, Yunlong; Fang, Shan; Bian, Junsheng; Li, Hongmei; Hu, Junjun; Di, Jianbing; He, Zhiyong; Lin, Rufa. Institute of Comprehensive Utilization of Agricultural Products, Shanxi Academy of Agricultural Science, Taiyuan, Peop. Rep. China. Editor(s): Chai, Yan; Zhang, Zongwen. Advances in Buckwheat Research, Proceedings of the International Symposium on Buckwheat, 10th, Yangling, China, Aug. 14-18, 2007 (2007), 422-426. Publisher: Northwest A&F University Press, Yangling, Peop. Rep. China CODEN: 69KILK Conference written in English. AN 2008:66119 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Total antioxidant capacities and phenolic contents of ethanol exts. of common and tartary buckwheat seeds were examd. Total antioxidant properties of exts. were assessed by FRAP assays, total phenolic contents measured by Folin-Ciocalteu assay, and flavonoids contents measured by NaNO2-Al(NO)3. The result indicated that there were differences in total antioxidant capacities, total phenolic and flavonoids contents of ethanol exts. of seeds for different cultivars. While differences in FRAP value of buckwheat flour for different cultivars and common buckwheat hull for different cultivars was not remarkable. The total phenolic content of tartary buckwheat flour was approx. two times higher than that of common buckwheat flour. In contrast, total phenolic content of common buckwheat hull was higher than that of tartary buckwheat hull. Total flavonoids content of tartary buckwheat flour was higher than that of common buckwheat flour but the difference was limited. Total flavonoids content of common buckwheat hull was higher than that of tartary buckwheat hull and the difference was significant. All exts. exhibited good antioxidant activity. Compared with common buckwheat, tartary buckwheat exhibited stronger antioxidant activity.

Abstract

Antioxidant activity of seed ethanol extracts of different buckwheat cultivars. He, Yongyan; Feng, Baili; Gao, Jinfeng; Pang, Ming; Chai, Yan. College of Agronomy, Northwest A+F University, Yangling, Shaanxi, Peop. Rep. China. Editor(s): Chai, Yan; Zhang, Zongwen. Advances in Buckwheat Research, Proceedings of the International Symposium on Buckwheat, 10th, Yangling, China, Aug. 14-18, 2007 (2007), 567-575. Publisher: Northwest A&F University Press, Yangling, Peop. Rep. China CODEN: 69KILK Conference written in English. CAN 148:448353 AN 2008:66141 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 80:

Extg. of total flavanone from flocculu's banyan silk was made, the extd. flavone was validated, and UV spectrophotometry was used to det. its content. Mass concn. of total flavone in the detd. sample was 1.151 mg/mL, recovery was 99.36% with high purity and yield. The extd. liq. was detd. to have scavenging on hydroxyl radicals. Scavenging capacity on hydroxyl radicals increased as the extd. liq. increases.

Abstract

Extracting of total flavanone from flocculu's banyan silk and its effects on scavenging of hydroxyl radicals. Huang, Suoyi; Li, Haini; Tang, Yulian; Liu, Haihua. Youjiang Nationality Medical College, Baise, Guangxi Province, Peop. Rep. China. Huagong Shengchan Yu Jishu (2006), 13(4), 16-18. Publisher: Huagong Shengchan Yu Jishu Bianjibu, CODEN: HSYJAC ISSN: 1006-6829. Journal written in Chinese. CAN 148:433433 AN 2008:50244 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The citrus flavanones hesperidin, hesperetin, and neohesperidin are known to exhibit antioxidant activities and could traverse the blood-brain barrier. H2O2 formation induces cellular oxidative stress assocd. with neurodegenerative diseases. In this study, protective effects of pretreatments (6 h) with hesperidin, hesperetin, and neohesperidin (0.8, 4, 20, and 50 μM) on H2O2-induced (400 μM, 16 h) neurotoxicity in PC12 cells were evaluated. The results showed that hesperetin, hesperidin, and neohesperidin, at all test concns., significantly (p < 0.05) inhibited the decrease of cell viability (MTT redn.), prevented membrane damage (LDH release), scavenged ROS formation, increased catalase activity, and attenuated the elevation of intracellular free Ca2+, the decrease of mitochondrial membrane potential (except those of 0.8 μM neohesperidin-treated cells) and the increase of caspase-3 activity in H2O2-induced PC12 cells. Meanwhile, hesperidin and hesperetin attenuated decreases of glutathione peroxidase and glutathione reductase activities and decreased DNA damage in H2O2-induced PC12 cells. These results first demonstrate that the citrus flavanones hesperidin, hesperetin, and neohesperidin, even at physiol. concns., have neuroprotective effects against H2O2-induced cytotoxicity in PC12 cells. These dietary antioxidants are potential candidates for use in the intervention for neurodegenerative diseases.

Abstract

Neuroprotective Effects of the Citrus Flavanones against H2O2-Induced Cytotoxicity in PC12 Cells. Hwang, Sam-Long; Yen, Gow-Chin. Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan. Journal of Agricultural and Food Chemistry (2008), 56(3), 859-864. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 148:135838 AN 2008:57999 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of bitter melon, avoid wasting and approach the extn. of total flavanone of bitter melon. The flavonoids were extd. by ethanol as the solvent from bitter melon with ultrasonic wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of bitter melon. By this method getting the contents of the total flavanone of bitter melon is C = 6.72% and the rate of recovery is 101.0%. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone are all very high. This method is a purely phys. process, and has not any pollution. It is an ideal way to ext. the flavanone of bitter melon.

Abstract


flavanone

High level antioxidant-containing plants expressing a transcription factor involved in flavonoid pathway. Rommens, Caius. (J.R. Simplot Company, USA). PCT Int. Appl. (2008), 67pp. CODEN: PIXXD2 WO 2008005474 A2 20080110 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application:


The asym. cyclization of 2'-hydroxychalcones to flavanones is a basic, enzyme-catalyzed step in the biosynthesis of flavonoid natural products, but poses a long-standing problem for asym. catalysis with small mol. catalysts. Earlier claims concerning the realization of an asym. flavanone synthesis by means of camphorsulfonic acid as chiral Broensted acid catalysts were reinvestigated using accurate HPLC methods for quantification of enantiomer ratios. The previous claims of asym. induction were thus shown to be untenable. On the other hand, cinchona alkaloids serve as chiral Bronsted base mediators for the asym. cyclization of either 6'-substituted 2'-hydroxychalcones or 2',6'-dihydroxychalcones. 2',6'-Dihydroxy-4,4'-dimethoxychalcone, for instance, cyclized to give the naturally occurring naringenin-4',7-dimethyl ether in up to 64% ee at 81% conversion. The catalysis shows a marked dependency of the enantiomeric excess of the product on the catalyst, solvent and reactant concn. Based on these successful examples of asym. cyclizations of 2'-hydroxychalcones to flavanones, requirements for more active asym. catalysts can be defined.

Abstract

Asymmetric cyclization of 2'-hydroxychalcones to flavanones: catalysis by chiral Broensted acids and bases. Dittmer, Claudia; Raabe, Gerhard; Hintermann, Lukas. Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany. European Journal of Organic Chemistry (2007), (35), 5886-5898. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: EJOCFK ISSN: 1434-193X. Journal written in English. CAN 148:284927 AN 2008:45142 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method for the detn. of flavanones and flavanonols in Blumea balsanifera DC. by HPLC was established. The following HPLC conditions gave the best results: column: ZORBAX XDB-C18 (4.6 mm × 150 mm, 5 μm); mobile phase:V (methanol):V (water) = 60:40; flow rate: 0.8 mL/min; detection wavelength: 290 nm; temp.: 30°. Linearity was obtained within the range of 0.0032 μg/μl and 0.048 μg/μl (r = 0.9999 resp.) for flavanones. Linearity for flavanonols was obtained within the range of 0.0032 μg/μl and 0.048 μg/μl (r = 0.9993 resp.). The RSD of flavanones and flavanonols were 1.08% and 1.26% resp. (n = 5); av. recoveries were 98.36% and 97.86%, resp. (n = 5).

Abstract

Determination of flavanones and flavanonols in Blumea balsamifera DC. by RP-HPLC. Huang, Yong-lin; Wen, Yong-xin; Zhao, Zhi-guo; Zhu, Ting-chun. Guangxi Institute of Botany, Guilin, Guangxi, Peop. Rep. China. Guangxi Kexue (2007), 14(2), 140-142. Publisher: Guangxi Kexue Bianjibu, CODEN: GKUEAC ISSN: 1005-9164. Journal written in Chinese. CAN 148:339228 AN 2008:48322 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Two new promelacacinidin biflavonoids, mesquitol-(4α,5)-epimesquitol-4β-ol (I) and a 3',4',7,8-tetrahydroxyflavanone(3,4)-ent-epimesquitol (II), were isolated among others from the heartwood of Acacia nigrescens. The flavanone derived dimer, characterized by a unique C(3) to C(4) bridge, which links the monomers via two stereogenic and sp3 hybridized C-atoms, is the prototype of a new subgroup of the flavonoid family. Assessment of the abs. configuration of all five stereogenic centers of this novel flavanone-derived biflavonoid was achieved by correlating the chiroptical properties of the benzoyl chromophore to the abs. configuration of C(2) of the flavanone moiety and hence the abs. stereochem. of the other four chiral

Abstract

Two new promelacacinidin dimers, including a novel flavanone-flavanol dimer characterized by a unique C(3)-C(4) linkage, from the heartwood of Acacia nigrescens. Howell, H.; Malan, E.; Brand, D. J.; Kamara, B. I.; Bezuidenhoudt, B. C. B.; Marais, C.; Steenkamp, J. A. Department of Chemistry, University of the Free State, Bloemfontein, S. Afr. Chemistry of Natural Compounds (2007), 43(5), 533-538. Publisher: Springer, CODEN: CHNCA8 ISSN: 0009-3130. Journal written in English. CAN 148:258083 AN 2008:35766 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention relates to increasing at least one antioxidant level in a plant or plant product by expressing a polynucleotide that encodes a transcription factor, which is active in a flavonoid pathway. Over-expression of, for instance, a novel and newly-identified chlorogenic acid-inducing gene Cai, in a plant results in increased accumulation of chlorogenic acid and other related phenolics, which, in turn, increases the levels of beneficial antioxidant in the plant. Furthermore, the present invention boosts antioxidant levels by inhibiting the expression of at least one of the flavanone-3',5'-hydroxylase (F35h) gene, a flavanone-3'-hydroxylase (F3h), a dihydroflavonol reductase (Dfr) gene, and a chalcone isomerase (Chi) gene, in addn. to over-expression of the Cai gene.

Abstract US 2006-818516P P 20060706Priority Application

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, MT, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AP, EA, EP, OA


WO 2008005474 A3 20080417WO 2008005474 A2 20080110 WO 2007-US15437 20070705Patent No. Kind Date Application No. Date Patent Family Information

WO 2007-US15437 20070705. Priority: US 2006-818516 20060706. CAN 148:137081 AN 2008:43584 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Anticancer drug composition containing cancer cell-killing compound. Bae, Yeong Seok; Noh, Yun Hwa; Lee, Byeong Won; Park, Gi Hun. (Kyungpook National University, Office of Research Support, S. Korea). Repub. Korea (2007), 13pp. CODEN: KRXXFC KR 784628 B1 20071212 Patent written in Korean. Application: KR 2006-86623 20060908. Priority: . CAN 148:299861 AN 2008:32763 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OHO

HO

OH

OH

O

HO

OH

OH

HO

HO

O

H

H

O

OH

HO

HO

OH

OH

O

HO

OH

OH

OH

HO

OH

II

I

centers.


flavanone

Extraction of total flavanone from Herba Artemisiae Scopariae by microwave and ultrasonic assistant. Li, Zhi-ping; Yin, Du-lin; Li, You-ji; Zhang, Zhao-hui; Huang, Peng-fei. College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, Peop. Rep. China. Hunan Chengshi Xueyuan Xuebao, Ziran Kexueban (2007), 16(3), 56-58. Publisher: Hunan Chengshi Xueyuan Xuebao Bianjibu, CODEN: HCXZAB ISSN: 1672-7304. Journal written in Chinese. CAN 148:409885 AN 2008:2616 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A two-step coating/pptn. synthetic procedure has been developed for the prepn. of cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase (CSP) having a small-pore silica support. With this synthetic strategy, monodisperse, spherical CSP particles can be produced without the need for a wasteful and time-consuming sieving process. The performance of the synthesized CSP towards a variety of racemates was evaluated in the normal-phase HPLC mode. HPLC sepn. expts. revealed that the synthesized CSP exhibited a chiral recognition ability fully comparable to the corresponding com. columns prepd. using conventional large-pore silica as the support. Moreover, the synthesized CSP was successfully applied to semipreparative enantiosepn. of a new triazole antifungal agent.

Abstract

High-performance liquid chromatographic evaluation of a coated cellulose tris(3,5-dimethylphenylcarbamate) chiral stationary phase having a small-pore silica support. Liu, Yueqi; Zou, Hanfa. National Chromatographic Research and Analysis Center, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peop. Rep. China. Journal of Chromatography, A (2008), 1178(1-2), 118-125. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 148:292491 AN 2008:15039 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The title anticancer drug compn. contains cancer cell-killing compd., 2',5,7-trihydroxy-4',5'-(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbuthyl)flavanone. The compd. can kill cells of lung cancer, non-small-cell lung cancer, skin cancer, neck cancer, melanoma in skin or eyeball, crissal cancer, uterus cancer, oviduct cancer, cervical cancer, vagina cancer, vulva cancer, Hodgkin's disease, esophagus cancer, ductless gland cancer, thyroid cancer, parathyroid cancer, adrenal gland cancer, soft tissue sarcoma, urethral carcinoma, penile cancer, prostate cancer, chronic or acute leukemia, lymphocytic lymphoma, bladder cancer, ureter cancer, pelvis cancer, central nervous system tumor, primary central nervous system lymphoma, vertebra tumor, and brain stem gliomas by inhibiting the activity of topoisomerase I of mammals.

Abstract KR 2006-86623 20060908Priority Application KR 784628 B1 20071212 KR 2006-86623 20060908 Patent No. Kind Date Application No. Date Patent Family Information


flavanone

Applicability of t-flavanone to treat female pattern baldness. Sasajima, Michiyo; Moriwaki, Shigeru; Hotta, Mitsuyuki; Kitahara, Takashi; Takema, Yoshinori. Kao Corporation, Tochigi, Japan. Cosmetics & Toiletries (2007), 122(12), 77-78, 80, 82-84. Publisher: Allured Publishing Corp., CODEN: CTOIDG ISSN: 0361-4387. Journal; General Review written in English. CAN 148:253147 AN 2007:1480468 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OOH

HO

OH

MeO

OMe

I

Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible for several biol. functions, including that of antioxidant. Because of the increasing interest in these mols., methods for their synthesis and structural modification are of great importance; studies on the biol. activities of many of these compds. are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination-methoxylation procedure. A series of flavonoids that are not otherwise accessible can be prepd. using this method. As an example, 3'-demethoxysudachitin (I), a limited flavone possessing antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenger, was prepd. in fairly satisfactory yield.

Abstract

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones. Bovicelli, Paolo; D'Angelo, Vittoria; Collalto, Daniela; Verzina, Antonio; D'Antona, Nicola; Lambusta, Daniela. C.N.R. Instituto di Chimica Biomolecolare, Sezione di Roma, Universita di Roma 'La Sapienza', Rome, Italy. Journal of Pharmacy and Pharmacology (2008), Volume Date 2007, 59(12), 1697-1701. Publisher: Pharmaceutical Press, CODEN: JPPMAB ISSN: 0022-3573. Journal written in English. CAN 148:238904 AN 2008:374 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The total flavonoids in Herba Artemisiae Scopariae was extd. by microwave assisted or ultrasonic assisted extn. using 70% ethanol as extg. solvent. The influences of extg. time, rate of material to liq., microwave power or ultrasonic power on extg. rate were investigated and the technol. conditions were optimized by orthogonal. The results show that the optimal extg. conditions for ultrasonic assisted extn. are as follows: extg. time, temp., rate of material to liq. and ultrasonic power are 60min, 60°C, 5:125(g:mL) and 200 W; resp., for extn. with microwave assistant, the optimal conditions are 24 min of extg. time, 350 W of microwave power, the rate of material to liq. being 5:125 (g:mL). The extg. rate with 3.29% by ultrasonic assisted extn. is little more than that of microwave assisted extn. with 3.09%.

Abstract


flavanone

Stabilization of low-soluble cosmetic ingredients using microcapsule made of polymer/polyols. Lee, Dong-Hwan; Kim, Jin-Hui; Lee, Bum-Chun; Pyo, Hyeong-Bae. (Han-Bul Cosmetics Co., Ltd., S. Korea). PCT Int. Appl. (2007), 44pp. CODEN: PIXXD2 WO 2007145395 A1 20071221 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG,


OBJECTIVE: To study the chem. constituents of caulis spatholobi. METHODS: The constituents of caulis spatholobi were sepd. and purified with varied chromatog. techniques, and the structures were identified based on spectral data and chem. properties. RESULTS: 8 compds. were isolated from spatholobi. They were identified as spatholobus suberectus dunn (Compd. 1), formonoetis (Compd. 2), daidzein (Compd. 3), calycosin (Compd. 4), pyromucicacid (Compd. 5), 1, 3, 5-trihydroxybenzene (Compd. 6), succinic acid (Compd. 7) and β-sitosterol (Compd. 8). CONCLUSION: Spatholobus suberectus dunn is a new compd. and characterized as 7, 3', 4'-trihydoxy-6-methoxy flavanone. Compds. 4, 5, 6 and were obtained from caulis spatholobi for first time.

Abstract

Studies on the chemical constituents of Caulis Spatholobi. Han, Liping. Dept. of Clinical Pharmacy, The No.2 People's Hospital of Datong in Shanxi Province, Datong, Peop. Rep. China. Zhongguo Yaofang (2006), 17(20), 1596-1598. Publisher: Zhongguo Yaofang Zazhishe, CODEN: ZYHAA4 ISSN: 1001-0408. Journal written in Chinese. AN 2007:1457657 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Methanolic exts. of trunk exudates of Dalbergia sissoo yielded two new open-chain neoflavonoids (1, 2), a new flavonoid (3), a new flavanone (4), and 26 known compds. Their structures were elucidated by detailed spectroscopic analyses. The ability of the isolated compds. to prevent nitric oxide (NO) prodn. by LPS-stimulated J774.1 cells was also studied. All of the isolated compds. except 4, formononetin, and zenognosin B exhibited significant activity in a concn.-dependent manner. Compds. 2 and 3 were among the most potent NO prodn. inhibitors, with IC50 values of 3.19 and 6.22 μM, resp., and compd. 1 had an IC50 of 31.6 μM.

Abstract

Nitric Oxide Production Inhibitory Activity of Flavonoids Contained in Trunk Exudates of Dalbergia sissoo. Shrestha, Suraj Prakash; Amano, Yuri; Narukawa, Yuji; Takeda, Tadahiro. Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo, Japan. Journal of Natural Products (2008), 71(1), 98-101. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 148:139569 AN 2007:1474811 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. T-Flavanone, trans-3, 4'-dimethyl-3-hydroxyflavanone, promotes the growth of hair follicles and increases hair diam. It has been established for the treatment of male pattern baldness. This study examines its application to treat female pattern baldness.

Abstract


flavanone

WO 2007144368 A2 20071221 WO 2007-EP55815 20070613

R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, AL, BA, HR, MK, YU

EP 1867729 A1 20071219 EP 2006-290972 20060614Patent No. Kind Date Application No. Date Patent Family Information

Enzymic preparation of water soluble phenolic glucosides with dermocosmetic and therapeutic applications. Auriol, Daniel; Nalin, Renaud; Robe, Patrick; Lefevre, Fabrice. (Libragen, Fr.). Eur. Pat. Appl. (2007), 58pp. CODEN: EPXXDW EP 1867729 A1 20071219 Designated States R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, AL, BA, HR, MK, YU. Patent written in English. Application: EP 2006-290972 20060614. Priority: . CAN 148:53217 AN 2007:1448622 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention relates to a method of stabilizing active ingredients that have low soly. using hollow-type, multi-layered microcapsules made of hydrophobic polymer/polyhydric alc., a method prepg. the hollow-type, multilayered microcapsules, and a cosmetic compn. contg. the microcapsules. Thus, encapsulation of quercetin in poly(Me methacrylate) hollow-type, multilayered microcapsules contg. glycerin, butylene glycol and diethylene glycol monoethyl ether (5:4:1) was exemplified.

Abstract KR 2006-53025 A 20060613Priority Application KR 781604 B1 20071203 KR 2006-53025 20060613

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW

WO 2007145395 A1 20071221 WO 2006-KR3149 20060811Patent No. Kind Date Application No. Date Patent Family Information

KM, KN, KP, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-KR3149 20060811. Priority: KR 5302-5 20060613. CAN 148:85129 AN 2007:1454478 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2' cyclize to form flavanones in basic media. By synthesizing 2'-hydroxyflavylium tetrafluoroborate (I), it was possible to obtain trans-2,2'-dihydroxychalcone (II) that in soln. can evolve to 2'-hydroxyflavanone or back to 2'-hydroxyflavylium depending on the pH. The several equil. established in aq. soln. were fully characterized. The importance of including flavanones into the flavylium network of chem. reactions is briefly exploited.

Abstract

2'-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions. Petrov, Vesselin; Gomes, Raquel; Parola, A. Jorge; Jesus, Alexandre; Laia, Cesar A. T.; Pina, Fernando. REQUIMTE, Departamento de Quimica, Faculdade de Ciencias e Tecnologia, Universidade Nova de Lisboa, Caparica, Port. Tetrahedron (2007), Volume Date 2008, 64(4), 714-720. Publisher: Elsevier Ltd., CODEN: TETRAB ISSN: 0040-4020. Journal written in English. CAN 148:238903 AN 2007:1434603 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention relates to the prepn. of phenolics derivs. by enzymic condensation of phenolics selected among pyrocatechol or its derivs. including (i) protocatechuic acid and its derivs., (ii) 3,4-dihydroxycinnamic acid with its trans-isomer or caffeic acid and its derivs., esp. hydrocaffeic acid, rosmarinic acid, chlorogenic acid and caffeic acid phenethyl ester, and with its cis-isomer and its derivs., esp. esculin, (iii) dihydroxyphenylglycol, and (iv) members of the flavonoid family such as taxifolin and fustin (dihydroflavonols), fisetin (a flavonol), eriodictyol (a flavanone), , with the glucose moiety of sucrose. The prodn. of said phenolics derivs. is achieved with a glucosyltransferase (EC 2.4.1.5) obtained from a culture of Leuconostoc species, and more particularly from the culture of Leuconostoc mesenteroides NRRL B-512F. These O-glucosides of selected phenolics are new, have a soly. in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compns., such as antioxidative, antiviral, antibacterial, immune-stimulating, anti-allergic, antihypertensive, anti-ischemic, anti-arrhytmic, antithrombotic, hypocholesterolemic, anti-lipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application. All the more, glucosylated phenolics derivs. objects of the invention can be hydrolyzed by the human natural microbiotes, thus releasing the active part of the phenolic compd. upon time during their usage or by an α-glucosidase (EC 3.2.1.20).

Abstract EP 2006-290972 A 20060614Priority Application


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW


flavanone

Characterization of uridine-diphosphate dependent flavonoid glucosyltransferase from Oryza sativa. Hong, Byoung Seok; Kim, Jeong Ho; Kim, Na Yeon; Kim, Bong-Gyu; Chong, Youhoon; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Journal of Biochemistry and Molecular Biology (2007),


From the seeds of Zizyphus jujuba, five flavone-C-glycosides, isovitexin-2"-O-β-D-glucopyranoside, spinosin, and spinosin A-C have been isolated. Their structures were elucidated by spectroscopic methods and comparison with reported data.

Abstract

Flavonone-C-glycosides from the seeds of Zizyphus jujuba Mill var. spinosa Hu. Trinh, Thi Thuy; Tran, Van Sung; Franke, K.; Arnold, N.; Wessjohann, L. Institute of Chemistry, Vietnamese Academy of Science and Technology, Vietnam. Tap Chi Hoa Hoc (2007), 45(4), 496-501. Publisher: Toa Soan Tap Chi Hoa Hoc, CODEN: TCHHDC ISSN: 0378-2336. Journal written in English. CAN 148:421553 AN 2007:1429010 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The preventive antioxidant effect of the exts. of some Zingiberaceae species including Alpinia gagnepainii K. Schum., A. malaccensis (Burm. f.) Roscoe, A. conchigera Griff., A. globosa (Lour.) Horan., and Zingiber rubens Roxb. was demonstrated in term of increases in the activity of the endogenous peroxidase of blood group O by the H2O2-induced oxidn. assay. The Alpinia flavonoids (-)-pinocembrin and chalconaringenin 2'-O-Me ether of flavanone and chalcone structure, resp., also showed indirect antioxidant activity via peroxidase.

Abstract

Study on the effects of the extracts from some Alpinia and Zingiber species (Zingiberaceae) of Vietnam of the blood peroxidase activity. Phan, Minh Giang; Le, Huyen Tram; Phan, Tong Son. College of Natural Science, Vietnam National Univ., Ha Noi, Vietnam. Tap Chi Duoc Hoc (2007), 47(9), 8-11. Publisher: Bo Y Te Xuat Ban, CODEN: TCDHDQ ISSN: 0258-6967. Journal written in Vietnamese. AN 2007:1429149 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O+

HOOH

O

HO

BF 4- I II


flavanone

A review. Isoflavonoids are characteristic metabolites in legumes and an overwhelming no. of reports concerning them come from the Leguminosae. Nevertheless, the spectrum of isoflavonoid producing taxa includes the representatives of four classes of multicellular plants, namely the Bryopsida, the Pinopsida, the Magnoliopsida and the Liliopsida. At least 59 nonleguminous families have been reported to produce isoflavones sensu lato; coumestans have been reported in 3 families, coumaronochromones in 3, pterocarpans in

Abstract

Isoflavonoids in nonleguminous taxa: A rarity or a rule? Lapcik, Oldrich. Department of Chemistry of Natural Compounds, Faculty of Food and Biochemical Technology, Institute of Chemical Technology in Prague, Prague, Czech Rep. Phytochemistry (Elsevier) (2007), 68(22-24), 2909-2916. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal; General Review written in English. CAN 148:116768 AN 2007:1387893 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


There is growing interest in the potential beneficial effects of flavonoids in the aging and diseased brain. We have investigated the potential of the flavanone hesperetin and two of its metabolites, hesperetin-7-O-β-D-glucuronide and 5-nitro-hesperetin, to inhibit oxidative stress-induced neuronal apoptosis. Exposure of cortical neurons to hydrogen peroxide led to the activation of apoptosis signal-regulating kinase 1 via its de-phosphorylation at Ser963, the phosphorylation of c-jun N-terminal kinase and c-Jun (Ser73) and the activation of caspase 3 and caspase 9. While hesperetin glucuronide failed to exert protection, both hesperetin and 5-nitro-hesperetin were effective at preventing neuronal apoptosis via a mechanism involving the activation/phosphorylation of both Akt/protein kinase B and extracellular signal-regulated kinase 1 and 2 (ERK1/2). Protection against oxidative injury and the activation of Akt and ERK1/2 followed a bell-shaped response and was most apparent at 100 nmol/L concns. The activation of ERK1/2 and Akt by flavanones led to the inhibition of the pro-apoptotic proteins, apoptosis signal-regulating kinase 1, by phosphorylation at Ser83 and Bad, by phosphorylation at both Ser136 and Ser112 and to the inhibition of peroxide-induced caspase 9 and caspase 3 activation. Thus, flavanones may protect neurons against oxidative insults via the modulation of neuronal apoptotic machinery.

Abstract

Activation of pro-survival Akt and ERK1/2 signalling pathways underlie the anti-apoptotic effects of flavanones in cortical neurons. Vauzour, David; Vafeiadou, Katerina; Rice-Evans, Catherine; Williams, Robert J.; Spencer, Jeremy P. E. Molecular Nutrition Group, School of Chemistry, Food and Pharmacy, University of Reading, Reading, UK. Journal of Neurochemistry (2007), 103(4), 1355-1367. Publisher: Blackwell Publishing Ltd., CODEN: JONRA9 ISSN: 0022-3042. Journal written in English. CAN 148:159910 AN 2007:1390858 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


We cloned a uridine-diphosphate dependent glycosyltransferase RUGT-10 from Oryza sativa. The recombinant enzyme was expressed by glutathione-S transferase gene fusion system in Escherichia coli. RUGT10 showed different regioselectivity depending on the structures of substrates (e.g. flavanone, flavonol, and flavone). Apparently, flavanone such as naringenin and eriodictyol gave one 7-O-glucoside while flavone and flavonol gave more than two products with preferential glucosylation position of hydroxyl group at C-3 position.

Abstract

40(6), 870-874. Publisher: Korean Society for Biochemistry and Molecular Biology, CODEN: JBMBE5 ISSN: 1225-8687. Journal written in English. CAN 148:278664 AN 2007:1422285 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

JP 2006-144264 20060524Priority Application JP 2007314446 A 20071206 JP 2006-144264 20060524 Patent No. Kind Date Application No. Date Patent Family Information

AMPK activators for activation of metabolism, and foods and beverages containing them. Murase, Takatoshi. (Kao Corp., Japan). Jpn. Kokai Tokkyo Koho (2007), 10pp. CODEN: JKXXAF JP 2007314446 A 20071206 Patent written in Japanese. Application: JP 2006-144264 20060524. Priority: . CAN 148:32598 AN 2007:1386872 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Polymnia sonchifolia, commonly known as "yacon", was originally cultivated at Andes mountains in South America. Recently, the specie attracted worldwide attention because of its wide range of uses, for example in the control of diabetes melitus, besides the antifungal and pesticidal compds. were found in the leaves. This study describes the identification of two flavonoids: 3', 5, 7 trihydroxy-3, 4'-dimethoxyflavone (compd. 1) and 3', 4', 5-trihydroxy-7-methoxy flavanone (compd. 2) and two sesquiterpenes lactones: enhydrin (compd. 3) and a mixt. of enhydrin and uvedalin (compd. 4) isolated from Polymnia sonchifolia leaves and their effects on the aflatoxin prodn. by Aspergillus flavus. The identification of the compds. were achieved by 1H and 13C NMR. All compds. were tested in different concn., to evaluate the growth of Aspergillus flavus culture and the prodn. of aflatoxin. The compd. 1, at the concn. 15 μg/mL, inhibited 25% of the aflatoxin B1 prodn. (p<0.01). The compd. 4 inhibited 34% and 76% of the fungal growth and AFB1 prodn. resp. These results show that Polymnia sonchifolia can be used for the development of agents to control aflatoxin B1 prodn. by Aspergillus flavus.

Abstract

Inhibitory activity of compounds isolated from Polymnia sonchifolia on aflatoxin production by Aspergillus flavus. Park, Adriana; Goncalez, Edlayne; Felicio, Joana D'arc; Pinto, Marina Mori; Rossi, Maria Helena; Simoni, Isabela Cristina; Lopes, Marcia Nassser. Instituto de Quimica, Universidade Estadual Paulista, Araraquara, SP, Brazil. Brazilian Journal of Microbiology (2007), 37(2), 199-203. Publisher: Brazilian Society of Microbiology, CODEN: BJMRAH ISSN: 1517-8382. Journal; Computer Optical Disk written in English. CAN 148:421286 AN 2007:1387678 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


9 and rotenoids in 8 families. Prenylated isoflavones have been found in 15 non-leguminous families and isoflavone dimers, heterodimers or oligomers in three families. More than 200 different isoflavonoid aglycons have been reported in non-legumes altogether. The no. of individual structures is even greater if the variety of glycosides are considered. Enzymol. and genetics of isoflavonoid biosynthesis have been studied almost exclusively in legumes, with the exception of a few model plants (i.e. Beta vulgaris, Arabidopsis thaliana, Nicotiana tabacum and Zea mays). The key step at the very beginning of the isoflavonoid metabolic pathway is the oxidn. of flavanone connected with the migration of aryl moiety from C2 to C3 mediated by a CYP450 enzyme isoflavone synthase (IFS), which has been identified and cloned in multiple legumes and in sugar beet (Beta vulgaris, Chenopodiaceae). No information is available about the enzyme(s) responsible for the biosynthesis of isoflavonoid core in other taxa. Exptl. data demonstrates the capability of numerous enzymes of non-legume origin to metabolize isoflavones as alternative substrates to other phenolics.


flavanone


Flavanone glycosides were successfully sepd. from the crude ext. of P. trifoliata by preparative centrifugal partition chromatog. with a two-phase solvent system composed of Et acetate-acetonitrile-water (3:2:5, vol./vol./vol.). Naringin (50.0 mg), neoponcirin (16.8 mg), and poncirin (71.9 mg) were purified from the 524 mg crude ext. in only 1 step. The purities of the isolated compds. were detd. to be >90% by HPLC anal. and their structures were elucidated by 1H NMR, 13C NMR, and ESI-MS.

Abstract

One step purification of flavanone glycosides from Poncirus trifoliata by centrifugal partition chromatography. Kim, Chul Young; Lee, Hee Ju; Lee, Mi Kyeong; Ahn, Mi-Jeong; Kim, Jinwoong. Natural Product Research Center, KIST Gangneung Institute, Gangneung, S. Korea. Journal of Separation Science (2007), 30(16), 2693-2697. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 148:213554 AN 2007:1367856 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


High-resoln. Sustained off resonance irradn. (SORI) CID was employed to distinguish four pairs of isomeric diglycosyl flavonoids in the neg. mode using the electrospray ionization Fourier transform ion cyclotron resonance mass spectrometry (ESI FTICR MS). All of these isomers can be distinguished via MS/MS data. For these diglycosyl flavones and flavanones, the deprotonated α1→6 linkage diglycosyl flavonoids produce fewer fragments than the α1→2 linkage type compds. and the Retro-Diels-Alder (RDA) reaction in MS/MS only takes place when the aglycon is a flavanone and glycosylated with an α1→2 intersaccharide linkage disaccharide. The deprotonation sites after collisional activation are discussed according to the high mass accuracy and high-resoln. data of tandem spectrometry. Some of these high-resoln. SORI CID product ions from α1→2 linkage diglycosyl flavonoids involve multibond cleavages; the possible mechanism is discussed based on the computer modeling using Gaussian 03 program package at the B3LYP/6-31G level of theory. Unambiguous elementary compn. data provides fragmentation information that has not been reported previously.

Abstract

A Study of Isomeric Diglycosyl Flavonoids by SORI CID of Fourier Transform Ion Cyclotron Mass Spectrometry in Negative Ion Mode. Yan, Cunyu; Liu, Shuying; Zhou, Yihan; Song, Fengrui; Cui, Meng; Liu, Zhiqiang. Changchun Center of Mass Spectrometry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Peop. Rep. China. Journal of the American Society for Mass Spectrometry (2007), 18(12), 2127-2136. Publisher: Elsevier Inc., CODEN: JAMSEF ISSN: 1044-0305. Journal written in English. CAN 148:186244 AN 2007:1384310 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Title foods and beverages, useful for prevention and/or treatment of life style-assocd. chronic metabolic diseases (e.g., obesity and diabetes), contain flavones and/or flavanones as AMPK activators. Thus, 2-phenylchromone at 150 μM significantly enhanced phosphorylation of AMPKα and β in Hepa 1-6.

Abstract


flavanone


Bioassay-guided fractionation of the methanolic exts. of the pulp and seeds of the fruits of Syzygium samarangense (Blume) Merr. and L.M. Perry led to the identification of four cytotoxic compds. and eight antioxidants on the basis of HPLC-PDA anal., MS, and various NMR spectroscopic techniques. Three C-methylated chalcones, 2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone (1), 2',4'-dihydroxy-3'-methyl-6'-methoxychalcone (stercurensin, 2), and 2',4'-dihydroxy-6'-methoxychalcone (cardamonin, 3), were isolated and displayed cytotoxic activity (IC50 = 10, 35, and 35 μM, resp.) against the SW-480 human colon cancer cell line. Also a no. of known antioxidants were obtained including six quercetin glycosides: reynoutrin (4), hyperin (5), myricitrin (6), quercitrin (7), quercetin (9), and guaijaverin (10), one flavanone: (S)-pinocembrin (8), and two phenolic acids: gallic acid (11) and ellagic acid (12).

Abstract

Cytotoxic chalcones and antioxidants from the fruits of Syzygium samarangense (Wax Jambu). Simirgiotis, Mario J.; Adachi, Seiji; To, Satoshi; Yang, Hui; Reynertson, Kurt A.; Basile, Margaret J.; Gil, Roberto R.; Weinstein, I. Bernard; Kennelly, Edward J. Department of Biological Sciences, Lehman College and The Graduate Center, City University of New York, Bronx, NY, USA. Food Chemistry (2008), 107(2), 813-819. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 148:237776 AN 2007:1344692 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This invention relates to 5,7,3',4'-tetrahydroxy flavanone having protective effects on the UV-induced cell death in human keratinocytes to inhibit apoptosis of human keratinocytes caused by UV by inhibiting prodn. of reactive oxygen species due to UV in cells and activity redn. of p38 MAP(mitogen-activated protein) kinase through treating the human skin exposed to UV with the flavonoid. A compn. for inhibiting apoptosis of human keratinocytes caused by UV comprises the 5,7,3',4'-tetrahydroxy flavanone isolated from the plant such as Viscum album var. as an effective ingredient, wherein the compn. is a cosmetic or pharmaceutical compn. and is formulated as granule, tablet, capsule, drink, cream or lotion. The daily dosage of 5,7,3',4'-tetrahydroxy flavanone is 0.1-1000 mg per adult.

Abstract KR 2006-5735 20060119Priority Application KR 729732 B1 20070620 KR 2006-5735 20060119 Patent No. Kind Date Application No. Date Patent Family Information

5,7,3',4'-Tetrahydroxy flavanone having protective effects on the UV-induced cell death in human keratinocytes. Cho, Ssang Goo; Lee, Eung Ryoung; Kang, Yong Jin. (Konkuk University Industrial Cooperation Corp., S. Korea). Repub. Korea (2007), No pp. given. CODEN: KRXXFC KR 729732 B1 20070620 Patent written in Korean. Application: KR 2006-5735 20060119. Priority: . CAN 147:548118 AN 2007:1345898 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 108:

In order to make use of the resources of orange peel, avoiding waste, purely phys. process flow and spectrophotometry to introduce the method of which extd. the flavanone from the orange peel were used, and the flavanone which withdrew from the lotus rhizome was checked. By this method getting the contents of the total flavanone of orange peel was C = 4.49% and rate of the recovery was 98.0%. Using this text which provided the withdrawal and purifying methods to get the outcome and purity of the flavanone were all very high. This method was purely phys. process, and had no chem. change and pollution. It was ideal to withdraw the flavanone of orange peel.

Abstract

Extraction and distinguish of the total flavanone from orange peel. Huang, Suoyi; Luo, Yan; Zhang, Jingxuan; Wang, Sanyan; Lu, Huiyu. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(8), 1495-1496. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:409803 AN 2007:1342001 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of Ficus microearpa L. leaf, avoiding waste, purely phys. process flow was used and the spectrophotometry method of which withdrawed the flavanone from Ficus microearpa L. leaf was introduced and the flavanone which withdrawed from Ficus microearpa L. leaf was checked. The contents of the total flavanone of onion was C=8.36% and rate of the recovery was 97.9%. Using this text which provided the withdrawal and purifying methods the outcome and purity of the flavanone were all very high. This method was purely phys. process, and had no chem. change and pollution. It was ideal to withdraw the flavanone of Ficus microearpa L. leaf.

Abstract

Total flavanone of ficus microcarpa L. leaf withdraws and distinction. Long, Guangjin; Huang, Ye; Jiang, Linhua; Huang, Suoyi. Undergraduate of Clinical Medicine, Grade 2001, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(8), 1425-1426. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. AN 2007:1342121 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of total flavanone in pericarp of longan, extn. and identification were discussed. The flavonids were extd. with ethanol. Spectrophotometry was used to check the flavanone. The total flavanone in the pericarp was 1.101 mg/mL and the rate of recovery was 99.98%. The extn. and purifying methods in this expt. could get the outcome and the purity of the flavanone very high. This method was a purely phys. process and had not any pollution. It was an ideal way to ext. the flavanone of longan skin.

Abstract

Extraction and identification of total flavanone from longan pericarp. Huang, Suoyi; Tang, Yulian; Li, Haini; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Zhongyaocai (2006), 29(8), 767-769. Publisher: Guojia Shipin Yaopin Jiandu Guanliju, Zhongyaocai Xinxi Zhongxinzhan, CODEN: ZHONAR ISSN: 1001-4454. Journal written in Chinese. AN 2007:1342302 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Simultaneous determination of flavonoids in Ixeridium gracile by micellar electrokinetic chromatography. Zhang, Yu; Chen, Juan; Ma, Xue-Mei; Shi, Yan-Ping. Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Peop. Rep. China. Journal of Pharmaceutical and Biomedical Analysis (2007), 45(5), 742-746. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 148:62302 AN


Flavan-3-ols, such as green tea catechins represent a major group of phenolic compds. with significant medicinal properties. The authors describe the construction and optimization of Escherichia coli recombinant strains for the prodn. of mono- and dihydroxylated catechins from their flavanone and phenylpropanoid acid precursors. Use of glucose minimal medium, Fe(II), and control of oxygen availability during shake-flask expts. resulted in prodn. yield increases. Addnl. prodn. improvement resulted from the use of medium rather than high-copy no. plasmids and, in the case of mono-hydroxylated compds., the addn. of extracellular cofactors in the culture medium. The established metabolic engineering approach allowed the biosynthesis of natural catechins at high purity for assessing their possible insulinotropic effects in pancreatic β-cell cultures. The authors demonstrated that (+)-afzelechin and (+)-catechin modulated the secretion of insulin by pancreatic β-cells. These results indicate the potential of applying metabolic engineering approaches for the synthesis of natural and non-natural catechin analogs as drug candidates in diabetes treatments.

Abstract

Standardized biosynthesis of flavan-3-ols with effects on pancreatic beta-cell insulin secretion. Chemler, Joseph A.; Lock, Lye T.; Koffas, Mattheos A. G.; Tzanakakis, Emmanuel S. Department of Chemical and Biological Engineering, State University of New York at Buffalo, Buffalo, NY, USA. Applied Microbiology and Biotechnology (2007), 77(4), 797-807. Publisher: Springer, CODEN: AMBIDG ISSN: 0175-7598. Journal written in English. CAN 148:160360 AN 2007:1329755 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Using the effects on histamine release of Bidens parviflora Willd. to identify biol. active compds. Five chalcones,two flavanones and two aurones were isolated and identified as 2'-hydroxy-3,4,4'-trimethoxy chalcone (1), 4,2',4',6'-tetramethoxy dihydrochalcone (2), 3,4,2',4',6'-pentamethoxy dihydrochalcone (3,I), 7,3',4'-trihydroxy flavanone (4), 3',4'-dihydroxy flavanone 7-O-β-D-glucoside (5), 3,4,2'-trihydroxy chalcone 4'-O-β-D-glucoside (6), 3-methoxy-4,2',3'-trihydroxy chalcone 4'-O-β-D-glucoside (7), sulfuretin 6-O-β-D-glucoside (8), and maritimetin 7-O-β-D-glucoside (9). Compds. 1-7 were obtained from Bidens parviflora Willd. for the first time, compd. 3 is a new dihydrochalcone, and 1 and 2 were isolated from natural sources for the first time. The chalcones glucosides and aurones glucosides exhibited activity in anti-allergic assays of histamine in rat mast cells induced by an antigen-antibody reaction and the inhibitory activity of NO prodn. by macrophages is compared and discussed.

Abstract

Structures and anti-histamine activity of chalcones & aurones compounds from Bidens parviflora Willd. Wang, Jue; Wang, Naili; Yao, Xinsheng; Kitanaka, Susumu. School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Peop. Rep. China. Asian Journal of Traditional Medicines (2007), 2(1), 23-29. Publisher: Hong Kong Asiamed Publish House, CODEN: AJTMCS ISSN: 1817-4337. Journal written in English. AN 2007:1338626 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Separation of two new prenylated dihydroflavonoids from Dolichos tenuicaulis (Baker) Craib by high-speed counter-current chromatography. Peng, Jin-Yong; Xu, Li-Na; Han, Xu; Xu, You-Wei; Qi, Yan; Xu, Qi-Wei. School of Pharmacy, Dalian Medical University, Dalian, Peop. Rep. China. Fenxi Huaxue (2007), 35(10), 1444-1448. Publisher: Kexue Chubanshe, CODEN: FHHHDT ISSN: 0253-3820. Journal written in Chinese. CAN 148:17960 AN 2007:1312362 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Polyphenols are abundant dietary plant constituents assocd. with health-promoting effects. Factors influencing the bioavailability of dietary polyphenols, esp. flavanols, flavonols, flavanones, flavones, and hydroxycinnamic (phenolic) acids, are discussed. Most factors tested so far indicate that bioaccessibility, defined as the amt. of compd. reaching the enterocyte in a form suitable for absorption, is the most important factor detg. the polyphenols absorption in the gut. Factors improving the absorption of flavonols, notably quercetin and its metabolites, are the nature of the sugar moiety and soly. as modified by ethanol, fat, and emulsifiers. The absorption of flavanols, notably green tea catechins, is affected by epimerization reactions occurring during food processing, presence of lipid and carbohydrate, and is improved in the presence of piperine and tartaric acid. The bioavailability of flavanones, such as hesperidin, is strongly affected by the type of sugar moiety. Phenolic acids bioavailability is affected by the attached sugar, which can covalently link these compds. to the cereal bran matrix. In the few examples tested, absorption of polyphenols is dependent on the release from food matrix. There are only a few examples reported, but where information is available, the absorption increases with dose but is sometimes linear and sometimes satd. The lack of systematic information on the effects of other components on the bioavailability of polyphenols needs to be addressed. More human studies are needed to establish general principles affecting polyphenol absorption in vivo. Information from such expts. could be useful for the optimal design of future bioefficacy studies.

Abstract

Interactions affecting the bioavailability of dietary polyphenols in vivo. Scholz, Susanne; Williamson, Gary. Nestle Research Center, Lausanne, Switz. International Journal for Vitamin and Nutrition Research (2007), 77(3), 224-235. Publisher: Hogrefe & Huber Publishers, CODEN: IJVNAP ISSN: 0300-9831. Journal; General Review written in English. CAN 148:10278 AN 2007:1315158 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A micellar electrokinetic chromatog. (MEKC) method has been developed for the quant. anal. of five flavonoids: luteolin 7-O-glucoside (LG), 2',4'-dihydroxy-dihydrochalcone (DD), 2',4'-dihydroxy-chalcone (DC), 7-hydroxy-flavanone (HF) and quercetin 3-O-galactoside (QG) in Ixeridium gracile with UV detection at 275 nm. The applied voltage was 25 kV and the capillary temp. was kept const. at 25°. The effects of buffer pH, the concn. of electrolyte and org. modifier on migration behavior were studied. Optimum sepn. condition was achieved with 15 mM borate, 30 mM SDS and 10% (vol./vol.) ethanol at pH 10.5. Regression equations showed good linear relationships (correlation coeffs.: 0.9984, 0.9991, 0.9994, 0.9995 and 0.9997) between the peak area of each compd. and their concns. The relative std. deviations (R.S.D.) of the migration time and peak area were less 1.67 and 3.53% (intra-day), and 1.82 and 3.73% (inter-day), resp., under the optimum sepn. conditions. The contents of the five active compds. in I. gracile were detd. with satisfactory repeatability and recovery.

Abstract 2007:1318094 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Some plant flavonoids in the form of whole plant exts. were used topically for skin inflammatory disorders. Since matrix metalloproteinase-1 (MMP-1, collagenase-1) plays an important role in unbalanced turn-over or rapid breakdown of collagen mols. in human inflamed/UV-irradiated skin, the effects of natural flavonoids on MMP-1 activity and MMP-1 expression were studied to establish the therapeutic potential. Against recombinant human MMP-1, flavonols such as quercetin and kaempferol were strong inhibitors with IC50 values of 39.6 and 43.7 μM, resp., while flavones such as apigenin and wogonin showed only weak inhibitory activity. In addn., quercetin, kaempferol, apigenin, and wogonin (12.5-25.0 μM) strongly inhibited MMP-1 induction in

Abstract

Inhibition of mammalian collagenase, matrix metalloproteinase-1, by naturally-occurring flavonoids. Lim, Hyun; Kim, Hyun Pyo. College of Pharmacy, Kangwon National University, Chunchon, S. Korea. Planta Medica (2007), 73(12), 1267-1274. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 148:112688 AN 2007:1301557 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanones are the common precursors of plant polyphenolic compds. collectively known as flavonoids. Leguminous plants have evolved a distinct class of flavanone mols., known as 5-deoxyflavanones that play important roles in their symbiotic interactions. A four-step metabolic circuit was constructed in Escherichia coli with plant genes from heterologous origins: 4-coumarate:CoA ligase from Petroselinum crispum, chalcone synthases (CHS) from Medicago sativa and Petunia x hybrida and chalcone reductase and chalcone isomerase from M. sativa. Evaluation of the different recombinant strains in shake flask expts. demonstrated that P. hybrida rather than M. sativa CHS resulted in the highest liquiritigenin prodn. levels in glucose minimal medium, starting from precursor p-coumaric acid. Expression of the same recombinant pathway in Saccharomyces cerevisiae resulted in the accumulation of both 5-hydroxyflavanone and 5-deoxyflavanone, with the yields of the later lower than that achieved in E. coli. Other phenylpropanoid acid precursors, such as cinnamic acid and caffeic acid could also be metabolized through the recombinant pathway, yielding corresponding 5-deoxyflavanone compds. The construction of such recombinant strains for 5-deoxyflavanone biosynthesis offers an alternative way to biochem. characterize flavonoid biosynthetic enzymes and promising prodn. platforms for the biosynthesis of such high-value natural products.

Abstract

Biosynthesis of 5-deoxyflavanones in microorganisms. Yan, Yajun; Huang, Lixuan; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, the State University of New York, Buffalo, NY, USA. Biotechnology Journal (2007), 2(10), 1250-1262. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: BJIOAM ISSN: 1860-6768. Journal written in English. CAN 148:166958 AN 2007:1306947 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The sepn. and isolation of chem. constituents from Dolichos tenuicaulis (Baker) Craib by high-speed counter-current chromatog. (HSCCC) were achieved. The solvent system composed of petroleum ether:ethyl acetate:ethanol:water (1:1.2:1.2:1, V/V) was selected to purify the compds., the upper phase was used as the stationary phase, the lower phase was used as the mobile phase at a flow rate of 2.0 mL/min, and the app. was controlled at 800 r/min and 30°, and the effluent was monitored at 280 nm. Under the optimized conditions, two pure compds. with the amts. of 95.3 mg and 84.5 mg were produced from 400 mg crude sample only in one run, and the chem. structures of the targets were elucidated as (2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (1) and (2S)-5,2',6'-trihydroxy-8-prenyl-6,7-(3-prenyl-2,2-dimethylpyrano)-3',4'-(2,2-dimethyl-1-keone-cyclohexadiene)-flavanone (2) by physico-chem. properties and spectra data. This sepn. method was simple, and the compds. 1 and 2 were new compds.


flavanone

Anthocyanin biosynthesis is strongly up-regulated in ripening fruit of grapevines (Vitis vinifera L.) grown under drought conditions. We investigated the effects of long-term water deficit on the expression of genes coding for flavonoid and anthocyanin biosynthetic enzymes and related transcription factors, genes sensitive to endogenous [sugars, abscisic acid (ABA)] and environmental (light) stimuli connected to drought stress, and genes developmentally regulated in ripening berries. Total anthocyanin content has increased at harvest in water-stressed (WS) fruits by 37-57% in two consecutive years. At least 84% of the total variation in anthocyanin content was explained by the linear relationship between the integral of mRNA accumulation of the specific anthocyanin biosynthetic gene UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT) and metabolite content during time series from veraison through ripening. Chalcone synthase (CHS2, CHS3) and flavanone 3-hydroxylase (F3H) genes of the flavonoid pathway showed high correlation as well. Genes coding for flavonoid 3',5'-hydroxylase (F3'5'H) and O-methyl-transferase (OMT) were also up-regulated in berries from dehydrated plants in which anthocyanin compn. enriched in more hydroxylated and more methoxylated derivs. such as malvidin and peonidin, the grape anthocyanins to which human gastric bilitranslocase displays the highest affinity. The induction in

Abstract

Transcriptional regulation of anthocyanin biosynthesis in ripening fruits of grapevine under seasonal water deficit. Castellarin, Simone D.; Pfeiffer, Antonella; Sivilotti, Paolo; Degan, Mirko; Peterlunger, Enrico; Di Gaspero, Gabriele. Dipartimento di Scienze Agrarie e Ambientali, University of Udine, Udine, Italy. Plant, Cell and Environment (2007), 30(11), 1381-1399. Publisher: Blackwell Publishing Ltd., CODEN: PLCEDV ISSN: 0140-7791. Journal written in English. CAN 148:351375 AN 2007:1282072 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chem. analyses of the stem bark of E. sigmoidea (Fabaceae) yielded a new flavonoid, designated sigmoidin L (1), the known erythrinasinate, E-p-coumaric acid docosyl ester, and 3'-prenylnaringenin, reported here for the 1st time for the stem bark of E.sigmoidea. The structure of 1 was established by chem. and spectroscopic means as 5,7,3',4'-tetrahydroxy-5'-[3''-methyl-4''-oxobut-(1''Z)enyl]flavanone. Sigmoidin L exhibited significant antibacterial potency in vitro against Staphylococcus aureus and Proteus vulgaris.

Abstract

Sigmoidine L, a new antibacterial flavonoid from Erythrina sigmoidea (Fabaceae). Kouam, Jacques; Etoa, Francois-Xavier; Mabeku, Laure BrigitteKouitcheu; Fomum, Zacharias Tanee. Department of Organic Chemistry, Faculty of Science, University of Yaounde I, Cameroon. Natural Product Communications (2007), 2(11), 1105-1108. Publisher: Natural Product Inc., CODEN: NPCACO ISSN: 1934-578X. Journal written in English. CAN 148:163619 AN 2007:1283900 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


12-O-tetradecanoylphorbol 13-acetate-treated human dermal fibroblasts, but naringenin (a flavanone) did not. By means of the electrophoretic mobility shift assay, these flavonoids were also found to inhibit activation of the transcription factor, activator protein-1 (AP-1). Moreover, quercetin inhibited extracellular signal-regulated protein kinase (ERK) and p38 mitogen-activated protein kinase (MAPK) activation, and kaempferol inhibited p38 MAPK and c-Jun N-terminal kinase (JNK) activation among the MAPKs tested. In contrast, flavones and naringenin did not inhibit the activation of these 3 MAPKs. These results have shown, for the 1st time, that naturally-occurring flavonoids (quercetin, kaempferol, apigenin, and wogonin) inhibit MMP-1 and down-regulate MMP-1 expression via an inhibition of the AP-1 activation although the cellular inhibitory mechanisms differ depending on their chem. structures. Therefore, certain plant flavonoids or plant exts. with these flavonoids as major components may be beneficial to treat some skin inflammatory disorders and to protect skin from photoaging.


flavanone

Separation and purification of flavanone from aloes using four-course analogue moving bed chromatography. Zhang, Dabing; Wang, Yahui; Meng, Qiang; Wang, Yan. (Jiangsu Hanbon Sci. & Tech. Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. CODEN: CNXXEV CN 101066959 A 20071107 Patent written in Chinese. Application: CN 1002-2902 20070524. Priority: . CAN 148:17498 AN 2007:1280572 CAPLUS (Copyright (C) 2008 ACS on


O

O

O

OH

R2

1R Ar

I

The claimed flavone derivs. have general structure I (R1 = C1-3 (un)branched alkyl; Ar = (un)substituted Ph; R2 = chain or cyclic tertiary amine NR3R4; R3 and R4 = Me, Et, C1-4 alkyl alc., carboxylic acid, ester, amine, or forming 5- or 6-membered ring with oxygen or nitrogen). Title compds. were prepd. from 2-acetyl-1,3,5-trihydroxybenzene via etherification, arom. aldehyde condensation, amination, cyclization, and selective dealkylation to provide the claimed products. The flavone deriv. can be used to prep. antineoplastic medicine.


Multi-substituted flavanone derivative, its preparation and application. Hu, Yongzhou; Liu, Tao; He, Qiaojun; Yang, Bo; Luo, Peihua. (Zhejiang University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 14pp. CODEN: CNXXEV CN 101066963 A 20071107 Patent written in Chinese. Application: CN 1006-9248 20070608. Priority: . CAN 148:33628 AN 2007:1280586 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


WS plants of structural and regulatory genes of the flavonoid pathway and of genes that trigger brassinosteroid hormonal onset of maturation suggested that the interrelationships between developmental and environmental signalling pathways were magnified by water deficit which actively promoted fruit maturation and, in this context, anthocyanin biosynthesis.


flavanone

In order to make use of the resources of the gingers, avoid wasting, approach the extn. and detn. contents of the total flavanone of the gingers, purely phys. process flow was used and the method of which extd. the flavanone from the gingers was introduced, and

Abstract

The total flavanone of gingers extraction and the distinction. Huang, Suoyi; Luo, Yan; Zhang, Jingxuan; Wang, Sanyan; Lu, Huiyu. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(5), 779-780. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:303448 AN 2007:1249753 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of murraya paniculata, the extn. of total flavanone of Murraya paniculata was studied. The flavonoids were extd. by ethanol as the solvent from Murraya kwangsiensis with ultrasonic wave and ethanol extn. Using spectrophotometry, the flavanone of murraya paniculata was extd. and checked. By this method getting the d. of the total flavanone of murraya paniculata was C = 1.0128 mg/mL and the rate of recovery was 102.5%. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone were all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone of murraya paniculata.

Abstract

Total flavanone of Murraya paniculata extraction and the identification by ultrasonic wave. Huang, Suoyi; Yang, Wenhui; Li, Weibin; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(3), 395-396. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:303454 AN 2007:1250332 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Title method comprises hot water extg. dry Aloes, filtering, Et acetate extg. at room temp. for 3-5 h, filtering, evapg. to dry; purifying ext. via four-course analog moving bed chromatog., eluting with methanol-water (45:55), vacuum concg., freeze drying.

Abstract CN 2007-10022902 20070524Priority Application CN 101066959 A 20071107 CN 2007-10022902 20070524 Patent No. Kind Date Application No. Date Patent Family Information SciFinder (R))


flavanone

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, MT, NL, PL,

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW

WO 2007122251 A3 20080306WO 2007122251 A2 20071101 WO 2007-EP54065 20070425Patent No. Kind Date Application No. Date Patent Family Information

Synergistic mixture of glycosyl flavanones and xanthines for browning skin or hair. Vielhaber, Gabriele; Schaper, Karin; Lange, Sabine. (Symrise G.m.b.H. & Co. K.-G., Germany). PCT Int. Appl. (2007), 75pp. CODEN: PIXXD2 WO 2007122251 A2 20071101 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, MT, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-EP54065 20070425. Priority: US 2006-794514 20060425. CAN 147:474339 AN 2007:1243152 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A characterization of flavonols, betacyanins and possible anthocyanins from the fruits of several types of cacti by LC/ESI/MS-MS was conducted. The anal. included fruits from the Mammillaria and Opuntia genera. Previous work by Miller on the floral pigments of Echinocereus demonstrated the presence of a variety of flavone, flavonol, flavanone, and dihydroflavonol glycosides based upon the fundamental aglycons naringenin, eriodictyol, dihydrokaempferol, dihydroquercetin, apigenin, luteolin, kaempferol, and quercetin. Work on the fruits of Cactaceae has been limited to three species of Opuntia and the identification of betacyanins. The current investigation attempted to verify the presence of similar flavonols and betacyanins in the fruits of other members of the Cactaceae family and to explore the possible presence of anthocyanins. We have been able to identify several flavonols based on luteolin and isorhametin within the fruits as well as several tentatively identified anthocyanidins based on cyanidin and delphinidin.

Abstract

Flavonoids from Cactaceae Fruits. Johnson, Charles A.; Walker, Mindy; Scholes, Chad M.; Chapman, James M. Department of Chemistry, Rockhurst University, Kansas City, MO, USA. Abstracts, 42nd Midwest Regional Meeting of the American Chemical Society, Kansas City, MO, United States, November 7-10 (2007), GENERAL-294. Publisher: American Chemical Society, Washington, D. C CODEN: 69JZDO Conference; Meeting Abstract written in English. AN 2007:1247172 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


the flavanone which extd. from the Lotus rhizome was checked. The content of the total flavanone of gingers was 2.63% and the rate of recovery was 97.8%. This method was purely phys. process, and had no chem. pollution. It was ideal ways to ext. the flavanone of gingers.


flavanone

Theor. calcn. of electronic CD (ECD) of the rotationally restricted 3,8''-biflavonoid (+)-morelloflavone using time dependent d. functional theory (TDDFT), performed at 298 K at B3LYP-SCRF/6-31G*//B3LYP/6-31G* level with COSMO model, permitted

Abstract

Theoretical Calculation of Electronic Circular Dichroism of the Rotationally Restricted 3,8''-Biflavonoid Morelloflavone. Ding, Yuanqing; Li, Xing-Cong; Ferreira, Daneel. National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, and Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, MS, USA. Journal of Organic Chemistry (2007), 72(24), 9010-9017. Publisher: American Chemical Society, CODEN: JOCEAH ISSN: 0022-3263. Journal written in English. CAN 148:78780 AN 2007:1215556 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method to ext. flavonoids from corn stigma was established in order to make use of the resources of corn silk and avoid waste. Flavonoids were extd. using purely phys. process and detected with spectrophotometry. The results showed that content of total flavonoids in corn silk was 6.45% and rate of the recovery was 97.9%. The output and purity of flavonoids with the process were all very high. This method was purely phys. process, and had not any chem. change and pollution. It was an ideal way to ext. flavonoids of corn silk.

Abstract

The total flavanone of corn silk extraction and distinction. Huang, Ye; Long, Guangjin; Jiang, Linhua; Huang, Suoyi. Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(6), 1008-1009. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:139531 AN 2007:1218713 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention concerns the use of a formulation contg. or consisting of (a) one or more xanthines, (b) one or more flavanone glycoside contg. glucose or rhamnose or saccharide radicals, and (c) optionally a skin or hair conditioning or cleansing substance, wherein the ratio by wt. of the amt. of (a) xanthines contained in the formulation to the amt. of (b) flavanone glycoside contained in total in the formulation is in the range from 50:1 to 1:10, as an agent for browning skin or hair in vivo. A skin browing water-in-oil emulsion with UVA/B broadband protection contains caffeine, naringin, dihydroacetone and other ingredients. A mixt. of caffeine and naringin or morin are highly synergistic active ingredient combinations, while mixts. of caffeine and epicatechin or phloridzin have an antagonistic rather than a synergistic effect.


PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AP, EA, EP, OA


flavanone

The sepn. of flavonoids in medicinal plants and raw cosmetics was described by high performance liq. chromatog. with a photodiode array detector. The influence of wavelength, mobile phase component, sample treatment including solvent selection and extn. and other conditions affecting the sepn. were optimized. Elution with methanol/phosphoric acid (pH 2.0) in a Phenomenex C18 (25 cm × 4.6 mm i.d.) column allowed us to sep. twelve flavonoids in medicinal plants and raw cosmetics with high resoln. and short anal. time.

Abstract

General method for determining flavonoids in medicinal plants and raw cosmetics using HPLC with a photodiode array detector. Wang, L.-H.; Li, W.-H. Department of Applied Chemistry, Chia Nan University of Pharmacy and Science, Tainan, Taiwan. Pharmaceutical Chemistry Journal (2007), 41(4), 225-231. Publisher: Springer, CODEN: PCJOAU ISSN: 0091-150X. Journal written in English. CAN 147:528473 AN 2007:1188035 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A flavonoid-based compd. is provided to show excellent antioxidative activity on low d. lipoprotein (LDL) and effectively inhibit the activity of acyl-CoA:cholesterol acyltransferase (ACAT), thereby being useful for preventing and treating cardiovascular diseases, such as hyperlipidemia, coronary heart disease, coronary sclerosis and myocardial infarction. The flavonoids are isolated from roots of Cudrania tricuspidata.

Abstract KR 2005-106992 20051109Priority Application KR 2007049812 A 20070514 KR 2005-106992 20051109 Patent No. Kind Date Application No. Date Patent Family Information

Flavonoids for the prevention and treatment of cardiovascular diseases. Jeong, Tae Sook; Lee, Woo Song; Park, Ki Hun; Lee, Byong Won; Park, Yong Dae; Kim, Min Jung; An, So Jin; Kim, Hyoung Chin; Moon, Og Sung; Won, Young Suk. (Korea Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2007), No pp. given. CODEN: KRXXA7 KR 2007049812 A 20070514 Patent written in Korean. Application: KR 2005-106992 20051109. Priority: . CAN 147:534664 AN 2007:1191195 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


unequivocal assignment of its 2R,3S abs. configuration. The exptl. obsd. Cotton effect (CE) around 290 nm is contributed by the acetophenone π → π* transition of the ABC-flavanone moiety and the electronic transition within the DEF-flavone moiety, while another diagnostic pos. CE around 350 nm is attributable to the electronic interaction between the ABC-flavanone moiety and the DEF-flavone moiety, as well as the electronic transition within the DEF-flavone moiety. The remarkable differences of the calcd. ECD of its two rotamers indicate that the rotational restrictions significantly affect the ECD of 3,8''-biflavonoids. Empirical ECD rules derived from monomeric flavonoids may not be applicable to configurational assignment of complex 3,8''-biflavonoids. This study has provided new insights in interpreting the exptl. obsd. ECD spectra of this class of compds.


flavanone

Answer 129:

The invention relates to a c-kit gene expression inhibitor characterized by contg. Oldenlandia diffusa ext., wherein the agent is suitable for use in a skin-whitening cosmetic. A c-kit gene expression inhibitor contg. Oldenlandia diffusa ext. with an antioxidant, an antiinflammatory agent, a macromol. component, and/or a polyhydric alc. is also disclosed. For example, the effect of Oldenlandia diffusa ext. on c-kit expression in human melanocyte with/without of other components was tested. Also, a cosmetic cream compn. contg. beeswax 2, stearyl alc. 5, stearic acid 8, squalane 10, self-emulsifying glyceryl monostearate 3, polyoxyethylene cetyl ether 1, sunflower seed ext. 2, 1,3-butylene glycol 5, Oldenlandia diffusa ext. 0.0001, KOH 0.3, preservative q.s., reduced NAD 0.1, and water balance to 100 % was formulated.

Abstract JP 2006-100618 20060331Priority Application JP 2007269752 A 20071018 JP 2006-100618 20060331 Patent No. Kind Date Application No. Date Patent Family Information

Skin compositions containing Oldenlandia diffusa extract. Yamada, Yasuhiro; Morita, Satoshi; Otake, Tetsuo. (Narisu Cosmetic Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2007), 11pp. CODEN: JKXXAF JP 2007269752 A 20071018 Patent written in Japanese. Application: JP 2006-100618 20060331. Priority: . CAN 147:433038 AN 2007:1173707 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The extn. and detn. of contents of the total flavanones of the leaves of Phyllostachyspubescens was investigated. Purely phys. process flow and spectrophotometry were used to ext. and check the flavanone of the leaves of Phyllostachyspubescens. By this method the contents of the total flavanone of the leaves of Phyllostachyspubescens was C = 1.56% and the recovery rate was 99.4%. This text provided the extn. and purifying methods to get the outcome and the purity of the flavanones was high. This method was a purely phys. process, and had not any chem. change and pollution. It was an ideal way to ext. the flavanone of the leaves of Phyllostachyspubescens.

Abstract

Extraction and determination of contents of the total flavanones of the leaves of phyllostachyspubescens. Huang, Suoyi; Yao, Xiaomin; Qin, Chengjian; Liang, Yu. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(7), 1228-1229. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:409749 AN 2007:1186398 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Based on the identification of actin as a target protein for the flavonol quercetin, the binding affinities of quercetin and structurally related flavonoids were detd. by flavonoid-dependent quenching of tryptophan fluorescence from actin. Irresp. of differences in the hydroxyl pattern, similar Kd values in the 20 μM range were obsd. for six flavonoids encompassing members of the flavonol, isoflavone, flavanone, and flavane group. The potential biol. relevance of the flavonoid/actin interaction in the cytoplasm and the

Abstract

Flavonoids affect actin functions in cytoplasm and nucleus. Boehl, Markus; Tietze, Simon; Sokoll, Andrea; Madathil, Sineej; Pfennig, Frank; Apostolakis, Joannis; Fahmy, Karim; Gutzeit, Herwig O. Institute of Zoology, Technical University Dresden, Dresden, Germany. Biophysical Journal (2007), 93(8), 2767-2780. Publisher: Biophysical Society, CODEN: BIOJAU ISSN: 0006-3495. Journal written in English. CAN 147:461595 AN 2007:1165363 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In order to make use of the resources of Folium artemisiae argyi, avoid wasting and approach the extn. of total flavanone of Folium Artemisiae Argyi. The flavonids were extd. by ethanol as the solvent from folium artemisiae argyi with ultrasonic wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of Folium Artemisiae Argyi. By this method getting the d. of the total flavanone of Folium Artemisiae Argyi is C=0.6599 mg/mL and the rate of recovery is 102.6 %. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone are all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone of Folium artemisiae argyi.

Abstract

Study on extraction process of the total flavanone of Guixi's Folium artemisiae argyi by ultrasonic wave. Lu, Hai-feng; Luo, Jian-hua; Zhang, Li-dan; Liu, Jiao; Meng, Chun-yue; Feng, Ling; Li, Lin; Huang, Suo-yi. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(5), 21-23. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. AN 2007:1170091 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


For fully using the resources of the Jasminum sambac air, the method that withdrawes the flavanone from the Jasminum sambac air was introduced by ultrasonic wave, and the method of distinct flavanone were elaborated, then the flavanone which withdrawed from the Jasminum sambac air were checked, and then combined to immerse with ethanol that withdraws the total flavonoid. This operation was simple, convenient, and pollution-free. The Jasminum sambac air has high development and utilization of high value.

Abstract

The total flavanone of the Jasminum sambac air extraction and the identification by ultrasonic wave. Luo, Jian-hua; Meng, Chun-yue; Zhang, Li-dan; Feng, Ling; Tan, Yong-ping; Huang, Suo-yi. Department of Clinical Medicine, Youjiang Medical College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(5), 49-50. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 148:27650 AN 2007:1170153 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 134:

This paper points out the usefulness of biopartitioning micellar chromatog. (BMC) using capillary columns as a high-throughput primary screening tool providing key information about the oral absorption, skin permeability, and brain-blood distribution coeffs. of 15 polyphenols (6 flavones, 2 flavonols, a flavanone, 2 flavan-3-ols, 3 phenolic acids, and a phloroglucinol) in a simple and economical way. For the compds. studied, except vicenin-2, rutin, chlorogenic acid, p-hydroxycinnamic acid, and 4-hydroxybenzoic acid, maximal oral absorption (>90%) can be expected, if there are not soly. problems or metabolic processes. On the other hand, the most retained compds. in BMC, i.e., 5-hydroxyflavone, flavone, and flavanone, show the highest brain-blood distribution coeffs. and skin permeability coeffs.

Abstract

Permeability Profile Estimation of Flavonoids and other Phenolic Compounds by Biopartitioning Micellar Capillary Chromatography. Diniz, Andrea; Escuder-Gilabert, Laura; Lopes, Norberto P.; Gobbo-Neto, Leonardo; Villanueva-Camanas, Rosa Maria; Sagrado, Salvador; Medina-Hernandez, Maria Jose. Departamento de Ciencias Farmaceticas, CCS, Universidade Estadual de Londrina, Londrina, PR, Brazil. Journal of Agricultural and Food Chemistry (2007), 55(21), 8372-8379. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 148:32200 AN 2007:1132951 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. In the early nineties the presence of flavonoids in Citrus juices began to attract the attention of a no. of researchers, as a result of their biol. and physiol. importance. This short review will explore 2 different aspects. The first part will focus on anal. techniques for the characterization of juices from different Citrus fruits regarding their flavonoid content (even if present in only trace amts.), concg. on the most widely used methods (LC-MS and LC-MS-MS). The second part analyzes data reported in the literature regarding the compn. of Citrus juices. The main components that were detected so far are flavanone-O-glycosides and flavone-O- or -C-glycosides. The presence of such derivs. in various hand-squeezed and industrial juices is discussed, with special emphasis on their correlation to different species.

Abstract

Flavonoid composition of Citrus juices. Gattuso, Giuseppe; Barreca, Davide; Gargiulli, Claudia; Leuzzi, Ugo; Caristi, Corrado. Dipartimento di Chimica Organica e Biologica, Universita di Messina, Messina, Italy. Molecules (2007), 12(8), 1641-1673. Publisher: Molecular Diversity Preservation International, CODEN: MOLEFW ISSN: 1420-3049. http://www.mdpi.org/molecules/papers/12081641.pdf Journal; General Review; Online Computer File written in English. CAN 147:404991 AN 2007:1154642 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


nucleus was addressed using an actin polymn. and a transcription assay, resp. In contrast to the similar binding affinities, the flavonoids exert distinct and partially opposing biol. effects: although flavonols inhibit actin functions, the structurally related flavane epigallocatechin promotes actin activity in both test systems. IR spectroscopic evidence reveals flavonoid-specific conformational changes in actin which may mediate the different biol. effects. Docking studies provide models of flavonoid binding to the known small mol.-binding sites in actin. Among these, the mostly hydrophobic tetramethylrhodamine-binding site is a prime candidate for flavonoid binding and rationalizes the high efficiency of quenching of the two closely located fluorescent tryptophans. The exptl. and theor. data consistently indicate the importance of hydrophobic, rather than H-bond-mediated, actin-flavonoid interactions. Depending on the rigidity of the flavonoid structures, different functionally relevant conformational changes are evoked through an induced fit.


flavanone


Xanthohumol (XN), the chalcone from beer hops has several biol. activities. XN has been shown to induce apoptosis in cancer cells and also has been reported to be involved in lipid metab. Based on these studies and our previous work with natural compds., we hypothesized that XN and its isomeric flavanone, isoxanthohumol (IXN), would induce apoptosis in adipocytes through the mitochondrial pathway and would inhibit maturation of preadipocytes. Adipocytes were treated with various concns. of XN or IXN. In mature adipocytes both XN and IXN decreased viability, increased apoptosis and increased ROS prodn., XN being more effective. Furthermore, the antioxidants ascorbic acid and 2-mercaptoethanol prevented XN and IXN-induced ROS generation and apoptosis. Immunoblotting anal. showed an increase in the levels of cytoplasmic cytochrome c and cleaved poly (ADP-ribose) polymerase (PARP) by XN and IXN. Concomitantly, we obsd. activation of the effectors caspase-3/7. In maturing preadipocytes both XN and IXN were effective in reducing lipid content, XN being more potent. Moreover, the major adipocyte marker proteins such as PPARγ, C/EBPα, and aP2 decreased after treatment with XN during the maturation period and that of DGAT1 decreased after treatment with XN and IXN. Taken together, our data indicate that both XN and IXN inhibit differentiation of preadipocytes, and induce apoptosis in mature adipocytes, but XN is more potent.

Abstract

Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Yang, Jeong-Yeh; Della-Fera, Mary Anne; Rayalam, Srujana; Baile, Clifton A. Department of Animal and Dairy Science 444 Edgar L. Rhodes Center for Animal and Dairy Science, University of Georgia, Athens, GA, USA. Apoptosis (2007), 12(11), 1953-1963. Publisher: Springer, CODEN: APOPFN ISSN: 1360-8185. Journal written in English. CAN 148:206423 AN 2007:1108444 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Among 3 species of polygonaceous feeding leaf beetle, Galerucella grisescens, Gallerucida bifasciata, and Gastrophysa atrocyanea, only G. bifasciata did not use a polygonaceous plant, P. lapathifolia, as a food. 2nd and 3rd instar larvae and adults of G. bifasciata fed on the leaves; however, the feeding amt. decreased day by day and all died. The 1st instar larvae hardly fed on the leaves and all larvae died. Biol. tests and chem. anal. revealed that feeding deterrents were present in P. lapathifolia leaves. A feeding deterrent was isolated and identified as 3-hydroxy-5-methoxy-6,7-methylenedioxy flavanone. The compd. deterred 1st instar larvae of G. bifaciata from feeding and significantly lessened the survival rate of the larvae at concns. >1.0 mg/mL. Larvae of G. grisescens were not deterred from feeding by the compd. at 5 mg/mL. The presence of other fractions increased the feeding deterrent activity of the compd. to 1st instar larvae of G. bifasciata. These results revealed that P. lapathifolia leaves contain multiple feeding deterrents to G. bifasciata.

Abstract

A feeding deterrent from Persicaria lapathifolia (polygonaceae) leaves to larvae of Gallerucida bifasciata (coleoptera: chrysomelidae). Abe, Makoto; Niizeki, Masatsugu; Matsuda, Kazuhiro. Laboratory of Insect Science and Bioregulation, Graduate School of Agriculture, Tohoku University, Miyagi, Japan. Applied Entomology and Zoology (2007), 42(3), 449-456. Publisher: Japanese Society of Applied Entomology and Zoology, CODEN: APEZAW ISSN: 0003-6862. Journal written in English. AN 2007:1127523 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Two novel antibacterial flavonoids from Myrsine africana L. Kang, Lu; Zhou, Jian-Xia; Shen, Zheng-Wu. School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai, Peop. Rep. China. Chinese Journal of Chemistry (2007), 25(9), 1323-1325. Publisher: Shanghai Institute of Organic Chemistry, CODEN: CJOCEV ISSN: 1001-604X. Journal written in English. CAN 148:280234 AN 2007:1093325 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The major active biol. constituents in Citrus herbs are flavonoids, esp. hesperidin, naringin and alkaloids, mainly synephrine, with beneficial medical effects on human health. They are used as the markers to control the quality of Citrus herbs. In this paper, a new ion pairing chromatog. method was developed to exclude the most polar solute (synephrine) from the viod vol. and to maintain selectivity between the two other solutes (hesperidin and naringin). Perfluorinated carboxylic acids, which are appropriate for MS detection due to their volatility, were used as ion-pairing agents. The problems of the synephrine sepn., such as band tailing and low retention, were solved successfully by using perfluorinated carboxylic acids. The effect of heptafluorobutyric acid (HFBA) was the best in the three investigated perfluorinated carboxylic acids. For the flavanone glycosides, the influence of the perfluorinated acids on retention time was rather weak. The 2 different kinds of the analytes were sepd. satisfactorily in one run using an isocratic eluent and the total anal. time takes less than 10 min. The abundance of pseudomol. ions was recorded using selected ion monitoring (SIM) mode of m/z 135.1, 273.1 and 303.1 for synephrine, naringin and hesperidin, resp. The contents of hesperidin, naringin and synephrine in several Citrus herbs were simultaneously detd. by the proposed method.

Abstract

Simultaneous determination of flavonoid and alkaloid compounds in Citrus herbs by high-performance liquid chromatography-photodiode array detection-electrospray mass spectrometry. Ding, Li; Luo, Xubiao; Tang, Fei; Yuan, Jinbin; Liu, Qian; Yao, Shouzhuo. College of Chemistry and Chemical Engineering, Hunan University, Changsha, Peop. Rep. China. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2007), 857(2), 202-209. Publisher: Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal written in English. CAN 147:455781 AN 2007:1106828 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two flavindogenides, 3-(4-methoxybenzylidene)- and 3-(3,4-dimethoxybenzylidene)-2-(4-methoxyphenyl)flavanone are reacted with 5-substituted 2-aminobenzenethiols (the substituents being Br, Cl, F, Me, MeO, or EtO) to give 10-substituted 6-(4-methoxyphenyl)-6H-6a,7-dihydro-7-(4-methoxyphenyl/3,4-dimethoxyphenyl)[1]benzopyrano[3,4-c][1,5]benzothiazepines in 55-67% yields. The products are characterized on the basis of anal. and spectral data. The synthesized compds. are screened for antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Candida albicans. All the methoxy-substituted benzopyranobenzothiazepines showed moderate to comparable activity (using gatifloxin, natilmicin as ref. std.) against gram-pos. and gram-neg. bacteria. They also showed antifungal activity (compared to fluconazole), with the compd. having the max. no. of MeO groups having the max. activity, while the fluoro compds. are completely inactive.

Abstract

Syntheses of 1,5-benzothiazepines: Part XXXIII. Syntheses and antimicrobial studies of 10-substituted-6-(4-methoxyphenyl)-6H-6a,7-dihydro-7-(4-methoxyphenyl/3,4-dimethoxyphenyl)[1]benzopyrano[3,4-c][1,5]benzothiazepines. Pant, Seema; Sharma, Priyanka; Sharma, B. S.; Pant, Umesh C. LBS Government P.G. College, Jaipur, India. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2007), 46B(9), 1537-1544. Publisher: National Institute of Science Communication and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. AN 2007:1107647 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Bio-guided fractionation of the exts. from leaves of Piper mollicomum and Piper lhotzkyanum against the fungi Cladosporium cladosporioides and C. sphaerospermum afforded seven bioactive compds., four being chromenes: Me 2,2-dimethyl-2H-chromene-6-carboxylate, Me 8-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylate, 2-methyl-2-[4'-methyl-3'-pentenyl]-2H-1-benzopyran-6-carboxylic acid, 2,2-dimethyl-2H-chromene-6-carboxylic acid, one a dihydrochalcone: 2',6'-dihydroxy-4'-methoxydihydrochalcone, and two flavanones: 7-methoxy-5,4'-dihydroxy-flavanone and 7,4'-dimethoxy-5-hydroxy-flavanone. The structures of the bioactive isolated derivs. were elucidated by interpretation of their NMR data [1H and 13C (BBD, DEPT 135°)], and mass spectral data as well as by comparison with data described in the literature.

Abstract

Antifungal derivatives from Piper mollicomum and P. lhotzkyanum (Piperaceae). Lago, Joao Henrique G.; Young, Maria Claudia M.; Reigada, Juliana B.; Soares, Marisi G.; Roesler, Bianca P.; Kato, Massuo J. Centro de Ciencias e Humanidades, Universidade Presbiteriana Mackenzie, Sao Paulo, Brazil. Quimica Nova (2007), 30(5), 1222-1224. Publisher: Sociedade Brasileira de Quimica, CODEN: QUNODK ISSN: 0100-4042. Journal written in English. CAN 148:398405 AN 2007:1064504 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The patent relates to the application of liquiritigenin to manufg. the medicines for preventing and treating lung cancer, liver cancer, gastric cancer, colon cancer, etc. Liquiritigenin is flavanone deriv.


Application of liquiritigenin to manufacturing medicines for preventing and treating cancer. Cai, Yunqing. (Nanjing Medical University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp. CODEN: CNXXEV CN 101036638 A 20070919 Patent written in Chinese. Application: CN 1003-8887 20060316. Priority: . CAN 147:398635 AN 2007:1072018 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two novel flavonoids, myrsininone A (1), an isoflavone and myrsininone B (2), a flavanone, with very strong antibacterial activities, were isolated from the stems of Myrsine africana L. Their structures were elucidated by extensive spectroscopic analyses. The antibacterial activities were detd. by modified Resazuric MIC methods.

Abstract


flavanone

To study the chem. constituents in the leaves of Mallotus apelta. Constituents isolation and purifn. were carried out on silica gel and polyamide column. Their structures were identified by physicochem. properties and spectral anal. Five compds. were isolated and

Abstract

Isopentenyl flavanone from Mallotus apelta. Wu, Gui-fan; Wei, Song; Lan, Shu-bin; Xu, Xue-jian. Department of Pharmacy, Guangxi College of Traditional Chinese Medicine, Nanning, Peop. Rep. China. Zhongcaoyao (2006), 37(8), 1126-1128. Publisher: Zhongcaoyao Zazhi Bianjibu, CODEN: CTYAD8 ISSN: 0253-2670. Journal written in Chinese. CAN 148:198232 AN 2007:1040007 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Anthocyanins are important secondary metabolites in plants, which are involved in many functions. The white peel of an enlarged root in 'Tsuda' plants turned red after irradiated with UV-A light for 48h, but remained white when held in the dark. Red earthnuts and white peels were hybridized with cDNA microarray made by unique gene fragments of subtraction library. The expression of 81 genes were up-regulated including cytochrome P 450, PAL, F3H, ANS, CHS, DFR, and GST gene fragments related to anthocyanidin biosynthesis. The expression of 47 genes was down-regulated after irradiated with UV-A light. The northern blotting results showed that the expression of PAL, CHS, F3H, DFR, and ANS in red root peels was more in 'Tsuda' turnip after irradn. with UV-A light than in white ones held in a dark condition. The results of northern blotting verified the reliability of cDNA microarray.

Abstract

Screening the genes associated with anthocyanin biosynthesis in roots of 'Tsuda' turnip using cDNA microarray. Xu, Zhi-Ru; Li, Yu-Hua. Life Science College, Northeast Forestry University, Harbin, Peop. Rep. China. Yichuan (2006), 28(9), 1101-1106. Publisher: Kexue Chubanshe, CODEN: ICHUDW ISSN: 0253-9772. Journal written in Chinese. CAN 148:234049 AN 2007:1050088 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The content of the content of total flavone in cultivated Glycyrrhiza uralensis was detd. by colorimetry by using character of flavanone translated into chalcone under alk. condition of 10% KOH soln. The linear regression equation was Y = 21.323X-0.0923 (r = 0.9994), and the linear range was 4.9-98.0 μg/mL. The av. recovery was 98.7%, and RSD was 1.9% (n = 5). There was large difference of the total flavone content from different localities, and the difference was not significant with different ages. The method is sensitive, convenient, and accurate.

Abstract

Determination of the content of total flavone in cultivated Glycyrrhiza uralensis. Yan, Yonghong; Wang, Wenquan; Yang, Na. School of Chinese Materia Medica, Beijing University of Chinese Medicine, Beijing, Peop. Rep. China. Zhongguo Zhongyao Zazhi (2006), 31(12), 1019-1021. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese. CAN 147:455760 AN 2007:1055108 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Background Fruit coloration of red-skinned grapevines is mainly due to anthocyanin pigments. We analyzed a panel of nine cultivars that included extreme phenotypes for berry color, ranging from green (absence of anthocyanins) to red, purple, violet and blue. Expression of six genes of the anthocyanin pathway coding for flavanone-hydroxylase (F3H), flavonoid 3'-hydroxylase (F3'H), flavonoid 3',5'-hydroxylase (F3'5'H), UDP-glucose:flavonoid-3-O-glucosyltransferase (UFGT), glutathione-S-transferase (GST), O-methyltransferase (OMT) and four transcription factors (MybA, MybB, MybC, MybD) was analyzed by quant. RT-PCR at four developmental stages from before the onset of ripening until full maturity and compared to anthocyanin metabolites. Results Total anthocyanin content at full maturity correlated well with the cumulative expression of F3H, UFGT and GST throughout ripening. Transcripts of the last two genes were absent in the green-skinned cultivar 'Sauvignonasse', also known as 'Tocai friulano', and were at least 10-fold less abundant in pale red cultivars, such as 'Pinot gris' and 'Gewurztraminer', compared to fully colored cultivars. Predominance of tri-hydroxylated anthocyanins (delphinidin, petunidin and malvidin) in cultivars bearing dark berries with violet and blue hue was assocd. with higher ratios of F3'5'H/F3'H transcription, compared to redskinned cultivars. Higher levels of OMT transcripts were obsd. in berries of cultivars that accumulated methoxylated forms of anthocyanins more abundantly than non-methoxylated forms. Conclusions Color variation of the grape berry conforms to a peculiar pattern of genotype-specific expression of the whole set of anthocyanin genes in a direct transcript-metabolite-phenotype relationship. Cumulative mRNA levels of the structural genes and

Abstract

Transcriptional control of anthocyanin biosynthetic genes in extreme phenotypes for berry pigmentation of naturally occurring grapevines. Castellarin, Simone D.; Di Gaspero, Gabriele. Instituto di Genomica Applicata, Parco Scientifico e Tecnologico Luigi Danieli, Udine, Italy. BMC Plant Biology (2007), 7 No pp. given. Publisher: BioMed Central Ltd., CODEN: BPBMAN ISSN: 1471-2229. http://www.biomedcentral.com/content/pdf/1471-2229-7-46.pdf Journal; Online Computer File written in English. AN 2007:1026455 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The daily intake of food flavonoids was detd. using a semiquant. food frequency questionnaire (FFQ) and a four day non consecutive food diary (4DFR) in a group of 45 female Flemish dietitians. The subjects were asked to report their food intake three times: day 1 using the FFQ (FFQ1); between day 2 and 13 using a four day non consecutive food diary (4DFR); and again the FFQ on day 14 (FFQ2). The total flavonoid intake in mg/day as estd. with the different methods were resp. (mean and SD) for FFQ1 166.0 ± 146.6 mg/day; for 4DFR 203.0 ± 243.2 mg/day; and for FFQ2 158.3 ± 151.8 mg/day. There was a significant different est. for the amt. of flavan-3-ols, flavanones and flavones when comparing the two FFQs with the 4DFR. The two research methods classified 88% of the 45 dietitians in the same or in an adjacent quartile for total flavonoid intake. The findings of this study indicate that the developed FFQ seems to be a simple and reliable method to assign subjects in quartiles of flavonoid intake.

Abstract

Estimation of daily human intake of food flavonoids. Mullie, P.; Clarys, P.; Deriemaeker, P.; Hebbelinck, M. Faculty of Physical Education and Physiotherapy, Department of Human Biometry and Biomechanics, Vrije Universiteit Brussel (VUB), Brussels, Belg. Plant Foods for Human Nutrition (New York, NY, United States) (2007), 62(3), 93-98. Publisher: Springer, CODEN: PFHNE8 ISSN: 0921-9668. Journal written in English. CAN 148:167875 AN 2007:1027502 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


elucidated as taraxerol (I), β-sitosterol (II), 5,7-dihydroxy-6-isopentenyl-4'-methoxy-flavanone (III), apigenin (IV), and apigenin-7-O-β-D-glucoside (V). Compd. III is a new compd. named as mallotusin. Compds. I and III-V are isolated from the leaves of M. apelta for the first time.


flavanone


Brain function improvers containing flavanones and their compositions. Fukumoto, Shuichi; Okada, Miki; Uchida, Koji; Shibata, Takahiro; Nakahara, Hiroko; Kita, Narumi; Yokogoshi, Hidehiko. (Pokka Corp., Japan). Jpn. Kokai Tokkyo Koho (2007), 12pp. CODEN: JKXXAF JP 2007230878 A 20070913 Patent written in Japanese. Application: JP 2006-51013 20060227. Priority: . CAN 147:343089 AN 2007:1024193 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Background: The recent discoveries of transposable elements carrying host gene fragments such as the Pack-MULEs (Mutator-like transposable elements) of maize (Zea mays), rice (Oryza sativa) and Arabidopsis thaliana, the Helitrons of maize and the Tgm-Express of soybeans, revealed a widespread genetic mechanism with the potential to rearrange genomes and create novel chimeric genes affecting genomic and proteomic diversity. Not much is known with regard to the mechanisms of gene fragment capture by those transposon elements or the expression of the captured host gene fragments. There is some evidence that chimeric transcripts can be assembled and exist in EST collections. Results: We report results obtained from anal. of RT-PCR derived cDNAs of the Glycine max mutant flower color gene, wp, that contains a 5.7-kb transposon (Tgm-Express1) in Intron 2 of the flavanone 3-hydroxylase gene (F3H) and is composed of five unrelated host gene fragments. The collection of cDNAs derived from the wp allele represents a multiplicity of processed RNAs varying in length and sequence that includes some identical to the correctly processed mature F3H transcript with three properly spliced exons. Surprisingly, the five gene fragments carried by the Tgm-Express1 were processed through complex alternative splicing as addnl. exons of the wp transcript. Conclusion: The gene fragments carried by the Tgm inverted repeat ends appear to be retained as functional exons/introns within the element. The spliceosomes then select indiscriminately the canonical intron splice sites from a pre-mRNA to assemble diverse chimeric transcripts from the exons contained in the wp allele. The multiplicity and randomness of these events provide some insights into the origin and mechanism of alternatively spliced genes.

Abstract

Novel exon combinations generated by alternative splicing of gene fragments mobilized by a CACTA transposon in Glycine max. Zabala, Gracia; Vodkin, Lila. Department of Crop Sciences, University of Illinois, Urbana, IL, USA. BMC Plant Biology (2007), 7 No pp. given. Publisher: BioMed Central Ltd., CODEN: BPBMAN ISSN: 1471-2229. http://www.biomedcentral.com/content/pdf/1471-2229-7-38.pdf Journal; Online Computer File written in English. CAN 147:336888 AN 2007:1026447 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


their relative abundance throughout ripening explained per se the final phenotype for anthocyanin content, anthocyanin compn., color intensity and color hue of grapes at berry maturity.


flavanone

Purpose: ATP-binding cassette (ABC) transporters, such as P-glycoprotein (P-gp), breast cancer resistance protein (BCRP), and multidrug resistance-related protein 1 (MRP1), confer resistance to various anticancer agents. We previously reported that some flavonoids have BCRP-inhibitory activity. Here we show the reversal effects of an extensive panel of flavonoids upon BCRP-, P-gp-, and MRP1-mediated drug resistance. Methods: Reversal effects of flavonoids upon BCRP-, P-gp-, or MRP1-mediated drug resistance were examd. in the BCRP- or MDR1-transduced human leukemia K562 cells or in the MRP1-transfected human epidermoid carcinoma KB-3-1 cells using cell growth inhibition assays. The IC50 values were detd. from the growth inhibition curves. The RI50 values were then detd. as the concn. of inhibitor that causes a twofold redn. of the IC50 in each transfectant. The reversal of BCRP activity was tested by measuring the fluorescence of intracellular topotecan. Results: The BCRP-inhibitory activity of 32 compds. was screened, and 20 were found to be active. Among these active compds., 3',4',7-trimethoxyflavone showed the strongest anti-BCRP activity with

Abstract

Flavonoids inhibit breast cancer resistance protein-mediated drug resistance: transporter specificity and structure-activity relationship. Katayama, Kazuhiro; Masuyama, Kazuto; Yoshioka, Sho; Hasegawa, Hitomi; Mitsuhashi, Junko; Sugimoto, Yoshikazu. Department of Chemotherapy, Kyoritsu University of Pharmacy, Tokyo, Japan. Cancer Chemotherapy and Pharmacology (2007), 60(6), 789-797. Publisher: Springer, CODEN: CCPHDZ ISSN: 0344-5704. Journal written in English. CAN 148:135221 AN 2007:1019824 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The human secretory phospholipase A2 group IIA (PLA2-IIA) is a lipolytic enzyme. Its inhibition leads to a decrease in eicosanoids levels and, thereby, to reduced inflammation. Therefore, PLA2-IIA is of high pharmacol. interest in treatment of chronic diseases such as asthma and rheumatoid arthritis. Quercetin and naringenin, amongst other flavonoids, are known for their anti-inflammatory activity by modulation of enzymes of the arachidonic acid cascade. However, the mechanism by which flavonoids inhibit Phospholipase A2 (PLA2) remained unclear so far. Flavonoids are widely produced in plant tissues and, thereby, suitable targets for pharmaceutical extns. and chem. syntheses. Our work focuses on understanding the binding modes of flavonoids to PLA2, their inhibition mechanism and the rationale to modify them to obtain potent and specific inhibitors. Our computational and exptl. studies focused on a set of 24 compds. including natural flavonoids and naringenin-based derivs. Exptl. results on PLA2-inhibition showed good inhibitory activity for quercetin, kaempferol, and galangin, but relatively poor for naringenin. Several naringenin derivs. were synthesized and tested for affinity and inhibitory activity improvement. 6-(1,1-dimethylallyl)naringenin revealed comparable PLA2 inhibition to quercetin-like compds. We characterized the binding mode of these compds. and the determinants for their affinity, selectivity, and inhibitory potency. Based on our results, we suggest C(6) as the most promising position of the flavonoid scaffold to introduce chem. modifications to improve affinity, selectivity, and inhibition of PLA2-IIA by flavonoids.

Abstract

Mechanism of inhibition of human secretory phospholipase A2 by flavonoids: rationale for lead design. Laettig, Jens; Boehl, Markus; Fischer, Petra; Tischer, Sandra; Tietboehl, Claudia; Menschikowski, Mario; Gutzeit, Herwig O.; Metz, Peter; Pisabarro, M. Teresa. Structural Bioinformatics, BIOTEC TU Dresden, Dresden, Germany. Journal of Computer-Aided Molecular Design (2007), 21(8), 473-483. Publisher: Springer, CODEN: JCADEQ ISSN: 0920-654X. Journal written in English. CAN 148:253340 AN 2007:1023827 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Title improvers and compns., useful for beverages, foods, pharmaceuticals, or feeds, contain eriodictyol (I), hesperetin, naringenin, eriocitrin and/or hesperidin as active ingredients. Thus, I at 15 μM enhanced NGF-induced neurite elongation in PC12 cells by 50.28%. I at 1 mg/kg p.o. also improved scopolamine-induced learning disorder in rats.


flavanone

Flavonoids are a large family of polyphenolic compds. with manifold functions in plants. Present in a wide range of vegetables and fruits, flavonoids form an integral part of the human diet and confer multiple health benefits. Here, the authors report on metabolic engineering of the flavonoid biosynthetic pathways in apple (Malus domestica Borkh.) by overexpression of the maize (Zea mays L.) leaf color (Lc) regulatory gene. The Lc gene was transferred into the M. domestica cultivar Holsteiner Cox via Agrobacterium tumefaciens-mediated transformation which resulted in enhanced anthocyanin accumulation in regenerated shoots. Five independent Lc lines were investigated for integration of Lc into the plant genome by Southern blot and PCR analyses. The Lc-transgenic lines contained one or two Lc gene copies and showed increased mRNA levels for phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS), flavanone 3 beta-hydroxylase (FHT), dihydroflavonol 4-reductase (DFR), leucoanthocyanidin reductases (LAR), anthocyanidin

Abstract

Maize Lc transcription factor enhances biosynthesis of anthocyanins, distinct proanthocyanidins and phenylpropanoids in apple (Malus domestica Borkh.). Li, Houhua; Flachowsky, Henryk; Fischer, Thilo C.; Hanke, Magda-Viola; Forkmann, Gert; Treutter, Dieter; Schwab, Wilfried; Hoffmann, Thomas; Szankowski, Iris. Institute of Biological Production Systems, Fruit Science Section, Leibniz University of Hannover, Hannover, Germany. Planta (2007), 226(5), 1243-1254. Publisher: Springer, CODEN: PLANAB ISSN: 0032-0935. Journal written in English. CAN 148:74166 AN 2007:1010348 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effects of isoflavones and of a deriv. of soybeans fermented with Bacillus subtilis, designated Nattoesse, on the lipopolysaccharide (LPS)-induced prodn. of tumor necrosis factor-α (TNF-α) and fibrinolysis were investigated in vivo. The dietary supplement Nattoesse contains several isoflavones. Therefore, we examd. the effects of individual isoflavones (daidzein, daidzin, genistein, and genistin) on the LPS-induced prodn. of TNF-α. I.p. injections of daidzein, daidzin, and genistin (but not of genistein before a challenge with LPS) resulted in significant depression of serum levels of TNF-α in mice. Daidzein had the strongest activity in this assay. Oral administration of daidzein to mice also had a significant suppressive effect, as compared with that of the Citrus flavanone naringin. In galactosamine-sensitized mice, by contrast, the suppression of LPS-induced lethal shock by daidzein was very weak. Nattoesse did not inhibit the prodn. of TNF-α nor did it prevent lethal shock. However, oral administration of Nattoesse to mice significantly suppressed LPS-induced increases in scores of the fibrin degrdn. product, and the effect was both dose- and time-dependent. Thus, it appears that Nattoesse has fibrinolytic activity during LPS-induced circulatory failure.

Abstract

Effects of Isoflavones and Soybeans Fermented with Bacillus subtilis on Lipopolysaccharide-Induced Production of Tumor Necrosis Factor-α and Fibrinolysis In Vivo. Hasumuma, Ryoichi; Kawaguchi, Kiichiro; Kikuchi, Sei-ichi; Sugiyama, Tsuyoshi; Kumazawa, Yoshio. Department of Biosciences, School of Science and Graduate School of Fundamental Life Science, Kitasato University, Sagamihara, Japan. Immunopharmacology and Immunotoxicology (2007), 29(2), 323-333. Publisher: Informa Healthcare, CODEN: IITOEF ISSN: 0892-3973. Journal written in English. CAN 148:159402 AN 2007:1012408 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


RI50 values of 0.012 μM for SN-38 and 0.044 μM for mitoxantrone. We next examd. the effects of a panel of 11 compds. on P-gp- and MRP1-mediated drug resistance. Two of the flavones, 3',4',7-trimethoxyflavone and acacetin, showed only low anti-P-gp activity, with the remainder displaying no suppressive effects against P-gp. None of the flavonoids that we tested inhibited MRP1. Conclusion: Our present results thus indicate that many flavonoids selectively inhibit BCRP only. Moreover, we examd. the structure-BCRP inhibitory activity relationship from our current study.


flavanone

The death of nigral neurons in Parkinson's disease is thought to involve the formation of the endogenous neurotoxin, 5-S-cysteinyl-dopamine. In the present study, we show that the polyphenols, (+)-catechin and caffeic acid, which contain a catechol moiety, inhibit tyrosinase-induced formation of 5-S-cysteinyl-dopamine via their capacity to undergo tyrosinase-induced oxidn. to yield cysteinyl-polyphenol adducts. In contrast, the inhibition afforded by the flavanone, hesperetin, was not accompanied by the formation of cysteinyl-hesperetin adducts, indicating that it may inhibit via direct interaction with tyrosinase. While the stilbene resveratrol also inhibited 5-S-cysteinyl-dopamine formation, this was accompanied by the formation of dihydrobenzothiazine, a strong neurotoxin. Our data indicate that the inhibitory effects of polyphenols against 5-S-cysteinyl-dopamine formation are structure-dependent and shed

Abstract

Inhibition of the formation of the neurotoxin 5-S-cysteinyl-dopamine by polyphenols. Vauzour, David; Vafeiadou, Katerina; Spencer, Jeremy P. E. Molecular Nutrition Group, School of Chemistry, Food and Pharmacy, University of Reading, Reading, UK. Biochemical and Biophysical Research Communications (2007), 362(2), 340-346. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 147:336135 AN 2007:996490 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The flavanone naringenin is known to possess only weak estrogenic properties, but some of its derivs. such as 8-prenylnaringenin are potent phytoestrogens. The aim of this study was to further clarify structure-function relationships of flavanones regarding their estrogenic or antiestrogenic properties by characterizing the new chem. synthesized naringenin deriv. 7-(O-prenyl)naringenin-4'-acetate (7-O-PN). A yeast based reporter gene assay and MVLN cells, a MCF-7-derived cell line that possesses a luciferase reporter gene under the control of a vitellogenin estrogen responsive element, were used to investigate estrogenic actions of 7-O-PN in vitro. Estradiol (E2) has been used as a pos. control. Subsequently a 3-day rat uterotrophic assay was performed to test for estrogenic effects. In addn., mRNA expression of estrogen-sensitive genes in the uteri of these rats was measured using real time rtPCR. While E2 leads to a strong dose-dependent signal in the yeast based reporter gene assay and in MVLN cells, 7-O-PN shows mild E2 antagonistic properties at concns. 10-8 and 10-7 M, E2 agonistic properties at 10-6 and 10-5 M in MVLN cells and no effects on the yeast based system. In contrast to E2 treatment, 7-O-PN treatment did not increase uterus wet wt. compared to the neg. control. These findings are supported by mRNA expression studies of proliferation markers. Addnl., mRNA expression studies of estrogen-regulated genes revealed very strong antiestrogenic properties of 7-O-PN regarding regulation of complement C3 expression while some estrogenic effects could be obsd. on the expression of estrogen receptor β, clusterin and possibly on progesterone receptor and vascular endothelial growth factor.

Abstract

Effects of the chemically synthesized flavanone 7-(O-prenyl)naringenin-4'-acetate on the estrogen signaling pathway in vivo and in vitro. Kretzschmar, Georg; Vollmer, Guenter; Schwab, Pia; Tischer, Sandra; Metz, Peter; Zierau, Oliver. Institut fuer Zoologie, Technische Universitaet Dresden, Dresden, Germany. Journal of Steroid Biochemistry and Molecular Biology (2007), 107(1-2), 114-119. Publisher: Elsevier Ltd., CODEN: JSBBEZ ISSN: 0960-0760. Journal written in English. CAN 148:1267 AN 2007:1010198 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


synthase (ANS) and anthocyanidin reductase (ANR). HPLC-DAD and LC-MS analyses revealed higher levels of the anthocyanin idaein (12-fold), the flavan 3-ol epicatechin (14-fold), and esp. the isomeric catechin (41-fold), and some distinct dimeric proanthocyanidins (7 to 134-fold) in leaf tissues of Lc-transgenic lines. The levels of phenylpropanoids and their derivs. were only slightly increased. Thus, Lc overexpression in Malus domestica resulted in enhanced biosynthesis of specific flavonoid classes, which play important roles in both phytopathol. and human health.


flavanone

Purification and determination of flavonoids in Radix Glycyrrhizae. Li, Jun-song; Xu, De-sheng; Feng, Yi; Chen, Li-hua. Shanghai University of Traditional Chinese Medicine, Shanghai, Peop. Rep. China. Zhongchengyao (2007), 29(7), 997-1000.


Aim: In order to make use of the resources of longan leaves, avoid wasting and approach the extn. of total flavanone of longan leaves. Methods: The flavonoids were extd. from longan leaves by ultrasonic wave with ethanol as the solvent. Using spectrophotometry to ext. and check the flavanone of longan leaves. Results: By this method, the obtained total flavanone of longan leaves is 1.0571 mg/mL and the rate of recovery is 101.3%. Conclusion: This method is a purely phys. process and has not any pollution, and it is an ideal way to ext. the flavanone of longan leaves.

Abstract

Ultrasonic extraction and identification of total flavanone from longan leaves. Lu, Hai-feng; Zhao, Jin; Li, Lin; Huang, Suo-yi; Li, Wei-bin; Yang, Wen-hui. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(4), 48-49. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 147:405063 AN 2007:967923 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Juices from fifteen citrus varieties (seven mandarins, four sweet oranges, one lemon, one grapefruit, and two pummeloes) of China were investigated mainly on quality parameters, total carotenoid, phenolic compds. (total phenolics, flavanone glycosides (FGs), and phenolic acids), and antioxidant capacity (ferric reducing antioxidant power (FRAP) assay and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay). Among the fifteen varieties, Bendizao had the highest content of total carotenoid (10.02 mg/L), Satsuma had the highest content of narirutin (288.12 mg/L), Yinzaocheng had the highest content of hesperidin (533.64 mg/L), and Huyou had the highest content of naringin (348.53 mg/L), neohesperidin (265.25 mg/L) and total FGs (746.08 mg/L). As for total phenolic acids, Liubencheng had the highest content (72.61 mg/L). Hybrid 439 achieved the highest AA content (631.25 mg/L), and the highest total phenolics (1555.49 mg/L) and the greatest inhibition of DPPH radical (61.62%). Hamlin had the highest ascorbic acid equiv. antioxidant capacity (AEAC: 899.31 mg/L) detd. by FRAP assay. Correlation coeffs. of AA, total phenolics (gallic acid equiv.), FRAP (AEAC), DPPH (I%), total FGs and total phenolic acids indicated that AA played a major role for the antioxidant capacity of citrus juices, and phenolics also played an important role, which may be mainly ascribed to FGs, while phenolic acids seemed to play a minimal role. Furthermore, Huyou and Hybrid 439 were considered two valuable varieties from the view of antioxidant capacity and nutrition.

Abstract

Juice components and antioxidant capacity of citrus varieties cultivated in China. Xu, Guihua; Liu, Donghong; Chen, Jianchu; Ye, Xingqian; Ma, Yaqin; Shi, John. Department of Food Science and Nutrition, Zhejiang University, Hangzhou, Peop. Rep. China. Food Chemistry (2007), Volume Date 2008, 106(2), 545-551. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 147:540670 AN 2007:978994 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


further light on the mechanisms by which polyphenols exert protection against neuronal injury relevant to neurodegenerative diseases.


flavanone

The antiproliferative activity of fresh fruit juices extd. from Citrus sinensis (cv. Washington Navel and cv. Sanguinello), C. deliciosa cv. Avana, C. clementina cv. Nules, C. aurantium subsp. myrtifolia , was evaluated against K562 (human chronic myelogenous leukemia), HL-60 (human leukemia) and MCF-7 (human breast adenocarcinoma) cell lines. All the juices tested showed antiproliferative

Abstract

Antiproliferative activity of Citrus juices and HPLC evaluation of their flavonoid composition. Camarda, Lorenzo; Di Stefano, Vita; Del Bosco, Sergio Fatta; Schillaci, Domenico. Dipartimento di Chimica e Tecnologie Farmaceutiche, Universita degli Studi di Palermo, Palermo, Italy. Fitoterapia (2007), 78(6), 426-429. Publisher: Elsevier B.V., CODEN: FTRPAE ISSN: 0367-326X. Journal written in English. CAN 148:354445 AN 2007:956497 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


To probe sepn. mechanism and detn. with capillary zone electrophoresis (CZE) and liq. chromatog. (LC), nine compds. with identical flavanone skeleton were studied. Optimum sepn. of LC was attained with gradient of acetonitrile and 5 mM phosphate buffer (pH 6.9). For CE, electrolyte buffer was 4.5 mM SDS in 32 mM sodium tetraborate buffer (pH 9.2). The distinguishing feature in this work was successful sepn. of monohydroxyl stereoisomers by CZE. Polarity is generally increased with hydroxyl groups. In a sepn. mechanism study, polarity would be reduced by intramol. hydrogen bond between hydroxyl of C5 and carbonyl group of C4. Comparison of the retention results among monohydroxyl flavanones shows polarity with hydroxyl at C6 the least, and that at C4' and C7 nearly equal. Also, elution order of flavones and flavanones would be adverse due to the hydroxyl at C3 in LC. From the numerical value pKa of flavanone, the C7-OH is the smallest, and two hydroxyl groups in an adjacent position is always less than the unique one caused by forming a stable 5-membered ring. Investigation of sepn. mechanism yield only the effect of constituent but also reasonable explanation for contradictory results between L. W. Wulf and C. W. Nagel (1976) and the authors' lab., this due to the hydroxyl at C3.

Abstract

Separation mechanism and determination of flavanones with capillary electrophoresis and high-performance liquid chromatography. Wang, Shu-Ping; Fu, Ming-Dung; Wang, Mi-Hung. Department of Applied Chemistry, Providence University, Taichung Hsein, Taiwan. Journal of Chromatography, A (2007), 1164(1-2), 306-312. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 147:482146 AN 2007:956889 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The colorimetric method for detn. of flavonoids in Radix Glycyrrhizae was established and the purifn. process of flavonoids was studied. The principle of colorimetric method was that flavanone could be converted into chalcone in alk. condition. The purifn. process of was optimized by using polyamide with the amt. of naringin as ref. substance and index. The purifn. process was as followed: the ratio of Radix Glycyrrhizae to polyamide was 2:1 (g/g), the ratio of diam. to height of column was 1:7, 5 times bed vol. of 70% ethanol was used, the eluted rate of flavonoids was 90%, and the av. recovery rate of flavonoids was 98.81% with RSD of 2.00%. The amt. of flavonoids in total solids was 45%.

Abstract

Publisher: Guojia Shipin Yaopin Jiandu Guanliju, Xinxi Zhongxin Zhongchengyao Xinxizhan, CODEN: ZHONBS ISSN: 1001-1528. Journal written in Chinese. CAN 148:128542 AN 2007:960476 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH,

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW

WO 2007094384 A1 20070823 WO 2007-JP52672 20070215Patent No. Kind Date Application No. Date Patent Family Information

External preparation for skin containing flavanone derivative. Kida, Naoko; Tada, Akihiro; Kanamaru, Akiko. (Pola Chemical Industries Inc., Japan). PCT Int. Appl. (2007), 51pp. CODEN: PIXXD2 WO 2007094384 A1 20070823 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2007-JP52672 20070215. Priority: JP 2006-37647 20060215; JP 2006-181185 20060630; JP 2006-181186 20060630; JP 2006-195034 20060718. CAN 147:262963 AN 2007:933852 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The biosynthesis of flavonoids and proanthocyanidins was studied in cultivated strawberry (Fragaria × ananassa) by combining biochem. and mol. approaches. Chem. analyses showed that ripe strawberries accumulate high amts. of pelargonidin-derived anthocyanins, and a larger pool of 3',4'-hydroxylated proanthocyanidins. Activities and properties of major recombinant enzymes were demonstrated by means of in vitro assays, with special emphasis on specificity for the biol. relevant 4'- and 3',4'-hydroxylated compds. Only leucoanthocyanidin reductase showed a strict specificity for the 3',4'-hydroxylated leucocyanidin, while other enzymes accepted either hydroxylated substrate with different relative activity rates. The structure of late flavonoid pathway genes, leading to the synthesis of major compds. in ripe fruits, was elucidated. Complex developmental and spatial expression patterns were shown for phenylpropanoid and flavonoid genes in fruits throughout ripening as well as in leaves, petals and roots. Presented results elucidate key steps in the biosynthesis of strawberry flavonoid end products.

Abstract

Characterization of major enzymes and genes involved in flavonoid and proanthocyanidin biosynthesis during fruit development in strawberry (Fragaria × ananassa). Almeida, Joao R. M.; D'Amico, Eleonora; Preuss, Anja; Carbone, Fabrizio; de Vos, C. H. Ric; Deiml, Bettina; Mourgues, Fabienne; Perrotta, Gaetano; Fischer, Thilo C.; Bovy, Arnaud G.; Martens, Stefan; Rosati, Carlo. Department of Genetics and Genomics, Trisaia Research Center, ENEA, Rotondella, Italy. Archives of Biochemistry and Biophysics (2007), 465(1), 61-71. Publisher: Elsevier, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN 147:443940 AN 2007:955291 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


activity. Moreover, the pattern of the main flavanone compds. in the juices has been detd. by HPLC anal.


flavanone

Extraction of total flavanones from Herba Plantaginis and its identification by ultrasonic wave. Huang, Suoyi; Zhang, Bibliographic Information Answer 162:

A method coupling high-performance liq. chromatog. (HPLC) with diode-array detector (DAD) and electrospray ionization mass spectrometry (ESI) was established for the sepn. and characterization of flavonoids in Sophora flavescens Ait. Based on the chromatog. sepn. of most flavonoids present in S. flavescens Ait., a total of 24 flavonoids were identified. Fourteen compds. were unambiguously identified comparing exptl. data for retention time (t R), UV and MS spectra with those of the authentic compds.: 3',7-dihydroxy-4'-methoxy-isoflavone, trifolirhizin, kurarinol, formononetin, 7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone, maackiain, isoxanthohumol, kuraridine, kuraridinol, sophoraflavanone G, xanthohumol, isokurarinone, kurarinone and kushenol D, and addnl. 10 compds. were tentatively identified as kushenol O, trifolirhizin-6''-malonate, sophoraisoflavanone A (20), norkurarinol/kosamol Q, kushenol I/N, kushenol C, 2'-methoxykurarinone, kosamol R, kushecarpin A and kushenol A by comparing exptl. data for UV and MS spectra with those of literature. Furthermore, fragmentation pathways in pos. ions mode of 24 flavonoid compds. of types of flavanone, flavanonol, flavonol, chalcone, isoflavone, isoflavanone and ptercocarpane were summarized. Some common features, such as CH3⋅, H2O, CO, CO2, C3O2 and C2H2O losses, together with Retro-Diels-Alder fragmentations were obsd. in the prenylated flavonoids in S. flavescens Ait. The loss of the lanandulyl chain was their characteristic fragmentation, which might help deducing the structure of unknown flavonoid compds. The present study provided an approach to rapidly characterize bioactive constituents in S. flavescens Ait.

Abstract

Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry. Zhang, Lei; Xu, Liang; Xiao, Shan-Shan; Liao, Qiong-Feng; Li, Qing; Liang, Jian; Chen, Xiao-Hui; Bi, Kai-Shun. Laboratory of Pharmaceutical Analysis, School of Pharmacy, Shenyang Pharmaceutical University, Liaoning, Peop. Rep. China. Journal of Pharmaceutical and Biomedical Analysis (2007), 44(5), 1019-1028. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 147:455734 AN 2007:926580 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


To increase a tissue regeneration ability of a living body such as a collagen prodn. ability of fibroblast in the dermis in a skin defect area typified by a large wrinkle or wound, a flavanone deriv. such as farrerol is used as an active ingredient of an external prepn. for skin. Further, to efficiently screen a substance having an excellent effect on promoting wound healing, the remodeling action of collagen fiber bundle is tested by using a skin wound model.

Abstract JP 2006-195034 A 20060718JP 2006-181186 A 20060630JP 2006-181185 A 20060630JP 2006-37647 A 20060215Priority Application

GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM


flavanone

Medical drugs known to modulate the activity of human ATP-binding cassette (ABC) transporter proteins (modulators) were tested for the ability to potentiate the activity of the azole fungicide cyproconazole against in vitro growth of Mycosphaerella graminicola and to control disease development due to this pathogen on wheat seedlings. In vitro modulation of cyproconazole activity could be

Abstract

Control of Mycosphaerella graminicola on wheat seedlings by medical drugs known to modulate the activity of ATP-binding cassette transporters. Roohparvar, Ramin; Huser, Aurelie; Zwiers, Lute-Harm; De Waard, Maarten A. Laboratory of Phytopathology, Wageningen University, Wageningen, Neth. Applied and Environmental Microbiology (2007), 73(15), 5011-5019. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 147:401569 AN 2007:908285 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A chloroform ext. of the root bark of Cudrania tricuspidata showed an inhibitory effect on mammalian DNA topoisomerase I. The topoisomerase I inhibitory compd. was purified and identified as 2S-2',5,7-trihydroxy-4',5'-(2,2-dimethylchromeno)-6-prenyl flavanone (cudraflavanone A). Cudraflavanone A was shown to inhibit the activity of topoisomerase I with approx. 0.4 mmol/L 50% inhibitory concn. A concn. of 6 μmol/L cudraflavanone A caused a 50% growth inhibition of human cancer cell U937. Cudraflavanone A-induced cell death was characterized by the cleavage of poly(ADP-ribose) polymerase and pro-caspase-3. Furthermore, cudraflavanone A induced the fragmentation of DNA into multiples of 180 bp (an apoptotic DNA ladder), indicating that the inhibitor triggered apoptosis. This induction of apoptosis by cudraflavanone A was also confirmed using flow-cytometry anal. In addn., this compd. inhibited protein kinase C activity with approx. 150 μmol/L 50% inhibitory concn. Taken together, these results suggest that cudraflavanone A may function by inhibiting oncogenic disease, at least in part, through the inhibition of protein kinase C and topoisomerase I activity.

Abstract

Cudraflavanone A purified from Cudrania tricuspidata induces apoptotic cell death of human leukemia U937 cells, at least in part, through the inhibition of DNA topoisomerase I and protein kinase C activity. Rho, Youn-Hwa; Lee, Byong-Won; Park, Ki-Hun; Bae, Young-Seuk. Department of Biochemistry, College of Natural Sciences, Kyungpook National University, Taegu, S. Korea. Anti-Cancer Drugs (2007), 18(9), 1023-1028. Publisher: Lippincott Williams & Wilkins, CODEN: ANTDEV ISSN: 0959-4973. Journal written in English. CAN 147:419445 AN 2007:914838 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The methods for extn. and identification of total flavanones of Herba Plantaginis were investigated to explore the use of Plantago resources. The flavonoids were extd. by ethanol as the solvent from Herba Plantaginis with ultrasonic wave extn. and detected by using spectrophotometry. By this method, the content of the total flavanones of Herba Plantaginis was 1.24%, and the av. recovery was 103%. The purity of the flavanones was very high. This method was a purely phys. process, and was an ideal way to ext. the flavanones of Herba Plantaginis.

Abstract

Jingxuan; Cheng, Hui; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Wenben Province, Peop. Rep. China. Shizhen Guoyi Guoyao (2006), 17(4), 557-558. Publisher: Shizhen Guoyi Guoyao Bianweihui, CODEN: SGGHAL ISSN: 1008-0805. Journal written in Chinese. CAN 148:61455 AN 2007:916987 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Identification of flavonoid glycosides using metal complexation and tandem mass spectrometry. Davis, Barry D.; Pikulski, Bibliographic Information Answer 167:

Four flavanone glycosides were purified from seeds of Mabea fistulifera. Their chemotaxonomic significance is discussed. Abstract

Flavanone glycosides from Mabea fistulifera Mart. (Euphorbiaceae). Coqueiro, Aline; Sarragiotto, Maria Helena; Zocoler, Marcos Alberto; Vidotti, Gentil Jose. Departamento, de Quimica, Universidade Estadual de Maringa, Parana, Brazil. Biochemical Systematics and Ecology (2007), 35(10), 717-719. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 148:210180 AN 2007:898779 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Pear (Pyrus sp.) is a major fruit crop of temperate regions with increasing extent of cultivation. Pear flavonoids contribute to its fruit color, pathogen defense, and are health beneficial ingredients of the fruits. Comparative Southern analyses with apple (Malus x domestica) cDNAs showed comparable genomic organization of flavonoid genes of both related genera. A homol.-based cloning approach was used to obtain the cDNAs of most enzymes of the main flavonoid pathway of Pyrus: phenylalanine ammonia lyase, chalcone synthase, chalcone isomerase, flavanone 3β-hydroxylase, flavonol synthase, dihydroflavonol 4-reductase, leucoanthocyanidin reductase 1 and 2, anthocyanidin synthase, anthocyanidin reductase, and UDP-glucose : flavonoid 7-O-glucosyltransferase. The substrate specificities of the recombinant enzymes expressed in yeast were detd. for physiol. and non-physiol. substrates and found to be in general agreement with the characteristic pear flavonoid metabolite pattern of mainly B-ring dihydroxylated anthocyanins, flavonols, catechins, and flavanones. Furthermore, significant differences in substrate specificities and gene copy nos. in comparison to Malus were identified. Cloning of the cDNAs and studying the enzymes of the Pyrus flavonoid pathway is an essential task toward a comprehensive knowledge of Pyrus polyphenol metab. It also elucidates evolutionary patterns of flavonoid/polyphenol pathways in the Rosaceae, which allocate several important crop plants.

Abstract

Flavonoid genes of pear (Pyrus communis). Fischer, Thilo C.; Gosch, Christian; Pfeiffer, Judith; Halbwirth, Heidrun; Halle, Christian; Stich, Karl; Forkmann, Gert. Lehrstuhl fuer Zierpflanzenbau und Gartenbauliche Pflanzenzuechtung, Department fuer Pflanzenwissenschaften, Technische Universitaet Muenchen Weihenstephan, Freising, Germany. Trees (Heidelberg, Germany) (2007), 21(5), 521-529. Publisher: Springer, CODEN: TRESEY ISSN: 0931-1890. Journal written in English. CAN 148:234148 AN 2007:905709 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


demonstrated in paper disk bioassays. Some of the active modulators (amitriptyline, flavanone, and phenothiazines) increased the accumulation of cyproconazole in M. graminicola, suggesting that they reversed cyproconazole efflux. However, synergism between cyproconazole and modulators against M. graminicola on wheat seedlings could not be shown. Despite their low in vitro toxicity to M. graminicola, some modulators (amitriptyline, loperamide, and promazine) did show significant intrinsic disease control activity in preventive and curative foliar spray tests with wheat seedlings. The results suggest that these compds. have indirect disease control activity based on modulation of fungal ABC transporters essential for virulence and constitute a new class of disease control agents.


flavanone

Abstract US 2006-787343P P 20060329US 2006-755758P P 20060103Priority Application




Generation of variants of pharmacophore compounds using combinations of catalytic domains of enzymes involved in secondary metabolite biosynthesis. Evans, Glen A.; Finlayson, Malcolm. (Pharmagic, Inc., USA). PCT Int. Appl. (2007), 66pp., which. CODEN: PIXXD2 WO 2007089382 A2 20070809 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2007-US130 20070103. Priority: US 2006-755758 20060103; US 2006-787343 20060329. CAN 147:250561 AN 2007:874236 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The precise identification of flavonoid glycosides using mass spectrometry is a challenging task. The glycosidic portions are a particular challenge due to structural isomerism and multiple possible glycosylation sites. Simple metal complexation techniques have been developed which provide this information when used in combination with tandem mass spectrometry. In this way, isomeric compds. that usually yield identical fragmentation patterns are readily differentiated. The fragmentation patterns of the metal complexes are consistent for particular structural motifs, expanding the range of this identification technique to a large no. of mols. Metal complexation can be adapted to LCMS methods to provide structural information for reversed-phase liq. chromatog. sepns. The method has been proven applicable to the flavonol, flavone and flavanone classes.

Abstract

Michael; Zhang, Junmei; Needs, Paul W.; Kroon, Paul A.; Brodbelt, Jennifer S. Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX, USA. Abstracts of Papers, 234th ACS National Meeting, Boston, MA, United States, August 19-23, 2007 (2007), AGFD-008. Publisher: American Chemical Society, Washington, D. C CODEN: 69JNR2 Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2007:877848 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Two new dihydrochalcones, 2,3-dihydroxy-4,3',4',5'-tetramethoxydihydrochalcone (1) and 4,2',4'-trihydroxy-3'-methoxydihydrochalcone (2), and a new flavanone, (2R,3R)-(-)-3,5-dihydroxy-6,7-dimethoxyflavanone (3), together with 19 known compds. were isolated from the leaves of Muntingia calabura. The structures of three new compds. were detd. through spectral analyses including extensive 2D-NMR data. Among the isolates, 2,3-dihydroxy-4,3',4',5'-tetramethoxydihydrochalcone, 5,7-dihydroxy-3-methoxyflavone, 5,7-dihydroxy-6-methoxyflavone, 5,4'-dihydroxy-3,7-dimethoxyflavone, (2S)-7,8,3',4',5'-pentamethoxyflavan,

Abstract

New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura. Chen, Jih-Jung; Lee, Hsinn-Hsing; Shih, Cheng-Dean; Liao, Chang-Hui; Chen, Ih-Sheng; Chou, Tsung-Hsien. Graduate Institute of Pharmaceutical Technology, Tajen University, Pingtung, Taiwan. Planta Medica (2007), 73(6), 572-577. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 148:96612 AN 2007:865143 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Transcription factor signal transducer and activator of transcription (Stat)-3 is activated constitutively in prostate cancer (PCA) suggesting that its disruption could be an effective approach to control this malignancy. Here we assessed whether silibinin, a flavanone from Silybum marianum with proven anticancer efficacy in various cancer models, inhibits Stat3 activation in DU145 cells, and if it does, what is the biol. fate of the cells. At 50 μM or higher concns. for 24 or 48 h, silibinin concn. dependently reduced constitutive Stat3 phosphorylation at Tyr705 and Ser727 residues under both serum and serum-starved conditions. Constitutively active Stat3-DNA binding was also inhibited concn. dependently by silibinin; however, apoptotic death together with caspase and poly(ADP-ribose) polymerase (PARP) cleavage was obsd. by silibinin only under serum-starved conditions suggesting that addnl. survival pathways are active under serum conditions. In other studies, cells were treated with various specific pharmacol. inhibitors where phosphorylation of Stat3 was not reduced by epidermal growth factor receptor and Mitogen activated protein/extracellular signal regulate kinase kinase (MEK1/2) inhibitors, suggesting lack of significant roles of these in Stat3 activation in DU145 cells. Janus kinase (JAK)-1 and JAK2 inhibitors strongly reduced Stat3 phosphorylation but did not result in apoptotic cell death. Interestingly, JAK1 inhibitor only in combination with silibinin resulted in a complete redn. in Stat3 phosphorylation at Tyr705, activated caspase-9 and caspase-3, and caused strong PARP cleavage and apoptotic death of DU145 cells. Given a crit. role of Stat3 activation in PCA, our results showed that silibinin inhibits constitutively active Stat3 and induces apoptosis in DU145 cells, and thus might have potential significance in therapeutic intervention of this deadly malignancy.

Abstract

Silibinin inhibits constitutive activation of Stat3, and causes caspase activation and apoptotic death of human prostate carcinoma DU145 cells. Agarwal, Chapla; Tyagi, Alpna; Kaur, Manjinder; Agarwal, Rajesh. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Science Center, Denver, CO, USA. Carcinogenesis (2007), 28(7), 1463-1470. Publisher: Oxford University Press, CODEN: CRNGDP ISSN: 0143-3334. Journal written in English. CAN 147:203249 AN 2007:869141 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Methods of generating variants natural compds. contg. pharmacophores are described. The method involves generating new combinations of the catalytic moieties of enzymes assocd. with the biosynthesis of related compds. in a suitable host for biosynthesis. The genes for these enzymes can be ordered, e.g. on a single vector, or on sep. vectors to allow randomization of the order of reaction. Depending upon the nature and order of the catalytic domains and the precursors fed to the host, new variants of a pharmacophore-contg. compd. can be generated.


flavanone

The anti-inflammatory properties of 3 flavanones isolated from Inula viscosa, sakuranetin, 7-O-methylaromadendrin, and 3-acetyl-7-O-methylaromadendrin, were tested both in vitro and in vivo. Acute inflammation in vivo was induced by topical application of 12-O-tetradecanoylphorbol 13-acetate (TPA) to mouse ears or by s.c. injection of phospholipase A2 (PLA2) into mouse paws. The test compds. were evaluated in vitro for their effect on both the metab. of arachidonic acid and on the release and/or activity of enzymes involved in the inflammatory response such as elastase, myeloperoxidase (MPO), and protein kinase C (PKC). The most active compds. in vivo against PLA2-induced paw edema were 7-O-methylaromadendrin (ED50 = 8 mg/kg) and sakuranetin (ED50 = 18 mg/kg). In contrast, the most potent compd. against TPA-induced ear edema was 3-acetyl-7-O-methylaromadendrin (ED50 = 185 μg/ear), followed by sakuranetin (ED50 = 205 μg/ear). In vitro, the latter compd. was the most potent inhibitor of leukotriene (LT) B4 prodn. by peritoneal rat neutrophils (IC50 = 9 μM) and it was also the only compd. that directly inhibited the activity of 5-lipoxygenase (5-LOX). 3-Acetyl-7-O-methylaromadendrin also inhibited LTB4 prodn. (IC50 = 15 μM), but had no effect on 5-LOX activity. The only

Abstract

Effects of naturally occurring dihydroflavonols from Inula viscosa on inflammation and enzymes involved in the arachidonic acid metabolism. Hernandez, Victoriano; Recio, M. Carmen; Manez, Salvador; Giner, Rosa M.; Rios, Jose-Luis. Departament de Farmacologia, Facultat de Farmacia, Universitat de Valencia, Spain. Life Sciences (2007), 81(6), 480-488. Publisher: Elsevier B.V., CODEN: LIFSAK ISSN: 0024-3205. Journal written in English. CAN 148:229481 AN 2007:857083 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The intake of flavonoids has been inversely related to the risk of various common neoplasms, but scanty data exist on oral and pharyngeal cancer. We used data from a case-control study conducted in Italy between 1992 and 2005 to examine the relationship between flavonoid intake and oral and pharyngeal cancer risk. The study included 805 cases with incident, histol. confirmed oral and pharyngeal cancer, and 2,081 hospital controls admitted for acute, nonneoplastic conditions. We have applied data on food and beverage content of six major classes of flavonoids, on dietary information collected through a validated food-frequency questionnaire. The odds ratios (OR) were calcd. using multiple logistic regression models, conditioned on study center, sex, and age. After adjustment for education, tobacco, alc., body mass index, and non-alc. energy intake, ORs for the highest vs. the lowest quintile of intake were 0.51 [95% confidence intervals (95% CI), 0.37-0.71] for flavanones, 0.62 (CI, 0.43-0.89) for flavonols, and 0.56 (95% CI, 0.40-0.78) for total flavonoids. No significant assocn. emerged for isoflavones (OR, 0.90), anthocyanidins (OR, 0.86), flavan-3-ols (OR, 0.84), and flavones (OR, 0.75). The ORs were consistent across strata of age, sex, education, body mass index, tobacco, and alc. After allowance for vegetable and fruit consumption, the inverse relations with total flavonoids and flavanones remained significant, whereas that with flavonols became nonsignificant. None of the assocns. were significant after further allowance for vitamin C, probably on account of the high collinearity between these compds.

Abstract

Flavonoids and the risk of oral and pharyngeal cancer: a case-control study from Italy. Rossi, Marta; Garavello, Werner; Talamini, Renato; Negri, Eva; Bosetti, Cristina; Dal Maso, Luigino; Lagiou, Pagona; Tavani, Alessandra; Polesel, Jerry; Barzan, Luigi; Ramazzotti, Valerio; Franceschi, Silvia; La Vecchia, Carlo. Istituto di Ricerche Farmacologiche "Mario Negri", Milan, Italy. Cancer Epidemiology, Biomarkers & Prevention (2007), 16(8), 1621-1625. Publisher: American Association for Cancer Research, CODEN: CEBPE4 ISSN: 1055-9965. Journal written in English. CAN 148:10428 AN 2007:863998 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(2S)-5'-hydroxy-7,8,3',4'-tetramethoxyflavan, and Me gallate exhibited significant anti-platelet aggregation activity in vitro.


flavanone

The present study evaluated the pharmacokinetics of 3 different grapefruit flavanone forms in dog blood plasma and demonstrated their absorption after an oral intake of a grapefruit ext.; pharmacokinetic parameters of these forms were also detd. Ten healthy beagles were administered 70 mg citrus flavonoids as a grapefruit ext. contained in capsules, while 2 addnl. dogs were used as controls and given an excipient. The grapefruit flavanone naringin, along with its metabolites naringenin and naringenin glucuronide, was detected in dog plasma. Blood samples were collected between 0 and 24 h after administration of the ext. Naringin reached its max. plasma concn. at around 80 min, whereas naringenin and naringenin glucuronide reached their max. plasma concn. at around 20 and 30 min, resp. Maximum plasma concns. of naringin, naringenin, and naringenin glucuronide (medians and ranges) were 0.24 (0.05-2.08), 0.021 (0.001-0.3), and 0.09 (0.034-0.12) μmol/l, resp. The areas under the curves were 23.161 (14.04-70.62) min × μmol/for nariningin, 1.78 (0.09-4.95) min × μmol/l for naringenin, and 22.5 (2.74-99.23) min × μmol/l for naringenin glucuronide. The median and range values for mean residence time were 3.3 (1.5-9.3), 2.8 (0.8-11.2), and 8.0 (2.3-13.1) h for naringin, naringenin, and naringenin

Abstract

Absorption and pharmacokinetics of grapefruit flavanones in beagles. de Lourdes Mata-Bilbao, Maria; Andres-Lacueva, Cristina; Roura, Elena; Jauregui, Olga; Escribano, Elvira; Torre, Celina; Lamuela-Raventos, Rosa Maria. Department of Nutrition and Food Science, CerTA, Faculty of Pharmacy, University of Barcelona, Barcelona, Spain. British Journal of Nutrition (2007), 98(1), 86-92. Publisher: Cambridge University Press, CODEN: BJNUAV ISSN: 0007-1145. Journal written in English. CAN 147:226135 AN 2007:847022 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Some blood orange juice (BOJ) flavanones may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective, and anticarcinogenic properties. The aim of the present study was to evaluate the pharmacokinetics of hesperetin and naringenin in human subjects after BOJ intake. In a cross-over study, 7 healthy female volunteers consumed 150 and 300 mL BOJ corresponding to about 51-102 mg hesperetin and to 6-12 mg naringenin, resp. Plasma samples were collected before, each hour for 8 h and 24 h after BOJ administration and analyzed for their content of hesperetin and naringenin by liq. chromatog.-MS/MS. The blood plasma concns. of these compds. were dose dependent and the peak concn. (Cmax) was reached in 5⋅1 h after BOJ intake. The Cmax of hesperetin was 43⋅4 and 79⋅8 ng/mL after 150 and 300 mL intake, resp. For naringenin the plasma peak was 16⋅4 and 34⋅0 ng/mL. Moreover, the conjugated forms of these flavanones represent more than 95% of the plasma concn. The results indicate that both hesperetin and naringenin are bioavailable after BOJ intake; naringenin seemingly more so than hesperetin.

Abstract

Flavanone plasma pharmacokinetics from blood orange juice in human subjects. Gardana, Claudio; Guarnieri, Serena; Riso, Patrizia; Simonetti, Paolo; Porrini, Marisa. DiSTAM - Department of Food Science and Microbiology, Division of Human Nutrition, University of Milan, Milan, Italy. British Journal of Nutrition (2007), 98(1), 165-172. Publisher: Cambridge University Press, CODEN: BJNUAV ISSN: 0007-1145. Journal written in English. CAN 147:226136 AN 2007:847033 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone that inhibited the secretory PLA2 activity in vitro was 7-O-methylaromadendrin. This finding may partly explain the anti-inflammatory effect obsd. in vivo, although other mechanisms such as the inhibition of histamine release by mast cells may also be implicated. Sakuranetin at 100 μM was found to inhibit elastase release, although this result is partly due to direct inhibition of the enzyme itself. At the same concn., 7-O-methylaromadendrin only affected the enzyme release. Finally, none of the flavanones exhibited any effect on MPO or PKC activities. Taken together, these findings indicate that sakuranetin may be a selective inhibitor of 5-LOX.


flavanone


Juices from the mandarin Clemenules (Citrus clementina Hort. ex Tan.), the tangor Ortanique (Citrus reticulata Blanco × Citrus sinensis Osb.) and the sweet orange Valencia Late (Citrus sinensis) have been industrially squeezed, pasteurized, concd. and stored under refrigeration (4°) and at room temp. (20°). After each process, the flavanone-7-O-glycosides (FGs) and fully methoxylated flavones (FMFs) contents as well as total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities were detd. and compared with those from the corresponding fresh hand-squeezed juices. Neither industrial-squeezing, nor pasteurization or concn. significantly affected FGs and FMFs contents and antiradical activities of assayed juices. Storage caused a slight decrease of the FMFs contents but a significant redn. of both sol. hesperidin contents and cumulative fast-kinetics antiradical activities in all assayed juices. These decreases were dependent on storage temp. Characteristic values of the varietal characterization parameters, which are derived from the FMFs contents and antiradical activities of fresh hand-squeezed juices, held valid for industrially squeezed, pasteurized and concd. juices. After storage, however, only the FMFs-derived varietal characterization parameters and cumulative slow-kinetics antiradical activity remained valid for the resulting juices.

Abstract

Effect of technological processes and storage on flavonoids content and total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities of citrus juices. Sentandreu, Enrique; Navarro, Jose L.; Sendra, Jose M. Instituto de Agroquimica y Tecnologia de Alimentos, Burjassot, Valencia, Spain. European Food Research and Technology (2007), 225(5-6), 905-912. Publisher: Springer GmbH, CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 147:468220 AN 2007:840514 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


High-performance liq. chromatog. coupled with a UV photodiode-array detector and a mass spectrometer (HPLC-MS) was used to analyze the constituents of an ext. of Citrus changshan-huyou Y. B. Chang peel. Structures of two flavanones were identified based on their abundant [M+H]+ ions, UV spectra, and 1HNMR and 13CNMR spectrometer as 5,4'-dihydroxy flavanone-7-O-α-glucoside (naringenin-7-O-α-glucoside) and 5,3'-dihydroxy-4'-methoxy flavanone-7-O-α-glucoside (hesperetin-7-O-α-glucoside). The two flavanones were first identified from peel of Citrus changshan-huyou Y. B. Chang.

Abstract

Identification of flavanones from peel of Citrus changshan-huyou Y. B. Chang, by HPLC-MS and NMR. Li, Chunmei; Gu, Haifeng; Dou, Hongliang; Zhou, Liming. College of Food Science and Technology, Huazhong Agriculture University, Wuhan City, Peop. Rep. China. European Food Research and Technology (2007), 225(5-6), 777-782. Publisher: Springer GmbH, CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 148:187092 AN 2007:840522 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


glucuronide, resp. The results of the present study demonstrate the absorption of grapefruit flavanones via the presence of their metabolites in plasma, thus making an important contribution to the field since the biol. activities ascribed to these compds. rely on their specific forms of absorption.


flavanone

The fragmentation behavior of (+)-silybin (I) and (+)-deuterosilybin (II), as well as of their flavanone-3-of-type building blocks, such as 3,5,7-trihydroxy-2-phenyl-4-chromanone (III) and 2-(1,4-benzodioxolanyl)-3,5,7-trihydroxy-4-chromanone (IV), were investigated by atm. pressure chem. ionization quadrupole time-of-flight tandem mass spectrometry in the pos. ion mode (APCI(+)-QqTOF MS/MS). The product ion spectra of the protonated mols. of I revealed a rather complicated fragmentation pattern with product ions originating from consecutive and competitive loss of small mols. such as H2O, CO, CH2O, CH3OH and 2-methoxyphenol, along with the A+ - and B+-type ions arising from the cleavage of the C-ring of the flavanone-3-ol moiety. The elucidation of the fragmentation behavior of I was facilitated by acquiring information on the fragmentation characteristics of the flavanone-3-ol moieties and II. The capability of the accurate mass measurement on the quadrupole time-of-flight mass spectrometer allowed us to det. the elemental compn. of each major product ion. Second-generation product ion spectra obtained by combination of in-source collision induced dissocn. (CID) with selective CID (pseudo-MS3) was also helpful in elaborating the fragmentation pathways and mechanism. Based on the exptl. results, a fragmentation mechanism as well as fragmentation pathways for I and its flavanone-3-ol building blocks III, IV are proposed and discussed.

Abstract

(+)-Silybin, a pharmacologically active constituent of Silybum marianum: fragmentation studies by atmospheric pressure chemical ionization quadrupole time-of-flight tandem mass spectrometry. Keki, Sandor; Toth, Katalin; Zsuga, Miklos; Ferenczi, Renata; Antus, Sandor. Department of Applied Chemistry, University of Debrecen, Debrecen, Hung. Rapid Communications in Mass Spectrometry (2007), 21(14), 2255-2262. Publisher: John Wiley & Sons Ltd., CODEN: RCMSEF ISSN: 0951-4198. Journal written in English. CAN 147:392707 AN 2007:834087 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The antioxidant (DPPH radical and superoxide anion scavenging activities), and cytotoxic (in tumor, Jurkat, PC-3, Colon 205, HepG2, and normal PBMCs cells) activities of 16 plant phenolic or related compds. were evaluated in vitro. Different categories compds.

Abstract

Antioxidant and cytotoxic activities of naturally occurring phenolic and related compounds: A comparative study. Rao, Yerra Koteswara; Geethangili, Madamanchi; Fang, Shih-Hua; Tzeng, Yew-Min. Institute of Biotechnology, Chaoyang University of Technology, Wufeng, Taichung, Taiwan. Food and Chemical Toxicology (2007), 45(9), 1770-1776. Publisher: Elsevier Ltd., CODEN: FCTOD7 ISSN: 0278-6915. Journal written in English. CAN 148:182415 AN 2007:829723 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

O

OH

H

H

HOH

OHOH

O

OH OMe

O

O

O

OH

H

H

HOH

OHOH

O

OH OMe

OH

HOH

OH

O

OH O

O

O

H

HOH

OH

O

OH

R

D

I

IVIII

II


flavanone

Answer 181:

The flavonoids were extd. from gendarussa ventricosa by ultrasonic wave and ethanol extn. The coloration reaction and paper-chromatog. were used to identify the flavonoids in gendarussa ventricosa. Spectrophotometry was used to det. the amt. of the total flavanone. By this method, the concn. of total flavanone in gendarussa ventricosa was C = 0.1230 mg/mL and the recovery rate was 99.05%. This method is simple without any pollution, and is an ideal way to ext. the total flavanone in gendarussa ventricosa.

Abstract

Extraction and identification of total flavanone in gendarussa ventricosa. Sun, Ting-ting; Pei, Zheng-ling; Huang, Suo-yi. Youjiang Medical College of Nationalities, Beise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(3), 23-24. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 147:474387 AN 2007:825584 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanone 3β-hydroxylase (FHT) and flavone synthase I (FNS I) are 2-oxoglutarate-dependent dioxygenases with 80% sequence identity, which catalyze distinct reactions in flavonoid biosynthesis. However, FNS I has been reported exclusively from a few Apiaceae species, whereas FHTs are more abundant. Domain-swapping expts. joining the N terminus of parsley (Petroselinum crispum) FHT with the C terminus of parsley FNS I and vice versa revealed that the C-terminal portion is not essential for FNS I activity. Sequence alignments identified 26 amino acid substitutions conserved in FHT vs. FNS I genes. Homol. modeling, based on the related anthocyanidin synthase structure, assigned seven of these amino acids (FHT/FNS I, M106T, I115T, V116I, I131F, D195E, V200I, L215V, and K216R) to the active site. Accordingly, FHT was modified by site-directed mutagenesis, creating mutants encoding from one to seven substitutions, which were expressed in yeast (Saccharomyces cerevisiae) for FNS I and FHT assays. The exchange I131F in combination with either M106T and D195E or L215V and K216R replacements was sufficient to confer some FNS I side activity. Introduction of all seven FNS I substitutions into the FHT sequence, however, caused a nearly complete change in enzyme activity from FHT to FNS I. Both FHT and FNS I were proposed to initially withdraw the β-face-configured hydrogen from carbon-3 of the naringenin substrate. Our results suggest that the 7-fold substitution affects the orientation of the substrate in the active-site pocket such that this is followed by syn-elimination of hydrogen from carbon-2 (FNS I reaction) rather than the rebound hydroxylation of carbon-3 (FHT reaction).

Abstract

Evolution of flavone synthase I from parsley flavanone 3β-hydroxylase by site-directed mutagenesis. Gebhardt, Yvonne Helen; Witte, Simone; Steuber, Holger; Matern, Ulrich; Martens, Stefan. Institut fuer Pharmazeutische Biologie, Philipps-Universitaet Marburg, Marburg, Germany. Plant Physiology (2007), 144(3), 1442-1454. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 147:338207 AN 2007:827624 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


corresponding to 10 flavonoids, three lignans, two phenolic acids, and a catechin showed significant mean differences in antioxidant and cytotoxic activities. Particularly, the flavonols, quercetin (3) and tiliroside (11) possess significant antioxidant activity, as well as cytotoxic activity against Jurkat; and Jurkat and HepG2 cells, resp. In contrast, the flavanone, 5,7-dimethoxy-3',4'-methylenedioxyflavanone (7), and homoisoflavonoid, isobonducellin (10) shown to have no significant antioxidant activity, but exhibited potent cytotoxic activity in Jurkat and HepG2 cells, while moderate growth inhibition against Colon205 cells. Interestingly, none of these derivs. shown to have toxicity toward normal peripheral blood mononuclear cells, over the concn. range tested (5-200 μM). Cytotoxic activities of some natural flavonoids identified in the medicinal plants were evaluated for the first time.


flavanone


Skin preparations containing flavanones and polar solvent extracts of Leguminosae plant containing lespedezaflavanone H. Katagiri, Takayuki; Miyase, Toshio; Hongo, Maya. (Pola Chemical Industries, Inc., Japan). Jpn. Kokai Tokkyo Koho (2007), 16pp. CODEN: JKXXAF JP 2007186439 A 20070726 Patent written in Japanese. Application: JP 2006-4718 20060112. Priority: . CAN 147:219391 AN 2007:813576 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The tryptase activity inhibitors contain catechins and/or their glycosides, flavones and/or their glycosides, flavonols and/or their glycosides, flavanones and/or their glycosides, and/or tannins as active ingredients. Topical or oral formulations, foods, or beverages contg. the tryptase inhibitors are useful for treatment or prevention of diseases selected from itching, wrinkle, bags in skin, rough skin, systemic anaphylaxis, aspirin hypersensitivity asthma, asthma, interstitial lung disease, interstitial cystitis, irritable bowel syndrome, allergy, atopic disease, bullous dermatosis, hyperesthesia, pain, pruritus, gingivitis, edema, psoriasis, lung fibrosis, chronic rheumatoid arthritis, periodontal disease, blood coagulation disorder, renal interstitial fibrosis, vascular hyperpermeability or pneumonedema caused by radiog. contrast media, and pollinosis. Thus, tannic acid (at 1 mg/mL) showed 99.7% inhibition of purified human tryptase. Tannic acid showed LD50 of ≥2000 mg/kg p.o. in mice. Formulation examples of skin-lightening lotions, emollient emulsions, shampoos, skin cleansers, hair rinses, hair liqs., bath salts, health food tablets, health beverages, and toothpastes are given.


Tryptase activity inhibitors containing polyphenols, plants, or plant extracts, and their use for topical or oral formulations, foods, or beverages. Ito, Kenichi; Idamarcoda, Alnasili; Kido, Hiroshi. (Ichimaru Pharcos Inc., Japan; Tokushima University). Jpn. Kokai Tokkyo Koho (2007), 36pp. CODEN: JKXXAF JP 2007186457 A 20070726 Patent written in Japanese. Application: JP 2006-6124 20060113. Priority: . CAN 147:172994 AN 2007:813997 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Three new flavanone glycosides named garccowaside A, garccowaside B, garccowaside C, and 3 other known compds. were isolated from the ethanol ext. of the stems of G. cowa. These structures were established on the basis of spectroscopic evidence. Twelve

Abstract

The constituents from the stems of Garcinia cowa Roxb. and their cytotoxic activities. Shen, Jie; Tian, Ze; Yang, Jun-shan. Institute of Medicinal Plant Development, Peking Union Medical College, Chinese Academy of Medical Sciences, Beijing, Peop. Rep. China. Pharmazie (2007), 62(7), 549-551. Publisher: Govi-Verlag Pharmazeutischer Verlag GmbH, CODEN: PHARAT ISSN: 0031-7144. Journal written in English. CAN 147:360552 AN 2007:794738 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Naringenin and its metal complexes are used extensively in chem., biol. and dye industry. In this study, complexes of naringenin with aluminum and iron are examd. by spectrophotometric and potentiometric methods. The stability consts. of these complexes were detd. potentiometrically by using Calvin-Bjerrum and Irving Rossotti methods. The evaluated protonation consts. of the naringenin were found: logK1 = 10.19, logK2 = 8.31, and logK3 = 7.06 at the 25°. Logarithms of the stability consts. were found: for Aluminum complex: logK1 = 15.39 logK2 = 7.12, and logK3 = 6.47 and for Iron complex: logK1 = 10.11, logK2 = 6.40, and logK3 = 6.11 at the 25°. The components of metal-naringenin complexes are given 1:3 (metal:naringenin ratio) both Al(III) and Fe(II) from the results.

Abstract

Determining stability constants of naringenin (4',5,7-trihydroxy flavanone) complexes with aluminum(III) and iron(II) by potentiometric and spectrophotometric methods. Karadag, Recep; Erdogan, Gulbin; Bayar, Mehmet; Dolen, Emre. Laboratory for Natural Dyes, Faculty of Fine Arts, Marmara University, Istanbul, Turk. Reviews in Analytical Chemistry (2007), 26(3), 169-185. Publisher: Freund Publishing House Ltd., CODEN: RACYAX ISSN: 0048-752X. Journal written in English. CAN 147:393371 AN 2007:808809 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH

OH

O

OH

R1

R4

R5

R6

3

2R

R

I

Skin prepns., which inhibit melanin formation, contain flavanones I (R1-R6 = H, OH, isoprenyl; ≥3 of R1-R6 = isoprenyl) and/or their salts. Also claimed are title exts. contg. 0.001-0.1% lespedezaflavanone H (II). Thus, II, obtained by extn. of Lespedeza buergeri stem with MEOH and fractionation, inhibited melanin formation by normal human melanocyte in a dose-dependent manner. Application of skin-lightening lotion contg. II and di-K glycyrrhizate to female volunteers with pigmentation (dark skin, spots, freckles, etc.) lighten the skin color.


flavanone

A new anticancer dihydroflavanoid from the root of Spiranthes australis (R. Brown) Lindl. Peng, Jinyong; Xu, Qiwei; Xu, Youwei; Qi, Yan; Han, Xu; Xu, Lina. School of Pharmacy, Dalian Medical University, Dalian, Peop. Rep. China. Natural Product Research, Part B: Bioactive Natural Products (2007), 21(7), 641-645. Publisher: Taylor & Francis Ltd., CODEN: NPRPEA Journal written in English. CAN 147:371325 AN 2007:778584 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. constituents of the leaves of Iris songarica Schrenk were studied. The chem. constituents is prepd. by extd. with 70% alc., isolating by column on silica gel and purifying by recrystn. etc. Eighteen compds. were isolated from the leaves of Iris songarica. On the basis of the spectral data, the structures were identified as tectochrysin(I), wogonin(II), acacetin-7-O-α-L-rhamnopyranosyl-(1,6)-β-D-glucopyranoside(III), izalpinin(IV), isorhamnetin-7-O-β-D-glucoside(V), 5,2'-dihydroxy-6,7-methylenedioxy flavanone (VI), 5,7-dihydroxy-6,2'-dimethoxyisoflavone (VII), tectorigenin (VIII), tectoridin (c), irisolone , irisoid A(X I), irisoid B (X II), irisoid D(X III), n-hentriacontanol (X IV), daucosterol (X V), stigmasterol (X VI), nonadecanoic acid (X VII) and β-sitosterol (X VIII). All the eighteen compds. have been isolated from this plant for the first time, and compds. III, IV and V have been isolated from Iris for the first time.

Abstract

Chemical constituents of the leaves of iris songarica. Wang, Xin; Qin, Minjian; Wu, Gang; Shu, Pan. Department of Traditional Chinese Medical Resources, China Pharmaceutical University, Nanjing, Peop. Rep. China. Zhongguo Yaoke Daxue Xuebao (2006), 37(3), 222-225. Publisher: Zhongguo Yaoke Daxue, CODEN: ZHYXE9 ISSN: 1000-5048. Journal written in Chinese. CAN 148:198871 AN 2007:783387 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The column of silica gel was employed for the isolation and purifn. of the compds. from Dryopteris sublaeta Ching et Hsu. The structures of the compds. were identified by physiochem. properties and spectral anal. Five compds. were isolated from the ether fraction of 70% acetone-exts., and their structures were identified as (2S)5,7-dihydroxy-6,8-dimethyl flavanone (demethoxymatteucinol) (I), (2S)5,7-dihydroxy-4'-methoxyl-6,8-dimethyl flavanone (matteucinol) (II), (2S)5,7,2'-trihydroxy-6,8-dimethyl flavanone (III), (2S)5,7,4'-trihydroxy-6,8-dimethyl-3'-methoxyl flavanone (IV), (2S)5-hydroxy-6,8-dimethyl-4'-methoxyl-7-O-β-D-glucosyl flavanone (V). All the compds. are isolated from the aerial part of this plant for the first time.

Abstract

Constituents of the aerial part of Dryopteris sublaeta ching et Hsu. Zheng, Xiaoke; Dong, Sanli; Feng, Weisheng. School of Basic Medical Sciences, Henan College of Traditional Chinese Medicine, Zhengzhou, Peop. Rep. China. Zhongguo Yaoxue Zazhi (Beijing, China) (2006), 41(7), 500-501, 540. Publisher: Zhongguo Yaoxue Zazhishe, CODEN: ZYZAEU ISSN: 1001-2494. Journal written in Chinese. CAN 148:246084 AN 2007:791213 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


compds. isolated from the stems of G. cowa were tested for cytotoxic activities.


flavanone

US 2006-757779P P 20060110Priority Application US 20070160688 A1 20070712 US 2007-652294 20070110 Patent No. Kind Date Application No. Date Patent Family Information

Use of flavonoids to increase blood serum levels of dehydroepiandrosterone. Marchewitz, Eric. (USA). U.S. Pat. Appl. Publ. (2007), 4pp. CODEN: USXXCO US 2007160688 A1 20070712 Patent written in English. Application: US 2007-652294 20070110. Priority: US 2006-757779 20060110. CAN 147:134491 AN 2007:763578 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Cellular DNA topoisomerase I is an important target in cancer chemotherapy. A chloroform ext. of the root barks of Cudrania tricuspidata showed an inhibitory effect on mammalian DNA topoisomerase I. The topoisomerase I inhibitory compd. was purified and identified as 2',5,7-trihydroxy-4',5'-(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbutyl) flavanone. The compd., temporarily designated as PKH-3, was shown to inhibit the activity of topoisomerase I with IC50 about 1.0 mM. Concn. of 10 μM PKH-3 caused 50% growth inhibition of human cancer cell U937. PKH-3-induced cell death was characterized with the cleavage of poly(ADP-ribose) polymerase (PARP) and pro-caspase 3. Furthermore, PKH-3 induced the fragmentation of DNA into multiples of 180 b.p. (an apoptotic DNA ladder), indicating that the inhibitor triggered apoptosis. This induction of apoptosis by PKH-3 was also confirmed using flow cytometry anal. Taken together, these results suggest that PKH-3 may function by inhibiting oncogenic disease, at least in part, through the inhibition of topoisomerase I activity.

Abstract

2',5,7-Trihydroxy-4',5'-(2,2-dimethylchromeno)-8-(3-hydroxy-3-methylbutyl) flavanone purified from Cudrania tricuspidata induces apoptotic cell death of human leukemia U937 cells. Rho, Yoon-Hwa; Yoon, Soo-Hyun; Kim, Eun-Kyung; Kang, Ji-Young; Lee, Byong-Won; Park, Ki-Hun; Bae, Young-Seuk. Department of Biochemistry, College of Natural Sciences, Kyungpook National University, Taegu, S. Korea. Natural Product Research, Part B: Bioactive Natural Products (2007), 21(7), 616-624. Publisher: Taylor & Francis Ltd., CODEN: NPRPEA Journal written in English. CAN 148:291747 AN 2007:778581 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new dihydroflavanoid was obtained from the root of Spiranthes australis (R. Brown) Lindl, a traditional Chinese medicinal herb. The structure was elucidated as (2S)-5,2',6'-trihydroxy-6-lavandulyl-4''-(γ,γ-dimethylallyl)-2'',2''-dimethylpyrano-[5'',6'':7,8]-flavanone by spectroscopic methods including UV, IR, HR-EI-MS, ESI-MS, 1D NMR and 2D NMR techniques, and subsequently, the anticancer activities of the compd. to inhibit human cancer cell growth including A549, BEL-7402, SGC-7901, MCF-7, HT-29, K562, and A498 cell lines by MTT method was evaluated in vitro.

Abstract


flavanone

CN 2005-10097522 T0 20051228Priority Application AU 2006201584 A1 20071101 AU 2006-201584 20060413 JP 2007269650 A 20071018 JP 2006-94911 20060330US 20070232534 A1 20071004 US 2006-393619 20060330


EP 1834952 A1 20070919 EP 2006-251426 20060317CN 1990480 A 20070704 CN 2005-10097522 20051228Patent No. Kind Date Application No. Date Patent Family Information

Prenyl flavanone compounds for promoting neural stem cells growth. Huang, Chung-Yang; Chen, Chien-Nan; Ho, Wan-Ju. (Naturewise Biotech and Medicals Corporation, Taiwan). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 30pp. CODEN: CNXXEV CN 1990480 A 20070704 Patent written in Chinese. Application: CN 1009-7522 20051228. Priority: . CAN 147:203967 AN 2007:750096 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This paper aims to study the chem. constituents of Patrinia villosa Juss. Solvent extn., silica gel column and preparative liq. chromatog. were used to sep. the chem. constituents, and the chem. structures were elucidated by physico-chem. properties and spectra data. Eight compds. were isolated and identified as bolusanthol B(1), (2S)- 5, 7, 2', 6' -tetrahydroxy-6, 8-di(χ, χ-dimethylallyl) flavanone(2), orotinin(3), (2S)-5, 7, 2', 6'-tetrahydroxy-6-lavandulylated flavanone(4), 3'-prenyl-apigenine(5), luteolin(6), quercetin(7) and apigenin(8). Compd. 2 and 4 were new compds.; compds. 1, 3 and 5 were sepd. from Patrinia genus for the first time; compds. 6, 7 and 8 were isolated from Patrinia villosa Juss for the first time.

Abstract

Isolation and structure identification of chemical constituents from Patrinia villosa. Peng, Jinyong; Fang, Guorong; Wu, Yutian. Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep. China. Yaoxue Xuebao (2006), 41(3), 236-240. Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in Chinese. CAN 148:222242 AN 2007:755967 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method is disclosed for increasing blood serum levels of dehydroepiandrosterone by administering the combination of one of a flavonoid, isoflavonoid, coumarin and a flavonolignan; dehydroepiandrosterone; and a plant ext.

Abstract


flavanone

Abstract

Iodine/MeOH as a novel and versatile reagent system for the synthesis of α-ketothiocyanates. Yadav, J. S.; Reddy, B. V. Subba; Reddy, U. V. Subba; Krishna, A. D. Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad, India. Tetrahedron Letters (2007), 48(30), 5243-5246. Publisher: Elsevier Ltd., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN 147:322660 AN 2007:719547 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Five geranyl flavonoids, one prenylated flavonoid, and a simple flavanone were isolated from an ethanolic ext. of P. tomentosa fruit. Tomentodiplacol (1), 3'-O-methyl-5'-methoxydiplacol (2), 6-isopentenyl-3'-O-methyltaxifolin (3), and dihydrotricin (4) are reported from a natural source for the 1st time and 3'-O-methyldiplacone (6) for the 1st time from the genus Paulownia. The structures of the compds. were detd. by mass spectrometry, including HR-MS, and by 1D and 2D NMR spectroscopy. The cytotoxicity and DPPH (2,2-diphenyl-1-picrylhydrazyl)-quenching activity of some of these compds. were tested, with diplacone proving to be the best antioxidant, although the most cytotoxic compd.

Abstract

C-Geranyl Compounds from Paulownia tomentosa Fruits. Smejkal, Karel; Grycova, Lenka; Marek, Radek; Lemiere, Filip; Jankovska, Dagmar; Forejtnikova, Hana; Vanco, Jan; Suchy, Vaclav. Department of Natural Drugs and Department of Chemical Drugs, University of Veterinary and Pharmaceutical Sciences Brno, Brno, Czech Rep. Journal of Natural Products (2007), 70(8), 1244-1248. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 147:318278 AN 2007:748581 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OOH

OH O

OH

2R

R3

R1

R5

R6

4R

R7

I

The prenyl flavanone compds. are shown as chem. structure formula in claim 1, I; R1 is H, hydroxy, linear or branched alkyl with 1-3 C atom, or isoprene; R2, R3, R4, R5, R6 and R7 is H, hydroxy, linear or branched alkyl with 1-3 C atom, isoprene or geranyl shown as structures in claim 2 resp. Title prenyl flavanone compds. for promoting neural stem cells growth is used to prepg. medicinal compn. together with culture additive, growth factor etc.

Abstract


flavanone


A series of NH2-SBA-15 were prepd. via a aminopropyl-triethoxysilane to react with SBA-15 and characterized with N2-BET, XRD, elementary anal. and FTIR and flavanone was synthesize via condensation between 2'-hydroxyphenyl Me ketone and benzaldehyde catalyzed by the catalyst NH2-SBA-15. The microcalorimetric technique was used to study quant. the surface base sites of NH2-SBA-15 with intensity, no. and distribution. It was shown that the reaction condition (550,6,1.5) was the most compatible for synthesis of NH2-SBA-15.

Abstract

Application of microcalorimetric technique to the synthesis of NH2-SBA-15. Yang, Xu-Wei; Zhang, Xiao-Feng; Kan, Qiu-Bin; Fu, Wei; Huang, Jia-Hui; Wu, Tong-Hao. Department of Physic Chemistry, College of Chemistry, Jilin University, Changchun, Peop. Rep. China. Gaodeng Xuexiao Huaxue Xuebao (2007), 28(6), 1147-1150. Publisher: Gaodeng Jiaoyu Chubanshe, CODEN: KTHPDM ISSN: 0251-0790. Journal written in Chinese. CAN 147:372732 AN 2007:711674 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Increasing concern is being shown by the scientific community, government regulators, and the public about endocrine-disrupting chems. that are adversely affecting human and wildlife health through a variety of mechanisms. There is a great need for an effective means of rapidly assessing endocrine-disrupting activity, esp. estrogen-simulating activity, because of the large no. of such chems. in the environment. In this study, quant. structure activity relationship (QSAR) models were developed to quickly and effectively identify possible estrogen-like chems. based on 232 structurally-diverse chems. (training set) by using several nonlinear classification methodologies (least-square support vector machine (LS-SVM), counter-propagation artificial neural network (CP-ANN), and k nearest neighbor (kNN)) based on mol. structural descriptors. The models were externally validated by 87 chems. (prediction set) not included in the training set. All three methods can give satisfactory prediction results both for training and prediction sets, and the most accurate model was obtained by the LS-SVM approach through the comparison of performance. In addn., our model was also applied to about 58,000 discrete org. chems.; about 76% were predicted not to bind to estrogen receptor. The obtained results indicate that the proposed QSAR models are robust, widely applicable and could provide a feasible and practical tool for the rapid screening of potential estrogens.

Abstract

In silico screening of estrogen-like chemicals based on different nonlinear classification models. Liu, Huanxiang; Papa, Ester; Walker, John D.; Gramatica, Paola. Department of Structural and Functional Biology, QSAR Research Unit in Environmental Chemistry and Ecotoxicology, University of Insubria, Varese, Italy. Journal of Molecular Graphics & Modelling (2007), 26(1), 135-144. Publisher: Elsevier Inc., CODEN: JMGMFI ISSN: 1093-3263. Journal written in English. CAN 147:399612 AN 2007:718388 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Ketones possessing α-hydrogens undergo thiocyanation with ammonium thiocyanate in the presence of mol. iodine in refluxing methanol to produce the corresponding α-ketothiocyanates in excellent yields with high selectivity. The use of iodine makes this procedure simple, convenient and cost effective.


flavanone

The identification of optimal genotypes that result in improved prodn. of recombinant metabolites remains an engineering conundrum. In the present work, various strategies to re-engineer central metab. in Escherichia coli were explored for robust synthesis of flavanones, the common precursors of plant flavonoid secondary metabolites. Augmentation of the intracellular malonyl CoA

Abstract

Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Leonard, Effendi; Lim, Kok-Hong; Saw, Phan-Nee; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2007), 73(12), 3877-3886. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 147:275782 AN 2007:707344 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

Me

O

OHC

OH

O

OH

R4

R3

R5

6

7

R

R

R5

6

7

R

R

R4

R3

R4

R3

R5

6

7

R

R

I

IV

III

II

A synthesis of flavanones I [R3 = R4 = R5 = R6 = R7 = H; R3 = H, R4 = Cl, R5 = R6 = R7 = H; R3 = H, R4 = OMe, R5 = R6 = R7 = H; R3 = R4 = OMe, R5 = R6 = R7 = H; R3 = R4 = R5 = R6 = H, R7 = OMe; R3 = H, R4 = Cl, R5 = R6 = H, R7 = OMe; R3 = H, R4 = OMe, R5 = R6 = H, R7 = OMe; R3 = R4 = R5 = H, R6 = OMe, R7 = H; R3 = H, R4 = Cl, R5 = H, R6 = OMe, R7 = H; R3 = H, R4 = OMe, R5 = H, R6 = OMe, R7 = H; R3 = R4 = H, R5 = OMe, R6 = R7 = H; R3 = H, R4 = OMe, R5 = OMe, R6 = R7 = H] was achieved via aldol addn. reactions of corresponding acetophenones II and benzaldehydes III using LDA in THF followed by treatment of the reaction mixts. with a satd. NH4Cl soln. and subsequent intramol. cyclocondensation reactions of the resulting alcs. IV using PPh3 and DEAD in CH2Cl2.

Abstract

A novel synthesis of flavanones from 2-hydroxybenzoic acids. Lee, Jae In; Jung, Mi Gung; Jung, Hye Jin. Department of Chemistry/Plant Resources Research Institute, College of Natural Science, Duksung Women's University, Seoul, S. Korea. Bulletin of the Korean Chemical Society (2007), 28(5), 859-862. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN: 0253-2964. Journal written in English. CAN 148:355538 AN 2007:709690 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Flavonoids and stilbenes have attracted much attention as potential targets for nutraceuticals, cosmetics, and pharmaceuticals. We Abstract

Synthesis of Unnatural Flavonoids and Stilbenes by Exploiting the Plant Biosynthetic Pathway in Escherichia coli. Katsuyama, Yohei; Funa, Nobutaka; Miyahisa, Ikuo; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of Agriculture and Life Sciences, University of Tokyo, Bunkyo-ku, Tokyo, Japan. Chemistry & Biology (Cambridge, MA, United States) (2007), 14(6), 613-621. Publisher: Cell Press, CODEN: CBOLE2 ISSN: 1074-5521. Journal written in English. CAN 147:540144 AN 2007:687350 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Title cosmetics, which show synergistic melanin formation inhibiting action and prevent or treat UV-induced pigmentation, freckles, liver spot, etc., contain (a) the menthol esters and (b) inhibitors for keratinocyte-derived hormones, antioxidants, inflammation inhibitors, or polyols . Thus, NADPH inhibited thioredoxin/ADF prodn. by human keratinocyte. Application of a cream contg. menthol linoleate (prepn. given), NADPH, and sunflower ext. to female volunteers reduced spots.


Melanin formation inhibiting cosmetics containing esters of menthol with C≥18 unsaturated fatty acid esters and keratinocyte-derived hormone inhibitors, etc. Tanaka, Hiroshi. (Narisu Cosmetic Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2007), 20pp. CODEN: JKXXAF JP 2007161591 A 20070628 Patent written in Japanese. Application: JP 2005-355769 20051209. Priority: . CAN 147:124622 AN 2007:702220 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(malonyl-CoA) pool through the coordinated overexpression of four acetyl-CoA carboxylase (ACC) subunits from Photorhabdus luminescences (PlACC) under a constitutive promoter resulted in an increase in flavanone prodn. up to 576%. Exploration of macromol. complexes to optimize metabolic efficiency demonstrated that auxiliary expression of PlACC with biotin ligase from the same species (BirAPl) further elevated flavanone synthesis up to 1,166%. However, the coexpression of PlACC with Escherichia coli BirA (BirAEc) caused a marked decrease in flavanone prodn. Activity improvement was reconstituted with the coexpression of PlACC with a chimeric BirA consisting of the N terminus of BirAEc and the C terminus of BirAPl. In another approach, high levels of flavanone synthesis were achieved through the amplification of acetate assimilation pathways combined with the overexpression of ACC. Overall, the metabolic engineering of central metabolic pathways described in the present work increased the prodn. of pinocembrin, naringenin, and eriodictyol in 36 h up to 1,379%, 183%, and 373%, resp., over prodn. with the strains expressing only the flavonoid pathway, which corresponded to 429 mg/L, 119 mg/L, and 52 mg/L, resp.


flavanone

Answer 202:

Flavones are important copigments found in the flowers of many higher plants and play a variety of roles in plant adaptation to stress. In Medicago species, flavones also act as signal mols. during symbiotic interaction with the diazotropic bacterium Sinorhizobium meliloti. They are the most potent nod gene inducers found in root exudates. However, flavone synthase II (FNS II), the key enzyme responsible for flavone biosynthesis, has not been characterized in Medicago species. We cloned two FNS II genes from Medicago truncatula using known FNS II sequences from other species and named them MtFNSII-1 and MtFNSII-2. Functional assays in yeast (Saccharomyces cerevisiae) suggested that the catalytic mechanisms of both cytochrome P 450 monooxygenases were similar to the other known legume FNS II from licorice (Glycyrrhiza echinata). MtFNSII converted flavanones to 2-hydroxyflavanones instead of flavones whereas FNS II from the nonlegume Gerbera hybrida, converted flavanones to flavones directly. The two MtFNSII genes had distinct tissue-specific expression patterns. MtFNSII-1 was highly expressed in roots and seeds whereas MtFNSII-2 was highly expressed in flowers and siliques. In addn., MtFNSII-2 was inducible by S. meliloti and Me jasmonate treatment, whereas MtFNSII-1 was not. Histochem. staining of transgenic hairy roots carrying the promoter-reporter constructs indicated that the MtFNSII-2 induction was tissue specific, mostly localized to vascular tissues and root hairs. RNA interference-mediated suppression of MtFNSII genes resulted in flavone depleted roots and led to significantly reduced nodulation when inoculated with S. meliloti. Our results provide genetic evidence supporting that flavones are important for nodulation in M. truncatula.

Abstract

Flavone synthases from Medicago truncatula are flavanone-2-hydroxylases and are important for nodulation. Zhang, Juan; Subramanian, Senthil; Zhang, Yansheng; Yu, Oliver. Donald Danforth Plant Science Center, St. Louis, MO, USA. Plant Physiology (2007), 144(2), 741-751. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 147:228128 AN 2007:682642 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new flavone, 7-hydroxy-5-methoxy-6,8-dimethylflavone, was synthesized in 91% yield by treating of 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (1) with DMSO/I2. Two other flavonoids, 7-hydroxy-5-methoxy-6,8-dimethylflavanone and 5,7-dihydroxy-6,8-dimethylflavanone, were obtained from 1 in HCl/MeOH soln. in 70% and 20% yield, resp.

Abstract

Synthesis of new flavonoids from 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone. Zhang, Jian-feng; Jiang, Feng; Zhou, Xiong. State Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical Engineering, Ningbo University, Ningbo, Peop. Rep. China. Hecheng Huaxue (2007), 15(3), 319-321, 349. Publisher: Hecheng Huaxue Bianjibu, CODEN: HEHUE2 ISSN: 1005-1511. Journal written in English. CAN 148:471736 AN 2007:684328 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


have developed a system for producing "unnatural" flavonoids and stilbenes in Escherichia coli. The artificial biosynthetic pathway included three steps. These included a substrate synthesis step for CoA esters synthesis from carboxylic acids by 4-coumarate:CoA ligase, a polyketide synthesis step for conversion of the CoA esters into flavanones by chalcone synthase and chalcone isomerase, and into stilbenes by stilbene synthase, and a modification step for modification of the flavanones by flavone synthase, flavanone 3β-hydroxylase and flavonol synthase. Incubation of the recombinant E. coli with exogenously supplied carboxylic acids led to prodn. of 87 polyketides, including 36 unnatural flavonoids and stilbenes. This system is promising for construction of a larger library by employing other polyketide synthases and modification enzymes.


flavanone

High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). Grace, Philip B.; Mistry, Nayan S.; Carter, Megan H.; Leathem, Anthony J. C.; Teale, Philip. HFL, Cambridgeshire, UK. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2007), 853(1-2), 138-146. Publisher: Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal written in English. CAN 147:180438 AN 2007:656744 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids have been reported to be dietary antagonists of an aryl hydrocarbon receptor (AhR). However, little is known about the mol. mechanism on their antagonistic effects. In this study, the inhibitory effect of flavonoids on ligand binding to the AhR and interaction between flavonoids and the AhR complex (AhRc) were investigated in each flavonoid subclass. Flavone, flavonol, and flavanone but not catechin inhibited the specific binding between the AhR and 3-methylcholanthrene dose-dependently, indicating that the former three subclasses possibly act as competitive antagonists of the AhR. However, catechin in addn. to the former three subclasses directly interacted with the AhRc by surface plasmon resonance anal. The dissocn. const. values showed an inverse correlation with the suppressive effect on the DNA binding activity. These results suggest that flavone, flavonol, and flavanone act as competitive antagonists of the AhR, while catechin assocs. with the AhRc and indirectly exhibits its antagonistic effects.

Abstract

Interaction between the aryl hydrocarbon receptor and its antagonists, flavonoids. Fukuda, Itsuko; Mukai, Rie; Kawase, Masaya; Yoshida, Ken-ichi; Ashida, Hitoshi. Research Center for Food Safety and Security, Graduate School of Agricultural Science, Kobe University, Kobe, Hyogo, Japan. Biochemical and Biophysical Research Communications (2007), 359(3), 822-827. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 147:269152 AN 2007:658816 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The compn. of anthocyanins was analyzed in two rice cultivars. 'Ilpum' showed no detectable levels, while 'Heugjinju' contained three types of anthocyanins: cyanidin, cyanidin 3-O-glucoside, and peonidin 3-O-glucoside. We also assessed the expression of anthocyanin biosynthetic genes - for phenylalanine ammonia lyase (PAL), chalcone synthase (CHS), flavanone 3β-hydroxylase (F3H), dihydroflavonol reductase (DFR), and anthocyanin synthase (ANS) - in different tissues of those cultivars. All five genes were expressed more in the leaves and seeds of 'Heugjinju' than in 'Ilpum', with the greatest amt. of transcript being detected in 'Heugjinju' seeds. Two genes, DFR and ANS, had relatively high expression levels and were specific for anthocyanin biosynthesis. Furthermore, expression of CHS, F3H, DFR, and ANS was enhanced during seed maturation and was correlated with ambient temp. during seedling growth.

Abstract

Anthocyanin content in rice is related to expression levels of anthocyanin biosynthetic genes. Kim, Bong Gyu; Kim, Jeong Ho; Min, Shin Young; Shin, Kwang-Hee; Kim, Ji Hye; Kim, Hong Yeol; Ryu, Su Noh; Ahn, Joong-Hoon. Division of Bioscience and Biotechnology, Bio/Molecular Informatics Center, IBST, Seoul, S. Korea. Journal of Plant Biology (Seoul, Republic of Korea) (2007), 50(2), 156-160. Publisher: Botanical Society of Korea, CODEN: JPBIEZ ISSN: 1226-9239. Journal written in English. CAN 147:483096 AN 2007:676482 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Suppression subtractive hybridization identifies genes induced in response to UV-B irradiation in apple skin: isolation of a putative UDP-glucose 4-epimerase. Ban, Yusuke; Honda, Chikako; Bessho, Hideo; Pang, Xiao-Ming; Moriguchi, Takaya. Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, Japan. Journal of Experimental Botany (2007), 58(7), 1825-1834. Publisher: Oxford University Press, CODEN: JEBOA6 ISSN: 0022-0957. Journal written in English. CAN 147:318509 AN 2007:653116 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


To gain a better understanding of the tomato root response to waterlogging stress at protein level, a proteomic approach has been conducted in combination with physiol. analyses. Five-week old plants were subjected to waterlogging stress, and roots were collected 24 and 72 h after treatment. Waterlogging stress resulted in a gradual increase of lipid peroxidn. and in vivo H2O2 concn. in roots. To elucidate temporal changes in protein expression in tomato roots, proteins were extd. from the root samples, sepd. by 2-DE, and visualized by staining with Coomassie Brilliant Blue. A total of 35 proteins were differentially expressed in tomato roots in response to waterlogging stress, and 29 were identified using MALDI-TOF anal. Of the proteins identified, 16 proteins were up-regulated and 13 proteins were down-regulated in waterlogged tomato roots. In addn. to previously identified waterlogging-regulated proteins, we identified several novel proteins, including 3-beta-hydroxylase, phenylalanine ammonia-lyase, glutamyl-tRNA reductase, flavanone 3-hydroxylase, mitochondrial ATPase alpha subunit, cysteine protease, DWARF1, and NIM1-like protein 2. These newly identified proteins are involved in several cellular processes, including hormone and secondary metabolite synthesis, programmed cell death, and stress and defense mechanisms. Five differentially accumulated proteins were further analyzed at the mRNA level, which confirmed the differential gene expression, and revealed that the transcript levels were not always consistent with the translation level. The identification of these novel proteins in the waterlogging stress response provides new insight that can lead to a better understanding of the mol. basis of waterlogging-sensitivity in plants.

Abstract

A proteomic screen and identification of waterlogging-regulated proteins in tomato roots. Ahsan, Nagib; Lee, Dong-Gi; Lee, Sang-Hoon; Lee, Ki-Won; Bahk, Jeong Dong; Lee, Byung-Hyun. Division of Applied Life Sciences (BK21 program), Gyeongsang National University, Jinju, S. Korea. Plant and Soil (2007), 295(1-2), 37-51. Publisher: Springer, CODEN: PLSOA2 ISSN: 0032-079X. Journal written in English. CAN 147:296133 AN 2007:656077 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytoestrogens are currently the subject of intense study owing to their potential protective effects against a no. of complex diseases. However, in order to investigate the interactions between phytoestrogens and disease state effectively, it is necessary to have anal. methods which are sensitive, reproducible, and require low sample vols. The authors report an assay for 3 isoflavones (daidzein, genistein, and glycitein), 2 metabolites of daidzein (equol and O-desmethylangolensin), 3 lignans (secoisolariciresinol, enterodiol, and enterolactone), and 1 flavanone (naringenin) in human urine and serum. A high throughput of samples has been achieved via the use of 96-well plate sample extn. and liq. chromatog./tandem mass spectrometry (LC-MS/MS) anal. incorporating column switching, thus making the assay suitable for use on large sample nos., such as those found in epidemiol. studies. The robustness of the assay was proven via the comparison of data generated on two different LC-MS/MS systems, with and without column switching.

Abstract


flavanone

A HPLC system for the chiral sepn. is presented allowing the parallel simultaneous testing of 8 chiral columns with different mobile phases. The immobilized chiral stationary phases are based on aryl carbamate and benzoate derivs. of cellulose and amylose. The

Abstract

Multiparallel chiral separation screening. Screening of chiral stationary and mobile phases. Francotte, Eric; Huynh, Dan; Wetli, Herbert A. Novartis Institutes for BioMedical Research, Basel, Switz. GIT Labor-Fachzeitschrift (2006), 50(5), 452-455. Publisher: GIT Verlag GmbH & Co. KG, CODEN: GLFAF5 Journal written in German. CAN 147:102352 AN 2007:650107 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


UV A (UV-A)-mediated regulation of anthocyanin biosynthesis was investigated in swollen hypocotyls of the red turnip 'Tsuda'. The shaded swollen hypocotyls which contained negligible anthocyanin were exposed to artificial light sources including low fluence UV-B, UV-A, blue, red, far-red, red plus UV-A, far-red plus UV-A, and blue plus red. Among these lights, only UV-A induced anthocyanin biosynthesis and co-irradn. of red or far-red with UV-A did not affect the extent of UV-A-induced anthocyanin accumulation. The expression of phenylalanine ammonia lyase (PAL; EC 4.3.1.5), chalcone synthase (CHS; EC 2.3.1.74), flavanone 3-hydroxylase (F3H; EC 1.14.11.9), dihydroflavonol 4-reductase (DFR; EC 1.1.1.219), and anthocyanidin synthase (ANS; EC 1.14.11.19) genes was increased with time during a 24 h exposure to UV-A. In contrast, irradn. with red, blue, UV-B, and a combination of blue with red failed to induce CHS expression. Microarray anal. showed that only a few genes, including CHS and F3H, were induced significantly by UV-A, while a sep. set of many genes was induced by low fluence UV-B. The UV-A-specific induction of anthocyanin biosynthesis and the unique gene expression profile upon UV-A irradn. as compared with blue and UV-B demonstrated that the obsd. induction of anthocyanin biosynthesis in red turnips was mediated by a distinct UV-A-specific photoreceptor, but not by phytochromes, UV-A/blue photoreceptors, or UV-B photoreceptors.

Abstract

Ultraviolet A-specific induction of anthocyanin biosynthesis in the swollen hypocotyls of turnip (Brassica rapa). Zhou, Bo; Li, Yuhua; Xu, Zhiru; Yan, Haifang; Homma, Shinichiro; Kawabata, Saneyuki. College of Life Sciences, Northeast Forestry University, Harbin, Peop. Rep. China. Journal of Experimental Botany (2007), 58(7), 1771-1781. Publisher: Oxford University Press, CODEN: JEBOA6 ISSN: 0022-0957. Journal written in English. CAN 147:296237 AN 2007:653111 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Suppression subtractive hybridization (SSH) successfully identified 11 cDNAs in apple skin with highly induced expression as a result of UV-B irradn. Apart from three putative flavonoid biosynthetic genes, chalcone synthase (CHS; A5C), flavanone-3-hydroxylase (F3H; B5F), and flavonol synthase (FLS; D1F), five clones (A1H, A10E, B11G, D5F, and D11H) were induced by low temp. (17°) as well, which is also known to induce anthocyanin accumulation in apple skin. Moreover, four clones (A1H, A10E, B11G, and D11H), showing higher expression levels in the skin, accumulated higher anthocyanin concns. than their counterparts. Of the four clones, only A10E, a putative UDP-glucose 4-epimerase (UGE), was deemed to play an important role in anthocyanin accumulation in apple skin based on the facts that:. (i) its transcription level was higher in the deep red cultivar, 'Jonathan', than in the pale red cultivar, 'Tsugaru'; and. (ii) it could reversibly catalyze UDP-glucose to UDP-galactose, and the latter mol. is a major sugar donor for cyanidin-glycoside in apple. Therefore, the full-length cDNA of A10E was isolated by rapid amplification of cDNA ends (RACE) and designated as MdUGE1. Further anal. demonstrated that UGE enzymic activity was pos. correlated with anthocyanin accumulation in apple skin. Thus, MdUGE1 isolated by SSH could play an important role in anthocyanin biosynthesis in apple skin in concert with other flavonoid biosynthetic genes.


flavanone

Natural non-enzymic-antioxidants (vitamin E, polyphenols and flavonoids) prevent overprodn. of reactive oxygen species playing important role in oxidative-stress-mediated diseases. To improve potential use of natural compds. we need to explore mechanism of their action. Structure-activity-relationship (SAR) of flavonoids was studied in details. However, only a few data are known regarding SAR of flavonolignans such as (+)-silybin (1a,b). Previously, we demonstrated that (+)-silybin (1a,b) suppressed superoxide anion prodn. (O2⋅-) prodn. in phorbol-myristate-acetate (PMA) stimulated polymorphonuclear leukocytes (PMNLs) via inhibition of protein kinase C (PKC) activity and an increase in its lipid soly. (1a,b → 5a,b) improves its effect. Removal of 3'-methoxy-4'-hydroxyphenyl and hydroxyl group at ring C of 1a,b resulting in flavanone derivs. did not modify, while introduction of a double bond in ring C improved its inhibition on PMNLs. Silybum marianum contains beside (+)-silybin (1a,b), its regioisomer (+)-isosilybin (2a,b). Little is known about the effect of this structural modification on the antioxidant activity of mol. Therefore, several flavanone and flavone analogs of (+)-silybin (1a,b) and (+)-isosilybin (2a,b) were synthesized removal of 3'-methoxy-4'-hydroxyphenyl group at ring D and

Abstract

Relationship of structure and antioxidant activity of synthetic silybin- and isosilybin derived molecules: identification of molecular structure responsible for antioxidant activity employing various models for inducing oxidative stress. Varga, Zsuzsa; Nagy, Emoke; Katko, Monika; Jeney, Viktoria; Ujhelyi, Laszlo; Seres, Ildiko; Paragh, Gyorgy; Balla, Jozsef; Antus, Sandor. Division of Nephrology, University of Debrecen, Hung. Editor(s): Panglossi, Harold V. New Developments in Antioxidants Research (2006), 113-151. Publisher: Nova Science Publishers, Inc., Hauppauge, N. Y CODEN: 69JGNB Conference written in English. CAN 147:203859 AN 2007:630786 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The time evolution of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.bul.) concn. in four solvents (methanol, ethanol, propanol, and acetonitrile) during its redn. by three flavanones contg. an isolated p-catechol group (taxifolin, eriodyctiol, and fustin) as well as the time evolution of the mass spectra of the reaction mixt. has been detd. by spectrophotometry and liq. mass spectrometry, resp. In alc. solvents the redn. curves consisted of an initial short but fast kinetics step followed by a longer slow kinetics step; in contrast, in acetonitrile the redn. curves completely lacked the slow kinetics step. From the results, a kinetic model for the reaction of redn. of the DPPH.bul. by the isolated p-catechol group in flavanone type structures is proposed. According to this model, the p-catechol group rapidly transfers two hydrogen atoms to DPPH.bul., through a fast rate const. k1, yielding the corresponding o-quinone. Then, the intermediate o-quinone forms an adduct with the alc. solvent, through a slow rate const. k2, and regenerates the p-catechol group. The regenerated p-catechol group reduces addnl. DPPH.bul. through a fast rate const. k3, yielding the corresponding o-quinone, which can form a new adduct with the solvent to regenerate the p-catechol group, and so on. From the kinetics model, two explicit kinetics equations have been derived that fit very well the exptl. data points acquired from all assayed compds. in all of the expts. carried out, thus allowing an accurate detn. of the corresponding rate and stoichiometric consts.

Abstract

Kinetic Model for the Antiradical Activity of the Isolated p-Catechol Group in Flavanone Type Structures Using the Free Stable Radical 2,2-Diphenyl-1-picrylhydrazyl as the Antiradical Probe. Sendra, Jose M.; Sentandreu, Enrique; Navarro, Jose L. Instituto de Agroquimica y Tecnologia de Alimentos, Burjassot, Spain. Journal of Agricultural and Food Chemistry (2007), 55(14), 5512-5522. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 147:165843 AN 2007:639641 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


configuration allows the test of 230 resp. 460 (chromatog. run of 40 resp. 15 min) conditions in 24 h. Conditions were found to sep. the enantiomers of racemic glutethimide and flavanone.


flavanone

Abstract

Two new flavonoids from Bonannia graeca: a DFT-NMR combined approach in solving structures. Rosselli, Sergio; Bruno, Maurizio; Maggio, Antonella; Bellone, Gabriella; Formisano, Carmen; Mattia, Carlo Andrea; Di Micco, Simone; Bifulco, Giuseppe. Dipartimento di Chimica Organica, Universita di Palermo, Palermo, Italy. European Journal of Organic Chemistry (2007), (15), 2504-2510. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: EJOCFK ISSN: 1434-193X. Journal written in English. CAN 147:207728 AN 2007:617775 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The genes MYB11, MYB12 and MYB111 share significant structural similarity and form subgroup 7 of the Arabidopsis thaliana R2R3-MYB gene family. To det. the regulatory potential of these three transcription factors, we used a combination of genetic, functional genomics and metabolite anal. approaches. MYB11, MYB12 and MYB111 show a high degree of functional similarity and display very similar target gene specificity for several genes of flavonoid biosynthesis, including CHALCONE SYNTHASE, CHALCONE ISOMERASE, FLAVANONE 3-HYDROXYLASE and FLAVONOL SYNTHASE1. Seedlings of the triple mutant myb11 myb12 myb111, which genetically lack a complete subgroup of R2R3-MYB genes, do not form flavonols while the accumulation of anthocyanins is not affected. In developing seedlings, MYB11, MYB12 and MYB111 act in an additive manner due to their differential spatial activity; MYB12 controls flavonol biosynthesis mainly in the root, while MYB111 controls flavonol biosynthesis primarily in cotyledons. We identified and confirmed addnl. target genes of the R2R3-MYB subgroup 7 factors, including the UDP-glycosyltransferases UGT91A1 and UGT84A1, and we demonstrate that the accumulation of distinct and structurally identified flavonol glycosides in seedlings correlates with the expression domains of the different R2R3-MYB factors. Therefore, we refer to these genes as PFG1-3 for 'Prodn. OF FLAVONOL GLYCOSIDES.

Abstract

Differential regulation of closely related R2R3-MYB transcription factors controls flavonol accumulation in different parts of the Arabidopsis thaliana seedling. Stracke, Ralf; Ishihara, Hirofumi; Huep, Gunnar; Barsch, Aiko; Mehrtens, Frank; Niehaus, Karsten; Weisshaar, Bernd. Department of Biology, Genome Research, Bielefeld University, Bielefeld, Germany. Plant Journal (2007), 50(4), 660-677. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 147:296233 AN 2007:624079 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


in case of the basic skeleton (rac.-9) of (+)-silybin (1a,b), suggesting that this skeleton is the binding site for PKC. Inhibition of xanthine oxidase activity was the most pronounced in case of flavone analogs of 1a,b (rac.-10) and 2a,b (rac.-11), and silybin-like derivs. were more potent than isosilybin-like ones. Silybin (1a,b), and flavone analogs of silybin (rac.-10) and isosilybin (rac.-11) enhanced markedly oxidative resistance of LDL, and there were no differences between the action of silybin and isosilybin analogs. In summary, these results suggest that different moieties of (+)-silybin (1a,b) and (+)-isosilybin (2a,b) are responsible for the antioxidant action in PMA stimulated PMNLs, xanthine oxidase activity, and LDL oxidn.

hydroxyl group at ring C of 1a,b and 2a,b resulted in flavanone derivs. of racemic (rac.-7 and -8) and optically active form [(-)-7 and -8]; introduction of a double bond in rac.-7 and -8 served the corresponding flavone derivs. rac.-10 and -11, and basic skeleton (rac-9) - and their antioxidant activities were compared. We found that both series of derivs. (rac.-7 vs. rac.-8, (-)-7 vs. (-)-8 and rac.-10 vs. rac.-11) have almost same effects on O2⋅- prodn. in PMA-stimulated neutrophils, but flavone analogs (rac.-10, -11) have been found to be more active ones via inhibition of PKC activity. The highest inhibition in PKC activity of PMA-stimulated neutrophils has been obsd.


flavanone

Synthesis and antimicrobial activities of some new flavanones from 3,4-methylenedioxybenzaldehyde. Kadu, M. V.; Bibliographic Information Answer 215:

In order to make use of the resources of Ficus benghalensis silk and to avoid wasting, the extn. of total flavanone of Ficus benghalensis silk and its effects on scavenging of hydroxyl radicals were studied. The flavonoids were extd. using ethanol petroleum ether or water as solvent from Ficus benghalensis silk under ultrasonic radiation. Using spectrophotometry to analyze the flavanone of Ficus benghalensis silk, the d. of the total flavanone was 0.7240 mg/mL, 0.5962 mg/mL and 0.4529 mg/mL, resp., and the rate of recovery were 101.0%, 99.8% and 100.9%. The rate of prodn. of ethanol extn. was the highest. The effect of the exts. on scavenging of hydroxyl radicals was studied. This method is a purely phys. process and does not cause any pollution. It is an ideal way to ext. the flavanone of Ficus benghalensis silk.

Abstract

Extracting of total flavanone from Ficus benghalensis silk and its effect on scavenging of hydroxyl radicals. Huang, Suoyi; Jiang, Lifang; Liu, Haihua; Li, Rong. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Peop. Rep. China. Huaxue Shijie (2006), 47(11), 689-691, 646. Publisher: Shanghaishi Huaxue Huagong Xuehui, CODEN: HUAKAB ISSN: 0367-6358. Journal written in Chinese. CAN 147:360667 AN 2007:612936 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This article explores the use of capillary electrochromatog. for the anal. of chamomile (Chamomilla recutita L.) exts. After a thorough study of anal. parameters such as mobile and stationary phase compn., applied voltage, and temp., a methodol. to det. 11 bioactive phenolic compds. (coumarins: herniarin, umbelliferone; phenylpropanoids: chlorogenic acid, caffeic acid; flavones: apigenin, apigenin-7-O-glucoside, luteolin, luteolin-7-O-glucoside; flavonols: quercetin, rutin and flavanone: naringenin) in chamomile exts. was proposed. The method was performed in a Hypersil SCX/C18 column with pH 2.8 phosphate buffer at 50 mmol L-1 contg. 50% acetonitrile (pH adjusted before the addn. of the org. solvent). All compds. were sepd. in less than 7.5 min under isocratic conditions. Figures of merit include linearity (peak area vs. apigenin concn.) from 50.0-1000 μg/mL (r2 = 0.995), and intra-day precision of retention time and peak area better than 1.3% CV and 15%, resp. The limits of detection and quantification for apigenin were 35.0 μg/mL and 150.0 μg/mL, resp. This article also describes an NMR 1H study, carried out to monitor a new clean-up procedure for exts. contg. propyleneglycol, whose components are poorly retained in conventional octadecyl silica cartridges.

Abstract

Capillary electrochromatography of selected phenolic compounds of Chamomilla recutita. Fonseca, Fabiana N.; Tavares, Marina F. M.; Horvath, Csaba. Institute of Chemistry, University of Sao Paulo, Sao Paulo, SP, Brazil. Journal of Chromatography, A (2007), 1154(1-2), 390-399. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 147:126354 AN 2007:617116 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new cyclized C-geranylated flavonoids, the dihydroflavonol bonanniol C and the flavanone bonannione B, were isolated as minor compds. from the aerial parts. of B. graeca (Umbelliferae). Their structures were elucidated by a combined approach of extensive spectroscopic means and quantum mech. methods.


flavanone

A review. Litchi (Litchi chinensis Sonn.) is a tropical to subtropical crop that originates in South-east Asia. Litchi fruit pericarp tissue contains large amt. of pigments which contribute the attractive red skin. However, the fruit lose rapidly the red color after harvest. Postharvest handling has been emphasized on the control of the pigment degrdn. Storage of modified atmospheres in plastic bags and sealed containers or controlled atmospheres has been reported to inhibit pigment degrdn. and reduce pericarp browning in litchi fruit. The major pigments in ripe litchi fruit pericarp include flavonols, flavones, flavanones and anthocyanins. The major flavonoids are detd. to be proanthocyanidin B4, proanthocyanidin B2 and epicatechin while cyanindin-3-rutinside, cyanidin-3-glucoside, quercetin-3-rutinosde and quercetin-3-glucoside are identified as the important colored anthocyanins. Litchi pigments exhibit a strong antioxidant capability. The hydroxyl radical and superoxide anion scavenging activities of proanthocyanidin B2 is greater than those of proanthocyanidin B4 and epicatechin while the epicatechin has the highest DPPH scavenging activity. In similarity to the antioxidant activity, litchi fruit pericarp ext. demonstrates a dose- and time-dependent inhibitory effect on human breast cancer. Furthermore, the anti-cancer activities of epicatechin, proanthocyanidin B2, proanthocyanidin B4 and the Et acetate fraction from litchi pericarp tissues are obsd. In in vitro trials of MCF-7 and HELF proliferation, proanthocyanidin B4 and the Et acetate fraction show a stronger inhibitory

Abstract

Identification, property and biological activity of the pigments of harvested litchi fruit. Jiang, Yueming; Li, Jianrong; Zhao, Mouming; Shi, John. South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, Peop. Rep. China. Editor(s): Benkeblia, Noureddine; Shiomi, Norio. Advances in Postharvest Technologies for Horticultural Crops (2006), 341-352. Publisher: Research Signpost, Trivandrum, India CODEN: 69JFYJ Conference; General Review written in English. CAN 147:485110 AN 2007:594731 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A Streptomyces strain, SPRI 94166, producing herbicidally active substances, was isolated from soil samples collected in Guangxi Province. Based on morphol., physiol., and biochem. as well as mol. biol. characteristics, SPRI 94166 was identified as Streptomyces lavendulae. Three active compds. were sepd. after isolation from the fermn. broth of strain SPRI 94166. Using NMR, and IR and mass spectroscopy anal. methods, these compds. were identified as 4',5,7-trihydoxyisoflavone, flavanone and quercetin.

Abstract

Herbicidal activity of microbially produced flavanoids. Tao, Liming; Gu, Xuebin; Wang, Weijiong; Yang, Xing; Zhang, Yulian; Xu, Wenping. Shanghai Pesticide Research Institute, Shanghai, Peop. Rep. China. Nongyao (2006), 45(3), 180-181, 203. Publisher: Nongyao Bianjibu, CODEN: NONGFP ISSN: 1006-0413. Journal written in Chinese. CAN 148:208139 AN 2007:598045 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Some new flavanone derivs. have been prepd. by condensation of 1,3-propanediones with 3,4-methylenedioxybenzaldehyde (piperonal) in alk. ethanol. The structures of these compds. have been confirmed by spectral anal. IR and NMR etc. The antimicrobial activities of these compds. have been assessed against test organisms and were compared with std. drug chloramphenicol.

Abstract

Khadsan, R. E. Department of Applied Chemistry, Anuradha Engineering College, Chikhli, India. Journal of Ultra Scientist of Physical Sciences (2007), 19(1), 89-92. Publisher: Journal of Ultra Scientist of Physical Sciences, CODEN: JUSPB3 Journal written in English. CAN 148:410013 AN 2007:598850 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


Four new flavanone oligoglycosides, theaflavanosides I, II, III, and IV, were isolated from the seeds of C. sinensis. The structures of theaflavanosides were elucidated on the basis of chem. and physicochem. evidence. Among them, theaflavanoside III was found to show hepatoprotective effect on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes.

Abstract

New flavanone oligoglycosides, theaflavanosides I, II, III, and IV, with hepatoprotective activity from the seeds of tea plant (Camellia sinensis). Li, Ning; Morikawa, Toshio; Matsuda, Hisashi; Ninomiya, Kiyofumi; Li, Xian; Yoshikawa, Masayuki. Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto, Japan. Heterocycles (2007), 71(5), 1193-1201. Publisher: Japan Institute of Heterocyclic Chemistry, CODEN: HTCYAM ISSN: 0385-5414. Journal written in English. CAN 147:138396 AN 2007:563166 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The compn. comprises flavonoids, preferably flavanone glycosides (bioflavonoids) and fruit org. acids, preferably ascorbic, malic or citric acids, which may be partially neutralised with 2-hydroxyethyltrimethyl ammonium hydroxide (choline) base. Preferably the flavonoid and acid are dissolved in a non-toxic solvent mixt. comprising water and a co-solvent glycerin, polyhydric alcs. A preferred embodiment comprises 15% sol. bioflavonoid, 15% citric acid, 15% malic acid, 5% ascorbic acid, 15% aq. soln. choline (45%n soln.), 15% glycerin, 20% water.

Abstract GB 2005-24375 20051129Priority Application GB 2432528 A 20070530 GB 2005-24375 20051129 Patent No. Kind Date Application No. Date Patent Family Information

Use of flavonoids and fruit acid as anti-viral compositions. Ripley, Ian. (UK). Brit. UK Pat. Appl. (2007), 9pp. CODEN: BAXXDU GB 2432528 A 20070530 Patent written in English. Application: GB 2005-24375 20051129. Priority: . CAN 146:528354 AN 2007:583200 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


effect on HELF than MCF-7 while epicatechin and proanthocyanidin B2 have lower cytotoxicities to MCF-7 and HELF than paclitaxel. It is suggested that the constituents from litchi fruit pericarp tissues might serve as a powerful novel anti-tumor agent but need to be investigated further.


flavanone

Answer 222:

O

O

MeO

OMe

I

An efficient and economical synthesis of the naturally occurring aromatase inhibitor abyssinone II was performed. The synthesis features an optimized arom. prenylation reaction in which an arylcopper intermediate is reacted with prenyl bromide to afford a key intermediate that was converted to a prenylated arom. aldehyde. Condensation of the aldehyde with an o-hydroxyacetophenone under Claisen-Schmidt conditions afforded a chalcone that was deprotected and cyclized in the presence of sodium acetate in refluxing ethanol to afford (±)-abyssinone II. The synthesis proved to be versatile enough to provide an array of abyssinone II derivs. that were evaluated as aromatase inhibitors. Methylation of the 4'-hydroxyl group of (±)-abyssinone II resulted in a significant increase in aromatase inhibitory activity, and further smaller increases in activity resulted from the methylation of the 7-hydroxyl group and removal of the prenyl side chain. As a result of these structural changes, the most active flavanone of the series (I) was 20 times more potent than (±)-abyssinone II (IC50 40.95 μM).

Abstract

Synthesis and Biological Evaluation of (±)-Abyssinone II and Its Analogues as Aromatase Inhibitors for Chemoprevention of Breast Cancer. Maiti, Arup; Cuendet, Muriel; Croy, Vicki L.; Endringer, Denise C.; Pezzuto, John M.; Cushman, Mark. Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and The Purdue Cancer Center, Purdue University, West Lafayette, IN, USA. Journal of Medicinal Chemistry (2007), 50(12), 2799-2806. Publisher: American Chemical Society, CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 147:166076 AN 2007:546064 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Allergy-preventive activity was demonstrated for an ext. of resins from Xanthorrhoea hastilis R. BR. in a search for allergy-preventive substances from natural sources. By bioassay-directed fractionation of this plant ext., a new flavanone, 3',5'-dihydroxy-7,4'-dimethoxyflavanone (1), and two new chalcones, 3,5,2'-trihydroxy-4,4'-dimethoxychalcone (2) and 5,2'-dihydroxy-3,4,4'-trimethoxychalcone (3), were isolated together with five known compds., 5'-hydroxy-7,3',4'-trimethoxyflavanone (4), 3'-hydroxy-7,4'-dimethoxyflavanone (5), liquiritigenin 7-Me ether (6), 4,2'-dihydroxy-4'-methoxychalcone (7) and sakuranetin (8). The structures of 1, 2 and 3 were elucidated by spectroscopic methods. All of these compds. showed allergy-preventive effects.

Abstract

Allergy-preventive flavonoids from Xanthorrhoea hastilis. Ogawa, Yuko; Oku, Hisae; Iwaoka, Emiko; Iinuma, Munekazu; Ishiguro, Kyoko. School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien, Kyuban-cho, Nishinomiya, Japan. Chemical & Pharmaceutical Bulletin (2007), 55(4), 675-678. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 147:113847 AN 2007:562835 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Priority Application

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AP, EA, EP, OA


WO 2007053915 A3 20070802WO 2007053915 A2 20070518 WO 2006-BE121 20061109Patent No. Kind Date Application No. Date Patent Family Information

Preparation of naringenin derivatives with selectivity on estrogen receptors. De Keukeleire, Denis; Roelens, Frederik; Dhooge, Willem. (Universiteit Gent, Belg.). PCT Int. Appl. (2007), 54pp. CODEN: PIXXD2 WO 2007053915 A2 20070518 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-BE121 20061109. Priority: EP 2005-447250 20051109. CAN 146:521587 AN 2007:538912 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


IT-MS operated in the pos. mode was applied for the rapid characterization/quantification of the flavanones in exts. from Fructus aurantii. APCI-MS and CID MS/MS provide unequivocal mol. wt. (MW) data of these compds. and useful information about their structures (diagnostic fragment ions). Main fragment pathways include neutral losses of H2O, C2H2O, and B-ring as well as a retro-Diels-Alder (RDA) fragment giving rise to [1,3A + H]+, [1,3B + H]+, and [1,4B-H2 + H]+ ions, which form the characteristic MS/MS "fingerprint" of flavanone aglycons. When screening exts. of F. aurantii for flavanone aglycons, 8 target compds. were characterized using this fingerprint. Meanwhile, ESI-MS in full-scan mode was developed and validated for the quantification of the main flavanone aglycons in F. aurantii. This method is simple, accurate, fast and requires only 16 min per sample for direct detection and quantification of naringenin and hesperetin. All the results and these characteristic fragments showed that the IT-MS is a powerful tool for the structural characterization and quant. detn. of flavanone aglycons.

Abstract

Rapid qualitative and quantitative analyses of flavanone aglycons in Fructus aurantii by HPLC ion-trap MS. Zhou, Da-yong; Xu, Qing; Xue, Xing-ya; Zhang, Fei-fang; Jing, Yu; Liang, Xin-miao. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Peop. Rep. China. Journal of Separation Science (2007), 30(6), 858-867. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 147:207715 AN 2007:541799 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone




Synthesis of flavanone inhibitors of FtsZ as antibiotics. Shaw, Jared; Urgaonkar, Sameer; Raychaudhuri, Debabrata; La Pierre, Henry. (President and Fellows of Harvard College, USA). PCT Int. Appl. (2007), 129pp. CODEN: PIXXD2 WO 2007056188 A1 20070518 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US43042 20061103. Priority: US 2005-733543 20051104. CAN 146:521598 AN 2007:537785 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

HO

HO

R8

I

Naringenin derivs., such as I [R8 = alkyl, alkenyl, alkynyl], with selective anti-estrogenic activity were prepd. for use in pharmaceutical compns. for treatment of estrogen-dependent diseases or disorders, i.e. estrogen-deficiency dependent disorders and diseases with excessive estrogen prodn. or conditions benefiting from modulated estrogen prodn., such as estrogen-dependent cancers, endometriosis, gynecomastia, impaired hypothalamo-pituitary regulation of gonadal function and bone homeostasis. Thus, flavanone I [R8 = (CH2)6Me] was prepd. via a seven step synthetic sequence starting from hexyllithium or hexylmagnesium bromide, 2,4,6-trimethoxybenzaldehyde, acetyl chloride and 4-(methoxymethoxy)benzaldehyde. The prepd. naringenin derivs. were assayed for α- and β-estrogen receptor agonist/antagonist activity and for effect on bone mineral d. and uterus wt. in ovariectomized rats.

Abstract EP 2005-447250 A 20051109


flavanone

The invention provides a peroxisome proliferator-activated receptor (PPAR) β/δ activator, characterized by contg. a flavone, flavonol, Abstract JP 2005-317153 20051031Priority Application JP 2007119429 A 20070517 JP 2005-317153 20051031 Patent No. Kind Date Application No. Date Patent Family Information

Peroxisome proliferator-activated receptor activators, and skin compositions containing the same. Nanami, Yoshihiko; Ito, Kenichi; Idamarcoda, Alnasili. (Ichimaru Pharcos Inc., Japan). Jpn. Kokai Tokkyo Koho (2007), 34pp. CODEN: JKXXAF JP 2007119429 A 20070517 Patent written in Japanese. Application: JP 2005-317153 20051031. Priority: . CAN 146:467928 AN 2007:531962 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OO

O O

P

P

HO

OH OH

O Ph

O

HO HO

OH

R2

R1

R3

R4

R5

R6I II

Polyphenol compds. of formula I [R1-R4 = H, halo, cycloalkyl, alkyl, acyl, aryl, etc.; R5, R6 = absent, H, halo, alkyl, etc.; P = H, alkyl, protecting group, acyl, aryl, etc.] are prepd. which inhibit the GTPase activity of FtsZ. These compds. are useful in treating infections, particularly infections caused by gram-pos. organisms. Methods of prepg. the inventive compds. are also provided. The compds. are prepd. by the benzylation of pinocembrin or chrysin core structure. Pharmaceutical compns. and method of using the compds. to treat disease are also provided. These compds. may be screened for antimicrobial activity as well as other biol. activities such as anti-neoplastic, anti-inflammatory, immunosuppressive, and cytotoxic activity. Thus, (±)-2'''-hydroxy-5''-benzylisouvarinol-B (II) was prepd., and had IC50 value of 8.3 μM for inhibition of E. coli FtsZ GTPase activity.



flavanone

Large-pore cubic Ia-3d mesoporous silicas were synthesized by co-condensation of tetraethoxysilane (TEOS) and a small amt. of phenyltriethoxysilane (PTES) under acidic conditions using triblock copolymer P123 (EO20PO70EO20) as the template. In the synthesis procedure, the amt. of PTES added in the range of 3.0-10% was very vital for the formation of the ordered Ia-3d structure. In addn., the prehydrolysis of PTES prior to TEOS in the template soln. was also important for the prepn. of ordered Ia-3d materials. If TEOS was prehydrolyzed, ordered 2d-hexagonal materials were obtained. After mild calcination at 250° to selectively remove the

Abstract

Large-pore cubic Ia-3d mesoporous silicas: Synthesis, modification and catalytic applications. Huang, Jiahui; Tian, Ge; Wang, Hongsu; Xu, Ling; Kan, Qiubin. Department of Chemistry, Jilin University, Changchun, Peop. Rep. China. Journal of Molecular Catalysis A: Chemical (2007), 271(1-2), 200-208. Publisher: Elsevier B.V., CODEN: JMCCF2 ISSN: 1381-1169. Journal written in English. CAN 148:403597 AN 2007:526377 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Provided is a method for introducing hydroxyl group into the Ph group (benzene ring) of a flavones compd. and producing hydroxylated flavones. A hydroxylated flavone compd. is a diol body where two hydroxyl groups are introduced into position 2 and 3 of the Ph group of a flavone chem. compd. The method comprises the following steps: (a) transformation of a vector carrying a modified arom. ring dioxygenase gene (modified BphA) and dihydrodiol dehydrogenase gene (BphB) into a microorganism; (b) expression of modified BphA and BphB in the microorganism; (c) prodn. of hydroxylated flavones by adding at least one of the culture products of the microorganism to a sample contg. flavones compd., mixing or cultivating, and obtaining the hydroxylated flavones compd. from the mixt. or culture products. The modified arom. ring dioxygenase has mutations at position 324-325 introduced by mutagenesis. The sequences of two arom. ring dioxygenase mutants are provided.


Modified aromatic ring dioxygenase and uses in production of hydroxylated flavones. Kagami, Osamu; Misawa, Norihiko; Shindo, Kazutoshi. (Marine Biotechnology Institute, Japan). Jpn. Kokai Tokkyo Koho (2007), 27pp. CODEN: JKXXAF JP 2007116975 A 20070517 Patent written in Japanese. Application: JP 2005-313177 20051027. Priority: . CAN 146:517036 AN 2007:528853 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone, flavanol, and/or isoflavone as an active component, wherein the PPAR β/δ-activator is suitable for use in a skin compn. for prevention and treatment of rough skin, skin inflammation, and decrease of skin barrier function. For example, the effect of luteolin on PPAR β/δ activation was in vitro tested. Also, a cosmetic emulsion contg. rhoifolin 0.1 % was formulated.


flavanone

Answer 230:

The present work studied the influence of the plant activators Biokal 01, Milsana VP 2001, potassic silicate and SilKaBen on the phenylpropanoid metab. of apple leaves. Chem. anal. and detn. of enzyme activities were carried out in leaves of the scab susceptible apple cv. 'Golden Delicious' and the scab resistant cv. 'Rewena'. The activity of several enzymes of the flavonoid biosynthesis [phenylalanine ammonia lyase (PAL), chalcone synthase/-isomerase (CHS/CHI), flavanone 3-hydroxylase (FHT) and dihydroflavonol 4-reductase (DFR)] was detd. An increasing activity of these enzymes did not stringently cause higher contents of phenylpropanoids. However, changes in the phenylpropanoid content of the apple leaves were related to changes at the enzyme level. Effects of enzyme stimulation could be obsd. within the first 3 days after application of activating reagents. The phenylpropanoid metab. was induced faster and stronger in young leaves than adult ones. Changes in the phenylpropanoid metab. could be found at all times tested within 4 h to 3 days.

Abstract

Stimulation of the phenylpropanoid biosynthesis by plant activators in apple leaves. Strissel, T.; Hoyer, U.; Zistler, C.; Treutter, D.; Halbwirth, H.; Stich, K. Weihenstephan Chair of Fruit Science, Technical University Munich, Freising, Germany. Acta Horticulturae (2007), 732(Proceedings of the VIIIth International Symposium on Canopy, Rootstocks and Environmental Physiology in Orchard Systems, 2004), 549-554. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 147:498993 AN 2007:493507 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Five flavonoid structural genes, encoding chalcone isomerase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, anthocyanidin synthase, and anthocyanidin reductase, were cloned from a brown-fiber cotton line (T586). The predicted proteins of these genes exhibit high sequence similarity with corresponding enzymes from various plants. RT-PCR anal. showed these genes are developmentally co-regulated and preferentially expressed in developing fibers of T586. Expression analyses and dimethylaminocinnaldehyde staining demonstrated that high transcript levels of these genes in developing fibers and presence of proanthocyanidins in mature fibers co-segregated with brown fiber in a recombination inbred line population. Our results indicated that the cloned flavonoid structural genes and proanthocyanidins were involved in the pigmentation in brown cotton fibers.

Abstract

Cotton flavonoid structural genes related to the pigmentation in brown fibers. Xiao, Yue-Hua; Zhang, Zheng-Sheng; Yin, Meng-Hui; Luo, Ming; Li, Xian-Bi; Hou, Lei; Pei, Yan. Key Laboratory of Biotechnology and Crop Quality Improvement of the Ministry of Agriculture, Peop. Rep. China. Biochemical and Biophysical Research Communications (2007), 358(1), 73-78. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 147:113929 AN 2007:523867 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


template, Ia-3d and 2d-hexagonal materials with 10% PTES were selected to be sulfonated to introduce sulfonic acid sites into the channels. Both Ia-3d and 2d-hexagonal mesoporous sulfonic acid catalysts can effectively catalyze the liq. phase condensation reaction of phenol with acetone to Bisphenol A. The catalytic activity of the Ia-3d catalyst was slightly higher than that of the 2d-hexagonal one. Addnl., after calcination at 550 °C to remove the template and Ph groups, Ia-3d mesoporous materials with different pore sizes (3.8-6.8 nm) were further functionalized with amino groups by postsynthesis grafting. It was found that in the synthesis of flavanone the catalytic performance of amino-functionalized Ia-3d mesoporous base catalysts increased with the increase in their pore sizes.


flavanone


New synthetic polymeric chiral selectors were developed recently as chiral stationary phases. They were tested with supercrit. fluid mobile phases made of CO2 plus an alc. modifier and 0.2% vol./vol. trifluoroacetic acid. The polymeric N,N'-(1S,2S)-1,2-cyclohexanediyl-bis-2-propenamide (P-CAP), the polymeric N,N'-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-2-propenamide (P-CAP-DP), the polymeric trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide (DEABV) and the polymeric N,N'-[(1R,2R)-1,2-diphenyl-1,2-ethanediyl] bis-4-vinylbenzamide (DPEVB) were bonded to 5 μm silica particles and used to prep. four columns that were tested with a set of 88 chiral compds. with a wide variety of chem. functionalities. All 88 test compds. were sepd. on one or more of these related polymeric CSPs. Forty-three enantiomeric pairs were sepd. in SFC conditions by only one of the CSPs. Twenty pairs were sepd. by two CSPs and 18 and 7 enantiomeric pairs were sepd. by 3 and all 4 CSPs, resp. The three P-CAP, P-CAP-DP and DEABV CSPs have equiv. success being able to sep. 49 enantiomeric pairs of the studied set with resp. 12, 14 and 20 at baseline (Rs > 1.5). The DPEVB CSP was significantly less efficient sepg. only 18 chiral compds. with only one at baseline. The great advantage of the SFC mobile phases is the rapid sepn., witch most achieved in <5 min.

Abstract

Super/subcritical fluid chromatography separations with four synthetic polymeric chiral stationary phases. Han, X.; Berthod, A.; Wang, C.; Huang, K.; Armstrong, D. W. Department of Chemistry, University of Texas at Arlington, Arlington, TX, USA. Chromatographia (2007), 65(7/8), 381-400. Publisher: Vieweg Verlag/GWV Fachverlage GmbH, CODEN: CHRGB7 ISSN: 0009-5893. Journal written in English. CAN 148:44786 AN 2007:490725 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Natural products, including flavonoids, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, studies concerning the effect of flavonoids frequently lacked data regarding to flavanones. In this study, we investigated the inhibitory effect of flavanone compds., including flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone, naringin and naringenin, on cell growth of various cancer cells. We detd. that flavanone and 2'-OH flavanone inhibited cell growth of A549, LLC, AGS, SK-Hep1 and HA22T cancer cells, while other flavanones showed little or no inhibition. We evaluated growth-inhibitory activity of flavanone and 2'-OH flavanone against highly proliferative human lung cancer cells (A549) via anchorage-independent and -dependent colony formation assay, and further showed that treatment of flavanone resulted in a G1 cell cycle arrest with redn. of cyclin D, E and cyclin-dependent kinase (CDK) 2, while treatment of 2'-OH flavanone led to a G2/M phase accumulation with redn. of cyclin B, D and Cdc2. Moreover, we demonstrated the improvement effect of flavanone and 2'-OH flavanone with anti-cancer drug, doxorubicin, on A549 cells. Finally, flavanone and 2'-OH flavanone were evidenced by its inhibition on the growth of A549 and Lewis lung carcinoma cells in vivo.

Abstract

The tumor-growth inhibitory activity of flavanone and 2'-OH flavanone in vitro and in vivo through induction of cell cycle arrest and suppression of cyclins and CDKs. Hsiao, Yung-Chin; Hsieh, Yih-Shou; Kuo, Wu-Hsien; Chiou, Hui-Ling; Yang, Shun-Fa; Chiang, Whei-Ling; Chu, Shu-Chen. Institute of Biochemistry and Biotechnology, Chung Shan Medical University, Taichung, Taiwan. Journal of Biomedical Science (Dordrecht, Netherlands) (2007), 14(1), 107-119. Publisher: Springer, CODEN: JBCIEA ISSN: 1021-7770. Journal written in English. CAN 148:69416 AN 2007:491606 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Secondary metabolites from Andrographis paniculata. Li, Wenkui; Xu, Xudong; Zhang, Hongjie; Ma, Cuiying; Fong, Harry; van Breemen, Richard; Fitzloff, John. Department of Medicinal Chemistry and Pharmacognosy (m/c 781), University of Illinois at Chicago, Chicago, IL, USA. Chemical & Pharmaceutical Bulletin (2007), 55(3), 455-458. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 147:113817 AN 2007:483221 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new flavanone glucosides, (2S)-5,7,3',5'-tetrahydroxy-flavanone 7-O-β-D-allopyranoside (1) and (2S)-5,7,3',5'-tetrahydroxy-flavanone 7-O-β-D-glucopyranosine (2) were isolated from the stems and leaves of Jasminum lanceolarium, along with five known compds.: Betulinaldehyde (3), betulinic acid (4), betulin (5), syringin (6) and Liriodendrin (7). Their structures were detd. on the basis of spectroscopic and chem. methods. The isolated compds. were screened for their in vitro antioxidant activity through DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging assay. Compds. 2 demonstrated significant radical scavenging activity.

Abstract

Two new flavanone glycosides of Jasminum lanceolarium and their anti-oxidant activities. Sun, Jia-Ming; Yang, Jun-Shan; Zhang, Hui. Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peop. Rep. China. Chemical & Pharmaceutical Bulletin (2007), 55(3), 474-476. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 147:113819 AN 2007:483227 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Mandarin juices from three pure clementine (Citrus clementina Hort. ex Tan.) cultivars: Clemenules, Hernandine and Marisol, two clementine-hybrid cultivars: Nova (clementine × tangelo Orlando) and Fortune (clementine × mandarin Dancy), one mandarin-hybrid cultivar: Ortanique (mandarin × orange) and one satsuma (Citrus unshiu Marc) cultivar: Clauselline have been analyzed for detn. of total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities. Total antiradical activity followed the order: pure clementine and Nova > Ortanique > Fortune and Clauselline. Cumulative fast-kinetics antiradical activity was the major contributor to total antiradical activity, accounting for about 87% as av. Ascorbic acid content was the major contributor to cumulative fast-kinetics antiradical activity, accounting for about 93.5% as av. A weak correlation (r2 = 0.151) between total flavanone-7-O-glycosides (FGs, Narirutin, Hesperidin and Didymin) content and cumulative slow-kinetics antiradical activity was obsd. However, ascorbic acid and total FGs contents showed a significant neg. correlation (r2 = 0.658). By using the cumulative fast-kinetics and slow-kinetics antiradical activities as variables, all the assayed juices were significantly discriminated (<0.05) by statistical multivariate discriminant anal.

Abstract

Total, cumulative fast-kinetics and cumulative slow-kinetics antiradical activities of juices from clementine (Citrus clementina), clementine-hybrids and satsuma (Citrus unshiu) cultivars and their utility as discriminant variables. Sentandreu, Enrique; Izquierdo, Luis; Sendra, Jose M. Instituto de Agroquimica y Tecnologia de Alimentos, Valencia, Spain. European Food Research and Technology (2007), 225(2), 271-278. Publisher: Springer GmbH, CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 147:165116 AN 2007:487399 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 237:

A new prenylated dihydroflavonoid was obtained from the root of Dolichos tenuicaulis (Baker) Craib. The structure was elucidated as (2S)-5,2',6'-trihydroxy-3''',8-di(γ,γ-dimethylallyl)-2''',2'''-dimethylpyrano[5''',6''':6,7]-2''''',4'''''-cyclohexadiene-1'''''-one[2''''',3''''':3',4']flavanone, named dolichnin A, by spectroscopic methods including UV, IR, HR-EI-MS, 1D NMR and 2D NMR techniques, and subsequently, the anticancer activity of this compd. to inhibit human cancer cells' growth including A549, BEL-7402, Hep-3B, SMMC7721, HT-29, MCF-7, SGC-7902, K562, A498 and PC3 cell lines by MTT method was evaluated in vitro.

Abstract

A new bioactive prenylated dihydroflavanoid from Dolichos tenuicaulis (Baker) Craib. Peng, Jin Yong; Liu, Hai Yan; Qi, Yan; Han, Xu; Xu, You Wei; Xu, Li Na; Xu, Qi Wei. School of Pharmacy, Dalian Medical University, Dalian, Peop. Rep. China. Chinese Chemical Letters (2007), 18(3), 293-296. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 147:482996 AN 2007:475259 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The antioxidative activity of flavonoids depends upon a combination of many factors, such as the concn. and chem. structure of the flavonoids and the arrangement of functional groups in their structure. In the present study, to evaluate the antioxidative effect of several types of flavonoids on catalase activity at a physiol. H2O2 concn., a chemiluminescent (CL) method was used. The H2O2/luminol-dependent CL intensity in a system contg. 3.7 nM catalase and low concns. (10-100 nM) of green tea flavanols (epigallocatechin gallate; EGCG and epicatechin gallate; EG) was enhanced in comparison with that of a system without catalase, suggesting that EGCG and EG partially suppressed catalase activity. On the other hand, flavone and flavonols such as rutin (a 3-glycosidic flavone), quercitrin (a 3-glycosidic flavonol), myricetin, and kaempferol (flavonols), resp., lowered the CL intensity to a greater extent at low concns. (<0.1 μM) when catalase was present than when catalase was absent, indicating that these flavonoids activate catalase. In addn., isoflavone and flavanone such as daidzein and naringenin, resp., exhibited weak antioxidative activities against H2O2 without any effect on the catalase activity over a wide range of flavonoid concns. (0.04-0.4 μM). From these results, it was for the first time suggested that the binding of flavonoids to the heme moiety or a protein region of catalase contributes to the enhancement of catalase activity.

Abstract

Chemical structure-dependent differential effects of flavonoids on the catalase activity as evaluated by a chemiluminescent method. Doronicheva, Nataliya; Yasui, Hiroyuki; Sakurai, Hiromu. Department of Analytical and Bioinorganic Chemistry, Kyoto Pharmaceutical University, 5 Nakauchi-cho, Misasagi, Yamashina-ku, Kyoto, Japan. Biological & Pharmaceutical Bulletin (2007), 30(2), 213-217. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 146:474775 AN 2007:480490 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new flavonoid glycosides, 5-hydroxy-7,8-dimethoxy (2R)-flavanone-5-O-β-D-glucopyranoside (1) and 5-hydroxy-7,8,2',5'-tetramethoxy-flavone-5-O-β-D-glucopyranoside (2), and a new diterpenoid, androg. acid (3), along with andrographidin A (4) were isolated from Andrographis paniculata, and their structures were detd. on the basis of physicochem. and spectroscopic anal. Compd. 3 was evaluated for cytotoxicity to KB cells along with andrographolide, isoandrographolide, neoandrographolide and 14-deoxy-11,12-didehydroandrographolide obtained from A. paniculata in the present study. Cytotoxicity was obsd. for andrographolide and isoandrographolide with ED50 values of 6.5 and 5.1 μg/mL, resp.


flavanone

The completion of the whole genome sequence of Arabidopsis thaliana has made it possible to explore the phytochem. genomics in this species by detg. gene-to-metabolite correlation through the comprehensive anal. of metabolite accumulation and gene expression. In this study, flavonoid profiling of wild-type plants and T-DNA insertion mutants was analyzed using ultra-performance liq. chromatog. (UPLC)/photodiode array detection (PDA)/electrospray ionization (ESI)/multiple-stage mass spectrometry (MSn). Detailed anal. of the metabolite changes in the mutants suggested the functions of genes that have been mutated. In silico coexpression anal. of genes involved in flavonoid metab. in Arabidopsis was performed using a publicly available transcriptome database of DNA microarrays. We

Abstract

Phytochemical genomics in Arabidopsis thaliana: a case study for functional identification of flavonoid biosynthesis genes. Tohge, Takayuki; Yonekura-Sakakibara, Keiko; Niida, Rie; Watanabe-Takahashi, Akiko; Saito, Kazuki. RIKEN Plant Science Center, 1-7-22, Suehiro-cho, Tsurumi-ku, Yokohama-shi, Kanagawa, Japan. Pure and Applied Chemistry (2007), 79(4), 811-823. Publisher: International Union of Pure and Applied Chemistry, CODEN: PACHAS ISSN: 0033-4545. Journal written in English. CAN 147:65479 AN 2007:467185 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A flavanone and other constituents of the Brazilian endemic species Trembleya laniflora (D. Don) Cogn. (Melastomataceae) [Biochemical Systematics and Ecology 35(2007) 40-41]. Ventura, Claiton Pires; Dias de Souza Filho, Jose; Braga de Oliveira, Alaide; Braga, Fernao Castro. Faculdade de Farmacia, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil. Biochemical Systematics and Ecology (2007), 35(7), 472. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal; Miscellaneous written in English. AN 2007:472048 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Pigmented orange pulp wash, a liq. byproduct of citrus processing, was used to obtain alc. ext. of anthocyanins and hydroxycinnamates, flavanones, and purified sugar conc. by a series of resin adsorptions and membrane techniques. The final products and the intermediates were characterized by chem. and microbiol. methods. The anthocyanins, limonoids, flavanones, and hydroxycinnamates were fully removed by a neutral polystyrene-divinylbenzene resin and could be selectively recovered by using appropriate solvents as eluents; they could be used as ingredients in dietary supplements and/or as raw materials in cosmetic, pharmaceutical, and nutraceutical prepns. The acidity of the decolored eluate was diminished by weakly basic ion-exchange matrix, while the ultrafiltration process stabilized the product by removal of enzymes and microorganisms. Reverse osmosis treatment removed 80% of water and increased the sugar concn. 4-times. The final product with 28°Brix sol. solids contained .apprx.250 g sugars (glucose, fructose, sucrose), .apprx.9 g citric acid, and 1 g pectins per L. The conc. was a transparent liq. of slight amber color with very low microbial count. It may be used as a natural sweetener in foods and beverages.

Abstract

Recovery of anthocyanins, flavanones and sugars from by-products of pigmented orange processing. Scordina, Monica; Di Mauro, Alfio; Passerini, Amedeo; Maccarone, Emanuele. Dipartimento di OrtoFloroArboricoltura e Tecnologie Agroalimentari (DOFATA), Tecnologie Agroalimentari, Universita degli Studi di Catania, Catania, Italy. Ingredienti Alimentari (2007), 6(1), 23-31. Publisher: Chiriotti Editori sas, CODEN: IANLBJ ISSN: 1594-0543. Journal written in Italian. CAN 147:141802 AN 2007:474864 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The effect of naringin, a grapefruit flavanone was studied on bleomycin-induced genomic damage and alteration in the survival of cultured V79 cells. Exposure of V79 cells to bleomycin induced a concn. dependent elevation in the frequency of binucleate cells bearing micronuclei (MNBNC) and a max. no. of MNBNCs were obsd. in the cells treated with 50 μg ml-1 bleomycin, the highest concn. evaluated. This genotoxic effect of bleomycin was reflected in the cell survival, where a concn. dependent decline was obsd. in the cells treated with different concns. of bleomycin. Treatment of cells with 1 mM naringin before exposure to different concns. of

Abstract

Naringin, a grapefruit flavanone, protects V79 cells against the bleomycin-induced genotoxicity and decline in survival. Jagetia, Abhinav; Jagetia, Ganesh Chandra; Jha, Shalini. Department of Metallurgy, Malviya National Institute of Technology, Jaipur, India. Journal of Applied Toxicology (2007), 27(2), 122-132. Publisher: John Wiley & Sons Ltd., CODEN: JJATDK ISSN: 0260-437X. Journal written in English. CAN 147:45497 AN 2007:459452 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chemopreventive activity of 1, 2.5, 5, 10, 25, 50, 100 or 250 mg/kg b. wt. naringin, a citrus flavanone was studied on the benzo(a)pyrene (BaP)-induced forestomach carcinoma in female Swiss albino mice. Naringin was given before, after or both (before & after) orally or i.p. to mice receiving BaP for the induction of chem. carcinogenesis. The optimum chemopreventive dose was found to be 10 mg/kg p.o. and oral administration was more effective than the i.p. treatment. A max. chemopreventive activity of naringin was obsd. when it was given during and after the termination of BaP treatment. The tumor incidence and tumor multiplicity were reduced in a dose dependent manner, and highest redn. of 78% in tumor multiplicity was obsd. at 10 mg/kg, where a 20% redn. in tumor incidence was also obsd. However, a reduced chemopreventive effect was obsd. when naringin was given either before or after chem. induced carcinogenesis. These observations were further confirmed by PCNA labeling where naringin pretreatment reduced the PCNA labeling index by four folds. The micronuclei anal. in splenocytes also confirms to the chemopreventive activity of naringin. BaP treatment increased the frequency of micronuclei bearing splenocytes (MNBNC) by six folds. Naringin treatment during and after BaP administration reduced the frequency of MNBNC in a dose dependent manner up to 10 mg/kg where a highest redn. in MNBNC was obsd., thereafter the frequency of MNBNC showed a marginal increase up to a dose of 250 mg/kg naringin however it was two folds lower than BaP treatment alone. A similar effect on MNBNC decline was obsd. for pre or post-naringin treated group however, the degree of decline in MNBNC was lesser when compared to pre-post naringin treatment. Our study demonstrates, that the naringin possesses chemopreventive activity and this may be due to redn. in DNA damage as evidenced by lower frequency of MNBNC in the group treated with naringin during and after chem. carcinogenesis.

Abstract

Chemopreventive effect of naringin on the benzo(a)pyrene-induced forestomach carcinoma in mice. Jagetia, Ganesh Chandra; Reddy, Tiyyagura Koti. Department of Radiobiology, Kasturba Medical College, Manipal, India. International Journal of Cancer Prevention (2004), 1(6), 429-444. Publisher: Nova Science Publishers, Inc., CODEN: IJCPC6 ISSN: 1554-1134. Journal written in English. CAN 146:454476 AN 2007:465380 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


inferred a coexpression framework model of the genes involved in the pathways of flavonol, anthocyanin, and proanthocyanidin synthesis, suggesting specific functions and coregulation of the genes of pathway enzymes and transcription factors. The metabolic profiling of the omt1 mutant lacking a methyltransferase gene narrowed down by the coexpression anal. showed that AtOMT1 (At5g54160) is involved not only in the prodn. of lignins and sinapoyl esters but also in the methylation of flavonols forming isorhamnetin. These results suggest that the functional genomics approach by detailed target-metabolite profiling with transcriptome coexpression anal. provides an efficient way of identifying novel gene functions involved in plant metab.


flavanone

In vivo metabolic effects of naringenin in the ethanol consuming rat and the effect of naringenin on adipocytes in vitro. Szkudelska, K.; Nogowski, L.; Nowicka, E.; Szkudelski, T. Department of Aninal Physiology and Biochemistry, University of Agriculture, Poznan, Pol. Journal of Animal Physiology and Animal Nutrition (2007), 91(3-4), 91-99. Publisher: Blackwell Verlag GmbH, CODEN: JAPNEF ISSN: 0931-2439. Journal written in English. CAN 147:159813 AN 2007:451913 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


effects.

Flavonoids are phytochems. exhibiting a wide range of biol. activities, among which are antioxidant activity, the ability to modulate activity of several enzymes or cell receptors and possibility to interfere with essential biochem. pathways. Using human laryngeal carcinoma HEp2 cells and their drug-resistant CK2 subline, we examd. the effect of five flavonoids, three structurally related flavons (quercetin, fisetin, and myricetin), one flavonol (luteolin) and one glycosylated flavanone (naringin) for: (i) their ability to inhibit mitochondrial dehydrogenases as an indicator of cytotoxic effect, (ii) their influence on glutathione level, (iii) antioxidant/prooxidant effects and influence on cell membrane permeability, and (iv) effect on expression of cytochrome CYP1A1. Cytotoxic action of the investigated flavonoids after 72 h of treatment follows this order: luteolin>quercetin>fisetin>naringin>myricetin. Our results show that CK2 were more resistant to toxic concns. of flavonoids as compared to parental cells. Quercetin increased the total GSH level in both cell lines. CK2 cells are less perceptible to lipid peroxidn. and damage caused by free radicals. Quercetin showed prooxidant effect in both cell lines, luteolin only in HEp2 cells, whereas other tested flavonoids did not cause lipid peroxidn. in the tested cell lines. These data suggest that the same compd., quercetin, can act as a prooxidant, but also, it may prevent damage in cells caused by free radicals, due to the induction of GSH, by forming less harmful complex. Quercetin treatment damaged cell membranes in both cell lines. Fisetin caused higher cell membrane permeability only in HEp2 cells. However, these two compds. did not enhance the damage caused by hydrogen peroxide. Quercetin, naringin, myricetin and fisetin increased the expression of CYP1A1 in both cell lines, while luteolin decreased basal level of CYP1A1 only in HEp2 cells. In conclusion, small differences in chem. structure of flavonoids led to drastic change of their biol.

Abstract

Effect of flavonoids on glutathione level, lipid peroxidation and cytochrome P450 CYP1A1 expression in human laryngeal carcinoma cell lines. Durgo, Ksenija; Vukovic, Lidija; Rusak, Gordana; Osmak, Maja; Colic, Jasna Franekic. Faculty of Food Technology and Biotechnology, University of Zagreb, Zagreb, Croatia. Food Technology and Biotechnology (2007), 45(1), 69-79. Publisher: University of Zagreb, Faculty of Food Technology and Biotechnology, CODEN: FTBRFD ISSN: 1330-9862. Journal written in English. CAN 147:63615 AN 2007:456105 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


bleomycin arrested the bleomycin-induced decline in the cell survival accompanied by a significant redn. in the frequency of micronuclei when compared with bleomycin treatment alone. The cell survival and micronuclei induction were inversely correlated. The repair kinetics of DNA damage induced by bleomycin was evaluated by exposing the cells to 10 μg ml-1 bleomycin using single cell gel electrophoresis. Treatment of V79 cells with bleomycin resulted in a continuous increase in DNA damage up to 6 h post-bleomycin treatment as evident by migration of more DNA into the tails (% tail DNA) of the comets and a subsequent increase in olive tail moment (OTM), an index of DNA damage. Treatment of V79 cells with 1 mM naringin reduced bleomycin-induced DNA damage and accelerated DNA repair as indicated by a redn. in % tail DNA and OTM with increasing assessment time. A max. redn. in the DNA damage was obsd. at 6 h post-bleomycin treatment, where it was 5 times lower than bleomycin alone. Our study, which was conducted on the basis of antioxidant, free radical scavenging and metal chelating properties of naringin demonstrates that naringin reduced the genotoxic effects of bleomycin and consequently increased the cell survival and therefore may act as a chemoprotective agent in clin. situations.


flavanone

Abstract

New reports on surface flavonoids from Chamaebatiaria (Rosaceae), Dodonaea (Sapindaceae), Elsholtzia (Lamiaceae), and Silphium (Asteraceae). Wollenweber, Eckhard; Roitman, James N. Institut fuer Botanik der TU Darmstadt, Darmstadt, Germany. Natural Product Communications (2007), 2(4), 385-389. Publisher: Natural Product Inc., CODEN: NPCACO ISSN: 1934-578X. Journal written in English. CAN 148:27665 AN 2007:447013 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The bioassay-guided purifn. of an n-hexane ext. from the leaves of Piper hostmannianum var. berbicense led to the isolation of four monoterpene or prenyl-substituted dihydrochalcones (1a, 1b, 2, 3) as well as the known compds. 2',6'-dihydroxy-4'-methoxydihydrochalcone (4), linderatone (5), strobopinin (6), adunctin E (7) and (-)-methyllinderatin (8). Their structures were established on the basis of NMR and X-ray anal. (-)-Methyllinderatin, linderatone and 2',6'-dihydroxy-4'-methoxydihydrochalcone exhibited the most potent antiplasmodial activity with IC50 values of 5.64, 10.33 and 12.69 μM, resp. against both chloroquine-sensitive and resistant strains of Plasmodium falciparum (F32, FcB1). The activity of (-)-methyllinderatin was confirmed in vivo against Plasmodium vinckei petteri in mice (80% of redn. of parasitemia) at a dose of 20 mg/kg/day.

Abstract

Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense. Portet, Benedicte; Fabre, Nicolas; Roumy, Vincent; Gornitzka, Heinz; Bourdy, Genevieve; Chevalley, Severine; Sauvain, Michel; Valentin, Alexis; Moulis, Claude. Faculte des Sciences Pharmaceutiques, UMR 152, IRD - Universite Paul Sabatier Toulouse 3, Toulouse, Fr. Phytochemistry (Elsevier) (2007), 68(9), 1312-1320. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 147:161945 AN 2007:447888 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


of normal and ethanol-consuming rats and on metab. of isolated rat adipocytes.

Naringenin is a bioactive flavanone involved in the inhibition of drug metab. which exhibits antioxidant, anti-inflammatory and anticancerogenic properties and which recently appeared to be a factor mitigating the hyperlipidemic effects in rats and rabbits. In the performed expt., the effect of naringenin, administered intragastrically (50 mg/kg) for 2 wk to normal and ethanol drinking rats, on insulin and leptin levels and on some metabolic parameters was investigated. Naringenin did not change the hormone levels in any group of rats. Blood glucose, triglyceride, total, esterified and free cholesterol and high-d. lipoprotein-cholesterol concns. were also unaffected by this compd. Only free fatty acids were elevated after the naringenin treatment in the water-drinking rats. In spite of unchanged glucose and insulin concns. in blood, the tested flavanone reduced the glucose/insulin ratio in ethanol-receiving rats. Liver triglycerides, elevated due to ethanol ingestion, were partially normalized by naringenin. Other tested parameters like liver glycogen and cholesterol, muscle triglycerides and glycogen were not altered in any group of rats. The influence of naringenin (62.5, 125, 250 and 500 μM) on basal and insulin-stimulated glucose conversion to lipids (lipogenesis) as well as on basal and epinephrine-stimulated glycerol release (lipolysis) in the isolated rat adipocytes was also tested. The basal and the stimulated lipogenesis tended to be decreased in the presence of the flavanone (250 μM). This inhibitory effect intensified and was statistically significant at the highest concn. of naringenin. The tested compd. did not evoke any effect on basal lipolysis while the epinephrine-stimulated process was limited at the highest concn. of the flavanone. Naringenin (62.5, 125, 250 and 500 μM) had no effect on leptin secretion from the isolated rat adipocytes. Results obtained in our studies demonstrate that naringenin exerts a very weak influence on carbohydrate and lipid metab.

Abstract


flavanone

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AP, EA,

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW


Genes for enzymes of phenylpropanoid and flavonoid biosynthesis of Coffea and their uses in plant improvement. Lepelley, Maud; Cheminade, Gerald; McCarthy, James Gerard; Petiard, Vincent; Lin, Chenwei; Tanksley, Steven D. (Cornell Research Foundation, USA; Nestec S.A.). PCT Int. Appl. (2007), 159pp. CODEN: PIXXD2 WO 2007044992 A2 20070419 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US40686 20061013. Priority: US 2005-726298 20051013. CAN 146:436266 AN 2007:438164 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids are plant secondary metabolites often used as nutraceutical supplements, but a growing no. of unnatural flavonoids are being investigated as therapeutic agents. Cultures of Saccharomyces cerevisiae expressing recombinant flavonoid enzymes, including 4-coumaroyl:CoA ligase (4CL), chalcone synthase (CHS), chalcone isomerase (CHI), and flavanone 3β-hydroxylase (FHT), produced novel flavanones and dihydroflavonols when fed with a no. of arom. acrylic acids. The flavonoid network also exhibited broad substrate specificity by converting muconic acid into a unique polypropanoid.

Abstract

Combinatorial mutasynthesis of flavonoid analogues from acrylic acids in microorganisms. Chemler, Joseph A.; Yan, Yajun; Leonard, Effendi; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, State University of New York at Buffalo, Buffalo, NY, USA. Organic Letters (2007), 9(10), 1855-1858. Publisher: American Chemical Society, CODEN: ORLEF7 ISSN: 1523-7060. Journal written in English. CAN 147:71077 AN 2007:440630 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Lipophilic exudates of one species each of Chamaebatiaria and Elsholtzia, two species of Silphium and four Dodonaea species were analyzed for flavonoid aglycons. In addn. to a no. of well-known and widely distributed flavonoids, several very rare and one novel natural flavonol were isolated and identified. 1H and 13C NMR data of four flavanones and two flavones are reported.


flavanone

Microporous cryst. mol. sieves having a mesoporous skeleton are prepd. by (a) adding a meso-SDA (structure directing agent) to a gel Abstract KR 2005-97161 A 20051014Priority Application KR 2007041239 A 20070418 KR 2005-97161 20051014


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW

WO 2007043731 A1 20070419 WO 2006-KR720 20060302Patent No. Kind Date Application No. Date Patent Family Information

Preparation of microporous crystalline molecular sieve possessing mesoporous frameworks. Ryoo, Ryong; Choi, Minkee. (KAIST, S. Korea). PCT Int. Appl. (2007), 37pp. CODEN: PIXXD2 WO 2007043731 A1 20070419 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-KR720 20060302. Priority: KR 9716-1 20051014. CAN 146:382785 AN 2007:433844 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Genes for the enzymes of biosynthesis of phenylpropanoids and flavonoids in the coffee plant are cloned and characterized for use in crop improvement. They may be used to alter plant metabolite profiles for the manipulation of flavor, aroma, and other features of coffee beans, as well as the manipulation resistance to pathogen, herbivore, and insect attack in the coffee plant. Candidate genes were identified by sequence comparison.


EP, OA


flavanone

Na+-Glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens. Sato, Seizo; Takeo, Jiro; Aoyama, Chihiro; Kawahara, Hiroyuki. Central Research Laboratory, Nippon Suisan Kaisha, Ltd, Hachioji, Tokyo, Japan. Bioorganic & Medicinal Chemistry (2007), 15(10), 3445-3449. Publisher: Elsevier Ltd., CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 147:45176 AN 2007:397599 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Three new (1-3) and four known prenylated flavanones as well as friedelin were isolated from the aerial parts of Esenbeckia berlandieri ssp acapulcensis (Rutaceae). The structures of the new compds. were elucidated as 5,7-dihydroxy-8-(2,3-epoxy-3-methyl-butyl)flavanone (1), 5,4'-dihydroxy-7-methoxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (2), and 5,7,4'-trihydroxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (3). The isolated flavanones possess diferentially functionalized isoprene units at C-8, and this is the first report of flavanones isolated from Esenbeckia species.

Abstract

New prenylated flavanones from Esenbeckia berlandieri ssp. acapulcensis. Cano, Arturo; Espinoza, Marina; Ramos, Clara H.; Delgado, Guillermo. Facultad de Estudios Superiores Zaragoza, Universidad Nacional Autonoma de Mexico, Iztapalapa, Mex. Journal of the Mexican Chemical Society (2006), 50(2), 71-75. Publisher: Sociedad Quimica de Mexico, CODEN: JMCSCD ISSN: 1870-249X. Journal written in English. CAN 147:482985 AN 2007:421379 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Five novel 7-hydroxyflavonols, 7-hydroxyflavanones and their derivs. were synthesized by aldol condensation, cyclization, Algar-Flynn-Oyamada reaction, deprotection and O-prenylation. The overall yields were 22-36%. Target compds. thus prepd. included resokaempferide [i.e., 3,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one], 2-(3,5-dimethoxyphenyl)-3,7-dihydroxy-4H-1-benzopyran-4-one, etc. Their structures were confirmed by 1H NMR, 13C NMR, IR and MS.

Abstract

Synthesis of 7-hydroxyflavonols, 7-hydroxyflavanones and their derivatives. Wang, Qiu-an; Zhou, Qiang; Fan, Hua-fang. College of Chemistry and Chemical Engineering, Hunan University, Changsha, Peop. Rep. China. Hecheng Huaxue (2007), 15(1), 50-54. Publisher: Hecheng Huaxue Bianjibu, CODEN: HEHUE2 ISSN: 1005-1511. Journal written in Chinese. CAN 148:331450 AN 2007:421529 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


compn. of a mol. sieve, (b) subjecting the mixt. obtained in the above step (a) to crystn. by a hydrothermal reaction, a microwave reaction, a dry-gel synthesis, etc., and (c) removing selectively org. materials from the resulted material obtained in the above step (b) by a calcination or a chem. treatment. The SDA can be an organosilane, an organophosphonic acid, or a silica precursor functionalized with the organosilane or organophosphonic acid. The obtained zeolites can be post-treated by alk. soln. treatment, ion exchange, dealumination, metal incorporation, or org. functionalization. The prepd. mol. sieves have a good mol. diffusion ability and a greatly improved catalytic activity.


flavanone

Flavanones richly exist in citrus and have been well characterized to have various bioactive properties. However, the anti-metastasis properties of flavanones remain unclear. The anti-metastatic effects of six flavanones including flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone, naringin, and naringenin were investigated in lung cancer cells. Despite little influence on cell viability, flavanone and 2'-OH flavanone markedly inhibited the invasion, motility, and cell-matrix adhesion of A549 cells. This was assocd. with a reduced expression of matrix metalloproteinase (MMP)-2 and urokinase-type plasminogen activator (u-PA) in treated cells. Treatment with flavanone and 2'-OH flavanone also potently attenuated the phosphorylations of extracellular signal-regulated kinase 1/2 (ERK 1/2) and p38MAPK, as well as the activations of NF-κB and AP-1. The reduced expressions of MMP-2 and u-PA, as well as inhibition of cell invasion were obtained in the cultures treated with U0126 (ERK 1/2 inhibitor) and SB203580 (p38MAPK inhibitor). Thus, the inhibitory effects of flavanone and 2'-OH flavanone on the expression of MMP-2 and u-PA may be at least partly through inactivation

Abstract

Flavanone and 2'-OH flavanone inhibit metastasis of lung cancer cells via down-regulation of proteinases activities and MAPK pathway. Hsiao, Yung-Chin; Kuo, Wu-Hsien; Chen, Pei-Ni; Chang, Horng-Rong; Lin, Tseng-Hsi; Yang, Wei-En; Hsieh, Yih-Shou; Chu, Shu-Chen. Institute of Biochemistry and Biotechnology, Chung Shan Medical University, Taichung, Taiwan. Chemico-Biological Interactions (2007), 167(3), 193-206. Publisher: Elsevier Ireland Ltd., CODEN: CBINA8 ISSN: 0009-2797. Journal written in English. CAN 147:63283 AN 2007:393240 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-pos.), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compds. resulted very active against at least two of the studied tumoral cells. Alk. single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compds. on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship anal. of these compds. was performed and for 4- and 3,4-disubstituted derivs. a quant. correlation was obtained in the case of anti-HT-29 activity.

Abstract

Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships. Cabrera, Mauricio; Simoens, Macarena; Falchi, Gabriela; Lavaggi, M. Laura; Piro, Oscar E.; Castellano, Eduardo E.; Vidal, Anabel; Azqueta, Amaia; Monge, Antonio; Lopez de Cerain, Adela; Sagrera, Gabriel; Seoane, Gustavo; Cerecetto, Hugo; Gonzalez, Mercedes. Departamento de Quimica Organica, Facultad de Quimica-Facultad de Ciencias, Universidad de la Republica, Montevideo, Urug. Bioorganic & Medicinal Chemistry (2007), 15(10), 3356-3367. Publisher: Elsevier Ltd., CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 146:492608 AN 2007:397590 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The methanol ext. of Sophora flavescens, which is used in traditional Chinese medicine (sophorae radix), showed potent Na+-glucose cotransporter (SGLT) inhibitory activity. Our search for active components identified many well-known flavonoid antioxidants: kurarinone, sophoraflavanone G, kushenol K, and kushenol N.

Abstract


flavanone

Differential effect of dietary antioxidant classes (carotenoids, polyphenols, vitamins C and E) on lutein absorption. Reboul, Emmanuelle; Thap, Sinay; Tourniaire, Franck; Andre, Marc; Juhel, Christine; Morange, Sophie; Amiot, Marie-Josephe; Lairon, Denis; Borel, Patrick. INSERM, U476, Marseille, Fr. British Journal of Nutrition (2007), 97(3), 440-446. Publisher: Cambridge University Press, CODEN: BJNUAV ISSN: 0007-1145. Journal written in English. CAN 146:461179 AN 2007:380179 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review discusses the mechanisms and efficacy of iron for collagen regeneration. It also discusses the effect of t-flavanone on hair growth and the use of sunscreens to enhance UV-induced ROS in the skin. Improvement of periodontal tissue damage and antiperspirants and deodorants are tackled.

Abstract

Iron for collagen regeneration and other topics. Fox, Charles. USA. Cosmetics & Toiletries (2007), 122(3), 44,46-48,50. Publisher: Allured Publishing Corp., CODEN: CTOIDG ISSN: 0361-4387. Journal; General Review written in English. CAN 147:57827 AN 2007:388067 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Naringin is the major flavanone-7-O-glycoside of sour orange, and it is mainly responsible for the bitter taste of the fruit. The relative content of (2S)- and (2R)-naringin in the albedo of sour oranges during maturation in the entire season was detd. by normal phase HPLC using Chiralcel OD-H as chiral stationary phase and n-hexane/ethanol doped with 0.5% of TFA as mobile phase. HPLC traces were complicated by the presence of (2S)-neohesperidin, and a software-guided anal. was developed to assess the relative amt. of the C-2 diastereomers of naringin. A sigmoid curve was obtained showing variation from 94% of (2S)-naringin in very immature fruits to 69.7% in mature fruit samples. Spontaneous epimerization of (2S)-naringin in the ethanolic solns. of the albedo was noted after prolonged keeping for less acid samples. The sepn. of the C-2 diastereomers of other flavanoid-7-O-glycosides present in Citrus (neoeriocitrin, neohesperidin, and eriocitrin) was also obtained by chiral HPLC and afforded the identification, including stereochem., of the eluting peaks in the HPLC traces of the albedo exts.

Abstract

Racemization at C-2 of Naringin in Sour Oranges with Increasing Maturity Determined by Chiral High-Performance Liquid Chromatography. Caccamese, Salvatore; Bianca, Salvatore; Santo, Davide. Dipartimento di Scienze Chimiche, Universita di Catania, Catania, Italy. Journal of Agricultural and Food Chemistry (2007), 55(10), 3816-3822. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 147:29770 AN 2007:390851 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


of ERK 1/2 and p38MAPK signaling pathways. Finally, oral administration of flavanone and 2'-OH flavanone were evidenced by its inhibition on the metastasis of A549 cells and Lewis lung carcinoma (LLC) cells in vivo. In conclusion, flavanone and 2'-OH flavanone perturb the invasion and metastasis of lung cancer cells, thereby constituting an adjuvant treatment for metastasis control.


flavanone

Answer 258:

The elimination half-life for hesperetin was 3.05±0.91 h and for naringenin 2.31±0.40 h, resp. The mean values of the relative cumulative urinary excretion, as percentage of the administered dose, for hesperetin and naringenin, were 3.26±0.44 and 5.81±0.81%, resp. Conclusions: Oral administration of the flavanone aglycons, hesperetin and naringenin, lead to their rapid absorption as their conjugated forms. The cumulative urinary recovery data indicated low bioavailability for both flavanone aglycons, owing to extensive first-pass metab. partly by cleavage of the C-ring by the enzymes of intestinal bacteria leading to degrdn. products such as phenolic acids.

Background and objective: Hesperetin and naringenin, the aglycons of the flavanone glycosides hesperidin and naringin, occur naturally in citrus fruits. They exert interesting pharmacol. properties such as antioxidant, anti-inflammatory, blood lipid and cholesterol lowering and are considered to contribute to health benefits in humans. However, no information is available on the pharmacokinetics of the citrus flavanones hesperetin and naringenin after their oral administration to humans as pure aglycons. Therefore, the objective of the present investigation was the evaluation of the pharmacokinetic parameters of hesperetin and naringenin in plasma and urine, after their single oral administration in humans in the form of solid dispersion capsules, and also to improve the absorption rate of flavanones by using aglycons rather than the naturally occurring glycosides. Design: Six healthy volunteers received orally 135 mg of each compd., hesperetin and naringenin, under fasting conditions. Blood samples were collected at 14 different time points over a 12 h period. Urine was collected over 24 h, in five sequential timed intervals. Plasma and urine hesperetin and naringenin concns., after enzymic hydrolysis of their conjugated forms, were measured using validated high-pressure liq. chromatog. methods. Pharmacokinetic parameters for hesperetin and naringenin, such as Cmax, Tmax, AUC0-t, AUC0-∞, CL/F, V/F, t1/2, MRT, Ae, Ae(0-24), and Rmax were calcd. from their plasma or urine concns. Results: Pharmacokinetic anal. showed that both hesperetin and naringenin were rapidly absorbed and their concns. in plasma obsd. 20 min after dosing and reached a peak in 4.0 and 3.5 h, resp. The mean peak plasma concn. (Cmax) for hesperetin and naringenin were 825.78±410.63 ng/mL (2731.8±1358.4 nmol/l) and 2009.51±770.82 ng/mL (7386.6±2833.4 nmol/l), resp. and the mean AUC0-∞ values were 4846.20±1675.99 ng h/mL and 9424.52±2960.52 ng h/mL for hesperetin and naringenin, resp.

Abstract

Pharmacokinetics of the citrus flavanone aglycones hesperetin and naringenin after single oral administration in human subjects. Kanaze, F. I.; Bounartzi, M. I.; Georgarakis, M.; Niopas, I. Department of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki, Greece. European Journal of Clinical Nutrition (2007), 61(4), 472-477. Publisher: Nature Publishing Group, CODEN: EJCNEQ ISSN: 0954-3007. Journal written in English. CAN 147:314137 AN 2007:373993 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Lutein is assumed to protect the human retina from blue light and oxidative stress and diminish the incidence of age-related macular degeneration. This antioxidant is commonly ingested with other dietary antioxidants. The aim of the present study was to assess whether the main dietary antioxidants, i.e. carotenoids, polyphenols and vitamins C and E, affect lutein absorption. We measured the effect of adding a mixt. of antioxidants (500 mg vitamin C, 67 mg (100 IU) vitamin E and 1 g polyphenols) to a lutein-contg. meal (18 mg) on the postprandial lutein response in the chylomicron-rich fraction in eight healthy men. Lutein response was weakest (-23 %; P = 0⋅07) after ingestion of the meal contg. antioxidants (21⋅9 (SEM 4⋅6) v. 28⋅4 (SEM 7⋅2) nmol × h/l). To assess the effect of each class of antioxidants and potential interactions, the authors subsequently evaluated the effect of various combinations of antioxidants on lutein uptake by human intestinal Caco-2 TC-7 cells. A full factorial design showed that both a mixt. of polyphenols (gallic acid, caffeic acid, (+)-catechin and naringenin) and a mixt. of carotenoids (lycopene plus β-carotene) significantly (P<0⋅05) impaired lutein uptake by (-10 to -30 %), while vitamins C and E had no significant effect. Subsequent expts. showed that the aglycon flavanone naringenin was the only polyphenol responsible for the effect of the polyphenol mixt., and that the carotenoid effect was not carotenoid species-dependent. Taken together, the present results suggest that lutein absorption is not markedly affected by physiol. concns. of vitamins C and E but can be impaired by carotenoids and naringenin.

Abstract


flavanone

Abstract

Methods of analysis and separation of chiral flavonoids. Yanez, Jaime A.; Andrews, Preston K.; Davies, Neal M. College of Pharmacy, Department of Pharmaceutical Sciences and Pharmacology and Toxicology Graduate Program, Washington State University, Pullman, WA, USA. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2007), 848(2), 159-181. Publisher: Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal; General Review written in English. CAN 146:437208 AN 2007:341033 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


From Radix Glycyrrhizae, five compds. were isolated and identified as: quercetin(1), liquorice(2), ferulaic acid(3), 5, 7, 3', 4'-tetrahydroxy- 7-glu-flavanone(4), 8, 5'-dihydroxy-3'-α-rha-flavone(5). Compds. 4 and 5 were isolated from this plant for the first time.

Abstract

Studies on chemical constituents of Glycyrrhiza uralensis Fisch. Wu, Hankui; Zhao, Yun; Mou, Xinli; Ba, Hang; Hajiakber, Aisa. Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Wurumuqi, Peop. Rep. China. Tianran Chanwu Yanjiu Yu Kaifa (2006), 18(3), 415-417. Publisher: Tianran Chanwu Yanjiu Yu Kaifa Bianjibu, CODEN: TCYKE5 ISSN: 1001-6880. Journal written in Chinese. CAN 147:443797 AN 2007:357910 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Otitis externa in dogs and cats is always caused by a combination of yeasts and bacteria, among which the most important are Malassezia pachydermatis, Staphylococcus intermedius and Pseudomonas species. These organisms often develop resistance to classical antimicrobial agents. Therefore, the aim of this study was to investigate the antimicrobial activities of an Et acetate leaf ext. of Harungana madagascariensis against the organisms cited, to carry out the phytochem. investigation of this ext. and to det. its bioactive chem. class using diln. techniques, the bioautog. method and the std. phytochem. method described by Harborne (1973). Phytochem. anal. revealed the presence of saponins, tannins, flavonoids, alkaloids and anthracenic derivs. The bioassay showed that the antimicrobial properties may be attributed to astilbin, a flavanone deriv. identified on the basis of its spectroscopic data. The results suggest that the ext. could be used in an antimicrobial prepn. effective against the whole range of organisms incriminated in otitis externa in dogs and cats, with a minimal inhibitory concn. (MIC) of 250 μg/mL.

Abstract

In vitro antimicrobial activity of the leaf extract of Harungana madagascariensis Lam. ex poir. (Hypericaceae) against strains causing otitis externa in dogs and cats. Moulari, B.; Pellequer, Y.; Chaumont, J.-P.; Guillaume, Y. C.; Millet, J. Equipe Sciences Separatives et Biopharmaceutiques EA-3924, UFR de Medecine et de Pharmacie, Universite de Franche-comte, Besancon, Fr. Acta Veterinaria Hungarica (2007), 55(1), 97-105. Publisher: Akademiai Kiado, CODEN: AVHUEA ISSN: 0236-6290. Journal written in English. CAN 147:318133 AN 2007:373264 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT,


Basic helix-turn-helix transcription factor Rc controlling red or white pigmentation in rice pericarp and seed coat. McCouch, Susan; Sweeney, Megan. (Cornell Research Foundation, Inc., USA). PCT Int. Appl. (2007), 222pp. CODEN: PIXXD2 WO 2007033370 A2 20070322 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SV, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US36020 20060914. Priority: US 2005-717060 20050914. CAN 146:373746 AN 2007:328168 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new synthetic polymeric chiral stationary phase for liq. chromatog. was prepd. via free-radical-initiated polymn. of trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide. The new polymeric chiral stationary phase (CSP) showed enantioselectivity for many chiral compds. in multiple mobile phases. High stability and sample capacities were obsd. on this polymeric chiral stationary phase. Mobile phase components and additives affected chiral sepn. greatly. This new synthetic chiral stationary phase is complementary to two other related com. available CSPs: the P-CAP and P-CAP-DP columns. Interactions between the chiral stationary phase and analytes that lead to retention and chiral recognition include hydrogen bonding, dipolar, and π-π interactions. Repulsive (steric) interactions also contribute to chiral recognition.

Abstract

Preparation and evaluation of a new synthetic polymeric chiral stationary phase for HPLC based on the trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide monomer. Han, Xinxin; Wang, Chunlei; He, Lingfeng; Beesley, Thomas E.; Armstrong, Daniel W. Chemistry & Biochemistry Department, The University of Texas at Arlington, Arlington, TX, USA. Analytical and Bioanalytical Chemistry (2007), 387(8), 2681-2697. Publisher: Springer, CODEN: ABCNBP ISSN: 1618-2642. Journal written in English. CAN 146:533594 AN 2007:331591 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Although the anal. of the enantiomers and epimers of chiral flavanones has been carried out for over 20 years, there often remains a deficit within the pharmaceutical, agricultural, and medical sciences to address this issue. Hence, despite increased interest in the potential therapeutic uses, plant physiol. roles, and health-benefits of chiral flavanones, the importance of stereoselectivity in agricultural, nutrition, pharmacokinetic, pharmacodynamic, pharmacol. activity and disposition has often been ignored. This review presents both the general principles that allow sepn. of chiral flavanones, and discusses both the advantages and disadvantages of the available chromatog. assay methods and procedures used to sep. quantify flavanone enantiomers and epimers in biol. matrixes.


flavanone

Spectral assignments and reference data NMR assignments of unusual flavonoids from the kino of Eucalyptus citriodora. Freitas, Marinalva Oliveira; Lima, Mary Anne S.; Silveira, Edilberto R. Curso de Pos-Graducao em Quimica Organica, Departamento de Quimica Organica e Inorganica, Centro de Ciencias, Universidade Federal do Ceara, Fortaleza, Brazil. Magnetic Resonance in Chemistry (2007), 45(3), 262-264. Publisher: John Wiley & Sons Ltd., CODEN: MRCHEG ISSN: 0749-1581. Journal written in English. CAN 146:481840 AN 2007:325198 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. constituents in the seeds of Euryale ferox Salisb were investigated for obtaining more comprehensive understanding on its effective components. Compds. were sepd. by reversed-phase column chromatog. with silica gel and Pharmadex LH-20 gel. Their structures were elucidated by spectral anal. and chem. evidence. Seven compds. and a mixt. of two compds. were obtained. Their structures were identified as: cyclo(proline-serine) (compd. 1), cyclo(isoleucine-alanine) (compd. 2), cyclo(leucine-alanine) (compd. 3), 5,7,4'-trihydroxyl flavanone (compd. 4), 5,7,3',4',5'-pentahydroxyl flavanone (compd. 5), isolariciresinol-9-O-β-D-glucopyranoside (compd. 6), α-tocopherol (compd. 7), β-locopherol (compd. 8), and δ-tocopherol (compd. 9). Compd. 1 was isolated from natural sources for the first time. Compds. 2-6 was isolated from this plant for the first time.

Abstract

Chemical constituents of Euryale ferox seed. Li, Mei-Hong; Yang, Xue-Qiong; Wan, Zhi-Jian; Yang, Ya-Bin; Li, Fan; Ding, Zhong-Tao. Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Peop. Rep. China. Zhongguo Tianran Yaowu (2007), 5(1), 24-26. Publisher: Zhongguo Tianran Yaowu Bianjibu, CODEN: ZTYHA7 ISSN: 1672-3651. Journal written in Chinese. CAN 147:474475 AN 2007:327043 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention relates to the prodn. of red pericarp and seed coat in rice, and in particular, compns. comprising a basic helix-turn-helix red anthocyanin transcription factor, Rc, and methods using Rc for identifying rice germplasm comprising Rc including but not limited to grain quality grading and seed certification anal. Nucleic acid and amino acid sequences are provided for Rc alleles in rice varieties. Single nucleotide polymorphisms are discovered that when present indicate that red pigmentation will not be produced when when nucleotide sequences the Rc transcriptional protein are present. Also, novel PCR primers are provided for identifying rice germplasm indicating the potential for red and non-red pigmentation i rice pericarp and seed coat. The present invention further relates to promoter sequences of Rc binding elements including but not limited to regulatory elements of genes assocd. with anthocyanidin/proanthocyanidin pathways and the use of these elements for controlling weedy red rice plants and controlling the spread of transgenes into weedy red rice plants.



TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW


flavanone

Isolation and characterization of flavanone glycoside 4',5,7-trihydroxy flavanone rhamnoglucose from Garcinia kola seeds. Okwu, D. E.; Morah, F. N. I. Department of Chemistry, Michael Okpara University of Agriculture Umudike, Nigeria. Journal of Applied Sciences (2007), 7(2), 306-309. Publisher: Asian Network for Scientific Information, CODEN: JASODW ISSN: 1812-5654. Journal written in English. CAN 147:498864 AN 2007:299609 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In A. thaliana, silencing of hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyl transferase (HCT), a lignin biosynthetic gene, results in a strong redn. of plant growth. In HCT-silenced plants, lignin synthesis repression leads to the redirection of the metabolic flux into flavonoids through chalcone synthase activity. Several flavonol glycosides and acylated anthocyanin were shown to accumulate in higher amts. in silenced plants. By contrast, sinapoylmalate levels were barely affected, suggesting that the synthesis of that phenylpropanoid compd. might be HCT-independent. The growth phenotype of HCT-silenced plants was shown to be controlled by light and to depend on chalcone synthase expression. Histochem. anal. of silenced stem tissues demonstrated altered tracheary elements. The level of plant growth redn. of HCT-deficient plants was correlated with the inhibition of auxin transport. Suppression of flavonoid accumulation by chalcone synthase repression in HCT-deficient plants restored normal auxin transport and wild-type plant growth. By contrast, the lignin structure of the plants simultaneously repressed for HCT and chalcone synthase remained as severely altered as in HCT-silenced plants, with a large predominance of nonmethoxylated H units. Thus, the reduced size phenotype of HCT-silenced plants is not due to the alteration of lignin synthesis but to flavonoid accumulation.

Abstract

Flavonoid accumulation in Arabidopsis repressed in lignin synthesis affects auxin transport and plant growth. Besseau, Sebastien; Hoffmann, Laurent; Geoffroy, Pierrette; Lapierre, Catherine; Pollet, Brigitte; Legrand, Michel. Institut de Biologie Moleculaire des Plantes, Laboratoire Propre du Centre National de la Recherche Scientifique, Unite Propre de Recherche 2357, Conventionne a l'Universite Louis Pasteur, Strasbourg, Fr. Plant Cell (2007), 19(1), 148-162. Publisher: American Society of Plant Biologists, CODEN: PLCEEW ISSN: 1040-4651. Journal written in English. CAN 147:27029 AN 2007:318450 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O p-C 6H4 OH

OH

O

Me

p-C 6H4

OH

OH

RO

I

Two unusual flavonoids, 3,5,4',5''-tetrahydroxy-7-methoxy-6-[1-(p-hydroxy-phenyl)ethyl]flavanone (I, R = Me) and 3,5,7,4',5''-pentahydroxy-6-[1-(p-hydroxy-phenyl)ethyl]flavanone (I, R=H ), were isolated from the kino of Eucalyptus citriodora. Structural elucidation of the new compds. were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H, 1H-COSY, HMQC, HMBC).

Abstract


flavanone

Answer 269:

Several novel analogs of Abyssinone II, a naturally occurring prenylated flavanone, were synthesized using isoprene as source of isoprenyl group. This synthesis involves prenylation of p-hydroxybenzaldehyde using prenyl bromide, formation of prenylated polyhydroxychalcone and cyclization to 1, 1I and III. Flavanones IV and V were synthesized using Stille coupling. The compds. were tested in Hela 5 cells using a recombinant a-galactosidase expressing strain of HSV-1(Herpes simplex virus Type 1). The ONPG (ortho-nitrophenol galactoside) viral entry assay was used to measure the viral entry into the treated and untreated cells. The syntheses of analogs I-V will be presented along with antiviral data.

Abstract

Synthesis and antiviral activity of Abyssinone II analogs. Moriarty, Robert M.; Surve, Bhushan C.; Naithani, Rajesh; Chandersekera, Susantha N.; Tiwari, Vaibhav; Shukla, Deepak. Department of Chemistry, University of Illinois, Chicago, IL, USA. Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL, United States, March 25-29, 2007 (2007), MEDI-063. Publisher: American Chemical Society, Washington, D. C CODEN: 69JAUY Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2007:295496 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The flavanone core is abundant in natural products that possess significant bioactivity, including anti-tumor, anti-inflammatory, and aromatase inhibition. A limited no. of strategies have been developed for the asym. synthesis of flavanones, including resoln. of the related alcs., or displacement reactions. Our strategy is to incorporate a functional group on the potential substrate (1) that (a) enhances the reactivity of the conjugate acceptor, (b) favors the cyclized flavanones over the acyclic chalcones and (c) provides a second Lewis basic site for interaction with a catalyst. The use of catalytic chiral thioureas catalyzed the asym. conjugate addn. of 1 to form 2 in high yield with excellent enantioselectivity. The scope and details of the process will be presented.

Abstract

Catalytic enantioselective synthesis of flavanones and chromanones. Scheidt, Karl A.; Biddle, Margaret. Department of Chemistry, Northwestern University, Evanston, IL, USA. Abstracts of Papers, 233rd ACS National Meeting, Chicago, IL, United States, March 25-29, 2007 (2007), ORGN-598. Publisher: American Chemical Society, Washington, D. C CODEN: 69JAUY Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2007:296624 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The ethanolic ext. of Garcinia kola, Heckel (Guttiferae), which had previously been shown to have biol. activity were studied. Preliminary phytochem. screening of the plants showed the presence of flavonoids, phenolic compds., tannins and saponins. The ethanolic ext. of Garcinia kola seeds resulted in the isolation and characterization of flavanone glycoside 4',5,7-trihydroxyflavonone rhamnoglucose (that is naringin-7-rharmnoglucoseside) from its spectral data. 1H NMR spin system anal. and acid hydrolysis were performed to characterize the higher order rhamnoglucosyl moiety comprising glucose and rhamnose linked to carbon 7 of the flavanone ring system of the isolate. It is concluded that 4',5,7-trihydroxyflavanone rhamnoglucose may be a contributor to the antioxidants, anti-inflammatory, anti-microbial, anti-tumor and anti-hepatotoxic properties exhibited by Garcinia kola seed.

Abstract


flavanone

O

O

OH

OHHO

I

7,3',5'-Trisubstituted flavanones and flavonols were synthesized by esterification, acetylation, methoxymethyl protection or methylation, hydrazidation, oxidn., aldol condensation, cyclization, Algar-Flynn-Oyamada reaction and deprotection, using 3,5-dihydroxybenzoic acid and resorcinol as the starting materials in overall yield of 21 % .apprx. 32 %. Their structures were confirmed by 1HNMR, IR and mass spectra. The compd. I, a new natural flavanone isolated from the medicinal plant Caragana intermedia Kang et H. C. Fu, was firstly synthesized.

Abstract

Synthesis of 7,3',5'-trisubstituted flavanones and flavonols. Wang, Qiu-an; Fang, Wei-qin; Liao, Tou-gen. College of Chemistry and Chemical Engineering, Hunan Univ., Changsha, Hunan, Peop. Rep. China. Hunan Daxue Xuebao, Ziran Kexueban (2006), 33(6), 98-102. Publisher: Hunan Daxue Qikanshe, CODEN: HDAXE3 Journal written in Chinese. CAN 147:448550 AN 2007:274383 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Mol. anal. of gene expression differences between green and red lettuce leaves was performed using the SSH method. BlastX comparisons of subtractive expressed sequence tags (ESTs) indicated that 7.6% of clones encoded enzymes involved in secondary metab. Such clones had a particularly high abundance of flavonoid-metab. proteins (6.5%). Following SSH, 566 clones were rescreened for differential gene expression using dot-blot hybridization. Of these, 53 were found to overexpressed during red coloration. The up-regulated expression of six genes was confirmed by Northern blot analyses. The expression of chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), and dihydroflavonol 4-reductase (DFR) genes showed a pos. correlation with anthocyanin accumulation in UV-B-irradiated lettuce leaves; flavonoid 3',5'-hydroxylase (F3',5'H) and anthocyanidin synthase (ANS) were expressed continuously in both samples. These results indicated that the genes CHS, F3H, and DFR coincided with increases in anthocyanin accumulation during the red coloration of lettuce leaves. This study show a relationship between red coloration and the expression of up-regulated genes in lettuce. The subtractive cDNA library and EST database described in this study represent a valuable resource for further research for secondary metab. in the vegetable crops.

Abstract

Genes up-regulated during red coloration in UV-B irradiated lettuce leaves. Park, Jong-Sug; Choung, Myoung-Gun; Kim, Jung-Bong; Hahn, Bum-Soo; Kim, Jong-Bum; Bae, Shin-Chul; Roh, Kyung-Hee; Kim, Yong-Hwan; Cheon, Choong-Ill; Sung, Mi-Kyung; Cho, Kang-Jin. Research Planning & Information Division, National Institute of Agricultural Biotechnology, Suwon, S. Korea. Plant Cell Reports (2007), 26(4), 507-516. Publisher: Springer, CODEN: PCRPD8 ISSN: 0721-7714. Journal written in English. CAN 146:497107 AN 2007:282564 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Synthesis of 5,7-dihydroxyflavanone [i.e, 2,3-dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one] using palladium/carbon as catalyst. The effects of reaction time, reaction temp. and amt. of catalyst on the reaction were discussed. The optimized reaction conditions were: reaction temp. 53°, reaction time 2h and catalyst 1.0 g. The yield of the reaction was 83.26%.

Abstract

Synthesis of 5,7-dihydroxyflavanone. Cheng, Yong-hao; Duan, Ya-bo; Qi, Yan; Guo, Xiao-yun; Tong, Yuan-feng; Du, Guan-hua; Wu, Song. Inst. Materia Med., Chinese Acad. Med. Sci. and Peking Union Med. Coll., Beijing, Peop. Rep. China. Huaxue Shiji (2006), 28(7), 437-438. Publisher: Huaxue Shiji Bianjibu, CODEN: HUSHDR ISSN: 0258-3283. Journal written in Chinese. CAN 148:144537 AN 2007:270146 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new brush-type HPLC chiral stationary phase (CSP) comprising π-acidic N-(3,5-dinitrobenzoyl)-D-α-phenylglycine chiral units bound to the quinoxaline units of modified γ-aminopropyl silica gel by a 1,2-diaminoethane spacer was prepd. by solid-phase synthesis. To test the CSP attempts were made to sep. the enantiomers of twenty-two racemates with different functional groups and the results were compared with those obtained using three structurally related chiral stationary phases.

Abstract

Performance of a new HPLC chiral stationary phase derived from N-(3,5-dinitrobenzoyl)-D-α-phenylglycine with a quinoxaline branching unit. Forjan, D. Moslavac; Vinkovic, V.; Kontrec, D. Laboratory for Stereoselective Catalysis and Biocatalysis, Rudjer Boskovic Institute, Zagreb, Croatia. Acta Chromatographica (2006), 17 97-107. Publisher: Silesian University, Institute of Chemistry, CODEN: ATCREU ISSN: 1233-2356. Journal written in English. CAN 147:397402 AN 2007:270224 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The objective is to in order to make use of the resources of onion, avoid wasting and approach the extn. of total flavanone of onion. The flavonoids were extd. by ethanol as the solvent from onion with ultrasonic wave and ethanol extn. Spectrophotometry used in the ext. and check the flavanone of onion. By this method getting the c d. of the total flavanone of onion is C=20.58% and the rate of av. recovery is 102.1%. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone are all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone of onion.

Abstract

The total flavanone of onion extraction and the identification by ultrasonic wave. Huang, Suo-yi; Luo, Jian-hua; Feng, Ling. Department of Chemistry, Youjiang Medical College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2007), 24(1), 31-33. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 147:116949 AN 2007:270798 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The title flavanone compd. (I, R1 = H or CH3; R2 = H or CH3; R3 = H or OH) can be used for treating cardiovascular disease, such as myocardial infarction, angina pectoris, hypertension, arteriosclerosis, hyperlipemia, and coronary artery disease. The flavanone compds. are extd. from Blumea balsamifera. The content of flavanone in unit formulation is 5-1000 mg.


Application of flavanone compound in medicine for treating cardiovascular disease. Zhao, Jinhua; Kang, Hui; Yao, Guanghui; Zeng, Weizhen; Liu, Xiaorou; Li, Jing; Feng, Hanlin; Yu, Lin. (Shenzhen Neptunus Pharmaceutical Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 13pp. CODEN: CNXXEV CN 1923191 A 20070307 Patent written in Chinese. Application: CN 1009-3643 20050831. Priority: . CAN 146:365638 AN 2007:265819 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The relation between 5 classes of flavonoids (flavanones, flavan-3-ols, flavonols, flavones and anthocyanidines) and esophageal cancer was investigated using data from a case-control study conducted between 1992 and 1997 in 3 areas of northern Italy. The study included 304 cases (275 men, 29 women) with a first diagnosis of squamous-cell carcinoma of the esophagus and 743 controls (593 men, 150 women) with no history of cancer, admitted for acute illnesses, unrealted to tobacco and alc. consumption, to major hospitals of the areas under surveillance. Dietary habits were investigated using a validated food frequency questionnaire. Odds ratios (ORs) and 95% confidence intervals (CI) were computed after allowance for age, sex, study center, years of education, alc. drinking, tobacco smoking, body mass index and energy intake. An inverse assocn. emerged between flavanone intake and esophageal cancer risk (OR = 0.38 for the highest vs. the lowest quintile, 95% CI = 0.23-0.66). The inverse relation between flavanones and esophageal cancer tended to be stronger in those who drank ≥6 drinks/day. In conclusion, this study suggests that flavanone intake is inversely assocd. with esophageal cancer risk and may account, with vitamin C, for the protective effect of fruit, esp. citrus fruit, on esophageal cancer.

Abstract

Flavonoids and risk of squamous cell esophageal cancer. Rossi, Marta; Garavello, Werner; Talamini, Renato; La Vecchia, Carlo; Franceschi, Silvia; Lagiou, Pagona; Zambon, Paola; Dal Maso, Luigino; Bosetti, Cristina; Negri, Eva. Istituto di Ricerche Farmacologiche "Mario Negri", Milan, Italy. International Journal of Cancer (2007), 120(7), 1560-1564. Publisher: Wiley-Liss, Inc., CODEN: IJCNAW ISSN: 0020-7136. Journal written in English. CAN 146:273425 AN 2007:269135 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Nonracemic dihydrobenzopyranones I (R = Ph, 2-ClC6H4, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, cyclohexyl, PhCH2CH2; R1 = H, Me, MeO; R2 = H; R1R2 = CH:CHCH:CH) are prepd. in 65-92% yields and in 78-94% ee by cyclization of the (E)-(hydroxyaroyl)propenoates II (R = Ph, 2-ClC6H4, 4-MeC6H4, 4-MeOC6H4, 4-BrC6H4, cyclohexyl, PhCH2CH2; R1 = H, Me, MeO; R2 = H; R1R2 = CH:CHCH:CH) in the presence of nonracemic thiourea III followed by acid-mediated decarboxylation in the presence of either p-toluenesulfonic acid or magnesium bromide-diethyl ether complex. I (R = PhCH2CH2; R1 = R2 = H) is prepd. in 77% yield and 80% ee in one pot from 2-HOC6H4COCH2CO2CMe3 and hydrocinnamaldehyde using a nonracemic thiourea catalyst; the one-pot procedure avoids difficultly-sepd. byproducts of nonselective cyclization formed in the Knoevenagel condensation reactions of alkyl aldehydes with hydroxyaroylacetates. The structure of II (R = 4-BrC6H4; R1 = R2 = H) is detd. by X-ray crystallog.

Abstract

Catalytic Enantioselective Synthesis of Flavanones and Chromanones. Biddle, Margaret M.; Lin, Michael; Scheidt, Karl A. Department of Chemistry, Northwestern University, Evanston, IL, USA. Journal of the American Chemical Society (2007), 129(13), 3830-3831. Publisher: American Chemical Society, CODEN: JACSAT ISSN: 0002-7863. Journal written in English. CAN 146:500844 AN 2007:262387 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

O

OH

OH

R1

R3

OR 2

I


flavanone

Conditions in the parental environment during reprodn. can affect the performance of the progenies. The goals of this study were to investigate whether warm or cold temps. in the parental environment during flowering and seed development affect Arabidopsis thaliana seed properties, growth performance, reprodn. and stress tolerance of the progenies, and to find candidate genes for progeny-related differences in stress responsiveness. Parental plants were raised at 20 °C and maintained from bolting to seed maturity at warm (25 °C) or cold (15 °C) temps. Anal. of seed properties revealed significant increases in nitrogen in seeds from warm temp. and significant increases in lipids and in the ratio of α-linolenic to oleic acid in seeds from the cold parental environment. Progenies of the warm parental environment showed faster germination rates, faster root elongation growth, higher leaf biomass and increased seed prodn. at various temps. compared with those from the cold parental environment. This indicates that under stable environmental conditions, progenies from warm parental environments had a clear adaptive advantage over those from cold parental environments. This parental effect was presumably transmitted by the higher nitrogen content of the seeds developed in warm conditions. When offspring from parents grown at different temps. were exposed to chilling or freezing stress, photosynthetic yield recovered faster in progenies originating from cold parental environments. Cold acclimation involved up-regulation of transcripts of flavanone 3-hydroxylase (F3H) and pseudo response regulator 9 (PRR9) and down-regulation of growth-assocd. transcription factors (TFs) NAP and AP2 domain contg. RAP2.3. NAP, a regulator of senescence, and PRR9, a temp.-sensitive modulator of the circadian clock, were probably involved in

Abstract

Warm and cold parental reproductive environments affect seed properties, fitness, and cold responsiveness in Arabidopsis thaliana progenies. Bloedner, C.; Goebel, C.; Feussner, I.; Gatz, C.; Polle, A. Institut fuer Forstbotanik, Georg-August Universitaet Goettingen, Germany. Plant, Cell and Environment (2007), 30(2), 165-175. Publisher: Blackwell Publishing Ltd., CODEN: PLCEDV ISSN: 0140-7791. Journal written in English. CAN 147:360853 AN 2007:260702 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

O

C

N

H2C

HO

N

N

S

NH

CF 3

CF 3H

R1

2R

R 1

2R

R

R

O2CMe 3

PhCH 2

I

III

II


flavanone

A tunable ESI-MS/MS strategy for differentiation of flavone and flavanone diglycoside isomers based on metal complexation with auxiliary ligands is reported. The addn. of a metal salt and an auxiliary ligand to a flavonoid soln. results in the formation of [M(II) (flavonoid-H) auxiliary ligand]+ complexes, where M(II) is a transition metal. A series of auxiliary ligands with electron-withdrawing

Abstract

Tunable Transition Metal-Ligand Complexation for Enhanced Elucidation of Flavonoid Diglycosides by Electrospray Ionization Mass Spectrometry. Pikulski, Michael; Aguilar, Apolonio; Brodbelt, Jennifer S. Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX, USA. Journal of the American Society for Mass Spectrometry (2007), 18(3), 422-431. Publisher: Elsevier Inc., CODEN: JAMSEF ISSN: 1044-0305. Journal written in English. CAN 146:353990 AN 2007:229069 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The ext. method for total flavanone from mango leaves was studied in order to make full use of the resources of mango leaves. The flavanone was extd. by ethanol from mango leaves with ultrasonic wave and detd. by spectrophotometry. The d. amt. of the total flavanone of ext. from mango leaves was 2.900 mg/mL and the recovery was 100.2%. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone from mango leaves.

Abstract

Extraction of total flavanone from mango leaves by ultrasonic wave. Huang, Suo-yi; Li, Hai-ni; Tang, Yu-lian; Zhang, Jing-xuan. Department of Chemistry, Youjiang Ethnic Medical College, Baise, Peop. Rep. China. Zhongguo Xiandai Yingyong Yaoxue (2006), 23(6), 455-456. Publisher: Zhongguo Xiandai Yingyong Yaoxue Zazhi Bianji Weiyuanhui, CODEN: ZXYYAI ISSN: 1007-7693. Journal written in Chinese. CAN 147:78985 AN 2007:243250 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. A discussion on the need for artificial sweeteners and the parameters that should be considered with regard to intense sweetener. These parameters include: stability in heat and pH, soly., taste profile, toxicity, and the possibility of use in combination with bulk sweeteners, bulking agents and preserving agents.

Abstract

Artificial sweetener. Abushqara, Elias. R&D Department, Frutarom, Haifa, Israel. Speciality Chemicals Magazine (2007), 27(1), 26-28. Publisher: DMG World Media (uk) Ltd., CODEN: SPCHEY ISSN: 0262-2262. Journal; General Review written in English. CAN 147:299532 AN 2007:246225 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


also delay senescence, cold responsiveness of NAP suggests that this factor is linked with the regulatory network that is important for environmental acclimation of plants.

mediating parent-of-origin effects, because they showed progeny-related expression differences under chilling. Because low temps.


flavanone

Construction of a flavonoid database for assessing intake in a population-based sample of women on Long Island, New Bibliographic Information Answer 283:

The effect of time and temp. on the content of vitamin C, total polyphenols and individual phenolic compds. as well as on the antioxidant activity of two com. orange juices was studied. The polyphenol content was detd. using Folin-Ciocalteu and HPLC methods. The two methods, SPE vs. direct injection following a simple treatment of samples, were compared to assess two techniques of sample prepn. For antioxidant capacity detn., DPPH and FRAP assays were used. All analyses were carried out for fresh juices and after storage at 18, 28 and 38 °C for 2, 4 and 6 mo. It was found that vitamin C and free and conjugated hydroxycinnamic acids were the most affected by both duration and temp. of storage. The decrease in the content of polyphenols and vitamin C upon storage was reflected by the decrease in the antioxidant capacity of orange juices. Small changes in flavanone content were obsd., indicating high stability of these compds. upon storage.

Abstract

Effect of storage on the content of polyphenols, vitamin C and the antioxidant activity of orange juices. Klimczak, Inga; Malecka, Maria; Szlachta, Miroslawa; Gliszczynska-Swiglo, Anna. Faculty of Commodity Science, Poznan University of Economics, Poznan, Pol. Journal of Food Composition and Analysis (2007), 20(3-4), 313-322. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575. Journal written in English. CAN 147:342869 AN 2007:188200 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids are non-nutrient plant phenolic compds. proposed to provide health benefits in humans. The antioxidant and prooxidant effects of the citrus flavanone naringenin have been tested only in vitro. The dose-response effect of naringenin consumption was tested in weanling rats (n = 6-8/group) with a 2 × 4 factorial design using high or low oxidative stress (Hox or Lox, resp.) diets, created by adequate or deficient amts. of vitamin E and selenium, with three increasing naringenin concns. (30, 60, or 120 mg/kg of diet). Hox compared to Lox rats exhibited reduced growth and liver hypertrophy, which was not prevented by naringenin consumption. Also, Hox rats exhibited severalfold higher liver NAD(P)H:quinone oxidoreductase-1 activity, which was further elevated in proportion to naringenin intake, but this was not sufficient to protect against oxidative stress indicated by higher liver total aldehydes. In addn., dietary naringenin did not affect antioxidant nutrient status or physiol. markers of growth under Lox conditions. Thus, dietary naringenin did not exhibit antioxidant or prooxidant effects in vivo in this rat model.

Abstract

Effect of the Citrus flavanone naringenin on oxidative stress in rats. Andrade, Juan E.; Burgess, John R. Department of Foods and Nutrition, Purdue University, West Lafayette, IN, USA. Journal of Agricultural and Food Chemistry (2007), 55(6), 2142-2148. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 146:228371 AN 2007:192309 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


substituents were synthesized to tailor the relative metal binding affinities of the ligands and thus directly influence the stabilities, and consequently the dissocn. pathways, of the complexes. Upon collisionally activated dissocn., the complexes yield fragmentation patterns in which the abundances of key diagnostic ions are enhanced, thus facilitating isomer differentiation.


flavanone

Prohexadione-Ca: modes of action of a multifunctional plant bioregulator for fruit trees. Rademacher, W.; Spinelli, F.; Costa, G. BASF Agricultural Center, Global Research Agricultural Products, Limburgerhof, Germany. Acta Horticulturae (2006), 727(Proceedings of the Xth International Symposium on Plant Bioregulators in Fruit Production, 2005), 97-106. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal; General Review written in English. CAN 146:456702 AN 2007:182302 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Cytochrome P 450s (CYPs) that catalyze arom. hydroxylations, aliph. hydroxylations, and skeleton formation in flavonoid metab. are surveyed. They are involved in the biosynthesis of anthocyanin pigments and condensed tannins CYP75 (flavonoid 3',5'-hydroxylase and 3'-hydroxylase); flavones [CYP93B, (2S)-flavanone 2-hydroxylase and flavone synthase II]; and leguminous isoflavonoid phytoalexins [CYP71D9, flavonoid 6-hydroxylase; CYP81E, isoflavone 2'-hydroxylase and 3'-hydroxylase; CYP93A, 3,9-dihydroxypterocarpan 6a-hydroxylase; and CYP93C, 2-hydroxyisoflavanone synthase (IFS)]. Other P 450s of flavonoid metab. include the methylenedioxy bridge-forming enzyme, cyclases producing glyceollins, flavonol 6-hydroxylase, and 8-dimethylallylnaringenin 2'-hydroxylase. Mechanistic studies on the unusual aryl migration by CYP93C, regulation of IFS expression in plant organs and its biotechnol. applications, and flavonoid metab. by non-plant P 450s are also briefly discussed.

Abstract

Cytochrome P 450s in flavonoid metabolism. Ayabe, Shin-ichi; Akashi, Tomoyoshi. Department of Applied Biological Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa, Japan. Phytochemistry Reviews (2006), 5(2-3), 271-282. Publisher: Springer, CODEN: PRHEBS ISSN: 1568-7767. Journal; General Review written in English. CAN 146:223183 AN 2007:187112 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids have been hypothesized to reduce cancer risk. Previous epidemiol. studies conducted to evaluate this hypothesis have not assessed all flavonoids, including classes that could contribute to intake among Americans, which would result in an underestimation of intake. This misclassification could mask variability among individuals, resulting in attenuated effect ests. for the assocn. between flavonoids and cancer. To augment flavonoid and lignan intake ests., we developed a database that can be used in conjunction with a food-frequency questionnaire (FFQ). Coupling information derived from the available literature with the U.S. Department of Agriculture databases, we estd. content of 6 flavonoid classes and lignans for 50 food group items. We combined these ests. with responses from a modified Block FFQ that was self-completed in 1996-1997 by a population-based sample of women without breast cancer on Long Island, New York (n = 1,500). Total flavonoid and lignan content of food items ranged from 0 to 129 mg/100 g, and the richest sources were tea, cherries, and grapefruit. Individual intake ests., from highest to lowest, were flavan-3-ols, flavanones, flavonols, lignans, isoflavones, anthocyanidins, and flavones. Each class of flavonoids and lignans exhibited a wide range of intake levels. This database is useful to quantify flavonoid and lignan intake for other observational studies conducted in the United States that utilize the Block FFQ.

Abstract

York. Fink, Brian N.; Steck, Susan E.; Wolff, Mary S.; Kabat, Geoffrey C.; Gammon, Marilie D. Department of Epidemiology, School of Public Health, University of North Carolina, Chapel Hill, NC, USA. Nutrition and Cancer (2006), 56(1), 57-66. Publisher: Lawrence Erlbaum Associates, Inc., CODEN: NUCADQ ISSN: 0163-5581. Journal written in English. CAN 146:337124 AN 2007:187528 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Antibacterial Pterocarpans from Erythrina subumbrans. Rukachaisirikul, Thitima; Innok, Phongsak; Aroonrerk, Nuntana; Boonamnuaylap, Woraluk; Limrangsun, Saranya; Boonyon, Chanakan; Woonjina, Umpawan; Suksamrarn, Apichart. Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, Thailand. Journal of Ethnopharmacology (2007), 110(1), 171-175. Publisher: Elsevier B.V., CODEN: JOETD7 ISSN: 0378-8741. Journal written in English. CAN 147:537750 AN 2007:160706 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The comparisons of five different chiral stationary phases (CSPs) based on 2,6-dinitro-4-trifluoromethylphenyl (DNP-TFM) ether substituted β-cyclodextrin are presented. The five CSPs differ from each other in the linkage/spacer chem., or on the position of the substituents on β-cyclodextrin, or in the sequence of the synthetic procedure. There are two optimum combinations: (1) DNP-TFM randomly substituted on the β-cyclodextrin as the chiral selector along with a carbamate linkage chain bonding it to the silica support; and (2) β-cyclodextrin derivatized by DNP-TFM substituents only on the C-2 and C-3 positions of the cyclodextrin with an ether linkage chain anchoring it to the silica gel. These two combinations show complementary sepns. for some enantiomers. The spacer chain effect is much more pronounced for the CSP based on the β-cyclodextrin derivs. with DNP-TFM substituents only on C-2 and C-3 positions than its randomly substituted counterpart. The sequence of derivatizing the cyclodextrin and attaching it to silica gel also affects its selectivity and efficiency. The β-cyclodextrin should be derivatized before it is linked to the silica gel.

Abstract

Optimization of the synthesis of 2,6-dinitro-4-trifluoromethylphenyl ether substituted cyclodextrin bonded chiral stationary phases. Zhong, Q.; He, L.; Beesley, T. E.; Trahanovsky, W. S.; Sun, P.; Wang, C.; Armstrong, D. W. Department of Chemistry, Iowa State University, Ames, IA, USA. Chromatographia (2006), 64(3-4), 147-155. Publisher: Vieweg Verlag/GWV Fachverlage GmbH, CODEN: CHRGB7 ISSN: 0009-5893. Journal written in English. CAN 147:335089 AN 2007:176205 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Prohexadione-Ca is a plant bioregulator that is primarily used to inhibit excessive vegetative growth in fruit trees and other crop plants. Addnl., effects on the incidence of bacterial and fungal diseases and on insect pests are often obsd. Furthermore, the compd. may reduce abortion of fruitlets, thereby increasing fruit set. Prohexadione-Ca is relatively short-lived and possesses very favorable toxicol. and ecotoxicol. features. The compd. acts as a structural mimic of 2-oxoglutaric acid. Therefore, distinct dioxygenases involved in gibberellin biosynthesis, which require this compd. as a co-substrate, are blocked (e.g. GA20 3β-hydroxylase). As a result, less growth-active gibberellins are formed and treated plants remain compact. 2-Oxoglutaric acid-dependent dioxygenases are also involved in flavonoid metab. In shoots of apples and pears, prohexadione-Ca causes considerable changes in the formation of flavonoids and their phenolic precursors by inhibiting flavanone 3-hydroxylase. Prohexadione-Ca triggers pathogen resistance by inducing the formation of 3-deoxyflavonoids, in particular luteoforol, with phytoalexin-like properties. A similar mechanism may explain the lowered incidence of insect pests. Finally, treatments with prohexadione-Ca lead to reduced ethylene formation. This is due to structural similarities with ascorbic acid, the co-substrate of aminocyclopropanecarboxylic acid oxidase, another dioxygenase, which is involved in ethylene biosynthesis. Lowered ethylene levels, together with elevated availability of assimilates that are no longer needed for shoot growth, explains increases in fruit set.

Abstract


flavanone

Prenylflavonoid formulations. Kuhrts, Eric. (Bioactives, Inc., USA). PCT Int. Appl. (2007), 35pp. CODEN: PIXXD2 WO 2007016578 A2 20070208 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO,


A review. I described here two important aspects of pathogenesis of androgenetic alopecia (AGA): (1) Regulators of androgen sensitivity in hair follicles and (2) Sol. mediators involved in AGA pathomechanism. Moreover, we discussed about the therapeutic agents for AGA and their putative action in the pathomechanism.

Abstract

Andrology in the skin: pathogenesis and therapy of androgenetic alopecia. Inui, Shigeki. Dep. Regenerative Dermatol., Course Mol. Med., Grad. Sch. Med., Osaka University, Suita, Japan. Nippon Hifuka Gakkai Zasshi (2006), 116(13), 2142-2146. Publisher: Nippon Hifuka Gakkai, CODEN: NHKZAD ISSN: 0021-499X. Journal; General Review written in Japanese. CAN 147:46163 AN 2007:157617 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Cyclic β-(1→3),(1→6)-glucans, microbial cyclooligosaccharides produced by Bradyrhizobium japonicum USDA 110, were used as novel chiral additives for the enantiomeric sepn. of some flavanones such as eriodictyol, homoeriodictyol, hesperetin, naringenin, and isosakuranetin in capillary electrophoresis (CE). Among the flavanones, eriodictyol was sepd. with the highest resoln. (Rs 5.66) and selectivity factor (α 1.18) when 20 mM cyclic β-(1→3),(1→6)-glucans were added to the background electrolyte (BGE) at pH 8.3.

Abstract

Enantioseparation of some chiral flavanones using microbial cyclic β-(1→3),(1→6)-glucans as novel chiral additives in capillary electrophoresis. Kwon, Chanho; Park, Heylin; Jung, Seunho. Department of Bioscience and Biotechnology, Konkuk University, Seoul, S. Korea. Carbohydrate Research (2007), 342(5), 762-766. Publisher: Elsevier B.V., CODEN: CRBRAT ISSN: 0008-6215. Journal written in English. CAN 146:417655 AN 2007:159212 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Seven pterocarpans, erybraedin B (1), erybraedin A (2), phaseolin (3), erythrabyssin II (4), erystagallin A (5), erythrabissin-1 (6) and erycristagallin (7), two flavanones, 5-hydroxysophoranone (8) and glabrol (9), and one isoflavone, erysubin F (10), were isolated from the stems of Erythrina subumbrans (Leguminosae). Their structures were identified by means of spectroscopy. This is the first report of the isolation of the non-alkaloidal compds. from Erythrina subumbrans and the obsd. dehydration of 6a-hydroxypterocarpans 5 and 6 in CDCl3 to the corresponding pterocarpenes 11 and 12, resp. Compds. 8 and 9 were isolated for the first time from the genus Erythrina. Compds. 2 and 4 exhibited the highest degree of activity against Streptococcus strains with an MIC range of 0.78-1.56 μg/mL, whereas compd. 7 exhibited the highest degree of activity against Staphylococcus strains, including drug-resistant strains (MRSA and VRSA), with an MIC range of 0.39-1.56 μg/mL. Interestingly, compds. 2, 4, 5 and 7 were more active against several strains of Streptococcus and Staphylococcus than the std. antibiotics vancomycin and oxacillin. Compd. 7 showed the highest level of activity against all VRSA strains tested, with an MIC range of 0.39-1.56 μg/mL, which were resistant to both antibiotics. These compds. may prove to be potent phytochem. agents for antibacterial activity, esp. against the MRSA and VRSA strains.


flavanone

Abstract

Characteristics of flavonoids in Niihime fruit - a new sour citrus fruit. Miyake, Yoshiaki. Faculty of Human Wellness, Tokaigakuen University, Nagoya, Japan. Food Science and Technology Research (2006), 12(3), 186-193. Publisher: Japanese Society for Food Science and Technology, CODEN: FSTRFS ISSN: 1344-6606. Journal written in English. CAN 147:187778 AN 2007:149975 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Methods and formulations for increasing the water soly. and/or bioavailability of prenylfiavonoids are disclosed. The formulations may be employed to treat a disease states, including cancer.

Abstract WO 2006-US29962 W 20060731US 2005-703677P P 20050729Priority Application

R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR

EP 1909584 A2 20080416 EP 2006-789123 20060731CA 2617209 A1 20070208 CA 2006-2617209 20060731AU 2006275491 A1 20070208 AU 2006-275491 20060731


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW


CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US29962 20060731. Priority: US 2005-703677 20050729. CAN 146:235839 AN 2007:150925 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Method for producing chrysanthemum cultivar of which flower color is changed from red to yellow according to flowering time, and chrysanthemum cultivar produced thereby. Liu, Jang Ryol; Seo, Jin Wook; Kim, Suk Weon; Oh, Seung Cheol; Cha, Hyun Wook. (Korea Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2006),


O2N

Me

OH N XR1

R

I

Chalcones or flavanones were reacted with ethanol, hydroxylamine hydrochloride and aq. KOH to give isoxazolines I (X = O with R = R1 = H; R = OMe, R1 = H; R = H, R1 = NO2; RR1 = OCH2O). Subsequent reaction with P2S5 under reflux with pyridine gave thioisoxazolines I (X = S; II), while treatment with Ac2O and a pinch of anhyd. NaOAc yields 3-(2-acetoxy)isoxazolines. Thioisoxazolines II reacted with Ac2O in presence of anhyd. NaOAc to give 3-(2-acetoxy)thioisoxazolines.

Abstract

Synthesis and characterization of some nitro-substituted 3,5-diarylisoxazolines, thioisoxazolines, and their derivatives. Parmar, P. J.; Rajput, S. I. Department of Chemistry, B.P. Arts, S.M.A. Science and K.K.C. Commerce College, Chalisgaon, India. Asian Journal of Chemistry (2007), 19(2), 1519-1523. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in English. CAN 148:239076 AN 2007:136951 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Niihime fruit, produced in the coastal area of the Sea of Kumano in Mie prefecture, is a new sour citrus fruit. This is the first study to examine the characteristics of the flavonoids in niihime fruit. The content of flavonoids in the juice and peel of niihime fruit was detd. by HPLC and their distribution was examd. in comparison with seven other species of sour citrus fruits. Niihime fruit was found to contain a comparatively high quantity of bioactive flavonoids of the flavanone glycosides with rutinose sugar chain such as eriocitrin and hesperidin as well as the polymethoxyflavones such as nobiletin and tangeretin. The peel ext. of niihime fruit exhibited comparatively high antioxidative activity among sour citrus fruits using the DPPH radical scavenging assay. Furthermore, the flavonoids eluted from niihime fruit by over time in hot and cold solns. of water, 5% ethanol, and 25% ethanol, which are commonly used in the field of food processing and cooking, were examd. The flavonoids eluted from niihime fruit in hot 25% ethanol soln. was highest content in solns., and the content of flavonoids eluted in 5 min was an approx. half of content eluted in 60 min. The flavanone glycosides, eriocitrin and hesperidin, were eluted in higher contents in hot solns. than in cold solns. The polymethoxyflavones, nobiletin and tangeretin, were eluted to some extent in hot 5% ethanol but were found in low contents in cold solns. The highest contents were eluted in hot 25% ethanol. The difference in the elution properties between flavanone glycosides and polymethoxyflavones is considered to be a result of their hydrophobic properties. The scavenging activity of DPPH radical for eluates was shown to increase over time, and the activity was suggested to be related to the elution content of eriocitrin, which is an antioxidant in niihime fruit. This study showed that niihime fruit contains a comparative abundance of bioactive flavonoids and these flavonoids are able to be eluted using hot solns. of water and ethanol.


flavanone

The title Heterosmilax ext. contains phenolic glycosides not less than 10% and flavonoid glycosides not less than 10%. The title method comprises: (1) extg. Heterosmilax with 10-95% alc., concg., suspending in water, standing, and filtering, (2) performing liq.-liq.


Heterosmilax extract, and its preparation method and application in treating tumors. Lin, Ruichao; Wang, Gangli; Dai, Zhong; Yao, Lingwen; Qin, Wenjie. (National Research Center of Pharmaceutical and Biological Products Standardization, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 19pp. CODEN: CNXXEV CN 1903340 A 20070131 Patent written in Chinese. Application: CN 1008-9055 20060801. Priority: . CAN 146:280892 AN 2007:132062 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method for producing novel Chrysanthemum cultivar and the Chrysanthemum cultivar produced thereby are provided to change the flower color of Chrysanthemum cultivar from red to yellow according to the flowering time by inserting flavonoid 3',5'-hydroxylase gene into the Chrysanthemum cultivar. The method for producing Chrysanthemum cultivar comprises the steps of: (a) inserting the genes assocd. with anthocyanin biosynthesis into the Agrobacterium; (b) inducing the adventitious bud from the cotyledon or embryo axis segment of Chrysanthemum; (c) co-culturing the Agrobacterium of step (a) with the induced adventitious bud to introduce the genes assocd. with anthocyanin biosynthesis into the adventitious bud; (d) selecting the transformed adventitious bud; and (e) regenerating the selected adventitious bud, wherein the gene assocd. with anthocyanin biosynthesis is selected from chalcone synthase (CHS) gene, chalcone isomerase (CHI) gene, flavanone 3-hydroxylase (F3H) gene, flavonoid 3'-hydroxylase (F3'H) gene, flavonoid 3', 5'-hydroxylase (F3',5'H) gene, dihydroflavonol 4-reductase (DFR) gene, anthocyanidin synthase (ANS) gene and flavonoid glucosyl transferase (FGT) gene.


No pp. given. CODEN: KRXXA7 KR 2006080067 A 20060707 Patent written in Korean. Application: KR 2005-609 20050104. Priority: . CAN 146:200227 AN 2007:132135 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The aim of this study was to det. the levels of bioactive compds. in the edible portions of 8 varieties of citrus fruits (Ponkan, Tonkan, Murcott, Wendun, Peiyou, Kumquat, Liucheng, and Lemon) cultivated in Taiwan. The amt. of total polyphenol and flavonoid exceeded

Abstract

Quantitation of bioactive compounds in citrus fruits cultivated in Taiwan. Wang, Yuan-Chuen; Chuang, Yueh-Chueh; Ku, Yu-Hua. Department of Food Science and Biotechnology, National Chung Hsing University, Taichung, Taiwan. Food Chemistry (2007), 102(4), 1163-1171. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 146:294603 AN 2007:125742 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In contrast to M. Shoja et al.'s (1998) crystal structure of 6-hydroxyflavanone, C15H12O3, in the present crystal structure, both S and R enantiomers appear to occupy randomly the 4 crystallog. sites of the unit cell in an .apprx.3:1/1:3 ratio. Crystallog. data are given.

Abstract

Disordered 6-hydroxyflavanone. Bialonska, Agata; Ciunik, Zbigniew; Kostrzewa-Suslow, Edyta; Dmochowska-Gladysz, Jadwiga. Faculty of Chemistry, University of Wroclaw, Wroclaw, Pol. Acta Crystallographica, Section E: Structure Reports Online (2007), E63(2), o430-o431. Publisher: Blackwell Publishing Ltd., CODEN: ACSEBH ISSN: 1600-5368. http://journals.iucr.org/e/issues/2007/02/00/lh2266/lh2266.pdf Journal; Online Computer File written in English. CAN 146:510789 AN 2007:131709 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Unlike the crystals of 4'-hydroxyflavanone, C15H12O3 obtained from a MeOH soln. (Shoja, M., 1998), in crystals grown from a hexane-acetone mixt. (10:1), both the S and R enantiomers appear to occupy in a random way the 4 symmetry-equiv. sites of the unit cell in an .apprx.4:1/1:4 ratio.

Abstract

Disordered 4'-hydroxyflavanone. Bialonska, Agata; Ciunik, Zbigniew; Kostrzewa-Suslow, Edyta; Dmochowska-Gladysz, Jadwiga. Faculty of Chemistry, University of Wroclaw, Wroclaw, Pol. Acta Crystallographica, Section E: Structure Reports Online (2007), E63(2), o432-o433. Publisher: Blackwell Publishing Ltd., CODEN: ACSEBH ISSN: 1600-5368. http://journals.iucr.org/e/issues/2007/02/00/lh2267/lh2267.pdf Journal; Online Computer File written in English. CAN 146:510790 AN 2007:131710 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


extn. with low-polarity solvent (petroleum ether, Et ether, acetone, and isopropanol), medium-polarity solvent (chloroform and/or Et acetate) and high-polarity solvent (n-butanol) in order, and (3) feeding into macroporous resin, eluting with water until the eluate exhibits neg. reducing sugar reaction, eluting with 90% alc. to collect eluate, and concg. The ext. has antitumor activity, and can be used in manuf. of antitumor drugs.


flavanone

A new flavanone from the leaves of Cassia alata. Rahman, M. S.; Hasan, A. J. M. Moynul; Ali, M. Y.; Ali, M. U. BCSIR Laboratories, Rajshahi, Bangladesh. Bangladesh Journal of Scientific and Industrial Research (2005), 40(1-2), 123-126. Publisher: Bangladesh Council of Scientific and Industrial Research, CODEN: BJSIBL ISSN: 0304-9809. Journal written in English. CAN 147:253801 AN 2007:104018 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new dalbergiones (1-2) and a new flavanone (3) were isolated along with nine other known flavonoids (4-12) from the methanolic ext. of propolis collected from Chitwan, Nepal. The structures were detd. on the basis of spectral anal.

Abstract

Chemical constituents of Nepalese propolis: isolation of new dalbergiones and related compounds. Shrestha, Suraj Prakash; Narukawa, Yuji; Takeda, Tadahiro. Kyoritsu University of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo, Japan. Journal of Natural Medicines (2007), 61(1), 73-76. Publisher: Springer Tokyo, CODEN: JNMOBN Journal written in English. CAN 147:360599 AN 2007:120270 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The cycloaddn. reaction of non-stabilized azomethine ylides with (E)-3-arylidene-4-flavanone, (E)-3- arylidene-4-chromanone and (E)-2-arylidene-1-tetralone as dipolarophiles has been investigated. High degree of regioselectivity has been obsd. in the synthesis of a new class of functionalized dispiroheterocyclic compd. contg. dispiro pyrroloisoquinoline and acenaphthequinone framework.

Abstract

Synthesis of dispiro[flavanone/chromanone/tetralone]-pyrrolo[1,2-a]isoquinolinespiro[3.2'']acenaphthen-1''-one systems through three component 1,3-dipolar cycloaddition reaction. Jayashankaran, Jayadevan; Manian, Rathna Durga R. S.; Raghunathan, Raghavachary. Laboratoire de Chimie Moleculaire et Thioorganique (LCMT) UMR CNRS 6507, Ensicaen et Universite de Caen Basse Normandie, Caen, Fr. Letters in Organic Chemistry (2006), 3(12), 917-921. Publisher: Bentham Science Publishers Ltd., CODEN: LOCEC7 ISSN: 1570-1786. Journal written in English. CAN 148:33601 AN 2007:123306 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


that of total carotenoid. Hesperidin was the major flavanone, which abounded in Liucheng and Tonkan (5.36 ± 0.145 and 4.13 ± 0.050 mg/g db, resp.). Naringin abounded in Peiyou and Wendun (1250 ± 0.82 and 2205 ± 11.1 μg/g db, resp.). Diosmin was the major flavone, and Kumquat (0.699 ± 0.021 mg/g db) and Lemon (0.323 ± 0.004 mg/g db) had the highest contents. Kaempferol was the most abundant flavanol except in Wendun, Peiyou, and Kumquat, and Murcott had the highest content (1.04 ± 0.007 mg/g db). Chlorogenic acid was the major phenolic acid, and Wendun and Lemon had the highest contents (103 ± 11.5 and 92.6 ± 8.90 μg/g db, resp.). β-Cryptoxanthin was the main carotenoid (0.764 ± 0.031-6.67 ± 0.329 μg/g db), followed by β-carotene (0.435 ± 0.016-3.77 ± 0.154 μg/g db), and these 2 compds. abounded in Murcott. Tonkan, Wendun, Peiyou, and Lemon had high levels of ascorbic acid. Total pectin levels ranged from 40.4 ± 1.65 to 87.3 ± 3.69 mg/g db.


flavanone


The mechanism of total flavanone from Alpinia Officinarum Rhizoma (AOR) exts. on the ileum myoelec. activity of rabbits in vitro was studied. The samples of isolated ileum segment were prepd., the contraction intensity were measured. Effects of AOR exts. on the contraction induced by BaCl2, histamine and actions on 2-component contraction evoked by ACh in the rabbit ileum were studied. Results showed that AOR exts. could significantly inhibit spontaneous constriction of ileum, exert an inhibitory effect on the contraction induced by BaCl2, histamine. It also inhibited the inflow of intracellular Ca2+ induced by ACh. It was concluded that AOR exts. could restrain the contraction on the rabbit ileum, this effect could be related to Ca2+ channel, M-receptor, H-receptor and direct action.

Abstract

The effects of total flavanones from alpinia officinarum Rhizoma extracts on the activity of isolated ileum muscle in rabbits. Tang, Chunping; Jiang, Tao; Chen, Shaoyi; Chen, Yanfen; Yang, Chaoyan. Research Institute of Chinese Mater. Med. Pharmacol., Guangdong College of Pharmacy, Guangzhou, Peop. Rep. China. Zhongyao Yaoli Yu Linchuang (2006), 22(5), 23-25. Publisher: Zhongyao Yaoli Yu Linchuang Bianjibu, CODEN: ZYYLBL ISSN: 1001-859X. Journal written in Chinese. CAN 146:415023 AN 2007:94034 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A semi-preparative reversed phase liq. chromatog. (RPLC) was used to isolate the chem. constituents from the chloroform ext. of Patrinia villosa Juss. The sepn. condition was optimized as follows: the column was YWG C18 (10.0 mm × 200 mm i.d., 10 μm), the mobile phase was composed of CH3CN-H2O-HAC (55:45:2, V/V) at a flow rate of 4.0 mL/min, the detection wavelength and sample size were set at 280 nm and 750 μL (30 g/L). Under the optimized conditions, five compds. were isolated by RPLC in one run. Their chem. structures were identified as bolusanthol B (1); (2S)-5,7,2',6'-tetrahydroxy-6-lavandulylated flavanone (2); (2S)-5,2',6'-trihydroxy-2",2"-dimethylpyrano[5",6":6,7]flavanone (3); orotinin (4) and orotinin-5-Me ether (5) by spectroscopic methods including UV, IR, electrospray mass spectrometry, one-dimensional NMR and two-dimensional NMR techniques. Among them, compds. 2 and 3 were new compds., and compds. 1, 4 and 5 were isolated from the P. genius for the first time.

Abstract

Isolation and purification of prenylated flavonoids from Patrinia villosa Juss by reversed phase preparative liquid chromatography. Peng, Jinyong; Fan, Guorong; Wu, Yutian; Chen, Hongyuan. Shanghai Key Laboratory for Drug Metabolism, College of Pharmacy, The Second Military Medical University, Shanghai, Peop. Rep. China. Fenxi Huaxue (2006), 34(7), 983-986. Publisher: Kexue Chubanshe, CODEN: FHHHDT ISSN: 0253-3820. Journal written in Chinese. CAN 146:149251 AN 2007:103242 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Studies were carried out on the leaves of Cassia alata. A new flavanone 5,7,4'-trihydroxy flavanone was isolated from the leaves of Cassia alata with the help of column and thin layer chromatog. using a gradient of org. solvents with increasing polarity. The compd. was characterized on the basis of UV, IR, 1H-NMR and Mass spectrometry.

Abstract


flavanone

A new flavanone and a new flavanone glycoside from Scutellaria baicalensis. Yin, Jun Gang. Department of Applied Bibliographic Information Answer 304:

The present invention relates to implantable medical devices, such as stents, that comprise a compn. for controlled delivery of flavonoids or a deriv. thereof. The flavonoids are aimed at preventing or reducing secondary complications which can occur following implantation of the device such as e.g. occlusive and catastrophic vascular phenomena. The invention further relates to the inclusion of addnl. therapeutic agents in the system that may have antiproliferative, antimitotic, antimicrobial, anticoagulant, fibrinolytic, anti-inflammatory, immunosupressive, and anti-angiogenic activities. The compn. comprising the flavonoids and optional further therapeutic agents may be used in methods for treating or preventing narrowing or obstruction of a body passageway. In particular the devices and compns. of the invention are useful in methods for treating or preventing restenosis, e.g. subsequent to angioplasty and/or for preventing or reducing acute, subacute and chronic secondary complications assocd. with angioplasty, such as e.g. thrombus. For example, a stent made from 316L was coated with paclitaxel and genistein dissolved in polymers solns. of poly(L-lactide), poly(glycolide-lactide) and polyvinyl pyrrolidone with dichloromethane as the solvent.

Abstract WO 2006-IB1848 W 20060626US 2005-699509P P 20050715EP 2005-106528 A 20050715Priority Application GB 2443576 A 20080507 GB 2008-1525 20060626 CA 2617728 A1 20070125 CA 2006-2617728 20060626



WO 2007010342 A1 20070125 WO 2006-IB1848 20060626Patent No. Kind Date Application No. Date Patent Family Information

Implantable medical devices comprising flavonoids' coating for prevention of restenosis. Managoli, Nandkishore. (Sahajanand Biotech Private Limited, India). PCT Int. Appl. (2007), 30pp. CODEN: PIXXD2 WO 2007010342 A1 20070125 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-IB1848 20060626. Priority: EP 2005-106528 20050715; US 2005-699509 20050715. CAN 146:190620 AN 2007:87257 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Patent No. Kind Date Application No. Date Patent Family Information

Compositions for treating or preventing obesity, insulin resistance and mitochondrial-associated disorders. Milburn, Michael; Milne, Jill; Auwerx, Johan; Argmann, Carmen; Lagouge, Marie; Dipp, Michelle. (Sirtris Pharmaceuticals, Inc., USA). PCT Int. Appl. (2007), 337pp. CODEN: PIXXD2 WO 2007008548 A2 20070118 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US26272 20060707. Priority: US 2005-697443 20050707; US 2005-736528 20051114; US 2005-753606 20051223; US 2006-783802 20060316. CAN 146:169320 AN 2007:61185 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chromatog. behavior of polyphenols (flavonoids and phenolic acids) was studied by reversed-phase thin-layer chromatog. (RP-TLC) to establish relations between chromatog. data and selected ADME (absorption, distribution, metab., and elimination) data. Good correlation between chromatog. RM values (a measure of the interactions of the solute with the lipophilic stationary phase and with the hydrophilic mobile phase) and the concn. of the buffer in the mobile phase (r ≥ 0.994) might be taken as a measure of the suitability of the system for estn. of the lipophilicity of the polyphenols. Exptl. obtained RMw values (a measure of the interactions of the solute with the lipophilic stationary phase and with pure water as mobile phase) and ϕ0 (the vol. fraction of org. modifier/buffer in the mobile phase for which retention is zero) were compared with ADME data calcd. by software packages based on different theor. approaches. From the authors' results the authors could establish correlations between chromatog. behavior and lipophilicity, soly., plasma-protein binding, and oral absorption of the polyphenols studied.

Abstract

ADME data for polyphenols characterized by reversed-phase thin-layer chromatography. Mornar, Ana; Medic-Saric, Marica; Jasprica, Ivona. Department of Medicinal Chemistry, University of Zagreb, Zagreb, Croatia. Journal of Planar Chromatography--Modern TLC (2006), 19(112), 409-417. Publisher: Research Institute for Medicinal Plants, CODEN: JPCTE5 ISSN: 0933-4173. Journal written in English. CAN 147:419280 AN 2007:67019 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new flavanone (2S)-5,7,2',5'-tetrahydroxyflavanone (1) together with a new flavanone glycoside (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-β-D-glucopyranoside (2), were isolated from the dry roots of S. baicalensis. Their structures were elucidated on the basis of spectroscopic data.

Abstract

Chemistry, Yantai University, Yantai, Peop. Rep. China. Chinese Chemical Letters (2006), 17(11), 1457-1459. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 146:354687 AN 2007:69112 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Intake of flavonoids has been inversely related to the risk of various common neoplasms, but limited data exist on renal cell carcinoma (RCC). We used data from a case-control study conducted between 1994 and 2002 in four Italian areas to study the relation between major flavonoid classes and RCC. The study included 767 cases with incident, histol. confirmed RCC and 1,534

Abstract

Flavonoids and the Risk of Renal Cell Carcinoma. Bosetti, Cristina; Rossi, Marta; McLaughlin, Joseph K.; Negri, Eva; Talamini, Renato; Lagiou, Pagona; Montella, Maurizio; Ramazzotti, Valerio; Franceschi, Silvia; LaVecchia, Carlo. Istituto di Ricerche Farmacologiche "Mario Negri", Universita degli Studi di Milano, Milan, Italy. Cancer Epidemiology, Biomarkers & Prevention (2007), 16(1), 98-101. Publisher: American Association for Cancer Research, CODEN: CEBPE4 ISSN: 1055-9965. Journal written in English. CAN 146:401106 AN 2007:46517 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Provided herein are methods and compns. for treating or preventing metabolic disorders, such as obesity and diabetes. Methods may comprise modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell with a sirtuin activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin, or an inhibitory compd., such as nicotinamide. Resveratrol increases the PGC-1 protein deacetylation.

Abstract WO 2006-US26272 W 20060707US 2006-783802P P 20060316US 2005-753606P P 20051223US 2005-736528P P 20051114US 2005-697443P P 20050707Priority Application


EP 1898897 A2 20080319 EP 2006-786429 20060707CA 2613141 A1 20070118 CA 2006-2613141 20060707AU 2006269459 A1 20070118 AU 2006-269459 20060707US 20070149466 A1 20070628 US 2006-374295 20060316



WO 2007008548 A3 20070809WO 2007008548 A2 20070118 WO 2006-US26272 20060707


flavanone

Mandarin juices from 3 pure clementine (Citrus clementina Hort. ex Tan.) cultivars: Clemenules, Hernandine and Marisol, 3 clementine-hybrids: Nova (clementine×tangelo Orlando), Ortanique (clementine×orange) and Fortune (clementine×mandarin Dancy) and one satsuma (Citrus unshiu Marc) cultivar: Clauselline were analyzed for simultaneous detn. of their flavanone-7-O-glycosides (FGs)

Abstract

Differentiation of juices from clementine (Citrus clementina), clementine-hybrids and satsuma (Citrus unshiu) cultivars by statistical multivariate discriminant analysis of their flavanone-7-O-glycosides and fully methoxylated flavones content as determined by liquid chromatography. Sentandreu, E.; Izquierdo, L.; Sendra, J. M. Instituto de Agroquimica y Tecnologia de Alimentos, Burjassot, Spain. European Food Research and Technology (2007), 224(4), 421-429. Publisher: Springer GmbH, CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 146:357444 AN 2007:41444 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The kinetic of the O2(1Δg)-photosensitized oxidn. of the flavanone naringin (7-rhamnoglucosyl-4',5-dihydroxyflavanone, FL) and its chalcone isomer (4'-rhamnoglucosyl-2',6',4-trihydroxychalcone, CH) in neutral and 1 mM NaOH ethanol solns. was studied using Rose Bengal as photosensitizer. The rate consts. for the chem. quenching of O2(1Δg) by the flavonoids (kr) were detd. using either UV-vis absorption spectroscopy or HPLC techniques, and for the total (phys. + chem.) quenching (k t) were detd. using time-resolved phosphorescence detection of O2(1Δg) at 1270 nm. A larger reactivity towards O2(1Δg) of CH than for FL in neutral ethanol solns. was obsd., due to the extra conjugated double bond in CH. However, in alk. media the reactivity of both isomers was larger than in neutral conditions. This behavior was assocd. to the increment of electron d. by the formation of a carbanion in FL and to the presence of the extended conjugated π-system in the CH isomer by deprotonation of phenolic groups. In all cases, the formation of 4-hydroxybenzoic acid as ending product was detected by HPLC. Based on reported mechanisms of O2(1Δg)-mediated oxidn. of flavonoids, the formation of 7-rhamnoglucosyl-5,4'-dihydroxyflavonol as primary photo-oxidn. product was proposed. The reactivity towards O2(1Δg) of the aglycon of naringin (5,7,4'-trihydroxyflavanone or naringenin, NG) in alk. conditions was lower than for the parent naringin, due to incapability of NG to form a carbanion species. These results are expected to have significance in biosynthesis, antioxidant properties and stability of naturally occurring flavonoids.

Abstract

Kinetic study of the photosensitized oxygenation of the flavanone naringin and its chalcone. Montenegro, Mariana A.; Nazareno, Monica A.; Borsarelli, Claudio D. Instituto de Ciencias Quimicas, Facultad de Agronomia y Agroindustrias, Universidad Nacional de Santiago del Estero, Santiago del Estero, Argent. Journal of Photochemistry and Photobiology, A: Chemistry (2007), 186(1), 47-56. Publisher: Elsevier B.V., CODEN: JPPCEJ ISSN: 1010-6030. Journal written in English. CAN 147:448986 AN 2007:43687 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


hospital controls admitted for acute, nonneoplastic conditions and matched with cases by study center, sex, and quinquennia of age. We applied published data on food and beverage content of six major classes of flavonoids to dietary information collected through a validated food frequency questionnaire. After adjustment for major recognized confounding factors and total energy intake, the odds ratios for subjects in the highest vs. the lowest quintile of intake were 0.80 [95% confidence interval (95% CI), 0.58-1.11] for total flavonoids, 0.76 (95% CI, 0.56-1.03) for isoflavones, 0.94 (95% CI, 0.60-1.47) for anthocyanidins, 0.77 (95% CI, 0.56-1.06) for flavan-3-ols, 0.90 (95% CI, 0.67-1.21) for flavanones, 0.68 (95% CI, 0.50-0.93) for flavones, and 0.69 (95% CI, 0.50-0.95) for flavonols. Allowance for vegetable and fruit consumption only partly explained these inverse relations. Thus, flavonoids, and particularly flavones and flavonols, may account, at least in part, for the favorable role of plant foods on RCC.


flavanone

Anti-inflammatory agents containing natural products from Angelica keiskei. Akihisa, Toshihiro; Yasukawa, Tadashi; Ukiya, Motohiko; Hasegawa, Daisuke. (Nihon University, Japan). Jpn. Kokai Tokkyo Koho (2007), 14pp. CODEN: JKXXAF JP 2007001898 A 20070111 Patent written in Japanese. Application: JP 2005-182196 20050622. Priority: . CAN 146:148815 AN 2007:30992 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytochem. anal. of twigs and roots of Erythrina abyssinica, a traditionally used medicinal plant, gave a new radical scavenging flavanone, 7,3',4'-trihydroxy-5'-prenylflavanone (abyssinone VII; 1), along with 21 known compds., whose radical scavenging and antimicrobial activities were also assessed.

Abstract

Radical scavenging-flavonoids from Erythrina abyssinica. Machumi, Francis; Bojase-Moleta, Gomotsang; Mapitse, Renameditswe; Masesane, Ishmael; Majinda, Runner R. T. Department of Chemistry, University of Botswana, Gaborone, Botswana. Natural Product Communications (2006), 1(4), 287-292. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN 147:48600 AN 2007:34673 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new flavanone glycoside, butin 4'-O-(2''-O-β-D-apiofuranosyl)-β-D-glucopyranoside (1), together with liquiritin (2), liquiritin apioside (3), isoliquiritin apioside (4), davidioside (5), quercetin (6), kaempferol (7), kaempferol 3-O-β-D-glucopyranoside (8) and kaempferol 3-O-α-L-arabinofuranoside (9) were isolated from the marc of R. damascena flowers after industrial distn. of essential oil. This is the 1st report of the occurrence of compds. 2, 3, 4 and 5 in R. damascena. The structures of the isolated constituents were established on the basis of spectroscopic {UV, IR, 1D, 2D NMR (DEPT, HMQC, HMBC and COSY)}, spectrometric (ESI-QTOF-MS), and chem. evidence.

Abstract

Flavonoids from Rosa damascena Mill. Kumar, Neeraj; Singh, Bikram; Kaul, Vijay K. Natural Plant Products Division, Institute of Himalayan Bioresource Technology, Palampur, India. Natural Product Communications (2006), 1(8), 623-626. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN 146:334108 AN 2007:34697 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


and fully methoxylated flavones (FMFs) content, using HPLC. Statistical multivariate discriminant anal. from the FGs concn. data showed that its discriminant power was rather poor, leading to overlapping between some groups of the assayed cultivars. By contrast, the discriminant power from the FMFs concn. data was very high and only two concn. ratios were needed as discriminant parameters to significantly differentiate between all the assayed cultivars. Moreover, the values of the discriminant parameters were almost independent of the location of the orchards and the maturity stage of the fruits.


flavanone

Abstract

New insight into the ring contraction of 2'-benzyloxyflavanones. Nemeth, Istvan; Gulacsi, Katalin; Antus, Sandor; Keki, Sandor; Zsuga, Miklos. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. Natural Product Communications (2006), 1(11), 991-996. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN 148:100405 AN 2007:29144 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OH

OOH

ROO O

O

Me

OH O O

O

1R e

e

M

M

R6

R5

eM

OR 10R9

8R

R7

I

IVIII

II

Title agents contain chalcones I [R = OH, OMe; R1 = prenyl, geranyl, CH2CH(OH)CMe:CH2, CH2CH2CMe(OH)CH2CH2CH:CMe2; R1 and the adjacent OH may be linked to form 6-membered substituted ring], coumarins II (R6 = H, OH, O2CCMe:CHMe, O2CCH:CMe2), coumarin deriv. III , and/or flavanones IV (R7 = H, OH, OMe; R8 = OH, OMe; R9 prenyl, geranyl; R10 = H, geranyl) as active ingredients. Thus, 13 compds. isolated from A. keiskei inhibited TPA-induced edema in mouse ears. The ID50 value of 4-hydroxyderricin was 68 μg/ear, vs. 300 μg/ear, for indomethacin.



flavanone

CA 2611878 A1 20070111 CA 2006-2611878 20060619AU 2006266287 A1 20070111 AU 2006-266287 20060619US 20070004796 A1 20070104 US 2005-169860 20050629Patent No. Kind Date Application No. Date Patent Family Information

Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4b,8)-epicatechin or -catechin dimers and their digallates. Romanczyk, Leo; Sharma, Pradeep K.; Kolchinski, Alexander G.; Shea, Helene A.; Gou, Yanni. (USA). U.S. Pat. Appl. Publ. (2007), 9pp. CODEN: USXXCO US 2007004796 A1 20070104 Patent written in English. Application: US 2005-169860 20050629. Priority: . CAN 146:121750 AN 2007:17789 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The 13C NMR resonances corresponding to the C-Me group of C(6) and/or C(8) C-methylated-flavonoids absorb between 6.7-10.0 ppm and typically between 6.7-8.7 ppm. A comparative 13C NMR study reflects that the 13C NMR chem. shifts reported for 6-hydroxy-5-methyl-3',4',5'-trimethoxyaurone-4-O-α-L-rhamnoside from Pterocarpus santalinus and C(8)-methyl-5,7,2',4'-tetramethoxyflavanone from Terminalia alata are inconsistent with the assigned structures, and therefore need reconsideration.

Abstract

Carbon-13 NMR chemical shift of methyl group: a useful parameter for structural analysis of C-methylated flavonoids. Agrawal, Pawan K.; Agrawal, Chandan; Agrawal, Shravan. Natural Product Inc., Westerville, OH, USA. Natural Product Communications (2006), 1(11), 957-959. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN 148:78783 AN 2007:29138 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OCH 2PhR

1R

I

The reactions of 2'-benzyloxyflavanones I (RR1 = OCH2O; R = OMe, R1 = H) with thallium(III) nitrate or iodobenzene diacetate in the presence of perchloric or sulfuric acid in tri-Me orthoformate was studied. Depending on the substitution pattern and the conditions, these compds. underwent 2-aryl migration and/or ring contraction and dehydrogenation. A probable mechanism of these transformations is discussed.


flavanone

Production of soybean isoflavone genistein in non-legume plants via genetically modified secondary metabolism pathway. Liu, Rongrong; Hu, Yuanlei; Li, Jialin; Lin, Zhongping. National Laboratory of Protein Engineering and Plant Genetic Engineering, Peking University, Beijing, Peop. Rep. China. Metabolic Engineering (2007), 9(1), 1-7. Publisher: Elsevier B.V., CODEN: MEENFM ISSN: 1096-7176. Journal written in English. CAN 146:291720 AN 2007:12422 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH

OH

OH

HO

OH

O

OH

OH

OH

HO

OHI II

Improved processes for the prepn. of tetra-O-benzyl protected catechin (I), for the coupling of the tetra-O-benzyl protected catechin or epicatechin (II) with a C-4 activated, tetra-O-benzyl protected epicatechin for the galloylation of the epicatechin-(4β,8)-catechin or -epicatechin dimer-the dimer digallates, and for the deprotection (i.e., debenzylation) of the protected epicatechin dimers and protected epicatechin dimer digallates are disclosed.

Abstract WO 2006-US23698 W 20060619US 2005-169860 A 20050629Priority Application


EP 1896444 A2 20080312 EP 2006-773470 20060619


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RS, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW

WO 2007005248 A3 20070726WO 2007005248 A2 20070111 WO 2006-US23698 20060619


flavanone

Abstract

Biodiversity conservation and drug discovery in madagascar, part 22: cytotoxic compounds of Physena madagascariensis from the Madagascar rain forest. Cao, Shugeng; Norris, Andrew; Miller, James S.; Ratovoson, Fidy; Birkinshaw, Chris; Andriantsiferana, Rabodo; Rasamison, Vincent E.; Rakotonandrasana, Stephan; Kingston, David G. I. Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA. Natural Product Research, Part A: Structure and Synthesis (2006), 20(13), 1157-1163. Publisher: Taylor & Francis Ltd., CODEN: NPRPC8 Journal written in English. CAN 146:478745 AN 2007:730 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Topical formulations are disclosed that contain aromatase P 450 and/or estrogen receptor blockers (particularly tamoxifen) for treatment or prevention of wrinkles. Active agents are present at 0.1-5.0%.

Abstract BR 2004-668 20040220Priority Application BR 2004000668 A 20051011 BR 2004-668 20040220 Patent No. Kind Date Application No. Date Patent Family Information

Topical aromatase inhibitors and estradiol receptor blockers for treatment of wrinkles. Okigami, Henry; Okigami, Paulo Takao. (Brazil). Braz. Pedido PI (2005), 10pp. CODEN: BPXXDX BR 2004000668 A 20051011 Patent written in Portuguese. Application: BR 2004-668 20040220. Priority: . CAN 146:49750 AN 2007:3240 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Genetic modification of secondary metabolic pathways to produce desirable natural products is an attractive approach in plant biotechnol. In our study, we attempted to produce a typical soybean isoflavone genistein, a well-known health-promoting metabolite, in non-legume plants via genetic engineering. Both overexpression and antisense suppression strategies were used to manipulate the expression of several genes encoding key enzymes in the flavonoids/isoflavonoids pathway in transgenic tobacco, lettuce, and petunia. Introducing soybean isoflavone synthase (IFS) into these plants, which naturally do not produce isoflavonoids due to a lack of this leguminous enzyme, resulted in genistein biosynthesis in tobacco petals, petunia leaves and petals, and lettuce leaves. In tobacco, when flavanone 3-hydroxylase (F3H) expression was suppressed by its antisense gene while soybean IFS was overexpressed at the same time, genistein yield increased prominently. In addn., overexpression of phenylalanine ammonia-lyase (PAL) also led to an enhanced genistein prodn. in tobacco petals and lettuce leaves in the presence of IFS than in the plants that overexpressed only IFS.

Abstract


flavanone

Chem. investigation of the leaves of Tephrosia apollinea has yielded a new flavanone named (+)-apollineanin, together with 2 known flavones: (-)-semiglabrin and (-)-semiglabrinol. The structure of the new compd. was detd. on the basis of mass, 1D and 2D NMR spectroscopies including NOE difference spectroscopy. The abs. stereochem. of (+)-apollineanin was detd. by Mosher ester methodol. and from CD data.

Abstract

(+)-Apollineanin: a new flavanone from Tephrosia apollinea. Hisham, A.; John, Shaly; Al-Shuaily, Wafa; Asai, Teigo; Fujimoto, Yoshinori. Department of Chemistry, College of Science, Sultan Qaboos University, Al-Khode, Oman. Natural Product Research, Part A: Structure and Synthesis (2006), 20(12), 1046-1052. Publisher: Taylor & Francis Ltd., CODEN: NPRPC8 Journal written in English. CAN 146:478744 AN 2006:1359352 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A comprehensive study of the complex polyphenol biosynthesis in developing leaves of apple (Malus domestica) was performed comprising gene expression, enzyme activities and polyphenol compn. During leaf development, an early increase in gene expression was obsd. for phenylalanine ammonia lyase (PAL, EC 4.3.1.5), chalcone synthase (CHS, EC 2.3.1.74), flavanone 3-hydroxylase (FHT, EC 1.14.11.9) and dihydroflavonol 4-reductase/flavanone 4-reductase (DFR/FNR, EC 1.1.1.219). Their enzyme activities showed a corresponding trend during the time course. A parallel set of expts. was carried out with leaves treated with prohexadione-Ca (ProCa), which is an enzyme inhibitor of 2-oxoglutarate dependent dioxygenases (2-ODDs). ProCa is known to induce changes in polyphenol biosynthesis, which are accompanied by a reduced incidence of fire blight and scab, the two major pome fruit diseases. The application of ProCa led to an increase in activities of PAL, CHS, FHT and DFR/FNR, which was based on an enhanced gene expression. In contrast, an inhibition of gene expression was detected for anthocyanidin synthase (EC 1.14.11.19). These effects are interpreted as a feedback regulation by changed polyphenol levels. Because of the inhibition of the 2-ODDs FHT and flavonol synthase (EC 1.14.11.23), some pronounced changes in polyphenol compn. were obsd. Eriodictyol, the substrate of FHT, accumulated as eriodictyol-7-O-glucoside and 6''-O-trans-p-coumaroyleriodictyol 3'-O-glucoside. In addn., the 3-deoxycatechin luteoliflavan was formed which is not present in untreated apple leaves. Hence, beyond the redirection of polyphenol biosynthesis by the enzyme inhibitor, changed polyphenol levels obviously cause a distinct induction of gene expression by feedback regulation.

Abstract

Induction of polyphenol gene expression in apple (Malus × domestica) after the application of a dioxygenase inhibitor. Fischer, Thilo C.; Halbwirth, Heidrun; Roemmelt, Susanne; Sabatini, Emidio; Schlangen, Karin; Andreotti, Carlo; Spinelli, Francesco; Costa, Guglielmo; Forkmann, Gert; Treutter, Dieter; Stich, Karl. Lehrstuhl fuer Zierpflanzenbau, Department fuer Pflanzenwissenschaften, Technische Universitaet Muenchen Weihenstephan, Freising, Germany. Physiologia Plantarum (2006), 128(4), 604-617. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 147:296182 AN 2007:362 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new flavanones, remangiflavanones D and E (1 and 2), were isolated from an ext. of the twigs, leaves, and flowers of Physena madagascariensis together with 3 known flavanones, remangiflavanones A-C (3-5), and (E)-N-feruloyltyramine (6). The structures of the new compds. 1 and 2 were established on the basis of one-dimensional and two-dimensional NMR spectroscopic data interpretation. All compds. were evaluated for their cytotoxicity in the A2780 human ovarian cancer cell line. Compd. 5 was the most active with an IC50 value of 2.5 μg mL-1.


flavanone

Structural characterization for flavonoids through MEDV and xanthine-oxidase inhibition activity prediction by QSAR. Zhang, Meng-Jun; Wu, Shi-Rong; Liao, Chun-Yang; Li, Zhi-Liang. Dep. Analytical Chem., Fac. Clinical Lab. Sci., The Third Miliary Medical Univ., Chongqing, Peop. Rep. China. Jiefangjun Yaoxue Xuebao (2006), 22(5), 328-332. Publisher: Zhongguo Renmin Jiefangjun Zonghouqinbu Weishengbu Yaopin Yiqi Jianyansuo, CODEN: JYXIAY ISSN: 1008-9926. Journal written in Chinese. CAN 147:203008 AN 2006:1336367 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chalcones and their analogs were extd. from the twigs of Dorstenia barteri and investigated for their capacity to inhibit matrix metalloproteinase (MMP)-2 secretion from brain tumor-derived U87 glioblastoma cells. Among all tested compds., potent inhibitory activities were recorded for chalcones 1, 4, 5, and 6 and to a lesser extent for 2 and 3. Semi-synthetic derivs. 7-9 displayed low (<30%) MMP-2 secretion inhibitory activity at concns. ranging from 0.025 to 250 μM. Chalcones 1, 4, 5, and 6 were found to be more active in comparison to the documented MMP secretion inhibitors chlorogenic acid (CHL) and epigallocatechin-3-gallate (EGCg). Hydrogenation of 1 and acid-catalyzed cyclization of 3 were performed, thus generating three semi-synthetic derivs. (7-9). The newly synthesized flavanone 7 (cycloglabrol) and its chalcone analog 8 (isocycloglabrol) exhibited low MMP-2 secretion inhibitory activity with 30% inhibition at 250 μM. The activity of Dorstenia barteri crude exts. could be attributable to the high concn. of prenylated chalcones and more specifically to stipulin 5. Altogether, the structure-activity relationships established indicated that the hydroxyl, 2,3-double bond, the prenyl group, and its positioning could account for their role in inhibiting MMP-2 secretion, a process involved in extracellular matrix degrdn. and brain tumor progression.

Abstract

Inhibition of matrix metalloproteinase-2 secretion by chalcones from the twigs of Dorstenia barteri Bureau. Ngameni, Bathelemy; Touaibia, Mohamed; Belkaid, Anissa; Ambassa, Pantaleon; Watchueng, Jean; Patnam, Ramesh; Ngadjui, Bonaventure T.; Annabi, Borhane; Roy, Rene. Department of Chemistry, Universite du Quebec a Montreal, Montreal, QC, Can. ARKIVOC (Gainesville, FL, United States) (2007), (9), 91-103. Publisher: Arkat USA Inc., CODEN: AGFUAR http://www.arkat-usa.org/ARKIVOC/JOURNAL_CONTENT/manuscripts/2007/BA-2092LP%20as%20published%20mainmanuscript.pdf Journal; Online Computer File written in English. CAN 146:74866 AN 2006:1345336 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The first synthesis of (±)-monotesone B and new syntheses of (±)-lonchocarpol A and (±)-bavachin were achieved starting from the corresponding methoxymethyl-protected C-prenylated acetophenone derivs. Their antifungal activity was tested against Candida albicans.

Abstract

First synthesis of (±)-monotesone B and new syntheses of (±)-lonchocarpol A and (±)-bavachin. Kenez, Agnes; Antus, Sandor. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. Natural Product Communications (2006), 1(1), 51-55. Publisher: Natural Product Communications, CODEN: NPCACO ISSN: 1555-9475. Journal written in English. CAN 147:469151 AN 2006:1359270 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

2-Hydroxy-3-nitro-5-methylacetophenone condenses with 3,4-substituted benzaldehydes in EtOH in presence of aq. NaOH to give chalcones. Subsequent heating under reflux with 80% ethanol and concd. H2SO4 gave flavanones I (R = H, R1 = NO2; RR1 = OCH2O; R = R1 = H; R = OMe, R1 = H), while reaction with N2H4.H2O in EtOH led to the resp. pyrazolines II. The latter are also

Abstract

Synthesis of some nitro-substituted flavanones, pyrazolines, and their derivatives. Parmar, P. J.; Rajput, S. I.; Doshi, A. G. Department of Chemistry, B.P. Arts, S.M.A. Science and K.K.C. Commerce College, Chalisgaon, India. Asian Journal of Chemistry (2007), 19(1), 493-498. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in English. CAN 147:448688 AN 2006:1313466 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This paper reports the effects of heat treatment on huyou (Citrus paradisi Changshanhuyou) peel in terms of phenolic compds. and antioxidant capacity. High-performance liq. chromatog. (HPLC) coupled with a photodiode array (PDA) detector was used in this study for the anal. of phenolic acids (divided into 4 fractions: free, ester, glycoside, and ester-bound) and flavanone glycosides (FGs) in huyou peel (HP) before and after heat treatment. The results showed that after heat treatment, the free fraction of phenolic acids increased, whereas ester, glycoside, and ester-bound fractions decreased and the content of total FGs declined (P < 0.05). Furthermore, the antioxidant activity of methanol ext. of HP increased (P < 0.05), which was evaluated by total phenolics contents (TPC) assay, 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS.bul.+) method, and ferric reducing antioxidant power (FRAP) assay. The correlation coeffs. among TPC, ABTS, FRAP assay, and total cinnamics and benzoics (TCB) in the free fraction were significantly high (P < 0.05), which meant that the increase of total antioxidant capacity (TAC) of HP ext. was due at least in part to the increase of TCB in free fraction. In addn., FGs may be destroyed when heated at higher temp. for a long time (for example, 120 °C for 90 min or 150 °C for 30 min). Therefore, it is suggested that a proper and reasonable heat treatment could be used to enhance the antioxidant capacity of citrus peel.

Abstract

Effect of Heat Treatment on the Phenolic Compounds and Antioxidant Capacity of Citrus Peel Extract. Xu, Guihua; Ye, Xingqian; Chen, Jianchu; Liu, Donghong. Department of Food Science and Nutrition, Zhejiang University, Hangzhou, Peop. Rep. China. Journal of Agricultural and Food Chemistry (2007), 55(2), 330-335. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 146:80740 AN 2006:1328958 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The aim of this paper is to predict xanthine-oxidase inhibition activity of flavonoids. A novel set of structural descriptors with ten elements, called the mol. electronegativity-distance vector(MEDV), was developed according to classification of four connection formula for various local carbon and pseudo-carbon atoms in the mols. under examn. The MEDV-d vector was then used to describe the chem. structures of 21 flavonoids by a multiple linear regression(MLR). The performance of the six-parameter model was tested through cross-validation by the leave-one-out procedure(LOO). A reasonable mol. modeling result was achieved with a very high correlation coeff. (r=0.925) and a satisfactory result of cross-validation was obtained with a fairly resemble correlation coeff. (r=0.843). The model based on the MEDV descriptors showed good estimative stability and predictive ability, and could be used for designing and developing efficient inhibitors of xanthine-oxidase.

Abstract


flavanone


This study aimed to investigate the potential for flavonoid action at A1 adenosine receptors in vitro. In a radioligand binding assay for A1 adenosine receptor occupancy in particulate prepns. from guinea-pig cerebral cortex, flavonoids competed in concn.-dependent manners with Hill slopes typically not different from unity. Of the flavonoids tested, quercetin showed highest affinity (pKi value of 5.33). At a concn. of 28 μM, quercetin evoked a rightward shift in the N6-cyclopentyladenosine-induced inhibition of elec. evoked contractions of the guinea-pig isolated ileum, allowing the calcn. of a pKi value of 4.71. These data suggest, therefore, that flavonoids represent an addnl. dietary source of A1 adenosine receptor antagonists (beyond the methylxanthines, caffeine and theophylline).

Abstract

Flavonoids as antagonists at A1 adenosine receptors. Alexander, Stephen P. H. Institute of Neuroscience and School of Biomedical Sciences, University of Nottingham Medical School, Nottingham, UK. Phytotherapy Research (2006), 20(11), 1009-1012. Publisher: John Wiley & Sons Ltd., CODEN: PHYREH ISSN: 0951-418X. Journal written in English. CAN 146:198589 AN 2006:1312755 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

NO 2

Me

O

OH

O2N

Me

N NH

R1

R

R1

R

I

II

obtained by treatment of I with N2H4.H2O, piperidine, and EtOH under reflux. Pyrazolines II reacted with AcOH to form 1-acetylpyrazolines. Pyrazolines II or the 1-acetyl derivs. reacted with Ac2O and a pinch of anhyd. NaOAc to give 1-acetyl-2-acetoxypyrazolines. Condensation of II with BzCl in pyridine yields 1-benzoylpyrazolines. The structures of all compds. were established on the basis of spectral data (UV, IR, NMR), elemental anal., and chem. properties.


flavanone

Exotic flora dependence of an unusual Brazilian propolis: The pinocembrin biomarker by capillary techniques. Adelmann, Juliana; Passos, Mauricio; Breyer, Daniel Henrique; Rocha dos Santos, Maria Helena; Lenz, Cesar; Leite, Natalicio Ferreira; Lancas, Fernando Mauro; Fontana, Jose Domingos. Biomass Chemo/Biotechnology Laboratory (LQBB), Department of Pharmacy, R. Lothario Meissner, Federal University of Parana (UFPR), Subsede Botanico, Curitiba PR, Brazil. Journal of Pharmaceutical and Biomedical Analysis (2007), 43(1), 174-178. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 146:148565 AN 2006:1298616 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavones chem. are anthoxanthins, occur either in the free state or as glycosides assocd. with tannins (Flavanoids). Flavanoids (derivs. of flavone) possess various pharmacol. activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivs. (flavanone derivs.) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram pos. and gram-neg. bacteria. IR, NMR and CHN anal. confirmed the structure of the synthesized compds. The results of the antibacterial studies shows that compds. 2b, 2e, 2f and 2h possess activity against many bacterial strains. Among that the compd. (2h) has remarkable activity against all strains viz. 25 μg/mL inhibitory concn. against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compd. 2f possess min. inhibitory concn. of 200 μg/mL against E. coli and S. typhimurium and 25 μg/mL against S. sonnei, S. dysenteriae and V. cholerae. In silico metabolic and toxicity study of the synthesized compds. were performed and the predicted result showed that the compd. having hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivs. undergo demethylation reaction. The biol. active compds. are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.

Abstract

Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanone derivatives. Moorthy, Narayana Subbiah Hari Narayana; Singh, Rahul Jitendra; Singh, Hemendra Pratap; Gupta, Sayan Dutta. School of Pharmaceutical Sciences, Rajiv Gandhi Proudyogiki Vishwavidyalaya, Bhopal, India. Chemical & Pharmaceutical Bulletin (2006), 54(10), 1384-1390. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 146:176177 AN 2006:1300811 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Among the naturally occurring citrus flavonoids, hesperidin, a flavanone glycoside, may be assocd. with potential benefits in the prevention of diseases, such as decreasing capillary permeability, anti inflammatory, antimicrobial and anti carcinogenic effects. Hesperidin also regulates hepatic cholesterol synthesis by inhibiting the activity of 3-hydroxy-3-methylglutaryl CoA (HMG-CoA) reductase. Recently, Mundy et al. reported that statins, cholesterol lowering agents, induce bone formation and inhibit bone resorption both in vitro and in vivo. Thus, considerable attention has focused on the relationship between the inhibitory activity on HMG-CoA reductase and bone action. We examd. the effects of hesperidin on bone metab. in ovariectomized mice, orhiectomized mice and magnesium deficient rats, animal models of osteoporosis. Hesperidin inhibited bone loss the animals with lowering serum and hepatic cholesterol. These results suggest hesperidin may act on bone by the same mechanism as that of statins. Further studies are needed to define hesperidin's mechanisms of action on bone.

Abstract

Hesperidin and bone metabolism. Uehara, Mariko. Faculty of Applied Bio-Science, Department of Nutritional Science, Tokyo University of Agriculture, Japan. Clinical Calcium (2006), 16(10), 1669-1676. Publisher: Iyaku Janarusha, CODEN: CLCCEJ ISSN: 0917-5857. Journal written in Japanese. CAN 146:378942 AN 2006:1307537 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The invention relates to a method for prevention and treatment of aging, age-related disorders and/or age-related manifestations including atherosclerosis, peripheral vascular disease, coronary artery disease, osteoporosis, type 2 diabetes, dementia, and some forms of arthritis and cancer in a subject comprising administration sep., sequentially, or simultaneously of a therapeutically effective dosage of each component or combination of statins, bisphosphonates, cholesterol-lowering agents, or biol. or biochem. inhibitors targeting the interleukin-6 signaling pathway. Inhibition of the signal transduction pathway for interleukin 6-mediated inflammation is key to the prevention and treatment of atherosclerosis, peripheral vascular disease, coronary artery disease, aging, age-related disorders and/or age-related manifestations including osteoporosis, type 2 diabetes, dementia and some forms of arthritis and tumors.

Abstract US 2005-268609 A2 20051108US 2005-122030 A2 20050505US 2005-58371 A2 20050216US 2004-961037 A2 20041012US 2002-224743 B2 20020822Priority Application US 20060078533 A1 20060413 US 2005-268609 20051108 US 20060078532 A1 20060413 US 2005-122030 20050505US 20050152905 A1 20050714 US 2005-58371 20050216US 20060078531 A1 20060413 US 2004-961037 20041012US 20040038874 A1 20040226 US 2002-224743 20020822US 20060275294 A1 20061207 US 2006-279239 20060410Patent No. Kind Date Application No. Date Patent Family Information

Prevention and treatment of aging and age-related disorders. Omoigui, Osemwota Sota. (USA). U.S. Pat. Appl. Publ. (2006), 60pp., Cont.-in-part of U.S. Ser. No. 268,609. CODEN: USXXCO US 2006275294 A1 20061207 Patent written in English. Application: US 2006-279239 20060410. Priority: US 2002-224743 20020822; US 2004-961037 20041012; US 2005-58371 20050216; US 2005-122030 20050505; US 2005-268609 20051108. CAN 146:20347 AN 2006:1286190 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Significant amts. of pinocembrin (>10%), a dihydroxy-flavanone, was found in the compn. of an unusual brand of a subtropical Brazilian propolis. Incidentally, this sealing material was obtained from hives surrounding a large forestry site based on a single exotic flora, namely poplar (Populus sp.). Examn. of the different botanical parts of poplar revealed the buds as the main source of the flavanone. Techniques used for the establishment of the chem. correlation between the propolis brand and the poplar buds were TLC/densitometry, capillary GC-MS in the e.i. mode, and capillary zone electrophoresis with DAD monitoring. Since color enhancement after Al3+ complexation applies just for more hydroxylated flavonoids, the alternative techniques herein applied were of value for pinocembrin detection and estn. Anal. data indicated the dominance of the main phenolic pinocembrin biomarker as well as the presence of other related flavonoids in the botanical source and in the propolis derived thereof.

Abstract


flavanone

Dehydrogenation of flavanones, 1H-3-(2-hydroxy-3-nitro-5-methylphenyl)-5-(substituted phenyl)-2-pyrazolines and their derivatives. Parmar, P. J.; Rajput, S. I. Department of Chemistry, B. P. Arts, S.M.A. Science and K.K.C. Commerce College,


Cellulite in women can be treated with a compn. contg. an aromatase inhibitor and an estrogen receptor blocker encapsulated in nanocapsules, liposomes, or in cyclodextrin.

Abstract BR 2003-3724 20030821Priority Application BR 2003003724 A 20050412 BR 2003-3724 20030821 Patent No. Kind Date Application No. Date Patent Family Information

Cosmetic method for treating gynoid lipodystrophy. Okigami, Henry; Guerra Filho, Samuel dos Santos; Lacerda, Jorge Renato Guimaraes. (Brazil). Braz. Pedido PI (2005), 23pp. CODEN: BPXXDX BR 2003003724 A 20050412 Patent written in Portuguese. Application: BR 2003-3724 20030821. Priority: . CAN 145:495713 AN 2006:1266854 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Topics discussed are development mechanism of pollen allergy and antiallergic effect of mandarin orange, effect of mandarin orange powder on histamine release inhibition in pollen allergic patients, effect of mandarin orange powder on inhibition of RBL-2H3 cell degranulation, mechanism of flavanone in mandarin orange on inhibition of cell degranulation and inhibitory components in mandarin orange.

Abstract

Antiallergic action of mandarin orange. Kobayashi, Shoko; Takayanagi, Masayoshi; Tanabe, Shoichi. Dep. of Health and Welfare, Takasaki Univ. of Health and Welfare, Japan. New Food Industry (2006), 48(11), 15-22. Publisher: Shokuhin Shizai Kenkyukai, CODEN: NYFIAM ISSN: 0547-0277. Journal; General Review written in Japanese. CAN 147:94707 AN 2006:1279460 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Said method for prevention and treatment of said disorders is based on inhibition of interleukin-6 inflammation through regulation of cholesterol metab., isoprenoid depletion and/or inhibition of the signal transduction pathway.


flavanone

A chemotaxonomic study carried out for the leaves of Trembleya laniflora (D. Don) Cogn. (Melastomataceae) resulted in the Abstract

A flavanone and other constituents of the Brazilian endemic species Trembleya laniflora (D. Don) Cogn. (Melastomataceae). Ventura, Claiton Pires; Dias de Souza Filho, Jose; Braga de Oliveira, Alaide; Braga, Fernao Castro. Faculdade de Farmacia, Universidade Federal de Minas Gerais, Belo Horizonte, Pampulha, Brazil. Biochemical Systematics and Ecology (2006), Volume Date 2007, 35(1), 40-41. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 146:247454 AN 2006:1239648 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

R I

Microwave enhanced diversity-oriented synthesis (MEDOS) using palladium catalyzed protocols was introduced as a powerful new strategy for the synthesis of systematically modified small mols. and was highlighted by application to functionalized flavones. E.g., brominated flavone I (R = Br) was reacted with phenylboronic acid using POPd and CsF in THF at 85° under microwave irradn. to give the corresponding arylation product I (R = Ph) with 98% yield.

Abstract

Microwave enhanced palladium catalyzed coupling reactions: A diversity-oriented synthesis approach to functionalized flavones. Fitzmaurice, Richard J.; Etheridge, Zac C.; Jumel, Emelie; Woolfson, Derek N.; Caddick, Stephen. Department of Chemistry, Christopher Ingold Laboratories, University College London, London, UK. Chemical Communications (Cambridge, United Kingdom) (2006), (46), 4814-4816. Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in English. CAN 146:162936 AN 2006:1245874 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Pyrazolines or flavanones were treated with I in DMSO to give 1H-3-(2-hydroxy-3-nitro-5-methylphenyl)-5-arylpyrazoles or 6-methyl-8-nitroflavones.

Abstract

Chalisgaon, India. International Journal of Chemical Sciences (2006), 4(3), 629-634. Publisher: Sadguru Publications, CODEN: IJCSIL ISSN: 0972-768X. Journal written in English. CAN 147:406736 AN 2006:1255634 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

US 2002-126407 A2 20020418Priority Application US 7329687 B2 20080212US 20040029914 A1 20040212 US 2003-418736 20030418US 20030229136 A1 20031211 US 2002-126407 20020418US 20060264500 A1 20061123 US 2006-404230 20060414Patent No. Kind Date Application No. Date Patent Family Information

Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents. Zaveri, Nurulain; Waleh, Nahid. (Sri International, USA). U.S. Pat. Appl. Publ. (2006), 37pp., Cont.-in-part of U.S. Ser. No. 418,736. CODEN: USXXCO US 2006264500 A1 20061123 Patent written in English. Application: US 2006-404230 20060414. Priority: US 2002-126407 20020418; US 2003-418736 20030418. CAN 145:505256 AN 2006:1228593 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids can be beneficial for human health via antioxidant and anti-inflammatory mechanisms. We investigated whether and by what mechanisms dietary flavonoids inhibit expression of cellular adhesion mols., which is relevant to inflammation and atherosclerosis. The capacity of flavonoids to inhibit tumor necrosis factor α-induced adhesion mol. expression in human aortic endothelial cells in vitro was dependent on specific structural features of the flavonoids. The 5,7-dihydroxyl substitution of a flavonoid A ring and 2,3-double bond and 4-keto group of the C ring were the main structural requirements for inhibition of adhesion mol. expression. Hydroxyl substitutions of the B and C rings but not the A ring, were essential for antioxidant activities. Thus, only hydroxyl flavones, such as apigenin and chrysin, and flavonols, such as galangin, kaempferol and quercetin, were able to inhibit endothelial adhesion mol. expression, whereas flavone, chromone, the flavanone naringenin, and the flavanol (-)-epicatechin, were not effective. At low concns., the active flavonoids attenuated the expression of E-selectin and intercellular adhesion mol. 1 (ICAM-1), but not vascular cell adhesion mol. 1 (VCAM-1). Exposure of cultured hepatocytes to apigenin and kaempferol mimicked the first pass metab. and greatly diminished the inhibitory effect of flavonoids on endothelial ICAM-1 expression. Thus, the effects of dietary flavonoids on endothelial adhesion mol. expression depend on their mol. structure, concn., and metabolic transformation, but not their antioxidant activity.

Abstract

Dietary flavonoids attenuate tumor necrosis factor α-induced adhesion molecule expression in human aortic endothelial cells. Structure-function relationships and activity after first pass metabolism. Lotito, Silvina B.; Frei, Balz. Linus Pauling Institute, Oregon State University, Corvallis, OR, USA. Journal of Biological Chemistry (2006), 281(48), 37102-37110. Publisher: American Society for Biochemistry and Molecular Biology, CODEN: JBCHA3 ISSN: 0021-9258. Journal written in English. CAN 146:44816 AN 2006:1236511 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


identification of 5-hydroxy-7,4'-dimethoxyflavone, along with mixts. of α-amirin (major constituent), β-amirin and lupeol; β-sitosterol (84%) and stigmasterol (16%). The isolated compds. were evaluated in the antimicrobial agar diffusion assay and none of them inhibited the growth of Staphylococcus aureus and Micrococcus luteus in the concn. of 50 μg/disk.


flavanone

Flower fragrance is a composite character detd. by secondary metabolites of diverse biosynthetic origin. Together with other traits, such as flower color, it is used by plants to lure pollinators and seed dispersers, thus ensuring plant survival. Research into the regulatory mechanisms leading to floral scent prodn./emission is still in its infancy and even less is known regarding flow within and crosstalk between secondary metabolic pathways leading to floral scent prodn. Using transgenic plants modified in anthocyanin prodn., we revealed an intriguing interrelationship between the branches of the phenylpropanoid pathway leading to the prodn. of anthocyanins and volatiles. Specifically, we recorded five- to seven-fold higher levels of the volatile phenylpropanoids Me benzoate and 2-hydroxy-Me benzoate in flavanone 3-hydroxylase (F3h)-suppressed carnation flowers with dramatically reduced anthocyanin levels, as compared to control non-transgenic flowers. Furthermore, over-expression in petunia flowers of the transcriptional regulator Pap1 (prodn. of anthocyanin pigment 1), which activates the phenylpropanoid pathway, led to increases in both anthocyanin accumulation and volatile phenylpropanoid emission. Using virus-induced gene silencing (VIGS) for large-scale identification of floral scent genes, we further characterized metabolic flow within the pathway. The advantages of VIGS and of petunia as a model plant create a solid infrastructure for the future isolation of regulatory factors involved in floral scent prodn./emission. Knowledge gained

Abstract

Navigating the network of floral scent production. Zvi, M. Moyal Ben; Spitzer, B.; Vainstein, A. The Institute of Plant Sciences and Genetics in Agriculture, Faculty of Agricultural, Food and Environmental Quality Sciences, The Hebrew University of Jerusalem, Rehovot, Israel. Acta Horticulturae (2006), 714(Proceedings of the XXIInd International Eucarpia Symposium, Section Ornamentals, 2006), 143-154. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 147:207745 AN 2006:1219276 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH

OMe

OMe

OMeX

R5

8

R9R2

R1

R3

7

R6

R

R

a

bI II

Flavanoids, flavanones and flavanols, such as I [R1, R2, R3 = H, OH, sulfhydryl, halogen alkoxy, etc.; R5 = O, S, :NH, OH, SH, NH2, acyloxy, etc.; R6, R7, R8, R9 = H, OH, alkoxy, etc. or neighboring groups may form fused carbocyclic rings, such as R6R7 = -CH:CHCH:CH- or R7R8 = -(CH2)4-; X = O, S, NH, CH2; bonds a and b may be double or single as appropriate for substituents], and related chalcones were prepd. for use in pharmaceutical compns. as chemotherapeutic, chemopreventive, and antiangiogenic agents. These flavanoids and chalcones were claimed for therapeutic use in the treatment of cancer of the brain, breast, ovary, prostate, lung, kidney or colon. Thus, flavanol II was prepd. via a cyclocondensation reaction of 1-hydroxy-2-acetonaphthone with 3,4,5-trimethoxybenzaldehyde using piperidine and pyridine in EtOH to form the corresponding flavanone and subsequent redn. of the resulting flavanone using NaBH4 in THF/EtOH. Pharmaceutical compns. were provided, as well as, methods of synthesis and use.

Abstract US 2003-418736 A2 20030418


flavanone

Isolation and characterization of antioxidant components from oregano (Origanum heracleoticum). Tsimogiannis, Dimitrios; Stavrakaki, Maria; Oreopoulou, Vassiliki. School of Chemical Engineering, National Technical University of Athens, Athens,


In order to make use of the resources of peanut hulls, avoid wasting and approach the extn. of total flavanone of peanut hulls. The flavonids were extd. by ethanol as the solvent from peanut hulls with ultrasonic wave and ethanol extn. Using spectrophotometry to ext. and check the flavanone of peanut hulls. By this method getting the d. of the total flavanone of peanut hulls is C = 0.5937mg/mL and the rate of recovery is 101.1 %. This text provides the extn. and purifying methods to get the outcome and the purity of the flavanone are all very high. This method is a purely phys. process and has not any pollution. It is an ideal way to ext. the flavanone of peanut hulls.

Abstract

The total flavanones of peanut hulls extraction and the identification by ultrasonic wave. Yang, Wen-hui; Li, Wei-bin; Huang, Suo-yi; Li, Rong. Youjiang Med. College for Nationalities, Baise, Guangxi, Peop. Rep. China. Weiliang Yuansu Yu Jiankang Yanjiu (2006), 23(5), 28-30. Publisher: Weiliang Yuansu Yu Jiankang Yanjiu Zazhishe, CODEN: WYYJAF ISSN: 1005-5320. Journal written in Chinese. CAN 146:480996 AN 2006:1191648 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The methanolic exts. from branches (BEP) and leaves (LEP) of Eysenhardtia platycarpa significantly decreased the blood glucose levels in normal and streptozotocin (STZ)-induced diabetic rats. One new flavone, (1''R)-5,4',1''-trihydroxy-6,7-(3'',3''-dimethylchroman)flavone (1), together with the known compds. 5,7-dihydroxy-6-methyl-8-prenylflavanone (3), 5,7-dihydroxy-8-methyl-6-prenylflavanone (4), 5,7-dihydroxy-6-prenylflavanone (5), 5,7-dihydroxy-8-prenylflavanone (6), 3-O-acetyloleanolic acid (7), oleanolic acid, 3β-acetoxy-11α,12α-epoxy-oleanan-28,13β-olide, lupeol, betulinic acid, β-sitosterol, β-sitosteryl β-D-glucopyranoside, β-sitosteryl palmitate, and 3-O-methyl-myo-inositol were isolated from BEP. Addnl., one new flavanone, (2S)-4'-O-methyl-6-methyl-8-prenylnaringenin (2), as well as the known compds. 3,4,6,4'-O-methyl-8-prenylnaringenin (8), and 5-hydroxy-7-methoxy-8-prenylflavanone (9) were isolated from LEP. 3-O-Acetyloleanolic acid (7), identified as the major constituent of BEP, showed a significant decrease (31 mg/kg of body wt., P < 0.05) in the glucose level of STZ-induced diabetic rats. The obtained results correlate with the traditional use of this species.

Abstract

Antihyperglycemic Activity and Chemical Constituents of Eysenhardtia platycarpa. Narvaez-Mastache, Jose M.; Garduno-Ramirez, Maria Luisa; Alvarez, Laura; Delgado, Guillermo. Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Coyoacan, Mex. Journal of Natural Products (2006), 69(12), 1687-1691. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 146:118105 AN 2006:1212282 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


from an understanding of mechanisms leading to floral scent prodn./emission should provide us with better insight into nature's way of ensuring evolutionary success, as well as with advanced tools for the metabolic engineering of fragrance.


flavanone

Acetylated Flavanone Glycosides from the Rhizomes of Cyclosorus acuminatus. Fang, Wei; Ruan, Jinlan; Wang, Zhong; Zhao, Zhongxiang; Zou, Jian; Zhou, Daonian; Cai, Yaling. College of Pharmacy, Tongji Medical Center, Huazhong University of Science and Technology, Wuhan, Peop. Rep. China. Journal of Natural Products (2006), 69(11), 1641-1644. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 146:96799 AN 2006:1142994 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention pertains to a polysaccharide formulation purified from Juglans mandshurica for treating cerebral cancer, which comprises Juglans mandshurica polysaccharide 85-98% and flavonoids e.g. flavone, flavonol, flavanone, flavanol 15-2%. The formulation 0.1-200g is dissolved in water or 0.1-20% ethanol soln. for oral administration. Method for extg. antitumor ingredients comprises pulvering, extg. with water twice, filtering, concg. the supernatant, extg. with chloroform, pptg. the aq. phase with ethanol, drying and pulverizing to obtain Juglans mandshurica polysaccharide powder for use.


Polysaccharide formulation from Juglans mandshurica for treating cerebral cancer. Miao, Zhiqi; Yu, Xiangli; Wang, Yechun; Miao, Haibin; Tang, Kexuan. (Shanghai Jiao Tong University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 11pp. CODEN: CNXXEV CN 1850102 A 20061025 Patent written in Chinese. Application: CN 1002-4276 20060302. Priority: . CAN 145:511573 AN 2006:1150648 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In this study, Origanum heracleoticum was examd. as potential source of phenolic antioxidants. The components of the plant were extd. in a Soxhlet app. sequentially with solvents of increasing polarity, specifically with petroleum ether (P), di-Et ether (D) and ethanol (E); the ethanol ext. was further fractionated to obtain a di-Et ether (ED) and an Et acetate (EEAc) fraction. The activity of the exts. to scavenge 2'2'-diphenyl-1-picrylhydrazyl followed the order ED > E> D > EEAc > > P. Moreover, the antioxidant activity in refined cottonseed oil at a concn. of 500 ppm was monitored through peroxide value measurements and revealed that ED resulted in the highest decrease in the rate of peroxide formation followed by D. Specific flavonoids and rosmarinic acid were detected as the main components of D, ED through HPLC-DAD and HPLC-MS/MS analyses.

Abstract

Greece. International Journal of Food Science and Technology (2006), 41(Suppl. 1), 39-48. Publisher: Blackwell Publishing Ltd., CODEN: IJFTEZ ISSN: 0950-5423. Journal written in English. CAN 146:141367 AN 2006:1159345 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 346:

Flavanones, the main polyphenols of citrus fruits, are thought to contribute to the protective effects of these fruits against cardiovascular diseases and cancer. The metab. of naringin (naringenin 7-O-neohesperidoside) is studied here in healthy (sham-operated, ShO) and tumor-bearing (TuB) rats. The tumor was induced by implanting Yoshida's sarcoma in hindlimb. Both groups received for 7 days a semi-synthetic diet contg. 0.5% naringin in per feeding conditions. Flavanones were analyzed in plasma, liver, kidney and urine by tandem mass spectrometry. Naringenin conjugates (essentially glucuronides) accounted for up to 98% of the total flavanones in plasma. Low amts. of hesperetin (4'-O-Me naringenine) and isosakuranetin (3'-hydroxy-4'-O-methylnaringenin) were also detected in all biol. samples and accounted for 2% of the total flavanones in plasma. They were largely present as aglycons. The in vivo hydroxylation of flavanones is described here for the first time. Total concns. of naringenin metabolites reached 17.3 ± 2.7 μM in plasma 6 h after the beginning of the meal in healthy rats and only 10.6 ± 1.3 μM in TuB rats. The nature of metabolites was similar in both healthy and TuB rats and in plasma, tissues and urine. The lower concn. of flavanones in the TuB rats suggests that disease and more particularly cancer, may affect the bioavailability of flavonoids.

Abstract

Flavanone metabolism in healthy and tumor-bearing rats. Silberberg, M.; Gil-Izquierdo, A.; Combaret, L.; Remesy, C.; Scalbert, A.; Morand, C. Unite des Maladies Metaboliques et Micronutriments, Inra, Centre de Recherche de Clermont-Ferrant/Theix, Saint-Gene` s-Champanelle, Fr. Biomedicine & Pharmacotherapy (2006), 60(9), 529-535. Publisher: Elsevier SAS, CODEN: BIPHEX ISSN: 0753-3322. Journal written in English. CAN 147:202969 AN 2006:1138113 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The rate consts. and activation energy barriers ΔG.thermod. of diastereomerization reaction of flavanones: naringin, narirutin, hesperidin and neohesperidin were detd. The stopped-flow HPLC (SFM-HPLC), dynamic HPLC (D-HPLC) and enantioselective HPLC combined with the classical kinetic method were applied for detn. of these parameters. It was found that the rate consts. of diastereomerization were about eight times higher for naringin and narirutin (1.9 × 10-5 s-1) than for hesperidin and neohesperidin (2.4 × 10-6 s-1). No significant differences in the rate of diastereomerization were found between neohesperidosides and corresponding rutinosides.

Abstract

Determination of diastereomerization barrier of some flavanones by high-performance liquid chromatography methods. Asztemborska, Monika; Zukowski, Janusz. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, Pol. Journal of Chromatography, A (2006), 1134(1-2), 95-100. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 146:100195 AN 2006:1140031 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Six new flavanone glycosides (1-6) were isolated from the methanol ext. of the rhizomes of C. acuminatus, together with the parent flavanone glycoside. Their structures were established on the basis of spectroscopic and chem. methods. All compds. showed moderate activity against Streptococcus pneumoniae and Haemophilus influenzae.

Abstract


flavanone

A compn. for the prevention and treatment of cancer comprising a 2',4',5,7-tetrahydroxy-5',6-diprenylflavanone compd. is provided to inhibit casein kinase 2, thereby being able to inhibit propagation of tumor cells. The compn. for the prevention and treatment of cancer

Abstract KR 2004-94403 A3 20041118Priority Application KR 773133 B1 20071102KR 2007083237 A 20070823 KR 2007-81393 20070813KR 2006055083 A 20060523 KR 2004-94403 20041118Patent No. Kind Date Application No. Date Patent Family Information

Composition for prevention and treatment of cancer comprising 2',4',5,7-tetrahydroxy-5',6-diprenylflavanone compound for preventing propagation of tumor cells by inhibiting casein kinase 2(ckii). Bae, Young Seuk; Kim, Soon Hee; Lee, Byong Won; Park, Ki Hun. (Industry-Academic Coorperation Foundation Daegu Haany University, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2006), No pp. given. CODEN: KRXXA7 KR 2006055083 A 20060523 Patent written in Korean. Application: KR 2004-94403 20041118. Priority: . CAN 145:460543 AN 2006:1133160 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The title method comprises extg. Patrinia villosa with ethanol to obtain crude ext., grade-extg. the crude ext. with org. solvent, and purifying with silica gel column chromatog. to obtain the final product. The obtained product has high purity over 99%, and can be prepd. in large scale. The product has antitumor activity, and can be applied to prepn. of antitumor agents.


Extraction method and its application of (2S)-5,7,2',6'-tetrahydroxy-6,8-di(γ, γ-dimethylallyl)-flavanone. Fan, Guorong; Peng, Jinyong; Chai, Yifeng; Wu, Yutian. (Second Military Medical University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 11pp. CODEN: CNXXEV CN 1850816 A 20061025 Patent written in Chinese. Application: CN 1002-6825 20060524. Priority: . CAN 145:500049 AN 2006:1136719 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The new use of 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone in pharmaceutical. Zhu, Banghao; Liu, Deyu. (Sun Yat-Sen Bibliographic Information Answer 349:

Disclosed is an agent for inhibiting the transporter activity of an estrone-3-sulfate transporter, an agent for inhibiting the growth of breast cancer cells, or an agent for the treatment of breast cancer, which does not need to be incorporated in cells, has excellent drug delivery property and has few side effects. The agent comprises at least one component selected from genistein, quercetin, ginkgolide C, theaflavin, theaflavin 3-o-gallate, chalcone, rutin, daidzein, daidzin, flavanone, flavonol, geraldol, hesperetin, hespereridine, ipriflavone, luteolin-7-o-glucoside, methoxychalcone, 4'-methyl-7-methoxy-isoflavone, 5-morin, myricetin, naringenin, naringenin-7-glycoside, naringin, neohesperidin dihydrochalcone, nomilin, primuletin, poncirin, scutellarein, catechin hydrate, and chem. modified products thereof.

Abstract JP 2005-119098 A 20050415Priority Application JP 2006298781 A 20061102 JP 2005-119098 20050415


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Inhibitory agent for estrone-3-sulfate transporter activity. Tamai, Ikumi; Yabuuchi, Hikaru. (Genomembrane Co., Ltd., Japan). PCT Int. Appl. (2006), 30pp. CODEN: PIXXD2 WO 2006112330 A1 20061026 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2006-JP307751 20060412. Priority: JP 2005-119098 20050415. CAN 145:449189 AN 2006:1123248 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


comprises a 2',4',5,7-tetrahydroxy-5',6-diprenylflavanone or a pharmaceutically acceptable salt thereof, wherein the flavanone is extd. from the roots of Cudrania tricuspidata with a polar solvent including hexane, chloroform or Et acetate.


flavanone

Montamine, a unique dimeric indole alkaloid, from the seeds of Centaurea montana (Asteraceae), and its in vitro cytotoxic activity against the CaCo2 colon cancer cells. Shoeb, Mohammad; MacManus, Stephen M.; Jaspars, Marcel; Trevidu, Jioji;


Since the toxicol. effects of dioxins are mainly mediated by the aryl hydrocarbon receptor (AhR), an in vitro assessment system for AhR activity was used in this study to search for flavonoids that attenuated dioxin toxicity through the intestinal epithelial monolayer. When AhR transformation in Hepa-1c1c7 cells was examd. by southwestern ELISA, nine flavonoids among 34 kinds of flavonoids inhibited the transformation by more than one-half. When each flavonoid with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) was added to dioxin-responsive HepG2 cells, seven flavonoids significantly restrained the TCDD-induced transcriptional activity of the CYP1A1 promoter. Furthermore, those seven flavonoids that had permeated the Caco-2 cell monolayers demonstrated an inhibitory effect on both the AhR transformation and on the transcriptional activity of the CYP1A1 promoter. The expression level of the CYP1A1 mRNA and protein induced by TCDD was suppressed by flavone, galangin, and tangeretin. It is proposed from these results that some flavonoids have the ability to suppress dioxin-induced AhR activity after permeating the human intestinal epithelial cell monolayer.

Abstract

TCDD-Induced CYP1A1 Expression, an Index of Dioxin Toxicity, Is Suppressed by Flavonoids Permeating the Human Intestinal Caco-2 Cell Monolayers. Hamada, Mika; Satsu, Hideo; Natsume, Yayoi; Nishiumi, Shin; Fukuda, Itsuko; Ashida, Hitoshi; Shimizu, Makoto. Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, Yayoi, Bunkyo-ku, Japan. Journal of Agricultural and Food Chemistry (2006), 54(23), 8891-8898. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 146:56725 AN 2006:1110960 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The patent relates to new use of 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone to prep. inhibitor of saccharifying end product, antioxidant, inhibitor of diacylglycerol-protein kinase C. Said medicine is comprised of 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone and pharmaceutically acceptable adjuvant. The dose type may be injections, oral prepns., and targeting prepns. Said 3,5,7,3',4',5'-hexa-hydroxyl-2,3-flavanone is extd. from Vitis vinifera with alcs.


University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 13pp. CODEN: CNXXEV CN 1846695 A 20061018 Patent written in Chinese. Application: CN 1003-3775 20060221. Priority: . CAN 145:511418 AN 2006:1112871 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Development of DNA markers for identification of onion cultivars. Usui, Yuichi; Adachi, Shizuka; Kamiya, Motokazu; Nakashima, Toshiki; Yamamoto, Yoshihisa; Suzuki, Tadanao; Yasui, Akemi. Incorporated Administrative Agency Center for Food Quality, Labeling and Consumer Services, 2-1 Shintoshin, Chuuou-ku, Saitama City, Saitama, Japan. Nippon Shokuhin Kagaku Kogaku Kaishi (2006), 53(9), 498-504. Publisher: Nippon Shokuhin Kagaku Kogakkai, CODEN: NSKKEF ISSN: 1341-027X. Journal written in Japanese. CAN 146:398322 AN 2006:1107441 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Inhibition of protein tyrosine phosphatase-1B (PTP1B) has been proposed as a therapy for treatment of type-2 diabetes and obesity. Bioassay-guided fractionation of an EtOAc-sol. ext. of the root bark of Erythrina mildbraedii, using an in vitro PTP1B inhibitory assay, resulted in the isolation of three new isoprenylated flavonoids, abyssinone-IV-4'-O-Me ether (2), 7-hydroxy-4'-methoxy-3'-(3-hydroxy-3-methyl-trans-but-1-enyl)-5'-(3-methylbut-2-enyl)flavanone (3), and abyssinone-VI-4-O-Me ether (6), along with six known flavonoids, abyssinone-V-4'-O-Me ether (1), abyssinone-V (4), abyssinone-IV (5), sigmoidin E (7), 4'-hydroxy-5,7-dimethoxyisoflavone (8), and alpinumisoflavone (9). Compds. 1 and 2, 4-7, and 9 inhibited PTP1B activity, with IC50 values ranging from 14.8 ± 1.1 to 39.7 ± 2.5 μM. On the basis of the data obtained, flavanones and chalcones with isoprenyl groups may be considered as a new class of PTP1B inhibitors.

Abstract

Protein Tyrosine Phosphatase-1B Inhibitory Activity of Isoprenylated Flavonoids Isolated from Erythrina mildbraedii. Na, MinKyun; Jang, JunPil; Njamen, Dieudonne; Mbafor, Joseph Tanyi; Fomum, Zacharias Tanee; Kim, Bo Yeon; Oh, Won Keun; Ahn, Jong Seog. Korea Research Institute of Bioscience and Biotechnology (KRIBB), Daejeon, S. Korea. Journal of Natural Products (2006), 69(11), 1572-1576. Publisher: American Chemical Society-American Society of Pharmacognosy, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 146:41946 AN 2006:1108121 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Reversed-phase HPLC anal. of the methanol ext. of the seeds of Centaurea montana afforded a flavanone, montanoside (4), 6 epoxylignans, berchemol (7), berchemol 4'-O-β-D-glucoside (5), pinoresinol (10), pinoresinol 4-O-β-D-glucoside (8), pinoresinol 4,4'-di-O-β-D-glucoside (6), pinoresinol 4-O-apiose-(1→2)-β-D-glucoside (9), two quinic acid derivs., trans-3-O-p-coumaroylquinic acid (1), cis-3-O-p-coumaroylquinic acid (2), and 8 indole alkaloids, tryptamine (3), N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (11), cis-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (12), centcyamine (16), cis-centcyamine (17), moschamine (13), cis-moschamine (14) and a dimeric indole alkaloid, montamine (15). While the structures of 2 new compds., montanoside (4) and montamine (15), were established unequivocally by UV, IR, MS and a series of 1D and 2D NMR analyses, all known compds. were identified by comparison of their spectroscopic data with literature data. The antioxidant properties of these compds. were assessed by the DPPH assay, and their toxicity towards brine shrimps and cytotoxicity against CaCo-2 colon cancer cells were evaluated by the brine shrimp lethality and the MTT cytotoxicity assays, resp. The novel dimer, montamine (15), showed significant in vitro anticolon cancer activity (IC50 = 43.9 μM) while that of the monomer, moschamine (13), was of a moderate level (IC50 = 81.0 μM).

Abstract

Nahar, Lutfun; Kong-Thoo-Lin, Paul; Sarker, Satyajit D. Department of Chemistry, University of Dhaka, Dhaka, Bangladesh. Tetrahedron (2006), 62(48), 11172-11177. Publisher: Elsevier Ltd., CODEN: TETRAB ISSN: 0040-4020. Journal written in English. CAN 146:78002 AN 2006:1110691 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Salicin-based phenolic glycosides, hydroxycinnamate derivs. and flavonoid-derived condensed tannins comprise up to one-third of Populus leaf dry mass. Genes regulating the abundance and chem. diversity of these substances have not been comprehensively analyzed in tree species exhibiting this metabolically demanding level of phenolic metab. Here, shikimate-phenylpropanoid pathway genes thought to give rise to these phenolic products were annotated from the Populus genome, their expression assessed by semiquant. or quant. reverse transcription polymerase chain reaction (PCR), and metabolic evidence for function presented. Unlike Arabidopsis, Populus leaves accumulate an array of hydroxycinnamoyl-quinate esters, which is consistent with broadened function of the expanded hydroxycinnamoyl-CoA transferase gene family. Greater flavonoid pathway diversity is also represented, and flavonoid gene families are larger. Consistent with expanded pathway function, most of these genes were upregulated during wound-stimulated

Abstract

Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus. Tsai, Chung-Jui; Harding, Scott A.; Tschaplinski, Timothy J.; Lindroth, Richard L.; Yuan, Yinan. Biotechnology Research Center, School of Forest Resources and Environmental Science, Michigan Technological University, Houghton, MI, USA. New Phytologist (2006), 172(1), 47-62. Publisher: Blackwell Publishing Ltd., CODEN: NEPHAV ISSN: 0028-646X. Journal written in English. CAN 146:415997 AN 2006:1081081 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Nuclear factor-κB (NF-κB), a redox-sensitive transcription factor, plays an important role in the aging process. Thus, developing and identifying specific components that modulate NF-κB without adverse side-effects would be of major importance. Hesperetin, a flavanone abundant in citrus fruits, has a variety of pharmacol. properties being antioxidant, cholesterol-lowering, and anti-inflammatory. In this study, we investigated how hesperetin fed to 6- and 24-mo-old rats modulates NF-κB in their kidneys. Results showed that hesperetin suppressed NF-κB activation and related gene expressions. An even more interesting finding is that hesperetin suppressed NF-κB through four signal transduction pathways, NIK/IKK, ERK, p38, and JNK. Further evidence showed the remarkable efficacy of hesperetin to suppress the translocation of Trx/Ref-1, indicating its beneficial effect on the redox status. The most significant findings of the current study report new information on the use of hesperetin as a potential anti-aging agent.

Abstract

Modulation of the age-related nuclear factor-κB (NF-κB) pathway by hesperetin. Kim, Ji Young; Jung, Kyung Jin; Choi, Jae Sue; Chung, Hae Young. College of Pharmacy, Pusan National University, Pusan, S. Korea. Aging Cell (2006), 5(5), 401-411. Publisher: Blackwell Publishing Ltd., CODEN: ACGECQ ISSN: 1474-9718. Journal written in English. CAN 145:389298 AN 2006:1101334 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The possibility of identification of onion (Allium cepa L.) cultivars by DNA anal. was investigated. The genetic diversity of twenty onion cultivars from Japan, New Zealand, Australia, the USA and Thailand were examd., and 19 sets of sequence-tagged site (STS) primers were designed. Discriminating bands were amplified by each set of STS primers using DNA extd. from 24 onion bulbs of each cultivar. Individual variations in DNA bands in each cultivar were shown, which caused difficulties in discrimination between cultivars in the case of two sets of STS primers which were designed from cytoplasmic DNA (chloroplastic and mitochondrial DNA). However, some individual variations were shown in each cultivar by using the other seventeen sets of STS primers which were designed based on genomic DNA. These results suggested that the identification of onion cultivars using a single onion bulb is impossible. However, because it was shown that the population of allele frequency derived from each cultivar tended to be const., it may be possible to identify onion cultivars using a significance test to compare allele frequencies of two populations derived from multiple onion bulbs of two varieties.


flavanone

The medical compn. contains effective position or effective constituent extd. Sarcandra glabra which comprises flavones, and/or saponin, and/or polyoses such as isofraxidin-7-O-glucoside, 5,7-dihydroxy flavanone, 2',6'-dihydroxy-4'-methoxyl chalcone, pinostrobin, dihydromyricetin, pelargonidin, astilbin, naringenin-4',7-dimethyl ether. The purity of effective constituent is 50-99 %. The medical compn. comprises oral tablets, buccal tablets, chewing tablets; injections comprising small injections, large injections, powder injections, emulsions, suspensions, pills, dripping pills, capsules, soft capsules, granules, intumescent prepns., oral solns., syrups, mixts., sustained-release prepns., controlled-release prepns., and targeting prepns. The invention may be used in antitumor agents,


Medical composition containing flavones of Sarcandra glabra extract and its application. Lian, Xiaoyuan; Zhang, Zhizhen; Tang, Zulin. (Jiangxi Boshilian Science and Technology Research and Development Co., Ltd., Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 14pp. CODEN: CNXXEV CN 1839903 A 20061004 Patent written in Chinese. Application: CN 1004-9219 20060118. Priority: . CAN 145:477742 AN 2006:1069880 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


POMT-7, an O-methyltransferase from poplar (Populus deltoids) was used to modify a variety of flavonoid compds. POMT-7 was able to transfer a Me group to several flavonoids contg. a C-7 hydroxyl group. However, POMT-7 showed a higher affinity toward flavonol and flavone such as apigenin, kaempferol, luteolin, and quercetin than flavanone and isoflavone. Based on comparison of HPLC retention times with authentic compds. and corresponding NMR spectroscopy data, the methylation position of the reaction products was detd. to be at the hydroxyl group of C-7. Biotransformation kinetics indicated that the enzyme converted more than 80% of the apigenin, kaempferol, luteolin and quercetin substrates, which were added at concn. of 70 μM, into corresponding 7-methoxy compds. within 24 h.

Abstract

Regioselectivity of 7-O-methyltransferase of poplar to flavones. Kim, Bong-Gyu; Kim, Hojung; Hur, Hor-Gil; Lim, Yoongho; Ahn, Joong-Hoon. Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University, Seoul, S. Korea. Journal of Biotechnology (2006), 126(2), 241-247. Publisher: Elsevier B.V., CODEN: JBITD4 ISSN: 0168-1656. Journal written in English. CAN 146:141058 AN 2006:1078543 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


condensed tannin synthesis in leaves. The suite of Populus genes regulating phenylpropanoid product accumulation should have important application in managing phenolic carbon pools in relation to climate change and global carbon cycling.


flavanone

Plant genomes appear to exploit the process of gene duplication as a primary means of acquiring biochem. and developmental flexibility. The best example is the gene encoding chalcone synthase (CHS, EC2.3.1.74), the first committed step in flavonoid biosynthesis. In this study, we examd. the mol. evolution of three CHS family members of Phalaenopsis including a novel chs gene

Abstract

Molecular evolution and functional specialization of chalcone synthase superfamily from Phalaenopsis Orchid. Han, Ying-Ying; Ming, Feng; Wang, Wei; Wang, Jing-Wen; Ye, Ming-Ming; Shen, Da-Leng. Institute of Genetics, State Key Laboratory of Genetic Engineering, Research Centre of Gene Diversity and Designed Agriculture, Ministry of Education Key Laboratory for Biodiversity Science and Ecological Engineering, School of Life Science, Fudan University, Shanghai, Peop. Rep. China. Genetica (Dordrecht, Netherlands) (2006), 128(1-2-3), 429-438. Publisher: Springer, CODEN: GENEA3 ISSN: 0016-6707. Journal written in English. CAN 146:415986 AN 2006:1044785 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


An anti-inflammatory agent and an immuno-reaction inhibition agent comprising novel flavonoid are provided to inhibit transcriptional-promotion activity of RelA/p65, thereby inhibiting nuclear factor kappa B activity, generation of NO and secretion of TNF-α. The compd. is selected from the group consisting of 4'-demethyl eupatilin, cirsilineol, 5,6,4'-trihydroxy-7,3'-dimethoxyflavone, 8,4'-dihydroxy-3,7,2'-trimethoxyflavone, chrysoplenetin, and 5,8,4'-trihydroxy-flavanone. The method for isolating the compd. from Artemisia sylavatica comprises the steps of: (a) extg. stem of Artemisia sylavatica with water, alc., or a mixt. solvent thereof; (b) partitioning the ext. into a hexane layer and a water layer; (c) repeatedly extg. the water layer with ethylacetate; and (d) resp. purifying the hexane layer and the ethylacetate layer through repetitive chromatog.


Anti-inflammatory agent and immuno-reaction inhibition agent comprising flavonoid isolated from Artemisia sylvatica which inhibit expression of inflammation factor. Lee, Jung Joon; Lee, Jeong Hyung; Lee, Dong Ho; Hong, Young Soo. (Korea Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2006), No pp. given. CODEN: KRXXA7 KR 2006014534 A 20060216 Patent written in Korean. Application: KR 2004-63108 20040811. Priority: . CAN 145:403910 AN 2006:1057900 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


synergistic attenuation, toxic response of radiotherapy and chemotherapy. The injection can treat bleeding due to blood-heat, skin purple plague, primary thrombocytopenic purpura and secondary thrombocytopenic purpura, thrombocythemia, pharyngolaryngitis, tracheobronchitis, pulmonitis, keratitis, cellulitis, and appendicitis.


flavanone

Answer 362:

Two new lavandulylated flavanones, (2R,3R)-8-lavandulyl-2'-methoxy-5,7,4'-trihydroxyflavanonol (1) and 8-lavandulyl-5,7,4'-trihydroxyflavonol (2), were isolated from the dry roots of Sophara flavescens. Their structures were elucidated on the basis of spectroscopic data. Compds. 1 and 2 exhibited significant antibacterial activities.

Abstract

Two new antibacterial flavanones from Sophora flavescens. Cao, Mei Ai; Sun, Xiao Bai; Zhao, Pei Hua; Yuan, Cheng Shan. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Peop. Rep. China. Chinese Chemical Letters (2006), 17(8), 1048-1050. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 146:224748 AN 2006:992177 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present study evaluated antioxidant and neuroprotective activities of hesperidin, a flavanone mainly isolated from citrus fruits, and its aglycon hesperetin using cell-free bioassay system and primary cultured rat cortical cells. Both hesperidin and hesperetin exhibited similar patterns of 1,1-diphenyl-2-picrylhydrazyl radical scavenging activities. While hesperidin was inactive, hesperetin was found to be a potent antioxidant, inhibiting lipid peroxidn. initiated in rat brain homogenates by Fe2+ and L-ascorbic acid. In consistence with these findings, hesperetin protected primary cultured cortical cells against the oxidative neuronal damage induced by H2O2 or xanthine and xanthine oxidase. In addn., it was shown to attenuate the excitotoxic neuronal damage induced by excess glutamate in the cortical cultures. When the excitotoxicity was induced by the glutamate receptor subtype-selective ligands, only the N-methyl-D-aspartic acid-induced toxicity was selectively and markedly inhibited by hesperetin. Furthermore, hesperetin protected cultured cells against the Aβ25-35-induced neuronal damage. Hesperidin, however, exerted minimal or no protective effects on the neuronal damage tested in this study. Taken together, these results demonstrate potent antioxidant and neuroprotective effects of hesperetin, implying its potential role in protecting neurons against various types of insults assocd. with many neurodegenerative diseases.

Abstract

Antioxidant and neuroprotective effects of hesperidin and its aglycone hesperetin. Cho, Jungsook. Department of Pharmacology, College of Medicine, Dongguk University, Gyeongbuk, S. Korea. Archives of Pharmacal Research (2006), 29(8), 699-706. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 145:328235 AN 2006:1040738 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(phchs5), which is slowly evolved. The inferred phylogeny of the chs genes of Phalaenopsis with other two orchid plants, Bromoheadia finlaysoniana and Dendrobium hybrid, suggested that gene duplication and divergence have occurred before divergence of these three genera. Relatively quant. RT-PCR anal. identified expression patterns of these three chs genes in different floral tissues at different developmental stages. Phchs5 was the most abundantly expressed chs gene in floral organs and it was specifically transcribed in petal and lip at the stages when anthocyanin accumulated (stage 1-4). Phchs3 and phchs4 were expressed at much lower levels than phchs5. Phchs3 was expressed in pigmented tissue (including lip, petal and sepal) at middle stages (stages 2-4) and in colorless reproductive tissue at late stage (stage 5). Phchs4 was only expressed in petal at earlier stages (stage 1-3) and in lip at middle stage (stage 4). These results present new data on differentiation of gene expression among duplicate copies of chs genes in Phalaenopsis.


flavanone

Patent Family Information

Skin care compositions comprising hydrolyzed fucoidan. Mower, Thomas E. (USA). U.S. Pat. Appl. Publ. (2006), 15pp., Cont.-in-part of U.S. Ser. No. 83,826. CODEN: USXXCO US 2006210524 A1 20060921 Patent written in English. Application: US 2006-306997 20060118. Priority: US 2005-83826 20050318. CAN 145:362868 AN 2006:978988 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The fluorimetry was applied to det. the total flavanone quantity of hawthorn and hyperin was used as the comparison. The exptl. conditions were optimized as follows abs. alc. was used as solvent, the amts. of pure ethanolamine and surface active agent CTMAB (1.2 × 10-3 mol/L) was 0.5 mL and 0.6 mL, resp., the soln. was detd. under the room temp. At max. excitation wavelength of 457 nm and emission wavelength of 531 nm, the fluorescence intensity was measured. The detective limits is 2.4 × 10-7 mol/L in the linear range of 4 × 10-7 - 1.5 × 10-5 mol/L, RSD of the method is 1.64%. The method is simple, rapid, and accurate with a potential in anal. applications.

Abstract

Determination of total flavanone quantity hawthorn by micellar enhanced fluorimetry. Li, Man-Xiu; Bai, Bao-Lin; Zhang, Xiao-Li; Li, Hai-Ping. Department of Chemistry, Xinzhou Teachers University, Xinzhou, Shanxi, Peop. Rep. China. Guangpu Shiyanshi (2006), 23(4), 690-693. Publisher: Kexue Chubanshe, CODEN: GUSHEH ISSN: 1004-8138. Journal written in Chinese. CAN 146:480741 AN 2006:987627 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytoestrogens are plant-derived, non-steroidal constituents of our diets. They can act as agonists or antagonists of estrogen receptors, and they can modulate the activities of the key enzymes in estrogen biosynthesis. Much less is known about their actions on the androgen and progesterone metabolizing enzymes. We have examd. the inhibitory action of phytoestrogens on the key human progesterone-metabolizing enzyme, 20α-hydroxysteroid dehydrogenase (AKR1C1). This enzyme inactivates progesterone and the neuroactive 3α,5α-tetrahydroprogesterone, to form their less active counterparts, 20α-hydroxyprogesterone and 5α-pregnane-3α,20α-diol, resp. We overexpressed recombinant human AKR1C1 in Escherichia coli, purified it to homogeneity, and examd. the selected phytoestrogens as inhibitors of NADPH-dependent redn. of a common AKR substrate, 9,10-phenanthrenequinone, and progesterone. The most potent inhibitors were 7-hydroxyflavone, 3,7-dihydroxyflavone and flavanone naringenin with IC50 values in the low μM range. Docking of the flavones in the active site of AKR1C1 revealed their possible binding modes, in which they are sandwiched between the Leu308 and Trp227 of AKR1C1.

Abstract

Phytoestrogens as inhibitors of the human progesterone metabolizing enzyme AKR1C1. Brozic, Petra; Smuc, Tina; Gobec, Stanislav; Rizner, Tea Lanisnik. Institute of Biochemistry, Medical Faculty, University of Ljubljana, Ljubljana, Slovenia. Molecular and Cellular Endocrinology (2006), 259(1-2), 30-42. Publisher: Elsevier Ltd., CODEN: MCEND6 ISSN: 0303-7207. Journal written in English. CAN 145:432150 AN 2006:989932 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Naringenin is a naturally occurring flavanone, possessing a variety of biol. activity. Due to its rapid elimination, naringenin needs frequent administration to maintain an effective plasma concn. We have evaluated the therapeutic potential of naringenin-phospholipid complex under oxidative stress conditions compared with free naringenin. Naringenin-phospholipid complex was prepd. and assessed for antioxidant activity in carbon tetrachloride intoxicated rats at a dose level of 100 mg kg-1 (p.o.). Liver function tests were studied by assessing serum glutamate oxaloacetate transaminase, serum glutamate pyruvate transaminase, serum alk. phosphatase and total bilirubin. Marker enzymes of liver, namely glutathione peroxidase, superoxide dismutase, catalase and thiobarbituric acid reactive substances, were measured to evaluate the antioxidant potential at the same dose level. The plasma concn. of naringenin was also

Abstract

Enhanced therapeutic potential of naringenin-phospholipid complex in rats. Maiti, Kuntal; Mukherjee, Kakali; Gantait, Arunava; Saha, Bishnu Pada; Mukherjee, Pulok K. School of Natural Product Studies, Department of Pharmaceutical Technology, Faculty of Engineering and Technology, Jadavpur University, Kolkata, India. Journal of Pharmacy and Pharmacology (2006), 58(9), 1227-1233. Publisher: Pharmaceutical Press, CODEN: JPPMAB ISSN: 0022-3573. Journal written in English. CAN 145:341952 AN 2006:972203 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Skin care compns. for the care of wrinkles including partially hydrolyzed fucoidan, a base, and an anti-wrinkle compd. The partially hydrolyzed fucoidan may be sulfonated. The partially hydrolyzed fucoidan may be derived from Japanese mozuku seaweed, Japanese kombu seaweed, or Tongan limu moui seaweed. Also disclosed is a method of making the skin care compn.

Abstract US 2006-307032 A 20060119US 2006-307031 A 20060119US 2006-306997 A 20060118US 2006-306996 A 20060118US 2005-83826 A2 20050318Priority Application



WO 2007084721 A3 20080214WO 2007084721 A2 20070726 WO 2007-US1536 20070118US 20060210609 A1 20060921 US 2005-83826 20050318US 20060210524 A1 20060921 US 2006-306997 20060118Patent No. Kind Date Application No. Date


flavanone

Answer 368:

Monolithic capillary columns contg. native silica gel were covalently modified with 3,5-disubstituted phenylcarbamate derivs. of cellulose and amylose and applied for enantiosepns. in capillary LC. The method previously used for covalent immobilization of polysaccharide phenylcarbamate derivs. onto the surface of microparticulate silica gel was successfully adapted for in situ modification of monolithic fused-silica capillary columns. The effects of the nature of polysaccharide and the substituents, and of multiple covalent immobilization of polysaccharide deriv. on chromatog. performance of capillary columns were studied. The capillary columns obtained using this technique are stable in all solvents commonly used in LC and exhibit promising enantiomer resolving ability.

Abstract

High-performance liquid chromatographic enantioseparations on capillary columns containing crosslinked polysaccharide phenylcarbamate derivatives attached to monolithic silica. Chankvetadze, Bezhan; Kubota, Takateru; Ikai, Tomoyuki; Yamamoto, Chiyo; Kamigaito, Masami; Tanaka, Nobuo; Nakanishi, Kazuki; Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, Georgia. Journal of Separation Science (2006), 29(13), 1988-1995. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 146:413884 AN 2006:960756 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This study reported the application of LC-ESI/MS method to characterize O-diglycosyl flavanones of traditional Chinese medicine Fructus aurantii(Zhiqiao) and UPLC retention parameters method to expatiate the structure-retention relationship of these O-diglycosyl flavanones. The ext. of F. aurantii was found contg. neoeriocitrin, isonaringin, naringin, hesperidin, neohesperidin, and neoponcirin. Tandem mass spectrometric method was utilized to elucidate structure and differentiate the interglycosidic linkage of isomeric O-diglycosyl flavanones. Based on the relative abundance of fragments formed by fragmentation at glycosidic bonds in pos. ion mode and CID MS spectra of deprotonated mol. [M-H]- in neg. ion mode, the interglycosidic linkage of O-diglycosyl flavanones (flavonoid O-neohesperidosides and O-rutinosides, 1,2- and 1,6-) can be unambiguously differentiated. UPLC and a CSASS software were performed to obtain the retention parameters a, c and k values of these compds. The Δa, Δc, and α values within compd. pair naringin to neoriocitrin, neoponcirin to neohesperidin, naringin to isonaringin, neohesperidin to hesperidin, hesperidin to isonaringin, neohesperidin to naringin were calcd. We found there were some relationship between structure and retention parameters.

Abstract

Identification of O-diglycosyl flavanones in Fructus aurantii by liquid chromatography with electrospray ionization and collision-induced dissociation mass spectrometry. Zhou, Da-yong; Xu, Qing; Xue, Xin-ya; Zhang, Fei-fang; Liang, Xin-miao. Biotechnology Department, Dalian Institute of Chemical Physics, The Chinese Academy of Sciences, Dalian, Peop. Rep. China. Journal of Pharmaceutical and Biomedical Analysis (2006), 42(4), 441-448. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 145:404475 AN 2006:964096 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


measured. It was obsd. that the naringenin-phospholipid complex enhanced the antioxidant activity of the biomol. and protected the liver significantly for a longer time as compared with free naringenin at the same dose level. Phospholipid complex of naringenin produced better antioxidant activity than the free compd. with a prolonged duration of action, which may be helpful in reducing the fast elimination of the mol. from body.


flavanone

EP 1750651 A1 20070214 EP 2004-804019 20041217CN 1893909 A 20070110 CN 2004-80037849 20041217CA 2549509 A1 20050630 CA 2004-2549509 20041217AU 2004298356 A1 20050630 AU 2004-298356 20041217

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, HU, SK

EP 1543810 A1 20050622 EP 2003-29183 20031218

RW: BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Composition for improving skin, hair and coat health containing flavanones. Richelle, Myriam; Offord-Cavin, Elizabeth; Bortlik, Karlheinz; Bureau-Franz, Isabelle; Williamson, Gary; Nielsen, Inge Lise; Steiling, Heike; Moodycliffe, Angus. (Nestec S.A., Switz.). PCT Int. Appl. (2005), 26 pp. CODEN: PIXXD2 WO 2005058255 A1 20050630 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-EP14416 20041217. Priority: EP 2003-29183 20031218. CAN 145:299737 AN 2006:956792 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanone compds. generally have a bigger conjugate system. They are good electronic luminescence materials. Four kinds of flavanone derivs. have been optimized at the B3LYP/6-311G level. There is no imaginary frequency in vibrational anal. On these bases, their electronic spectra are calcd. by CIS method at B3LYP/6-311G level. The calcd. results are basically consistent with exptl. values. In addn., the results also indicate that the intramol. hydrogen bonding of the three compds. has been formed and the bond length is about 1.75-1.82°.

Abstract

Quantum chemistry study on fluorescence spectra of four flavanone derivatives. Su, Yu; Liu, Shan; Yang, Ming; Liao, Xian-wei. Teaching and Research Group of Chemistry, Northern Sichuan Medical College, Nanchong, Peop. Rep. China. Xinan Minzu Daxue Xuebao, Ziran Kexueban (2006), 32(4), 693-696. Publisher: Xinan Minzu Daxue Xuebao, Ziran Kexueban Bianjibu, CODEN: XMDXAF Journal written in Chinese. CAN 147:157260 AN 2006:958381 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Transcriptional regulation of the flavonoid pathway in the skin of dark-grown 'Cripps' Red' apples in response to sunlight. Bibliographic Information Answer 371:

The purple anthocyanins in potato tuber skin and flesh are primarily derived from petunidin. CDNA clones encoding the enzymes involved in anthocyanin biosynthesis, chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DRF), and UDP-glucose:flavonoid 3-O-glucosyltransferase (3GT), were isolated from Solanum pinnatisectum by RT-PCR with degenerated primers. Sequence comparison showed that they share 76-96% identities with each corresponding solanaceous gene reported previously. Each gene is a member of a multigene family. The spatial expression anal. indicated that these genes were preferentially expressed in flowers, stolons and terminal buds, and their transcripts could not detected in roots except 3GT. All the genes were induced expression in tuber skins by white light, and followed by anthocyanin accumulation. This is the first report cloning and expression of anthocyanin biosynthetic genes in wild potato (Solanum pinnatisectum).

Abstract

cDNA cloning and expression of anthocyanin biosynthetic genes in wild potato (Solanum pinnatisectum). Lu, Qi-Neng; Yang, Qing. Department of Biochemistry and Molecular Biology, College of Life Sciences, Nanjing Agricultural University, Nanjing, Peop. Rep. China. African Journal of Biotechnology (2006), 5(10), 811-818. Publisher: Academic Journals, CODEN: AJBFAH ISSN: 1684-5315. http://www.academicjournals.org/AJB/PDF/pdf2006/16May/Semagn%20et%20al.pdf Journal; Online Computer File written in English. CAN 146:334170 AN 2006:924322 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention pertains to a compn. for preventing, decreasing and/or treating skin and hair/coat disorders, such as is effected by inflammatory reactions, environmental factors, aging or cancer. In particular, the present invention relates to the use of flavanones compds. or their derivs. in nutritional, cosmetic or pharmaceutical compns. for improvement of human or pet animal skin and coat conditions. For example, mineral water was prepd. by adding hesperetin-7-glucose, in an amt. of 0.01 mg to 200 mg per L, estg. that the av. consumption is of about 1 L per day.

Abstract WO 2004-EP14416 W 20041217EP 2003-29183 A 20031218Priority Application NO 2006003200 A 20060912 NO 2006-3200 20060710 MX 2006PA06773 A 20060904 MX 2006-PA6773 20060615US 20070129428 A1 20070607 US 2006-596468 20060614IN 2006DN03349 A 20070824 IN 2006-DN3349 20060609JP 2007514695 T 20070607 JP 2006-544359 20041217BR 2004017723 A 20070403 BR 2004-17723 20041217

R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR


flavanone

Polyvinylpyrrolidone (PVP) and poly(ethylene glycol) (PEG) solid dispersion systems with flavanone glycosides, naringin and Abstract

Dissolution enhancement of flavonoids by solid dispersion in PVP and PEG matrixes: a comparative study. Kanaze, F. I.; Kokkalou, E.; Niopas, I.; Georgarakis, M.; Stergiou, A.; Bikiaris, D. Department of Pharmacy, School of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki, Greece. Journal of Applied Polymer Science (2006), 102(1), 460-471. Publisher: John Wiley & Sons, Inc., CODEN: JAPNAB ISSN: 0021-8995. Journal written in English. CAN 145:455609 AN 2006:896610 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


One new 1,3-diphenylpropane, viscolin (1), and one new flavanone, (2S)-7,4'-dihydroxy-5,3'-dimethoxyflavanone (2), together with thirty-nine known compds., which included eleven known flavanones, two chromones, fourteen benzenoids, one inositol, two pyrimidines, four triterpenoids and five steroids, were isolated and characterized from Viscum coloratum. Structures of new compds. were detd. by spectral anal. Among them, viscolin (1) showed the most significant inhibition on superoxide anion generation by human neutrophils in response to fMLP (formyl-L-methionyl-L-leucyl-L-phenylalanine).

Abstract

The inhibition of superoxide anion generation in human neutrophils by Viscum coloratum. Leu, Yann-Lii; Hwang, Tsong-Long; Chung, Yu-Ming; Hong, Pao-Yun. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Tao-Yuan, Taiwan. Chemical & Pharmaceutical Bulletin (2006), 54(7), 1063-1066. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 145:431906 AN 2006:896921 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids, including anthocyanins, flavonols, and condensed tannins (CTs), are synthesized by a common biosynthetic pathway. Anthocyanins are responsible for the red color in apple fruits, while CTs and flavonols are potent anti-oxidants which may be beneficial in the human diet. The effect of sunlight on flavonoid accumulation and gene transcription was investigated in fruit skin of the red apple variety Malus × domestica cv. 'Cripps' Red'. Individual fruit growing on trees and covered with bags 46 d after full bloom (DAFB) failed to accumulate anthocyanins by 147 DAFB, 2 wk before harvest. In contrast, control fruit, grown under natural light conditions, accumulated anthocyanins up to 140 ng/mg fresh wt. (FW) of skin. The accumulation of flavonols was moderately reduced in bagged fruit, but the synthesis of CTs was unaffected. Exposure of bagged fruit to sunlight induced anthocyanin synthesis up to .apprx.30 ng/mg FW of skin after 13 d (harvest), but had no effect on the synthesis of flavonols or CTs. The synthesis of anthocyanins correlated with an increase in the steady-state transcript levels of all flavonoid pathway genes except those specific for CT synthesis. These data suggest that transcription of most apple flavonoid genes is controlled by a common regulatory mechanism that is light-responsive.

Abstract

Takos, Adam M.; Robinson, Simon P.; Walker, Amanda R. Division of Plant Industry, Adelaide Laboratory, Commonwealth Scientific and Industrial Research Organisation, Glen Osmond, South Australia, Australia. Journal of Horticultural Science & Biotechnology (2006), 81(4), 735-744. Publisher: Headley Brothers Ltd., CODEN: JHSBFA ISSN: 1462-0316. Journal written in English. CAN 146:289351 AN 2006:911809 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 376:

Hesperidin (HDN) is a flavanone glycoside abundantly found in citrus fruits. HDN has been reported to possess significant activities against allergy, hemorrhoids, hormonal disorders and ulcers. Other reported activities include anti-inflammatory, analgesic, antibacterial, antifungal, antiviral, antioxidant and free radical scavenger activity. A potentially important effect of endotoxin is the increased prodn. of reactive oxygen intermediates as O2⋅-, peroxides and nitric oxide. The study reported here show a beneficial effect of HDN in amelioration of endotoxin-induced hepatic dysfunction and oxidative stress in the liver of rats. Hepatotoxicity was induced by administering lipopolysaccharide (LPS), in a single dose of 1 mg/kg i.p. to the rats. A marked hepatic dysfunction evident by rise in serum levels of liver enzymes (ALT, AST, ALP) and total bilirubin (p < 0.05) was obsd. Serum and tissue nitrite levels were also increased. LPS challenge further increased thiobarbituric acid reactive substances (TBARS) levels, whereas glutathione (GSH) content and superoxide dismutase (SOD) activity were decreased in the liver homogenates of the rats showing a marked oxidative stress. HDN administration successfully and dose dependently attenuated these effects of LPS. In conclusion, these findings suggest that HDN attenuates LPS-induced hepatotoxicity possibly by preventing cytotoxic effects of NO and oxygen free radicals.

Abstract

Beneficial effect of hesperidin on lipopolysaccharide-induced hepatotoxicity. Kaur, Gaganjit; Tirkey, Naveen; Chopra, Kanwaljit. Pharmacology Division, University Institute of Pharmaceutical Sciences, Panjab University, Chandigarh, India. Toxicology (2006), 226(2-3), 152-160. Publisher: Elsevier Ltd., CODEN: TXCYAC ISSN: 0300-483X. Journal written in English. CAN 145:306725 AN 2006:877209 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The arom. chem. constituents in Aralia subcapitata Hoo were studied. The dry bark of Aralia subcapitata Hoo was extd. by dichloromethane and n-butanol, and the exts. were purified by silica gel column chromatog., Sephadex LH-20, and macroporous resin column chromatog. resp. 4 Arom. chem. constituents were obtained and their structures were identified as 6,7-dimethoxycoumarin, caffeic acid, 4'-hydroxy-flavanone-7-O-β-D-glucopyranoside, and isoliquiritin.

Abstract

Study on aromatic chemical constituents in Aralia subcapitata Hoo. Xu, Xudong; Yang, Lingshan. Institute of Medicinal Plant, Chinese Academy of Medicinal Sciences, Peking Union Medical College, Beijing, Peop. Rep. China. Zhongguo Zhongyao Zazhi (2005), 30(5), 398-399. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese. CAN 147:26993 AN 2006:894028 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


hesperidin, and their aglycons, naringenin and hesperetin, were prepd., using solvent evapn. method, to enhance their dissoln. rates that may affect their bioavailability. Drug release of both flavanone glycosides and their aglycons was directly affected by the phys. state of solid dispersions. Powder-x-ray diffraction technique in combination with scanning and TEM revealed that PVP polymer formed amorphous nanodispersion systems with flavanone aglycons, while such systems could not be formed with their glycosides, which are bulkier mols. Fourier transform IR spectra suggest the presence of hydrogen bonds between PVP carbonyl groups and hydroxyl groups of both flavanone aglycons. These interactions prevent the crystn. of naringenin and hesperetin aglycons in PVP matrix. The ability of PEG carrier to form hydrogen bonds with flavanone glycosides or aglycons was limited, and as a result both flavanone glycosides and their aglycons remain in the cryst. form. For this reason, the soly. enhancement of PEG solid dispersions was lower than when PVP was used as drug carrier. At pH 6.8, the % release of naringenin and hesperetin from PVP/naringenin-hesperetin (80/20) solid dispersion was 100% while in PEG solid dispersions, it was not higher than 60-70%.


flavanone

Genetic similarities between plant interactions with microbial pathogens and wheat interactions with Hessian fly larvae prompted us to Abstract

Gene-for-gene defense of wheat against the hessian fly lacks a classical oxidative burst. Giovanini, Marcelo P.; Puthoff, David P.; Nemacheck, Jill A.; Mittapalli, Omprakash; Saltzmann, Kurt D.; Ohm, Herbert W.; Shukle, Richard H.; Williams, Christie E. Department of Agronomy, Purdue University, West Lafayette, IN, USA. Molecular Plant-Microbe Interactions (2006), 19(9), 1023-1033. Publisher: APS Press, CODEN: MPMIEL ISSN: 0894-0282. Journal written in English. CAN 145:500633 AN 2006:865999 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


An iridoid glucoside, lamiide (1); 4 phenylethanoid glycosides, acteoside (2), β-OH acteoside (3), leucosceptoside A (4) and samioside (5); a caffeic acid ester, chlorogenic acid (6); 2 flavone glucosides, luteolin-7-O-glucopyranoside (7) and chrysoeriol-7-O-glucopyranoside (8); and a flavanone aglycon, naringenin (9), were isolated from the aerial parts of Phlomis syriaca. The structures of the isolated compds. were elucidated by means of spectroscopic (UV, IR, 1D- and 2D-NMR, and FAB-MS) methods. Free radical scavenging activity of the isolated compds. was detd. using the radical 2,2-diphenyl-1-picrylhydrazyl (DPPH), spectroscopically.

Abstract

Secondary metabolites from Phlomis syriaca and their antioxidant activities. Harput, U. Sebnem; Calis, Ihsan; Saracoglu, Iclal; Donmez, Ali A.; Nagatsu, Akito. Faculty of Pharmacy, Department of Pharmacognosy, Hacettepe University, Ankara, Turk. Turkish Journal of Chemistry (2006), 30(3), 383-390. Publisher: Scientific and Technological Research Council of Turkey, CODEN: TJCHE3 ISSN: 1300-0527. Journal written in English. CAN 146:270143 AN 2006:866118 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. constituents of Dryopteris sublaeta Ching et Hsu were studied. Fresh plant of Dryopteris sublaeta Ching et Hsu was extd. twice with boiling water, the ext. was concd. under reduced pressure at 50°. The concd. material was partitioned with ether, Et acetate, and n-butanol. The fraction of ether ext. was chromatographed over silica gel column. The compds. were identified on the basis of their physicochem. and spectral data. Four compds. were obtained and identified as 2(S)-5,7,3'-trihydroxy-6,8-dimethyl-5'-methoxy-flavanone (1), matteucinol (2), desmethoxymatteucinol (3), and 5,7,2'-trihydroxy-6,8-dimethyl-flavanone (4). Compd. 1 is a new one, the others are isolated from Dryopteris for the first time.

Abstract

New flavanone from Dryopteris sublaeta. Feng, Weisheng; Cao, Xinwei; Zheng, Xiaoke; Kuang, Haixue. Henan College of Traditional Chinese Medicine, Zhengzhou, Peop. Rep. China. Yaoxue Xuebao (2005), 40(5), 443-446. Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in English. CAN 146:375811 AN 2006:868420 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

KR 2005006562 A 20050117 KR 2003-46437 20030709 Patent No. Kind Date Application No. Date Patent Family Information

Production of composition of citrus fruits having increased content of flavanone compound by addition of glycosidase to citrus fruits. Ahn, Jong Seog; Ahn, Soon Cheol; Kim, Bo Yeon; Kim, Min Soo; Oh, Won Keun. (Cheju Provincial Government, S. Korea; Korea Research Institute of Bioscience and Biotechnology). Repub. Korean Kongkae Taeho Kongbo (2005), No pp. given. CODEN: KRXXA7 KR 2005006562 A 20050117 Patent written in Korean. Application: KR 2003-46437 20030709. Priority: . CAN 145:270708 AN 2006:847937 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


CD (CD) has played an important role in detg. the abs. configuration of chiral mols. In particular, the recent advances on theor. calcns. of CD spectra have greatly enhanced its value in this regard. The 3,8"-biflavonoids represent a biosynthetically important group of natural products with significant biol. activities. The restricted rotation about the C3 - C8" interflavanyl bond has made it extremely difficult to assign their abs. configurations. Although the empirical CD rule has attempted to address this issue, no solid evidence, e.g., from total synthesis and X-ray crystallog., has been available to support the deduced abs. configurations. In the current study, theor. calcns. of the electronic CD spectra of flavanone-(3->8")-flavone type and flavanone-(3->8")-dihydroflavonol type biflavonoids have been carried out using time-dependant d. functional theory (TDDFT) with 6-31G* basis set in Gaussian03. The results have provided profound evidence in interpreting the exptl. obsd. CD spectra, and thus unequivocally detg. the abs. configurations of this class of compds.

Abstract

Theoretical calculations of circular dichroism of 3, 8"-biflavonoids. Ding, Yuanqing; Li, Xing Cong; Ferreira, Daneel. National Center for Natural Products Research, The University of Mississippi, University, MS, USA. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, CA, United States, Sept. 10-14, 2006 (2006), CELL-105. Publisher: American Chemical Society, Washington, D. C CODEN: 69IHRD Conference; Meeting Abstract; Computer Optical Disk written in English. AN 2006:857512 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


investigate defense and counterdefense mechanisms. Plant oxidative burst, a rapid increase in the levels of active oxygen species (AOS) within the initial 24 h of an interaction with pathogens, commonly is assocd. with defenses that are triggered by gene-for-gene recognition events similar to those involving wheat and Hessian fly larvae. RNAs encoded by Hessian fly superoxide dismutase (SOD) and catalase (CAT) genes, involved in detoxification of AOS, increased in first-instar larvae during both compatible and incompatible interactions. However, mRNA levels of a wheat NADPH oxidase (NOX) gene that generates superoxide (O2-) did not increase. In addn., inhibiting wheat NOX enzyme with diphenyleneiodonium did not result in increased survival of avirulent larvae. However, nitro blue tetrazolium staining indicated that basal levels of O2- are present in both uninfested and infested wheat tissue. MRNA encoded by wheat genes involved in detoxification of the cellular environment, SOD, CAT, and glutathione-S-transferase did not increase in abundance. Histochem. staining with 3,3-diaminobenzidine revealed no increases in wheat hydrogen peroxide (H2O2) during infestation that were correlated with the changes in larval SOD and CAT mRNA. However, treatment with 2',7'-dichlorofluorescin demonstrated the presence of basal levels of H2O2 in the elongation zone of both infested and uninfested plants. The accumulation of a wheat flavanone 3-hydroxylase mRNA did show some parallels with larval gene mRNA profiles. These results suggested that larvae encounter stresses imposed by mechanisms other than an oxidative burst in wheat seedlings.


flavanone

CN 1813774 A 20060809 CN 2005-10023740 20050201 Patent No. Kind Date Application No. Date Patent Family Information

Liposomes containing ganglioside and trivalent chromium for lowering blood sugare and treating diabetes. Du, Shiming. (Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 15pp. CODEN: CNXXEV CN 1813774 A 20060809 Patent written in Chinese. Application: CN 1002-3740 20050201. Priority: . CAN 145:299489 AN 2006:819613 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new 2,3-methylated 3-monoacetylated 6-O-tert-butyldimethylsilylated β-CD deriv. was synthesized and chem. bonded onto aminopropyl derivatized monolithic silica HPLC columns. In this CD deriv., only one of seven Me groups in 3-position was substituted by an acetyl group. Its applicability as a chiral stationary phase for HPLC was tested and compared with exclusively 2,3-methylated 6-O-tert-butyldimethylsilylated β-CD immobilized onto aminopropyl-modified monoliths. Thirty-two chiral compds. from different chem. classes and different functionalities were tested under RP conditions. Fourteen compds. were resolved into their enantiomers by methylated 6-O-tert-butyldimethylsilylated β-CD. Using methylated/acetylated 6-O-tert-butyldimethylsilylated β-CD as the chiral stationary phase 7 analytes were successfully stereodifferentiated.

Abstract

Enantiomer separation on monolithic silica HPLC columns using chemically bonded methylated and methylated/acetylated 6-O-tert-butyldimethyl-silylated β-cyclodextrin. Bayer, Mathias; Haensel, Clarissa; Mosandl, Armin. Institut fuer Lebensmittelchemie, Biozentrum J.W. Goethe-Universitaet, Frankfurt/Main, Germany. Journal of Separation Science (2006), 29(11), 1561-1570. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 146:329304 AN 2006:827876 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method of making a compn. of citrus fruits increased in the content of a flavanone compd. by the addn. of glycosidase to citrus fruits is provided. Therefore, the compn. contains active aglycon type flavonoids excellent in physiol. activity in large quantities and can be effectively used as food such as functional food, health supplementary food and processing food, or feed additives. Citrus fruits are subjected to an enzyme reaction by the addn. of 0.001 to 10% by wt. of glycosidase to citrus fruits. The enzyme reaction is performed at 20 to 70 °C at a pH of 5 to 7 for 30 to 48h. For the optimization of the enzyme reaction, the citrus fruits are ground and added with 1 to 10 times with distd. water. The glycosidase is selected from cellulase, hemicellulase, pectinase, xylanase, beta-glucosidase, glucoamylase and amylase to transfer an inactive glycon flavonoid compd. to an active aglycon flavonoid compd. The flavonoid compd. is naringenin, hesperetin, tangeretin and sinensetin.

Abstract KR 2003-46437 20030709Priority Application


flavanone

WO 2006-JP302918 W 20060214JP 2005-36338 A 20050214Priority Application KR 2007102737 A 20071019 KR 2007-720389 20070906 CN 101115837 A 20080130 CN 2006-80004631 20070810




W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Transgenic plant transformed with a vector carrying aromatic hydrocarbon receptor gene AhR and its uses in detection of environmental burden chemicals. Togami, Junichi; Okuhara, Hiroaki; Tanaka, Yoshikazu. (Suntory Limited, Japan). PCT Int. Appl. (2006), 52pp. CODEN: PIXXD2 WO 2006085699 A1 20060817 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2006-JP302918 20060214. Priority: JP 2005-36338 20050214. CAN 145:242876 AN 2006:818103 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The compn. comprising ganglioside 1-60 parts, trivalent chromium ion 0.15-0.2 parts, e.g chromium picolinate, and optionally flavonoids 0.001-10000 parts, inositol 0.001-10000 parts is used for treating and prevent diabete or prepg. relevant health-care food.

Abstract CN 2005-10023740 20050201Priority Application


flavanone

A stable compn. of an amorphous component (such as a bioactive) and a carrier polymer is formed by mixing a bridging polymer with the bioactive and the carrier polymer, wherein the bridging polymer is a hydrogen bond donor to both the bioactive and the carrier polymer, thereby forming a compn. in which the bioactive and the carrier polymer have less of a tendency to crystallize than if the

Abstract WO 2006-GB467 W 20060210GB 2005-2790 A 20050210Priority Application


EP 1853225 A1 20071114 EP 2006-709705 20060210



WO 2006085089 A1 20060817 WO 2006-GB467 20060210Patent No. Kind Date Application No. Date Patent Family Information

Solid dispersion of hydrophobic bioactive comprising polymers. Buckton, Graham; Brocchini, Stephen; Fletcher, John; Al-Obaidi, Hisham. (Pharmaterials Limited, UK). PCT Int. Appl. (2006), 37pp. CODEN: PIXXD2 WO 2006085089 A1 20060817 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-GB467 20060210. Priority: GB 2005-2790 20050210. CAN 145:218024 AN 2006:817430 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Described is a transgenic plant transformed with a vector carrying mouse arom. hydrocarbon receptor gene AhR. The vector contains a chimeric gene encoding for the DNA binding domain from Escherichia coli LexA, AhR, and the transactivation domain from human herpesvirus VP16. The chimeric gene is under control of an AhR ligand stimulus-inducible promoter. The vector also contains a nucleotide sequence encoding for dsRNA for RNA silencing of a gene involved in the synthesis of anthocyanin, for example flavanone 3 hydroxylase gene or flavonoid 3',5' hydroxylase gene. The transgenic plant is useful in detecting an environmental burden chem., for example dioxin and arom. hydrocarbon analogs, by observing a change in its flower color.

Abstract


flavanone

Microwave-Assisted Reaction of 2'-Hydroxychalcones with Hydrazides to Synthesize Flavanone Hydrazone and 4,5-Dihydropyrazole Derivatives. Nie, Aihua; Huang, Ziwei. Burnham Institute for Medical Research, La Jolla, CA, USA. Journal of Combinatorial Chemistry (2006), 8(5), 655-658. Publisher: American Chemical Society, CODEN: JCCHFF ISSN:


A newly synthesized flavanone deriv., (±)-(3aRS,4SR)-2-(2-chloro-4-methyl- sulfonylphenyl)-4'-chloro-3a, 4-diethoxy-flavane[4,3-d]-Δ1,9b-1,2,3-thiadiazoline (MSFTZ), was investigated for its antileukemia activity and mol. mechanisms. Cytotoxicity assay confirmed the high antiproliferative efficiency of MSFTZ in six leukemia cell lines (including two drug-resistant cell lines), with 50% inhibition of cell viability values ranging from 1.0 to 9.2 μmol/l. The results of flow cytometry assay showed that the percentage of apoptotic HL-60 cells was 68.3% after 48 h treatment with MSFTZ, suggesting that the activation of the apoptosis pathway was an anticancer property of MSFTZ. Furthermore, the protein changes related to apoptosis were investigated. Exposure of HL-60 cells to MSFTZ induced pro-caspase-9 and pro-caspase-3 cleavage, X-linked inhibitor of apoptosis protein and Bcl-XL downregulation, and poly(ADP-ribose) polymerase degrdn. Treatment of cells with MSFTZ resulted in a time-dependent redn. in phosphorylation (activation) of extracellular signal-regulated kinase 1/2 and an increase in phosphorylation (activation) of Jun N-terminal kinase. Taken together, our results demonstrated that activation of mitogen-activated protein kinase and apoptotic cascade is involved in MSFTZ-induced antileukemia activity. All data suggest that MSFTZ is a promising chemotherapy drug.

Abstract

Antileukemia activity of MSFTZ-a novel flavanone analog. He, Qiaojun; Li, Runping; Fang, Liang; Ying, Huazhou; Hu, Yongzhou; Yang, Bo. Institute of Pharmacology and Toxicology, School of Pharmaceutical Sciences, Zhejiang University, Hangzhou, Peop. Rep. China. Anti-Cancer Drugs (2006), 17(6), 641-647. Publisher: Lippincott Williams & Wilkins, CODEN: ANTDEV ISSN: 0959-4973. Journal written in English. CAN 145:306064 AN 2006:798840 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The cytotoxic components in Amorpha fruticosa were extd. by 75% ethanol and Et acetate, resp. A total of five cytotoxic compds. were obtained and they were identified as β-sitosterol (I), 5,7-dihydroxy-8-geranyl flavanone (II), tephrosin (III), 7',4-dimethoxyisoflavone (IV) an 7,2',4',5'-tetramethoxyisoflavone (V). Compds. I and IV were isolated from A. fruticosa for the first time. In vitro cytotoxic expt. showed that Et acetate ext. had better antitumor activity.

Abstract

Cytotoxic components in Amorpha fruticosa. Jiang, Hong; Bai, Liping; Kang, Tingguo. Liaoning College of Traditional Chinese Medicine, Shenyang, Liaoning Province, Peop. Rep. China. Zhongcaoyao (2005), 36(10), 1469-1471. Publisher: Zhongcaoyao Zazhi Bianjibu, CODEN: CTYAD8 ISSN: 0253-2670. Journal written in Chinese. CAN 147:5682 AN 2006:800816 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


bridging polymer were not present. Thus, addn. of poly(hydroxypropyl methacrylate) (PHPMA) as a secondary component to griseofulvin/polyvinylpyrrolidone dispersion improved the amorphous stability of griseofulvin during storage for 13 wk at 50° and 0% relative humidity, over the griseofulvin/polyvinylpyrrolidone dispersion.


flavanone

Reduction kinetics of the free stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH.bul.) for determination of the antiradical activity of citrus juices. Sendra, Jose M.; Sentandreu, Enrique; Navarro, Jose L. Instituto de Agroquimica y Tecnologia de Alimentos, Valencia, Spain. European Food Research and Technology (2006), 223(5), 615-624. Publisher: Springer GmbH,


Influence of structural features of mols. on anti-mutagenic activity of flavonoids is investigated. For this purpose the new principle of the description of dependence of biol. activity of chem. compds. from their structure is used. It is based on the use of compd. descriptors. It is established that antimutagenic flavonoids contain C4 keto-group and double bond at positions C2 and C3, contain hydroxyl group/s. Antimutagenic flavonoids do not have amino and nitro groups in their structures.

Abstract

Structure-activity relationships of antimutagenic flavonoids. Mustafaev, O. N.; Abilev, S. K.; Melnik, V. A.; Tarasov, V. A. Inst. Obshch. Genet. im. N. I. Vavilova, RAN, Russia. Ekologicheskaya Genetika (2005), 3(4), 11-18. Publisher: OOO "IzdatelÏstvo N-L", CODEN: EGKEAE ISSN: 1811-0932. Journal written in Russian. CAN 146:352822 AN 2006:786121 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

NNH

O

N N

O

OH

OH

O

1R

R2

R3

R2

R3

R1

R21R

I

III

II

Two distinct combinatorial libraries of flavanone hydrazones I (R1 = H, F; R2 = Ph, 4-FC6H4, 4-ClC6H4, 4-MeC6H4; R3 = 4-MeC6H4, 4-F3CC6H4, 4-pyridyl) and 4,5-dihydropyrazoles II were conveniently synthesized from the same reagents, chalcones III and arom. hydrazides R3CONHNH2, under microwave irradn. conditions with the reaction pathway depending only on the reaction temp.

Abstract 1520-4766. Journal written in English. CAN 145:377254 AN 2006:797379 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

A novel chalcone from Coreopsis tinctoria Nutt. Zhang, Yuan; Shi, Shepo; Zhao, Mingbo; Jiang, Yong; Tu, Pengfei. Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, Peop. Rep. China. Biochemical Systematics and Ecology (2006), 34(10), 766-769. Publisher: Elsevier Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 146:247426 AN 2006:769762 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Because of their several biol. activities, flavonoids may have an important role in explaining the protective effects of vegetables, fruit, and, possibly, tea against cancer. The potential relation between flavonoids and colorectal cancer risk was investigated using data from a multicentric Italian case-control study, including 1,953 cases of colorectal cancers (1,225 colon cancers and 728 rectal cancers) and 4,154 hospital controls admitted for acute nonneoplastic diseases. We have applied recently published data on the compn. of foods and beverages, in terms of six principal classes of flavonoids, on dietary information collected through a validated food-frequency questionnaire. Odds ratios (OR) were estd. by multiple logistic regression models, including terms for sex, age, study center, family history of colorectal cancer, education, alc. consumption, body mass index, phys. activity, and energy intake. A reduced risk of colorectal cancer was found for increasing intake of isoflavones (OR, 0.76, for the highest vs. the lowest quintile, Ptrend = 0.001), anthocyanidins (OR, 0.67, Ptrend < 0.001), flavones (OR, 0.78, Ptrend = 0.004), and flavonols (OR, 0.64, Ptrend < 0.001). No significant assocn. was found for flavan-3-ols (OR, 0.98), flavanones (OR, 0.96), and total flavonoids (OR, 0.97). The ests. did not substantially differ for colon and rectal cancers, as well as in strata of sex, age, and body mass index. The findings of this large study provide support for an inverse assocn. of selected classes of flavonoids with colorectal cancer risk.

Abstract

Flavonoids and Colorectal Cancer in Italy. Rossi, Marta; Negri, Eva; Talamini, Renato; Bosetti, Cristina; Parpinel, Maria; Gnagnarella, Patrizia; Franceschi, Silvia; Dal Maso, Luigino; Montella, Maurizio; Giacosa, Attilio; La Vecchia, Carlo. Istituto di Ricerche Farmacologiche "Mario Negri", Milan, Italy. Cancer Epidemiology, Biomarkers & Prevention (2006), 15(8), 1555-1558. Publisher: American Association for Cancer Research, CODEN: CEBPE4 ISSN: 1055-9965. Journal written in English. CAN 146:183753 AN 2006:782058 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


An approxn. is made to the redn. kinetics of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH.bul.) by the free radical scavenging activity of juices from sweet orange (Citrus sinensis L.), clementine (Citrus reticulata Blanco) and satsuma (Citrus unshiu K. Marc), as well as the deduction of a kinetic equation to fit the exptl. data. This equation contains two contributions. The first contribution accounts for the concn. of DPPH.bul. reduced by the cumulative antiradical activity of those citrus juice components that are capable of fast hydrogen atom transfer (fast-kinetics), mainly ascorbic acid and some polyphenolic derivs.; the second accounts for the concn. of DPPH.bul. reduced by the cumulative antiradical activity of those citrus juice components that are capable of slow hydrogen atom transfer (slow-kinetics), mainly flavanone-7-O-glycosides and some polyphenolic derivs. This methodol. thus permits the detn. of the total antiradical activity of a citrus juice (expressed as molar equivalents of ascorbic acid), as well as the partial contributions of the cumulative antiradical activities (also expressed as molar equivalents of ascorbic acid) due to both fast-kinetics and slow-kinetics.

Abstract

CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 145:355445 AN 2006:785531 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Supercritical fluid extraction of antioxidant compounds from oregano. Cavero, Sofia; Garcia-Risco, Monica R.; Marin, Francisco R.; Jaime, Laura; Santoyo, Susana; Senorans, F. Javier; Reglero, Guillermo; Ibanez, Elena. Area de Tecnologia de Alimentos, Facultad de Ciencias, Unidad Asociada al IFI-CSI, Universidad Autonoma de Madrid, Madrid, Cantoblanco, Spain. Journal of Supercritical Fluids (2006), 38(1), 62-69. Publisher: Elsevier B.V., CODEN: JSFLEH ISSN: 0896-8446. Journal written in English. CAN 145:417304 AN 2006:757751 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Peroxynitrite is thought to contribute to the progression of many diseases including cardiovascular disease, cancer, and neurodegenerative disorders. The authors report that pretreatment of fibroblasts with the citrus flavanone, hesperetin, prior to peroxynitrite exposure protects against peroxynitrite-mediated cytotoxicity. This protection was partially mediated by the intracellular scavenging of peroxynitrite by hesperetin as exposure of fibroblasts to peroxynitrite following hesperetin loading led to the formation of two intracellular nitro-hesperetin derivs. In addn., protection appeared to be mediated by hesperetin-induced changes in MAP kinase signaling. Exposure of fibroblasts to hesperetin led to concn.-dependent increases in the phosphorylation of ERK1/2 and was obsd. to restore peroxynitrite-mediated decreases in ERK1/2 phosphorylation. The authors propose that the protective potential of hesperetin in fibroblasts may be mediated both by intracellular scavenging of peroxynitrite and by modulation of fibroblast signaling.

Abstract

Modulation of peroxynitrite-induced fibroblast injury by hesperetin: A role for intracellular scavenging and modulation of ERK signalling. Pollard, Susan E.; Whiteman, Matthew; Spencer, Jeremy P. E. Molecular Nutrition Group, School of Chemistry, Food Biosciences and Pharmacy, University of Reading, Reading, UK. Biochemical and Biophysical Research Communications (2006), 347(4), 916-923. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 145:241649 AN 2006:765788 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH

OH

OH

HO

O

CH 2

O

OH

O

OH

OH

COH2C

CO 2H

I

Anal. of the dried flowers of Coreopsis tinctoria Nutt. led to the isolation and characterization of a novel compd., namely, okanin-4'-O-β-(6''-O-malonyl)glucopyranoside (I), together with 11 known flavonoids.

Abstract


flavanone

WO 2006-US2267 W 20060120US 2005-645962P P 20050121US 2005-645916P P 20050120Priority Application


EP 1841415 A2 20071010 EP 2006-719216 20060120US 20060276416 A1 20061207 US 2006-336258 20060120CA 2595486 A1 20060727 CA 2006-2595486 20060120AU 2006206274 A1 20060727 AU 2006-206274 20060120




Methods and compositions using sirtuin modulators for treating flushing and drug-induced weight gain. Sinclair, David; Milburn, Michael; Langer, Robert S.; Westphal, Christoph H. (Sirtris Pharmaceuticals, Inc., USA). PCT Int. Appl. (2006), 268 pp. CODEN: PIXXD2 WO 2006079021 A2 20060727 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US2267 20060120. Priority: US 2005-645916 20050120; US 2005-645962 20050121. CAN 145:202956 AN 2006:734482 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The possibility of using oregano leaves as a new source of natural antioxidants has been investigated. Oregano leaves were extd. using a pilot-scale SFE plant under a wide range of extg. conditions (at different extn. pressures and temps. and considering the addn. of ethanol as modifier) with the objective of knowing not only the best extn. conditions but also the variables that control the process in terms of extn. and fractionation of products of high antioxidant activity. The different fractions obtained at each exptl. condition tested were characterized in terms of chem. compn. by using liq. chromatog.-diode array detection (LC-DAD) and liq. chromatog.-mass spectrometry (LC-MS). Nine compds. have been tentatively identified as belonging to a specific family of compds. (flavone, flavanone and flavonol); their aglycon structures have been proposed using UV spectra profile while a tentative pattern of substitution, based on their mass spectra and mol. ion (MH+) major fragments, has been also given. Antioxidant activity was measured using 2 different in vitro assays (1,1-diphenyl-2-picrylhydrazyl (DPPH) antiradical test and bleaching β-carotene method).


flavanone

Novel compositions for preventing and treating neurodegenerative and blood coagulation disorders. Milburn, Michael; Milne, Jill; Westphal, Christopher H.; Normington, Karl D.; Fujii, Jennifer; Dipp, Michelle; Elliot, Peter. (Sirtris Pharmaceuticals, Inc., USA). PCT Int. Appl. (2006), 294 pp. CODEN: PIXXD2 WO 2006076681 A2 20060720 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ,


The present invention is related to a conditioning compn. for hair comprising flavone derivs. and particularly on enhanced deposition of flavone derivs. onto hair. Accordingly, the compns. comprise at least one conditioning agent, at least one org. solvent, at least one flavone deriv. and at least one hydroxycarboxylic and/or dicarboxylic acid and has a pH below 4.5. The conditioning compn. of the present invention can be in the form of a shampoo, cleansing - conditioning compn., or in the form of a conditioner used after washing hair with cleansing compns. Thus, a conditioning shampoo contained Sodium lauryl ether sulfate 11.0, coco glucoside 4.0, cocoamidopropylbetaine 1.5, cationic polymer (Polyquaternium-10) 0.2, benzyl alc. 0.25, perfume, preservative as needed, PEG-60-hydrogenated castor oil 0.5, PEG-18 glyceryl cocoate/oleate 2.0, t-flavanone (trans-3,4'-dimethylflavanone) 0.3, malic acid 1.00, and water to 100.0%, resp.

Abstract EP 2004-30563 20041223Priority Application

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, HU, PL, SK, BA, HR, IS, YU


Hair conditioning composition containing flavone derivatives. Molenda, Michael; Lateulere, Magali; Golinski, Frank; Lichtl, Rixa. (Kpss-Kao Professional Salon Services G.m.b.H., Germany). Eur. Pat. Appl. (2006), 15 pp. CODEN: EPXXDW EP 1683512 A1 20060726 Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, HU, PL, SK, BA, HR, IS, YU. Patent written in English. Application: EP 2004-30563 20041223. Priority: . CAN 145:173536 AN 2006:729879 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention provides methods and compns. for treating and/or preventing flushing and/or wt. gain. The methods may comprise modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary embodiments include methods and compns. for counteracting drug-induced wt. gain and/or drug-induced flushing by administering a sirtuin-activating compd. Compds. of the invention include e.g.resveratrol analogs (prepn. described).

Abstract


flavanone

Flavonones and dihydroflavonols. Grayer, Renee J.; Veitch, Nigel C. Jodrell Laboratory, Royal Botanic Gardens, Kew, Bibliographic Information Answer 397:

Provided herein are methods and compns. for treating or preventing neurodegenerative disorders or blood coagulation disorders. Methods may comprise modulating the activity or level of a sirtuin, such as SIRT1 or Sir2. Exemplary methods comprise contacting a cell with a sirtuin activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compd., such as nicotinamide.

Abstract WO 2006-US1428 W 20060113US 2005-753606P P 20051223US 2005-736528P P 20051114US 2005-692785P P 20050622US 2005-667179P P 20050330US 2005-643921P P 20050113Priority Application






VC, VN, YU, ZA. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2006-US1428 20060113. Priority: US 2005-643921 20050113; US 2005-667179 20050330; US 2005-692785 20050622; US 2005-736528 20051114; US 2005-753606 20051223. CAN 145:180995 AN 2006:710888 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 400:

In this study, we discovered that flavonoids belonging to the subclasses: (flavanone, flavone, and flavonol) display differential effects on the synthesis of collagen in human dermal fibroblasts. At 80 μg/mL flavonoids quercetin-3,3',4', 5,7-pentahydroxyflavone, 3-Me quercetin, and 7-hydroxyflavone significantly decreased the total protein concn. which was a direct consequence of their cytotoxic effect, while naringenin exhibited no effect on total collagen and total protein concn. Quercetin-3,3'4',7-tetramethyl ether, 4'-hydroxyflavanone, flavanone, and fisetin significantly decreased collagen concn. while morin, rutin, and chrysin increased collagen concn. without changing the overall protein concn. The initial screening performed in this study enables the identification of compds. that exert significant effects on fibroblast function and show potential as starting material for pharmaceutical prepns. targeted against various disorders centered around disturbed collagen metab.

Abstract

Effect of Different Flavonoids on Collagen Synthesis in Human Fibroblasts. Stipcevic, Tamara; Piljac, Jasenka; Vanden Berghe, Dirk. Department of Molecular Medicine, Rudjer Boskovic Institute, Zagreb, Croatia. Plant Foods for Human Nutrition (New York, NY, United States) (2006), 61(1), 29-34. Publisher: Springer, CODEN: PFHNE8 ISSN: 0921-9668. Journal written in English. CAN 146:177051 AN 2006:682939 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids-enriched tissues of citrus such as peel, immature fruit and flower are consumed as culinary seasonings, tea ingredients in China for centuries. This HPLC quant. study on the five citrus flavonoids, naringin, hesperidin, neohesperidin, sinensetin and nobiletin on a wide range of Chinese citrus fruits and several Traditional Chinese Medicinal food ingredients in East China, revealed a great diversity in flavonoid compn. Huyou peel (C. paradisi cv. Changshanhuyou) was found to be the best naringin (3.25%) and neohesperidin (2.76%) source; C. aurantium, a major ingredient of several citrus-related TCM, is also a suitable source of naringin and neohesperidin, and a good juice source for flavanone glycosides; the peel of Wenzhoumiju (C. unshiu) is one of the richest local species in hesperidin (up to 6.25%); Zaoju (C. subcompressa) has the highest content of nobiletin (0.59%), a polymethoxylated flavone. LC-ES-MS anal. of Zanthoxylum genus for flavonoids revealed for the first time the presence of significant amts. (0.74%) of hesperidin in the root of Liangmianzhen (Z. nitidum (Roxb.) DC), a relative of Sichuan pepper, which is a spice widely used in China.

Abstract

Citrus flavonoids in fruit and traditional Chinese medicinal food ingredients in China. Lu, Yanhua; Zhang, Chongwei; Bucheli, Peter; Wei, Dongzhi. State Key Laboratory of Bioreactor Engineering, New World Institute of Biotechnology, East China University of Science and Technology, Shanghai, Peop. Rep. China. Plant Foods for Human Nutrition (New York, NY, United States) (2006), 61(2), 57-65. Publisher: Springer, CODEN: PFHNE8 ISSN: 0921-9668. Journal written in English. CAN 146:61367 AN 2006:700535 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. A review discusses the flavanones and dihydroflavonols that have been newly reported from 1992 to 2003. Abstract

Richmond, Surrey, UK. Editor(s): Andersen, Oeyvind M.; Markham, Kenneth R. Flavonoids (2006), 917-1002. Publisher: CRC Press LLC, Boca Raton, Fla CODEN: 69IHBV Conference; General Review written in English. CAN 146:291504 AN 2006:701546 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The structure of compd. I (R1-R5,R1'-R5'= H, methoxyl, or ethoxyl) for treating hepatitis B are presented. The compds. I are prepd. by extg. natural plants; and/or methylation or ethylation with di-Me sulfate or di-Et sulfate. Compd. I can be fisetin Me, baicalein Me, quercetin Me, morin Me, 7,8-dimethoxyflavone, tangeretin, naringenin Me, or flavanone.


Compounds for treating hepatitis B and its pharmaceutical composition. Lee, Lien-Tzu; Chang, Hsiu-Feng; Yeh, Chun-Pang. (The Industrial Technology Research Institute, Taiwan). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 19 pp. CODEN: CNXXEV CN 1796381 A 20060705 Patent written in Chinese. Application: CN 1010-4164 20041230. Priority: . CAN 145:167010 AN 2006:669526 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Naringenin is a naturally occurring citrus flavanone. In this study, the authors examd. the effect of naringenin on melanogenesis in mouse B16 melanoma cells. Melanin contents and tyrosinase activities were strongly increased by naringenin. Naringenin was found to cause marked increases in the expression levels of melanogenic enzymes.

Abstract

Stimulation of melanogenesis by the citrus flavonoid naringenin in mouse B16 melanoma cells. Ohguchi, Kenji; Akao, Yukihiro; Nozawa, Yoshinori. Gifu International Institute of Biotechnology, 1-1 Naka-Fudogaoka, Kakamigahara, Gifu, Japan. Bioscience, Biotechnology, and Biochemistry (2006), 70(6), 1499-1501. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 145:224470 AN 2006:671794 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


Preparation of benzopyrano[4,3-d][1,2,3]thiadiazoline derivatives as antitumor agents. Hu, Yongzhou; Ying, Huazhou; He, Qiaojun; Yang, Bo. (Zhejiang University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 27 pp. CODEN: CNXXEV CN 1793148 A 20060628 Patent written in Chinese. Application: CN 1009-7012 20051231. Priority: . CAN 145:249208 AN 2006:649948 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids are ubiquitous secondary plant metabolites which function as protectants against UV light and pathogens and are involved in the attraction of pollinators as well as seed and fruit dispersers. The hydroxylation pattern of the B-ring of flavonoids is detd. by the activity of two members of the vast and versatile cytochrome P 450 protein (P 450) family, the flavonoid 3'-hydroxylase (F3'H) and flavonoid 3',5'-hydroxylase (F3'5'H). Phylogenetic anal. of known sequences of F3'H and F3'5'H indicated that F3'5'H was recruited from F3'H before the divergence of angiosperms and gymnosperms. Seven cDNAs were isolated from species of the Asteraceae family, all of which were predicted to code for F3'Hs based on their sequences. The recombinant proteins of four of the heterologously in yeast expressed cDNAs exhibited the expected F3'H activity but surprisingly, three recombinant proteins showed F3'5'H activity. Phylogenetic analyses indicated the independent evolution of an Asteraceae-specific F3'5'H. Furthermore, sequence anal. of these unusual F3'5'H cDNAs revealed an elevated rate of nonsynonymous substitutions as typically found for duplicated genes acquiring new functions. Since F3'5'H is necessary for the synthesis of 3',4',5'-hydroxylated delphinidin-derivs., which normally provide the basis for purple to blue flower colors, the evolution of an Asteraceae-specific F3'5'H probably reflects the adaptive value of efficient attraction of insect pollinators.

Abstract

Cloning, functional identification and sequence analysis of flavonoid 3'-hydroxylase and flavonoid 3',5'-hydroxylase cDNAs reveals independent evolution of flavonoid 3',5'-hydroxylase in the Asteraceae family. Seitz, Christian; Eder, Christian; Deiml, Bettina; Kellner, Sandra; Martens, Stefan; Forkmann, Gert. Chair of Floriculture Crops and Horticultural Plant Breeding, Technical University Munich, Freising, Germany. Plant Molecular Biology (2006), 61(3), 365-381. Publisher: Springer, CODEN: PMBIDB ISSN: 0167-4412. Journal written in English. CAN 145:349420 AN 2006:667185 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

R1

R4

2

3

R

R R5

R' 2

R' 3

R' 4

R' 5

1R'

I


flavanone

Flavanone was synthesized through the Claisen-Schmidt condensation between benzaldehyde and acetophenone and subsequent intramol. Michael addn. over aminopropyl-functionalized SBA-15 materials. The catalysts with well-ordered hexagonally arranged mesopores were synthesized by one-pot co-condensation of tetraethoxysilane and aminopropyltriethoxysilane using amphiphilic block copolymer as the template under acidic condition. The results showed that the catalysts had good activities and very high selectivities to flavanone in solvent-free condition, while the use of org. solvents decreased the catalytic activities and flavanone selectivities. The influence of substituents in the arom. rings of benzaldehyde and 2'-hydroxyacetophenone was also investigated under the

Abstract

Solvent-free synthesis of flavanones over aminopropyl-functionalized SBA-15. Wang, Xueguang; Cheng, Soofin. Department of Chemistry, National Taiwan University, Taipei, Taiwan. Catalysis Communications (2006), 7(9), 689-695. Publisher: Elsevier B.V., CODEN: CCAOAC ISSN: 1566-7367. Journal written in English. CAN 146:316646 AN 2006:625429 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


S

NN

O

Cl

N

OEt

OEt

Cl

COCH 3H

S

NN

O

Cl

O

O

eM

R3

R2

1R

R4

R4

R1

R1

1R

R2

R2

R2

2R

III

The title benzopyrano[4,3-d][1,2,3]thiadiazoline derivs. I [wherein R1 = independently H, Cl, OMe, or Me; R2 = independently H, Cl, OMe, Me, or OCH2O; R3 = NO2, SO2Me, or NHC(=O)Me; R4 = Me, Et, Pr, or iso-Pr] were prepd. as antitumor agents (no data). For example, II was prepd. in a multi-step synthesis. II showed antitumor activity with IC50 of 1.59 μg/mL against PC-3 human prostatic tumor cell.

Abstract CN 2005-10097012 20051231Priority Application CN 1793148 A 20060628 CN 2005-10097012 20051231 Patent No. Kind Date Application No. Date


flavanone

Background: Silibinin, a flavanone from milk thistle, inhibits the growth of tumors in several rodent models. We examd. the effects of dietary silibinin on the growth, progression, and angiogenesis of urethane-induced lung tumors in mice. Methods: A/J mice (15 per group) were injected with urethane (1 mg/g body wt.) or saline alone and fed normal diets for 2 wk, after which they were fed diets contg. different doses of silibinin (0%-1% [wt/wt] silibinin) for 18 or 27 wk. Immunohistochem. and Western blot anal. were used to examine angiogenesis and enzymic markers of inflammation, proliferation, and apoptosis. All statistical tests were two-sided. Results: Urethane-injected mice exposed to silibinin had statistically significantly lower lung tumor multiplicities than urethane-injected mice fed the control diet lacking silibinin (i.e., control mice). Mice that received urethane and 1% (wt/wt) dietary silibinin for 18 wk had 93% fewer large (i.e., 1.5-2.5-mm-diam.) lung tumors than control mice (mean no. of tumors/mouse: 27 in the urethane group vs. 2 in the urethane + 1% silibinin group, difference = 25 tumors/mouse, 95% confidence interval [CI] = 13 to 37 tumors/mouse, P = .005). Lung tumors of silibinin-fed mice had 41%-74% fewer cells pos. for the cell proliferation markers proliferating cell nuclear antigen and cyclin D1 than lung tumors of control mice. Tumor microvessel d. was reduced by up to 89% with silibinin treatment (e.g., 56 microvessels/400× field in tumors from control mice vs. 6 microvessels/400× field in tumors from urethane + 1% silibinin-treated mice [difference = 50 microvessels/400× field, 95% CI = 46 to 54 microvessels/400× field; P<.001]). Silibinin decreased lung tumor expression of vascular

Abstract

Effect of Silibinin on the Growth and Progression of Primary Lung Tumors in Mice. Singh, Rana P.; Deep, Gagan; Chittezhath, Manesh; Kaur, Manjinder; Dwyer-Nield, Lori D.; Malkinson, Alvin M.; Agarwal, Rajesh. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Sciences Center, Denver, CO, USA. Journal of the National Cancer Institute (2006), 98(12), 846-855. Publisher: Oxford University Press, CODEN: JNCIEQ ISSN: 0027-8874. Journal written in English. CAN 146:19508 AN 2006:621740 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Both title compds. show two fluorescence bands, with maxima at approx. 290 nm and 340 nm in non-protic (hexane, cyclohexane) and protic (ethanol) solvents. Approx. MO calcns. suggest that these two bands can be assocd. with an excitation partially localized on the anisolyl moiety and a more delocalized excitation, resp., present in both compds. In cyclohexane both compds. exhibit a fluorescence band with a max. at 550 nm, which can be assocd. with the proton transferred species. In the case of the flavanone this band is very weak and attributed to Excited State Intramol. Proton Transfer (ESIPT) of the proton at the 5-position. In the flavone the corresponding band is considerably more intense and the theor. calcns. point to the proton being transferred as originating from the 5-position also. In cyclohexane the flavanone exhibits monoexponential decay under the band at 290 nm. In all other combinations solute/solvent/band studied here the fluorescence was found to follow a biexponential decay. In the case of the flavanone these results are interpreted as indicating that the localized anisolyl excitation is not coupled to the delocalized excitation, whereas the decay of the latter is coupled to ESIPT. The time-resolved results of the flavone are interpreted as indicating coupling between all three excited states obsd.

Abstract

Excited state acidity of bifunctional compounds 9. Excited state intramolecular proton transfer in 3,5-dihydroxy-7,4'-dimethoxyflavone and 3,5-dihydroxy-7,4'-dimethoxyflavanone: spectral and fluorescence decay results. Portugal, Samira G. M.; Montero-Cabrera, Luis A.; Diaz, Lourdes A.; Brinn, Ira M. Laboratorio de Espectroscopia Resolvida no Tempo (LERT), Instituto de Quimica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil. Journal of Photochemistry and Photobiology, A: Chemistry (2006), 181(2-3), 370-377. Publisher: Elsevier B.V., CODEN: JPPCEJ ISSN: 1010-6030. Journal written in English. CAN 146:261849 AN 2006:622086 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


solvent-free condition.


flavanone

A study of the structure-activity relations of the inhibitory effect of flavonoids on lipopolysaccharide (LPS)-induced prostaglandin Abstract

Structure-activity relations of inhibitory effects of various flavonoids on lipopolysaccharide-induced prostaglandin E2 production in rat peritoneal macrophages: comparison between subclasses of flavonoids. Takano-Ishikawa, Y.; Goto, M.; Yamaki, K. National Food Research Institute, Kannondai, Tsukuba, Ibaraki, Japan. Phytomedicine (2006), 13(5), 310-317. Publisher: Elsevier GmbH, CODEN: PYTOEY ISSN: 0944-7113. Journal written in English. CAN 145:448573 AN 2006:616708 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

MeMe

O

OOH

OHH

H

eM

I

A new geranyl flavanone, 2'-hydroxy-macarangaflavone A (I), and a known 4',7-dihydroxy-8-methylflavan were isolated from the leaves of Macaranga triloba (Euphorbiceae). The structure of I was elucidated based on spectroscopic methods, including 1D and 2D NMR anal.

Abstract

A new geranyl flavanone from Macaranga triloba. Dinh, Vinh; Zhang, Hua-Ping; Duc, Nguyen Minh; Tuu, Nguyen Viet; Qin, Guo-Wei. Faculty of Pharmacy, Ho Chi Minh City College of Pharmacy and Medicine, Ho ChiMinh City, Vietnam. Journal of Asian Natural Products Research (2005), Volume Date 2006, 8(1-2), 155-158. Publisher: Taylor & Francis Ltd., CODEN: JANRFI ISSN: 1028-6020. Journal written in English. CAN 146:418312 AN 2006:616750 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Conclusions: Silibinin inhibits lung tumor angiogenesis in an animal model and merits investigation as a chemopreventive agent for suppressing lung cancer progression.

endothelial growth factor (VEGF) and of inducible nitric oxide synthase and cyclooxygenase-2, two enzymes that promote lung tumor growth and progression by inducing VEGF expression.


flavanone

Propolis is produced by bees and is reported to have several pharmaceutical properties. Its antibacterial activity against strains causing upper respiratory tract infections is particularly important: propolis might be used as a therapeutic agent to prevent the bacterial infections that sometimes overlap viral infections. In this study the in vitro activity of both an alc. soln. and a hydroglyceric ext. of propolis, as well as its active principles, was tested against bacteria responsible for respiratory infections (Streptococcus pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis and Streptococcus pyogenes). We also evaluated the in vitro activity of a combination of propolis and its active principles and some beta-lactams, macrolides and

Abstract

Antibacterial activity of propolis and its active principles alone and in combination with macrolides, beta-lactams and fluoroquinolones against microorganisms responsible for respiratory infections. Speciale, A.; Costanzo, R.; Puglisi, S.; Musumeci, R.; Catania, M. R.; Caccamo, F.; Iauk, L. Department of Microbiological and Gynecological Sciences, University of Catania, Italy. Journal of Chemotherapy (Firenze, Italy) (2006), 18(2), 164-171. Publisher: E.S.I.F.T. srl, CODEN: JCHEEU ISSN: 1120-009X. Journal written in English. CAN 146:96648 AN 2006:581258 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanone 3-hydroxylase (F3H) activity is necessary for the biosynthesis of flavonoids, the main ingredients of Gingko biloba ext. The full-length cDNA and genomic DNA sequences of F3H gene were isolated from G. biloba for the first time. The full-length cDNA of G. biloba F3H gene (designated as GbF3H) contained a 1071-bp open reading frame (ORF) encoding a 357-amino-acid protein with a calcd. mol. wt. of about 40 kDa and isoelec. point (pI) of 5.57. Genomic DNA anal. showed that GbF3H gene has 3 exons and 2 introns. The deduced GbF3H protein showed high identities to other plant F3Hs. The conserved amino acids ligating ferrous iron and residues participating in 2-oxoglutarate binding (R-X-S) were found in GbF3H at the similar positions like other F3Hs. Three-dimensional structure modeling showed that GbF3H had a jerry roll in the enzyme core consisted of β-sheet, a typical structure shared by all 2-oxoglutarate-dependent dioxygenases including F3Hs. Phylogenetic tree anal. revealed that GbF3H shared the same ancestor in evolution with other F3Hs and had a further relationship with other angiosperms species. Southern blot anal. indicated that GbF3H belonged to a multi-gene family. Transcription anal. revealed that GbF3H expressed in stem and leaf with the highest transcription level in leaf. The isolation and characterization of GbF3H gene will be helpful to further study the role of GbF3H gene in the biosynthesis of flavonoids in G. biloba.

Abstract

Cloning and characterization of a flavanone 3-hydroxylase gene from Ginkgo biloba. Shen, Guoan; Pang, Yongzhen; Wu, Weisheng; Deng, Zhongxiang; Zhao, Lingxia; Cao, Youfang; Sun, Xiaofen; Tang, Kexuan. Shanghai Key Laboratory of Biotechnology, Plant Biotechnology Research Center, Fudan-SJTU-Nottingham Plant Biotechnology R&D Center, School of Agriculture and Biology, Shanghai Jiao Tong University, Shanghai, Peop. Rep. China. Bioscience Reports (2006), 26(1), 19-29. Publisher: Springer, CODEN: BRPTDT ISSN: 0144-8463. Journal written in English. CAN 145:242592 AN 2006:587712 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


prodn. was carried out via a comparative examn. of 39 flavonoids and related compds. A comparison of the subclasses showed that flavones were most effective, followed by flavanones. Flavonols were less effective than those two groups. These results suggest that the C2-C3 double-bond and 4-oxo functional group of the C-ring are important factors for the high inhibition activities. Flavonoids showed the strongest inhibitory effect on the expression of Cox-2 protein. These results help to explain part of the reason for the pharmacol. efficacy of flavonoids as anti-inflammatory compds.


flavanone

Abstract

Synthesis and immunosuppressive activity of L-rhamnopyranosyl flavonoids. Yang, Xiaoliang; Sun, Yang; Xu, Qiang; Guo, Zijian. Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, Peop. Rep. China. Organic & Biomolecular Chemistry (2006), 4(12), 2483-2491. Publisher: Royal Society of Chemistry, CODEN: OBCRAK ISSN: 1477-0520. Journal written in English. CAN 145:230804 AN 2006:549053 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A fast and automated chiral sepn. screening platform was developed, allowing the parallel and simultaneous testing of eight different chiral columns with a broad variety of mobile phases within a short period of time. In particular for preparative applications, this approach considerably accelerates the method development of chiral sepns., leading to a significant gain of time and productivity.

Abstract

Multi-parallel chiral screening: screening of chiral stationary and mobile phases for method development of preparative separations. Francotte, Eric; Huynh, Dan; Wetli, Herbert A. Discovery Technologies, Novartis Institutes for BioMedical Research, Basel, Switz. G.I.T. Laboratory Journal, Europe (2006), 10(3), 46-48. Publisher: GIT Verlag GmbH & Co. KG, CODEN: GLJEAW ISSN: 1611-6038. Journal written in English. CAN 146:213033 AN 2006:551088 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new flavanone Persinol (1) and the new flavanone glucosides persinosides A (2) and B (3), along with known flavonoids (4 and 5) have been isolated from the Et acetate sol. fraction of the whole plants of Aerva persica. Their structures were elucidated on the basis of extensive anal. of NMR (1D & 2D-NMR) spectral data. All of them showed profound antioxidative activities by DPPH and cytochrome-c-redn. assays using the HL-60 cell culture system.

Abstract

Antioxidant activity with flavonoidal constituents from Aerva persica. Ahmed, Ejaz; Imran, Muhammad; Malik, Abdul; Ashraf, Muhammad. International Center for Chemical Sciences, H.E.J. Research Institute of Chemistry, University of Karachi, Karachi, Pak. Archives of Pharmacal Research (2006), 29(5), 343-347. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 145:285019 AN 2006:559973 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


fluoroquinolones. Our results, though not demonstrating a clearly synergistic activity between antibiotics and propolis and its constituents, show the possibility of using natural prepns., due to their antimicrobial and anti-inflammatory properties, to enhance antibacterial therapy.


flavanone

Polyphenolic compds. are widely distributed in the vegetable kingdom and are therefore consumed regularly in the human diet. Epidemiol. studies suggest that foods rich in polyphenolic compds. contribute to reducing the risk of cancer. We study the possible cytotoxicity and antiproliferative effects in vitro of twelve phenolic compds. on three cell lines of melanocytes, two of melanoma (B16F10 and SK-MEL-1) and one of non-transformed melanocytes (Melan-a) and identify the possible relationship between the chem.

Abstract

Antiproliferative activity of several phenolic compounds against melanoma cell lines: relationship between structure and activity. Benavente-Garcia, Obdulio; Castillo, J.; Lorente, J.; Alcaraz, M.; Yanez, J.; Martinez, C.; Vicente, V.; Lozano, J. A. Research and Development Department, Nutrafur-Furfural Espanol S.A. Camino Viejo de Pliego, Murcia, Spain. Agro Food Industry Hi-Tech (2005), 16(4), 30-34. Publisher: Tekno Scienze srl, CODEN: AIHTEI ISSN: 1722-6996. Journal written in English. CAN 145:388692 AN 2006:543301 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The radioprotective effects of hesperidin (HES), a flavanone glucoside, were investigated by using the micronucleus test for anticlastogenic and cell proliferation activity. A single i.p. (i.p.) administration of hesperidin at doses of 10 mg kg-1, 20 mg kg-1, 40 mg kg-1, 80 mg kg-1 and 160 mg kg-1 45 min prior to gamma irradn. (2 Gy) reduced the frequencies of micronuleated polychromatic erythrocytes (MnPCEs). All five doses of HES significantly reduced the frequencies of MnPCEs and increased PCE/PCE+NCE ratio in mice bone marrow compared with non-drug-treated irradiated control (p<0.0001). There was a drug dose-response effect of HES in reducing MnPCE and increasing the PCE/PCE+NCE ratio in bone marrow cells. The max. redn. in MnPCE was obsd. in mice treated with HES at a dose of 80 mg kg-1. The total MnPCE values were 2.85 fold less in the 80 mg kg-1 HES group after being exposed to 2 Gy of γ-rays than those in the resp. irradiated control. Our study demonstrates that hesperidin has powerful protective effects on the radiation-induced DNA damage and on the decline in cell proliferation in mouse bone marrow.

Abstract

Radioprotective effects of hesperidin against gamma irradiation in mouse bone marrow cells. Hosseinimehr, S. J.; Nemati, A. Department of Medicinal Chemistry, Faculty of Pharmacy, Mazandarn University Medical Sciences, Sari, Iran. British Journal of Radiology (2006), 79(941), 415-418. Publisher: British Institute of Radiology, CODEN: BJRAAP ISSN: 0007-1285. Journal written in English. CAN 145:78827 AN 2006:544318 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Astilbin, a flavonoid isolated from different plants, shows diverse biol. activities. Synthesis and immunosuppressive activity of seven analogs of astilbin are reported, which may shed light on the structure-activity relationship of the compds. The following glycosyl flavonoids, 6-α-L-rhamnopyranosyloxyflavanone (I), 3-α-L-rhamnopyranosyloxyflavone (II), 3-α-l-rhamnopyranosyloxyflavanone (III), 3-α-L-rhamnopyranosyloxychromanone (IV), 4-α-L-rhamnopyranosyloxychromanol (V), 7-hydroxy-3-α-L-rhamnopyranosyloxyflavanone (VI) and 4'-hydroxy-3-α-L-rhamnopyranosyloxyflavanone (VII) were prepd. resp. by glycosylation of 6-hydroxyflavanone, 3-hydroxyflavone, 3-hydroxyflavanone, 3-hydroxychromanone, 4-chromanol, 7-benzyloxy-3-hydroxyflavanone, 4'-benzyloxy-3-hydroxyflavanone. Similar to astilbin, II, III, IV, VI and VII significantly inhibited the single mixed lymphocytes reaction (sMLR) and enhanced the apoptosis of spleen cells isolated from mice with sheep red blood cell-induced delayed-type hypersensitivity resp. However, I only showed a slight tendency to inhibit sMLR at higher concn. Both compds. I and V did not influence the cell apoptosis. These data suggest that the position at which the sugar is linked to the flavone and the presence of carbonyl on C-4 and phenol hydroxyl group in A or B ring play essential roles in detg. the biol. activity of the flavonoids. However, the presence of a B ring is unfavorable for the biol. activity and the double bond at C(2)-C(3) in C-ring shows little effect on the activity.


flavanone


A review. The development of a hair growth stimulant trans-3,4'-Dimethyl-3-hydroxyflavanone (t-flavanone) by modification of a hair growth-stimulating component in Hypericum perforatum ext. (astilbin), and the clin. trials of t-flavanone in male patients with alopecia are discussed in this article.

Abstract

Effect of t-flavanone on hair growth. Hotta, Mitsuyuki; Imokawa, Genji. Lab. of Biosciences, Kao Corp., Japan. Anchi - Eijingu Shirizu (2005), 1(Shiraga, Datsumo, Ikumo no Jissai), 105-116. Publisher: Enu - Ti - Esu, CODEN: AESNBO Journal; General Review written in Japanese. CAN 146:189863 AN 2006:529276 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


2-Oxoglutarate-dependent dioxygenases (2-ODDs) catalyze numerous steps in biosynthetic pathways of plants. Prohexadione-Ca is a known inhibitor of such reactions, due to its structural similarity to 2-oxoglutarate. In apple (Malus domestica) and pear (Pyrus communis) leaves, the transient inhibition of 2-ODDs flavanone 3β-hydroxylase (FHT) and flavonol synthase (FLS) by prohexadione-Ca results in distinct changes in the flavonoid spectrum, which are responsible for an enhanced resistance against two major pome fruit diseases, fire blight (caused by Erwinia amylovora) and apple scab (caused by Venturia inaequalis). We used recombinant apple and pear FHT and apple FLS for screening 23 structural analogs of 2-oxoglutarate, mostly cyclohexanediones, pyridine dicarboxylic acids and N-heterocycles with carbonyl functions for other dioxygenase inhibitors. Activations, which were also obsd. for some compds., are interpreted as in vitro effects due to Fe2+-chelating ability. Apart from structural similarity to 2-oxoglutarate, close structural similarity of cyclohexanediones and some pyridine dicarboxylic acids to flavonoid substrates was identified. Beyond the competitive inhibition for the co-substrate 2-oxoglutarate, flavonoid converting 2-ODDs may also be inhibited at the substrate binding site by these inhibitors. All compds. found to be active as inhibitors may prove useful for studying the reaction mechanisms and substrate specificities of various 2-ODDs.

Abstract

Screening for inhibitors of 2-oxoglutarate-dependent dioxygenases: Flavanone 3β-hydroxylase and flavonol synthase. Halbwirth, Heidrun; Fischer, Thilo C.; Schlangen, Karin; Rademacher, Wilhelm; Schleifer, Klaus-Juergen; Forkmann, Gert; Stich, Karl. Institut fuer Verfahrenstechnik, Umwelttechnik und Technische Biowissenschaften, Technische Universitaet Wien, Vienna, Austria. Plant Science (Amsterdam, Netherlands) (2006), 171(2), 194-205. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 146:138928 AN 2006:539146 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


structure of the tested compds. and their effect on cellular viability. The said phenolic compds. corresponded to eight flavonoids with varying hydroxyl and methoxyl substituents, related structurally through the oxidn. state of their flavonoid skeleton, and four phenolic acids. The cytotoxic activity of all the studied compds. was modest or not apparent. The flavonoids, luteolin, tangeretin, baicalein, quercetin and myricetin, and gallic acid showed antiproliferative effects on the tested lines. Our results suggest that a correlation exists between the structural oxidn. state and the position, no. and nature of substituents of the polyphenolic compds. studied and their antiproliferative effects.


flavanone

Harungana madagascariensis is well known for its topical antibacterial properties used in the elaboration of a lot of skin hygiene Abstract

Isolation and in vitro antibacterial activity of astilbin, the bioactive flavanone from the leaves of Harungana madagascariensis Lam. ex Poir. (Hypericaceae). Moulari, B.; Pellequer, Y.; Lboutounne, H.; Girard, C.; Chaumont, J.-P.; Millet, J.; Muyard, F. Laboratoire de Galenique et Biopharmacie, EA-3924 Sciences Separatives et Biopharmaceutiques, UFR Sciences Medicales et Pharmaceutiques, Universite de Franche-Comte, Besancon, Fr. Journal of Ethnopharmacology (2006), 106(2), 272-278. Publisher: Elsevier B.V., CODEN: JOETD7 ISSN: 0378-8741. Journal written in English. CAN 146:117912 AN 2006:517871 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The pharmacol. effects on the central nervous system (CNS) of a range of available flavonoid glycosides were explored and compared to those of the glycosides 2S-hesperidin and linarin, recently isolated from valeriana. The glycosides 2S-neohesperidin, 2S-naringin, diosmin, gossypin and rutin exerted a depressant action on the CNS of mice following i.p. injection, similar to that found with 2S-hesperidin and linarin. We demonstrate in this work that these behavioral actions, as measured in the hole board, thiopental induced sleeping time and locomotor activity tests, are unlikely to involve a direct action on γ-aminobutyric acid type A (GABAA) receptors. The corresponding aglycons were inactive, pointing to the importance of the sugar moieties in the glycosides in their CNS depressant action following systemic administration. The pharmacol. properties of the flavonoid glycosides studied here, in addn. to our previous results with hesperidin and linarin, opens a promising new avenue of research in the field.

Abstract

Central nervous system depressant action of flavonoid glycosides. Fernandez, Sebastian P.; Wasowski, Cristina; Loscalzo, Leonardo M.; Granger, Renee E.; Johnston, Graham A. R.; Paladini, Alejandro C.; Marder, Mariel. Instituto de Quimica y Fisicoquimica Biologicas, Facultad de Farmacia y Bioquimica, Buenos Aires, Argent. European Journal of Pharmacology (2006), 539(3), 168-176. Publisher: Elsevier B.V., CODEN: EJPHAZ ISSN: 0014-2999. Journal written in English. CAN 145:159619 AN 2006:517935 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The isolation and structure elucidation of glycosides in n- butanol exts. from rhizome of Periploca calophylla were studied. The chem. constituents from n-butanol exts. of Periploca calophylla were isolated and purified by chromatog. technol. and their structures were elucidated on the basis of physicochem. property and spectroscopic methods. Eight glycosides were isolated and identified as periplocin, kaempferol 3-α-D-arabinoside, kaempferol 3-O-β-D-glucoside, 3',4',5,7-tetrahydroxy-flavanone-2(S)-3'-O-β-D-glucopyranoside, (+)-syringaresinol-4'-O-β-D-monoglucoside, 1-sinapoylglucoside, erigeside C, 2,6-dimethoxy-4-hydroxyphenol 1-O-β-D-glucoside. All the compds. were isolated first time from Periploca calophylla Falc.

Abstract

Isolation and structure elucidation of glycosides in n-butanol extracts from rhizome of Periploca calophylla. Guo, Hongli; Zhou, Jinyun. Institute of Materia Medica, Chinese Academy of Medical Sciences + Peking Union Medical College, Beijing, Peop. Rep. China. Zhongguo Zhongyao Zazhi (2005), 30(1), 44-46. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese. CAN 146:224710 AN 2006:526030 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Naringenin is a naturally occurring citrus flavanone, which has been reported to have a wide range of pharmacol. properties. The present work was carried out to evaluate the effect of naringenin on antioxidant and lipid peroxidn. status in the liver of oxytetracycline-intoxicated rats. Intraperitonial administration of oxytetracycline 200 mg/kg for 15 days resulted in a significant elevation in serum hepatospecific markers such as aspartate transaminase, alanine transaminase, alk. phosphatase, lactate dehydrogenase, and bilirubin and the levels of lipid peroxidn. markers [thiobarbituric acid-reactive substances (TBARS) and lipid hydroperoxides] in liver. Oxytetracycline also caused a significant redn. in the activities of superoxide dismutase, catalase, glutathione peroxidase, reduced glutathione (GSH), vitamin C, and vitamin E in liver. Oral administration of naringenin (50 mg/kg b.w.t.) with oxytetracycline significantly decreased the activities of serum aspartate transaminase, alanine transaminase, alk.

Abstract

Influence of naringenin on oxytetracycline mediated oxidative damage in rat liver. Pari, Leelavinothan; Gnanasoundari, Muthurangam. Department of Biochemistry, Faculty of Science, Annamalai University, Annamalainagar, India. Basic & Clinical Pharmacology & Toxicology (2006), 98(5), 456-461. Publisher: Blackwell Publishing Ltd., CODEN: BCPTBO ISSN: 1742-7835. Journal written in English. CAN 145:159131 AN 2006:508887 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(2S)-Flavanones (naringenin and pinocembrin) are key intermediates in the flavonoid biosynthetic pathway in plants. Recombinant Escherichia coli cells contg. four genes for a phenylalanine ammonia-lyase, cinnamate/coumarate:CoA ligase, chalcone synthase, and chalcone isomerase, in addn. to the acetyl-CoA carboxylase, have been established for efficient prodn. of naringenin from tyrosine and pinocembrin from phenylalanine. Further introduction of the flavone synthase I gene from Petroselinum crispum under the control of the T7 promoter and the synthetic ribosome-binding sequence in pACYCDuet-1 caused the E. coli cells to produce flavones: apigenin (13 mg/l) from tyrosine and chrysin (9.4 mg/l) from phenylalanine. Introduction into the E. coli cells of the flavanone 3β-hydroxylase and flavonol synthase genes from the plant Citrus species led to prodn. of flavonols: kaempferol (15.1 mg/l) from tyrosine and galangin (1.1 mg/l) from phenylalanine. The combinatorial biosynthesis of the flavones and flavonols in E. coli is promising for the construction of a library of various flavonoid compds. and un-natural flavonoids in bacteria.

Abstract

Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Miyahisa, Ikuo; Funa, Nobutaka; Ohnishi, Yasuo; Martens, Stefan; Moriguchi, Takaya; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan. Applied Microbiology and Biotechnology (2006), 71(1), 53-58. Publisher: Springer, CODEN: AMBIDG ISSN: 0175-7598. Journal written in English. CAN 145:247558 AN 2006:511679 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


products. The aim of this study was, on the one hand, to evaluate the in vitro antibacterial activities of aq., ethanolic and Et acetate crude exts. of Harungana madagascariensis leaves against bacterial strains representative of skin microflora and, on the other hand, to det. the chem. structure of the active compd. Only the Et acetate leaf ext. presented important antibacterial activity. Its fractionation was carried out by column chromatog. using silica gel 60 and it yielded 11 fractions. A bioautog. method, revealed in these fractions the presence of a flavanone as the active compd. astilbin or 3-O-α-L-rhamnoside-5,7,3',4'-tetrahydroxydihydroflavonol which was identified on the basis of its spectroscopic data. Concerning the antibacterial activity against the representative skin microflora of the armpit and feet, MIC and MBC ranged from 25 to 250 and 100 to 750 μg ml-1, resp. The results showed that some bacteria considered to be responsible for bad odours at the armpit and feet levels, were destroyed at 200 μg ml-1 (MBC), a concn. sparing most of the useful saprophytic microflora. The minimal inhibitory quantity (MIQs) of astilbin ranged from 50 to 100 μg.


flavanone

Use of ecotilling as an efficient SNP discovery tool to survey genetic variation in wild populations of Populus trichocarpa. Bibliographic Information Answer 425:

A review. In 1998 the domestic market for hair growth agent was about 30 billion yen in Japan. The market's growth spurt was set off by the launch of RiUP, which is a hair growth stimulant hit shelves in 1999. The market has been sliding down since its peak of 60 billion yen. The recent market research ests. that more than 8 million men in Japan suffer some degree of hair loss. Industry sources est. the size of the market will grow again due to the marketing of powerful products, such as Propecia, which was launched in Dec. 2005 as the first oral medication for androgenic alopecia. Accordingly, a great amt. of R&D effort in cosmetic, pharmaceutical, and bio-venture industries centers on developing a hair growth agent with higher efficacy. This paper aims to outline the mechanism of action of chief ingredients for hair growth agents on the market, and to explain the mechanism and efficacy of t-flavanone with detailed information.

Abstract

Effect of t-flavanone on hair growth. Moriwaki, Shigeru. Biological Science Laboratories, Kao Corporation, Haga, Tochigi, Japan. Nippon Koshohin Gakkaishi (2006), 30(1), 23-28. Publisher: Nippon Koshohin Gakkai, CODEN: NKGIBW ISSN: 1880-2532. Journal; General Review written in Japanese. CAN 145:459902 AN 2006:505547 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The quant. relationship between structures and cytotoxicities of 33 flavone derivs. against HIV was studied. 14 Quantum-chem. descriptors were calcd. at B3LYP/6- 31G** level. A total of 5 important descriptors was selected by stepwise regression anal. (SRA). These descriptors were: energy of the lowest occupied mol. orbit (ELUMO), mol. hardness (η), mol. polarizalsility (α), mol. dipole moment (μ), and net charge on the seventh C atom (Q7). A leave-one-out cross-validation method was used to select the no. of latent variables for the building of the QSAR models by principal component regression (PCR) and partial least square regression (PLS) method. resp. The cross-validation squared correlation coeffs. Rcv2 were 0.70 for PCR and 0.74 for PLS, showing that both of these two models had good prediction ability and the PLS model was superior to the PCR model. The QSAR model shows the effects of the five descriptors, and directs the research of the flavonoids with low toxicity.

Abstract

Relationship between structures and cytotoxicities of flavone derivatives against HIV with quantum-chemical descriptors. Du, Juan; Li, Zerong; Li, Xiangyuan; Yang, Shengyong. College of Chemical Engineering, Sichuan University, Sichuan, Peop. Rep. China. Huaxi Yaoxue Zazhi (2005), 20(2), 95-98. Publisher: Huaxi Yike Daxue Yaoxueyuan, CODEN: HYZAE2 ISSN: 1006-0103. Journal written in Chinese. CAN 145:409998 AN 2006:505724 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


phosphatase, lactate dehydrogenase, and the levels of bilirubin along with a significant decrease in the levels of lipid peroxidn. markers in the liver. In addn., naringenin significantly increased the activities of superoxide dismutase, catalase, and GSH peroxidase as well as the level of GSH, vitamin C, and vitamin E in the liver of the oxytetracycline-treated rats. Thus, naringenin exhibited an antioxidant property and decreased the lipid peroxidn. against oxytetracycline-induced oxidative stress in the liver.


flavanone

PT RO SE SI SK TRR: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, LV, MC, NL, PL,

EP 1912632 A2 20080423 EP 2006-774176 20060628



WO 2007005453 A3 20070614WO 2007005453 A2 20070111 WO 2006-US25138 20060628CA 2613636 A1 20070111 CA 2006-2613636 20060628AU 2006266125 A1 20070111 AU 2006-266125 20060628US 20050171027 A1 20050804 US 2004-27779 20041229US 20060111435 A1 20060525 US 2005-174000 20050701Patent No. Kind Date Application No. Date Patent Family Information

Methods and compositions using sirtuin modulators for treating or preventing obesity and insulin resistance disorders. Sinclair, David A.; Alexander-Bridges, Maria. (President and Fellows of Harvard College, USA; The General Hospital Corporation). U.S. Pat. Appl. Publ. (2006), 154 pp., Cont.-in-part of U.S. Ser. No. 27,779. CODEN: USXXCO US 2006111435 A1 20060525 Patent written in English. Application: US 2005-174000 20050701. Priority: US 2003-533712 20031229; US 2004-588643 20040716; US 2004-27779 20041229. CAN 145:1047 AN 2006:491764 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Ecotilling was used as a simple nucleotide polymorphism (SNP) discovery tool to examine DNA variation in natural populations of the western black cottonwood, Populus trichocarpa, and was found to be more efficient than sequencing for large-scale studies of genetic variation in this tree. A publicly available, live ref. collection of P. trichocarpa from the University of British Columbia Botanical Garden was used in this study to survey variation in nine different genes among individuals from 41 different populations. A large amt. of genetic variation was detected, but the level of variation appears to be less than in the related species, Populus tremula, based on reported statistics for that tree. Genes examd. varied considerably in their level of variation, from PoptrTB1 which had a single SNP, to PoptrLFY which had more than 23 in the 1000-bp region examd. Overall nucleotide diversity, measured as πTotal, was relatively low at 0.00184. Linkage disequil., on the other hand, was higher than reported for some woody plant species, with mean R2 equal to 0.34. This study reveals the potential of Ecotilling as a rapid genotype discovery method to explore and utilize the large pool of genetic variation in tree species.

Abstract

Gilchrist, Erin J.; Haughn, George W.; Ying, Cheng C.; Otto, Sarah P.; Zhuang, Jun; Cheung, Dorothy; Hamberger, Bjorn; Aboutorabi, Fariba; Kalynyak, Tatyana; Johnson, Lee; Bohlmann, Joerg; Ellis, Brian E.; Douglas, Carl J.; Cronk, Quentin C. B. Department of Botany, University of British Columbia, Vancouver, BC, Can. Molecular Ecology (2006), 15(5), 1367-1378. Publisher: Blackwell Publishing Ltd., CODEN: MOECEO ISSN: 0962-1083. Journal written in English. CAN 146:39536 AN 2006:498630 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Flavonones in grapefruit, lemons, and limes: A compilation and review of the data from the analytical literature. Peterson, Julia J.; Beecher, Gary R.; Bhagwat, Seema A.; Dwyer, Johanna T.; Gebhardt, Susan E.; Haytowitz, David B.; Holden, Joanne M. Tufts University Friedman School of Nutrition Science & Policy, Boston, MA, USA. Journal of Food Composition and Analysis (2006), 19(Suppl.), S74-S80. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575. Journal; General Review written in English.


Title inhibitors contain dorsmanin A, xanthoangelol I, J, xanthotoxin, isopimpinellin, osthenol, isobavachin, mundulea flavanone B, 8-geranylnaringenin, and/or (11S,16R)-dihydroxyoctadeca-9Z,17-diene-12,14-diyn-1-yl acetate. They may be added to foods, beverages, and feeds. Thus, xanthoangelol I and J completely inhibited TPA-induced expression of Epstein-Barr virus early antigen in Raji cells with their survival rate 70%, vs. 60%, for curcumin.


Carcinogenesis inhibitors containing natural chalcones, coumarins, flavanones, and/or diacetylene derivative. Akihisa, Toshihiro; Tokuda, Harukuni; Ukiya, Motohiko; Hasegawa, Daisuke. (Nihon University, Japan). Jpn. Kokai Tokkyo Koho (2006), 14 pp. CODEN: JKXXAF JP 2006131594 A 20060525 Patent written in Japanese. Application: JP 2004-325369 20041109. Priority: . CAN 144:481031 AN 2006:489728 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention provides methods and compns. for modulating the activity or level of a sirtuin, thereby treating or preventing obesity or an insulin resistance disorder, e.g. diabetes, in a subject. Exemplary methods comprise contacting a cell with a sirtuin activating compd. or an inhibitory compd. to thereby increase or decrease fat accumulation, resp.

Abstract WO 2006-US25138 W 20060628US 2005-174000 A 20050701US 2004-27779 A2 20041229US 2004-588643P P 20040716US 2003-533712P P 20031229Priority Application


flavanone

From the roots of Scutellaria amabilis, eleven new flavonoids, 5,7,2'-trihydroxy-8-methoxyflavone 7-O-β-D-glucopyranoside, 5,7,2'-trihydroxy-8-methoxyflavone 2'-O-β-D-glucopyranoside, 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-β-D-glucopyranoside, 5,7,2'-trihydroxyflavone 2'-O-β-D-glucopyranoside, 5,7,2',5'-tetrahydroxyflavone 7-O-β-D-glucuronopyranoside,

Abstract

Studies on the constituents of Scutellaria species (XXII). Constituents of the roots of Scutellaria amabilis Hara. Miyaichi, Yukinori; Hanamitsu, Eiji; Kizu, Haruhisa; Tomimori, Tsuyoshi. Department of Pharmacognosy, Pharmaceutical Sciences, Hokuriku University, Ho-3, Kanagawa-machi, Kanazawa, Ishikawa, Japan. Chemical & Pharmaceutical Bulletin (2006), 54(4), 435-441. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 145:141189 AN 2006:477205 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Flavanones constitute the majority of flavonoids in citrus fruits such as sweet (Citrus sinensis) and sour oranges (C. aurantium) and their near relatives-tangerines/mandarins (C. reticulata), tangors and tangelos. The relevant chem. analytic literature was searched, abstracted, documented, standardized, examd. for quality, enumerated, and summarized in a database for these citrus flavanones: hesperidin, naringin, narirutin, eriocitrin, neohesperidin, didymin, neoeriocitrin, and poncirin. Sour oranges had a distinct flavanone profile dominated by naringin and neohesperidin, and were highest in total flavanones (summed means) (48 mg/100 g aglycons). Total flavanones (summed means) in sweet oranges, tangerines, and tangors were similar (.apprx.20 mg/100 g), and hesperidin and narirutin dominated the flavanone profiles for these three fruits. Total flavanones (summed means) in tangelos (30 mg/100) were midway between sour and sweet oranges and the tangelo flavanone profile exhibited characteristics of both species. The database provides information on several varieties of citrus and eight flavanone compds.

Abstract

Flavanones in oranges, tangerines (mandarins), tangors, and tangelos: a compilation and review of the data from the analytical literature. Peterson, Julia J.; Dwyer, Johanna T.; Beecher, Gary R.; Bhagwat, Seema A.; Gebhardt, Susan E.; Haytowitz, David B.; Holden, Joanne M. Tufts University Friedman School of Nutrition Science & Policy, Boston, MA, USA. Journal of Food Composition and Analysis (2006), 19(Suppl.), S66-S73. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575. Journal; General Review written in English. CAN 145:417209 AN 2006:488077 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. In order to develop a database for flavanones, the dominant flavonoid class in the genus citrus, the relevant scientific literature on flavonoids in grapefruit, lemons, and limes was searched, abstracted, documented, standardized by taxons and units (mg/100 g) and examd. for quality. Values for eight flavanones (didymin, eriocitrin, hesperidin, naringin, narirutin, neoeriocitrin, neohesperidin, poncirin) are presented. Grapefruit had a total flavanone content (summed means) of 27 mg/100 g as aglycons and a distinct flavanone profile, dominated by naringin. White grapefruit varieties tended to be slightly but not significantly higher in total flavanones than pink and red varieties. For lemons, total flavanones (summed means) were 26 mg/100 g and for limes 17 mg/100 g. The flavanone profiles of both lemons and limes were dominated by hesperidin and eriocitrin.

Abstract CAN 145:417210 AN 2006:488078 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

11β-Hydroxysteroid dehydrogenase (11β-HSD) enzymes catalyze the conversion of biol. inactive 11-ketosteroids into their active 11β-hydroxy derivs. and vice versa. Inhibition of 11β-HSD1 has considerable therapeutic potential for glucocorticoid-assocd. diseases including obesity, diabetes, wound healing, and muscle atrophy. Because inhibition of related enzymes such as 11β-HSD2 and 17β-HSDs causes sodium retention and hypertension or interferes with sex steroid hormone metab., resp., highly selective 11β-HSD1 inhibitors are required for successful therapy. Here, the authors employed the software package Catalyst to develop ligand-based multifeature pharmacophore models for 11β-HSD1 inhibitors. Virtual screening expts. and subsequent in vitro evaluation of promising hits revealed several selective inhibitors. Efficient inhibition of recombinant human 11β-HSD1 in intact transfected cells as well as endogenous enzyme in mouse 3T3-L1 adipocytes and C2C12 myotubes was demonstrated for compd. (I), which was able to block subsequent cortisol-dependent activation of glucocorticoid receptors with only minor direct effects on the receptor itself. Our results suggest that inhibitor-based pharmacophore models for 11β-HSD1 in combination with suitable cell-based activity assays, including

Abstract

The Discovery of New 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitors by Common Feature Pharmacophore Modeling and Virtual Screening. Schuster, Daniela; Maurer, Evelyne M.; Laggner, Christian; Nashev, Lyubomir G.; Wilckens, Thomas; Langer, Thierry; Odermatt, Alex. Institute of Pharmacy, Department of Pharmaceutical Chemistry, University of Innsbruck, Innsbruck, Austria. Journal of Medicinal Chemistry (2006), 49(12), 3454-3466. Publisher: American Chemical Society, CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 145:137256 AN 2006:476237 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The bioassay-guided fractionation of the MeOH ext. of the root barks of Cudrania tricuspidata furnished three hepatoprotective compds., gerontoxanthone A (2), cudraflavone B (4), gericudranin E (5), together with four prenylated xanthones, cudraxanthone B (3), isocudraxanthone K (6), cudraxanthone C (7), cudraxanthone H (8), and a prenylated flavanone, euchrestaflavanone C (1). Compds. 4 and 5 showed significant hepatoprotective effects with the EC50 values of 37.39±0.4 and 39.87±0.7 μM, resp., and compd. 2 showed moderate hepatoprotective effect with an EC50 value of 125.9±1.5 μM, against tacrine-induced cytotoxicity in Hep G2 cells. Silybin as pos. control showed an EC50 value of 84.76±0.5 μM. Isocudraxanthone K is a new compd.

Abstract

Hepatoprotective compounds of the roots of Cudrania tricuspidata on tacrine-induced cytotoxicity in Hep G2 cells. An, Ren-Bo; Sohn, Dong-Hwan; Kim, Youn-Chul. College of Pharmacy, Wonkwang University, Iksan, S. Korea. Biological & Pharmaceutical Bulletin (2006), 29(4), 838-840. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 145:202798 AN 2006:477188 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(2S)-5,7,2',5'-tetrahydroxyflavanone, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-β-D-glucopyranoside, (2S)-5,7,2',5'-tetrahydroxyflavanone 7-O-β-D-glucuronopyranoside, (2S)-7,2'-dihydroxy-5-methoxyflavanone 7-O-β-D-glucuronopyranoside, (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',II-5'-heptahydroxy-[I-6,II-6']-flavanonylflavone and (I-2S)-I-5,II-5,I-7,II-7,I-2',II-2',I-5',II-5'-octahydroxy-[I-6,II-6']-flavanonylflavone, were isolated, together with ten known flavonoids, wogonin (5,7-dihydroxy-8-methoxyflavone), 5,7-dihydroxy-8,2'-dimethoxyflavone, (2S)-5,7,2'-trihydroxyflavanone, scutevulin (5,7,2'-trihydroxy-8-methoxyflavone), 5,7,4'-trihydroxy-8-methoxyflavone, alpinetin ((2S)-7-hydroxy-5-methoxyflavanone), 5,7,2'-trihydroxyflavone, 5,7,2',5'-tetrahydroxyflavone, (2S)-7,2'-dihydroxy-5-methoxyflavanone and 5,7-dihydroxy-8,2'-dimethoxyflavone 7-O-β-D-glucuronopyranoside. The structures were detd. on the basis of chem. and spectral data.


flavanone

In an earlier study, we reported that nitric oxide is involved in lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate-induced Abstract

Lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate induction of migration and invasion of glioma cells in vitro and in vivo: Differential inhibitory effects of flavonoids. Shen, S. C.; Lin, C. W.; Lee, H. M.; Chien, L. L.; Chen, Y. C. Department of Dermatology, School of Medicine, Taipei Medical University, Taipei, Taiwan. Neuroscience (San Diego, CA, United States) (2006), 140(2), 477-489. Publisher: Elsevier, CODEN: NRSCDN ISSN: 0306-4522. Journal written in English. CAN 145:116894 AN 2006:461813 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Naringenin is a flavanone compd. that alters crit. cellular processes such as cell multiplication, glucose uptake, and mitochondrial activity. The social amoeba Dictyostelium discoideum was used as a model system for examg. the cellular processes and signaling pathways affected by naringenin. Naringenin inhibited Dictyostelium cell division in a dose-dependent manner (IC50 .apprx. 20 μM). Assays of Dictyostelium chemotaxis and multicellular development revealed that naringenin possesses a previously unrecognized ability to suppress amoeboid cell motility. Naringenin, which is known to inhibit phosphatidylinositol 3-kinase activity, had no apparent effect on phosphatidylinositol 3,4,5-trisphosphate synthesis in live Dictyostelium cells; suggesting that this compd. suppresses cell growth and migration via alternative signaling pathways. In another context, the discoveries described here highlight the value of using the Dictyostelium model system for identifying and characterizing the mechanisms by which naringenin, and related compds., exert their effects on eukaryotic cells.

Abstract

Naringenin is a novel inhibitor of Dictyostelium cell proliferation and cell migration. Misty, Russ; Martinez, Raquel; Ali, Hind; Steimle, Paul A. Department of Biology, University of North Carolina, Greensboro, NC, USA. Biochemical and Biophysical Research Communications (2006), 345(1), 516-522. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 145:244739 AN 2006:470536 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Me

Me

H

Me

CH

Me CH 2 CH 2 CO 2H

MeMe

AcO

O

O

I

such for related enzymes, can be used for the identification of selective and potent inhibitors.


flavanone

Three naturally occurring di-C-glycosylflavonoids, phloretin (dihydrochalcone) I, naringenin (flavanone) II, and apigenin (flavone) III bis-6,8-C-β-D-glucopyranosides, were synthesized in total yields of 52.3%, 53.5%, and 36.4%, resp., starting from the key compd., di-C-β-D-glucopyranosylphloroacetophenone (IV). Benzyl protection of the phenolic hydroxyls in IV and a subsequent aldol condensation with benzyloxybenzaldehyde led to the prodn. of chalcone, which, after hydrogenolysis or acid hydrolysis and deprotection, gave I and II, resp. The acetylation of II, followed by DDQ oxidn. and deprotection, gave III.

Abstract

Total synthesis of three naturally occurring 6,8-di-C-glycosylflavonoids: phloretin, naringenin, and apigenin bis-C-β-D-glucosides. Sato, Shingo; Akiya, Toshiki; Nishizawa, Hiroaki; Suzuki, Toshiyuki. Department of Chemistry and Chemical Engineering, Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata, Japan. Carbohydrate Research (2006), 341(8), 964-970. Publisher: Elsevier B.V., CODEN: CRBRAT ISSN: 0008-6215. Journal written in English. CAN 145:145935 AN 2006:453947 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


transformation and colony formation, and attenuation of inducible nitric oxide synthase, phosphorylated extracellular regulated protein kinases protein expression, and metalloproteinase 9 enzyme activity was obsd. 2'-OH flavone at a dose of 100 μM inhibition of lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced events via apoptosis induction is identified. Furthermore, lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate, but not lipopolysaccharide or 12-o-tetradecanoylphorbol 13-acetate, induces tumoral invasion and migration in vitro and in vivo, and those are blocked by kaempferol and wogonin addn. These data suggest that combination of lipopolysaccharide and 12-o-tetradecanoylphorbol 13-acetate promotes tumoral progression via activating metalloproteinase 9 enzyme activity and inducible nitric oxide synthase gene expression, which is located downstream of mitogen-activated protein kinases activation, in rat glioma cells C6. Kaempferol and wogonin exhibit effective inhibitory effects on lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced events, and thus possess the potential for further development.

malignant transformation via increases in metalloproteinase 9 enzyme activity and inducible nitric oxide synthase gene expression in rat glioma C6 cells, however the mechanism has remained undefined. Lipopolysaccharide plus 12-o-tetradecanoylphorbol 13-acetate, but not lipopolysaccharide or 12-o-tetradecanoylphorbol 13-acetate alone, induced transformation in glioma C6 cells (but not in human glioblastoma cells GBM-8401 cells) without affecting their viability. An increase in inducible nitric oxide synthase protein expression, nitric oxide prodn., and metalloproteinase 9 enzyme activity is identified lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-treated C6 cells, however lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate and 12-o-tetradecanoylphorbol 13-acetate (but not lipopolysaccharide) addn. shows the similar inductive pattern on metalloproteinase 9 enzyme activity without affecting inducible nitric oxide synthase protein expression and nitric oxide prodn. in GBM-8401 cells. Treatment of C6 cells with lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate increases the expression of phosphorylated extracellular regulated protein kinases and Jun N-terminal kinases, but not p38, proteins, and an addn. of the extracellular regulated protein kinases inhibitor PD98059 or Jun N-terminal kinases inhibitors SP600125, but not the p38 inhibitor SB203580, significantly blocked lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced inducible nitric oxide synthase protein expression and metalloproteinase 9 enzyme activity accompanied by blocking morphol. transformation in C6 cells. Among 19 structurally related flavonoids, kaempferol and wogonin exhibit significant inhibitory effects on lipopolysaccharide/12-o-tetradecanoylphorbol 13-acetate-induced morphol.


flavanone

Answer 436:

O

OHOH OH

HO

O

HO HO

HO

OHO

OH

OH

HO OH

O

OHOH OH

HO

O

HO HO

HO

OHO

O

OH

HO

OH

O

OHOH OH

HO

O

HO HO

HO

OHO

O

OH

HO

OH

I

III

II


flavanone

Abstract

Inhibition of CYP6B1-Mediated Detoxification of Xanthotoxin by Plant Allelochemicals in the Black Swallowtail (Papilio polyxenes). Wen, Zhimou; Berenbaum, May R.; Schuler, Mary A. Department of Cell and Developmental Biology, University of Illinois, Urbana, IL, USA. Journal of Chemical Ecology (2006), 32(3), 507-522. Publisher: Springer, CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 145:120776 AN 2006:438270 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Traditional Chinese medicinal plants assocd. with anticancer contain a wide variety of natural phenolic compds. with various structural features and possessing widely differing antioxidant activity. The structure-radical scavenging activity relationships of a large no. of representative phenolic compds. (e.g., flavanols, flavonols, chalcones, flavones, flavanones, isoflavones, tannins, stilbenes, curcuminoids, phenolic acids, coumarins, lignans, and quinones) identified in the traditional Chinese medicinal plants were evaluated using the improved ABTS⋅+ and DPPH methods. Different categories of tested phenolics showed significant mean differences in radical scavenging activity. Tannins demonstrated the strongest activity, while most quinones, isoflavones, and lignans tested showed the weakest activity. This study confirmed that the no. and position of hydroxyl groups and the related glycosylation and other substitutions largely detd. radical scavenging activity of the tested phenolic compds. The differences in radical scavenging activity were attributed to structural differences in hydroxylation, glycosylation and methoxylation. The ortho-dihydroxy groups were the most important structural feature of high activity for all tested phenolic compds. Other structural features played a modified role in enhancing or reducing the activity. Within each class of phenolic compds., the structure-activity relation was elucidated and discussed. This study reveals the structure-activity relationships of a large series of representative natural phenolic compds. more systematically and fully than previous work. Structure-radical scavenging activity relationships of some natural phenolics identified in the medicinal plants were evaluated for the first time.

Abstract

Structure-radical scavenging activity relationships of phenolic compounds from traditional Chinese medicinal plants. Cai, Yi-Zhong; Sun, Mei; Jie Xing; Luo, Qiong; Corke, Harold. Department of Botany, The University of Hong Kong, Hong Kong, Peop. Rep. China. Life Sciences (2006), 78(25), 2872-2888. Publisher: Elsevier B.V., CODEN: LIFSAK ISSN: 0024-3205. Journal written in English. CAN 145:327633 AN 2006:442308 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Because of health benefits of phenolic compds. in wine, it is important to investigate their structure-property relationship. We have investigated linear and nonlinear (polynomial) relationships between given topol. indexes and lipophilicity of polyphenols, main pharmacol. active components of wine.

Abstract

Molecular modeling of polyphenols from Croatian wines. Medic-Saric, M.; Mornar, A.; Rastija, V.; Jasprica, I.; Nikolic, S. Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia. Lecture Series on Computer and Computational Sciences (2005), 4 B(Advances in Computational Methods in Sciences and Engineering), 1566-1569. Publisher: Brill Academic Publishers, CODEN: LSCCAR ISSN: 1573-4196. Journal written in English. CAN 145:375961 AN 2006:451563 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The synthesis of (±)-diinsininone (I), the racemic aglycon of diinsinin, was reported. This was the first construction of a proanthocyanidin (PA) type-A compd. incorporating a [3.3.1]-bicyclic ketal as its characteristic core. The strategy utilized a coupling between a benzopyrilium salt and a flavanone that proved applicable to other PA type-A compds. During this undertaking, treatment of (±)-naringenin with 2-iodoxybenzoic acid (IBX) followed by reductive work-up afforded (±)-eriodictyol. This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations included the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddn.-oxidn. sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of diinsinin from the aglycon I.

Abstract

(±)-Diinsininone: made nature's way. Selenski, Carolyn; Pettus, Thomas R. R. University of California, Santa Barbara, Department of Chemistry & Biochemistry, Santa Barbara, CA, USA. Tetrahedron (2006), 62(22), 5298-5307. Publisher: Elsevier B.V., CODEN: TETRAB ISSN: 0040-4020. Journal written in English. CAN 145:103457 AN 2006:428115 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new dihydroflavonoids named villosin A and villosin B were obtained from the traditional Chinese medicinal herb Patrinia villosa Juss. Their structures were elucidated as (2S)-5,2',6'-trihydroxy-2'',2''-dimethylpyrano [5'',6'':6,7]flavanone and (2S,3''S)-5,2',6'-trihydroxy-3''-γ,γ-dimethylallyl-2'',2''-dimethyl-3'',4''-dihydropyrano [5'',6'':6, 7]flavanone by spectroscopic methods including UV, IR, HR-TOF-MS, 1D NMR and 2D NMR techniques.

Abstract

Two new dihydroflavanoids from Patrinia villosa Juss (II). Peng, Jin Yong; Fan, Guo Rong; Wu, Yu Tian. Shanghai Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep. China. Chinese Chemical Letters (2006), 17(4), 485-488. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 145:310521 AN 2006:434483 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The structural and biosynthetic diversity of allelochems. in plants is thought to arise from selection for additive toxicity as a consequence of toxin mixt. or for enhanced toxicity as a result of synergism. In order to understand how insects cope with this type of plant defense, we tested the effects of some allelochems. in host plants of the black swallowtail Papilio polyxenes on the xanthotoxin-metabolic activity of CYP6B1, the principal enzyme responsible for the detoxification of furanocoumarins in this caterpillar. Addnl., the effects of some synthetic compds. not normally encountered by P. polyxenes on CYP6B1 were tested. These studies demonstrate that the integrity of furanocoumarin structure is important for competitive binding to the active site of CYP6B1, even though the carbonyl group on the pyranone ring apparently does not affect its inhibitory capacity, as in the case of furanochromones. Angular furanocoumarins are generally less phototoxic to many organisms than linear furanocoumarins due to their reduced capacity for crosslinking DNA strands, yet they are more toxic than linear furanocoumarins to black swallowtail larvae. This enhanced toxicity in vivo may be due to the ability of angular furanocoumarins to bind to the active site of CYP6B1 without being rapidly metabolized. This binding reduces the availability of CYP6B1 to metabolize other linear furanocoumarins. The structure-activity relationships for methylenedioxyphenyl compds., flavonoids, imidazole, and imidazole derivs. are also discussed in light of their capacity to inhibit the xanthotoxin-metabolic activity of CYP6B1.


flavanone

Abstract

Roles of HMGB-1 and soluble RAGE in endotoxic shock. Hasunuma, Ryoichi; Kawaguchi, Kiichiro; Maruyama, Hiroko; Takimoto, Hiroaki; Kumazawa, Yoshio. Dep. of Science, Kitasato University, Japan. Endotokishin Kenkyu (2005), 8 4-11. Publisher: Igaku Tosho Shuppan K.K., CODEN: EKNEBO Journal; General Review written in Japanese. CAN 145:373465 AN 2006:425934 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Cellulose and amylose phenylcarbamates having one or two alkoxy groups on a Ph ring were synthesized, and their chiral recognition abilities as chiral stationary phases for HPLC were evaluated. Compared to the 4-methoxyphenylcarbamates of cellulose and amylose, which are known to show a poor chiral recognition, the 3-methoxyphenylcarbamates exhibited much higher chiral recognitions. For cellulose derivs., as the bulkiness of the 3-alkoxy group increased, the chiral recognition ability increased. However, for the amylose derivs., a clear relation between the chiral recognition and the bulkiness of the alkoxy group was not obsd., and the 3-methoxy, ethoxy, and isopropoxyphenylcarbamates showed relatively high chiral recognitions. The introduction of two methoxy groups to the meta-positions decreased the chiral recognition ability. To discuss the relation between the structure and chiral recognition ability of the alkoxyphenylcarbamates, their mol. models were constructed.

Abstract

Enantioseparation using alkoxyphenylcarbamates of cellulose and amylose as chiral stationary phase for high-performance liquid chromatography. Yamamoto, Chiyo; Inagaki, Shinji; Okamoto, Yoshio. Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, Japan. Journal of Separation Science (2006), 29(6), 915-923. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 146:74176 AN 2006:427882 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OO

OH

OH

O OH

HO

OH

O

HO I


flavanone

Chem. investigation of S. chrysocaulos from Northeast India yielded 3 new (i.e., 1-3) and 2 known biflavonoids. From S. bryopteris, collected in the southern part of India, 1 new and 11 known biflavonoids of the amentoflavone- and hinokiflavone-type were isolated and identified. The structures of the compds. were elucidated by 1D- and 2D-NMR spectroscopy, and by mass spectrometry. The abs. configurations of chiral biflavonoids with flavanone subunits (from S. bryopteris) were detd. with the aid of circular-dichroism (CD) spectroscopy. Several very rare or even unprecedented substructures in biflavonoids were found.

Abstract

Structurally unique biflavonoids from Selaginella chrysocaulos and Selaginella bryopteris. Swamy, Ramalla Chidananda; Kunert, Olaf; Schuhly, Wolfgang; Bucar, Franz; Ferreira, Daneel; Rani, Vanapatla Swarupa; Kumar, Bobbala Ravi; Rao, Achanta Venkata Narasimha Appa. University College of Pharmaceutical Sciences, Kakatiya University, Warangal, India. Chemistry & Biodiversity (2006), 3(4), 405-413. Publisher: Verlag Helvetica Chimica Acta AG, CODEN: CBHIAM ISSN: 1612-1872. Journal written in English. CAN 145:141184 AN 2006:425705 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The transcriptional regulators for anthocyanin biosynthesis include members of proteins contg. an R2R3-MYB domain, a bHLH (basic helix-loop-helix) domain and conserved WD40 repeats (WDRs). Spacial and temporal expression of the structural genes encoding the enzymes for anthocyanin biosynthesis is thought to be detd. by combinations of the R2R3-MYB, bHLH and WDR factors and their interactions. While the wild-type Japanese morning glory (Ipomoea nil) exhibits blue flowers with colored stems and dark-brown seeds, the c mutants display white flowers with red stems and colored seeds, and the ca mutants exhibit white flowers with green stems and ivory seeds. Here, the authors characterize the tissue-specific expression of three MYB genes, three bHLH genes and two WDR genes in I. nil. The authors also show that the recessive c-1 and ca alleles are frameshift mutations caused by a 2 bp deletion and 7 bp insertions in the genes for the R2R3-MYB and WDR transcriptional regulators designated as InMYB1 and InWDR1, resp. In addn. to defects in flower, stem and seed pigmentations, the ca mutants were found to show reduced trichome formation in seeds but to produce leaf and stem trichomes and root hairs normally. Except for the gene for chalcone synthase E in the ca mutant, all structural genes tested were coordinately reduced in both c-1 and ca mutant flower limbs. However, slight but significant expression of the genes for chalcone synthase D, chalcone isomerase and flavanone 3-hydroxylase in the pathway for flavonol biosynthesis was detectable in c-1 and ca mutants, whereas no such residual expression could be obsd. in other genes involved in the later anthocyanin biosynthesis pathway. The biol. roles of the C-1 and Ca genes in I. nil epidermal traits and their evolutionary implications are also discussed.

Abstract

Isolation of cDNAs for R2R3-MYB, bHLH and WDR transcriptional regulators and identification of c and ca mutations conferring white flowers in the Japanese morning glory. Morita, Yasumasa; Saitoh, Miho; Hoshino, Atsushi; Nitasaka, Eiji; Iida, Shigeru. National Institute for Basic Biology, Okazaki, Japan. Plant and Cell Physiology (2006), 47(4), 457-470. Publisher: Japanese Society of Plant Physiologists, CODEN: PCPHA5 ISSN: 0032-0781. Journal written in English. CAN 145:227471 AN 2006:425798 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review discussing (1) endotoxin shock induced by Salmonella infection in mice, (2) pathol. opinion of the mouse liver with infection-induced endotoxic shock, (3) expression of HMGB-1 in mice with infection-induced endotoxic shock, (4) expression of sol. RAGE in mice with infection-induced endotoxic shock, (5) expression of HMGB-1 in galactosamine-sensitized mice, (6) sol. RAGE expression in galactosamine-sensitized mice and (7) suppression of endotoxic shock in mice by a citrus flavanone naringin and hesperidin.


flavanone

Molecular characterization of the flavonoid biosynthesis of Verbena hybrida and the functional analysis of verbena and Clitoria ternatea F3'5'H genes in transgenic verbena. Togami, Junichi; Tamura, Mihoko; Ishiguro, Kanako; Hirose, Chika;


Nierembergia sp., a popular floricultural species, only has violet and white flower color and lacks pink to red. To elucidate the reason, we analyzed its flavonoids. Its major anthocyanin was detd. to be delphinidin 3-O-(6-O-(4-O-(4-O-(6-O-caffeoyl-β-D-glucopyranosyl)-p-coumaroyl)-α-L-rhamnosyl)-β-D-glucopyranosyl)-5-O-β-D-glucopyranoside. The petals rarely contained cyanidin and pelargonidin, and they contained more flavonols than anthocyanins. We also characterized the biosynthetic pathway by cloning the cDNAs encoding enzymes involved in the flavonoid biosynthesis pathway: chalcone synthase (CHS), flavanone 3-hydrozylase (F3H), flavonoid 3'-hydroxylase (F3'H), flavonoid 3',5'-hydroxylase (F3'5'H), dihydroflavonol 4-reductase (DFR), flavonol synthase (FLS), and UDP-rhamnose: anthocyanidin 3-glucoside rhamnosyltransferase (3RT). Northern blot anal. revealed that the expressions of CHS, F3'5'H, DFR, and 3RT genes were coordinately regulated in parallel with anthocyanin accumulation in the petals, indicating that anthocyanin biosynthesis is transcriptionally regulated; on the other hand, the transcripts of the F3'H gene were rarely detected. Antisense suppression of the F3'5'H gene decreased the amt. of F3'5'H transcripts and that of delphinidin. It was noteworthy that the color of the transgenic flower changed from violet to white rather than to reddish, which was the expectation.

Abstract

Molecular characterization of the flavonoid biosynthetic pathway and flower color modification of Nierembergia sp. Ueyama, Yukiko; Katsumoto, Yukihisa; Fukui, Yuko; Fukuchi-Mizutani, Masako; Ohkawa, Hideo; Kusumi, Takaaki; Iwashita, Takashi; Tanaka, Yoshikazu. Division of Molecular Science, Graduate School of Science and Technology, Kobe University, 1-1 Rokkodai, Nada, Kobe, Japan. Plant Biotechnology (Tokyo, Japan) (2006), 23(1), 19-24. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 145:468033 AN 2006:412907 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new flavanone, 7-hydroxy-5,6-dimethoxyflavanone (1), together with three other flavonoids, didymocarpin (2), 2',4'-dihydroxy-5',6'-dimethoxychalcone (3), and isodidymocarpin (4), had been isolated from the methanol ext. of the tree bark of Cryptocarya costata. The structures of these compds. were detd. based on spectral evidence, including UV, IR, 1-D and 2-D NMR, and mass spectra. Cytotoxic properties of compds. 1-4 were evaluated against murine leukemia P-388 cells. The chalcones 3 and 4 were found to have substantial cytotoxicity with IC50 of 5.7 and 11.1 μM, resp.

Abstract

Cytotoxic chalcones and flavanones from the tree bark of Cryptocarya costata. Usman, Hanapi; Hakim, Euis H.; Harlim, Tjodi; Jalaluddin, Muhammad N.; Syah, Yana M.; Achmad, Sjamsul A.; Takayama, Hiromitsu. Chemistry Department, Hasanuddin University, Makassar, Indonesia. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2006), 61(3/4), 184-188. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 146:32542 AN 2006:425063 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone




W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Use of glycosylated flavanones for the browning of skin or hair. Vielhaber, Gabriele; Jacobs, Karin; Herrmann, Martina. (Symrise Gmbh & Co. KG, Germany). PCT Int. Appl. (2006), 69 pp. CODEN: PIXXD2 WO 2006045760 A1 20060504 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, LY, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2005-EP55464 20051021. Priority: US 2004-621855 20041025. CAN 144:439568 AN 2006:411812 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Homologues of the flavonoid 3',5'-hydroxylase (F3'5'H) gene, a key gene detg. flower color, were obtained from a Verbena hybrida (verbena) cultivar Temari Violet, verbena cultivar Tapien Pink, and Clitoria ternatea (butterfly pea). The expression of the Temari and butterfly pea homologues in yeast confirmed that they encoded F3'5'H. The two genes under the control of an enhanced cauliflower mosaic virus 35S promoter were introduced into verbena Temari Sakura. Some of the transgenic verbena plants had elevated delphinidin contents and flower color altered toward violet. Interestingly, the butterfly pea F3'5'H gene yielded more delphinidin and gave clearer flower color change than the verbena Temari gene in the transgenic verbena plants. The results indicate that the choice of the gene source should be considered to obtain strong phenotypic changes, even if the genes encode the same enzymic activity. We also cloned some flavonoid biosynthetic genes from verbenas. The potential usefulness of verbena in the phytomonitoring of environmental pollutants is also discussed.

Abstract

Okuhara, Hiroaki; Ueyama, Yukiko; Nakamura, Noriko; Yonekura-Sakakibara, Keiko; Fukuchi-Mizutani, Masako; Suzuki, Ken-ichi; Fukui, Yuko; Kusumi, Takaaki; Tanaka, Yoshikazu. Institute for Advanced Technology, Suntory, Ltd., 1-1-1 Wakayamadai, Shimamoto, Osaka, Japan. Plant Biotechnology (Tokyo, Japan) (2006), 23(1), 5-11. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 145:468083 AN 2006:412905 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


The synthesis and evaluation of new dinitrophenyl (DNP) substituted β-cyclodextrin (β-CD) chiral stationary phases (CSPs) for the enantiosepn. of various classes of chiral analytes by HPLC are presented. The dinitrophenyl substituted β-CD derivs. were synthesized and covalently bonded to functionalized 5 μm spherical porous silica gel. These are the 1st reported derivatized cyclodextrin which contains π-electron deficient substituents (i.e., π-acidic moieties). The column performance in terms of their ability to sep. enantiomers is evaluated. A variety of different dinitro-substituted aryl groups were studied and compared. The pH of the mobile phase buffers, the buffer compn., the no. and position of the dinitro groups on the Ph ring substituent, the degree of substitution, and the bonding strategy all greatly affect the performance of the CSPs. A large variety of racemic compds. were sepd. successfully on these CSPs. The bonded dinitrophenyl-derivatized cyclodextrins are stable in all three mobile phase modes, namely, the reversed-phase, polar org., and normal phase modes. No degrdn. in column performance was obsd. in any mode of operation even after >1000 injections. The anal. applicability of these types of CSPs for enantiomeric sepns. is discussed.

Abstract

Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography. Zhong, Qiqing; He, Lingfeng; Beesley, Thomas E.; Trahanovsky, Walter S.; Sun, Ping; Wang, Chunlei; Armstrong, Daniel W. Department of Chemistry, Iowa State University, Ames, IA, USA. Journal of Chromatography, A (2006), 1115(1-2), 19-45. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 145:136942 AN 2006:410818 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OO

OOH

R3

R1

R2R4

I

The use of a compd. having formula (I) is described as an agent for the browning of skin or hair wherein: R1 and R2 are mutually independently H, OH, C1-C10-alkyl, C1 -C10-O-alkyl or O-prenyl, R3 is H, OH, O-glucose or O-rhamnose and R4 is a monosaccharide radical or an oligosaccharide radical having 2, 3, 4 or 5 carbohydrate units, with the proviso that the compd. having formula I is not used in the form of a prepn. based on Citrus aurantium dulcis.

Abstract WO 2005-EP55464 W 20051021US 2004-621855P P 20041025Priority Application


flavanone

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, LV, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH,


WO 2006048339 A3 20060727WO 2006048339 A2 20060511 WO 2005-EP13527 20051104FR 2877223 A1 20060505 FR 2004-52518 20041104FR 2877221 A1 20060505 FR 2004-12368 20041122Patent No. Kind Date Application No. Date Patent Family Information

Cosmetic composition containing an active agent and a urea compound. Burnier, Veronique; Lorant, Raluca. (L'Oreal, Fr.). Fr. Demande (2006), 36 pp. CODEN: FRXXBL FR 2877221 A1 20060505 Patent written in French. Application: FR 2004-12368 20041122. Priority: FR 2004-52518 20041104. CAN 144:439565 AN 2006:409419 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


1, 2 and 3 exhibited high anticancer activities (IC50 < 7 μg/mL), esp. to K562 cancer cell (IC50 < 3.1 μg/mL), and the compds. 4, 5 and 6 exhibited weaker inhibition effect (IC50 < 30 μg/mL).

A preparative counter-current chromatog. (CCC) was used to isolate and sep. chem. constituents from the leaf of Patrinia villosa, a famous traditional Chinese medicinal herb. Six flavonoids including two known and four novel compds. were successfully simultaneous purified by CCC with a two-phase solvent system composed of n-hexane-Et acetate-methanol-water (10: 13: 13: 10, vol./vol.) by increasing the flow rate of the mobile phase from 1.0 mL/min to 2.0 mL/min after 110 min to bring out the late eluters. The sepn. produced total of 44.9 mg fraction I with 99.1% purity, 35.5 mg fraction II with 98.8% purity, 79.8 mg fraction III with 99.3% purity, 45.8 mg fraction IV with 98.8% purity, 39.8 mg fraction V with 98.6% purity and 9.6 mg fraction VI with 97.5% purity from 400 mg crude ext. in one single isolation procedure and less than 10 h, and the obtained fractions were all analyzed by high performance liq. chromatog. (HPLC). Their chem. structures were elucidated as (2S)-5,7,2',6'-tetrahydroxy-6,8-di (γ,γ-dimethylallyl) flavanone (1), (2S)-5,7,2',6'-tetrahydroxy-6-lavandulylated flavanone (2), (2S)-5,7,2',6'-tetrahydroxy-4'-lavandulylated flavanone (3), (2S)-5,2',6'-trihydroxy-2'',2''-dimethylpyrano [5'', 6'': 6, 7] flavanone (4), (2S, 3''S)-5,2',6'-trihydroxy-3''-γ,γ-dimethylallyl-2'',2''-dimethyl-3'',4''-dihydropyrano [5'', 6'': 6, 7] flavanone (5) and licoagrochalcone B (6), resp., by spectrum methods including UV, IR, high resoln. (HR)-electrospray ionization (ESI)-MS, 1-dimension (1D) and 2-dimension (2D) NMR techniques. Among them, compds. 2, 3, 4, and 5 were new compds. and discovered from nature for the first time. The recoveries of the six compds. were 91.2%, 91.4%, 92.1%, 90.5%, 90.3% and 89.7%, resp., in CCC step. Subsequently, their anticancer activities were also examd. to inhibit human cancer cells' growth including A549, BEL-7402, SGC-7901, MCF-7, HT-29, K562 and A498 cell lines by MTT method in vitro. The results indicated that the compds.

Abstract

Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro. Peng, Jinyong; Fan, Guorong; Wu, Yutian. Shanghai Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep. China. Journal of Chromatography, A (2006), 1115(1-2), 103-111. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 145:20665 AN 2006:410810 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

New anti-inflammatory active flavanone glycoside from the Echinops echinatus Roxb. Yadava, R. N.; Singh, S. K. Natural Products Laboratory, Department of Chemistry, Dr. H. S. Gour University, Sagar, India. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2006), 45B(4), 1004-1008. Publisher: National Institute of Science Communication and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 145:351890 AN 2006:391088 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoid and limonoid compds. were detd. by HPLC on the methanol and ethanol exts. from citron seeds. The quantities of the compds. in these categories were higher in the ethanol ext. than methanol ext. The types of these compds. were detected in larger nos. in the ethanol ext. The content of limonin was the largest in both methanol and ethanol ext. among the detectable compds.; 140.34 mg/100 g and 170.98 mg/100 g, resp., and the contents of other compds., caffeic acid, naringin, lutin, nomilin, were found in large amt. in this order. The mol. wts. of forty two compds. in ethanol ext. were detd. with mass spectra and extd. ion current chromatograms by HPLC/MS.

Abstract

Determination of flavonoid and limonoid compounds in citron (Citrus junos Sieb. et Tanaka) seeds by HPLC and HPLC/MS. Woo, Kang-Lyung; Kim, Je-I.; Kim, Min-Chul; Chang, Duck-Kyu. Division of Food Science and Biotechnology, Kyungnam University, Masan, S. Korea. Han'guk Sikp'um Yongyang Kwahak Hoechi (2006), 35(3), 353-358. Publisher: Korean Society of Food Science and Nutrition, CODEN: HSYHFB ISSN: 1226-3311. Journal written in Korean. CAN 145:487881 AN 2006:407514 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A cosmetic compn. comprises a hydroxylated urea compd. and an active agent chosen from dermorelaxants, agents stimulating the synthesis of dermal or epidermal extracellular matrix fibers located on the dermo-epidermal junction and/or preventing their degrdn., anti-glycation agents, lipolytic agents or lipogenesis inhibitors, anti-irritants agents and their mixts. The invention also discloses a compn. contg. a hydroxylated urea compd. and an agent chosen from carotenoids, retinoids, flavanones, flavonols, isoflavones, coumarins, lignans, stilbenoids, sapogenins, triterpene pentacyclic acids, β-hydroxy acids, their derives., ethers, or heterosides, phenolic acids, precursor monomers of tannins, aminosugars, peptides, and their mixts. for the care and make-up of the skin. A lotion contained carbomer 0.20, Me paraben 0.2, 2-hydroxyethyl urea 5, caffeine 0.5, oils 5, stearic acid 3, glyceryl stearate 0.50,, cetyl alc. 0.20, triethanolamine 0.5, diazolidinyl urea 0.3, and water q.s. 100%.

Abstract FR 2004-12368 A 20041122US 2004-627284P P 20041115FR 2004-52518 A 20041104Priority Application

GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM


flavanone

Antioxidative flavanone glycosides from the branches and leaves of Viscum coloratum. Yao, Hui; Liao, Zhi-Xin; Wu, Qiong; Lei, Guang-Qing; Liu, Zhi-Jun; Chen, Dao-Feng; Chen, Jia-Kuan; Zhou, Tong-Shui. Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, Peop. Rep. China. Chemical & Pharmaceutical Bulletin (2006), 54(1), 133-135. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 144:447888 AN 2006:373247 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The MeOH ext. of Sophora flavescens showed a potent glycosidase inhibitory activity. Active components were identified as well-known flavonoid antioxidants: kushenol A (1), (-)-kurarinone (2), sophoraflavanone G (3), 2'-methoxykurarinone (4), kurarinol (5), 8-prenylkaempferol (6), isoxanthohumol (7), kuraridine (8), and maackiain (9). All flavonoids were effective inhibitors of α-glucosidase and β-amylase. Interestingly, lavandulylated flavanones 1-5 had strong α-glucosidase inhibitory activities, with IC50 values of 45, 68, 37, 155, and 179 μM, resp. Kushenol A (1) which does not bear a 4'-hydroxy group showed selective α-glucosidase inhibitory activity. Lavandulylated chalcone, kuraridine (8), exhibited IC50 value of 57 μM against β-glucosidase, which is the 1st report of a chalcone displaying glycosidase inhibition. Results showed that 8-lavandulyl group in B-ring was a key factor of the glycosidase inhibitory activities. The inhibition pattern was noncompetitive for α-glucosidase, whereas mixed inhibition was obsd. for β-amylase.

Abstract

Glycosidase inhibitory flavonoids from Sophora flavescens. Kim, Jin Hyo; Ryu, Young Bae; Kang, Nam Suk; Lee, Byong Won; Heo, Jong Soo; Jeong, Ill-Yun; Park, Ki Hun. Division of Applied Life Science (BK21 Program), Institute of Agricultural & Life Sciences, Department of Agricultural Chemistry, Gyeongsang National University, Jinju, S. Korea. Biological & Pharmaceutical Bulletin (2006), 29(2), 302-305. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 145:20883 AN 2006:378916 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new flavanone, 3',5',7-trihydroxyflavanone, was isolated from the methanol ext. of the wood of A. fruticosa by column chromatog. Its chem. structure was identified by instrumental anal. using UV, IR, mass, and NMR spectrometer.

Abstract

A new flavanone from the wood of Amorpha fruticosa L. Lee, Hyun-Jung; Lee, Oh-Kyu; Kwon, Yeong-Han; Choi, Don-Ha; Kang, Ha-Young; Lee, Hyeon-Yong; Paik, Ki-Hyon; Lee, Hak-Ju. Div. Wood Chemistry & Microbiology, Korea Forest Research Institute, Seoul, S. Korea. Bulletin of the Korean Chemical Society (2006), 27(3), 426-428. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN: 0253-2964. Journal written in English. CAN 145:99565 AN 2006:384363 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new antiinflammatory active flavanone glycoside 5,7-dihydroxy-8,4'-dimethoxyflavanone-5-O-α-L-rhamnopyranosyl-7-O-β-D-arabinopyranosyl-(1→4)-O-β-D-glucopyranoside A along with a known compd. dihydroquercetin-4'-Me ether B have been isolated from the leaves of Echinops echinatus.


flavanone


Flavanone (1) and 6-hydroxyflavanone (2) were subjected to transformation by means of Aspergillus niger strains (one wild and three UV mutants). For both substrates the biotransformation resulted in redn. of the carbonyl group (products 5 and 7) and dehydrogenation at C-2 and C-3 (3 and 8). Addnl., for flavanone (1) redn. of C-4 together with hydroxylation at C-7 (6) and dehydrogenation at C-2, C-3 along with hydroxylation at C-3 (4) were obsd.

Abstract

Microbial transformations of flavanone and 6-hydroxyflavanone by Aspergillus niger strains. Kostrzewa-Suslow, Edyta; Dmochowska-Gladysz, Jadwiga; Bialonska, Agata; Ciunik, Zbigniew; Rymowicz, Waldemar. Department of Chemistry, Agricultural University, Wroclaw, Pol. Journal of Molecular Catalysis B: Enzymatic (2006), 39(1-4), 18-23. Publisher: Elsevier B.V., CODEN: JMCEF8 ISSN: 1381-1177. Journal written in English. CAN 145:123081 AN 2006:366220 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The reactions of 5-substituted-2-aminobenzenethiols, were carried out with the flavindogenide, 3-(4-ethoxybenzylidene)-flavanone in parallel sets that is in acidic and basic media, to obtain 10-substituted-6a,7-dihydro-6H-7-(4-ethoxyphenyl)-6-Ph[1]benzopyrano[3,4-c][1,5]benzothiazepines. The structural assignments are based on microestimations for the elements and IR, 1H NMR and mass spectral analyses. Antibacterial activity studies against Escherichia coli and GFC, using Bacitracin as ref. compd., and antifungal studies against Aspergillus niger, A. flavus and Curvularia lunata, using Mycostatin as the ref. compd., were carried out. All the compds. showed moderate antibacterial activity but significant antifungal activity.

Abstract

Syntheses of 1,5-benzothiazepines. Part XXIX. Syntheses and antimicrobial studies of 10-substituted-6a,7-dihydro-6H-7-(4-ethoxyphenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines. Pant, Seema; Sharma, Priyanka; Chandra, Hem; Pant, Umesh C. LBS Government P.G. College, Kotputli, India. Indian Journal of Heterocyclic Chemistry (2006), 15(3), 289-290. Publisher: Prof. R. S. Varma, CODEN: IJCHEI ISSN: 0971-1627. Journal written in English. CAN 146:7929 AN 2006:372603 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new flavanone glucosides, (2S)-homoeriodictyol 7,4'-di-O-β-D-glucopyranoside (4) and (2R)-eriodictyol 7,4'-di-O-β-D-glucopyranoside (5) were isolated from the branches and leaves of Viscum coloratum (KOMAR) NAKAI (Loranthaceae), along with three known flavanone glucosides: (2S)-homoeriodictyol 7-O-β-D-glucopyranoside (1), (2S)-eriodictyol 7-O-β-D-glucopyranoside (2), and (2S)-naringenin 7-O-β-D-glucopyranoside (3). The structures of these compds. were elucidated using spectroscopic methods. The antioxidant activities of these isolated compds. were evaluated by colorimetric methods based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, resp. All the compds. showed potent albeit varied degrees of antioxidative activities and the structure-activity relationship is discussed.

Abstract


flavanone

Sugars act as signaling mols., whose signal transduction pathways may lead to the activation or inactivation of gene expression. Whole-genome transcript profiling reveals that the flavonoid and anthocyanin biosynthetic pathways are strongly up-regulated following sucrose (Suc) treatment. Besides mRNA accumulation, Suc affects both flavonoid and anthocyanin contents. We investigated the effects of sugars (Suc, glucose, and fructose) on genes coding for flavonoid and anthocyanin biosynthetic enzymes in Arabidopsis (Arabidopsis thaliana). The results indicate that the sugar-dependent up-regulation of the anthocyanin synthesis pathway is Suc specific. An altered induction of several anthocyanin biosynthetic genes, consistent with in vivo sugar modulation of mRNA accumulation, is obsd. in the phosphoglucomutase Arabidopsis mutant accumulating high levels of sol. sugars.

Abstract

Sucrose-specific induction of the anthocyanin biosynthetic pathway in Arabidopsis. Solfanelli, Cinzia; Poggi, Alessandra; Loreti, Elena; Alpi, Amedeo; Perata, Pierdomenico. Department of Crop Plant Biology, University of Pisa, Pisa, Italy. Plant Physiology (2006), 140(2), 637-646. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 144:447906 AN 2006:349184 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Aim of study: Search for plant compds. possessing anti-leukemic properties. Results: We have shown that 5-hydroxy-7-methoxy flavanone (pinostrobin) isolated from Polygonum lapathifolium ssp. nodosum quickly penetrates through cytoplasm to the cellular nucleus of the cultured cells, and gives intensive apoptotic response in stimulating leukemic cells in vitro. The no. of apoptotic cells increased with the concn. of pinostrobin: 10 nM - 25% and 60%; 100 nM - 45% and 76%; 1 μM - 70% and 88% for Jurkat and HL60 cell lines, resp. Conclusion: Pinostrobin may be considered as a good candidate for a leukemia chemopreventive agent.

Abstract

Pinostrobin - an anti-leukemic flavonoid from Polygonum lapathifolium L. ssp. nodosum (Pers.) Dans. Smolarz, Helena D.; Mendyk, Ewaryst; Bogucka-Kocka, Anna; Kocki, Janusz. Chief and Department of Pharmaceutical Botany, Medical University of Lublin, Lublin, Pol. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2006), 61(1/2), 64-68. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 144:445030 AN 2006:354394 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


From the pods of Millettia erythrocalyx, 2'-hydroxy-3,4-dimethoxy-[2'',3'':4',3']-furanochalcone, 2',3-dihydroxy-4-methoxy-4'-γ,γ-dimethylallyloxychalcone, (-)-(2S)-6,3',4'-trimethoxy-[2'',3'':7,8]-furanoflavanone, 3',4'-methylenedioxy-[2'',3'':7,8]-furanoflavonol and 6,3'-dimethoxy-[2'',3'':7,8]-furanoflavone were isolated, along with six other known flavonoids. Their structures were elucidated through anal. of their spectroscopic data.

Abstract

Flavonoids from the pods of Millettia erythrocalyx. Sritularak, Boonchoo; Likhitwitayawuid, Kittisak. Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand. Phytochemistry (Elsevier) (2006), 67(8), 812-817. Publisher: Elsevier Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 144:464190 AN 2006:357401 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Structure prerequisite for antioxidant activity of silybin in different biochemical systems in vitro. Varga, Zs.; Seres, I.; Bibliographic Information Answer 464:

Agro-industry wastewater was degraded by biodegradability method and the results predict that the wastewater is easily biodegradable. Furthermore, at different substrates concns., the wastewater undergoes two kinetic phases; for example, the oxygen consumption for the oxidn. of carbon source compds. is proportional to first phase degrdn. rate (k1 = 3.9 × 10-3 mg/L⋅h); however, the oxygen consumption and the second phase degrdn. rate (k2 = 0.8 × 10-3 mg/L⋅h) are disagreed; thus, a kinetic model is proposed to explain the biodegrdn. process of the waste and compared with Monod and Alexander-diagrams. Furthermore, the low degrdn. rate of second phase is explained by isolating the non-degradable compds. such as 4'-methoxy-5-hydroxy-7-acetyl flavanone, 2,4-diclorophenol, 4-chlorophenol, and 4-chloroethyl-1,3-benzenedithiol, which were detd. spectroscopically.

Abstract

Kinetic model for wastewater treatment: spectroscopic determination of pollutants. Luna-Pabello, V. M.; Pandiyan, T.; Dominguez, A. E. Facultad de Quimica, Universidad Nacional Autonoma de Mexico, Mexico D.F., Mex. Research Journal of Chemistry and Environment (2006), 10(1), 67-74. Publisher: Research Journal of Chemistry and Environment, CODEN: RJCEF7 ISSN: 0972-0626. Journal written in English. CAN 145:50128 AN 2006:334827 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The ripening of grape (Vitis vinifera) berry is characterized by dramatic changes in gene expression, enzymic activities, and metab. that lead to the prodn. of compds. essential for berry quality. The phenylpropanoid metabolic pathway is one of the components involved in these changes. In this study, the authors describe the cloning and functional characterization of VuMYB5a, a cDNA isolated from a grape L. cv Cabernet Sauvignon berry library. VuMYB5a encodes a protein belonging to a small subfamily of R2R3-MYB transcription factors. Expression studies in grapevine indicate that the VvMYB5a gene is mainly expressed during the early steps of berry development in skin, flesh, and seeds. Overexpression of VvMYB5a in tobacco (Nicotiana tabacum) affects the expression of structural genes controlling the synthesis of phenylpropanoid and impacts on the metab. of anthocyanins, flavonols, tannins, and lignins. Overexpressing VvMYB5a induces a strong accumulation of several phenolic compds., including keracyanin (cyanidin-3-rhamnoglucoside) and quercetin-3-rhamnoglucoside, which are the main anthocyanin and flavonol compds. in tobacco. In addn., VvMYB5a overexpression increases the biosynthesis of condensed tannins and alters lignin metab. These findings suggest that VvMYB5a may be involved in the control of different branches of the phenylpropanoid pathway in grapevine.

Abstract

Characterization of a grapevine R2R3-MYB transcription factor that regulates the phenylpropanoid pathway. Deluc, Laurent; Barrieu, Francois; Marchive, Chloe; Lauvergeat, Virginie; Decendit, Alain; Richard, Tristan; Carde, Jean-Pierre; Merillon, Jean-Michel; Hamdi, Said. Unite Mixte de Recherche 619, Physiologie et Biotechnologie Vegetales, Institut National de la Recherche Agonomique, Centre de Recherche de Bordeaux, Universite Bordeaux 1, Universite Bordeaux 2, Villenave d'Ornon, Fr. Plant Physiology (2006), 140(2), 499-511. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 145:24170 AN 2006:349173 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

US 2004-611020P P 20040917Priority Application


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW

WO 2006030322 A3 20060629WO 2006030322 A2 20060323 WO 2005-IB3591 20050913Patent No. Kind Date Application No. Date Patent Family Information

Bronchodilators and anti-inflammatory activity of flavone/flavanone derivatives. Kroeger, Edwin A. (University of Manitoba, Can.). PCT Int. Appl. (2006), 17 pp. CODEN: PIXXD2 WO 2006030322 A2 20060323 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2005-IB3591 20050913. Priority: US 2004-611020 20040917. CAN 144:324843 AN 2006:332240 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Structural analogs (flavanone: 2-4 and flavone: 5 and 6, resp.) of silybin (1a) were synthesized and tested for inhibitory activity on O⋅-2 release and PKC translocation in PMA-stimulated neutrophils as well as xanthine oxidase activity in order to identify the mol. structures responsible for the antioxidant property of silybin. Concerning the prevention of hem-mediated oxidative modification of LDL by silybin, the hydroxyl radical scavenging activity of its structural analogs was also detd. We demonstrated that the basic skeleton of 1a (4) is responsible for its inhibitory activity on O⋅-2 release in PMA-stimulated neutrophils via inhibition of PKC translocation, since introduction of a double bound and hydroxyl groups at C-5 and C-7 position (5 and 6) did not result in further increase in inhibition of O⋅-2 release. It has been shown that the presence of the phenolic hydroxyl group at C-5 and C-7 of 1a is essential for the inhibition of xanthine oxidase activity. Moreover, introduction of a double bond into the C-ring of 2 and 3, resulting in flavone derivs. (5 and 6), markedly enhanced the antioxidant effect in all the tested systems. Finally, silybin (1a) and its flavone derivs. (5 and 6) directly scavenged hydroxyl radicals as well. On the basis of these results it might be concluded that different moiety of silybin is responsible for inhibition of overprodn. of O⋅-2 in stimulated neutrophils, xanthine oxidase activity, and for prevention of hem-mediated oxidative modification of LDL.

Abstract

Nagy, E.; Ujhelyi, L.; Balla, G.; Balla, J.; Antus, S. Division of Nephrology, First Department of Medicine, Hung. Phytomedicine (2006), 13(1-2), 85-93. Publisher: Elsevier GmbH, CODEN: PYTOEY ISSN: 0944-7113. Journal written in English. CAN 145:465137 AN 2006:334696 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Phytoestrogens are increasingly consumed in artificially high doses as herbal prepns. and nutritional supplements. The flavanone 8-prenylnaringenin (8PN) is a potent phytoestrogen, but its benefits and risks after long-term application are poorly identified. Therefore, we tested two doses of 8PN and 17β-estradiol-3-benzoate (E2B) (EDs: 6⋅8 and 68⋅4 mg/kg body wt. (BW) of 8PN, and 0⋅17 and 0⋅7 mg/kg BW of 17β-estradiol (E2)) and compared their effects on uterine wt., pituitary hormones (LH, FSH and prolactin) and the expression of estrogen-regulated genes and of estrogen receptor (ER)α and ERβ in the hypothalamus, pituitary and uterus. Both doses of E2 and the high dose of 8PN suppressed serum LH and FSH, and stimulated serum prolactin levels, uterine wt., and progesterone receptor, insulin-like growth factor I and complement protein C3 mRNA transcripts. In the preoptic and the mediobasal areas of the hypothalamus, all treatments had negligible effects on ERα and ERβ and gonadotropin-releasing hormone (GnRH) receptor gene expression, while ERβ and GnRH receptor transcripts in the anterior pituitary were reduced under both E2 doses and the high 8PN dose. The mRNA concns. of the LHα and -β subunits in the pituitary were suppressed by E2 and 8PN. In summary, 8PN

Abstract

Effects of 8-prenylnaringenin on the hypothalamo-pituitary-uterine axis in rats after 3-month treatment. Christoffel, J.; Rimoldi, G.; Wuttke, W. Division of Clinical and Experimental Endocrinology, Department of Obstetrics and Gynecology, University of Goettingen, Goettingen, Germany. Journal of Endocrinology (2006), 188(3), 397-405. Publisher: Society for Endocrinology, CODEN: JOENAK ISSN: 0022-0795. Journal written in English. CAN 144:425637 AN 2006:326047 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The stereoisomeric sepn. of several flavanones and flavanone-7-O-glycosides was achieved with capillary electrophoresis by adding native cyclodextrins or cyclodextrin derivs. to the background electrolyte. As an alternative method, micellar electrokinetic chromatog. with sodium cholate as a chiral surfactant was used for the epimeric sepn. of two flavanone-7-O-glycosides. The effect of buffer systems contg. mixts. of cyclodextrin with either sodium dodecyl sulfate or sodium cholate upon the chiral recognition of flavanones and flavanone-7-O-glycosides as well as the variation of the background electrolyte (concn. of buffer and surfactant, pH value, org. modifier), and its influence on the resoln. factor Rs was studied. Temp.- and pH-dependent enantiomerization or epimerization barriers of several flavanones (naringenin, homoeriodictyol) and flavanone-7-O-glycosides (naringin, neohesperidin, prunin, narirutin) in basic media (pH values of 9-11) were obsd. Interconversion profiles featuring characteristic plateau formation of the elution pattern were obsd. at high pH and evaluated with the simulation software ChromWin to det. rate consts. k(T) and Eyring activation parameters, ΔG#(T), ΔH#, and ΔS#.

Abstract

Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers. Wistuba, Dorothee; Trapp, Oliver; Gel-Moreto, Nuria; Galensa, Rudolf; Schurig, Volker. Institut fuer Organische Chemie, Universitaet Tuebingen, Tuebingen, Germany. Analytical Chemistry (2006), 78(10), 3424-3433. Publisher: American Chemical Society, CODEN: ANCHAM ISSN: 0003-2700. Journal written in English. CAN 145:20108 AN 2006:326570 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Use of flavone/flavanone derivs. as bronchodilators and anti-inflammatory compds. to treat respiratory and nasal diseases. The bronchodilator activity of 30 mg/kg 3,3'-dihydroxyflavone at i.v. was shown in dogs.

Abstract


flavanone

Answer 470:

To elucidate the gene regulation of pigmentation in sweet potato, expressions of the genes involved in anthocyanin biosynthesis were investigated in correlation with the accumulation of the anthocyanins during plant development. Fragments of the anthocyanin biosynthetic pathway genes involved in the central flavonoid pathway, including those for chalcone synthase (CHS), chalcone isomerase (CHI), flavone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and UDPG-flavonoid-3-O-glucosyltransferase (UF3GT) were investigated in sweet potato, and their expressions were characterized in various tissues and developmental stages in both purple- and yellow-fleshed varieties. Transcription patterns of the anthocyanin biosynthetic genes show accumulation at the early stages of root development (10-30 d after planting), followed by a decline. The anthocyanin biosynthetic genes were expressed throughout all stages of root development, wherein their expressions were activated at the stages corresponding to anthocyanin accumulation. Quantification of total anthocyanin content in various sweet potato tissues showed that the anthocyanin content of the purple-fleshed variety was highly concd. in all root types except in the lateral roots, while in the yellow-fleshed variety, anthocyanin content was highest in the pigmented roots. The anthocyanin content at the different developmental stages of the sweet potato plant is highest during the early stages of development (10-30 d after planting), which is in accordance with the transcription levels of the anthocyanin biosynthetic genes.

Abstract

Temporal and spatial expression of genes involved in anthocyanin biosynthesis during sweet potato (Ipomoea batatas [L.[ Lam.) root development. Lalusin, Antonio G.; Ohta, Masaru; Fujimura, Tatsuhito. Laboratory of Plant Genetic Engineering, Graduate School of Life and Environmental Sciences, University of Tsukuba, Tennoudai 1-1-1, Tsukuba City, Ibaraki, Japan. International Journal of Plant Sciences (2006), 167(2), 249-256. Publisher: University of Chicago Press, CODEN: IPLSE2 ISSN: 1058-5893. Journal written in English. CAN 145:392622 AN 2006:313043 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavindogenide, 3-(4-fluorobenzylidene)flavanone was reacted with six 5-substituted 2-aminobenzenethiols, the substituents being F, Cl, Br, Me, MeO, and EtO, to obtain a series of 10-substituted 6a,7-dihydro-6H-7-(4-fluorophenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines. The products are characterized by elemental anal. and IR, 1H NMR, 19F NMR, and mass spectra. The synthesized compds. showed antimicrobial activity against the bacteria Escherichia coli and GFC (Alteromonas tetraodonis, a new Gram-neg. bacteria family) and fungi, Aspergillus niger, A. flavus and Curvularia lunata.

Abstract

Synthesis of 1,5-benzothiazepines. Part XXX. Synthesis and antimicrobial studies of 10-substituted 6a,7-dihydro-6H-7-(4-fluorophenyl)-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines. Pant, Umesh C.; Chandra, Hem; Goyal, Shweta; Sharma, Priyanka; Pant, Seema. Department of Chemistry, University of Rajasthan, Jaipur, India. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2006), 45B(3), 752-757. Publisher: National Institute of Science Communication and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 146:7737 AN 2006:320818 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


had very similar though milder effects than E2 on all tested parameters. Inhibition of climacteric complaints by E2 takes place in the hypothalamus, where it inhibits the overactive GnRH pulse generator. Hence, 8PN may be used to inhibit climacteric symptoms effectively. Human pharmacol. studies will show whether the stimulatory effect on the uterus that was found in the present animal model would require the concomitant administration of progestins to prevent endometrial overstimulation.


flavanone

Proteomic screening of strawberry (Fragaria ananassa) yielded a 58% success rate in protein identification in spite of the fact that no genomic sequence is available for this species. This was achieved by a combination of MALDI-MS/MS de novo sequencing of

Abstract

Down-regulation of the strawberry Bet v 1-homologous allergen in concert with the flavonoid biosynthesis pathway in colorless strawberry mutant. Hjernoe, Karin; Alm, Rikard; Canback, Bjorn; Matthiesen, Rune; Trajkovski, Karin; Bjork, Lars; Roepstorff, Peter; Emanuelsson, Cecilia. Department of Biochemistry and Molecular Biology, University of Southern Denmark, Odense, Den. Proteomics (2006), 6(5), 1574-1587. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: PROTC7 ISSN: 1615-9853. Journal written in English. CAN 144:466924 AN 2006:281906 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effect of the surface basicity of MgO on the heterogeneous synthesis of flavanone from benzaldehyde and 2'-hydroxyacetophenone was examd. through a series of MgO samples modified with different anions. CO2 temp. programmed desorption (TPD) was used to characterize the basic properties of these samples. The results indicate that basic sites with different strengths exist on the MgO surface. Introduction of different anions completely eliminates the weak basic sites (i.e., those desorbing CO2 in the 300-420 K range) and reduces substantially the no. of medium strength sites (i.e., those desorbing CO2 in the 420-650 K range). In contrast, no substantial effect was obsd. - with the exception of the chloride-treated sample - on the stronger basic sites (i.e., those desorbing CO2 above 650 K). A strong correlation was obsd. between the no. of basic sites of "medium" strength and the catalytic activity of these samples for the heterogeneous synthesis of flavanone. These sites are most likely involved in the activation of 2'-hydroxyacetophenone for the Claisen-Schmidt condensation with benzaldehyde, which represents the first step in the synthesis of flavanone.

Abstract

Effect of basic properties of MgO on the heterogeneous synthesis of flavanone. Liu, Zheng; Cortes-Concepcion, Jose A.; Mustian, Michael; Amiridis, Michael D. Department of Chemical Engineering, University of South Carolina, Columbia, SC, USA. Applied Catalysis, A: General (2006), 302(2), 232-236. Publisher: Elsevier B.V., CODEN: ACAGE4 ISSN: 0926-860X. Journal written in English. CAN 144:488425 AN 2006:282547 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. The present research status, the synthesizing and testing methods, pharmacol. functions on some metallic complexes of flavanones were reviewed in this paper.

Abstract

Research progress in the chemistry of metallic complexes of flavanones. Zhao, Bing; Xu, Qing-hai; Duan, Li-ying. Sch. Pharmaceutical Eng., Shenyang Pharmaceutical Univ., Shenyang, Peop. Rep. China. Huaxue Shiji (2006), 28(3), 141-143. Publisher: Huaxue Shiji Bianjibu, CODEN: HUSHDR ISSN: 0258-3283. Journal; General Review written in Chinese. CAN 144:424987 AN 2006:308515 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


O

O

HO

OH

O

O

HO

OMe

Me

Me

MeR3

I

II

A facile and efficient approach to the synthesis of prenylated flavonoids as potential chemopreventive agents was described. This features the synthesis of prenyl halide, prenylation of p-hydroxybenzaldehyde, formation of prenylated polyhydroxychalcone and cyclization of prenylated polyhydroxychalcone to (±)-abyssinone II I (R3 = H), abyssinone cyclic analog II and flavanol I (R3 = OH) starting from isoprene. The structures of all three compds. were characterized by NMR, IR and mass spectroscopy and (±)-abyssinone II was assayed for aromatase inhibition.

Abstract

Synthesis of Abyssinone II and related compounds as potential chemopreventive agents. Moriarty, Robert M.; Grubjesic, Simonida; Surve, Bhushan C.; Chandersekera, Susantha N.; Prakash, Om; Naithani, Rajesh. Department of Chemistry, University of Illinois at Chicago, Chicago, USA. European Journal of Medicinal Chemistry (2006), 41(2), 263-267. Publisher: Elsevier B.V., CODEN: EJMCA5 ISSN: 0223-5234. Journal written in English. CAN 144:467925 AN 2006:274159 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


double-derivatized peptides and indel-tolerant searching against local protein databases built on both EST and full-length nucleotide sequences. The amino acid sequence of a strawberry allergen, homologous to the well-known major birch pollen allergen Bet v 1, was partially detd. This strawberry allergen, named Fra a 1 according to the nomenclature for allergen proteins, showed sequence identity of 54 and 77%, resp., with corresponding allergens from birch and apple. Differential expression, as evaluated by 2-D DIGE, occurred in 10% of protein spots when red strawberries were compared to a colorless (white) strawberry mutant. White strawberries, known to be tolerated by individuals affected by allergy, were virtually free from the strawberry allergen. Also several enzymes in the pathway for biosynthesis of flavonoids, to which the red color pelargonidin belongs, were down-regulated. This approach to assess differential protein expression without access to genomic sequence information can also be applied to other crop plants and phenotypic traits.


flavanone

Inhibitory effect of ponciretin on Helicobacter pylori VacA toxin-induced vacuolation in HeLa cells. Kim, Jong-Mi; Shin, Ji-Eun; Bae, Eun-Ah; Han, Myung Joo; Kim, Dong-Hyun. College of Pharmacy, Kyung Hee University, Seoul, S. Korea. Journal of Microbiology and Biotechnology (2006), 16(1), 46-51. Publisher: Korean Society for Microbiology and Biotechnology, CODEN: JOMBES ISSN: 1017-7825. Journal written in English. CAN 145:180272 AN 2006:251887 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The concns. of metabolites in human plasma after ingestion of flavanone glycosides (FG) and their aglycons (FA) in lemon were examd. FG consisting abundantly of eriocitrin were prepd. from lemon peel and FA consisting abundantly of eriodictyol were prepd. from FG by treatment with β-glucosidase. Eriodictyol, homoeriodictyol, and hesperetin in plasma up to 4 h after ingestion of FG with water or FA with water by subjects were not detected in plasma of non-enzyme treatment but in plasma after treatment with β-glucronidase and sulfatase. Metabolites in plasma after ingestion of FG and FA in humans were shown to exist as the glucuro- and/or sulfo-conjugates of eriodictyol, homoeriodictyol, and hesperetin. After ingestion of FA, the concn. of metabolites in plasma exhibited a high max. peak at 1 h. The AUC (area under the blood concn. time curve) level of metabolites of FA was higher than that of FG. FA were suggested to be absorbed faster and in higher amts. than FG. The AUC of metabolites in subject plasma after ingestion of FG with flavonoid-depleted lemon juice was shown to change to a low level in comparison with that of FG with water. The max. concn. peak of metabolites in plasma was faster at 0.5 h than FA with water but the AUC level was similar to FA with water, when subjects ingested FA with vodka (40% ethanol). The absorption hour of FG and FA was shown to be affected by the co-existing soln.

Abstract

Difference in plasma metabolite concentration after ingestion of lemon flavonoids and their aglycones in humans. Miyake, Yoshiaki; Sakurai, Chika; Usuda, Mika; Fukumoto, Syuichi; Hiramitsu, Masanori; Sakaida, Kazuhiro; Osawa, Toshihiko; Kondo, Kazuo. Faculty of Human Wellness, Tokaigakuen University, Nagoya, Japan. Journal of Nutritional Science and Vitaminology (2006), 52(1), 54-60. Publisher: Center for Academic Publications Japan, CODEN: JNSVA5 ISSN: 0301-4800. Journal written in English. CAN 144:273500 AN 2006:256931 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effect of various natural flavonoids, cinnamic acid derivs., and a series of synthetic flavones on cell proliferation was evaluated in vitro in a panel of established human and murine tumor cell lines. The most potent antiproliferative agents were caffeic acid Bu ester (12) > 2'-nitroflavone (26) > caffeic acid Et ester (11) .apprx. 2',6-dinitroflavone (27) > apigenin (3) > 3'-bromoflavone (20) .apprx. 2'-fluoro-6-bromoflavone (31). Some compds. showed a moderate effect, the order of cytotoxic activities being chrysin (2) > 2'-fluoro-6-chloroflavone (30) .apprx. 2'-chlorochrysin (32) > α-naphthoflavone (7) > β-naphthoflavone (8) .apprx.6-chloroflavone (14) .apprx. 6-bromoflavone (15) .apprx. 4'-nitroflavone (23). A structure-activity relationship anal. of each group of compds. was performed. None of the natural or synthetic compds. tested affected the proliferation of epithelial cells derived from normal mammary gland of mice or fibroblastic cells from mouse embryo, suggesting a selective action against tumor cells.

Abstract

Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines. Cardenas, Mariano; Marder, Mariel; Blank, Viviana C.; Roguin, Leonor P. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica Biologicas (UBA-CONICET), Buenos Aires, Argent. Bioorganic & Medicinal Chemistry (2006), 14(9), 2966-2971. Publisher: Elsevier B.V., CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 144:460302 AN 2006:263188 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Purposes of this paper were to prep. and study new drug delivery systems for both flavanone glycosides and their aglycons based on solid-dispersion systems. These compds. are poor water sol. drugs, so an enhancement of their dissoln. is a high priority. Solid-dispersion systems were prepd. using PVP, PEG and mannitol as drug carrier matrixes. Characterizations of these dispersions were done by differential scanning calorimeter (DSC) and x-ray diffraction (XRD). The glass transition (Tg) temp. of PVP was only recorded in the DSC thermograms of PVP solid-dispersions of both flavanone glycosides and their aglycons, while in case of PEG and mannitol solid-dispersions endotherms of both glycosides and aglycons were noticed with low peak intensity, indicating that high percent of drug is in amorphous state. The XRD patterns of all PVP solid-dispersions of aglycons show typical amorphous materials,

Abstract

Thermal analysis study of flavonoid solid dispersions having enhanced solubility. Kanaze, F. I.; Kokkalou, E.; Niopas, I.; Georgarakis, M.; Stergiou, A.; Bikiaris, D. Department of Pharmacy, School of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki, Greece. Journal of Thermal Analysis and Calorimetry (2006), 83(2), 283-290. Publisher: Springer, CODEN: JTACF7 ISSN: 1388-6150. Journal written in English. CAN 144:337781 AN 2006:232700 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The antioxidative properties of five prenylated flavonoids, including new flavanone (2), from the root bark of Cudrania tricuspidata were examd. against the ABTS, DPPH, and hydroxyl radicals. In most of the assays to det. their antioxidative properties, the ABTS activity was strongly correlated with DPPH because both methods are responsible for the same chem. property of hydrogen- or electron-donation to the antioxidant. On the other hand, the prenylated flavonoids (1-5) acted differently with both methods; namely, all the prenylated flavonoids strongly scavenged the ABTS radical (IC50 < 10 μM), while they were inactive against the DPPH radical (IC50 > 300 μM). Even though isolated 5,7,2',4',-tetrahydroxy-6,5'-diprenylflavanone (3) showed weak reducing power (746 mV) by cyclic voltammetry when compared to quercetin (394 mV), both had similar ABTS activity (IC50 < 5 μM).

Abstract

Selective ABTS radical-scavenging activity of prenylated flavonoids from Cudrania tricuspidata. Lee, Byong Won; Lee, Jin Hwan; Gal, Sang Wan; Moon, Yea Hwang; Park, Ki Hun. Division of Applied Life Science (BK21 Program), Department of Agricultural Chemistry, Institute of Agriculture & Life Sciences, Gyeongsang National University, Jinju, S. Korea. Bioscience, Biotechnology, and Biochemistry (2006), 70(2), 427-432. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 145:206376 AN 2006:240911 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The inhibitory effects of flavanone derivs. on Helicobacter pylori (HP) growth, infection and VacA toxin-induced vacuolation were investigated. Among flavanones tested, ponciretin potently inhibited the growth of HP with a MIC value of 0.01 mg/mL and VacA toxin-induced vacuolation in HeLa cells with IC50 value of 0.078 mM. However, other flavanones inhibited neither HP growth nor VacA toxin-induced vacuolation. All flavanones tested did not inhibit HP infection to KATO III cells. Ponciretin also inhibited activation of procaspase-3 to caspase-3 in HeLa cell induced by HP VacA toxin, but did not affect Bax and Bcl-2 protein levels. These findings indicate that ponciretin inhibits growth as well as vacuolation by HP VacA toxin, which induces cell death via proteolytic activation of a cascade of caspases.

Abstract


flavanone

Answer 481:

A new nonlinear partial least squares algorithm embedded least squares support vector machine (LSSVM) into the regression framework of partial least squares(PLS) method was proposed. In this approach, LSSVM was used to fit the nonlinear inner relations between PLS components, thus a multi-input multi-output nonlinear modeling task was decompd. into linear outer relations and simple nonlinear inner relations that were performed by a no. of single-input single-output LSSVM models. By using the universal approxn. property of LSSVM, the PLS modeling method was generalized to a non-linear framework. Subsequently, to increase PLS components interpretative capability, the error-based wts. updating procedure in the PLS input outer model was deduced and implemented in the LSSVM-PLS regression framework. Finally, the EB-LSSVM-PLS was applied to quant. structure-activity relationships modeling of flavanone compd. Compared with the other three approach partial-east squares regression (PLSR), EB-neural network (NN) PLS and LSSVM, the EB-LSSVM-PLS approach has better prediction performance and stability.

Abstract

Error-based nonlinear partial least squares method embedded least squares support vector machine and its application to quantitative structure-activity relationships. Li, Jian; Chen, Dezhao; Cheng, Zhong; Ye, Ziping. Department of Chemical Engineering, Zhejiang University, Hangzhou, Peop. Rep. China. Fenxi Huaxue (2006), 34(2), 263-266. Publisher: Kexue Chubanshe, CODEN: FHHHDT ISSN: 0253-3820. Journal written in Chinese. CAN 144:266504 AN 2006:223751 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Monolithic capillary columns contg. native silica were modified by in situ coating with amylose tris(3,5-dimethylphenylcarbamate) and applied for enantiosepns. in capillary liq. chromatog. Capillary columns were examd. for 10 std. racemic compds. to compare the performance of monolithic silica columns with the common, 4.6 mm I.D. HPLC columns packed with particulate silica. The effects of polysaccharide coating and of the linear velocity of the mobile phase on peak performance were studied. Enantiosepns. with an anal. time <1 min were achieved for some chiral analytes.

Abstract

High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified with amylose tris(3,5-dimethylphenylcarbamate). Chankvetadze, Bezhan; Yamamoto, Chiyo; Kamigaito, Masami; Tanaka, Nobuo; Nakanishi, Kazuki; Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, Georgia. Journal of Chromatography, A (2006), 1110(1-2), 46-52. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 144:460010 AN 2006:228895 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


but XRD patterns of their glycosides reveal the presence of cryst. material. However, in all solid dispersions shifts in Tg of PVP as well as Tm of PEG were obsd., indicating the existence of some interactions between drugs and matrixes. SEM and TEM microscopy revealed that PVP/aglycon flavanone compds. are nanodispersed systems while all the other solid dispersions are microcryst. dispersions. The soly. of both flavanone glycosides and their aglycons was directly affected by the new phys. state of solid dispersions. Due to the amorphous drug state or nano-dispersions in PVP matrixes, the soly. was enhanced and found to be 100% at pH 6.8 in the nano-dispersion contg. 20 mass% of aglycons. Also soly. enhancement was occurred in solid dispersions of PEG and mannitol, but it was lower than that of PVP nano-dispersions due to the presence of the drug compds. in cryst. state in both matrixes.


flavanone

Two new dihydroflavanoids from Patrinia villosa Juss. Peng, Jin Yong; Fan, Guo Rong; Wu, Yu Tian. Shanghai Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep. China. Chinese Chemical Letters (2006), 17(2), 218-220. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN:


Evolutionary adaptations require genetic variation in the traits concerned. Mountain birch populations suffer from regular autumnal moth defoliations that affect tree survival and growth. Earlier studies have found that birch individuals show clear differences in their leaf chem., which may be relevant to herbivore performance. A large part of this variation is assumed to be genetic, since quant. differences between trees remain the same in different years. The authors estd. the genetic parameters of several herbivory-related chem. compds. The material consisted of 30 mature wild trees and their progenies. The authors treated the data both as half-sib and full-sib families, and calcd. parent-offspring comparisons as well. The compds. included 12 individual phenolics, 5 carbohydrates and 16 protein-bound amino acids. For comparison, the authors also analyzed the wt. and germination percent of seeds and the height of seedlings. Two of the most abundant phenylpropanoids (chlorogenic acid and kaempferol-3-O-α-L-rhamnopyranoside) showed significant genetic variation, but this was not true of all individual phenolic compds. Amino acids had less genetic variation than phenolic compds. The high genetic variation of the phenolic compds. indicates that the mountain birch is able to evolve its phenol-based resistance.

Abstract

Additive genetic variation of secondary and primary metabolites in mountain birch. Haviola, Sanna; Saloniemi, Irma; Ossipov, Vladimir; Haukioja, Erkki. Dept of Biology, Univ. of Turku, Turku, Finland. Oikos (2006), 112(2), 382-391. Publisher: Blackwell Publishers Ltd., CODEN: OIKSAA ISSN: 0030-1299. Journal written in English. CAN 146:23564 AN 2006:219232 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Citrus peel is rich in flavanone glycosides and polymethoxyflavones. In view of their importance for industrial application as well as for their pharmacol. properties, their content was analyzed in the mature fruits of several C. paradisi (grapefruit) and C. sinensis (orange) varieties, with a view to select the most interesting for isolation. The results shows that the Star Ruby grapefruit and the Sanguinelli orange stand out for their high contents of naringin and hesperidin, resp. The presence of the polymethoxyflavones nobiletin, heptamethoxyflavone and tangeretin, could be ascertained in all the grapefruit varieties analyzed. Higher polymethoxyflavone levels were recorded in orange, with Valencia Late showing the greatest nobiletin, sinensetin and tangeretin contents and Navelate the highest heptamethoxyflavone levels. An in vitro study revealed that these compds. acted as antifungal agents against Penicillium digitatum, the polymethoxyflavones being more active than the flavanones in this respect. The possible participation of these phenolic compds. in the defense mechanism of Citrus against P. digitatum is discussed.

Abstract

Citrus paradisi and Citrus sinensis flavonoids: Their influence in the defense mechanism against Penicillium digitatum. Ortuno, A.; Baidez, A.; Gomez, P.; Arcas, M. C.; Porras, I.; Garcia-Lidon, A.; Del Rio, J. A. Departamento de Biologia Vegetal (Fisiologia Vegetal), Facultad de Biologia, Universidad de Murcia, Murcia, Spain. Food Chemistry (2006), 98(2), 351-358. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 145:6987 AN 2006:222311 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Two different heterologous expression systems, microsomal fractions of Saccharomyces cerevisiae and transgenic tobacco plants, were used to investigate the enzymic activities of flavonoid 3'-hydroxylase (GtF3'H) and flavone synthase II (GtFSII) homologues

Abstract

Heterologous Expression of Two Gentian Cytochrome P450 Genes can Modulate the Intensity of Flower Pigmentation in Transgenic Tobacco Plants. Nakatsuka, Takashi; Nishihara, Masahiro; Mishiba, Keiichiro; Yamamura, Saburo. Iwate Biotechnology Research Center, Kitakami, Iwate, Japan. Molecular Breeding (2006), 17(2), 91-99. Publisher: Springer, CODEN: MOBRFL ISSN: 1380-3743. Journal written in English. CAN 146:41986 AN 2006:194769 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH

OOH

HO

OO

O

HO

OHOH

PEG

I

Highly water sol. esters of scutellarin I with variable mol. wt. polyethylene glycol (PEG) were prepd. via PEGylation. The physicochem. properties and the stabilities under different conditions were investigated. By PEG modification, water soly. and desirable partition coeff. of scutellarin were greatly increased. The results showed that these conjugates were potential prodrugs for the oral delivery of scutellarin.

Abstract

Synthesis and characterization of PEG-scutellarin conjugates, a potential PEG ester prodrug for the oral delivery of scutellarin. Zhou, Qing Song; Jiang, Xue Hua; Yu, Jia Rui; Li, Ke Jia. West China School of Pharmacy, Sichuan University, Chengdu, Peop. Rep. China. Chinese Chemical Letters (2006), 17(1), 85-88. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 146:163331 AN 2006:218675 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new dihydroflavonoids were obtained from the traditional Chinese medicinal herb Patrinia villosa Juss. Their structures were elucidated as (2S)-5, 7, 2', 6'-tetrahydroxy-6, 8-di (γ, γ-dimethylallyl) flavanone (1) and (2S)-5, 7, 2', 6'-tetrahydroxy-6-lavandulylated flavanone (2) by spectroscopic methods including UV, IR, HR-TOF-MS, 1D NMR and 2D NMR techniques.

Abstract 1001-8417. Journal written in English. CAN 145:120524 AN 2006:218712 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, WO 2006020164 A1 20060223 WO 2005-US25346 20050715Patent No. Kind Date Application No. Date Patent Family Information

Skin lighting and antiaging compositions containing a flavonoid compound and vitamin B3. Chen, Minghua; Sun, Peiwen; Date, Akira; Yuyama, Etsuko; Bissett, Donald Lynn. (The Procter & Gamble Company, USA). PCT Int. Appl. (2006), 32 pp. CODEN: PIXXD2 WO 2006020164 A1 20060223 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2005-US25346 20050715. Priority: US 2004-590559 20040723. CAN 144:239242 AN 2006:167784 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonols are plant polyphenolic compds. that belong to the class of mols. collectively known as flavonoids. Because of their demonstrated health benefits towards a wide array of human pathol. conditions, a great interest has emerged for their biosynthesis from well-characterized microbial hosts. We present the functional expression in Escherichia coli of a plant P 450 flavonoid 3',5'-hydroxylase (F3'5'H) as a fusion protein with a P 450 reductase. This expression allowed metabolic engineering of E. coli to produce the flavonol kaempferol and the 3',4' B-ring hydroxylated flavonol quercetin from the p-coumaric acid precursor by simultaneously co-expressing the fusion protein with 4-coumaroyl:CoA-ligase (4CL), chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3β-hydroxylase (FHT) and flavonol synthase (FLS). Biosynthesis of the B-ring tri-hydroxylated flavonol myricetin from the engineered strains was accomplished when flavanones rather than phenylpropanoid acids were used as precursor mols. Cultivation of the recombinant strains in rich medium increased the synthesis of all flavonoids with the exception of myricetin. The present work opens the possibility of the future prodn. of several other hydroxylated flavonoid mols. in E. coli.

Abstract

Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Leonard, Effendi; Yan, Yajun; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, the State University of New York, Buffalo, NY, USA. Metabolic Engineering (2006), 8(2), 172-181. Publisher: Elsevier, CODEN: MEENFM ISSN: 1096-7176. Journal written in English. CAN 144:466608 AN 2006:181868 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


isolated from gentian petals. Recombinant GtF3'H expressed in yeast showed hydroxylation activities in the 3' position with several flavonoid substrates, while recombinant GtFSII was able to produce flavone from flavanone. GtF3' H-expressing transgenic tobacco plants showed a slight increase in anthocyanin content and flower color intensity, and conversion of the flavonol quercetin from kaempferol. On the other hand, GtFSII-expressing plants showed a remarkable redn. in anthocyanin content and flower color intensity, and addnl. accumulation of flavone, esp. luteolin derivs. We demonstrated that two cytochrome P450s from gentian petals have F3'H and FSII enzymic activities both in vitro and in vivo, and might therefore be useful in modification of flower color using genetic engineering.


flavanone

Background and Purpose: Flavonoids and phenolic acids are two groups of recently popular phytochems. The most concd. source of those plant polyphenols is propolis - a natural product made by honeybees. Material and Methods: In this paper we focus on the nonempirical structure-property anal. of a certain no. of flavonoids and phenolic acids, usually present in Croatian propolis. Using mol. modeling procedures, we investigated the relationships between structure and properties of these compds. Topol. indexes used for correlation anal. include Wiener index, W, valence connectivity index, χv, Balaban index, J, information-theoretic index, I, and Schultz Index, MTI. All indexes were calcd. using TAM software. Investigated physicochem. properties were mol. wt. (M.w.), van der Waals vol. (Vw) and lipophilicity (log P). Van der Waals vol. was calcd. according to the method described by Moriguchi and log P values were calcd. using ALOGPs program. Result and Conclusion: The best QSPR models were obtained using Wiener index and valence connectivity index. Together with the indexes mentioned above, information-theoretic index also showed good correlation with certain physicochem. properties.

Abstract

Quantitative modeling (QSPR) of flavonoids from Croatian propolis. Smolcic-Bubalo, Asja; Mornar, Ana; Jasprica, Ivona; Medic-Saric, Marica. Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia. Periodicum Biologorum (2005), 107(4), 457-464. Publisher: Hrvatsko Prirodoslovno Drustvo, CODEN: PDBIAD ISSN: 0031-5362. Journal written in English. CAN 145:204859 AN 2006:166704 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention is directed to a skin case compn. comprising: (1) from about 0.001% to about 10% of a flavonoid compd.; (2) from about 0.01% to about 15% of a vitamin B3 compd.; and (3) a dermatol. acceptable oil-in-water carrier comprising at least about 2% by wt. of the entire compn. of an oil component; wherein the compn. is substantially free of titanium dioxide. The present invention is also directed to a method of providing skin lightening benefit and anti-aging benefit comprising the steps of applying to the skin the aforementioned compn.

Abstract WO 2005-US25346 W 20050715US 2004-590559P P 20040723Priority Application JP 2008507523 T 20080313 JP 2007-522609 20050715


EP 1833456 A1 20070919 EP 2005-772259 20050715CN 1988879 A 20070627 CN 2005-80024942 20050715


DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


flavanone


Preparation of flavanone glycosides as immunosuppressant. Guo, Zijian; Yang, Xiaoliang; Xu, Qiang; Sun, Yang; Zhang, Zichao. (Nanjing University, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 20 pp. CODEN: CNXXEV CN 1594346 A 20050316 Patent written in Chinese. Application: CN 1004-1063 20040623. Priority: . CAN 144:192445 AN 2006:137981 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


by wt., suggesting that silibinin could be a major cell cycle-inhibitory component in silymarin. However, other silibinin stereoisomers present in silymarin also contribute to its efficacy, and could be of interest for future investigation.

Here, we assessed and compared the anticancer efficacy and assocd. mechanisms of silymarin and silibinin in human prostate cancer (PCA) PC3 cells; silymarin is comprised of silibinin and its other stereoisomers, including isosilybin A, isosilybin B, silydianin, silychristin and isosilychristin. Silymarin and silibinin (50-100 μg/mL) inhibited cell proliferation, induced cell death, and caused G1 and G2-M cell cycle arrest in a dose/time-dependent manner. Mol. studies showed that G1 arrest was assocd. with a decrease in cyclin D1, cyclin D3, cyclin E, cyclin-dependent kinase (CDK)4, CDK6 and CDK2 protein levels, and CDK2 and CDK4 kinase activity, together with an increase in CDK inhibitors (CDKIs) Kip1/p27 and Cip1/p21. Further, both agents caused cytoplasmic sequestration of cyclin D1 and CDK2, contributing to G1 arrest. The G2-M arrest by silibinin and silymarin was assocd. with decreased levels of cyclin B1, cyclin A, pCdc2 (Tyr15), Cdc2, and an inhibition of Cdc2 kinase activity. Both agents also decreased the levels of Cdc25B and cell division cycle 25C (Cdc25C) phosphatases with an increased phosphorylation of Cdc25C at Ser216 and its translocation from nucleus to the cytoplasm, which was accompanied by an increased binding with 14-3-3β. Both agents also increased checkpoint kinase (Chk)2 phosphorylation at Thr68 and Ser19 sites, which is known to phosphorylate Cdc25C at Ser216 site. Chk2-specific small interfering RNA largely attenuated the silymarin and silibinin-induced G2-M arrest. An increase in the phosphorylation of histone 2AX and ataxia telangiectasia mutated was also obsd. These findings indicate that silymarin and silibinin modulate G1 phase cyclins-CDKs-CDKIs for G1 arrest, and the Chk2-Cdc25C-Cdc2/cyclin B1 pathway for G2-M arrest, together with an altered subcellular localization of crit. cell cycle regulators. Overall, we obsd. comparable effects for both silymarin and silibinin at equal concns.

Abstract

Silymarin and silibinin cause G1 and G2-M cell cycle arrest via distinct circuitries in human prostate cancer PC3 cells: a comparison of flavanone silibinin with flavanolignan mixture silymarin. Deep, G.; Singh, R. P.; Agarwal, C.; Kroll, D. J.; Agarwal, R. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Sciences Center, Denver, CO, USA. Oncogene (2006), 25(7), 1053-1069. Publisher: Nature Publishing Group, CODEN: ONCNES ISSN: 0950-9232. Journal written in English. CAN 144:425253 AN 2006:143204 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 493:

A review, on the discovery of arom. prenyltransferases; biochem. anal. of arom. prenyltransferases; and cryst. structure anal. of ORF2. Arom. prenyltransferases.

Abstract

Aromatic prenyltransferases for creating natural products deversification. Kazuyama, Tomohisa; Kumano, Takuto; Nishiyama, Makoto. Research Center for Advanced Science and Technology, The University of Tokyo, Japan. Fain Kemikaru (2006), 35(2), 5-14. Publisher: Shi Emu Shi Shuppan, CODEN: FNKMAU ISSN: 0913-6150. Journal; General Review written in Japanese. CAN 146:57381 AN 2006:122035 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This paper presents the first report of a highly selective transformation of flavanones to 3-bromoflavones or flavones by microwave irradn. of the corresponding flavanone reactants and N-bromosuccinimide (NBS) in the presence of a catalytic amt. of 2,2'-azobis(isobutyronitrile) (AIBN). The combination of good to excellent yields, shorter reaction time (10 min), and high levels of functional group compatibility make this an attractive synthetic approach to 3-bromoflavones and flavones.

Abstract

A selective transformation of flavanones to 3-bromoflavones and flavones under microwave irradiation. Zhou, Zhongzhen; Zhao, Peiliang; Huang, Wei; Yang, Guangfu. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, Peop. Rep. China. Advanced Synthesis & Catalysis (2006), 348(1 + 2), 63-67. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: ASCAF7 ISSN: 1615-4150. Journal written in English. CAN 146:206122 AN 2006:127611 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

Ph

O

OOH

OH

OH

Me

I

Title compds., e.g. I, are prepd. by treating hydroxyflavanone with 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate or 2,3,4,6-tetraacetyl-D-glucopyranosyl trichloroacetimidate in CH2Cl2 in the presence of trimethylsilyl triflate at -42°--78° followed by deprotection with NH3 in MeOH. I was prepd. and showed immunosuppressant activity comparable to that of astilbin.


flavanone

Quant. resistance of chickpea (Cicer arietinum L.) to a necrotrophic fungal pathogen, Ascochyta rabiei (Pass) Labr., is conferred in a pathotype-dependent manner. Unlike race-specific or qual. resistance, identification of genetic factors for blight resistance is difficult because diverse pathogenic and environmental factors cause significant variation in resistance patterns. To identify genes assocd. with blight resistance in chickpea, the authors conducted bulk segregation anal. of differential transcript patterns between blight resistant and susceptible recombinant inbred lines (RILs) generated from a cross of PI 359075(1) (blight susceptible)×FLIP84-92C(2) (blight resistant). Constitutive expression of a cDNA-AFLP fragment homologous to flavanone 3-hydroxylase (F3H) was lower in RILs susceptible to pathotypes I and II of A. rabiei than in RILs resistant to both pathotypes. F3H was mapped to linkage group 5. Based

Abstract

Constitutive expression of the Flavanone 3-hydroxylase gene related to pathotype-specific ascochyta blight resistance in Cicer arietinum L. Cho, Seungho; Chen, Weidong; Muehlbauer, Fred J. School of Molecular Biosciences, Washington State University, Pullman, WA, USA. Physiological and Molecular Plant Pathology (2006), Volume Date 2005, 67(2), 100-107. Publisher: Elsevier B.V., CODEN: PMPPEZ ISSN: 0885-5765. Journal written in English. CAN 146:1261 AN 2006:104962 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A host cell producing a chalcone synthase (CHS) and a 4-coumarate CoA: ligase (4CL) in which one or both are heterologous to the cell is disclosed. A method of enabling benzalacetone synthase activity of a CHS protein comprises exposing the CHS to a microbial cellular environment, preferably an E. coli cell. The benzalacetone may be reduced by benzalacetone reductase (BAR) in the bacterial cell to make raspberry ketone. The host cell may be supplied with a raspberry ketone precursor, preferably benzalacetone or p-coumaric acid. Sequences of raspberry CHS, tobacco 4CL and raspberry BAR genes and polypeptides are described as are vectors comprising CHS and 4CL sequences, preferably in combination with a PAL (phenylalanine ammonia-lyase) gene or a cinnamic acid 4-hydroxylase (C4H) gene. The invention is based on the surprising discovery that chalcone synthase has benzalacetone synthase (BAS) activity. Thus, transgenic E. coli expressing raspberry CHS cDNA and tobacco 4CL cDNA produced raspberry ketone from coumaric acid. A no. of other CHS cDNA's, e.g., those of grape, Medicago, Arabidopsis, snapdragon, maize, and parsley, could be substituted for the raspberry CHS cDNA.

Abstract GB 2004-16845 20040728Priority Application GB 2416770 A 20060208 GB 2004-16845 20040728 Patent No. Kind Date Application No. Date Patent Family Information

Synthesis of raspberry ketone by bacteria expressing heterologous chalcone synthase gene. Beekwilder, Martinus Julius; Sibbesen, Ole; Mikkelsen, Jurn Dalgaard; Van Der Meer, Ingrid Maria; Hall, Robert David; Qvist, Ingmar. (Danisco A/S, Den.). Brit. UK Pat. Appl. (2006), 113 pp. CODEN: BAXXDU GB 2416770 A 20060208 Patent written in English. Application: GB 2004-16845 20040728. Priority: . CAN 144:190713 AN 2006:113619 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

JP 2006-518817 A3 20040701WO 2006-US8290 W 20060307US 2005-74374 A 20050307US 2004-884879 A2 20040702US 2004-884022 A2 20040701US 2003-532158P P 20031223US 2003-483949P P 20030701Priority Application JP 2007326872 A 20071220 JP 2007-203287 20070803


EP 1863461 A2 20071212 EP 2006-737459 20060307



WO 2006096780 A3 20070118WO 2006096780 A2 20060914 WO 2006-US8290 20060307CA 2599125 A1 20060914 CA 2006-2599125 20060307AU 2006220554 A1 20060914 AU 2006-220554 20060307US 20050136537 A1 20050623 US 2004-884879 20040702US 20050096256 A1 20050505 US 2004-884022 20040701US 20060025337 A1 20060202 US 2005-74374 20050307Patent No. Kind Date Application No. Date Patent Family Information

Sirtuin related therapeutics and diagnostics for neurodegenerative diseases. Sinclair, David A.; Tsai, Li-Huei; Nguyen, Minh Dang; Howitz, Konrad T.; Zipkin, Robert E.; Bitterman, Kevin J. (President and Fellows of Harvard College, USA). U.S. Pat. Appl. Publ. (2006), 163 pp., Cont.-in-part of U.S. Ser. No. 884,022. CODEN: USXXCO US 2006025337 A1 20060202 Patent written in English. Application: US 2005-74374 20050307. Priority: US 2003-483949 20030701; US 2003-532158 20031223; US 2004-884022 20040701; US 2004-884879 20040702. CAN 144:184697 AN 2006:104637 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


on expression pattern of F3H between resistant and susceptible RIL bulks, F3H or its genomic vicinity on linkage group 5 was thought to be related to blight resistance in chickpea. Further study is required to validate the genetic role of F3H and its genomic vicinity on linkage group 5 in blight resistance in chickpea.


flavanone


MITF gene expression promoting agents for the prevention of gray hair. Izuta, Tatsuo; Takeda, Shunsuke; Tajima, Masahiro. (Shiseido Co., Ltd., Japan; Kirin Brewery Co., Ltd.). Jpn. Kokai Tokkyo Koho (2006), 21 pp. CODEN: JKXXAF JP 2006028143 A 20060202 Patent written in Japanese. Application: JP 2004-213569 20040721. Priority: . CAN 144:156165 AN 2006:99909 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Metabolic energy capacity enhancing compns. and methods for reducing oxidative stress and improving vitality in a mammal are disclosed. A compn. for increasing metabolic energy capacity may be in a palatable liq. formulation or a solid dosage form and typically includes an anti-oxidant contg. phytonectar and an energy catalyst. An anti-oxidant may include a polyphenol, anthocyanin, bioflavonoid, proanthocyanidin, and a xanthone. An energy catalyst may include a mineral, vitamin, co-vitamin, carbohydrate and a lipid. In a presently preferred embodiment a compn. includes phytonectar exts. from grape, aloe vera, apple, morinda citrifolia, scullcap, blueberry, prune, cranberry, elderberry, bilberry, and gentain and a mineral blend contg. calcium, magnesium, manganese, zinc, chromium, selenium, iron, copper, molybdenum, vanadium, potassium, iodine, and cobalt. A method for increasing metabolic energy capacity in a mammal may include consuming a chem. component having the ability to undergo oxidn., producing free radicals and administering a compn. having an anti-oxidant contg. phytonectar and an energy catalyst.

Abstract US 2004-900038 20040727Priority Application US 20060024385 A1 20060202 US 2004-900038 20040727 Patent No. Kind Date Application No. Date Patent Family Information

Metabolic capacity enhancing compositions and methods for use in a mammal. Pedersen, Mark A. (USA). U.S. Pat. Appl. Publ. (2006), 22 pp. CODEN: USXXCO US 2006024385 A1 20060202 Patent written in English. Application: US 2004-900038 20040727. Priority: . CAN 144:198854 AN 2006:103237 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Provided herein are methods and compns. for modulating the activity of sirtuin deacetylase protein family members; p53 activity; apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compd., such as a sphingolipid, e.g., sphingosine. Also disclosed herein are methods for treating, preventing or diagnosing a disease assocd. with neuronal cell death, e.g., a neurodegenerative disease.

Abstract


flavanone

Beech leaf colonization by the endophyte Apiognomonia errabunda dramatically depends on light exposure and climatic conditions. Bahnweg, G.; Heller, W.; Stich, S.; Knappe, C.; Betz, G.; Heerdt, C.; Kehr, R. D.; Ernst, D.; Langebartels, C.; Nunn, A. J.; Rothenburger, J.; Schubert, R.; Wallis, P.; Mueller-Starck, G.; Werner, H.; Matyssek, R.; Sandermann, H., Jr. GSF - National Research Centre for Environment and Health, Institute of Biochemical Plant Pathology, Neuherberg, Germany. Plant Biology (Stuttgart, Germany) (2005), 7(6), 659-669. Publisher: Georg Thieme Verlag, CODEN: PBIOFN ISSN: 1435-8603. Journal written in English. CAN 145:486025 AN 2006:96316 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Enhanced shoot growth and a decrease in flavonoid concn. in apple trees grown under high nitrogen (N) supply was obsd. in previous studies, along with increasing scab susceptibility of cultivar Golden Delicious after high N nutrition. Several hypotheses have suggested that there is a tradeoff between primary and secondary metab. because of competition for common substrates, but nothing is known about regulation at the enzyme level. In this study, a set of expts. was performed to elucidate the effect of N nutrition on the activities of key enzymes involved in flavonoid biosynthesis (phenylalanine ammonia-lyase [PAL], chalcone synthase/chalcone isomerase [CHS/CHI], flavanone 3-hydroxylase [FHT], flavonol synthase [FLS], dihydroflavonol 4-reductase [DFR]) and the accumulation of different groups of phenylpropanoids. The inhibition of flavonoid accumulation by high N nutrition could be confirmed, but the influence of N supply on the flavonoid enzymes CHS/CHI, FHT, DFR, and FLS was not evident. However, PAL activity seems to be down-regulated, thus forming a bottleneck resulting in a generally decreased flavonoid accumulation. Furthermore, the response of the scab-resistant cultivar Rewena to high N nutrition was not as strong as that of the susceptible cultivar Golden Delicious.

Abstract

Growth-promoting nitrogen nutrition affects flavonoid biosynthesis in young apple (Malus domestica Borkh.) leaves. Strissel, T.; Halbwirth, H.; Hoyer, U.; Zistler, C.; Stich, K.; Treutter, D. Department fuer Pflanzenwissenschaften, Fachgebiet Obstbau, Technische Universitaet Muenchen-Weihenstephan, Freising, Germany. Plant Biology (Stuttgart, Germany) (2005), 7(6), 677-685. Publisher: Georg Thieme Verlag, CODEN: PBIOFN ISSN: 1435-8603. Journal written in English. CAN 145:468069 AN 2006:96319 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Disclosed are MITF gene expression promoting agents comprising isomerized hop exts. or ≥ 1 compds. selected from the group consisting of chalcones, flavanones, and isohumulones. The MITF gene expression promoting agents stimulate the activities of melanocytes and prevent gray hair. For example, a hair cream for inhibiting gray hair contained isohumulone 0.001, stearyldimethylamineoxide 0.5, ethoxylated hydrogenated castor oil 1, 95 % ethanol 54.0, and ion-exchanged water balance to 100 %.

Abstract JP 2004-213569 20040721Priority Application JP 2006028143 A 20060202 JP 2004-213569 20040721 Patent No. Kind Date Application No. Date


flavanone

Abstract

A new route for the synthesis of flavanones from 2-methoxybenzoic acids. Lee, Jae In; Jung, Mi Gung. Department of Chemistry, College of Natural Science, Duksung Women's University, Seoul, S. Korea. Bulletin of the Korean Chemical Society (2005), 26(12), 2044-2046. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN: 0253-2964. Journal written in English. CAN 145:418835 AN 2006:85060 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Nuclear sequence variation and linkage disequil. (LD) were studied in 15 cold-hardiness- and 3 wood quality-related candidate genes in Douglas fir [Pseudotsuga menziesii (Mirb.) Franco]. This set of genes was selected on the basis of its function in other plants and collocation with cold-hardiness-related quant. trait loci (QTL). The single-nucleotide polymorphism (SNP) discovery panel represented 24 different trees from six regions in Washington and Oregon plus parents of a segregating population used in the QTL study. The frequency of SNPs was one SNP per 46 bp across coding and noncoding regions on av. Haplotype and nucleotide diversities were also moderately high with Hd = 0.827 ± 0.043 and π = 0.00655 ± 0.00082 on av., resp. The nonsynonymous (replacement) nucleotide substitutions were almost five times less frequent than synonymous ones and substitutions in noncoding regions. LD decayed relatively slowly but steadily within genes. Haploblock anal. was used to define haplotype tag SNPs (htSNPs). These data will help to select SNPs for assocn. mapping, which is already in progress.

Abstract

Nucleotide diversity and linkage disequilibrium in cold-hardiness- and wood quality-related candidate genes in Douglas fir. Krutovsky, Konstantin V.; Neale, David B. Institute of Forest Genetics, Pacific Southwest Research Station, U.S. Department of Agriculture Forest Service, Davis, CA, USA. Genetics (2005), 171(4), 2029-2041. Publisher: Genetics Society of America, CODEN: GENTAE ISSN: 0016-6731. Journal written in English. CAN 145:138538 AN 2006:88802 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Ozone and light effects on endophytic colonization by Apiognomonia errabunda of adult beech trees (Fagus sylvatica) and their putative mediation by internal defense compds. were studied at the Kranzberg Forest free-air ozone fumigation site. A. errabunda colonization was quantified by "real-time PCR" (QPCR). A. errabunda-specific primers allowed detection without interference by DNA from European beech and several species of common genera of plant pathogenic fungi, such as Mycosphaerella, Alternaria, Botrytis, and Fusarium. Colonization levels of sun and shade leaves of European beech trees exposed either to ambient or twice ambient ozone regimes were detd. Colonization was significantly higher in shade compared to sun leaves. Ozone exhibited a marginally inhibitory effect on fungal colonization only in young leaves in 2002. The hot and dry summer of 2003 reduced fungal colonization dramatically, being more pronounced than ozone treatment or sun exposure. Levels of sol. and cell wall-bound phenolic compds. were approx. twice as high in sun than in shade leaves. Acylated flavonol 3-O-glycosides with putatively high UV-B shielding effect were very low in shade canopy leaves. Ozone had only a minor influence on secondary metabolites in sun leaves. It slightly increased kaempferol 3-O-glucoside levels exclusively in shade leaves. The frequently prominent hydroxycinnamic acid deriv., chlorogenic acid, was tested for its growth inhibiting activity against Apiognomonia and showed an IC50 of approx. 8 mM. Appearance of Apiognomonia-related necroses strongly correlated with the occurrence of the stress metabolite, 3,3',4,4'-tetramethoxybiphenyl. Infection success of Apiognomonia was highly dependent on light exposure, presumably affected by the endogenous levels of constitutive phenolic compds. Ozone exerted only minor modulating effects, whereas climatic factors, such as pronounced heat periods and drought, were dramatically overriding.

Abstract


flavanone

Abstract WO 2005-US24525 W 20050711US 2004-586903P P 20040710Priority Application KR 2007035599 A 20070330 KR 2007-703269 20070209 JP 2008505657 T 20080228 JP 2007-521533 20050711


EP 1778850 A2 20070502 EP 2005-789029 20050711US 7338791 B2 20080304US 20060019334 A1 20060126 US 2005-178912 20050711CA 2573490 A1 20060126 CA 2005-2573490 20050711


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Production of flavonoids by recombinant microorganisms expressing plant metabolic pathway genes. Koffas, Mattheos; Leonard, Effendi; Yan, Yajun; Chemler, Joseph. (The Research Foundation of State University of New York, USA). PCT Int. Appl. (2006), 98 pp. CODEN: PIXXD2 WO 2006010117 A2 20060126 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NG, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2005-US24525 20050711. Priority: US 2004-586903 20040710. CAN 144:169672 AN 2006:79417 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Treatment of 2-methoxybenzoates with 2 equiv MeLi in THF at -78° yielded 2'-methoxyacetophenones. Subsequent enolization with LiN(CHMe2)2 and reaction with benzaldehydes afforded β-aryl-β-hydroxy-2'-methoxypropiophenones, which cyclized on dehydration of the β-OH and successive conjugate addn. of the phenolic OH generated by cleavage of the 2'-MeO using HBr/AcOH. Thus, various flavanones were synthesized in 38-62% yields.


flavanone

Answer 505:

We studied the effects of flavonoids, naringenin (flavanone), baicalein (flavone), kaempferol, quercetin, myricetin, morin, and fisetin (flavonols) as well as two glycosides of quercetin on P-glycoprotein (P-gp) function in multidrug-resistant P-gp overexpressing KB-C2 cells. Flavonoids such as kaempferol and quercetin increased the accumulation of rhodamine-123 dependent on their chem. structure. Anal. by flow cytometry indicated that the increase in substrate accumulation was due to the inhibition of substrate efflux. Naringenin, which lacks the 2,3-double bond in the C ring, had no effect, although it was more hydrophobic than myricetin, fisetin and morin. Therefore, the planar structure of the flavonoids seemed to be important for their interaction with P-gp. The effects of other flavonoids on the accumulation of daunorubicin were in the order of kaempferol >quercetin, baicalein >myricetin >fisetin, morin. Quercetin-3-O-glucoside and rutin had no effect. The order of the effects corresponded with that of the partition coeffs. Difference in the no. and position of hydroxyl groups in flavonoid mols. by themselves seemed to have little effect. These results suggested that hydrophobicity as well as planar structure is important for the inhibitory effects of flavonoids on P-gp-mediated transport.

Abstract

Structure-activity relationships of the inhibitory effects of flavonoids on P-glycoprotein-mediated transport in KB-C2 cells. Kitagawa, Shuji; Nabekura, Tomohiro; Takahashi, Tomoharu; Nakamura, Yutaka; Sakamoto, Hiromi; Tano, Hiromi; Hirai, Midori; Tsukahara, Go. Niigata University of Pharmacy and Applied Life Sciences, 5-13-2 Kamishin'el-cho, Niigata, Japan. Biological & Pharmaceutical Bulletin (2005), 28(12), 2274-2278. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 144:100385 AN 2006:66511 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids are important secondary metabolites in strawberry as they fulfill a wide variety of physiol. functions. In addn., they are beneficial for human health. Previous studies have shown for selected enzymes from the flavonoid pathway that flavonoid biosynthesis shows two peaks during fruit development. We provide optimized protocols for the detn. of the activities of the key flavonoid enzymes: phenylalanine ammonia lyase, chalcone synthase/chalcone isomerase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, flavonol synthase, flavonoid 3-O-glucosyltransferase, and flavonoid 7-O-glucosyltransferase. Using these protocols we were able to demonstrate two distinct activity peaks during fruit ripening at early and late developmental stages for all enzymes with the exception of flavonol synthase. The first activity peak corresponds to the formation of flavanols, while the second peak is clearly related to anthocyanin and flavonol accumulation. The results indicate that flavonoid 3-O-glucosyltransferase activity is not essential for redirection from flavanol to anthocyanin formation in strawberry.

Abstract

Two-Phase Flavonoid Formation in Developing Strawberry (Fragaria x ananassa) Fruit. Halbwirth, Heidrun; Puhl, Iva; Haas, Ursula; Jezik, Karoline; Treutter, Dieter; Stich, Karl. Institut fuer Verfahrenstechnik, Umwelttechnik und Technische Biowissenschaften, Technische Universitaet Wien, Vienna, Austria. Journal of Agricultural and Food Chemistry (2006), 54(4), 1479-1485. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 144:253082 AN 2006:72431 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Methods and compns. are provided for prodn. of flavonoids in microbial hosts. The compns. comprises a set of genes which encode for enzymes involved in one or more steps in the biosynthetic pathway for the conversion of phenylpropanoids to various flavonoids. The method comprises the steps of introducing the set of genes into a heterologous host cell, allowing growth of the cells in a suitable medium such that the expression of the genes results in prodn. of enzymes. When specific substrate(s) is/are provided to the transformed cell, the enzymes act on the substrate(s) to produce the desired flavonoids.


flavanone

Biosynthesis is well elucidated for 5-hydroxyflavonoids (phloroglucinol type), but for 5-deoxyflavonoids (resorcinol type) the knowledge is still limited. We provide detailed and optimized protocols for the synthesis of (14C)-labeled 6'-deoxychalcones, 5-deoxyflavanones, 5-deoxydihydroflavonols and 5-deoxyleucoanthocyanidins. With the exception of the formation of 6'-deoxychalcones, all steps were performed enzymically using enzymes normally involved in the formation of 5-hydroxyflavonoids. The availability of (14C)-labeled substrates will facilitate future work on the hitherto largely unknown biosynthesis of 5-deoxyflavonoids. In particular, the 5-deoxyleucoanthocyanidins, which are more stable than the corresponding 5-hydroxy compds., may provide excellent tools for investigating enzymes, which use the unstable 5-hydroxyleucoanthocyanidins as natural substrates. As a first example, the conversion of (14C)-labeled 5-deoxyleucoanthocyanidins to dihydroflavonols in the presence of NADP+ was shown. Studies with defined genotypes of Matthiola incana possessing or lacking dihydroflavonol 4-reductase activity and genetically modified yeast expressing the Matthiola enzyme confirmed that the reaction is catalyzed by the well-known dihydroflavonol 4-reductase, which catalyzes the conversion of dihydroflavonols to leucoanthocyanidins (forward reaction). Thus, the reverse reaction of dihydroflavonol 4-reductase could be demonstrated for the first time. The forward reaction shows an optimum at pH 6.25, the reverse reaction at pH 7.75. The impact of the results on the regulation of flavonoid accumulation is discussed.

Abstract

Synthesis of (14C)-labeled 5-deoxyflavonoids and their application in the study of dihydroflavonol/leucoanthocyanidin interconversion by dihydroflavonol 4-reductase. Halbwirth, Heidrun; Kahl, Stefan; Jaeger, Walter; Reznicek, Gottfried; Forkmann, Gert; Stich, Karl. Institut fuer Verfahrenstechnik, Umwelttechnik und Technische Biowissenschaften, Technische Universitaet Wien, Vienna, Austria. Plant Science (Amsterdam, Netherlands) (2006), 170(3), 587-595. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 145:182793 AN 2006:58561 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The aim of this study was to assess the ability of different wines - a sweet red, a dry red, a sweet white, and a dry white - to scavenge the stable 1,1'-diphenyl-2-picryl-hydrazyl radical (DPPH⋅) and to det. their phenolic compn. Both red wines contained, apart from anthocyanins, also higher concn. of total phenolics, tartaric esters, and flavonols than the two white wines. All wines exhibited scavenging activity analogous to their total phenolic content. However, their phenolics differed in antiradical potency, which was visible in their EC50 values. The dry red wine, Xinomavro, had a lower EC50 value, indicating the higher antiradical potency of its phenolics. The scavenging capacities of phenolic exts. from Xinomavro red wine on hydroxyl radicals, superoxide radicals, and singlet oxygen were also assessed. Wine total ext. was fractionated by extn., and each of the three fractions was then subfractionated by column chromatog. into two subfractions. Wine total ext., and its fractions and subfractions exhibited scavenging capacity on hydroxyl radicals, superoxide radicals, and singlet oxygen, indicating the activity of many wine phenolics. The most active wine exts. towards hydroxyl radicals were characterized by the high peaks of flavanols, anthocyanins and flavonols in their HPLC-DAD chromatograms. The most active ext. towards superoxide radicals was rich in flavanols and anthocyanins. The characteristic phenolics of the most active wine exts. towards singlet oxygen were flavanols, flavonols and phenolic acids. The ability of all red wine phenolic exts. to scavenge singlet oxygen, along with hydroxyl and superoxide radicals, emphasizes its health functionality.

Abstract

Scavenging capacities of some wines and wine phenolic extracts. Roussis, Ioannis G.; Lambropoulos, Ioannis; Soulti, Kalliopi. Laboratory of Food Chemistry, Department of Chemistry, University of Ioannina, Ioannina, Greece. Food Technology and Biotechnology (2005), 43(4), 351-358. Publisher: University of Zagreb, Faculty of Food Technology and Biotechnology, CODEN: FTBRFD ISSN: 1330-9862. Journal written in English. CAN 144:273102 AN 2006:66062 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


A review with new data. We previously identified astilbin as a hair growth promoter contained in Hypericum perforatum. In order to find a compd. that is safe and effective on hair growth, we made a lot of derivs. of taxifolin, the aglycon of astilbin and finally found trans-3,4'-dimethyl-3-hydroxyflavanone, t-flavanone. T-Flavanone promoted hair growth in C3H mouse assay, in rat vibrissa organ culture and in use test on male pattern baldness. To clarify the mechanism of the hair growth effect of t-flavanone, we focused on TGF-β that is considered as a catagen inducer and a crucial key mol. of male pattern baldness. In the co-culture system of keratinocytes and dermal papilla cells, t-flavanone decreased active-formed TGF-β2, however did not change the amt. of total TGF-β2. When keratinocytes were incubated with t-flavanone, their ability to activate TGF-β2 decreased. These results suggest that t-flavanone may affect on the TGF-β activating cascade and prevent the increase of active-formed TGF-β2. The redn. of TGF-β2 must extend the anagen period, so it can be an effective cure for many kind of balding disease. We tried the use test on women who were suffering from baldness, and verified that t-flavanone has efficacy on women's baldness. T-Flavanone might be helpful for people with various kind of baldness.

Abstract

The mechanism of hair growth promotion by t-flavanone. Sasajima, Michiyo. Biological Science Laboratories, Tochigi, Japan. Fragrance Journal (2005), 33(12), 36-43. Publisher: Fureguransu Janaru Sha, CODEN: FUJAD7 ISSN: 0288-9803. Journal; General Review written in Japanese. CAN 144:418982 AN 2006:47790 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


We investigated the expression of the five anthocyanin biosynthetic genes, chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGluT) during ripening in five early ripening apple cultivars ('Iwai', 'Sansa', 'Tsugaru', 'Homei-Tsugaru', and 'Akane'), as well as under UV-B and temp. treatments. Anthocyanin biosynthesis increased progressively during ripening, with the onset of rapid accumulation occurring at 107 days after full bloom (DAFB) in the four apple cultivars except Iwai'. Generally, increase in the expression levels of all five biosynthetic genes in fruit skin coincided with increase of anthocyanin concn. When the fruit was bagged about 1 mo prior to com. harvest to prevent anthocyanin biosynthesis, the expression of CHS, ANS and UFGluT was substantially depressed in fruit skin, whereas that of all five genes including CHS, ANS and UFGluT was enhanced by UV-B and low temp. treatments with the accumulation of anthocyanins. The accumulation level of the main anthocyanin pigment, cyanidin 3-galactoside, in the fruits under UV-B and low temp. treatment, was less than that in the field-ripened fruits, while cyanidin 3-arabinoside was relatively the same level. Our results showed that UV-B and low temp. were important factors for anthocyanin accumulation in apple fruit skin by inducing the expression of the anthocyanin biosynthetic genes, esp. CHS, ANS and UFGluT genes.

Abstract

Expression analysis of anthocyanin biosynthetic genes in apple skin: Effect of UV-B and temperature. Ubi, Benjamin Ewa; Honda, Chikako; Bessho, Hideo; Kondo, Satoru; Wada, Masato; Kobayashi, Shozo; Moriguchi, Takaya. Department of Plant, Cell and Environment, National Institute of Fruit Tree Science, Tsukuba, Ibaraki, Japan. Plant Science (Amsterdam, Netherlands) (2006), 170(3), 571-578. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 144:308381 AN 2006:58559 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Regiospecific Flavonoid 7-O-Methylation with Streptomyces avermitilis O-Methyltransferase Expressed in Escherichia coli. Kim, Bong-Gyu; Jung, Bo-Ra; Lee, Youngshim; Hur, Hor-Gil; Lim, Yoongho; Ahn, Joong-Hoon. Bio/Molecular Informatics Center, Department of Molecular Biotechnology, Konkuk University, Seoul, S. Korea. Journal of Agricultural and Food Chemistry (2006), 54(3), 823-828. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 144:272711 AN 2006:31106 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


5,7,3',4'-Tetrahydroxy-2'-(7''-hydroxy-3'',7''-dimethyloct-2''-enyl)flavanone (propolin A), 5,7,3',4'-tetrahydroxy-2'-geranylflavanone (nymphaeol B), 5,7,3',4'-tetrahydroxy-5'-geranylflavanone (isonymphaeol B), and 5,7,3',4'-tetrahydroxy-6-geranylflavanone (nymphaeol A) are manufd. by extn. of M. tanarius and purifn. of the obtained flavanones. Thus, pulverized M. tanarius leaves, stems, trunks, and seeds were extd. with EtOH and purified by photodiode array-HPLC to give propolin A, nymphaeol A, B, and isonymphaeol B at 48.7, 20.3, 62.9, and 5.2 μg/mg, resp.


Manufacture of flavanones from Macaranga tanarius. Kumasawa, Shigenori; Nakayama, Tsutomu; Arakaki, Tsutomu; Fukumoto, Shuichi. (Pokka Corp., Japan). Jpn. Kokai Tokkyo Koho (2006), 11 pp. CODEN: JKXXAF JP 2006008552 A 20060112 Patent written in Japanese. Application: JP 2004-185655 20040623. Priority: . CAN 144:94232 AN 2006:34945 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Studies on the chem. constituents of the flowers of Azadirachta indica have led to the isolation of one new flavanone named as azharone (5,7,4'-trihydroxy-3'-(3''-methyl-2'',3''-epoxybutyl)flavan-4-one) along with two known constituents azadirone, and isoazadironolide. Their structures have been elucidated through spectral studies including 2D-NMR (COSY-45, NOESY, J-resolved, HMQC, HMBC) expts.

Abstract

A new flavanoid from the flowers of Azadirachta indica. Siddiqui, Bina S.; Tariq Ali, Syed; Kashif Ali, Syed. H.E.J. Research Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi, Karachi, Pak. Natural Product Research, Part A: Structure and Synthesis (2006), 20(3), 241-245. Publisher: Taylor & Francis Ltd., CODEN: NPRPC8 Journal written in English. CAN 144:408198 AN 2006:46172 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Claisen condensation of substituted 2'-hydroxyacetophenones I (R = R2 = H, R1 = MeO; R = H, R1 = R2 = MeO; R = R1 = MeO, R2 = H) with arom. aldehydes II (R3, R4, R5, R6 = H, MeO; R3 = R6 = H, R4R5 = OCH2O) affords resp. substituted 2'-hydroxychalcones III which on base catalyzed cyclization in pyridine:methanol:water (1:1:1) give resp. flavanones IV. The oxidative rearrangement of flavanones IV with thallium(III) p-tosylate furnishes resp. isoflavones V in overall 62-72% yields starting from I. The present methodol. has been successfully applied for the synthesis of naturally occurring isoflavones such as di-O-methyldaidzein, cabruvin, pseudobabtigenin methylether, 5,7-dimethoxyisoflavone, 5,7,4'-trimethoxyisoflavone, derrustone, 7,8,3',4'-tetramethoxyisoflavone, purpuranin-A and 7,8,3',4',5'-pentamethoxyisoflavone (VI) and thus the first synthesis of VI is reported.

Abstract

Synthesis of isoflavones containing naturally occurring substitution pattern by oxidative rearrangement of respective flavanones using thallium(III) p-tosylate. Singh, Om V.; Muthukrishnan, M.; Sunderavadivelu, M. Phytochemistry Division, Tropical Botanic Garden and Research Institute, Thiruvanathapuram, India. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2005), 44B(12), 2575-2581. Publisher: National Institute of Science Communication and Information Resources, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 146:142391 AN 2006:1051 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Water extn., silica gel, Diaion HP-20, Toyopearl HW-40, Sephadex LH-20 column hromatog. were used. for studying the chem. constituents of Dryopteris sublaeta Ching et Hsu. The structures of isolated compds. were elucidated by various physiochem. and spectral data. Six compds. were obtained and identified as 2(S)-5,7,3'-trihydroxy-6,8-dclimethyl-4'-methoxy-flavanone (3'-hydroxy-matteucinol) (1), matteucinol-7-O-β-D-glucopyranoside (2), spinasterol (3), spinasterol-3-O-β-D-glucopyranoside (4), sitosterol (5) and daucosterol (6). Compd. 1 is new; compds. 2, 3 and 4 were isolated from Dryopteris for the first time.

Abstract

Isolation and structure identification of a new flavanone from Dryopteris sublaeta. Feng, Wei-Sheng; Cao, Xin-Wei; Kuang, Hai-Xue; Zheng, Xiao-Ke. Sch. Pharm., Henan Coll. Traditional Chinese Med., Zhengzhou, Peop. Rep. China. Zhongguo Tianran Yaowu (2005), 3(6), 336-339. Publisher: Zhongguo Tianran Yaowu Bianjibu, CODEN: ZTYHA7 ISSN: 1672-3651. Journal written in English. CAN 145:414091 AN 2006:18041 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O-Methylation, commonly found in synthesis of secondary metabolites of plants and micro-organisms, appears to transfer a Me group to the hydroxyl group of the recipient which increases the hydrophobicity of the recipient. O-Methyltransferase (OMT), SaOMT-2, was isolated and characterized from Streptomyces avermitilis MA-4680. Its amino acid sequence showed 68% similarity with antibiotic C-1027 OMT and 53% similarity with the carminomycin 4-OMT. SaOMT-2 was expressed in E. coli as a His-tag fusion protein and showed that the Me was transferred onto the 7- hydroxyl group of the isoflavones, daidzein and genistein, and the flavones, kaempferol and quercetin, as well as the flavanone naringenin. NMR and liq. chromatog.-mass spectrometry were used to confirm the location of the Me group on the recipient compd. of naringenin, which was biotransformed into sakuranetin by E. coli transformant expressing SaOMT-2 (E. coli Sa-2). Therefore, E. coli Sa-2 would be used for the synthesis of the antifungal flavonoid, sakuranetin, through biotransformation.

Abstract


flavanone

Flavonoids, a group of low mol. wt. phenylbenzopyrones, have various pharmacol. properties including antioxidant, anticancer, bactericidal, and anti-inflammatory. We carried out anti-herpetic assays on 18 flavonoids in five classes and a virus-induced cytopathic effect (CPE) inhibitory assay, plaque redn. assay, and yield redn. assay were performed. When flavonoids were applied at various concns. to Vero cells infected by HSV-1 and 2, most of the flavonoids showed inhibitory effects on virus-induced CPE.

Abstract

Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro. Lyu, Su-Yun; Rhim, Jee-Young; Park, Won-Bong. Immune Modulation Research Group, The School of Pharmacy, University of Nottingham, Nottingham, UK. Archives of Pharmacal Research (2005), 28(11), 1293-1301. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 144:403824 AN 2005:1355075 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OH

R

Me

O

R

O

R

OHR

R

R

H

O

O

R

OR

R

O

R

OR

1

R2

1

R2

3

R4

R5

R6

3

R4

R5

R6

1

R2

3

R4

R5

R6

1

R2

R3

R4

R5

R6

I

V

IV

II

III


flavanone

Flavanone derivs. (I) [X = each (un)substituted Ph or heteroaryl; Y = (un)substituted Ph, pyridyl; R1 -R3 = H, halo, C1-12 alkoxy, HO, each (un)substituted C2-6 cyclic or noncyclic amino, Ph, PhO, benzyloxy,, or heteroaryl; X is in E or Z form or in its mixt.] are prepd. These compds. are useful for the treatment of acute lung injury (ALI) and acute respiratory distress syndrome (ARDS), chronic obstructive pulmonary disease (COPD), and asthma and for protection of transplanted organs. Thus, 224 mg flavanone, 174 mg


Preparation of flavanone derivatives as inducers of heme oxygenase or induction promoters of heme oxygenase. Miyaji, Hiroyuki; Eiraku, Tomohiko; Ishiguro, Hanae. (Kyorin Pharmaceutical Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2005), 42 pp. CODEN: JKXXAF JP 2005350362 A 20051222 Patent written in Japanese. Application: JP 2004-170090 20040608. Priority: . CAN 144:69734 AN 2005:1334474 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. constituents from the rhizomes of Smilax glabra were studied. The compds. were isolated by column chromatog. with silica gel, Diaion HP-20 and ODS as packing materials, and HPLC. Their structures were detd. on the basis of their spectral evidence. Five dihydroflavonol glycosides were identified as: astilbin (1), neoastilbin (2), isoastilbin (3), neoisoastilbin (4), and (2R,3R)-taxifolin-3'-O-β-D-glucopyranoside (5). Compds. 2, 4, 5 were isolated from the plant for the first time.

Abstract

Studies on dihydroflavonol glycosides from rhizome of Smilax glabra. Yuan, Jiuzhi; Dou, Deqiang; Chen, Yingjie; Li, Wei; Kazuo, Koike; Tamotsu, Nikaido; Yao, Xinsheng. Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang, Peop. Rep. China. Zhongguo Zhongyao Zazhi (2004), 29(9), 867-869, 870. Publisher: Zhongguo Zhongyao Zazhishe, CODEN: ZZZAE3 ISSN: 1001-5302. Journal written in Chinese. CAN 145:24149 AN 2005:1346876 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Among the flavonoids, EC, ECG (flavanols), genistein (isoflavone), naringenin (flavanone), and quercetin (flavonol) showed a high level of CPE inhibitory activity. The antiviral activity of flavonoids were also examd. by a plaque redn. assay. EC, ECG, galangin, and kaempferol showed a strong antiviral activity, and catechin, EGC, EGCG, naringenin, chrysin, baicalin, fisetin, myricetin, quercetin, and genistein showed moderate inhibitory effects against HSV-1. In these expts., flavanols and flavonols appeared to be more active than flavones. Furthermore, treatment of Vero cells with ECG and galangin (which previously showed strong antiviral activities) before virus adsorption led to a slight enhancement of inhibition as detd. by a yield redn. assay, indicating that an intracellular effect may also be involved.


flavanone

Abstract

Synthesis and application of mono-2A-azido-2A-deoxyperphenylcarbamoylated β-cyclodextrin and mono-2A-azido-2A-deoxyperacetylated β-cyclodextrin as chiral stationary phases for high-performance liquid chromatography. Poon, Yin-Fun; Muderawan, I. Wayan; Ng, Siu-Choon. Innovation Centre, Division of Chemical and Biomolecular Engineering, College of Engineering, Nanyang Technological University, Singapore, Singapore. Journal of Chromatography, A (2006), 1101(1-2), 185-197. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 144:219477 AN 2005:1319721 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavones are plant secondary metabolites that have wide pharmaceutical and nutraceutical applications. We previously constructed a recombinant flavanone pathway by expressing in Saccharomyces cerevisiae a four-step recombinant pathway that consists of cinnamate-4 hydroxylase, 4-coumaroyl:CoA ligase, chalcone synthase, and chalcone isomerase. In the present work, the biosynthesis of flavones by two distinct flavone synthases was evaluated by introducing a sol. flavone synthase I (FSI) and a membrane-bound flavone synthase II (FSII) into the flavanone-producing recombinant yeast strain. The resulting recombinant strains were able to convert various phenylpropanoid acid precursors into the flavone mols. chrysin, apigenin, and luteolin, and the intermediate flavanones pinocembrin, naringenin, and eriodictyol accumulated in the medium. Improvement of flavone biosynthesis was achieved by overexpressing the yeast P 450 reductase CPR1 in the FSII-expressing recombinant strain and by using acetate rather than glucose or raffinose as the carbon source. Overall, the FSI-expressing recombinant strain produced 50% more apigenin and six times less naringenin than the FSII-expressing recombinant strain when p-coumaric acid was used as a precursor phenylpropanoid acid. Further expts. indicated that unlike luteolin, the 5,7,4'-trihydroxyflavone apigenin inhibits flavanone biosynthesis in vivo in a nonlinear, dose-dependent manner.

Abstract

Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae. Leonard, Effendi; Yan, Yajun; Lim, Kok Hong; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2005), 71(12), 8241-8248. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 144:190663 AN 2005:1332708 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

Y

X

R3

1

2

R

R

I

4-trifluoromethylbenzaldehyde, and 0.03 mL piperidine were mixed and stirred at 150° for 2 h to give, after silica gel chromatog., 3-(4-trimethoxybenzylidene)flavanone. 3-(3,4,5-Trimethoxybenzylidene)flavanone at 3 μM increased heme oxygenase activity by 10.13 fold in human umbilical vein endothelial cells (HUVECs) based on the increased prodn. of bilirubin.


flavanone

Abstract

Characterization of Flavonoids and Pectins from Bergamot (Citrus bergamia Risso) Peel, a Major Byproduct of Essential Oil Extraction. Mandalari, Giuseppina; Bennett, Richard N.; Bisignano, Giuseppe; Saija, Antonella; Dugo, Giacomo; Lo Curto, Rosario B.; Faulds, Craig B.; Waldron, Keith W. Department of Pharmaco-Biology and Department of Organic and Biological Chemistry, University of Messina, Messina, Italy. Journal of Agricultural and Food Chemistry (2006), 54(1), 197-203. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 144:190814 AN 2005:1302713 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Antibacterial activities of various flavonoids were reported previously, but mechanism(s) of their action on bacterial cells remain(s) largely unknown. Here, the authors investigated effects of genistein, an isoflavone, and representatives of other flavonoids: daidzein (another isoflavone), apigenin (a flavone), naringenin (a flavanone), and kaempferol (a flavonol), on commonly used lab. strains of model bacterial species: Escherichia coli, Vibrio harveyi, and Bacillus subtilis. The authors found that E. coli was resistant to all tested flavonoids at concns. up to 0.1 mM, while high sensitivity of V. harveyi to most of them (except daidzein, which exhibited significantly less pronounced effect) was obsd. Effects of the flavonoids on B. subtilis were relatively intermediate to the 2 extremes, i.e., E. coli and V. harveyi. Action of genistein on bacterial cells was investigated in more detail to indicate changed cell morphol. (formation of filamentous cells) of V. harveyi and drastic inhibition of global synthesis of DNA and RNA as shortly as 15 min after addn. of this isoflavone to a bacterial culture to a final concn. of 0.1 mM. Protein synthesis inhibition was also apparent, but delayed. Both cell morphol. and synthesis of nucleic acids and proteins were unaffected in E. coli cultures under analogous conditions. Studies on cell survival suggest that genistein is a bacteriostatic agent rather than a bactericidal compd.

Abstract

Differential antibacterial activity of genistein arising from global inhibition of DNA, RNA and protein synthesis in some bacterial strains. Ulanowska, Katarzyna; Tkaczyk, Aleksandra; Konopa, Grazyna; Wegrzyn, Grzegorz. Department of Molecular Biology, University of Gdansk, Gdansk, Pol. Archives of Microbiology (2006), 184(5), 271-278. Publisher: Springer, CODEN: AMICCW ISSN: 0302-8933. Journal written in English. CAN 144:250223 AN 2005:1317507 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two novel chiral stationary phases (CSPs) were prepd. based upon the regioselective immobilizations of β-cyclodextrin (β-CD) at its C2 position to the silica support. The mono-2A-azido-2A-deoxyperphenylcarbamoylated β-cyclodextrin and mono-2A-azido-2A-deoxyperacetylated β-cyclodextrin were synthesized by selective tosylation and azidolysis followed by perfunctionalization. The derivatized cyclodextrins were then immobilized onto the aminised silica gel via the Staudinger reaction to provide new chiral stationary phases. Their application to high-performance liq. chromatog. (HPLC) enantiosepn. of racemic compds. was demonstrated using β-adrenergic blockers, flavanone compds., benzodiazepinones, antihistamines and weakly protolytic compds., of which good sepns. were achieved for some racemic compds., for instance, bendroflumethiazide (R s 6.26), oxazepam (R s 5.99), temazepam (R s 2.85) and althiazide (R s 1.13) when compared with the corresponding CSPs where the β-CD mol. was regioselectively immobilized at the C6 position. The enantio-discriminatory properties of these CSPs were found to be affected by the orientation of the CD cavity under reversed-phase conditions, and also by the derivitizing groups of the CD. The HPLC results inferred that the mono-6A-azido-6A-deoxyperphenylcarbamoylated CD CSP (CD bonded at C6 position to silica) exhibited slightly better chiral recognition ability than mono-2A-azido-2A-deoxyperphenylcarbamoylated CD CSP under the normal-phase and reversed-phase modes on the sepn. of 31 different racemic compds. and drugs. On the contrary, higher chiral recognition abilities were obsd. on the mono-2A-azido-2A-deoxyperacetylated CD CSP compared to mono-6A-azido-6A-deoxyperacetylated CD CSP.


flavanone

Citrus flavonoids have been shown to possess biol. activities such as anti-inflammatory properties, cholesterol lowering and immune system modulation. In this study, 12 made-from-conc. (MFC) and 14 not-from-conc. (NFC) orange juices, and five NFC grapefruit juices available in the US market were analyzed for their flavonoid content by reverse phase HPLC. Individual and total flavonoid content was detd. for all of the brands. The correlation between flavonoid content (mg) and price (US dollar) per unit vol. of orange and grapefruit juices were also evaluated. Significant differences ( P ≤ 0.05 ) among the brands and within the brand were obsd. for all of the prominent flavanone glucosides. Within the brand, juice types contg. added antioxidant vitamins C and E were not superior in flavonoid content compared to orange juice types devoid of added antioxidant vitamins. Total flavonoid content of MFC orange juices (53 mg/100 mL; n = 12 ) was significantly ( P ≤ 0.05 ) higher than NFC orange juices (36.5 mg/100 mL; n = 14 ). Hesperidin was found to be the major flavonoid followed by narirutin and didymin in orange juice. Naringin, narirutin, and poncirin were the major flavonoids in all brands of grapefruit juices. The concn. of didymin was considerably higher in NFC orange juices compared to MFC orange juices. Interestingly, no correlation was obsd. between price and the total flavonoid content of MFC orange juices and NFC grapefruit juices. However, a significant neg. correlation ( r = - 0.49 ; P = 0.001 ) was obsd. for NFC orange juices. This study provides valuable information on flavonoid compn. of orange and grapefruit juices commonly available in the US market.

Abstract

Variation in the content of bioactive flavonoids in different brands of orange and grapefruit juices. Vanamala, Jairam; Reddivari, Lavanya; Yoo, Kil Sun; Pike, Leonard M.; Patil, Bhimanagouda S. Department of Horticultural Sciences, Vegetable and Fruit Improvement Center, College Station, TX, USA. Journal of Food Composition and Analysis (2005), Volume Date 2006, 19(2-3), 157-166. Publisher: Elsevier, CODEN: JFCAEE ISSN: 0889-1575. Journal written in English. CAN 145:270471 AN 2005:1297934 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


As a new method, support vector machine (SVM) were applied for prediction of toxicity of different data sets compared with other two common methods, multiple linear regression (MLR) and RBFNN. Quant. structure-activity relationships (QSAR) models based on calcd. mol. descriptors have been clearly established. Among them, SVM model gave the highest q 2 and correlation coeff. R. It indicates that the SVM performed better generalization ability than the MLR and RBFNN methods, esp. in the test set and the whole data set. This eventually leads to better generalization than neural networks, which implement the empirical risk minimization principle and may not converge to global solns. We would expect SVM method as a powerful tool for the prediction of mol. properties.

Abstract

Application of support vector machine (SVM) for prediction toxic activity of different data sets. Zhao, C. Y.; Zhang, H. X.; Zhang, X. Y.; Liu, M. C.; Hu, Z. D.; Fan, B. T. Department of Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China. Toxicology (2006), 217(2-3), 105-119. Publisher: Elsevier Ltd., CODEN: TXCYAC ISSN: 0300-483X. Journal written in English. CAN 144:268702 AN 2005:1300036 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Bergamot peel is an underutilized byproduct of the essential oil and juice-processing industry. As with other Citrus peels, it still contains exploitable components, such as pectins and flavonoids. Com. glycoside hydrolases, specifically a combination of pectolytic and cellulolytic enzymes, solubilized a high percentage of the material (81.94%). The flavonoid profile of the peel consisted of characteristic Citrus species flavanone rutinosides and neohesperosides derived from naringenin, eriodictyol, and hesperetin. In addn., a no. of minor flavanone and flavone glycosides, not found in orange and lemon peels, were identified. The majority of flavonoids were extd. in the 2 70% vol./vol. EtOH extns. Processing this material clearly has economic potential leading to low environmental impact.


flavanone


RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW

WO 2006118553 A1 20061109 WO 2005-US5492 20050222US 20050266105 A1 20051201 US 2005-62769 20050222Patent No. Kind Date Application No. Date Patent Family Information

Compositions comprising extracts from Zanthoxylum and Anogeissus and citrus juice for the treatment of HIV-associated infections and complications. Ashiagbor, Kwame Titus; Ashiagbor, Stephen; Wutoh, Anthony K.; Kallia, Yaw Foster; Wutoh, Rita Delores; Wutoh, Jeffrey K.; Aidoo, Elnora. (Ghana). U.S. Pat. Appl. Publ. (2005), 16 pp. CODEN: USXXCO US 2005266105 A1 20051201 Patent written in English. Application: US 2005-62769 20050222. Priority: US 2004-545508 20040219. CAN 144:11623 AN 2005:1262745 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new dihydrochalcones, 2',4'-dihydroxy-3'-methoxydihydrochalcone, (-)-3'-methoxy-2',4',β-trihydroxydihydrochalcone, a new flavanone, (2S)-(-)-5'-hydroxy-7,3',4'-trimethoxyflavanone, and a new flavonol deriv., muntingone, along with sixteen known compds., were isolated from the leaves of Muntingia calabura. The structures of these new compds. were detd. using spectral analyses including extensive 2D NMR data. Among the isolates, (2S)-5'-hydroxy-7,3',4'-trimethoxyflavanone, 4'-hydroxy-7-methoxyflavanone, 2',4'-dihydroxychalcone, and 2',4'-dihydroxy-3'-methoxychalcone exhibited cytotoxicity (IC50 values < 4 μg/mL) against P-388 and/or HT-29 cell lines in vitro.

Abstract

Cytotoxic chalcones and flavonoids from the leaves of Muntingia calabura. Chen, Jih-Jung; Lee, Hsinn-Hsing; Duh, Chang-Yih; Chen, Ih-Sheng. Graduate Institute of Pharmaceutical Technology, Tajen Institute of Technology, Pingtung, Taiwan. Planta Medica (2005), 71(10), 970-973. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 144:383543 AN 2005:1263704 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Naringin, the main flavanone of grapefruit, was reported to display numerous biol. effects: antioxidant, hypocholesteremic, anti-atherogenic and favoring drug absorption. Naringin absorption mechanisms were studied in Caco-2 cells (TC7 clone). We investigated the possible involvement of several membrane transporters implicated in polyphenolic compds. intestinal transport (sodium-dependent glucose transporter 1, monocarboxylate transporter, multidrug-assocd. resistance proteins 1 and 2, and P-glycoprotein). Naringin was poorly absorbed by Caco-2 cells, according to its low value of apparent permeability coeff. (Papp = 8.1

Abstract

Molecular mechanism of the naringin low uptake by intestinal Caco-2 cell. Tourniaire, Franck; Hassan, Meryl; Andre, Marc; Ghiringhelli, Odette; Alquier, Christian; Amiot, Marie-Josephe. Faculte de Medecine, UMR U-476 INSERM/U-1260 INRA, Marseille, Fr. Molecular Nutrition & Food Research (2005), 49(10), 957-962. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: MNFRCV ISSN: 1613-4125. Journal written in English. CAN 145:7045 AN 2005:1252115 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Me

Me

Me

MeH

OH

O I

The chem. constituents of the leaves and stems of Schisandra plena are described for the first time. This investigation has resulted in the isolation of a new sesquiterpenoid, plenoxide (I). In addn., eleven known compds., including sesquiterpenoids, coumarins, flavanones, triterpenoids and steroids have also been isolated. The structure and stereochem. of 1 has been detd. on the basis of spectroscopic anal. Detailed anal. of 2D NMR data led to the conclusion that the chem. shifts of earlier compds. similar to bullatantriol need revision.

Abstract

Chemical constituents from Schisandra plena. Li, R.-T.; Zhao, A.-H.; Sheng, Y.-H.; Na, Z.; Sun, H.-D. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peop. Rep. China. Journal of Asian Natural Products Research (2005), 7(6), 847-852. Publisher: Taylor & Francis Ltd., CODEN: JANRFI ISSN: 1028-6020. Journal written in English. CAN 145:414060 AN 2005:1256605 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention pertains to compns. for the treatment of HIV-related opportunistic infections and complications. More specifically, the present invention is directed to a compn. comprising Zanthoxylum gillettii and Anogeissus leiocarpus, in combination with citrus juice, or biomass exts. isolated therefrom, and methods of using and manufg. the same. For example, an i.p. compns. contg. exts. from Zanthoxylum and Anogeissus and citrus juice was found to be able to effectively treat HIV assocd. infections.


flavanone

Answer 529:

We examd. the inhibitory activities of various flavonoids, including the flavanones, flavones/isoflavones and flavonols, on collagenase from Clostridium histolyticum to establish their therapeutic potential against skin inflammation and photoaging. In general, the flavonols were stronger inhibitors than the flavones/isoflavones, and this indicated the importance of the C-3 hydroxyl substitution. Quercetin was the most active flavonoid among those tested, and it showed an IC50 of 286 μM. These novel results suggest that certain flavonoids, particularly the flavonols, may prevent collagen breakdown by inhibiting collagenase in inflamed skin as well as photoaged skin.

Abstract

Inhibition of collagenase by naturally-occurring flavonoids. Sin, Bo Young; Kim, Hyun Pyo. College of Pharmacy, Kangwon National University, Chunchon, S. Korea. Archives of Pharmacal Research (2005), 28(10), 1152-1155. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 143:452796 AN 2005:1218838 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The ability of a no. of flavonoids belonging to the flavone, flavonol, flavanone, and flavan-3-ol subclasses to protect cellular DNA from H2O2-induced single-strand breaks and the underlying mol. mechanisms were investigated in this work. Formation of single-strand breaks on nuclear DNA, after exposure of Jurkat cells to continuously generated H2O2 in the presence or absence of the flavonoid compds., was evaluated by the comet assay (single-cell gel electrophoresis). The results indicate the following structural requirements of flavonoids for effective DNA protection: (a) the ortho-dihydroxy structure in either ring A or ring B, (b) the hydroxyl moiety on position 3 in combination with the oxo group at position 4, and (c) the presence of a C2, C3 double bond in ring C. In contrast to free flavonoids, the ability of complexes of [Fe2+]/[flavonoid] to protect nuclear DNA was decreased as the ratio increased, and the complex was completely inactive when the ratio reached a certain value. Moreover, it was obsd. that several of the flavonoids tested were able to remove iron from calcein loaded into cells and that this property was in excellent correlation with their ability to protect DNA (Spearman's correlation coeff., ρ = 0.9, p = 0.005). The antioxidant (electron donating) capacities of the same flavonoids were also evaluated by a conventional method, but no relation with their DNA-protective ability could be established even when their membrane-penetrating abilities were taken into account (p = 0.64). In conclusion, the results presented in this work strongly support the notion that intracellular binding of iron is responsible for the protection offered by flavonoids against H2O2-induced DNA damage.

Abstract

Protection against nuclear DNA damage offered by flavonoids in cells exposed to hydrogen peroxide: The role of iron chelation. Melidou, Maria; Riganakos, Kyriakos; Galaris, Dimitrios. Laboratory of Biological Chemistry, School of Medicine, University of Ioannina, Ioannina, Greece. Free Radical Biology & Medicine (2005), 39(12), 1591-1600. Publisher: Elsevier, CODEN: FRBMEH ISSN: 0891-5849. Journal written in English. CAN 144:45018 AN 2005:1233685 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


± 0.9 × 10-8 cm/s). In the presence of verapamil, a specific inhibitor of P-glycoprotein, cellular uptake was increased by almost threefold after 5 min, and Papp was doubled after 30 min. Our results indicated the involvement of P-glycoprotein, an ATP-driven efflux pump, capable of transporting naringin from the Caco-2 cell to the apical side. This phenomenon could explain, at least in part, the low absorption of this flavanone at the upper intestinal level.


flavanone

Capillary electrochromatography on methacrylate based monolithic columns: Evaluation of column performance and separation of polyphenols. Messina, A.; Desiderio, C.; De Rossi, A.; Bachechi, F.; Sinibaldi, M. Dipartimento di Chimica, Universita di Roma "La Sapienza", Rome, Italy. Chromatographia (2005), 62(7/8), 409-416. Publisher: Vieweg Verlag/GWV Fachverlage GmbH, CODEN: CHRGB7 ISSN: 0009-5893. Journal written in English. CAN 144:169758 AN 2005:1204471 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new natural flavanones, 5-hydroxy-6,7-(2'',2''-dimethylchromene)flavanone and 5-methoxy-3-hydroxy-6,7-(2'',2''-dimethylchromene)flavanone, were isolated from the root exts. of L. yucatanensis and L. xuul, resp. Addnl., 4 known metabolites, the glycosidic flavonoids quercetin-3-rhamnoglucoside and kaempferol-3-rhamnoglucoside, together with 4-hydroxy-N-methyl-proline, and p-coumaric acid Me ester, were isolated for the first time from the leaves of L. xuul. The various metabolites were identified on the basis of their spectroscopic data and by comparison with those reported in the literature.

Abstract

Additional flavonoids from Lonchocarpus yucatanensis and L. xuul. Borges-Argaez, Rocio; Diaz, Maria Esther Poot; Waterman, Peter G.; Pena-Rodriguez, Luis M. Unidad de Biotecnologia, Centro de Investigacion Cientifica de Yucatan, Merida, Mex. Journal of the Brazilian Chemical Society (2005), 16(5), 1078-1081. Publisher: Sociedade Brasileira de Quimica, CODEN: JOCSET ISSN: 0103-5053. Journal written in English. CAN 144:408136 AN 2005:1206260 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Neohesperidin dihydrochalcone (NHDC) is a seminatural, safe, low-calorie sweetener, bitterness blocker, and flavor enhancer with unique properties and applications for the food, beverage, pharmaceutical, and animal feed industries. Current prodn. is limited by the availability of the substrate neohesperidin, a flavonoid that accumulates to significant levels only in the inedible bitter citrus species. We propose a process to convert hesperidin, a tasteless flavonoid extd. from orange peels that are abundant byproducts of the vast orange juice industry, into neohesperidin using metabolic engineering and biotransformation via three steps: (i) extn. of hesperidin from orange peels, (ii) hydrolysis of sugar moieties, and (iii) biotransformation of hesperidin hydrolysis products into neohesperidin. We overcame the current technol. bottleneck in biotransformation of hesperidin hydrolysis products into neohesperidin using metabolically engineered plant cell cultures expressing a recombinant flavanone-7-O-glucoside-2-O-rhamnosyltransferase. A small-scale prodn. expt. established the feasibility of the proposed process.

Abstract

Metabolic engineering of plant cells for biotransformation of hesperedin into neohesperidin, a substrate for production of the low-calorie sweetener and flavor enhancer NHDC. Frydman, Ahuva; Weisshaus, Oori; Huhman, David V.; Sumner, Lloyd W.; Bar-Peled, Maor; Lewinsohn, Efraim; Fluhr, Robert; Gressel, Jonathan; Eyal, Yoram. Institute of Horticulture, Volcani Center, Bet-Dagan, Israel. Journal of Agricultural and Food Chemistry (2005), 53(25), 9708-9712. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 144:107017 AN 2005:1211342 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


A cDNA encoding chalcone isomerase (CHI) was isolated from the petals of Nicotiana tabacum and the effect of its suppression on flavonoid biosynthesis was analyzed in transgenic tobacco plants. CHI-suppression by RNA interference (RNAi) showed reduced pigmentation and change of flavonoid components in flower petals. The plants also accumulated high levels of chalcone in pollen, showing a yellow coloration. Our results first demonstrated that suppression of CHI by genetic transformation is possible in higher plants. This suggests that CHI plays a major part in the cyclization reaction from chalcone to flavanone, and that spontaneous reactions are few, if any, in tobacco plants.

Abstract

Flavonoid components and flower color change in transgenic tobacco plants by suppression of chalcone isomerase gene. Nishihara, Masahiro; Nakatsuka, Takashi; Yamamura, Saburo. Iwate Biotechnology Research Center, Narita, Kitakami, Iwate, Japan. FEBS Letters (2005), 579(27), 6074-6078. Publisher: Elsevier B.V., CODEN: FEBLAL ISSN: 0014-5793. Journal written in English. CAN 144:84159 AN 2005:1187425 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Oxidn. of flavanones with manganese(III) acetate by heating in acetic acid in presence of perchloric acid afforded exclusively flavones by dehydrogenation in almost quant. yields.

Abstract

Manganese(III) acetate-mediated oxidation of flavanones. A facile synthesis of flavones. Singh, Om V.; Muthukrishnan, M.; Raj, Gopan. Phytochemistry Division, Tropical Botanic Garden and Research Institute, Thiruvananthapuram, India. Synthetic Communications (2005), 35(20), 2723-2728. Publisher: Taylor & Francis, Inc., CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 144:69639 AN 2005:1191892 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Fused-silica capillary columns (100 μm I.D.) englobing a porous monolithic stationary phase were prepd. by in situ copolymn. of 2-ethylhexyl methacrylate, ethylene glycol dimethacrylate and 2-acrylamido-2-methylpropanesulfonic acid (AMPS) in the presence of a porogenic mixt. contg. 1-propanol, 1,4 butanediol and water. The influence of the monomers ratio and the porogen solvent compn. as well as the content of AMPS in the polymn. mixt. on column total porosity and efficiency was investigated to attain min. HETP values for the reversed-phase capillary electrochromatog. sepn. of bioflavonoids. For the most promising column, the van Deemter plots, in both μ-HPLC and CEC, were also evaluated. In CEC the reduced plate height was found almost const. (1.6-2.0) within the range of linear mobile phase velocity between 0.2-2.0 mm/s. The chem. and mech. stabilities of the monolithic column over a wide range of buffer pH (2-10) and time were satisfactory. Furthermore, the effects of mobile phase parameters, such as buffer concn. and org. modifier content, on the electroosmotic flow were studied systematically. CEC sepns. of std. mixts. of polyphenols, including flavonols, flavanones and flavanones-7-O-glycosides, were accomplished in less than 8 min. The CEC sepn. of the major flavanone glycoside constituents in the ext. from a freshly squeezed grapefruit juice was also reported.

Abstract


flavanone

Answer 537:

Hydroxy-substituted flavanones reacted with NO to afford mono- and multi-nitro derivs. The mononitration occurred at the ortho- or para-position with respect to the hydroxy group. Dinitrations occurred at two ortho-positions or both ortho- and para-positions to the hydroxy group with longer reaction time than that of mononitration. The reaction of polyhydroxy-substituted flavanones with NO gave polynitrated derivs.

Abstract

Reactions of hydroxy-substituted flavanones with nitric oxide. Zhang, Hong-Rui; Wu, Long-Min. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China. Youji Huaxue (2005), 25(10), 1248-1253. Publisher: Youji Huaxue Bianjibu, CODEN: YCHHDX ISSN: 0253-2786. Journal written in Chinese. CAN 145:292740 AN 2005:1151060 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The pharmacodynamics of flavanone exts. for treatment of vulva leukoplakia and its mechanism was studied. The flavanone ext. was made up into 0.2% tincture (contained 25% ethanol). The pharmacodynamics and the preliminary clin. effects of flavanone ext. tincture were explored by inhibition of virus in vitro; anti-inflammation, relieving itch, and alleviating pain in mice; anti-granuloma expt. in rats; and treatment of 116 patients with vulva leukoplakia. The drug had obvious effects to relieve pain and itch, accelerated the healing of the damaged tissues, anti-chronic granuloma and the acute inflammatory seeps and anti-virus. The prepn. of flavanone is substantiated that it is quick to take effect, easy to operate, less of toxic and side effect after treatment of patients with vulva leukoplakia.

Abstract

Studies of the pharmacodynamics of flavanone extract tinctures for treating vulva leukoplakia. Li, Shou-Xiang; Zhang, Xue-Jun; Meng, Hong; Han, Ru; Wu, Hong-Ying; Zheng, Yun-Xia; Ma, Jin-Feng; Zhu, Hua. Shandong Institute of Prevention and Control of Professional Health and Occupational Diseases, Ji'nan, Peop. Rep. China. Yaoxue Fuwu Yu Yanjiu (2005), 5(3), 296-299. Publisher: Yaoxue Fuwu Yu Yanjiu Zazhishe, CODEN: YFYYAH ISSN: 1671-2838. Journal written in Chinese. CAN 144:81115 AN 2005:1167495 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Crystals of the title compd. are monoclinic, space group P21/c, with a 10.1961(10), b 7.5600(8), c 18.243(2) .ANG., β 105.59(2)°; Z = 4, dc = 1.404, dm = 1.40; R = 0.064, Rw(F2) = 0.201 for 2346 reflections. The γ-pyranone ring adopts an envelope conformation. The crystal packing is stabilized by O-H⋅⋅⋅O and C-H⋅⋅⋅O H bonding.

Abstract

5,2'-Dihydroxy-7-methoxyflavanone. Krishnaiah, M.; Ravi Kumar, R.; Kumar, N. Jagadeesh; Gunasekar, D.; Jayaprakasam, B. Department of Physics, Sri Venkateswara University, Tirupati (AP), India. Acta Crystallographica, Section E: Structure Reports Online (2005), E61(11), o3565-o3567. Publisher: Blackwell Publishing Ltd., CODEN: ACSEBH ISSN: 1600-5368. http://journals.iucr.org/e/issues/2005/11/00/ci6641/index.html Journal; Online Computer File written in English. CAN 144:321849 AN 2005:1169850 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Colour genes (R and Rc) for grain and coleoptile upregulate flavonoid biosynthesis genes in wheat. Himi, Eiko; Nisar, Ahmed; Noda, Kazuhiko. Research Institute for Bioresources, Okayama University, Kurashiki, Okayama, Japan. Genome (2005), 48(4), 747-754. Publisher: National Research Council of Canada, CODEN: GENOE3 ISSN: 0831-2796. Journal written in English. CAN 144:408243 AN 2005:1133622 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new compd., reflexin, 5-hydroxy-7-methoxy-6-(2,3-epoxy-3-methylbutyl)-flavanone, is isolated from the stems of Cuscuta reflexa along with three other known compds. This new compd. has good potential for application esp. in the photoactivity of reflexin. It was found to be sensitive to glutathione, forming a fluorescent product that is utilized for sensing nitric oxide (NO). The lowest detection limit of NO anal. was found to be 0.05 μM.

Abstract

A new flavanone, reflexin, from Cuscuta reflexa and its selective sensing of nitric oxide. Tripathi, V. J.; Yadav, S. B.; Upadhyay, A. K. Department of Chemistry, Banaras Hindu University, Varanasi, India. Applied Biochemistry and Biotechnology (2005), 127(1), 63-67. Publisher: Humana Press Inc., CODEN: ABIBDL ISSN: 0273-2289. Journal written in English. CAN 144:66162 AN 2005:1133807 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


We used soybean (Glycine max) cDNA microarrays to identify candidate genes for a stable mutation at the Wp locus in soybean, which changed a purple-flowered phenotype to pink, and found that flavanone 3-hydroxylase cDNAs were overexpressed in purple flower buds relative to the pink. Restriction fragment length polymorphism anal. and RNA gel blots of purple and pink flower isolines, as well as the presence of a 5.7-kb transposon insertion in the wp mutant allele, have unequivocally shown that flavanone 3-hydroxylase gene 1 is the Wp locus. Moreover, the 5.7-kb insertion in wp represents a novel transposable element (termed Tgm-Express1) with inverted repeats closely related to those of other Tgms (transposable-like elements, G. max) but distinct in several characteristics, including the lack of subterminal inverted repeats. More significantly, Tgm-Express1 contains four truncated cellular genes from the soybean genome, resembling the Pack-MULEs (Mutator-like transposable elements) found in maize (Zea mays), rice (Oryza sativa), and Arabidopsis thaliana and the Helitrons of maize. The presence of the Tgm-Express1 element causing the wp mutation, as well as a second Tgm-Express2 element elsewhere in the soybean genome, extends the ability to acquire and transport host DNA segments to the CACTA family of elements, which includes both Tgm and the prototypical maize Spm/En.

Abstract

The wp mutation of Glycine max carries a gene-fragment-rich transposon of the CACTA superfamily. Zabala, Gracia; Vodkin, Lila O. Department of Crop Sciences, University of Illinois, Urbana, IL, USA. Plant Cell (2005), 17(10), 2619-2632. Publisher: American Society of Plant Biologists, CODEN: PLCEEW ISSN: 1040-4651. Journal written in English. CAN 144:287221 AN 2005:1134019 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Synthesis and Characterization of Cellulose Carbamates Having α-Amino Acid Moieties. Shen, Xiande; Sugie, Norihiko; Duan, Qian; Kitajyo, Yoshikazu; Satoh, Toshifumi; Kakuchi, Toyoji. Division of Biotechnology and Macromolecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Japan. Polymer Bulletin (Heidelberg, Germany) (2005), 55(5), 317-322. Publisher: Springer, CODEN: POBUDR ISSN: 0170-0839. Journal written in English. CAN 144:53224 AN 2005:1127171 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Skin-lightening cosmetics comprise (1) acidic xylooligosaccharides (av. polymn. degree ≤ 5), (2) keratinocyte prodn. signal transduction inhibitors, such as reduced NAD, and (3) ≥ 1 substances from the group consisting of melanin prodn. inhibitors, antioxidants, inflammation inhibitors, high-mol. wt. compds., and polyhydric alcs. For example, a cream was formulated contg. beeswax 2, stearyl alc. 5, stearic acid 8, squalane 10, glyceryl monostearate 3, polyoxyethylene cetyl ether 1, Helianthus annus seed exts. 5, acidic xylooligosaccharides 5, KOH 0.3, preservatives q.s., reduced NAD 0.1, and distd. water balance to 100 %.


Skin-lightening cosmetics containing acidic xylooligosaccharides, natural products, and polyhydric alcohols. Tanaka, Hiroshi; Azumi, Naoya. (Narisu Cosmetic Co., Ltd., Japan; Oji Paper Co., Ltd.). Jpn. Kokai Tokkyo Koho (2005), 16 pp. CODEN: JKXXAF JP 2005289880 A 20051020 Patent written in Japanese. Application: JP 2004-107255 20040331. Priority: . CAN 143:392550 AN 2005:1129090 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Pigmentation of wheat grain and coleoptile is controlled by the R gene on chromosomes of the homoeologous group 3 and the Rc gene on chromosomes of the homoeologous group 7, resp. Each of these genes is inherited monogenically. The pigment of grain has been suggested to be a deriv. of catechin-tannin and that of coleoptile to be anthocyanin. These polyphenol compds. are known to be synthesized through the flavonoid biosynthesis pathway. We isolated 4 partial nucleotide sequences of the early flavonoid biosynthesis genes (CHS, CHI, F3H, and DFR) in wheat. The expression of these genes was examd. in the developing grain of red-grained and white-grained wheat lines. CHS, CHI, F3H, and DFR were highly upregulated in the grain coat tissue of the red-grained lines, whereas there was no significant expression in the white-grained lines. These results indicate that the R gene is involved in the activation of the early flavonoid biosynthesis genes. As for coleoptile pigmentation, all 4 genes were expressed in the red coleoptile; however, DFR was not activated in the white coleoptile. The Rc gene appears to be involved in DFR expression. The possibility that wheat R and Rc genes might be transcription factors is discussed.


flavanone

The formation of alkoxyl radical during metal ion breakdown of hydroperoxide-enriched Me linoleate of sunflower oil has been established by a combination of spin trapping and ESR spectroscopy. The influence of different concns. (10-100 μmol dm-3) of myricetin, quercetin, morin, kaempferol, rutin, fisetin, diosmetin, apigenin, luteolin, and naringenin, resp., on the formation and transformation of alkoxyl radical was evaluated. Results demonstrated that the antioxidative activity depends on the structure and concn. of applied flavonoids and it decreases in the following order: flavonol > flavone > flavanone. The formation of relatively stable free radicals for these flavonoid derivs. was studied. Under exptl. conditions employed, the generation of stable free radicals has been evidenced for myricetin, quercetin, rutin, and luteolin and their hyperfine coupling consts. were detd. The 2,3-double bond in conjugation with 4-oxo function and the addnl. presence of both 3- and 5-hydroxyl groups as well as o-dihydroxyl groups in the B-ring are very important for antioxidant activity of the investigated flavonoids and aroxyl radical stabilization.

Abstract

ESR study of the flavonoid effect on the metal ion breakdown of lipid peroxidation system. Djilas, S. M.; Canadanovic-Brunet, J. M.; Cetkovic, G. S.; Tumbas, V. T. Organic Chemistry Department, Faculty of Technology, University of Novi Sad, Novi Sad, Oxidation Communications (2005), 28(3), 547-554. Publisher: SciBulCom Ltd., CODEN: OXCODW ISSN: 0209-4541. Journal written in English. CAN 144:446700 AN 2005:1120883 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


For the fermentative prodn. of plant-specific flavanones (naringenin, pinocembrin) by Escherichia coli, a plasmid was constructed which carried an artificial biosynthetic gene cluster, including PAL encoding a phenylalanine ammonia-lyase from a yeast, ScCCL encoding a cinnamate/coumarate:CoA ligase from the actinomycete Streptomyces coelicolor A3(2), CHS encoding a chalcone synthase from a licorice plant and CHI encoding a chalcone isomerase from the Pueraria plant. The recombinant E. coli cells produced (2S)-naringenin from tyrosine and (2S)-pinocembrin from phenylalanine. When the two subunit genes of acetyl-CoA carboxylase from Corynebacterium glutamicum were expressed under the control of the T7 promoter and the ribosome-binding sequence in the recombinant E. coli cells, the flavanone yields were greatly increased, probably because enhanced expression of acetyl-CoA carboxylase increased a pool of malonyl-CoA that was available for flavanone synthesis. Under cultural conditions where E. coli at a cell d. of 50 g/l was incubated in the presence of 3 mM tyrosine or phenylalanine, the yields of naringenin and pinocembrin reached about 60 mg/l. The fermentative prodn. of flavanones in E. coli is the first step in the construction of a library of flavonoid compds. and un-natural flavonoids in bacteria.

Abstract

Efficient production of (2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster. Miyahisa, Ikuo; Kaneko, Masafumi; Funa, Nobutaka; Kawasaki, Hisashi; Kojima, Hiroyuki; Ohnishi, Yasuo; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Bunkyo-ku, Tokyo, Japan. Applied Microbiology and Biotechnology (2005), 68(4), 498-504. Publisher: Springer, CODEN: AMBIDG ISSN: 0175-7598. Journal written in English. CAN 144:50114 AN 2005:1124206 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The reaction of cellulose with N-carbonyl α-amino acid ester leading to corresponding cellulose carbamate was carried out in N,N-dimethylacetamide at 100 °C. For N-carbonyl L-leucine Et ester (I), the degree of the carbamate substituent (DS) in cellulose carbamate was 2.5 for I/[glucose units in cellulose] = 3.0 and reached ca. 3.0 for I/[glucose units in cellulose] = 4.0. One cellulose carbamate was highly sol. in not only aprotic polar solvents but also other org. solvents such as Et ether and Me alc. The chiral discrimination ability of this product was higher than those of the cellulose carbamates having L-phenylalanine and L-aspartic acid moieties.


flavanone

Non-parasitic leaf spots (NPLS) of barley cultivars Hordeum vulgare L. are a leaf damage which was obsd. only in the last fifteen years. It is unknown what the main reasons for these damages may be. The hypothesis that oxidative burst is the origin for these spots relies on the observation that they mostly occur when the radiation is high and the plants are in a defined stage of development. Several trials in climate chambers were made to investigate the development of the NPLS. For this reason the plants underwent different conditions, like enhanced sun radiation and high ozone concns. It could be demonstrated that the photon flux is important for the spot formation. In comparison to the resistant cultivar IPZ 24727 a significant higher level of superoxide anion radicals was found in the sensitive NPLS cultivar cv. Ricarda. Leaves of barley plants developed much more NPLS than the control plants when they were tested under high radiation conditions during the expts. This observations were also made in freeland trials. There was no correlation found between higher ozone concns. and the development of NPLS, but between stage of development of the barley and decrease of the spots. Even when the ears began to arise the spots developed very quickly. In view of this observation the antioxidative systems were analyzed. The concns. of ascorbate and glutathione decreased with growing age like the enzyme activity of Cu/Zn-SOD in the chloroplasts. A decrease of superoxide anion radicals was obsd. when the plants are grew older. In this stage of development it may be that the older leaves switch over to put their supply at seed's disposal. The hypothesis is that cultivars which are sensitive regarding to NPLS getting senescent earlier than the resistant cultivars. In this stage of development the plants are more

Abstract

Plantphysiological investigations of non-parasitic leaf spots of barley Hordeum vulgare L. Zahn, Martina. Institut fuer Meteorologie und Klimaforschung, Facultaet fuer Biologie, Universitaet Freiburg, Germany. Wissenschaftliche Berichte - Forschungszentrum Karlsruhe (2005), (FZKA 7128), i-xiii, 1-149. CODEN: WBFKF5 ISSN: 0947-8620. Report written in German. CAN 144:34136 AN 2005:1101192 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Functionalized SBA-15 mesoporous silica materials with a p6mm symmetry have been synthesized through a simple co-condensation approach of tetraethylorthosilicate (TEOS) and (3-(methylamino)propyl)trimethoxysilane (MAPTMS) using amphiphilic block co-polymers under acidic conditions. The influence of the amt. of MAPTMS in the initial synthesis mixt. on the mesostructural properties of the resultant materials was studied by varying the molar ratios of MAPTMS to TEOS. X-ray powder diffraction (XRD) and N2 sorption results indicated that the ordering of the mesoporous structure was dependent on the amt. of MAPTMS added in the initial mixt. Solid-state NMR, thermogravimetric anal. (TGA) and elemental anal. showed that the incorporation of the org. groups in the silica framework increased with the MAPTMS concn. in the synthesis mixt. TEOS pre-hydrolysis prior to the addn. of MAPTES had great influence on the crystallog. ordering, pore size, surface area and pore vol. of the resultant functionalized mesoporous silica materials. Moreover, the addn. of inorg. salt in the initial mixt. could greatly enhance the mesostructure ordering and stability of the mesoporous materials. With the aid of NaCl salt, the modified SBA-15 materials with the content of methylaminopropyl groups up to 2.37 mmol/g still possessed well-ordered mesoporous structure and had high specific area and pore vol. The modified SBA-15 showed high catalytic activities and selectivities toward flavanones synthesis through the Claisen-Schmidt condensation of substituted acetophenones and benzaldehyde derivs. and subsequent intramol. Michael addn. in the absence of solvent.

Abstract

Direct synthesis of highly ordered large-pore functionalized mesoporous SBA-15 silica with methylaminopropyl groups and its catalytic reactivity in flavanone synthesis. Wang, Xueguang; Tseng, Yao-Hung; Chan, Jerry C. C.; Cheng, Soofin. Department of Chemistry, National Taiwan University, Taipei, Taiwan. Microporous and Mesoporous Materials (2005), 85(3), 241-251. Publisher: Elsevier B.V., CODEN: MIMMFJ ISSN: 1387-1811. Journal written in English. CAN 145:271516 AN 2005:1119727 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Flavanones I, II, and III are manufd. by purifn. from propolis derived from plants including M. tanarius. Also claimed are antioxidants, useful as food additives, health foods, drugs, cosmetics, quasi-drugs, etc., contg. I, II, or III. Thus, propolis collected in Okinawa was extd. with EtOH under ultrasonication and fractionated by silica gel column and HPLC to give I, II, and III. Radical scavenging activity of I was comparable to that of eriodictyol.


Flavanones, their manufacture from propolis derived from Macaranga tanarius, and antioxidants containing them. Kumasawa, Shigenori; Nakayama, Tsutomu; Arakaki, Tsutomu; Fukumoto, Shuichi. (Pokka Corp., Japan). Jpn. Kokai Tokkyo Koho (2005), 16 pp. CODEN: JKXXAF JP 2005272374 A 20051006 Patent written in Japanese. Application: JP 2004-89552 20040325. Priority: . CAN 143:339688 AN 2005:1070490 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Twelve flavonoids, including seven flavones, four flavonols and one flavanone, were isolated from methanolic ext. of the herbal drug 'Crataegi folium cum flore' (hawthorn leaves and flowers) by a combination of CC (over Amberlite XAD-7 and Sephadex LH-20) and preparative HPLC. Their structures, including that of the novel flavonol 8-methoxykaempferol 3-O-(6''-malonyl-β-glucopyranoside), were elucidated by homo- and heteronuclear NMR and electrospray/MS. The 1H- and 13C-NMR of all compds., including rotameric pairs of five flavone C-glycosides, were assigned. The presence and relative proportion of each rotamer was shown by various NMR expts., including two-dimensional nuclear Overhauser and exchange spectroscopy, to depend on solvent, linkage position and structure of the C-glycosyl substituent.

Abstract

Isolation and identification of flavonoids, including flavone rotamers, from the herbal drug Crataegi folium cum flore (hawthorn). Rayyan, S.; Fossen, T.; Nateland, H. Solheim; Andersen, Oe. M. Department of Chemistry, University of Bergen, Bergen, Norway. Phytochemical Analysis (2005), 16(5), 334-341. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal written in English. CAN 144:280204 AN 2005:1078909 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The results of this investigations strengthen the assumption that the main reason for NPLS is an oxidative burst which is generated by environmental conditions. Radiation is an important factor but not the only one. In the NPLS sensitive cultivars ROS were not reduced in the way of the resistant cultivars because of an lower enzyme activity of Cu/Zn-SOD.

sensitive against oxidative burst and it may be that they react to high radiation with a marked manifestation of spots.


flavanone

Abstract

QSAR study of natural, synthetic and environmental endocrine disrupting compounds for binding to the androgen receptor. Zhao, C. Y.; Zhang, R. S.; Zhang, H. X.; Xue, C. X.; Liu, H. X.; Liu, M. C.; Hu, Z. D.; Fan, B. T. Department of Chemistry, Lanzhou University, Lanzhou, Peop. Rep. China. SAR and QSAR in Environmental Research (2005), 16(4), 349-367. Publisher: Taylor & Francis Ltd., CODEN: SQERED ISSN: 1062-936X. Journal written in English. CAN 143:320310 AN 2005:1069421 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

OH

HO

OHMeMe Me

HO

O

O

OH

HO

OH

Me Me Me

OH

O

O

OH

HO

OH

Me

Me

Me

I

III

II


flavanone

Preparative high-speed counter-current chromatog. (HSCCC) was successfully used for isolation and sepn. 3 of flavonoids including bolusanthol B, a novel compd. named 5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl) flavanone and tetrapterol I from Patrinia villosa Juss using 2-phase solvent system composed of n-hexane-Et acetate-methanol-water at the vol. ratio of 10:11:11:8 (vol./vol.). A total of 25.4 mg bolusanthol B, 52.5 mg 5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl) flavanone and 50.2 mg tetrapterol I were obtained from 250 mg crude ext. with purities of 96.8%, 99.2% and 99.3%, resp. detd. by HPLC in one single operation and less than 5 h. The structure identification was performed by UV, IR, MS, 1H NMR, 13C NMR and 2D NMR. Among them, bolusanthol B and tetrapterol I

Abstract

Preparative isolation and separation of a novel and two known flavonoids from Patrinia villosa Juss by high-speed counter-current chromatography. Peng, Jinyong; Yang, Genjin; Fan, Guorong; Wu, Yutian. Shanghai Key Laboratory for Pharmaceutical Metabolite Research, School of Pharmacy, Second Military Medical University, Shanghai, Peop. Rep. China. Journal of Chromatography, A (2005), 1092(2), 235-240. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 143:475006 AN 2005:1061242 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Primary plant surfaces, covered with cuticles consisting of cutin and waxes, are important substrates for interaction with insects. The compn. of leaf surfaces of the myrmecophilic plant Macaranga tanarius was studied. The prenylated flavanone nymphaeol-C was identified in surface exts. and was localized exclusively in glandular trichomes on the abaxial leaf side. The epidermal pavement cells surrounding these trichomes were covered with a smooth film of epicuticular wax from which few small wax crystals protruded. The epicuticular wax amounted to approx. 8 μg cm-2, corresponding to 85% of the wax load on the adaxial as well as the abaxial leaf sides. The epicuticular wax mixts. from both leaf surfaces contained more than 70% primary alcs., 14% fatty acids, 2% aldehydes, and traces of alkyl acetates, with chain lengths ranging from C20 to C38. In contrast, the intracuticular wax layer was largely dominated by triterpenoid alcs. α-amyrin, β-amyrin, and lupeol. Consequently, these characteristic compds. are not available for direct contact with insects on the plant surface.

Abstract

Surface composition of myrmecophilic plants: cuticular wax and glandular trichomes on leaves of Macaranga tanarius. Guhling, Ortwin; Kinzler, Christian; Dreyer, Michael; Bringmann, Gerhard; Jetter, Reinhard. Julius-von-Sachs Institut fuer Biowissenschaften, Universitaet Wuerzburg, Wuerzburg, Germany. Journal of Chemical Ecology (2005), 31(10), 2323-2341. Publisher: Springer Science+Business Media, Inc., CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 144:208866 AN 2005:1061451 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A large data set of 146 natural, synthetic and environmental chems. belonging to a broad range of structural classes have been tested for their relative binding affinity (expressed as log (RBA)) to the androgen receptor (AR). These chems. commonly termed endocrine disrupting compds. (EDCs) present a variety of adverse effects in humans and animals. As assays for binding affinity remains a time-consuming task, it is important to develop predictive methods. In this work, quant. structure-activity relationships (QSARs) were detd. using three methods, multiple linear regression (MLR), radical basis function neural network (RBFNN) and support vector machine (SVM). Five descriptors, accounting for hydrogen-bonding interaction, distribution of at. charges and mol. branching degree, were selected from a heuristic method to build predictive QSAR models. Comparison of the results obtained from three models showed that the SVM method exhibited the best overall performances, with a RMS error of 0.54 log (RBA) units for the training set, 0.59 for the test set, and 0.55 for the whole set. Moreover, six linear QSAR models were constructed for some specific families based on their chem. structures. These predictive toxicol. models, should be useful to rapidly identify potential androgenic endocrine disrupting compds.


flavanone

Prokaryotic dioxygenase is known to catalyze arom. compds. into their corresponding cis-dihydrodiols without the formation of an epoxide intermediate. Biphenyl dioxygenase from Pseudomonas pseudoalcaligenes KF707 showed novel monooxygenase activity by converting 2(R)- and 2(S)-flavanone to their corresponding epoxides

Abstract

Epoxide formation on the aromatic B ring of flavanone by biphenyl dioxygenase of Pseudomonas pseudoalcaligenes KF707. Han, Jaehong; Kim, Song-Young; Jung, Jihyun; Lim, Yoongho; Ahn, Joong-Hoon; Kim, Su-Il; Hur, Hor-Gil. Metalloenzyme Research Group, BET Research Institute and Department of Biotechnology, Chung-Ang University, Anseong, S. Korea. Applied and Environmental Microbiology (2005), 71(9), 5354-5361. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 143:401584 AN 2005:1022417 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A four-step flavanone biosynthetic pathway was constructed and introduced into Saccharomyces cerevisiae. The recombinant yeast strain was fed with phenylpropanoid acids and produced the flavanones naringenin and pinocembrin 62 and 22 times more efficiently compared to previously reported recombinant prokaryotic strains. Microbial biosynthesis of the flavanone eriodictyol was also achieved.

Abstract

Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Yan, Yajun; Kohli, Abhijeet; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, State University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2005), 71(9), 5610-5613. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 143:438544 AN 2005:1022452 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


On treatment with NaN3/conc. H2SO4-HOAc, some (E)-3-(4-methoxybenzylidene)flavanones yield a new type of flavonoid-derived spirocyclic oxazolines in moderate yield. A plausible mechanism for formation of these products is suggested.

Abstract

Novel formation of spirocyclic oxazolines in the reaction of some (E)-3-(4-methoxybenzylidene)flavanones with NaN3/concentrate H2SO4-HOAc. Mallik, Asok K.; Chattopadhyay, Falguni; Patra, Amarendra. Department of Chemistry, Jadavpur University, Kolkata, India. Journal of Chemical Research (2005), (8), 543-545. Publisher: Science Reviews, CODEN: JCROA4 Journal written in English. CAN 144:390608 AN 2005:1027583 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


were obtained from the plant of Patrinia genius for the first time, and 5,7,2',6'-tetrahydroxy-6,8-di(γ,γ-dimethylallyl) flavanone was a novel prenylated flavonoid and discovered from nature for the first time.


flavanone

Answer 556:

The flavonoid content of citrus ext. were investigated with using Mg method, and its antioxidant activity was detd. with DPPH and H2O2 assay. Hesperidin was shown to be the main flavonoid present in citrus family, it is chelated with Mg in an acidic envuronment and displays a cherry red color having UV absorbance max. at 560 nm. Flavanone content was 9.2±017 g/100g in citrus aurantium peel ext. Citrus ext. showed excellent scavenging effects on stable radical DPPH at a concn. of 1.6 mg/mL. Citrus ext. showed H2O2 scavenging ability. These results demonstrated that citrus ext. possess high amt. of flavonoids and excellent antioxidant activity.

Abstract

Determination of flavanone content and antioxidant activity of Citrus aurantium. Hosseinimehr, S. J. Department of Medicinal Chemistry, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran. Chemistry (Rajkot, India) (2004), 1(9), 635-638. Publisher: Trade Science Inc., CODEN: CHEMCT ISSN: 0972-8376. Journal written in English. CAN 144:167310 AN 2005:1016476 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Polyphenolic flavonoids are among a wide variety of phytochems. present in the human diet. Basic research, animal model, and human studies suggest flavonoid intake may reduce the risk of several age-related chronic diseases. The vast no. of flavonoids and mixts. of their subclasses, including flavonols, flavones, and flavanones, and the variety of agricultural practices that affect their concn. in foods have presented a challenge to the development of adequate food compn. databases for these compds. Nonetheless, dietary assessments have been applied to cohort and case-control epidemiol. studies, and several reveal an inverse assocn. with risk of some forms of cancer, cardiovascular disease, and other chronic conditions. Those observational studies that have examd. these relationships with regard to flavonols, flavones, and flavanones are reviewed. The requirement for caution in interpreting these studies is discussed with regard to the limited information available on the bioavailability and biotransformation of these flavonoids. As the totality of the available evidence on these flavonoids suggests a role in the prevention of cancer and cardiovascular disease, further research is warranted, particularly in controlled clin. trials.

Abstract

Flavonols, Flavones, Flavanones, and Human Health: Epidemiological Evidence. Graf, Brigitte A.; Milbury, Paul E.; Blumberg, Jeffrey B. Antioxidants Research Laboratory, Jean Mayer USDA Human Nutrition Research Center on Aging, Tufts University, Boston, MA, USA. Journal of Medicinal Food (2005), 8(3), 281-290. Publisher: Mary Ann Liebert, Inc., CODEN: JMFOFJ ISSN: 1096-620X. Journal; General Review written in English. CAN 144:232126 AN 2005:1020091 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(2-(7-oxabicyclo[4.1.0]hepta-2,4-dien-2-yl)-2,3-dihydro-4H-chromen-4-one), whereby the epoxide bond was formed between C2' and C3' on the B ring of the flavanone. The enzyme also converted 6-hydroxyflavanone and 7-hydroxyflavanone, which do not contain a hydroxyl group on the B-ring, to their corresponding epoxides. In a previous report, however, the authors found that the same enzyme showed dioxygenase activity toward flavone, resulting in the prodn. of flavone cis-2',3'-dihydrodiol. Extensive structural identification of the metabolites of flavanone by using HPLC, liq. chromatog./mass spectrometry, and NMR confirmed the presence of an epoxide functional group on the metabolites. Epoxide formation as the initial activation step of arom. compds. by oxygenases has been reported to occur only by eukaryotic monooxygenases. To the best of the authors' knowledge, biphenyl dioxygenase from P. pseudoalcaligenes KF707 is the first prokaryotic enzyme detected that can produce an epoxide deriv. on the arom. ring structure of flavanone.


flavanone

A process for producing picolinic acid compds. from phenyl-contg. arom. compds. by enzymic synthesis in engineered microbes expressing biphenyl catabolic enzyme genes, is disclosed. The process, which is for producing picolinic acid compds., comprises reacting phenyl-contg. arom. compds. represented by the following formula (I; Y = (substituted) heterocycly, Ph, or cyclic hydrocarbyl; Y ≠ diphenylacetylene; X = single bond, (substituted)-C1-4-alkylene or alkenylene) with an arom. ring dioxygenase, an arom. ring dihydrodiol dehydrogenase, and an arom. ring diol dioxygenase to obtain picolinic acid compds. (II; X,Y as in I). The comprehensive bioconversion of arom. compds. with a benzene ring to a picolinic acid was achieved with a recombinant Escherichia coli strain that expressed the six genes involved in biphenyl catabolism, these being the bphA1(2072)A2A3A4 genes encoding the evolved biphenyl dioxygenase, the bphB gene encoding dihydrodiol dehydrogenase, and the bphC gene encoding catechol 2,3-dioxygenase.

Abstract WO 2005-JP2755 W 20050222JP 2004-61238 A 20040304Priority Application

R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IS, IT, LI, LT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR

EP 1726645 A1 20061129 EP 2005-719369 20050222


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Conversion from arenes having a benzene ring to those having a picolinic acid using Escherichia coli that express bacterial genes involved in biphenyl catabolism. Shindo, Kazutoshi; Kagami, Osamu; Misawa, Norihiko; Furukawa, Kensuke. (Marine Biotechnology Institute Co., Ltd., Japan). PCT Int. Appl. (2005), 60 pp. CODEN: PIXXD2 WO 2005085435 A1 20050915 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SM, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2005-JP2755 20050222. Priority: JP 2004-61238 20040304. CAN 143:304749 AN 2005:1004874 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 559:

A review. Eukaryotic cellular machineries including the genome face continuous challenge from environmental deleterious agents, as well as from the by products of their own metab. Our skin is the most important barrier. It protects us from xenobiotic and genotoxic agents including UV solar radiation and potential carcinogens, which are notorious for causing skin cancer. There is a rise in non-melanoma skin cancer (NMSC), which is diagnosed in more than a million people every year in the United States alone, and is also prevalent in the other Western countries. In addn. to sunscreens, chemoprevention of skin cancer by natural non-toxic compds. is suggested as an effective strategy to prevent the incidence of skin cancer. Our extensive animal studies on silibinin, a non-toxic bioactive component in milk thistle, suggest that it has a strong potential to prevent skin cancer incidence, promotion and progression in response to chem. carcinogens and tumor promoters as well as UV radiation. Our data suggest that silibinin has multiple targets in the cell, and can be protective against the harmful effects of cytotoxic agents such as reactive oxygen species and inflammation. Further, silibinin modulates mitogenic and survival signaling, p53, Cip1/p21 and other cell cycle regulatory mols. to prevent UVB-induced skin carcinogenesis. Our ongoing studies also suggest the pos. effect of silibinin on the repair of UVB-induced DNA damage in mouse skin. Overall, the protective efficacy of silibinin against skin cancer is supported by sound mechanistic rationale in animal and cell culture studies, and suggests its potential use for humans.

Abstract

Mechanisms and preclinical efficacy of silibinin in preventing skin cancer. Singh, Rana P.; Agarwal, Rajesh. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado at Denver and Health Sciences Center, Denver, CO, USA. European Journal of Cancer (2005), 41(13), 1969-1979. Publisher: Elsevier Ltd., CODEN: EJCAEL ISSN: 0959-8049. Journal; General Review written in English. CAN 144:100090 AN 2005:978152 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Proline is utilized as an efficient organocatalyst for the synthesis of substituted flavanones and chalcones in good yields. The efficiency of the catalyst was proved with a variety of substrates ranging from electron-deficient to electron-rich aryl aldehydes and 2-hydroxyacetophenones.

Abstract

New synthesis of flavanones catalyzed by L-proline. Chandrasekhar, S.; Vijeender, K.; Reddy, K. Venkatram. Indian Institute of Chemical Technology, Hyderabad, India. Tetrahedron Letters (2005), 46(41), 6991-6993. Publisher: Elsevier B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN 143:422169 AN 2005:980491 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


N

CO 2H

XY XYI II


flavanone

Japanese cultivated gentian plants have naturally blue flowers, but some white-flowered cultivars are being bred through the utilization of spontaneous mutants. To det. the mol. basis of white coloration in gentian flowers, we compared two white-flowered cultivars Homoi and Polano White to a blue-flowered cultivar Maciry using biochem. and mol. approaches. High performance liq. chromatog. (HPLC) analyses showed that flavone levels in cv. Polano White were only about one-half the amts. measured in the other two cultivars, while anthocyanins were absent in the two white-flowered cultivars compared to cv. Maciry in which high levels accumulated. Northern blot anal. of 10 flavonoid biosynthetic structural genes, previously reported to be temporally regulated in cv. Maciry showed that cv. Homoi lacked transcripts for the anthocyanidin synthase (ANS) gene while cv. Polano White had decreased expressions for ANS as well as for chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), flavonoid 3',5'-hydroxylase (F3',5'H), dihydroflavonol 4-reductase (DFR), UDP-glucose:flavonoid 3-glucosyltransferase (3GT) and anthocyanin 5-arom. acyltransferase (5AT). Southern blot anal. confirmed the deficiency of one of two ANS loci in cv. Homoi. Transient expression of ANS in flower petals also strongly suggested that white flowers of cv. Homoi were derived from ANS mutation. Furthermore, anal. of stress-induced flower pigmentation suggested that rather than mutations in multiple structural genes being the cause, a defect in one or more regulatory factors controlling the later steps of flavonoid biosynthesis is responsible for white coloration in cv. Polano White.

Abstract

Two different mutations are involved in the formation of white-flowered gentian plants. Nakatsuka, Takashi; Nishihara, Masahiro; Mishiba, Keiichiro; Yamamura, Saburo. Iwate Biotechnology Research Center, Kitakami, Iwate, Japan. Plant Science (Amsterdam, Netherlands) (2005), 169(5), 949-958. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 144:146599 AN 2005:974293 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1), catalyzing the intracellular activation of cortisone to cortisol, is currently considered a promising target to treat patients with metabolic syndrome; hence, there is considerable interest in the development of selective inhibitors. For preclin. tests of such inhibitors, the characteristics of 11β-HSD1 from the commonly used species have to be known. Therefore, we detd. differences in substrate affinity and inhibitor effects for 11β-HSD1 from six species. The differences in catalytic activities with cortisone and 11-dehydrocorticosterone were rather modest. Human, hamster and guinea-pig 11β-HSD1 displayed the highest catalytic efficiency in the oxoredn. of cortisone, while mouse and rat showed intermediate and dog the lowest activity. Murine 11β-HSD1 most efficiently reduced 11-dehydrocorticosterone, while the enzyme from dog showed lower activity than those from the other species. 7-Ketocholesterol (7KC) was stereospecifically converted to 7β-hydroxycholesterol by recombinant 11β-HSD1 from all species analyzed except hamster, which showed a slight preference for the formation of 7α-hydroxycholesterol. Importantly, guinea-pig and canine 11β-HSD1 displayed very low 7-oxoreductase activities. Furthermore, we demonstrate significant species-specific variability in the potency of various 11β-HSD1 inhibitors, including endogenous compds., natural chems. and pharmaceutical compds. The results suggest significant differences in the three-dimensional organization of the hydrophobic substrate-binding pocket of 11β-HSD1, and they emphasize that species-specific variability must be considered in the interpretation of results obtained from different animal expts. The assessment of such differences, by cell-based test systems, may help to choose the appropriate animal for safety and efficacy studies of novel potential drug candidates.

Abstract

Comparative enzymology of 11β-hydroxysteroid dehydrogenase type 1 from six species. Arampatzis, Spyridon; Kadereit, Bert; Schuster, Daniela; Balazs, Zoltan; Schweizer, Roberto A. S.; Frey, Felix J.; Langer, Thierry; Odermatt, Alex. Division of Nephrology and Hypertension, Department of Clinical Research, University of Berne, Bern, Switz. Journal of Molecular Endocrinology (2005), 35(1), 89-101. Publisher: Society for Endocrinology, CODEN: JMLEEI ISSN: 0952-5041. Journal written in English. CAN 144:427798 AN 2005:977274 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


Grapefruit (Citrus paradise Macf.) (gr); Valencia orange (C. sinensis Osbeck) (vi); Sour orange (C. aurantium L.) (lr); Lemon (C. limon L.) (ad); Balady mandarin (C. reticulate Blanco) (y); Balady orange (C. sinensis Osbeck) (or) methanolic HCl exts. have been analyzed for antioxidative properties in their leaves L, peels P and seeds S. For the last two citrus, only leaves were extd. and evaluated. The results showed that grapefruit leaves, lemon seeds and valencia peel exts. have the highest antioxidative property (AOA). Comparing phenol content, lemon leaves, grapefruit seeds and sour orange peel exts. have the highest phenolic amts. of all analyzed samples. In spite of that citrus seeds contain the lowest mean phenols amts., they showed mean AOA more than 93% comparing to that for control. The chem. compn. was investigated using GC-MS for the citrus seed methanolic exts. (SME). Three major peaks were detected and identified as hexadecanoic acid Me ester (I), flavanone derivs. specifically a pentahydroxy dimethoxy flavone (II), and Kaempferide (III) a methoxy deriv. The grapefruit seed methanolic ext. has the highest amt. of compds. (I, III). Valencia seed ext. has the highest amt. of compd. (II). Valencia seed ext. has the lowest content of compds. (I, III) and the lemon seed ext. has the lowest content for compd. (II).

Abstract

Stability of methanolic extract activity for leaves, peels and citrus seeds under UV irradiation. Shaker, Emad S. Agricultural Chemistry Department, Faculty of Agriculture, Minia University, Minia, Egypt. Special Publication - Royal Society of Chemistry (2005), 300(Food Flavor and Chemistry), 472-483. Publisher: Royal Society of Chemistry, CODEN: SROCDO ISSN: 0260-6291. Journal written in English. CAN 144:149319 AN 2005:968519 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The potential health benefits of dietary isoflavones have generated considerable interest in engineering the synthesis of these phytoestrogens into plants. Genistein glucoside prodn. (up to 50 nmol g-1 fresh wt.) was engineered in alfalfa (Medicago sativa) leaves by constitutive expression of isoflavone synthase from Medicago truncatula (MtIFS1). Glucosides of biochanin A (4'-O-methylgenistein) and pratensein (3'-hydroxybiochanin A) also accumulated. Although MtIFS1 was highly expressed in all organs examd., genistein accumulation was limited to leaves. MtIFS1-expressing lines accumulated several addnl. isoflavones, including formononetin and daidzein, in response to UV-B or Phoma medicaginis, whereas the chalcone and flavanone precursors of these compds. accumulated in control lines. Enhanced accumulation of the phytoalexin medicarpin was obsd. in P. medicaginis-infected leaves of MtIFS1-expressing plants. Microarray profiling indicated that MtIFS1 expression does not significantly alter global gene expression in the leaves. Our results highlight some of the challenges assocd. with metabolic engineering of plant natural products, including tissue-specific accumulation, potential for further modification by endogenous enzyme activities (hydroxylation, methylation, and glycosylation), and the differential response of engineered plants to environmental factors.

Abstract

Metabolic engineering of isoflavonoid biosynthesis in alfalfa. Deavours, Bettina E.; Dixon, Richard A. Plant Biology Division, Samuel Roberts Noble Foundation, Ardmore, OK, USA. Plant Physiology (2005), 138(4), 2245-2259. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 143:418993 AN 2005:969635 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

CCC sample cutting for isolation of prenylated phenolics from hops. Chadwick, Lucas R.; Fong, Harry H. S.; Farnsworth, Norman R.; Pauli, Guido F. UIC/NIH Center for Botanical Dietary Supplements Research, Department of Medicinal Chemistry and Pharmacognosy, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA. Journal of Liquid Chromatography & Related Technologies (2005), 28(12-13), 1959-1969. Publisher: Taylor & Francis, Inc., CODEN: JLCTFC ISSN: 1082-6076. Journal written in English. CAN 144:166583 AN 2005:965909 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The radical-scavenging activities of the flavanones hesperetin and hesperidin were investigated by differential scanning calorimetry (DSC) monitoring of the polymn. of Me methacrylate initiated by 2,2'-azobisisobutyronitrile (AIBN, an R.bul. radical) or benzoyl peroxide (BPO, a PhCOO.bul. radical) at 70°C under nearly anaerobic conditions. Their stoichiometric factor (no. of free radicals trapped by one mole of antioxidant moiety (n)) and the ratio of the rate const. of inhibition to that of propagation (kinh/kp) were detd. and compared with that for trolox. The n value declined in the order trolox (2.0) > hesperetin (0.8) > hesperidin (0.2) in the AIBN system, whereas it declined in the order hesperetin (0.9) > trolox (0.1) > hesperidin (0.0) in the BPO system. The kinh/kp value declined in the order hesperidin (195) > hesperetin (33) > trolox (12) in the AIBN system, whereas it declined in the order hesperidin (362) > trolox (127) > hesperetin (18) in the BPO system. The n value of about 1 for hesperetin with a relatively small kinh/kp value suggests the formation of dimers, as a result of the coupling reaction of phenolic monomers. In contrast, n values < < 1 for hesperidin and trolox in the BPO system resulted in very high values for kinh/kp Hesperidin was also much more able to suppress the growth of Me methacrylate radicals, although its n value was small, suggesting that this compd. may also suppress polyunsatd. fatty acid radicals. In the concn. range 250-500 μM, hesperetin and hesperidin showed potent inhibition of LPS-induced expression of the COX-2 gene in RAW 264.7 cells, suggesting the anti-inflammatory activity of these compds. The ability of hesperetin and hesperidin to suppress COX-2 gene expression may be a consequence of their antioxidant activity.

Abstract

Kinetics of radical-scavenging activity of hesperetin and hesperidin and their inhibitory activity on COX-2 expression. Hirata, Atsusi; Murakami, Yukio; Shoji, Masao; Kadoma, Yoshinori; Fujisawa, Seiichiro. Department of Oral Diagnosis, Meikai University School of Dentistry, Saitama, Japan. Anticancer Research (2005), 25(5), 3367-3374. Publisher: International Institute of Anticancer Research, CODEN: ANTRD4 ISSN: 0250-7005. Journal written in English. CAN 143:318303 AN 2005:966362 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method for quant. detn. of flavanones existing in mandarin (Citrus unshiu) fruit skin is described. Maximal extn. of flavanones from the air-dried skin was performed with methanol and the measurement was by spectrometry.

Abstract

Method of quantitative determination of flavanones. Menteshashvili, M.; Samsonia, Sh.; Shalashvili, A.; Targamadze, I. Tbilisi State Univ., Tbilisi, Georgia. Sakartvelos Mecnierebata Akademiis Macne, Kimiis Seria (2005), 31(1-2), 181-183. Publisher: Proizvodstvenno-IzdatelÏskoe ObÏedinenie "Metsniereba", CODEN: IANKEJ Journal written in English. CAN 145:58540 AN 2005:968012 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Natural Products as Scaffolds for Chemical Diversification: Solution-Phase Parallel Synthesis of a Series of Naringin Analogs. Hanessian, Stephen; Kothakonda, Kiran Kumar. Department of Chemistry, University of Montreal, Montreal, QC, Can. Journal of Combinatorial Chemistry (2005), 7(6), 837-842. Publisher: American Chemical Society, CODEN: JCCHFF ISSN: 1520-4766. Journal written in English. CAN 143:406063 AN 2005:921242 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids (FL) are able to reduce, add or oxidize α-hydroxyethyl radicals (HER). The probability of these processes to occur depends on the structure of the FL under study. Namely, to cause redn. of HER, the presence of hydroxyl groups is necessary, and to effect oxidn. or addn. of HER, the presence of a carbonyl group at C4 and a C2-C3 double bond in the C ring is required.

Abstract

Reactions of α-hydroxyethyl radicals with flavonoids of various structures. Hryntsevich, I. B.; Shadyro, O. I. Department of Chemistry of the Belarussian State University, Minsk, Belarus. Bioorganic & Medicinal Chemistry Letters (2005), 15(19), 4252-4255. Publisher: Elsevier B.V., CODEN: BMCLE8 ISSN: 0960-894X. Journal written in English. CAN 143:367110 AN 2005:921419 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chromatog. resoln. of four flavanones is achieved by reversed-phase HPLC on a chiral stationary phase based on silica coated with a (2-hydroxy-3-methacryloyloxypropyl β-cyclodextrin-co-N-vinylpyrrolidone) copolymer. The influence of the mobile phase water content and the nature of the org. modifier on the retention and resoln. is evaluated. Monosubstituted flavanones are better resolved than the unsubstituted one. Nevertheless, the 6- and 7-methoxy substituents enhance retention and chiral recognition to polymeric β-cyclodextrin stationary phase less than the 6-hydroxy group. (c) 2005 Preston Publications.

Abstract

High-performance liquid chromatographic enantioseparation of flavanones on 2-hydroxy-3-methacryloyloxypropyl β-cyclodextrin copolymer coated silica phase. Carbonnier, Benjamin; Janus, Ludovic; Morcellet, Michel. Laboratoire de Chimie Macromoleculaire, UMR CNRS 8009, Universite des Sciences et Technologies de Lille, Villeneuve d'Ascq, Fr. Journal of Chromatographic Science (2005), 43(7), 358-361. Publisher: Preston Publications, CODEN: JCHSBZ ISSN: 0021-9665. Journal written in English. CAN 144:323789 AN 2005:943651 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


One of the most potent estrogenic substances from the plant kingdom is the prenylated flavanone, 8-prenylnaringenin (8PN), present in hops (Humulus lupulus L., Cannabaceae) in low (<10 ppm) concns. The prenylated chalcone desmethylxanthohumol (DMX), which is also present in this plant material, serves as a precursor to 8PN. A method for the preparative isolation of these and related bioactive phytochems. has been developed that involves the use of multiple chromatog. techniques including complementary countercurrent chromatog. (CCC) solvent systems. This paper describes the isolation of 8PN and DMX employing "sample-cutting CCC". The Hexanes-EtOAc-MeOH-H2O (HEMWat) solvent systems found to be effective for isolation of prenylated phenolics from hops range from HEMWat 8-2-8-2 for diprenylxanthohumol and 6,8-diprenylnaringenin, to HEMWat 6-4-6-4 for xanthohumol (XH), 6-prenylnaringenin (6PN) and 8PN, to HEMW at 5-5-5-5 for DMX, hydroxylated derivs. of XH, and humulinones.


flavanone

Remedy containing 3-hydroxy-3-methylglutaryl-CoA reductase inhibitor and/or cell foaming inhibitor. Enoki, Tatsuji; Kudo, Yoko; Sugiyama, Katsumi; Ohnogi, Hiromu; Sagawa, Hiroaki; Kato, Ikunoshin. (Takara Bio Inc., Japan). PCT Int. Appl. (2005), 91 pp. CODEN: PIXXD2 WO 2005074906 A1 20050818 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO,


Microwave irradn. of chalcones under solvent-free conditions resulted in a green chem. procedure for the prepn. of flavanones in very good yields. Using an unmodified household microwave oven, different mineral supports, and catalysts were tested. By irradn. of chalcones with 30% TFA over silica gel, eleven known flavanones and five new compds. were prepd. in high yields.

Abstract

Microwave-accelerated solvent-free synthesis of flavanones. Sagrera, Gabriel J.; Seoane, Gustavo A. Departamento de Quimica Organica, Facultad de Ciencias Universidad de la Republica, Montevideo, Urug. Journal of the Brazilian Chemical Society (2005), 16(4), 851-856. Publisher: Sociedade Brasileira de Quimica, CODEN: JOCSET ISSN: 0103-5053. Journal written in English. CAN 144:274018 AN 2005:842633 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A novel flavanone glycoside, (2S)-4',5,6,7-tetrahydroxyflavavone 6-O-β--glucopyranoside was isolated from the Et acetate ext. of the flowers of Carthamus tinctorium by high-speed counter-current chromatog. (HSCCC). Using an optimized two-phase solvent system composed of Et acetate-methanol-water (5:1:5, vol./vol.), target compd. (52 mg) with purity of 98.0% was obtained from 2.0 g of sample by HSCCC in seven times run. The structure of the target compd. was elucidated by spectroscopic methods including IR, MS, 1D and 2D NMR techniques.

Abstract

Isolation of a novel flavanone 6-glucoside from the flowers of Carthamus tinctorium (Honghua) by high-speed counter-current chromatography. Zhao, Mingbo; Ito, Yoichiro; Tu, Pengfei. School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing, Peop. Rep. China. Journal of Chromatography, A (2005), 1090(1-2), 193-196. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 143:382028 AN 2005:901347 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The flavanone glycoside naringin hydrate is widely abundant in various citrus plants. As an ongoing effort toward the exploitation of natural products as scaffolds for chem. diversification at readily accessible positions, we have prepd. a series of analogs of naringin in which the 6-hydroxyl group of the β-D-glucopyranosyl subunit was converted to sulfonamides, amides, urethanes, and secondary and tertiary amines via the corresponding 6-amino deriv. using a soln.-phase parallel array protocol.

Abstract


flavanone

During the biosynthesis of the tricyclic flavonoid natural products in plants, oxidative modifications to the central C-ring are catalyzed by Fe(II) and 2-oxoglutarate dependent oxygenases. The reactions catalyzed by three of these enzymes; flavone synthase I, flavonol synthase and anthocyanidin synthase (ANS), are formally desaturations. In comparison, flavanone 3β-hydroxylase catalyzes hydroxylation at the C-3 pro-R position of 2S-naringenin. Incubation of ANS with the unnatural substrate (±)-naringenin results in predominantly C-3 hydroxylation to give cis-dihydrokaempferol as the major product; trans-dihydrokaempferol and the

Abstract

Structural and mechanistic studies on anthocyanidin synthase catalyzed oxidation of flavanone substrates: the effect of C-2 stereochemistry on product selectivity and mechanism. Welford, Richard W. D.; Clifton, Ian J.; Turnbull, Jonathan J.; Wilson, Stuart C.; Schofield, Christopher J. Chemical Research Laboratory, Department of Chemistry, Oxford Centre for Molecular Sciences, Oxford, UK. Organic & Biomolecular Chemistry (2005), 3(17), 3117-3126. Publisher: Royal Society of Chemistry, CODEN: OBCRAK ISSN: 1477-0520. Journal written in English. CAN 143:381656 AN 2005:800501 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


It is intended to provide a drug, a food, a drink or a feed for treating or preventing diseases, wherein an effect of inhibiting 3-hydroxy-3-methylglutaryl-CoA reductase and/or an effect against cell foaming are needed for the prevention or treatment, characterized by contg., as the active ingredient, at least one compd. selected from the group consisting of chalcone compds., flavanone compds., 3',4'-dihydroseseline compds., derivs. thereof and salts thereof. The above-described drug, food, drink or feed is useful in treating or preventing, for example, hyperlipemia, arteriosclerosis and various diseases caused mainly thereby. For example, xanthoangelol was isolated from Angelica Keiskei root ext., and examd. for its HMG-CoA reductase inhibitory effect in vitro.

Abstract JP 2004-31173 A 20040206Priority Application




RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2005-JP1655 20050204. Priority: JP 2004-31173 20040206. CAN 143:199938 AN 2005:823550 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

A new lupane triterpenoid, 3α-hydroxy-20-oxo-30-norlupane (I) plus its β epimer (II), and a new flavanone (nubatin; III) have been isolated from Salvia nubicola collected from Quetta, Pakistan. The structures of these constituents were elucidated with the aid of spectroscopic techniques, including two-dimensional NMR and NOE expts. Both the metabolites were found to be moderately bio-active.

Abstract

Characterization and bioscreening of a new triterpenoid and a flavanone isolated from Salvia nubicola. Ali, Muhammad S.; Ahmed, Shakeel; Ibrahim, Syed A.; Tareen, Rasool B. H. E. J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi, Pak. Chemistry & Biodiversity (2005), 2(7), 910-916. Publisher: Verlag Helvetica Chimica Acta AG, CODEN: CBHIAM ISSN: 1612-1872. Journal written in English. CAN 144:146515 AN 2005:781141 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


desatn. product, apigenin are also obsd. Labeling studies have demonstrated that some of the formal desatn. reactions catalyzed by ANS proceed via initial C-3 hydroxylation followed by dehydration at the active site. We describe analyses of the reaction of ANS with 2S- and 2R-naringenin substrates, including the anaerobic crystal structure of an ANS-Fe-2-oxoglutarate-naringenin complex. Together the results reveal that for the 'natural' C-2 stereochem. of 2S-naringenin, C-3 hydroxylation predominates (>9:1) over desatn., probably due to the inaccessibility of the C-2 hydrogen to the iron center. For the 2R-naringenin substrate, desatn. is significantly increased relative to C-3 hydroxylation (.apprx.1:1); this is probably a result of both the C-3 pro-S and C-2 hydrogen atoms being accessible to the reactive oxidizing intermediate in this substrate. In contrast to the hydroxylation-elimination desatn. mechanism for some ANS substrates, the results imply that the ANS catalyzed desatn. of 2R-naringenin to form apigenin proceeds with a syn-arrangement of eliminated hydrogen atoms and not via an oxygenated (gem-diol) flavonoid intermediate. Thus, by utilizing flavonoid substrates with different C-2 stereochemistries, the balance between C-3 hydroxylation or C-2, C-3 desatn. mechanisms can be altered.


flavanone

Flavonoids are a large class of naturally occurring arom. secondary plant metabolites. They constitute one of the most characteristic classes found in nature and more than 4000 flavonoids have been identified and divided into several subclasses. Flavonoids have several effects on human health, mainly related to their antioxidant activity. As a result of the increased interest in the biol. active compds. in food, many research studies have investigated the detection and quantification of antioxidants. Citrus plants are of great interest since they accumulate large amts. of flavonoids and fruit and juices of these species are consumed in large quantities. Despite the extensive research performed on Citrus flavonoids, many compds. still remain unidentified. In this work, flavonoids of 5 citrus juices: lemon, grapefruit, bergamot, orange, and mandarin were analyzed by micro-HPLC coupled online with an MS detector equipped with an ESI source operating in neg. mode. The use of microcolumn HPLC greatly enhanced detection performance. In total, 20 flavonoids of two different subclasses (flavanone and flavone glycosides) were identified with the help of retention data and MS spectral information.

Abstract

Determination of flavonoids in citrus juices by micro-HPLC-ESI/MS. Dugo, Paola; Lo Presti, Maria; Oehman, Marcus; Fazio, Alessia; Dugo, Giovanni; Mondello, Luigi. Dipartimento di Chimica Organica e Biologica, Facolta di Scienze, Universita di Messina, Messina, Italy. Journal of Separation Science (2005), 28(11), 1149-1156. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 143:404705 AN 2005:780969 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


CO

MeMe

Me Me

Me

Me

CH 3

H

H

H

H

HO

CO

MeMe

Me Me

Me

Me

CH 3

H

H

H

H

HO

O

O

MeO

MeO

OH

OH

OH

I

III

II


flavanone

3-Deoxyanthocyanins provide bright orange-red colors to flowers of some members of the Gesneriaceae, including sinningia (Sinningia cardinalis). We examd. 3-deoxyanthocyanin biosynthesis in sinningia, in particular, the expression of key flavonoid biosynthetic genes and the activities of the encoded proteins. Two abundant 3-deoxyanthocyanins, luteolinidin 5-O-glucoside and apigeninidin 5-O-glucoside, three flavone glycosides, luteolin 7-O-glucoside, luteolin 7-O-glucuronide and apigenin 7-O-glucuronide, and the cinnamic acid verbascoside were identified in sinningia petal tissue. Small amts. of a 3-hydroxyanthocyanin were also detected in a limited region of the petal. CDNA clones for three flavonoid enzymes, flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase/flavanone 4-reductase (DFR/FNR) and anthocyanidin synthase (ANS), were isolated from a sinningia cDNA library made from petal RNA and used to measure transcript abundance during petal development. Only very low levels of F3H transcript were detected, while DFR/FNR transcript was highly abundant. ANS transcript levels were intermediate between these two. The F3H cDNA was shown to encode a functional F3H protein by complementation of the phenotype of an Antirrhinum majus F3H mutant. The recombinant DFR/FNR had activity against both flavanone and dihydroflavonol substrates to a comparable extent. The results suggest a mechanism of 3-deoxyflavonoid biosynthesis in sinningia similar to that reported for Zea mays, in which lack of F3H activity allows action of the DFR/FNR on flavanone substrates and prodn. of flavan-4-ols. These are then likely converted to 3-deoxyanthocyanins through the action of the ANS and subsequent glucosylation.

Abstract

Investigation of the biosynthesis of 3-deoxyanthocyanins in Sinningia cardinalis. Winefield, Chris S.; Lewis, David H.; Swinny, Ewald E.; Zhang, Huaibi; Arathoon, H. Steve; Fischer, Thilo C.; Halbwirth, Heidrun; Stich, Karl; Gosch, Christian; Forkmann, Gert; Davies, Kevin M. New Zealand Institute for Crop and Food Research Limited, Palmerston North, N. Z. Physiologia Plantarum (2005), 124(4), 419-430. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 144:104022 AN 2005:743585 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The authors investigated the influence of induced fit of the androgen receptor binding pocket on free energies of ligand binding. On the basis of a novel alignment procedure using flexible docking, mol. dynamics simulations, and linear-interaction energy anal., the authors simulated the binding of 119 mols. representing six compd. classes. The superposition of the ligand mols. emerging from the combined protocol served as input for Raptor, a receptor-modeling tool based on multidimensional QSAR allowing for ligand-dependent induced fit. Throughout the authors' study, protein flexibility was explicitly accounted for. The model converged at a cross-validated R2 = 0.858 (88 training compds.) and yielded a predictive R2 = 0.792 (26 test compds.), thereby predicting the binding affinity of all compds. close to their exptl. value. The authors then challenged the model by testing five mols. not belonging to compd. classes used to train the model: the IC50 values were predicted within a factor of 4.5 compared to the exptl. data. The demonstrated predictivity of the model suggests that the authors' approach may well be beneficial for both drug discovery and the screening of environmental chems. for endocrine-disrupting effects, a problem that has recently become a cause for concern among scientists, environmental advocates, and politicians alike.

Abstract

Impact of Induced Fit on Ligand Binding to the Androgen Receptor: A Multidimensional QSAR Study To Predict Endocrine-Disrupting Effects of Environmental Chemicals. Lill, Markus A.; Winiger, Fabienne; Vedani, Angelo; Ernst, Beat. Institute for Molecular Pharmacy, University of Basel, Basel, Switz. Journal of Medicinal Chemistry (2005), 48(18), 5666-5674. Publisher: American Chemical Society, CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 143:243261 AN 2005:777849 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Red grain colour gene (R) of wheat is a Myb-type transcription factor. Himi, Eiko; Noda, Kazuhiko. Research Institute for Bioresources, Okayama University, Kurashiki, Japan. Euphytica (2005), 143(3), 239-242. Publisher: Springer, CODEN: EUPHAA ISSN: 0014-2336. Journal written in English. CAN 144:268250 AN 2005:710259 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two flavanones have been isolated from the pericarps of Ricinus communis (Euphorbiaceae). By means of spectroscopic methods their structures, were established as naringenin 7-O-(3''-p-coumaroylglucoside) and naringenin 7-O-(3'',6''-di-p-coumarylglucoside).

Abstract

Flavanones isolated from Ricinus Communis L. (Euphorbiaceae). Bahroun, A.; Ben Ameur, N.; Damak, M. Laboratoire de chimie des Substances Naturelles, Faculte des Sciences de Sfax, Sfax, Tunisia. Journal de la Societe Chimique de Tunisie (2002), 4(11), 1427-1431. Publisher: Societe Chimique de Tunisie, CODEN: JSCTDP ISSN: 0253-1208. Journal written in French. CAN 144:146513 AN 2005:715039 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The free radical copolymn. of vinylpyrrolidone (VP) with 2-hydroxy-3-methacryloyloxypropyl β-cyclodextrin (βW7 MAHP), a deriv. of hydroxypropyl β-cyclodextrin (CD) substituted by polymerizable methacryloyl groups, is carried out in water by varying the molar ratio of the comonomers. The higher the molar ratio of βW7 MAHP to VP, the larger the molar mass of the water-sol. copolymer. A size exclusion chromatog. anal. coupled with multiangle laser light scattering detection (SEC-MALLS) suggests that VP-rich copolymers with a mass-av. molar mass (MM) of about 2.5 × 104 g mol-1 may consist of βW7 MAHP dimers, trimers, and oligomers contg. few CD units whereas βW7 MAHP rich copolymers with an MM of about 5.5 × 106 g mol-1 are likely to be dominated by crosslinked polymer materials. βW7 MAHP-co-VP copolymers coated on porous silica are used as high-performance liq. chromatog. chiral selectors. The effects of the structural features of the guest mol. and the characteristics of the chiral stationary phases on the retention and resoln. are evaluated. SEC-MALLS detection shows that, by varying the comonomer feed, copolymers with different molar masses and macromol. structures are formed. The chiral sepn. ability of Copo VP is evaluated toward enantiomers having one or more arom. rings as a function of the amt. of copolymer adsorbed onto the silica surface, the βW7 MAHP content, and the concn. of solute. The column combining the greater amts. of adsorbed copolymer and βW7 MAHP exhibits better resolving power. Moreover, the size, geometry, and functionality of the guest mol. are important factors that strongly affect the enantioselectivity.

Abstract

Methacryloylpropyl-β-cyclodextrin and vinylpyrrolidone copolymers: Synthesis and characterization as potential chiral selector. Carbonnier, B.; Janus, L.; Deratani, A.; Morcellet, M. Laboratoire de Chimie Macromoleculaire, UPRESA CNRS 8009, Universite des Sciences et Technologies de Lille, Villeneuve d'Ascq, Fr. Journal of Applied Polymer Science (2005), 97(6), 2364-2374. Publisher: John Wiley & Sons, Inc., CODEN: JAPNAB ISSN: 0021-8995. Journal written in English. CAN 143:359184 AN 2005:734316 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Hesperidin (2S-form), the flavanone 7-O-glycoside, is the main constituent of some Citrus species. The peels of 2 Citrus species are used as a crude drug, Aurantii nobilis pericarpium, in the Japanese Pharmacopoeia and as components in Kampo formulas. Thus, HPLC anal. of hesperidin as a marker compd. is needed for quality control of medicines. Hesperidin was sepd. from the corresponding C-2 epimer by normal-phase HPLC using a chiral column. Moreover, narirutin and neohesperidin were also sepd. from the corresponding C-2 epimer. The analyses of com. hesperidin samples revealed that they contained the C-2 epimer and that the relative ratio of hesperidin to the epimer ranged from 92:8 to 59:41. The HPLC application to Citrus exts. suggested that naturally occurring hesperidin in Citrus has the 2S configuration; however, the dry exts. of rikkunshito and chotosan, which are Kampo formulations contg. Aurantii nobilis pericarpium, were found to contain a considerable amt. of the (2R)-epimer. These data suggest that the decoction process of the formulas partly converts hesperidin to the epimer. Because diastereomers differ from each other in physicochem. and

Abstract

HPLC separation of hesperidin and the C-2 epimer in commercial hesperidin samples and herbal medicines. Uchiyama, Nahoko; Kim, Ik Hwi; Kawahara, Nobuo; Goda, Yukihiro. National Institute of Health Sciences (NIHS), Tokyo, Japan. Chirality (2005), 17(7), 373-377. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN 143:159723 AN 2005:702942 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Epidemiol. surveys have shown an inverse relationship between the intake of fruit and the incidence of coronary heart disease and some type of cancer. Data found in the literature regarding the flavonoids in general while this study focuses on flavanones, a subclass of flavonoids which occurs in Citrus fruit. The aim of this work is to elucidate the antioxidant or pro-oxidant behaviors of some common flavanones and to det. their activity-structure relationships as antioxidant using the crocin bleaching inhibition assay. The compds. studied were regarding both the aglycon form and the glycoside form. Data evidence that the substitution of the 7th OH group of the flavanones by a neohesperidoside influences the relationship between structure and antioxidant activity. In fact, the 3',4'-catechol structure and the O-methylation, in the aglycon forms, do not result significant. On the other hands, in the glycosylate forms, the 3',4'-catechol structure noticeably increases the antioxidant power and the O-methylation decreases the antioxidant activity. The influence of the O-glycosylation with a rutinose mol. is neglectable.

Abstract

Flavanones in citrus fruit: Structure-antioxidant activity relationships. Di Majo, Danila; Giammanco, Marco; La Guardia, Maurizio; Tripoli, Elisa; Giammanco, Santo; Finotti, Enrico. Institute of Physiology and Human Nutrition, University of Palermo, Palermo, Italy. Food Research International (2005), 38(10), 1161-1166. Publisher: Elsevier B.V., CODEN: FORIEU ISSN: 0963-9969. Journal written in English. CAN 145:144246 AN 2005:707384 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Red pigment of wheat grain was reported to be polyphenol compds., phlobaphene or proanthocyanidin, which were synthesized through the flavonoid biosynthesis pathway. We examd. the expression of four genes in the flavonoid pathway in developing wheat grains: chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), and dihydroflavonol 4-reductase (DFR). The expression of these genes in the white-grained wheat lines was reduced, compared with that in the red-grained wheats. These results suggest that the R genes for grain color, located on the long arms of chromosomes 3A, 3B and 3D, are transcriptional activators of the flavonoid synthesis genes. We identified three Myb-type transcription factors (Tamyb10-A1 on 3A, Tamyb10-B1 on 3B and Tamyb10-D1 on 3D), which were also located in the same region as the R loci, and were expressed predominantly in developing grains. In wheat lines with the recessive allele r3 (3B) Tamyb10-B1 had a deletion which caused a frame-shift in its open reading frame. Tamyb10-A1, and -D1 were not expressed in wheats with r2 (3A) and r1 (3D).


flavanone

Abstract

Antioxidant activity of extracts from fruit of Aroeira (Schinus terebenthifolius Raddi). Degaspari, C. H.; Waszczynskyj, N.; dos Santos, R. J. Aluna do Doulorado em Tecnologia de Alimentos, Universidade Federal do Parana, Brazil. Visao Academica (2004), 5(2), 83-89. Publisher: Universidade Federal do Parana, Dep. de Farmacia, CODEN: VAICA7 ISSN: 1518-5192. Journal written in Portuguese. CAN 143:365854 AN 2005:648219 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chem. components from the aerial part of the Kazakhstan population of Artemisia pontica, from which the rarely encountered flavonoids 7-O-methyl- and 4',7-di-O-Me esters of apigenin were isolated for the first time, were identified. The complete chem. compn. of the essential oil was established using GC-MS.

Abstract

Components of Artemisia pontica. Talzhanov, N. A.; Sadyrbekov, D. T.; Smagulova, F. M.; Mukanov, R. M.; Raldugin, V. A.; Shakirov, M. M.; Tkachev, A. V.; Atazhanova, G. A.; Tuleuov, B. I.; Adekenov, S. M. Institute of Phytochemistry, Ministry of Education and Science, Karaganda, Kazakhstan. Chemistry of Natural Compounds (2005), 41(2), 178-181. Publisher: Springer Science+Business Media, Inc., CODEN: CHNCA8 ISSN: 0009-3130. Journal written in English. CAN 144:124962 AN 2005:656761 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chem. variability of propolis is discussed with respect to the problem of standardization. Several chem. types of propolis are formulated, based on their plant source. Reliable criteria for chem. standardization of different propolis types are needed but such generally accepted criteria do not yet exist. The chem. profile of "poplar" propolis, typical for the temperate zone, can be characterized by the following parameters: total flavone and flavonol content, total flavanone and dihydroflavonol content, and total phenolics content. These parameters correlate better with the biol. activity and are more informative that the quantification of individual components. There is still a lot of work to be done to achieve standardization of other propolis types. Working with standardized material will allow scientists to connect a particular chem. propolis type to a specific type of biol. activity and formulate recommendations for mainstream practitioners.

Abstract

Chemical diversity of propolis and the problem of standardization. Bankova, Vassya. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulg. Journal of Ethnopharmacology (2005), 100(1-2), 114-117. Publisher: Elsevier Ireland Ltd., CODEN: JOETD7 ISSN: 0378-8741. Journal written in English. CAN 144:376144 AN 2005:686425 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


biol. activities, HPLC to sep. hesperidin from the C-2 epimer should be introduced into the letter of approval for herbal medicines.


flavanone

Breast cancer resistance protein (BCRP) is a newly identified ABC transporter, which plays an important role in drug disposition and represents an addnl. mechanism for the development of MDR. Flavonoids, a major class of natural compds. widely present in foods

Abstract

Structure activity relationships and quantitative structure activity relationships for the flavonoid-mediated inhibition of breast cancer resistance protein. Zhang, Shuzhong; Yang, Xinning; Coburn, Robert A.; Morris, Marilyn E. University at Buffalo, School of Pharmacy and Pharmaceutical Sciences, Department of Pharmaceutical Sciences, State University of New York, Amherst, NY, USA. Biochemical Pharmacology (2005), 70(4), 627-639. Publisher: Elsevier B.V., CODEN: BCPCA6 ISSN: 0006-2952. Journal written in English. CAN 143:205788 AN 2005:622949 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Anthocyanins are red, purple, or blue plant pigments that belong to the family of polyphenolic compds. collectively called flavonoids. Their demonstrated antioxidant properties and economic importance to the dye, fruit, and cut-flower industries have driven intensive research into their metabolic biosynthetic pathways. In order to produce stable, glycosylated anthocyanins from colorless flavanones such as naringenin and eriodictyol, a four-step metabolic pathway was constructed that contained plant genes from heterologous origins: flavanone 3β-hydroxylase from Malus domestica, dihydroflavonol 4-reductase from Anthurium andraeanum, anthocyanidin synthase (ANS) also from M. domestica, and UDP-glucose:flavonoid 3-O-glucosyltransferase from Petunia hybrida. Using two rounds of PCR, each one of the four genes was first placed under the control of the trc promoter and its own bacterial ribosome-binding site and then cloned sequentially into vector pK184. Escherichia coli cells contg. the recombinant plant pathway were able to take up either naringenin or eriodictyol and convert it to the corresponding glycosylated anthocyanin, pelargonidin 3-O-glucoside or cyanidin 3-O-glucoside. The produced anthocyanins were present at low concns., while most of the metabolites detected corresponded to their dihydroflavonol precursors, as well as the corresponding flavonols. The presence of side product flavonols is at least partly due to an alternate reaction catalyzed by ANS. This is the first time plant-specific anthocyanins have been produced from a microorganism and opens up the possibility of further prodn. improvement by protein and pathway engineering.

Abstract

Metabolic engineering of anthocyanin biosynthesis in Escherichia coli. Yan, Yajun; Chemler, Joseph; Huang, Lixuan; Martens, Stefan; Koffas, Mattheos A. G. Department of Chemical and Biological Engineering, University at Buffalo, The State University of New York, Buffalo, NY, USA. Applied and Environmental Microbiology (2005), 71(7), 3617-3623. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 143:284773 AN 2005:628645 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This work had as objective analyzes the antioxidant activity of aq. and alc. exts. obtained from of the Schinus terebenthifolius Raddi fruits or aroeira-vermelha, directly linked to the amt. of phenolics compds. existent in these exts. The aroeira fruits present an intermediate quantity of phenolics compds.: inferior to fruits, however superior to grains, being of 88 g to catequine/g of sample dry base for the ext. obtained by the extn. in hot water (aq. ext.) and 685 g of catequine/g of sample dry base for the ext. obtained by the extn. with abs. ethanol (alc. ext.). The alc. ext. was shown with the presence of the flavone apigenin, besides elagic acid, while in the aq. ext. was obsd. the flavanone naringine. As for its antioxidant power, it can be concluded that the antioxidant powers of both exts. are good, when it is compared to the antioxidant powers of the commonly used BHT (butylated hydroxytoluene) and BHA (butylated hydroxyanisole), because it is vegetable exts., whose antioxidant power is, in general, weaker than the artificial antioxidants. In the case of the alc. ext., the same presented a power antioxidant four times smaller than BHT and BHA. The aq. ext. for its time, presented a power antioxidant six times smaller than BHT and BHA.


flavanone

Studies on the synthesis of flavonoids by a two component reaction using microwave heating. Seijas, Julio A.; Vazquez-Tato, M. Pilar; Carballido-Reboredo, Raquel. Departamento de Quimica Organica, Facultad de Ciencias, Universidad de Santiago de Compostela, Lugo, Spain. Editor(s): Seijas, Julio A. International Electronic Conferences on Synthetic Organic Chemistry, 5th, 6th, Sept. 1-30, 2001 and 2002 [and] 7th, 8th, Nov. 1-30, 2003 and 2004 (2004), 1017-1019. Publisher: Molecular Diversity Preservation International, Basel, Switz CODEN: 69GTCO Conference; Computer Optical Disk written in English. CAN 143:440119 AN 2005:618345 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention relates to prepn. of gene chip using biotin labeled probes of tea tree flavanone 3-hydroxylase cDNA fragments and uses thereof. Specifically, the invention provides the sequence of tea tree flavanone 3-hydroxylase cDNA, and probes with 8-100 continuous nucleotides of the sequence. The invention can be used in evaluation of crop seed sources, early prediction of hybrid vigor, research on plant disease resistance, detn. of plant SNP, inspection of transgenic crop security, and screen of herbicides, etc.


Preparation of gene chips using biotin labelled probes of tea tree flavanone 3-hydroxylase cDNA fragments and uses thereof. Zhao, Liping; Chen, Liang; Gao, Qikang. (Tea Inst., Chinese Agricultural Academy, Peop. Rep. China). Faming Zhuanli Shenqing Gongkai Shuomingshu (2004), No pp. given. CODEN: CNXXEV CN 1552899 A 20041208 Patent written in Chinese. Application: CN 1010-9523 20031218. Priority: . CAN 143:223583 AN 2005:622229 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


and herbal products, have been shown to be BCRP inhibitors. The objective of the present study was to elucidate the SAR and derive a QSAR model for flavonoid-BCRP interaction. The EC50 values for increasing mitoxantrone accumulation in MCF-7 MX100 cells for 25 flavonoids, from five flavonoid subclasses, were detd. in this study or obtained from our previous publication [Zhang S, Yang X, Morris ME. Combined effects of multiple flavonoids on breast cancer resistance protein (ABCG2)-mediated transport. Pharm Res 2004;21(7):1263-73], and ranged from 0.07±0.02 μM to 183±21.7 μM. We found that the presence of a 2,3-double bond in ring C, ring B attached at position 2, hydroxylation at position 5, lack of hydroxylation at position 3 and hydrophobic substitution at positions 6, 7, 8 or 4', are important structural properties important for potent flavonoid-BCRP interaction. These structural requirements are similar but not identical to those for potent flavonoid-NBD2 (P-glycoprotein) interaction, indicating that inhibition of BCRP by flavonoids may involve, in part, the binding of flavonoids with the NBD of BCRP. In addn., a QSAR model consisting three structural descriptors was constructed, and both internally and externally validated, suggesting the model could be used to quant. predict BCRP inhibition activity of flavonoids. These findings should be useful for predicting BCRP inhibition activity of other untested flavonoids and for guiding the synthesis of potent BCRP inhibitors for potential clin. application.


flavanone

O

O

R

R1

I

Aminopropylated silicas are prepd. as catalysts for cyclocondensation reactions of hydroxyacetophenones 5-R-2-HOC6H4COMe and 4-substituted benzaldehydes 4-R1C6H4CHO to yield flavanones I (R = H, Cl, MeO; R1 = H, Cl, MeO, O2N) ; the catalysts are characterized by N2 sorption, TGA, FTIR, and solid-state NMR measurements. The amt. of aminopropyltriethoxysilane (APTES) used in the prepn. influences the morphol. of the hybrid org.-inorg. catalysts; the use of ≤ 10 mol% APTES with tetra-Et orthosilicate (TEOS) and a prehydrolysis step yields mesoporous structures with narrower pore size distributions and larger surface areas and pore vols. than those prepd. without the TEOS prehydrolysis steps. The fraction of aminopropyl groups present in the catalysts and the width of the size distribution for the mesopores det. the effectiveness of the aminopropylated silicas as catalysts for cyclocondensation reactions. The selectivity of the cyclocondensation reactions for flavanones (vs. condensation reactions to give hydroxychalcones) is highest for solvent-free reactions. Benzaldehydes contg. electron-donating groups are more reactive than benzaldehydes contg. electron-withdrawing groups in condensations with 2'-hydroxyacetophenones but are less selective for flavanones over hydroxychalcones, contrary to previous results obtained over solid acid or base catalysts; electron-donating or electron-withdrawing groups on the hydroxyacetophenones component have little effect on conversions, while selectivities increase slightly when electron-donating substituents are present on the hydroxyacetophenones. A mechanism for the generation of I over aminopropylated silica is proposed; the key steps involve the generation of silica-bound imine intermediates.

Abstract

Catalytic applications of aminopropylated mesoporous silica prepared by a template-free route in flavanones synthesis. Wang, Xueguang; Tseng, Yao-Hung; Chan, Jerry C. C.; Cheng, Soofin. Department of Chemistry, National Taiwan University, Taipei, Taiwan. Journal of Catalysis (2005), 233(2), 266-275. Publisher: Elsevier, CODEN: JCTLA5 ISSN: 0021-9517. Journal written in English. CAN 143:286257 AN 2005:615177 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH O

OMe

I

Preliminary results on the synthesis of flavanone I without the addn. of a second mol. of aldehyde to the 3 position of the flavanone by a two component addn.-cyclization approach using microwave heating is reported.

Abstract


flavanone

The Arabidopsis transcription factor MYB12 is a flavonol-specific regulator of phenylpropanoid biosynthesis. Mehrtens, Frank; Kranz, Harald; Bednarek, Pawel; Weisshaar, Bernd. Max-Planck-Institute for Plant Breeding Research, Cologne, Germany. Plant Physiology (2005), 138(2), 1083-1096. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 143:245030 AN 2005:603026 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Different phytoestrogens were tested as inhibitors of 17β-hydroxysteroid dehydrogenase from the fungus Cochliobolus lunatus (17β-HSDcl), a member of the short-chain dehydrogenase/reductase superfamily. Phytoestrogens inhibited the oxidn. of 100 μM 17β-hydroxyestra-4-en-3-one and the redn. of 100 μM estra-4-en-3,17-dione, the best substrate pair known. The best inhibitors of oxidn., with IC50 below 1 μM, were flavones hydroxylated at positions 3, 5 and 7: 3-hydroxyflavone, 3,7-dihydroxyflavone, 5,7-dihydroxyflavone (chrysin) and 5-hydroxyflavone, together with 5-methoxyflavone. The best inhibitors of redn. were less potent; 3-hydroxyflavone, 5-methoxyflavone, coumestrol, 3,5,7,4'-tetrahydroxyflavone (kaempferol) and 5-hydroxyflavone all had IC50 values between 1 and 5 μM. Docking the representative inhibitors chrysin and kaempferol into the active site of 17β-HSDcl revealed the possible binding mode, in which they are sandwiched between the nicotinamide moiety and Tyr212. The structural features of phytoestrogens, inhibitors of both oxidn. and redn. catalyzed by the fungal 17β-HSD, are similar to the reported structural features of phytoestrogen inhibitors of human 17β-HSD types 1 and 2.

Abstract

Phytoestrogens as inhibitors of fungal 17β-hydroxysteroid dehydrogenase. Kristan, Katja; Krajnc, Katja; Konc, Janez; Gobec, Stanislav; Stojan, Jure; Rizner, Tea Lanisnik. Institute of Biochemistry, Medical Faculty, University of Ljubljana, Ljubljana, Slovenia. Steroids (2005), 70(10), 694-703. Publisher: Elsevier B.V., CODEN: STEDAM ISSN: 0039-128X. Journal written in English. CAN 143:318347 AN 2005:610446 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


3-Acylchromones and 3-acylflavones, readily available by acylation of 2'-hydroxydibenzoylmethane with acid anhydrides in the presence of base, undergo efficient conjugate redn. with NaBH4 in pyridine to give the corresponding chroman-4-ones/flavanones in high yields. The redn. is both regio- and chemoselective. Treatment of the chroman-4-ones with MeSO3H generates the 3-alkenyl-2-arylchromones by a dehydrative rearrangement initiated by retro-Michael cleavage of the pyranone ring. This redn.-rearrangement sequence can be extended to 2-alkyl-3-alkenoylchromones to generate 3-alkenyl-2-styrylchromones, the first examples of 2,3-dialkenylchromones.

Abstract

Synthesis of 3-alkenyl-2-arylchromones and 2,3-dialkenylchromones via acid-catalysed retro-Michael ring opening of 3-acylchroman-4-ones. Clarke, David S.; Gabbutt, Christopher D.; Hepworth, John D.; Heron, B. Mark. Department of Colour and Polymer Chemistry, University of Leeds, Leeds, UK. Tetrahedron Letters (2005), 46(33), 5515-5519. Publisher: Elsevier B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN 143:286191 AN 2005:614691 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Five unusual C-methylflavonoids lacking B-ring oxygenation (2',4'-dihydroxy-3',5'-dimethyl-6'-methoxychalcone, 2',4'-dihydroxy-3'-methyl-6'-methoxychalcone, 2',6'-dihydroxy-3'-methyl-4'-methoxychalcone, 2'-hydroxy-3'-methyl-4',6'-dimethoxychalcone and 5,7-dihydroxy-6,8-dimethylflavanone) were found for the first time in Metrosideros excelsa. The flavanone was the major constituent in leaves, whereas 2',6'-dihydroxy-3'-methyl-4'-methoxychalcone dominated all other aerial plant parts studied. Other Metrosideros species were investigated for these five flavonoids. C19-C36 aldehydes and C22-C32 alcs. were also identified from the dried seed capsules of M. excelsa.

Abstract

Lipophilic C-methylflavonoids with no B-ring oxygenation in Metrosideros species (Myrtaceae). Mustafa, Kamarul'Ain; Perry, Nigel B.; Weavers, Rex T. Department of Chemistry, University of Otago, Dunedin, N. Z. Biochemical Systematics and Ecology (2005), 33(10), 1049-1059. Publisher: Elsevier B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 144:19604 AN 2005:593203 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


2',4'-Dihydroxy-3',5'-dimethyl-6'-methoxychalcone (1), its isomeric flavanone 5-O-methyl-4'-desmethoxymatteucinol (2) and 2'4'-dihydroxy-6'-methoxy-3'-methylchalcone (3) were isolated from the leaves of S. samarangense using a bioassay-directed scheme. In an oral glucose tolerance test, at a dosage of 1.0 mg/20 g mouse, 1 and 2 significantly (α = 0.05) lowered the blood glucose levels (BGLs) in glucose-hyperglycemic mice when administered 15 min after a glucose load. When co-administered with glucose, only 1 showed a significant lowering of BGLs 45 min after its oral administration. When administered 15 min before glucose, none of the flavonoids showed a pos. effect. Only 1 decreased significantly, at α = 0.05, the BGLs of alloxan-diabetic mice at t = 90-150 min.

Abstract

Antihyperglycaemic flavonoids from syzygium samarangense (Blume) Merr. and Perry. Resurreccion-Magno, Ma. Hanshella C.; Villasenor, Irene M.; Harada, Nobuyuki; Monde, Kenji. Institute of Chemistry, University of the Philippines, Quezon City, Philippines. Phytotherapy Research (2005), 19(3), 246-253. Publisher: John Wiley & Sons Ltd., CODEN: PHYREH ISSN: 0951-418X. Journal written in English. CAN 144:337673 AN 2005:596713 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Comprehensive functional data on plant R2R3-MYB transcription factors is still scarce compared to the manifold of their occurrence. Here, we identified the Arabidopsis thaliana R2R3-MYB transcription factor MYB12 as a flavonol-specific activator of flavonoid biosynthesis. Transient expression in Arabidopsis protoplasts revealed a high degree of functional similarity between MYB12 and the structurally closely related factor P from maize (Zea mays). Both displayed similar target gene specificity, and both activated target gene promoters only in the presence of a functional MYB recognition element. The genes encoding the flavonoid biosynthesis enzymes chalcone synthase, chalcone flavanone isomerase, flavanone 3-hydroxylase, and flavonol synthase were identified as target genes. Hence, our observations further add to the general notion of a close relationship between structure and function of R2R3-MYB factors. High-performance liq. chromatog. analyses of myb12 mutant plants and MYB12 overexpression plants demonstrate a tight linkage between the expression level of functional MYB12 and the flavonol content of young seedlings. Quant. real time reverse transcription-PCR using these mutant plants showed MYB12 to be a transcriptional regulator of CHALCONE SYNTHASE and FLAVONOL SYNTHASE in planta, the gene products of which are indispensable for the biosynthesis of flavonols.

Abstract


flavanone

Abstract

Radical scavenging activity of various extracts and fractions of sweet orange peel (Citrus sinensis). Anagnostopoulou, Maria A.; Kefalas, Panagiotis; Papageorgiou, Vassilios P.; Assimopoulou, Andreana N.; Boskou, Dimitrios. Department of Chemical Engineering, Faculty of Engineering, Aristotle University of Thessaloniki, Thessaloniki, Greece. Food Chemistry (2005), Volume Date 2006, 94(1), 19-25. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 143:325212 AN 2005:589826 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Capillary electrochromatog. using cyclodextrins modified with dichloro-, dimethyl-, and chloromethylcarbamate groups were used for the enantiomeric sepn. of std. analytes. The chiral selector was chem. bonded to aminopropylsilanized silica particles, and these chiral stationary phases (CSPs), mixed with aminopropylsilanized silica (1:1 wt.:wt.), were packed into 100-μm-internal diam. fused-silica capillaries. The effect of the type of cyclodextrin, the nature and position of the substituents on the Ph ring, and the binding mode of cyclodextrin phenyl-carbamates onto the silica gel surface on the chiral recognition were studied. Exptl. parameters such as org. solvent concn. were varied to better understand the mechanism contributing to the chiral recognition of these CSPs. Good enantiosepns. were achieved for a racemic flavanone (FLA) and trans-cyclopropanedicarboxylic acid dianilide (CAD).

Abstract

Evaluation of cyclodextrins modified with dichloro-, dimethyl-, and chloromethylphenylcarbamate groups as chiral stationary phases for capillary electrochromatography. Kartozia, Irma; D'Orazio, Giovanni; Chankvetadze, Bezhan; Fanali, Salvatore. Instituto di Metodologie Chimiche, Consiglio Nazionale delle Ricerche, Area della Ricerca di Roma, Rome, Italy. Journal of Capillary Electrophoresis and Microchip Technology (2005), 9(3/4), 31-38. Publisher: ISC Technical Publications, Inc., CODEN: JCEMF6 Journal written in English. CAN 144:266139 AN 2005:590801 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Several citrus limonoid glycosides have proved to be particularly difficult to purify using conventional techniques. A reversed-phase flash chromatog. technique was developed for the sepn. and isolation of the closely related limonoid glucosides, nomilin 17-β-D-glucopyranoside and nomilinic acid 17-β-D-glucopyranoside, with confirmation of their identities by electrospray ionization mass spectrometry. Furthermore, the semi-purifn. of the mixt. of glucosides enriched with flavanone glucosides such as naringin, narirutin and other limonoid glucosides was obtained. The closely eluting glucosides were successfully sepd. to achieve a good yield and purity of 93%.

Abstract

Isolation and purification of closely related Citrus limonoid glucosides by flash chromatography. Raman, Girija; Cho, Minhee; Brodbelt, Jennifer S.; Patil, Bhimanagouda S. Kingsville Citrus Center, Texas A and M University, Weslaco, TX, USA. Phytochemical Analysis (2005), 16(3), 155-160. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal written in English. CAN 144:57044 AN 2005:591101 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


Polynucleotides encoding polypeptides active in lignin, fructan and tannin biosynthetic pathways are provided from Lolium perenne (perennial ryegrass) and Festuca arundinaceae (tall fescue), together with expression vectors and host cells comprising such isolated polynucleotides. The polynucleotides were taken at different times of the year, specifically in winter and spring, and from different parts of the the plants, including leaf blades, leaf base, pseudostems, floral stems, roots, inflorescences, and stems. Methods for the use of such polynucleotides and polypeptides are also provided.

Abstract US 2004-563879P P 20040420US 2003-507991P P 20031002US 2002-289757 A2 20021107US 2001-337703P P 20011107Priority Application US 20070204363 A1 20070830 US 2006-560738 20061116 US 7154027 B2 20061226US 20030180751 A1 20030925 US 2002-289757 20021107US 20050150008 A1 20050707 US 2004-955745 20040930Patent No. Kind Date Application No. Date Patent Family Information

Nucleic acids and encoded enzymes active in lignin, fructan and tannin biosynthesis from forage grasses. Demmer, Jeroen; Forster, Richard L.; Shenk, Michael Andrew; Norriss, Michael Geoffrey; Glenn, Matthew; Saulsbury, Keith Martin; Hall, Claire. (Agrigenesis Biosciences Ltd., N. Z.; Wrightson Seeds Ltd.). U.S. Pat. Appl. Publ. (2005), 38 pp., Cont.-in-part of U.S. Ser. No. 289,757. CODEN: USXXCO US 2005150008 A1 20050707 Patent written in English. Application: US 2004-955745 20040930. Priority: US 2001-337703 20011107; US 2002-289757 20021107; US 2003-507991 20031002; US 2004-563879 20040420. CAN 143:72806 AN 2005:588436 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Seven different exts., fractions and residues of Navel sweet orange (Citrus sinensis) peel were evaluated for their radical scavenging activity by the DPPH⋅ and luminol induced chemiluminescence methods. Also, the Folin-Ciocalteu method was used to det. the total phenolic content. High phenolic content and radical scavenging activities were found for the Et acetate fraction. Comparison was made with ref. compds., Trolox, ascorbic acid, quercetin, which are already known for their good antioxidant activity. The radical scavenging activity of the Et acetate fraction approached the activity of the stds. Total phenolic content showed a small relation with radical scavenging activity. The radical scavenging activity examd. with the DPPH method correlated well to values obtained by chemiluminescence. The antioxidant activity found in the fractions of Citrus sinensis, should be attributed to the presence of flavonoids and other phenolic compds. Among the various classes of flavonoids: flavanone glycosides, flavones and flavonols seem to prevail as indicated by two dimensional thin layer chromatog. and color reactions. This information shows that Et acetate fraction of navel sweet orange peel can be used as antioxidant in food and medicinal prepns.


flavanone

Method of breeding plants with yellow flowers by regulating flavonoid biosynthesis system. Tanaka, Yoshikazu; Ono, Eiichiro; Nakamura, Noriko; Mizutani, Masako. (Suntory Limited, Japan; Suntory Flowers Limited). PCT Int. Appl. (2005), 95 pp. CODEN: PIXXD2 WO 2005059141 A1 20050630 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU,


Flavanone 3-hydroxylase (F3H) is a key enzyme in the flavonoid biosynthetic pathway, providing a branching point for the biosynthesis of different flavonoids, including the formation of 3-deoxy and 3-hydroxy flavonoids found in the silks of maize. Here, we report the cloning and characterization of a F3H gene (Smf3h) from a cDNA library derived from a red line callus of Saussurea medusa, a traditional Chinese medicinal plant. The cDNA contains a 1032 bp open reading frame (ORF) encoding a protein of 343 amino acid residues, a 149 bp long 5'untranslated regions (UTR) and a 163 bp long 3'UTR contg. three putative polyadenylation signals (AATAAA) and an ATTTA element. The secondary structure of the mRNA predicted by MFOLD is very complex, suggesting a role in a post-transcriptional mechanism of regulation of Smf3h. The genomic structure of Smf3h includes four exons and three introns within the coding region, with all the splice donor/acceptor site sequences in accordance with the "GU-AG" consensus rule. The deduced SmF3H protein is 343 amino acid residues in length and has 40% and 39% identity and 60% and 58% similarity to the F3H of Arabidopsis and rice, resp. Strikingly, the identity of SmF3H is higher to the H6H (hyoscyamine 3β-hydroxylase, 45%) from Atropa belladonna. However, the anal. of the active center and the predicted protein secondary structure are more related to F3H than H6H. Together, our studies provide the first identification of a S. medusa flavonoid gene and its similarities to metabolic enzymes from other plants.

Abstract

Cloning and characterization of a flavanone 3-hydroxylase gene from Saussurea medusa. Jin, Zhiping; Grotewold, Erich; Qu, Wenquan; Fu, Ghunxiang; Zhao, Dexiu. Institute of Botany, Chinese Academy of Sciences, Beijing, Peop. Rep. China. DNA Sequence (2005), 16(2), 121-129. Publisher: Taylor & Francis Ltd., CODEN: DNSEES ISSN: 1042-5179. Journal written in English. CAN 143:261149 AN 2005:565597 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A facile efficient, and preparative approach for monohydroxyflavanone syntheses was described. Using this protocol, a hydroxyl is regio-selectively introduced at one carbon of a flavanone A- or B-ring per synthesis. The seven possible isomers were each synthesized from the corresponding monomethoxymethoxylated 2'-hydroxychalcones in acidic soln. These monohydroxyflavanones were characterized using a gas chromatog.-mass spectrometry (GC-MS) system that incorporated a DB-5 capillary column. This is the first report of a preparative synthetic method during which a single hydroxyl can be selectively added to a flavanone A- or B-ring at any position. A procedure that separates the seven isomers by GC and characterizes the mass spectra of the isomers was developed. Both the synthetic method and the GC-MS conditions may become important tools during future flavanone metab. and oxidn. studies.

Abstract

Preparative monohydroxyflavanone syntheses and a protocol for gas chromatography-mass spectrometry analysis of monohydroxyflavanones. Kagawa, Hitoshi; Shigematsu, Asako; Ohta, Shigeru; Harigaya, Yoshihiro. Department of Organic Synthesis, School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan. Chemical & Pharmaceutical Bulletin (2005), 53(5), 547-554. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 143:248178 AN 2005:581192 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Chemical shifts of 1H and 13C in 5-H-flavanone and 5-H-flavonol isolated from Leguminosae. Alves do Nascimento, Ildomar; Gomes, Mario Sergio da Rocha; Geraldo de Carvalho, Mario; Geraldo de Carvalho, Acacio. Doutorando do PPGQO do Departmento de Quimica, Instituto de Ciencias Exatas, Universidade Federal Rural do Rio de Janeiro, Seropedica, Rio de Janeiro, Brazil. Revista Universidade Rural, Serie Ciencias Exatas e da Terra (2003), 22(1-2), 81-87. Publisher: Editora da Universidade Federal Rural do Rio de Janeiro, CODEN: RURSAQ ISSN: 1414-0578. Journal written in Portuguese. CAN 144:229262 AN 2005:551356


A method of breeding the plants with yellow flowers by regulating flavonoid biosynthesis system has been developed. The regulation process includes the introduction of the vector contg. the transgene encoding the enzyme that transfers sugars to 4'-position of chalcones into host plant cells. The glycosyltransferase genes are cloned from Antirrhinum majus or Linaria bipartita in Scrophulariaceae. The transformant cells, the purifn. method of the expressed transferase, whole transgenic plants and their tissues, descendants and cut flowers are claimed. The process also includes the co-expressing of the gene for aureusidin synthase and dsRNA-induced silencing of the genes for dihydroflavonol reductase and/or flavanone 3-hydroxlase to promote the coloring the flowers in yellow. By the claimed method to manipulate the flavonoid biosynthesis system, a transgenic plant with flowers in an improved vivid yellow color can be obtained. Flower color change by the claimed method was tested in Torenia fournieri.

Abstract WO 2004-JP19461 W 20041217JP 2003-420046 A 20031217Priority Application US 20080009032 A1 20080110 US 2006-583110 20060615

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, FI, RO, CY, TR, BG, CZ, EE, HU, PL, SK, IS





SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IS, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2004-JP19461 20041217. Priority: JP 2003-420046 20031217. CAN 143:92063 AN 2005:564757 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 605:

Products made from Herba Santa (Eriodictyon californicum (H. & A.) Torr.) have been used as bitter remedies for some pharmaceutical applications for many years, but they are actually too arom. to be useful for many food or pharmaceutical applications. In sensory studies flavanones homoeriodictyol (1), its sodium salt (1-Na), sterubin (2), and eriodictyol (4) could significantly decrease the bitter taste of caffeine without exhibiting intrinsic strong flavors or taste characteristics. Further investigations on 1-Na elicited a broad masking activity between 10 and 40% toward different chem. classes of bitter mols. (e.g. salicin, amarogentin, paracetamol, quinine) but not toward bitter linoleic acid emulsions. For caffeine and amarogentin, dose-response studies were performed; the masking activity toward bitter taste for both compds. reached a plateau at higher concns. of 1-Na. Due to these facts, homoeriodictyol sodium salt (1-Na) seems to be a very interesting new taste modifier for food applications and pharmaceuticals.

Abstract

Evaluation of Bitter Masking Flavanones from Herba Santa (Eriodictyon californicum (H. & A.) Torr., Hydrophyllaceae). Ley, Jakob P.; Krammer, Gerhard; Reinders, Gerald; Gatfield, Ian L.; Bertram, Heinz-Juergen. Research and Development, Symrise GmbH & Company KG, Holzminden, Germany. Journal of Agricultural and Food Chemistry (2005), 53(15), 6061-6066. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:210692 AN 2005:535269 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Activity-guided isolation of antifungal, antibacterial, and antioxidant compds. from the dichloromethane ext. of the aerial parts of Eriophorum scheuchzeri led to the isolation of eight flavonoids. Three isoflavones and one flavanone are new natural compds. The isolation of the bioactive compds. was performed by centrifugal partition chromatog. Fractions and pure compds. were monitored by a direct TLC bioautog. assay. Their structures were elucidated by spectroscopic and chem. methods.

Abstract

Flavonoids from the Stem of Eriophorum scheuchzeri. Maver, Milena; Queiroz, Emerson F.; Wolfender, Jean-Luc; Hostettmann, Kurt. Laboratoire de Pharmacognosie et Phytochimie, Section de Sciences Pharmaceutiques, University of Geneva, Geneva, Switz. Journal of Natural Products (2005), 68(7), 1094-1098. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 143:225993 AN 2005:543701 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Unambiguous 1H and 13C chem. shift assignments in NMR spectra of 3,4',7-trihydroxyflavonone (garbanzol) isolated from Schizolobium parahyba and 3',4',7,8-tetrahydroxyflavanone isolated from Piptadenia rigida were studied using 1D and 2D NMR spectroscopic techniques.

Abstract CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

One new flavanone, 4'-hydroxyisorottlerin (I), and two new chalcone derivs., kamalachalcones C (II) and D (III), were isolated from Mallotus philippensis (kamala tree). The largest compd. (kamalachalcone D; Mr 1098 g/mol) was shown to possess a unique, fused-ring system made of two hydroxy-chalcone units, giving rise to eight fused benzene/pyran units. From the same plant, the following six known compds. were also isolated: kamalachalcone A and B, isoallorottlerin, isorottlerin, 5,7-dihydroxy-8-methyl-6-prenylflavanone, 6,6-dimethylpyrano(2'',3'':7,6)-5-hydroxy-8-methylflavanone, and rottlerin. The structures of the new compds. were confirmed by in-depth spectral analyses, including 2D-NMR techniques, and the full 13C-NMR assignments of rottlerin, isoallorottlerin, isorottlerin, 5,7-dihydroxy-8-methyl-6-prenylflavanone, and 6,6-dimethylpyrano(2'',3'':7,6)-5-hydroxy-8-methylflavanone are published for the first time.

Abstract

Novel, complex flavonoids from Mallotus philippensis (Kamala tree). Furusawa, Miyuki; Ido, Yoshimi; Tanaka, Toshiyuki; Ito, Tetsuro; Nakaya, Ken-ichi; Ibrahim, Iliya; Ohyama, Masayoshi; Iinuma, Munekazu; Shirataka, Yoshiaki; Takahashi, Yoshikazu. Gifu Prefectural Institute of Health and Environmental Sciences, Kakamigahara, Japan. Helvetica Chimica Acta (2005), 88(5), 1048-1058. Publisher: Verlag Helvetica Chimica Acta, CODEN: HCACAV ISSN: 0018-019X. Journal written in English. CAN 143:208933 AN 2005:527847 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

O OMe

Me

OOH

OH

HO

Me

HO

Me O

OH

O

O

O

HO

OH

Me

Me

MeH

HOH

OH

MeMe

O

HO O

OO

O

Me Me

OH

OHHO

Me

Me

O

Me Me

OHO

MeO

O

Me Me

OHHO

Me

O

I

III

II


flavanone


The extrahepatic human UDP glucuronosyltransferase 1A10 is found throughout the gastrointestinal tract and is thought to participate in the removal of orally ingested lipophilic chems. However, its substrate specificity towards these chems. has not been fully characterized. The structurally diverse bioflavonoids are present in considerable amts. in fruits, vegetables and plant-derived beverages and have been shown to have many biol. functions, including antioxidant properties. This study proposes features of the bioflavonoid structure necessary to confer it as a substrate of UGT1A10. The preferred substrates of UGT1A10 contain the hydroxyl group to be glucuronidated at C6 or C7, but not C5 of the A-ring or on C4' of the B-ring. Up to two addnl. hydroxyl groups on the A-ring enhance activity, whereas the presence of other groups, notably sugar groups, decreases activity. The high glucuronidation efficiency towards many bioflavonoids obsd. suggests that the contribution of UGT1A10 in the metab. of these dietary compds. in the gastrointestinal tract may be significant.

Abstract

Glucuronidation of bioflavonoids by human UGT1A10: Structure-function relationships. Lewinsky, R. H.; Smith, P. A.; Mackenzie, P. I. Department of Clinical Pharmacology, Flinders Medical Centre, Flinders University School of Medicine, Bedford Park, Australia. Xenobiotica (2005), 35(2), 117-129. Publisher: Taylor & Francis Ltd., CODEN: XENOBH ISSN: 0049-8254. Journal written in English. CAN 144:186917 AN 2005:517717 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Plant species of the family Apiaceae are known to accumulate flavonoids mainly in the form of flavones and flavonols. Three 2-oxoglutarate-dependent dioxygenases, flavone synthase or flavanone 3 β-hydroxylase and flavonol synthase are involved in the biosynthesis of these secondary metabolites. The corresponding genes were cloned recently from parsley (Petroselinum crispum) leaves. Flavone synthase I appears to be confined to the Apiaceae, and the unique occurrence as well as its high sequence similarity to flavanone 3β-hydroxylase laid the basis for evolutionary studies. In order to examine the relationship of these two enzymes throughout the Apiaceae, RT-PCR based cloning and functional identification of flavone synthases I or flavanone 3β-hydroxylases were accomplished from Ammi majus, Anethum graveolens, Apium graveolens, Pimpinella anisum, Conium maculatum and Daucus carota, yielding three addnl. synthase and three addnl. hydroxylase cDNAs. Mol. and phylogenetic analyses of these sequences were compatible with the phylogeny based on morphol. characteristics and suggested that flavone synthase I most likely resulted from gene duplication of flavanone 3β-hydroxylase, and functional diversification at some point during the development of the apiaceae subfamilies. Furthermore, the genomic sequences from Petroselinum crispum and Daucus carota revealed two introns in each of the synthases and a lack of introns in the hydroxylases. These results might be explained by intron losses from the hydroxylases occurring at a later stage of evolution.

Abstract

Molecular evolution of flavonoid dioxygenases in the family Apiaceae. Gebhardt, Yvonne; Witte, Simone; Forkmann, Gert; Lukacin, Richard; Matern, Ulrich; Martens, Stefan. Institut fuer Pharmazeutische Biologie, Philipps Universitaet Marburg, Marburg/Lahn, Germany. Phytochemistry (Elsevier) (2005), 66(11), 1273-1284. Publisher: Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 143:209041 AN 2005:525700 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Analysis of flavanone-7-O-glycosides in citrus juices by short-end capillary electrochromatography. Desiderio, Claudia; De Rossi, Antonella; Sinibaldi, Massimo. Istituto di Metodologie Chimiche, CNR, Rome, Italy. Journal of Chromatography, A (2005), 1081(1), 99-104. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 143:171510 AN 2005:513173 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Hesperetin (5,7,3'-trihydroxyl-4'-methoxyl-flavanone) is an important bioactive compd. in Chinese traditional medicine and has multiple biol. and pharmacol. activities. The interaction of hesperetin with human serum albumin (HSA) has been investigated by UV absorption, fluorescence and Fourier transformed IR spectrometry. Fluorescence results showed that one mol. of protein combined with one mol. of drug at the molar ratio of drug to HSA ranging from 0.3 to 7 and the binding affinity (KA) was 8.11×104 M-1. The primary binding site was most likely located on subdomain IIA. The binding ability of the drug to protein decreased from pH 6.4 to 8.4 in the drug to protein molar ratio of 1. Combining the curve-fitting results of IR amide I band in D2O and H2O phosphate buffers, the alterations of protein secondary structure after drug complexation were estd. With increasing the drug concn., the percentage of protein α-helix structure decreased gradually. The redn. of protein α-helix structure reached about 7-9% after the protein interacted with hesperetin in D2O and H2O buffer soln. at pH 7.4 when the drug to protein molar ratio was 10. This indicated a partial unfolding of HSA in the presence of the drug. From the results of UV absorption, fluorescence and Fourier transformed IR spectrometry, the binding mode was discussed. The main mechanism of protein fluorescence quenching was a static quenching process and the hydroxyl groups of the drug in its neutral part played an important role in the binding process.

Abstract

Interaction between hesperetin and human serum albumin revealed by spectroscopic methods. Xie, Meng-Xia; Xu, Xiao-Yun; Wang, Ying-Dian. Analytical & Testing Center, Beijing Normal University, Beijing, Peop. Rep. China. Biochimica et Biophysica Acta, General Subjects (2005), 1724(1-2), 215-224. Publisher: Elsevier B.V., CODEN: BBGSB3 ISSN: 0304-4165. Journal written in English. CAN 143:90946 AN 2005:515120 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Liq. phase Claisen-Schmidt condensation between 2'-hydroxyacetophenone and benzaldehyde to form 2'-hydroxychalcone, followed by intramol. cyclization to form flavanone was carried out over zinc oxide-supported metal oxide catalysts under solvent free condition. The reaction was carried out over ZnO-supported MgO, BaO, K2O and Na2O catalysts with 0.2 g of each catalyst at 140° for 3 h. ZnO-supported MgO was obsd. to offer highest conversion of 2'-hydroxyacetophenone than other catalysts. Other supports, such as HZSM-5, Al2O3 and SiO2, impregnated with MgO were also used for the reaction to assess the suitability of the support. The order of activity of the catalyst support is ZnO > SiO2 > Al2O3 > HZSM-5. Various wt. percentage of MgO was loaded on ZnO to optimize max. efficiency of the catalyst system. The impregnation of MgO (wt%) in ZnO was optimized for better conversion of 2'-hydroxyacetophenone. The effect of temp. and catalyst loading was studied for the reaction.

Abstract

Solvent free synthesis of chalcone and flavanone over zinc oxide supported metal oxide catalysts. Saravanamurugan, S.; Palanichamy, M.; Arabindoo, Banumathi; Murugesan, V. Department of Chemistry, Anna University, Chennai, India. Catalysis Communications (2005), 6(6), 399-403. Publisher: Elsevier B.V., CODEN: CCAOAC ISSN: 1566-7367. Journal written in English. CAN 144:253971 AN 2005:515821 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 613:

Flavonoids, a group of low mol. wt. phenylbenzopyrones, have various pharmacol. properties including antioxidant activity, anticancer, and immunomodulatory effects. In the present study, lipopolysaccharide (LPS) and phorbol 12-myristate 13-acetate/phytohemagglutinin (PMA/PHA) were used as stimulants for RAW 264.7 macrophages and human peripheral blood mononuclear cell (hPBMC), and tumor necrosis factor (TNF)-α and interleukin (IL)-2 productions were measured. In addn., flavonoids were examd. for their effects on LPS-induced NO prodn. in RAW 264.7 macrophages. The results showed that all compds. were not strongly cytotoxic at the tested concns. on hPBMC and RAW 264.7 macrophages. On immunomodulatory properties, catechin, epigallocatechin (EGC), naringenin, and fisetin repressed NO prodn. and TNF-α secretion. Furthermore, catechin, epigallocatechin gallate (EGCG), epicatechin (EC), luteolin, chrysin, quercetin, and galangin increased IL-2 secretion while EGC, apigenin, and fisetin inhibited the secretion. These results indicated that flavonoids have the capacity to modulate the immune response and have a potential anti-inflammatory activity. There was no obvious structure-activity relationship regard to the chem. compn. of the flavonoids and their cell biol. effects.

Abstract

Production of cytokine and NO by RAW 264.7 macrophages and PBMC in vitro incubation with flavonoids. Lyu, Su-Yun; Park, Won-Bong. Immune Modulation Research Laboratory, School of Pharmacy, University of Nottingham, Nottingham, UK. Archives of Pharmacal Research (2005), 28(5), 573-581. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 143:206004 AN 2005:502567 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Eleven constituents, 7-hydroxy-2,5-dimethylchromone (1), (-)-farrerol (2), (±)-4-hydroxy-4,7-dimethyl-α-tetralone (3), six ferulic acid esters (4-9), eudesm-4 (15)-ene-1β,6α-diol (10) and opposit-4(15)-ene-1β,11-diol (11) were isolated from Hypericum erectum Thunb. Their structures were established on the basis of spectral data. In addn., (±)-3 was sepd. into its enantiomers [(+)-3, (-)-3], and the abs. configurations at C-4 of (+)-3 and (-)-3 were assigned as S and R, resp., from the CD (CD) spectral data.

Abstract

Studies on the constituents of Hypericum species. I. on the chemical constituents of Hypericum erectum Thunb. Matsuoka, Erika; Machida, Koichi; Kikuchi, Masao. Fac. Pharm. Sci., Tohoku Pharm. Univ., Japan. Journal of Tohoku Pharmaceutical University (2004), 51 41-48. Publisher: Tohoku Yakka Daigaku, CODEN: JTPUFY ISSN: 1345-157X. Journal written in Japanese. CAN 143:189890 AN 2005:503827 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The sepn. of the major flavanone-7-O-glycoside constituents of Citrus was carried out by isocratic reversed phase capillary electrochromatog. using a 75 μm i.d. silica fused column packed with 5 μm ODS silica gel. In comparison to HPLC mode, capillary electrochromatog. resoln. of flavanone glycosides was obtained with a high selectivity factor. Optimum sepn. conditions were found using a mixt. of ammonium formate (pH 2.5)-acetonitrile (8:2, vol./vol.) as the mobile phase by the short-end injection mode. Under these conditions all the investigated flavanones were baseline-resolved within short anal. time (i.e. between 5 and 10 min). A study, evaluating the intra- and inter-day repeatability as well as limit of detection and method linearity, was developed in accordance with the anal. procedures for method validation. The developed method was applied for the quant. anal. of flavanone glycosides in com. fruit juices (sweet orange, lemon and grapefruit).


flavanone

Seven healthy women and six men consumed daily 256 mg vitamin C, 229 mg hesperidin (main flavonoid glycoside), 6 mg carotenoids (mainly luteins and cryptoxanthins), and 0.16 mg folate incorporated in 236 mL of not-from-conc. orange juice (OJ) added

Abstract

Bioavailability and antioxidant effects of orange juice components in humans. Franke, Adrian A.; Cooney, Robert V.; Henning, Susanne M.; Custer, Laurie J. Cancer Research Center of Hawaii, University of Hawaii, Honolulu, HI, USA. Journal of Agricultural and Food Chemistry (2005), 53(13), 5170-5178. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:132469 AN 2005:447848 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method for the oxidn. of flavanones to flavones was developed using [hydroxy(tosyloxy)iodo]benzene in the room-temp. ionic liq. 1,3-di-n-butylimidazolium bromide.

Abstract

Facile oxidation of flavanones to flavones using [hydroxy(tosyloxy)iodo]benzene in an ionic liquid. Muthukrishnan, Murugan; Patil, Pratap S.; More, Shivaji V.; Joshi, Ramesh A. Division of Organic Chemistry: Technology, National Chemical Laboratory, Pune, India. Mendeleev Communications (2005), (3), 100-101. Publisher: Russian Academy of Sciences, CODEN: MENCEX ISSN: 0959-9436. Journal written in English. CAN 144:150151 AN 2005:494772 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Activity-guided fractionation of the CH2Cl2-sol. fraction of the roots of Sophora flavescens furnished five 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavengers: trans-hexadecyl ferulic acid (1), cis-octadecyl ferulic acid (2), trans-hexadecyl sinapic acid (3), (-)-4-hydroxy-3-methoxy-(6aR,11aR)-8,9-methylenedioxypterocarpan (4) and desmethylanhydroicaritin (8), along with nine known inactive compds.: (-)-maackiain (5), xanthohumol (6), formononetin (7), (2S)-2'-methoxykurarinone (9), (2S)-3β,7,4'-trihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (10), (2S)-7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (11), umbelliferone (12), kuraridin (13), and trifolirhizin (14). Compds. 1-4 and 8 exhibited DPPH free radical scavenging effects at IC50 values of 33.01 ± 0.20, 57.06 ± 0.16, 39.84 ± 0.36, 35.83 ± 0.47, and 18.11 ± 0.04 μM, resp. L-Ascorbic acid, when used as a pos. control, exhibited an IC50 value of 7.39 ± 0.01 μM. Compds. 1-4 and 8 also appeared to exert significant scavenging effects on authentic ONOO-, with IC50 values of 5.76 ± 1.19, 15.06 ± 1.64, 8.17 ± 4.97, 1.95 ± 0.29, and 4.06 ± 2.41 μM, resp. Penicillamine (IC50 = 2.36 ± 0.79 μM) was used as a pos. control. In addn., compds. 2, 4, 6, 8, and 10 were isolated from this plant for the first time.

Abstract

In vitro free radical and ONOO- scavengers from Sophora flavescens. Jung, Hee Jin; Kang, San Sik; Hyun, Sook Kyung; Choi, Jae Sue. Faculty of Food Science and Biotechnology, Pukyong National University, Pusan, S. Korea. Archives of Pharmacal Research (2005), 28(5), 534-540. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 143:456113 AN 2005:502560 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 618:

In grape cultivation, high night temp. generally reduces anthocyanin accumulation in berry skin. To clarify the regulatory mechanism of anthocyanin biosynthesis under the conditions of high night temps., we examd. flavonoid accumulation, the activities of related enzymes and gene expression in the anthocyanin biosynthetic pathway in grape berries grown under cool and warm night conditions. Anthocyanin accumulation in the skin of berries grown at high night temps. (30 °C continuous) was reduced as compared to that of berries grown at low night temps. (30 °C in daytime/15 °C in night time). On the other hand, flavonol levels in the skin of berries were not significantly different between low and high night temp. conditions. High night temps. also inhibited the gene expression of chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), leucoanthocyanidin dioxygenase (LDOX) and UDP-glucose: flavonoid 3-O-glucosyltransferase (UFGT) at veraison and an increase in UFGT activity after veraison. These results suggest that the inhibition of anthocyanin biosynthesis in grape berries grown under high night temp. condition could be caused by lower expression levels of anthocyanin biosynthetic genes at an early stage of ripening and lower activities of anthocyanin biosynthetic enzymes, particularly UFGT.

Abstract

Decreased anthocyanin biosynthesis in grape berries grown under elevated night temperature condition. Mori, Kentaro; Sugaya, Sumiko; Gemma, Hiroshi. Doctoral Program in Agricultural Sciences, University of Tsukuba, Ibaraki, Japan. Scientia Horticulturae (Amsterdam, Netherlands) (2005), 105(3), 319-330. Publisher: Elsevier B.V., CODEN: SHRTAH ISSN: 0304-4238. Journal written in English. CAN 143:475013 AN 2005:425378 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The HPLC enantiomeric sepn. of naringenin, eriodictyol, hesperetin and pinocembrin was accomplished in the normal-phase mode using two polysaccharide-derived chiral stationary phases (Chiralcel OD-H and Chiralpak AS-H) and various n-hexane/alc. mobile phases. The 3',4' substituents pattern affect the enantioselectivity of these phases. Single enantiomers of naringenin were isolated by semipreparative HPLC and their CD spectra were measured and related to the abs. configuration by the exciton-coupling method. Online coupling HPLC/spectropolarimeter afforded the CD sign of the eluted peaks at a single wavelength, and the complete CD spectra of the eluted enantiomers were obtained by trapping them in the spectropolarimeter cell through a switching valve.

Abstract

High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones. Caccamese, Salvatore; Caruso, Carmelo; Parrinello, Nunziatina; Savarino, Anna. Dipartimento di Scienze Chimiche, Universita di Catania, Catania, Italy. Journal of Chromatography, A (2005), 1076(1-2), 155-162. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 143:165631 AN 2005:427245 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


to their habitual diet. At the end of 3 wk, mean vitamin C, folate, carotenoid, and flavanone blood plasma concns. were increased relative to baseline by 59%, 46%, 22%, and 8-fold, resp. Flavanones were excreted in urine 9-fold more at the end of the 3-wk intervention, but returned to baseline 2 days after study completion. After the 3-wk intervention, blood plasma concns. of vitamins A and E did not change. White blood cell 8-hydroxydeoxyguanosine levels declined by 16% (n = 11) and in individuals with high baseline concns. by 29% (n = 7). The low-d. lipoprotein/high-d. lipoprotein (LDL/HDL) cholesterol ratios decreased, but cholesterol (HDL, LDL, total) and thiobarbituric acid-reactive substance plasma concns. did not much change. Thus, OJ is an excellent food source to enhance circulating concns. of valuable hydrophilic and lipophilic phytochems.


flavanone

EP 1720986 A2 20061115 EP 2004-810095 20041028US 20050172354 A1 20050804 US 2004-976190 20041028AU 2004286279 A1 20050512 AU 2004-286279 20041028

RW: BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG, AP, EA, EP, OA

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW, US


Medicago truncatula isoflavone 2'- or 3'-hydroxylase cDNA sequences and use thereof in transgenic plants for flavonoid and isoflavonoid nutraceuticals biosynthesis. Dixon, Richard A.; Liu, Chang-Jun. (The Samuel Roberts Noble Foundation, Inc., USA). PCT Int. Appl. (2005), 78 pp. CODEN: PIXXD2 WO 2005042747 A2 20050512 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-US35948 20041028. Priority: US 2003-515559 20031029. CAN 142:442900 AN 2005:409680 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Debittering of grapefruit juice could be accomplished through hydrolyzing the bitter flavanone naringin to purine by α-L-rhamnosidase, and further hydrolyzing purine to naringenin by β-D-glucosidase. The objective of this study was to evaluate the change of antioxidant activity of the partly/completely debittered grapefruit juices. Results demonstrated that all the debittered juices exhibited superior activity (p < 0.05) in scavenging DPPH radicals, hydroxyl radicals, hydrogen peroxide, and superoxide radicals to the control. Addnl., the trolox equiv. antioxidant capacity (TEAC) value of grapefruit juice increased from 2.47 to 4.02 following the debitter processes using both α-L-rhamnosidase and β-D-glucosidase. Moreover, the antioxidant activity of naringenin, the aglycon form of naringin, was significantly (p < 0.05) higher than its glycosides purine and naringin. These results suggest that the enhancement of antioxidant activity in debittered grapefruit juice could be contributed by the flavanones hydrolysis in the juice. This is the first report describes that enzymic debittering could fortify the antioxidant activity of grapefruit juice.

Abstract

Enzymatic hydrolyzing for naringin increase antioxidant activity of grapefruit juice. Chien, Po J.; Sheu, Fuu; Shyu, Yuan T.; Yen, Gow C. Department of Food Science, Yuanpei University of Science and Technology, Hsinchu, Taiwan. Taiwan Nongye Huaxue Yu Shipin Kexue (2005), 43(1), 30-37. Publisher: Agricultural Chemical Society of Taiwan, CODEN: TNHKFW ISSN: 1605-2471. Journal written in Chinese. CAN 143:439021 AN 2005:418609 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


The present inventors have discovered that Flavanone 3-hydroxylase ("FHT") is essential for plant growth. Specifically, the inhibition of FHT gene expression in plant seedlings results in small and chlorotic seedlings. Thus, FHT can be used as a target for the identification of herbicides. Accordingly, the present invention provides methods for the identification of compds. that inhibit FHT expression or activity. The present invention can be used to identify compds. having herbicide activity by contacting a compd. with FHT and detecting the presence and/or absence of binding between the compd. and the FHT, or alternatively, detecting a decrease in FHT expression or activity. The method comprises contacting naringenin, 2-oxoglutarate, and O2 with FHT and the candidate compd., and detg. the concn. of naringenin, 2-oxoglutarate, and O2 and/or 3-dihydrokaempferol, succinate and CO2 after the contact.

Abstract US 2003-702306 20031106Priority Application US 20050100879 A1 20050512 US 2003-702306 20031106 Patent No. Kind Date Application No. Date Patent Family Information

Identification of inhibitors of flavanone 3-hydroxylase expression or activity in plants for screening of herbicides. Davis, Keith; Zayed, Adel; Ascenzi, Robert; Boyes, Douglas; Hoffman, Neil; Gorlach, Jorn; Woessner, Jeffrey; Hamilton, Carol; Phillips, Kenneth. (USA). U.S. Pat. Appl. Publ. (2005), 11 pp. CODEN: USXXCO US 2005100879 A1 20050512 Patent written in English. Application: US 2003-702306 20031106. Priority: . CAN 142:459686 AN 2005:409119 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention provides cDNA sequences of Medicago truncatula isoflavone 2'- or 3'-hydroxylase, and sequence homologs from other plants. Also provided are constructs comprising these sequences, plants transformed therewith and methods of use thereof. In certain aspects of the invention, plants transformed with the nucleic acids are provided exhibiting improved pest and disease resistance. Plants provided by the invention may also exhibit improved nutritional qualities.

Abstract WO 2004-US35948 W 20041028US 2003-515559P P 20031029Priority Application

R: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LI, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, AL, HR, LT, LV, MK


flavanone


Recently, data which prove that Wnt pathway activation may be an early event in multistep carcinogenesis in the stomach have been accumulating. We examd. the effect of flavanone against β-catenin/Tcf signaling in AGS gastric cancer cells. Reporter gene assay showed that flavanone inhibited β-catenin/Tcf signaling efficiently. In addn., the inhibition of β-catenin/Tcf signaling by flavanone in HEK293 cells transiently transfected with constitutively mutant β-catenin gene, whose product is not phosphorylated by GSK3β, indicates that its inhibitory mechanism was related to β-catenin itself or downstream components. To investigate the precise inhibitory mechanism, we performed immunofluorescence, Western blot, and EMSA. As a result, our data revealed that there is no change of β-catenin distribution and of nuclear β-catenin levels through flavanone. In addn., the binding of Tcf complexes to DNA is not influenced by flavanone. The β-catenin/Tcf transcriptional target gene cyclin D1 was downregulated by flavanone. These data suggest that flavanone inhibits the transcription of β-catenin/Tcf responsive genes, by modulating Tcf activity without disrupting β-catenin/Tcf complex formation.

Abstract

Inhibition of β-catenin-mediated transactivation by flavanone in AGS gastric cancer cells. Park, Chi Hoon; Hahm, Eun Ryeong; Lee, Ju Hyung; Jung, Kyung Chae; Yang, Chul Hak. Division of Chemistry and Molecular Engineering, Seoul National University, Seoul, S. Korea. Biochemical and Biophysical Research Communications (2005), 331(4), 1222-1228. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 143:38040 AN 2005:393597 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


An integrated, bioinformatic anal. of three databases comprising tumor-cell-based small mol. screening data, gene expression measurements, and PDB (Protein Data Bank) ligand-target structures has been developed for probing mechanism of drug action (MOA). Clustering anal. of GI50 profiles for the NCI's database of compds. screened across a panel of tumor cells (NCI60) was used to select a subset of unique cytotoxic responses for about 4000 small mols. Drug-gene-PDB relationships for this test set were examd. by correlative anal. of cytotoxic response and differential gene expression profiles within the NCI60 and structural comparisons with known ligand-target crystallog. complexes. A survey of mol. features within these compds. finds thirteen conserved Compd. Classes, each class exhibiting chem. features important for interactions with a variety of biol. targets. Protein targets for an addnl. twelve Compd. Classes could be directly assigned using drug-protein interactions obsd. in the crystallog. database. Results from the anal. of constitutive gene expressions established a clear connection between chemo-resistance and overexpression of gene families assocd. with the extracellular matrix, cytoskeletal organization, and xenobiotic metab. Conversely, chemo-sensitivity implicated overexpression of gene families involved in homeostatic functions of nucleic acid repair, aryl hydrocarbon metab., heat shock response, proteasome degrdn. and apoptosis. Correlations between chemo-responsiveness and differential gene expressions identified chemotypes with nonselective (i.e., many) mol. targets from those likely to have selective (i.e., few) mol. targets. Applications of data mining strategies that jointly utilize tumor cell screening, genomic, and structural data are presented for hypotheses generation and identifying novel anti-cancer candidates.

Abstract

Linking tumor cell cytotoxicity to mechanism of drug action: An integrated analysis of gene expression, small-molecule screening and structural databases. Covell, David G.; Wallqvist, Anders; Huang, Ruili; Thanki, Narmada; Rabow, Alfred A.; Lu, Xiang-Jun. Developmental Therapeutics Program, Screening Technologies Branch, Laboratory of Computational Technologies, National Cancer Institute-Frederick, Frederick, MD, USA. Proteins: Structure, Function, and Bioinformatics (2005), 59(3), 403-433. Publisher: Wiley-Liss, Inc., CODEN: PSFBAF Journal written in English. CAN 143:37868 AN 2005:400966 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


The concns. of prenylated chalcones and bitter acids were analyzed in Czech hop varieties. The highest levels of (xanthohumol + desmethylxanthohumol) (0.97%, m/m) and of total bitter acids (17.19%, m/m) were obsd. for cv. Agnus. The concn. ratios of bitter acids to prenylated chalcones varied depending on the genotype, thereby suggesting genetic detn. by different set(s) of structural and regulatory genes. Promoter elements of the chs_H1 gene encoding a "true" chalcone synthase, a candidate gene to co-det. the biosynthesis of prenylated chalcones, were analyzed, and several boxes for cis-regulatory elements including Myb transcription factors were discovered. A cDNA library was established from glandular tissue-enriched cones of cv. Osvald's clone 72 and used to screen for Myb regulatory elements. The cDNA of the first Myb regulatory factor from hop, called HlMyb1, was cloned and analyzed. The HlMyb1 open reading frame encodes 272 amino acids (29.8 kDa), and the protein showed highest homol. to the light-regulated factor AtMyb68 from Arabidopsis thaliana within the Myb domain, whereas there was no significant homol. with known MYB proteins outside this domain. Unlike AtMyb68, which is expressed in mature leaves, HlMyb1 is strongly expressed in hop inflorescences and could participate in the regulation of developmental processes involved in the prodn. of hop cones and bioactive secondary metabolites.

Abstract

Cloning and molecular analysis of the regulatory factor HlMyb1 in Hop (Humulus lupulus L.) and the potential of Hop to produce bioactive prenylated flavonoids. Matousek, Jaroslav; Vrba, Lukas; Novak, Petr; Patzak, Josef; De Deeukeleire, Jelle; Skopek, Josef; Heyerick, Arne; Roldan-Ruiz, Isabel; De Keukeleire, Denis. Institute of Plant Molecular Biology AS CR, Ceske Budejovice, Czech Rep. Journal of Agricultural and Food Chemistry (2005), 53(12), 4793-4798. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:93948 AN 2005:376621 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chalcone synthase (CHS), the key enzyme in the flavonoid biosynthesis pathway, is encoded by a multigene family, CHS1-CHS8 and dCHS1 in soybean. A tandem repeat of CHS1, CHS3 and CHS4, and dCHS1 that is believed to be located in the vicinity comprises the I locus that suppresses coloration of the seed coat. This study was conducted to det. the location of all CHS members by using PCR-based DNA markers. Primers were constructed based on varietal differences in either the nucleotide sequence of the 5'-upstream region or the first intron of two cultivars, Misuzudaizu, with a yellow seed coat (II), and Moshidou Gong 503, with a brown seed coat (ii). One hundred and fifty recombinant inbred lines that originated from a cross between these two cultivars were used for linkage mapping together with 360 markers. Linkage mapping confirmed that CHS1, CHS3, CHS4, dCHS1, and the I locus are located at the same position in mol. linkage group (MLG) A2. CHS5 was mapped at a distance of 0.3 cM from the gene cluster. CHS2 and CHS6 were located in the middle region of MLGs A1 and K, resp., while CHS7 and CHS8 were found at the distal end of MLGs D1a and B1, resp. Phylogenetic anal. indicated that CHS1, CHS3, CHS4, and CHS5 are closely related, suggesting that gene duplication may have occurred repeatedly to form the I locus. In addn., CHS7 and CHS8 located at the distal end and CHS2, CHS6, and CHS members around the I locus located around the middle of the MLG are also related. Ancient tetraploidization and repeated duplication may be responsible for the evolution of the complex genetic loci of the CHS multigene family in soybean.

Abstract

Molecular linkage mapping and phylogeny of the chalcone synthase multigene family in soybean. Matsumura, H.; Watanabe, S.; Harada, K.; Senda, M.; Akada, S.; Kawasaki, S.; Dubouzet, E. G.; Minaka, N.; Takahashi, R. Graduate School of Life and Environmental Sciences, University of Tsukuba, Tsukuba, Ibaraki, Japan. Theoretical and Applied Genetics (2005), 110(7), 1203-1209. Publisher: Springer GmbH, CODEN: THAGA6 ISSN: 0040-5752. Journal written in English. CAN 143:456231 AN 2005:377843 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Partial reconstruction of flavonoid and isoflavonoid biosynthesis in yeast using soybean type I and type II chalcone Bibliographic Information Answer 627:

Octanol-water partition coeff. (log P) values were detd. for flavonoids from the flavone, flavonol, flavanone, and isoflavonoid subclasses. Each flavonoid was dissolved in an octanol-water system and allowed to equilibrate, and then both fractions were analyzed by high-performance liq. chromatog. Log P was calcd. as log[ratio of the concn. in the octanol phase to the concn. in the aq. phase at pH 7.4]. The aglycons were more lipophilic than any conjugate. The conjugate moiety had a more significant effect on log P than the aglycon moiety. Quercetin was the least lipophilic aglycon (log P = 1.82 ± 0.32) and, together with kaempferol (log P = 3.11 ± 0.54), gave the most variable results. The isoflavones genistein and daidzein and the isoflavone metabolite equol gave relatively high log P values (3.04 ± 0.02, 2.51 ± 0.06, and 3.20 ± 0.13, resp.), while glycitein had an unexpectedly low value of 1.97 ± 0.05. The conjugation characteristics and hydroxylation pattern were the most important determinants of log P in general, and log P was highly variable within the flavonoid subclass. The results are discussed in terms of further understanding of the in vivo fate of the flavonoids as important dietary bioactives.

Abstract

Experimental Determination of Octanol-Water Partition Coefficients of Quercetin and Related Flavonoids. Rothwell, Joseph A.; Day, Andrea J.; Morgan, Michael R. A. Procter Department of Food Science, University of Leeds, Leeds, UK. Journal of Agricultural and Food Chemistry (2005), 53(11), 4355-4360. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:77045 AN 2005:373733 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Bioactive compds. (vitamin C, carotenoids, and flavanones) and DPPH.bul. radical scavenging capacity (RSC) were measured in orange juice (OJ) subjected to different technologies. High pressure (HP) (400 MPa/40 °C/1 min), pulsed elec. fields (PEF) (35 kVcm-1/750 μs), low pasteurization (LPT) (70 °C/30 s), high pasteurization (HPT) (90 °C/1 min), HPT plus freezing (HPT+F) (-38 °C/15 min), and freezing (F) were studied. Among the treatments assayed, even though the losses in total vitamin C were <9%, treatments with the higher temps. tended to show the higher decrease in the content of both forms of vitamin C. HP treatment led to an increased carotenoid release (53.88%) and vitamin A value (38.74%). PEF treatment did not modify individual or total carotenoids content. Traditional thermal treatments did not exert any effect on total carotenoid content or vitamin A value. With regard to individual carotenoid extn., HPT and HPT+F led to different releases of carotenoids. With respect to flavanones, HP treatment led to increased naringenin (20.16%) and hesperetin (39.88%) contents, whereas PEF treatment did not modify flavanone content. In general, pasteurization and freezing process led to a diminished naringenin content (16.04%), with no modification in hesperetin. HP and PEF treatments did not modify DPPH.bul. RSC. In the case of traditional thermal technologies, HPT treatment showed a decrease in RSC (6.56%), whereas LPT, HPT+F, and F treatments did not modify RSC. Vitamin C modulated RSC, in terms of antioxidant concn. (EC50) and kinetics (AE = 1/EC50TEC50), in the treated and untreated OJ. In summary, HP and PEF technologies were more effective than HPT treatment in preserving bioactive compds. and RSC of freshly squeezed orange juice.

Abstract

Impact of High Pressure and Pulsed Electric Fields on Bioactive Compounds and Antioxidant Activity of Orange Juice in Comparison with Traditional Thermal Processing. Sanchez-Moreno, Concepcion; Plaza, Lucia; Elez-Martinez, Pedro; De Ancos, Begona; Martin-Belloso, Olga; Cano, M. Pilar. Department of Plant Foods Science and Technology, Instituto del Frio, CSIC, Madrid, Spain. Journal of Agricultural and Food Chemistry (2005), 53(11), 4403-4409. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 143:77281 AN 2005:373734 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Hydrophobic properties of a number of monosubstituted flavone and flavanone derivatives. Pogodaeva, N. N.; Medvedeva, Bibliographic Information Answer 629:

A Trolox equiv. antioxidant capacity (TEAC) decolorization assay was adapted to a flow injection anal. (FIA) system and a simple and rapid method for antioxidant activity evaluation was developed. To avoid the time consuming step of 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation prepn. by chem. oxidn. of ABTS, as in the original TAEC assay, and hence, to shorten the anal. time, the ABTS radical cation was generated online by electrochem. oxidn. of ABTS in the flow-through electrolysis cell forming a part of the FIA system. The proposed method was optimized with respect to a flow rate, injection vol. and ABTS radical cation/carrier ratio. Under the optimized conditions linear calibration graphs for Trolox were obtained over the range 10-100 μM, with a limit of detection 1.6 μM. Good reproducibility (relative std. deviation 1.95%) and sample throughput (32 samples per h) were achieved. The developed method was applied to the evaluation of the antioxidant activity of pure compds. and samples of some common beverages. In both cases a good correlation between the results obtained by the proposed method and TEAC values evaluated by the classic TAEC decolorization assay was obtained (r2 = 0.996 for pure compds. and r2 = 0.957 for beverage samples).

Abstract

Evaluation of the antioxidant activity by flow injection analysis method with electrochemically generated ABTS radical cation. Ivekovic, Damir; Milardovic, Stjepan; Roboz, Mario; Grabaric, Bozidar S. Laboratory of General and Inorganic Chemistry and Electroanalysis, Faculty of Food Technology and Biotechnology, University of Zagreb, Zagreb, Croatia. Analyst (Cambridge, United Kingdom) (2005), 130(5), 708-714. Publisher: Royal Society of Chemistry, CODEN: ANALAO ISSN: 0003-2654. Journal written in English. CAN 143:42863 AN 2005:357473 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids and isoflavonoids are major plant secondary metabolites that mediate diverse biol. functions and exert significant ecol. impacts. These compds. play important roles in many essential physiol. processes. In addn., flavonoids and isoflavonoids have direct but complex effects on human health, ranging from reducing cholesterol levels and preventing certain cancers to improving women's health. In this study, we cloned and functionally characterized five soybean (Glycine max) chalcone isomerases (CHIs), key enzymes in the phenylpropanoid pathway that produces flavonoids and isoflavonoids. Gene expression and kinetics anal. suggest that the soybean type I CHI, which uses naringenin chalcone as substrate, is coordinately regulated with other flavonoid-specific genes, while the type II CHIs, which use a variety of chalcone substrates, are coordinately regulated with an isoflavonoid-specific gene and specifically activated by nodulation signals. Furthermore, we found that some of the newly identified soybean CHIs do not require the 4'-hydroxy moiety on the substrate for high enzyme activity. We then engineered yeast (Saccharomyces cerevisiae) to produce flavonoid and isoflavonoid compds. When one of the type II CHIs was coexpressed with an isoflavone synthase, the enzyme catalyzing the first committed step of isoflavonoid biosynthesis, various chalcone substrates added to the culture media were converted to an assortment of isoflavanones and isoflavones. We also reconstructed the flavonoid pathway by coexpressing CHI with either flavanone 3β-hydroxylase or flavone synthase II. The in vivo reconstruction of the flavonoid and isoflavonoid pathways in yeast provides a unique platform to study enzyme interactions and metabolic flux.

Abstract

isomerases. Ralston, Lyle; Subramanian, Senthil; Matsuno, Michiyo; Yu, Oliver. Donald Danforth Plant Science Center, St. Louis, MO, USA. Plant Physiology (2005), 137(4), 1375-1388. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 143:55477 AN 2005:372992 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract WO 2004-EP11466 W 20041006EP 2003-90335 A 20031007Priority Application US 20070276032 A1 20071129 US 2007-575391 20070205 JP 2007507462 T 20070329 JP 2006-530149 20041006

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, HU, PL, SK, HR

EP 1670777 A1 20060621 EP 2004-765949 20041006

RW: BW, GH, GM, KE, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG


WO 2005037816 A1 20050428 WO 2004-EP11466 20041006



Preparation and use of 8-prenylnaringenin for hormone replacement therapy. Huempel, Michael; Schleuning, Wolf-Dieter; Schaefer, Olaf; Isaksson, Paeivi; Bohlmann, Rolf. (Schering Aktiengesellschaft, Germany). Eur. Pat. Appl. (2005), 19 pp. CODEN: EPXXDW EP 1524269 A1 20050420 Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, HU, SK. Patent written in English. Application: EP 2003-90335 20031007. Priority: . CAN 142:392216 AN 2005:345922 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The distribution of flavone, 7-,5-,3-,4'-hydroxyflavones, 3-, 4'-methoxyflavones, and 3-hydroxyflavanone in the octanol-water system was studied. The hydrophobicity consts. of the flavonoids were detd. It was shown that, when a hydroxy group is substituted into position 4', the hydrophobicity of flavone decreases, increasing, however, when it is substituted into positions 7, 5, or 3; the increase is higher the closer it is located to the carbonyl (electron-acceptor) group.

Abstract

S. A. Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, Russia. Russian Journal of Physical Chemistry (2005), 79(4), 645-648. Publisher: Pleiades Publishing, Inc., CODEN: RJPCAR ISSN: 0036-0244. Journal written in English. CAN 144:6593 AN 2005:351490 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


Development of restriction fragment length polymorphism (RFLP) markers for identification of strawberry cultivars. Kuniji, Miyuki; Matsumoto, Akira; Fukino, Nobuko. (National Institute of Agro-Environmental Sciences, Japan). Jpn. Kokai Tokkyo Koho (2005), 34 pp. CODEN: JKXXAF JP 2005102535 A 20050421 Patent written in Japanese. Application: JP 2003-337714 20030929. Priority: . CAN 142:405501 AN 2005:340272 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


It has been recently reported the presence in Valeriana of the flavone 6-methylapigenin and the flavanone glycoside hesperidin. The apigenin deriv. is a ligand for the benzodiazepine binding site in the γ-aminobutyric acid receptor type A (GABAA) and has anxiolytic properties. Hesperidin has sedative and sleep-enhancing properties but is not a ligand for the benzodiazepine binding site. 6-Methylapigenin is able to potentiate the sleep-enhancing effect of hesperidin. In this work we demonstrate that this property is shared with various GABAA receptor ligands, among them the agonist diazepam, which was used to study the potentiation as measured in the hole board test. Isobolar anal. of the results showed the interaction being synergistic. We discarded pharmacokinetic effects or a direct action of hesperidin on the benzodiazepine binding site. A possible use of hesperidin properties to decrease the effective therapeutic doses of benzodiazepines is suggested.

Abstract

Synergistic interaction between hesperidin, a natural flavonoid, and diazepam. Fernandez, Sebastian P.; Wasowski, Cristina; Paladini, Alejandro C.; Marder, Mariel. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica Biologicas, Buenos Aires, Argent. European Journal of Pharmacology (2005), 512(2-3), 189-198. Publisher: Elsevier B.V., CODEN: EJPHAZ ISSN: 0014-2999. Journal written in English. CAN 142:441768 AN 2005:345728 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

HO

OH

Me Me

I

The present invention provides a method for the synthesis of phytoestrogen 8-prenylnaringenin (I) comprising the steps: (a) diacetylation of naringenin, (b) prenylation using tributyl-phosphine and diisopropylazodicarboxylate, (c) rearrangement of prenyl side chain using europium(III)-fod and (d) solvolysis using K2CO3 in methanol/H2O. The prepd. naringenin deriv. I was utilized for the prodn. of a medicament for the prevention and treatment of hormone-dependent osteoporosis and of peri- and postmenopausal symptoms in women wherein the effect of said medicament on uterus proliferation is less than 1/5 of that of estradiol (II) and the doses of I and II which are compared are equieffective on bone mass redn.


flavanone

Chalcones and other flavonoids from Asarum sensu lato (Aristolochiaceae). Iwashina, Tsukasa; Kitajima, Junichi; Shiuchi, Toshiaki; Itou, Yutaka. Tsukuba Botanical Garden, National Science Museum, Tsukuba, Ibaraki, Japan. Biochemical Systematics and Ecology (2005), 33(6), 571-584. Publisher: Elsevier B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English.


Glandular trichomes are a major site of plant natural product synthesis and accumulation for protection against insect predation. However, to date few studies have attempted to obtain a global view of trichome gene expression. Two contrasting approaches have been adopted to investigate genes expressed in glandular trichomes from alfalfa (Medicago sativa). In the first approach, 5674 clones from an alfalfa glandular trichome cDNA library were sequenced. The most highly abundant expressed sequence tag (EST) corresponded to a lipid transfer protein. The presence of ESTs corresponding to enzymes for all steps in the biosynthesis of flavonoids suggests that these are important metabolites in alfalfa trichome biol., as confirmed by histochem. and metabolite profiling. No ESTs corresponded to enzymes of cyclized terpenoid biosynthesis. In a second approach, microarray anal. was used to compare levels of alfalfa transcripts corresponding to 16,086 Medicago truncatula A17 genes in stems with and without trichomes. This revealed over 1000 genes with strong preferential expression in the trichome fraction of the stem, 70% of which are of unknown function. These define a class of genes that are not trichome-specific, since M. truncatula A17 does not itself have glandular trichomes, but has potential importance for trichome function within the stem. The EST sequences are deposited in GenBank/EMBL/DDBJ under accession nos. CO511688-CO517334.

Abstract

Transcriptome analysis of alfalfa glandular trichomes. Aziz, Naveed; Paiva, Nancy L.; May, Gregory D.; Dixon, Richard A. Plant Biology Division, Samuel Roberts Noble Foundation, Ardmore, OK, USA. Planta (2005), 221(1), 28-38. Publisher: Springer GmbH, CODEN: PLANAB ISSN: 0032-0935. Journal written in English. CAN 142:460124 AN 2005:339691 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A method for identifying strawberry cultivars by PCR-RFLP is disclosed. Using one of 19 pairs of primers, DNA extd. from fruit, calyx, leaf, or stalk of strawberry, are amplified by PCR. PCR amplified fragments are then digested with a restriction enzyme and resulting restriction fragment length polymorphisms (RFLPs) are analyzed. The authors developed 19 restriction fragment length polymorphism (RFLP) markers to identify strawberry (Fragaria × ananassa Duch.) cultivars, with an aim of protecting breeders' rights. The DNA is extd. from calyx-contg. fruit and/or leaf of strawberry and analyzed by PCR for genotyping. They successfully used them to distinguish 24 com. cultivars. The results were highly reproducible among different extn. methods, different organs and different researchers.

Abstract JP 2003-337714 20030929Priority Application JP 4065951 B2 20080326JP 2005102535 A 20050421 JP 2003-337714 20030929Patent No. Kind Date Application No. Date


flavanone

Abstract

Differential combinatorial interactions of cis-acting elements recognized by R2R3-MYB, BZIP, and BHLH factors control light-responsive and tissue-specific activation of phenylpropanoid biosynthesis genes. Hartmann, Ulrike; Sagasser, Martin; Mehrtens, Frank; Stracke, Ralf; Weisshaar, Bernd. Department of Plant Breeding and Yield Physiology, Max-Planck-Institute for Plant Breeding Research, Cologne, Germany. Plant Molecular Biology (2005), 57(2), 155-171. Publisher: Kluwer Academic Publishers, CODEN: PMBIDB ISSN: 0167-4412. Journal written in English. CAN 143:280320 AN 2005:309298 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In this study we isolated the partial cDNA clone of three enzymes active in the late steps of anthocyanins biosynthetic pathway such as DFR, ANS and UFGT from Citrus sinensis (L) Osbeck. The predicted amino acids sequences shared very high identity values ranging from 77% for DFR (Pyrus communis, Malus domestica), to 86% for ANS (Vitis vinifera) with homologous available protein sequences. Only the UFGT sequence showed lower identity value (59%), but this finding is in accordance with data obtained for other enzymes belonging to the plant glucosyl transferase superfamily. The expression of CHS, CHI, F3OH, DFR, ANS and UFGT was also investigated in both colored and uncolored oranges juice vesicles. Transcripts encoding the enzymes involved in the earlier reactions have been detected in either blood and blonde oranges by RT-PCR. Conversely, considerable difference emerged in the case of the later gene ufgt which was totally unexpressed in blonde oranges juice vesicles probably detg. the lack of anthocyanins prodn. in all blonde orange cultivars analyzed.

Abstract

Anthocyaninless cultivars of sweet orange lack to express the UDP-glucose flavonoid 3-O-glucosyl transferase. Lo Piero, Angela R.; Consoli, Alessandro; Puglisi, Ivana; Orestano, Greta; Recupero, Giuseppe Reforgiato; Petrone, Goffredo. Dipartimento di Scienze Agronomiche, Agrochimiche e delle Produzioni Animali, Facolta di Agraria, Universita degli Studi, Catania, Italy. Journal of Plant Biochemistry and Biotechnology (2005), 14(1), 9-14. Publisher: Society for Plant Biochemistry and Biotechnology, CODEN: JPBBEE ISSN: 0971-7811. Journal written in English. CAN 143:382820 AN 2005:313748 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Seventy-five taxa belonging to the genus Asarum sensu lato were studied for their compn. of flavonoids. Three chalcones and an aurone were found as major components. The chalcones were identified as chalcononaringenin 2',4'-di-O-glucoside, 4,2',4'-tri-O-glucoside, 4-O-glucoside, and the aurone as aureisidin 4,6-di-O-glucoside. The glycoside, 2',4'-di-O-glucoside was detected in all taxa examd., and is a chemotaxonomical feature of Asarum sensu lato. 4,2',4'-Tri-O-glucoside was found from the taxa classified into the genera Asiasarum, Geotaenium and Heterotropa by Maekawa's system. On the other hand, the glycoside was not detected from three Asarum sensu stricto species, A. caudigerum, A. caulescens and A. leptophyllum. In contrast, aurone, aureusidin 4,6-di-O-glucoside occurred in two Asarum s.s., A. caulescens and A. leptophyllum. Thus, the Asarum s.s. and other Maekawa's genera, Asiasarum, Geotaenium and Heterotropa could distinguish by the presence or absence of some anthochlor pigments. Other flavonoids were isolated from the selected 18 Asarum species. They were characterized as some flavonol 3- or 3,7-O-glycosides based on kaempferol, quercetin and isorhamnetin, flavone, apigenin 6,8-di-C-glycoside, flavanone, naringenin 5,7-di-O-glucoside, and xanthone, mangiferin.

Abstract CAN 143:263455 AN 2005:320994 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The leguminous isoflavonoid skeleton is constructed by P 450 2-hydroxyisoflavanone synthase (CYP93C). Two active-site residues of CYP93C2, Ser 310 and Lys 375, are crit. for unusual aryl migration of the flavanone substrate. Leu 371 is located near the

Abstract

Multiple mutagenesis of P450 isoflavonoid synthase reveals a key active-site residue. Sawada, Yuji; Ayabe, Shin-ichi. Department of Applied Biological Sciences, Nihon University, Fujisawa, Kanagawa, Japan. Biochemical and Biophysical Research Communications (2005), 330(3), 907-913. Publisher: Elsevier, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 143:3102 AN 2005:289082 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The potential vasorelaxant, antioxidant, and cyclic nucleotide phosphodiesterase (PDE) inhibitory effects of the citrus-fruit flavonoids naringin and (±)-naringenin were comparatively studied for the 1st time in this work. (±)-Naringenin (1 μM - 0.3 mM) did not affect the contractile response induced by okadaic acid (OA, 1 μM). However, (±)-naringenin relaxed, in a concn.-dependent manner, the contractions elicited by phenylephrine (PHE, 1 μM) or by a high extracellular KCl concn. (60 mM) in intact rat aortic rings. Mech. removal of endothelium and/or pretreatment of aorta rings with glibenclamide (GB, 10 μM) or tetraethylammonium (TEA, 2 mM) did not significantly modify the vasorelaxant effects of this flavanone. (±)-Naringenin (10 μM - 0.1 mM) did not alter the basal uptake of 45Ca2+ but decreased the influx of 45Ca2+ induced by PHE and KCl in endothelium-contg. and endothelium-denuded rat aorta. (±)-Naringenin (10 μM - 0.1 mM) was ineffective to scavenge superoxide radicals (O2⋅-) generated by the hypoxanthine (HX)-xanthine oxidase (XO) system and/or to inhibit XO activity. (±)-Naringenin (0.1 mM) significantly increased the prodn. of cGMP and cAMP decreased by PHE (1 μM) and high KCl (60 mM) in cultured rat aortic myocytes. (±)-Naringenin preferentially inhibited calmodulin (CaM)-activated PDE1, PDE4, and PDE5 isolated from bovine aorta with IC50 values of about 45, 60, and 68 μM, resp. In contrast, the 7-rhamnoglucoside of (±)-naringenin, naringin (1 μM - 0.3 mM), was totally inactive in all expts. These results indicate that the vasorelaxant effects of (±)-naringenin seem to be basically related to the inhibition of PDE1, PDE4, and PDE5 activities.

Abstract

Implication of cyclic nucleotide phosphodiesterase inhibition in the vasorelaxant activity of the citrus-fruits flavonoid (±)-naringenin. Orallo, Francisco; Camina, Mercedes; Alvarez, Ezequiel; Basaran, Helene; Lugnier, Claire. Departamento de Farmacologia, Facultad de Farmacia, Universidad de Santiago de Compostela, Santiago de Compostela, Spain. Planta Medica (2005), 71(2), 99-107. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 142:475742 AN 2005:295616 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chalcone synthase (CHS), chalcone flavanone isomerase (CFI), flavanone 3-hydroxylase (F3H) and flavonol synthase (FLS) catalyze successive steps in the biosynthetic pathway leading to the prodn. of flavonols. The authors show that in Arabidopsis thaliana all four corresponding genes are coordinately expressed in response to light, and are spatially coexpressed in siliques, flowers and leaves. Light regulatory units (LRUs) sufficient for light responsiveness were identified in all four promoters. Each unit consists of two necessary elements, namely a MYB-recognition element (MRE) and an ACGT-contg. element (ACE). C1 and Sn, a R2R3-MYB and a BHLH factor, resp., known to control tissue specific anthocyanin biosynthesis in Z. mays, were together able to activate the AtCHS promoter. This activation of the CHS promoter required an intact MRE and a newly identified sequence designated R response element (RREAtCHS) contg. the BHLH factor consensus binding site CANNTG. The RRE was dispensable for light responsiveness, and the ACE was not necessary for activation by C1/Sn. These data suggest that a BHLH and a R2R3-MYB factor cooperate in directing tissue-specific prodn. of flavonoids, while an ACE-binding factor, potentially a BZIP, and a R2R3-MYB factor work together in conferring light responsiveness.


flavanone

Answer 641:

The cDNA clones encoding homologs of flavanone 3-hydroxylase (F3H), anthocyanidin synthase (ANS), flavonoid 3'-hydroxylase (F3'H) and flavone synthase II (FSII) genes were isolated from petals of Gentiana triflora. Deduced amino acid sequences exhibited 60-80% identities with the corresponding sequences from other dicotyledonous species. Southern blot anal. showed that they were present as multiple copies in the gentian genome, and Northern blot anal. showed that the flavonoid biosynthesis-related genes could be classified into three groups by their temporal expression patterns during gentian flower development. The first included chalcone synthase (CHS) and chalcone isomerase (CHI) expressing during all flower development stages; the second included F3'H and FSII expressing at flower early developmental stages; and the third included F3H, flavonoid 3',5'-hydroxylase (F3',5'H), dihydroflavonol 4-reductase (DFR), ANS, UDP-glucose:flavonoid 3-O-glucosyltransferase (3GT) and anthocyanin 5-arom. acyltransferase (5AT) expressing at flower late developmental stages. In general, low or undetectable levels of expression were obsd. in both the leaves and stems. High performance liq. chromatog. (HPLC) anal. revealed that flavone accumulates from the early flower bud stage, but anthocyanin accumulation peaked at the later flower anthesis stage. A significant correlation between gene expression and pigment accumulation has been found, indicating that flavonoid biosynthesis during gentian flower development is regulated by temporal expression of these genes.

Abstract

Temporal expression of flavonoid biosynthesis-related genes regulates flower pigmentation in gentian plants. Nakatsuka, Takashi; Nishihara, Masahiro; Mishiba, Keiichiro; Yamamura, Saburo. Iwate Biotechnology Research Center, Kitakami, Iwate, Japan. Plant Science (Amsterdam, Netherlands) (2005), 168(5), 1309-1318. Publisher: Elsevier B.V., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 143:226020 AN 2005:280316 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Three new flavanone glycosides, naringenin 4'-O-β-D-glucuronopyranoside, naringenin 4'-O-α-L rhamnopyranoside and naringenin 4'-O-β-D-xylopyranoside, were characterized from the leaves of Impatiens bicolor, together with 6 known glycosides: naringenin 4'-O-β-D-glucopyranoside, kaempferol 7-O-β-D-glucuronopyranoside, quercetin 3-O-β-D-glucopyranoside, kaempferol 5-O-β-D-xylopyranoside, kaempferol 3-O-β-D-galactopyranoside and kaempferol 7-O-β-D-xylopyranoside. The structures were detd. by means of co-chromatog., UV, HPLC, EI-MS, FAB-MS and 1H NMR.

Abstract

Flavonoids from the leaves of Impatiens bicolor. Hasan, Aurangzeb; Tahir, Muhammad Nawaz. Department of Chemistry, Quaid-i-Azam University, Islamabad, Pak. Turkish Journal of Chemistry (2005), 29(1), 65-70. Publisher: Scientific and Technical Research Council of Turkey, CODEN: TJCHE3 ISSN: 1300-0527. Journal written in English. CAN 143:208917 AN 2005:288821 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


substrate in a homol. model, and mutant proteins regarding this residue were expressed in recombinant yeast microsomes. The single mutant, L371V, yielded only inactive P420, but multiple mutants incorporating K375T restored the P 450 fold: the S310T-L371V-K375T triple mutant showed four times higher P 450 level than the wild type. L371V-K375T and S310T-L371V-K375T produced a mixt. of major 3β-hydroxyflavanone and minor flavone, and 100% flavone, resp., from a flavanone. Thus, Leu 371 appeared to control the substrate accommodation in favor of hydrogen abstraction from C-3 of the flavanone mol. and contribute to the P 450 fold under the presence of Lys 375, the residue responsible for aryl migration. The mol. evolution of CYP93 enzymes is discussed.


flavanone

Cytotoxic lignans from Larrea tridentata. Lambert, Joshua D.; Sang, Shengmin; Dougherty, Ann; Caldwell, Colby G.; Meyers, Ross O.; Dorr, Robert T.; Timmermann, Barbara N. Department of Chemical Biology, Ernest Mario School of Pharmacy, Rutgers,


O

O

OMeO

OMe

O I

A novel flavonolignan analog 7,3'-dimethoxy-4',5'-ethylenedioxyflavanone (I) was synthesized from Vanillin and m-benzenediol by seven steps in 16.1 % overall yield. The structure was confirmed by 1H NMR, IR and MS.

Abstract

Synthesis of 7,3'-dimethoxy-4',5'-ethylenedioxyflavanone. Wang, Qiu-an; Zhang, Chun-xiang; Ma, Qiu-juan. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Peop. Rep. China. Hecheng Huaxue (2005), 13(1), 67-69, 72. Publisher: Hecheng Huaxue Bianjibu, CODEN: HEHUE2 ISSN: 1005-1511. Journal written in Chinese. CAN 144:212552 AN 2005:274831 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The cor. versions of Figures 1 and 3 and the legends to Figure 2, Figure 6, and Table 1 are given. On page 1330, left-hand column, line 4 from the bottom should read: "Royal Free & University College Medical School". The cor. versions of paragraph 3 in the right-hand column on page 1338 and the beginning of paragraph 2 in the left-hand column on page 1339 are given.

Abstract

The differential tissue distribution of the citrus flavanone naringenin following gastric instillation. [Erratum to document cited in CA142:168926]. Abd El Mohsen, Manal; Marks, Joanne; Kuhnle, Gunter; Rice-Evans, Catherine; Moore, Kevin; Gibson, Glenn; Debnam, Edward; Srai, S. Kaila. Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, Kings College London, London, UK. Free Radical Research (2005), 39(2), 221-223. Publisher: Taylor & Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in English. CAN 143:278325 AN 2005:279266 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 645:

Isoflavones are synthesized by isoflavone synthases via the phenylpropanoid pathway in legumes. We have cloned two isoflavone synthase genes, IFS1 and IFS2, from a total of 18 soybean cultivars. The amino acid residues of the proteins that differed between cultivars were dispersed over the entire coding region. However, amino acid sequence variation did not occur in conserved domains such as the ERR triad region, except that one conserved amino acid was changed in the IFS2 protein of the GS12 cultivar (R374G) and the IFS1 proteins of the 99M06 and Soja99s65 cultivars (A109T, F105I). In three cultivars (99M06, 99M116, and Simheukpi), most of amino acid changes were such that the difference between the amino acid sequences of IFS1 and IFS2 was reduced. The expression profiles of three enzymes that convert naringenin to the isoflavone, genistein, chalcone isomerase (CHI), isoflavone synthase (IFS) and flavanone 3-hydroxylase (F3H) were examd. In general, IFS mRNA was more abundant in etiolated seedings than mature plants whereas the levels of CHI and F3H mRNAs were similar in the two stages. During seed development, IFS was expressed a little later than CHI and F3H but expression of these three genes was barely detectable, if at all, during later seed hardening. In addn., we found that the levels of CHI, F3H, and IFS mRNAs were under circadian control. We also showed that IFS was induced by wounding and by application of Me jasmonate to etiolated soybean seedings.

Abstract

Polymorphism and expression of isoflavone synthase genes from soybean cultivars. Kim, Hyo-Kyoung; Jang, Yun-Hee; Baek, Il-Sun; Lee, Jeong-Hwan; Park, Min Joo; Chung, Young-Soo; Chung, Jong-Il; Kim, Jeong-Kook. School of Life Sciences and Biotechnology, Korea University, Seoul, S. Korea. Molecules and Cells (2005), 19(1), 67-73. Publisher: Korean Society for Molecular and Cellular Biology, CODEN: MOCEEK ISSN: 1016-8478. Journal written in English. CAN 143:302493 AN 2005:261109 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OH

HO

MeO

OMe

Me

Me

I

Six lignans, including the cyclolignan 3,4'-dihydroxy-3',4'-dimethoxy-6,7'-cyclolignan (I), were isolated from the flowering tops of Larrea tridentata. Addnl. the flavanone, (S)-4',5-dihydroxy-7-methoxyflavanone, was isolated for the first time from L. tridentata or any member of the family Zygophyllaceae. All of the compds. were assessed for their growth inhibitory activity against human breast cancer, human colon cancer and human melanoma cell lines. The lignans had IC50 values of 5-60 μM with the linear butane-type lignans being the most potent, and it was found that colon cancer cells were the least sensitive cell type tested. The relative potency of linear butane type lignans against human breast cancer appears to correlate pos. with the no. of O-Me groups present on the mol.

Abstract

The State University of New Jersey, Piscataway, NJ, USA. Phytochemistry (Elsevier) (2005), 66(7), 811-815. Publisher: Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 143:4145 AN 2005:265701 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Spasmolytic flavonoids from Syzygium samarangense (Blume) Merr. & L.M. Perry. Amor, Evangeline C.; Villasenor, Irene M.; Ghayur, M. Nabeel; Gilani, Anwar H.; Choudhary, M. Iqbal. Institute of Chemistry, College of Science, University of the Philippines, Quezon City, Philippines. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2005), 60(1/2), 67-71. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 143:235636 AN 2005:223499 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two flavindogenides, 3-(2-chlorobenzylidene)-flavanone and 3-(2,4-dichlorobenzylidene)-flavanone reacted with six 5-substituted-2-aminobenzenethiols, the substituents being fluoro, chloro, bromo, Me, methoxy, and ethoxy, to give resp. 12 new compds., 10-substituted 7-(2-chlorophenyl/2,4-dichlorophenyl)-6H-6a,7-dihydro-6-phenyl[1]benzopyrano[3,4-c][1,5]benzothiazepines in 60-70% yields. The products were characterized on the basis of microanal. data for elements and IR, 1H, and 13C NMR and mass spectral studies. All the synthesized compds. were evaluated for their antimicrobial activity against the bacteria, Escherichia coli and GFC, and the fungi, Aspergillus niger, Aspergillus flavus, and Curvularia lunata.

Abstract

Syntheses of 1,5-benzothiazepines part XXXI: Syntheses and antimicrobial studies of 10-substituted 7-(monochlorophenyl/dichlorophenyl)-6H-6a,7-dihydro-6-phenyl[1]benzopyrano[3,4-c]-[1,5]benzothiazepines. Pant, Umesh C.; Dandia, A.; Chandra, Hem; Goyal, Shweta; Pant, Seema. Department of Chemistry, University of Rajasthan, Jaipur, India. Phosphorus, Sulfur and Silicon and the Related Elements (2005), 180(2), 559-571. Publisher: Taylor & Francis, Inc., CODEN: PSSLEC ISSN: 1042-6507. Journal written in English. CAN 143:422332 AN 2005:229725 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Satureja thymbra L. and Satureja spinosa L. are endemic plants of the Mediterranean region, characterized by a similar oregano-like smell. S. thymbra is restricted to the Central and East Mediterranean while S. spinosa is found in Crete, Samos and South West Anatolia. The qual. compn. of surface flavones of S. thymbra is very different from that of S. spinosa. Three out of five flavones of S. thymbra were 6-hydroxylated and two of them were 4'-methoxylated. S. spinosa, also contained, in addn. to 6-hydroxylated flavones, 6- and 8-methoxylated flavones, but no 4'-methoxyflavones. Regarding the quant. compn., it is notable that in both species flavanones and dihydroflavonols comprise more than 60% of the total surface flavonoid fraction. Apart from this similarity the surface flavonoid patterns of both species show that there are conspicuous differences at the infrageneric level.

Abstract

Surface flavonoids in Satureja thymbra and Satureja spinosa. Skoula, Melpomeni; Grayer, Renee J.; Kite, Geoffrey C. School of Plant Sciences, Reading, UK. Biochemical Systematics and Ecology (2005), 33(5), 541-544. Publisher: Elsevier B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 143:74827 AN 2005:234226 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The hexane ext. of Syzygium samarangense (Ss.Hex) dose-dependently (10-1000 μg/mL) relaxed the spontaneously contracting isolated rabbit jejunum. Four rare C-methylated flavonoids with a chalcone and a flavanone skeleton were isolated from Ss.Hex and were subsequently tested for spasmolytic activity. All flavonoids, identified as 2'-hydroxy-4',6'-dimethoxy-3'-methylchalcone (I), 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (II), 2',4'-dihydroxy-6'-methoxy-3'-methylchalcone (III), and 7-hydroxy-5-methoxy-6,8-dimethyl-flavanone (IV), showed dose-dependent spasmolytic activity in the rabbit jejunum with IC50 values of 148.3±69.4, 77.2±43.5, 142.4±58.6 and 178.5±37.5 μg/mL (mean ± SEM), resp. The dihydrochalcone deriv. of compd. I, 2'-hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone (V), when tested for spasmolytic activity, did not significantly relax the smooth muscle relative to the other compds. Verapamil, a std. spasmolytic, has an IC50 value of 0.16±0.04 μg/mL. This is the first report of the relaxant activity of chalcones, specifically of compds. I-III.


flavanone

Answer 648:

COCH 2

CH 2

Me

OMe

HO OMe

COCH

CH

Me

OMe

OMe

HO

O

O

Me

Me

OMe

HO

COCH

CH

Me

OH

OMe

HO

OMe

COCH

CH

Me

OH

OMe

HO

V

III

II

IV

I


flavanone

Expression profiling of the estrogen responsive genes in response to phytoestrogens using a customized DNA microarray. Ise, Ryota; Han, Dalho; Takahashi, Yusuke; Terasaka, Shunichi; Inoue, Akio; Tanji, Masao; Kiyama, Ryoiti. InfoGenes Co., Ltd., Tsukuba, Ibaraki, Japan. FEBS Letters (2005), 579(7), 1732-1740. Publisher: Elsevier B.V., CODEN: FEBLAL ISSN: 0014-5793. Journal written in English. CAN 142:367869 AN 2005:214219 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


From the fruits of Amorpha fruticosa L. (Leguminosae), a new natural compd. 6a,12a-dehydrosermundone along with 10 known compds. (8 flavonoids, 1 bibenzyl and 1 terpene) were isolated. The structure of the new natural compd. was elucidated on the basis of NMR spectroscopic technique.

Abstract

Pharmacognostical evaluation of arctii fructus (5). Chemical constituents from fruits of Amorpha fruticosa. Bai, Liping; Jiang, Hong; Kang, Tingguo; Zhang, Heming; Jiang, Zhihong; Zhao, Zhongzhen. Department of Chinese Medicines, Liaoning College of Traditional Chinese medicine, Shenyang, Peop. Rep. China. Natural Medicines (Tokyo, Japan) (2004), 58(6), 275-277. Publisher: Japanese Society of Pharmacognosy, CODEN: NMEDEO ISSN: 1340-3443. Journal written in English. CAN 143:372997 AN 2005:223100 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Four main flavanone glycosides (narirutin, hesperidin, naringin and neohesperidin) of Citrus fruits showed inhibitory activities on a compd. 48/80-induced histamine release from mast cells and a dinitrofluorobenzene (DNFB)-induced triphasic skin reaction. In order to examine seasonal variation of the content of flavanone glycosides exhibiting anti-allergic activity, seventeen kinds of Citrus fruits and two kinds of Fortunella fruits were periodically collected from early in July to early in Dec. at Yuasa exptl. farm of Kinki University. Their flavanone glycoside content was detd. by HPLC. Anti-allergic activity of the collected fruits was examd. by the compd. 48/80-induced histamine release assay. HPLC anal. of the collected Citrus fruits allowed us to assemble them into the following three groups; (1) a group of which main glycosides are narirutin and hesperidin having rutinoside moiety, such as Citrus unshiu, C. iyo, and C. sulcata: (2) a group of which main glycosides are naringin and neohesperidin having neohesperidoside moiety, such as C. daidai, C. hassaku, and C. natsudaidai: (3) a group of which main glycoside is naringin, such as C. grandis, C. naruto, and C. paradis. Any flavanone glycosides described above were not detected in Fortunella fruits. Anti-allergic activity of immature fruits was superior to that of mature ones in accordance with the fact that the content of four flavanone glycosides in immature fruits was higher than that in mature ones. On the basis of these findings, it is expected that immature Citrus fruits will be a medicinal resource for anti-allergic agents.

Abstract

Seasonal variation in anti-allergic activity of Citrus fruits and flavanone glycoside content. Kubo, Michinori; Fujita, Tadashi; Nishimura, Sachiyo; Tokunaga, Masashi; Matsuda, Hideaki; Gato, Takeshi; Tomohiro, Norimichi; Sasaki, Katsuaki; Utsunomiya, Naoki. School of Pharmaceutical Sciences, Kinki University, Higashiosaka, Osaka, Japan. Natural Medicines (Tokyo, Japan) (2004), 58(6), 284-294. Publisher: Japanese Society of Pharmacognosy, CODEN: NMEDEO ISSN: 1340-3443. Journal written in Japanese. CAN 143:225963 AN 2005:223102 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

All investigated synthetical analogs of flavonoids were practically nontoxic, and had anticytolytic and antioxidant activities in a model acute liver injury by tetrachloromethane. Among 27 investigated compds., 13 showed anticytolytic activity and 8 compds. antioxidant activity. Among the flavone derivs. with high hepatoprotective activity, compd. I showed high anticytolytic (45.7%) and antioxidant (60.9%) activity. In flavonol group with high membrane protective activity, compd. II had 42.7% anticytolytic activity and 72.2% antioxidant activity. All 6 flavanone had high anticytolytic activity (69.7-82.4%).

Abstract

Study of hepatoprotective activities of flavones, flavonols and flavanones in acute liver injury by tetrachloromethane. Misyuryova, S. V.; Zupanets, I. A.; Zhuravel, I. A.; Kovalyov, V. N.; Hylya, V. P. Nats. Farm. Univ., Ukraine. Visnik Farmatsii (2004), (3), 66-71. Publisher: Vidavnitstvo NFaU, CODEN: VFIAA2 ISSN: 1562-7241. Journal written in Ukrainian. CAN 143:39279 AN 2005:200041 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Compds. were isolated from D. trigonopus by silica gel, Sephadex LH-20 and RP-C18 column chromatog. and the structures were elucidated on the basis of spectroscopic methods. Nine compds. were isolated and identified as a lignan ((+)-syringaresinol); a fluorenone (dendroflorin); three bibenzyls (moscatilin, gigantol, tristin); a phenanthrene (moscatin); one flavanone (naringenin) and phytosterols (β-sitosterol and daucosterol). All the compds. were obtained from this plant for the first time.

Abstract

Chemical constituents of Dendrobium trigonopus. Zhang, Ting; Zhang, Chao-Feng; Wang, Zheng-Tao; Xu, Luo-Shan. Department of Pharmacognosy, China Pharmaceutical University, Nanjing, Peop. Rep. China. Zhongguo Tianran Yaowu (2005), 3(1), 28-30. Publisher: Zhongguo Tianran Yaowu Bianjibu, CODEN: ZTYHA7 ISSN: 1672-3651. Journal written in Chinese. CAN 143:435871 AN 2005:206406 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Here, we examd. phytoestrogens, isoflavones (genistein, daidzein, glycitein, biochanin A and ipriflavone), flavones (chrysin, luteolin and apigenin), flavonols (kaempferol and quercetin), and a coumestan, a flavanone and a chalcone (coumestrol, naringenin and phloretin, resp.) by means of a DNA microarray assay. A total of 172 estrogen responsive genes were monitored with a customized DNA microarray and their expression profiles for the above phytoestrogens were compared with that for 17β-estradiol (E2) using correlation coeffs., or R values, after a correlation anal. by linear regression. While R values indicate the similarity of the response by the genes, we also examd. the genes by cluster anal. and by their specificity to phytoestrogens (specific to genistein, daidzein or glycitein) or gene functions. Several genes were selected from p53-related genes (CDKN1A, TP53I11 and CDC14), Akt2-related genes (PRKCD, BRCA1, TRIB3 and APPL), mitogen-activated protein kinase-related genes (RSK and SH3BP5), Ras superfamily genes (RAP1GA1, RHOC and ARHGDIA) and AP-1 family and related genes (RIP140, FOS, ATF3, JUN and FRA2). We further examd. the exts. from two local crops of soy beans (Kuro-daizu or Mochi-daizu) by comparing the gene expression profiles with those of E2 or phytoestrogens as a first step in utilizing the expression profiles for various applications.

Abstract


flavanone


Promoter and expression cassettes for bidirectional gene expression in transgenic non-human cells and organisms. Heim, Ute; Herbers, Karin; Kunze, Irene. (Sungene GmbH & Co. Kgaa, Germany). PCT Int. Appl. (2005), 62 pp. CODEN: PIXXD2 WO 2005019459 A1 20050303 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in German. Application: WO 2004-EP7255 20040703. Priority: DE 2003-10333479 20030722. CAN 142:274984 AN 2005:182837 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Selenoflavanone and Flavanone derivs. have been synthesized and evaluated for neuroprotection activity. Heterocyclic compds. with oxygen atoms are known to possess potent biol. effects. The flavonoids, isoflavonoids, and coumarins which form the bulk of these compds. are quite polar and have limited use as drugs that pass through membranes. The non-polar property is increased by substituting oxygen with selenium in the heterocyclic compd. Our group focused on synthesizing selenoheterocyclic compds. with more non-polar properties. In the Selenoflavanone treated group, the anterior and medial parts of the striatum, and large areas of the cortex, remained unaffected compared with the control group. The total infarction vols. in the ipsilateral hemisphere of ischemia-reperfusion mouse were significantly reduced by Selenoflavanone treatment.

Abstract

Synthesis and in vivo evaluation of Selenoflavanone: A new class of neuroprotective agent. Kim, Dong-myung; Ryu, Jong-Hoon; Jeong, Jin-Hyun. College of Pharmacy, Kyung Hee University, Seoul, S. Korea. Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, United States, March 13-17, 2005 (2005), MEDI-201. Publisher: American Chemical Society, Washington, D. C CODEN: 69GQMP Conference; Meeting Abstract written in English. AN 2005:191534 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

O

O

OH

O

O

MeO

O

CO 2H

III


flavanone

Phytoestrogens have been explored as promising next generation estrogenic drug candidates with min. cardiovascular risks. Investigating spatial, electronic and topol. properties of the mols., structure-activity relationships were drawn in an endeavor to find out the basic pharmacophore features of flavonoids for binding with the estrogen receptor. Implementing multi-parameter linear regression

Abstract

QSAR modeling on binding affinity of diverse estrogenic flavonoids: electronic, topological and spatial functions in quantitative approximation. Mukherjee, Subhendu; Mukherjee, Arup; Saha, Achintya. Department of Chemical Technology, University of Calcutta, Kolkata, India. THEOCHEM (2005), 715(1-3), 85-90. Publisher: Elsevier B.V., CODEN: THEODJ ISSN: 0166-1280. Journal written in English. CAN 142:423036 AN 2005:178780 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention relates to transgenic expression cassettes for the expression of two genes in transgenic non-human cells or organisms, esp. plant cells and plants. Said cassettes comprise the bidirectional promoter of Arabidopsis thaliana found between the ferridoxin and cysteine synthase genes, or functional equiv. of this promoter. Expression vectors contg. such cassettes and transgenic non-human organisms expressing the cassettes are also disclosed. The transgenic organisms may be used to prep. food and feed, drugs, and fine chems. Thus, the expression of two selectable markers from the bidirectional promoter in tobacco and rape was demonstrated. The genes were expressed in the green tissues, not in flowers or roots. In tobacco, but not in rape, the genes were also expressed in the pollen.

Abstract WO 2004-EP7255 W 20040703DE 2003-10333479 A 20030722Priority Application US 20060150282 A1 20060706 US 2006-565221 20060228 ES 2289529 T3 20080201 ES 2004-740603 20040703AT 368121 T 20070815 AT 2004-740603 20040703

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, FI, RO, CY, TR, BG, CZ, EE, HU, PL, SK

EP 1711612 B1 20070725EP 1711612 A1 20061018 EP 2004-740603 20040703CA 2532903 A1 20050303 CA 2004-2532903 20040703AU 2004267161 A1 20050303 AU 2004-267161 20040703



WO 2005019459 A1 20050303 WO 2004-EP7255 20040703


flavanone

To specify the genotypic variation of Mediterranean Citrus juices, the contents of carotenoids, flavonoids, and vitamin C were detd. by high-performance liq. chromatog. A selection of orange varieties and Mandarin species from the Mediterranean area (Citrus sinensis, Citrus deliciosa Ten, and Citrus clementina Hort. ex Tan) was evaluated using carotenoid profiles and flavanones contents. Among the eight varieties of orange (Salustiana, Hamlin, Shamouti, Pera, Valencia, Maltaise, Sanguinelli, and Cara-cara) and two Mandarin species, only three cultivars (Pera, Sanguinelli, and Shamouti) and the two Mandarin species displayed a high content of vitamin A (374, 381, and 272 ER L-1 for the three orange cultivars and 1156 and 960 retinol equiv. (RE) L-1 for the Mandarins) due to a high content of β-cryptoxanthin. These same Citrus were also rich in hesperidin (502, 537, 552, 767, and 754 mg L-1, resp.). Principal component anal. allowed the Mediterranean orange varieties and Mandarin species to be differentiated on the basis of nutritional criteria. Strong correlations were obsd. between β-cryptoxanthin and hesperidin (r = 0.92) and between β-cryptoxanthin and β-carotene (r = 0.98). In contrast, vitamin C content was not correlated with carotenoids and flavanone glycosides. The Mandarin and orange

Abstract

Varietal and interspecific influence on micronutrient contents in citrus from the Mediterranean area. Dhuique-Mayer, Claudie; Caris-Veyrat, Catherine; Ollitrault, Patrick; Curk, Franck; Amiot, Marie-Josephe. Departement FLHOR, Centre de Cooperation Internationale en Recherche Agronomique pour le Developpement (CIRAD), Montpellier, Fr. Journal of Agricultural and Food Chemistry (2005), 53(6), 2140-2145. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 142:409998 AN 2005:172665 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Quinone reductase 2 is a mammalian cytosolic FAD-dependent enzyme, the activity of which is not supported by conventional nicotinamide nucleotides. An endobiotic substrate has never been reported for this enzyme nor a set of mol. tools, such as inhibitors. In the present work, we used the recombinant human enzyme, expressed in CHO cells for the systematic screening of both co-substrates and substrates. The co-substrates survey showed that the natural occurring compd., N-ribosylnicotinamide, was a poor co-substrate. The synthetic N-benzylnicotinamide is a better one compared to any other compds. tested. We found that tetrahydrofolic acid acted as a co-substrate for the redn. of menadione catalyzed by quinone reductase 2, although with poor potency (Km .apprx. 2 mM). Among a series of com. available quinones, a single one was found to be substrate of quinone reductase 2, in the presence of N-benzyldihydronicotinamide: coenzyme Q0. Finally, we tested a series of 197 flavonoids as potential inhibitors. We found apigenin, genistein or kaempferol as good inhibitor of quinone reductase 2 activity with IC50 in the 100 nM range. These compds., co-substrate, substrate and inhibitors will permit to better know this enzyme, the role of which is still poorly understood.

Abstract

Quinone reductase 2 substrate specificity and inhibition pharmacology. Boutin, Jean A.; Chatelain-Egger, Florence; Vella, Fanny; Delagrange, Philippe; Ferry, Gilles. Pharmacologie Moleculaire et Cellulaire, Institut de Recherches Servier, Croissy-sur-Seine, Fr. Chemico-Biological Interactions (2005), 151(3), 213-228. Publisher: Elsevier Ireland Ltd., CODEN: CBINA8 ISSN: 0009-2797. Journal written in English. CAN 143:301200 AN 2005:174051 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


anal., a significant relationship (R2=0.892 and Q2=0.805 for n=19) was established that explained 86.097% variance in binding affinity to the receptor. This study revealed the importance of partial charges at atoms C2' and C4' in the Ph ring C, electrotoplogical state of atom C7 in the Ph ring A and the mol. orientation and conformational stringency factors. It has been found that substitution by an e- donating group in the Ph ring at C2', e- withdrawing groups at C4' and C7 of the mol. in conjunction with minimal conformational rigidity could be important for estrogenic activity.


flavanone

This study examd. the passive cutaneous anaphylaxis-inhibitory activity of the flavanones isolated from the pericarp of Citrus unshiu (Family Rutaceae) and the fruit of Poncirus trifoliata (Family Rutaceae). Naringenin, hesperetin and ponciretin potently inhibited IgE-induced β-hexosaminidase release from RBL-2H3 cells and the PCA reaction. Among the flavanones examd., naringenin was the most potent with an IC50 value for β-hexosaminidase release from RBL-2H3 cells of 0.029 mM. I.p. administered naringenin (5 mg/kg) inhibited PCA by 70±1.7%, compared with the control group. The inhibitory activity of naringenin was found to be comparable to that of azelastine, which is a com. available antiallergic drug. However, their glycosides, hesperidin, naringin and poncirin, did not inhibit the in vitro release of β-hexosaminidase from the RBL-2H3 cells. On the other hand, these flavanones did not improve the oxazolone-induced dermatitis in the mouse ears. When the flavanone glycosides were administered to rats, the aglycons, but not the

Abstract

Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata. Park, Sung-Hwan; Park, Eun-Kyung; Kim, Dong-Hyun. Department of Food and Nutrition, College of Pharmacy, Kyung Hee University, Seoul, S. Korea. Planta Medica (2005), 71(1), 24-27. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 142:385421 AN 2005:156811 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

HO

HO OH

OH

MeMe

Me

I

A novel prenylated flavanone was isolated from Et acetate exts. of the hard-wood cutting root of Kinuyutaka, a cultivar of Morus alba. The structure, 7,2',4',6'-tetrahydoroxy-6-geranylflavanone (I), was revealed by spectral analyses. I exhibited cytotoxic activity against rat hepatoma (dRLh84) cells with an IC50 of 52.8 μg/mL.

Abstract

A novel cytotoxic prenylated flavonoid from the root of Morus alba. Kofujita, Hisayoshi; Yaguchi, Masashi; Doi, Norio; Suzuki, Koichi. Faculty of Agriculture, Iwate University, Morioka, Japan. Journal of Insect Biotechnology and Sericology (2004), 73(3), 113-116. Publisher: Japanese Society of Sericultural Science, CODEN: JIBSBD ISSN: 1346-8073. Journal written in English. CAN 143:263452 AN 2005:162611 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


group was quite distinct. The orange varieties could be divided in two groups. In addn., a diversity tree allowed a genetic approach to differentiating Citrus cultivars on the basis of Euclidean distances. This representation showed that the hybrid Clementine was nearer to its parent Mandarin than to its parent orange, suggesting that β-cryptoxanthin was a dominant genetic factor. With regard to vitamin A, Mandarin and its hybrid Clementine appeared to be the best Citrus species.


flavanone

O O

O

MeMe

Me

OH

HO

HO

O

O

HO OMe

CH 2 CH C Me

Me

HO

OH

CH 2CHCMe

Me

O

O

HO OH

CH 2 CH C Me

Me

HO

OH

CH 2CHCMe

Me

I

III

II

Further phytochem. investigation on the roots of Cudrania tricuspidata afforded a new isoprenylated xanthone, cudratricusxanthone I (I), two new isoprenylated flavanones, cudraflavanones C and D (II and III, resp.), and seven known compds., 1,7-dihydroxy-3,6-dimethoxyxanthone, macluraxanthone C, cudraxanthones E, K, and L, cudraflavanone A, and cudraflavone C. Their structures were identified by spectroscopic methods. Cudratricusxanthone H, macluraxanthone B, two xanthones previously isolated from this plant, and macluraxanthone C, showed significant inhibitory effects on four kinds of human digestive app. tumor cell lines (HCT-116, SMMC-7721, SGC-7901, and BGC-823) with IC50 values of 2.70-12.66 μM.

Abstract

Isoprenylated xanthones and flavonoids from Cudrania tricuspidata. Zou, Ying-Shu; Hou, Ai-Jun; Zhu, Guo-Fu. Department of Pharmacognosy, School of Pharmacy, Fudan University, Shanghai, Peop. Rep. China. Chemistry & Biodiversity (2005), 2(1), 131-138. Publisher: Verlag Helvetica Chimica Acta AG, CODEN: CBHIAM ISSN: 1612-1872. Journal written in English. CAN 143:56611 AN 2005:142086 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone glycosides, were excreted in urine. This suggests that the flavanone glycosides can be activated by intestinal bacteria, and may be effective toward IgE-induced atopic allergies.


flavanone

Myricetin inhibits matrix metalloproteinase 2 protein expression and enzyme activity in colorectal carcinoma cells. Ko, Ching-Huai; Shen, Shing-Chuan; Lee, Tony J. F.; Chen, Yen-Chou. Graduate Institutes of Pharmaceutical Sciences and Pharmacognosy, School of Pharmacy and Department of Dermatology, School of Medicine, Taipei Medical University, Taipei, Taiwan. Molecular Cancer Therapeutics (2005), 4(2), 281-290. Publisher: American Association for Cancer Research, CODEN: MCTOCF ISSN: 1535-7163. Journal written in English. CAN 142:423230 AN 2005:133801 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effect of naringenin (NAR), a naturally occurring citrus flavanone, on the acute nephrotoxicity produced by cisplatin (7 mg/kg, i.v.) was investigated in the rat. Oral administration of NAR (20 mg/kg/day) for 10 days, starting 5 days before cisplatin single i.v. injection, produced significant protection of renal function. NAR reduced the extent of cisplatin-induced nephrotoxicity, as evidenced by significant redn. in serum urea and creatinine concns., decreased polyuria, redn. in body wt. loss, marked redn. in urinary fractional sodium excretion and glutathione S-transferase (GST) activity, and increased creatinine clearance. Cisplatin-induced alterations in renal cortex lipid peroxides and GST activity were markedly improved by NAR. Cisplatin-induced alterations in renal cortex antioxidant defense system were greatly prevented by NAR. In cisplatin-NAR combined treatment group, antioxidant enzymes namely superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), and catalase (CAT) were significantly increased to 54.5, 30.3 and 35.6%, resp. compared to cisplatin treated group. Platinum renal content was not affected by NAR treatment. The results provide further insight into the mechanisms of cisplatin-induced nephrotoxicity and confirm the antioxidant potential of NAR.

Abstract

Naringenin attenuates cisplatin nephrotoxicity in rats. Badary, Osama A.; Abdel-Maksoud, Sahar; Ahmed, Wafaa A.; Owieda, Gehan H. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Helwan University, Cairo, Ain Helwan, Egypt. Life Sciences (2005), 76(18), 2125-2135. Publisher: Elsevier B.V., CODEN: LIFSAK ISSN: 0024-3205. Journal written in English. CAN 142:329424 AN 2005:135235 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. The plant genus Baccharis has >500 species growing mainly in the tropical areas of South America. Many of them are extensively used in folk medicine in the treatment or prevention of anemias, inflammations, diabetes mellitus, and stomach, liver and prostate diseases. Phytochem. and biol. investigations of .apprx.120 species led to the isolation numerous flavones, flavanones, diterpenes, and triterpenes. Among them are several clerodane and labdane diterpenes and flavonoid aglycons, with the flavone moiety being the most frequent.

Abstract

The Baccharis genus (Asteraceae): Chemical, economical and biological aspects. Verdi, Luiz Gonzaga; Brighente, Ines Maria Costa; Pizzolatti, Moacir Geraldo. Departamento de Quimica, Universidade Federal de Santa Catarina, Florianopolis-SC, Brazil. Quimica Nova (2005), 28(1), 85-94. Publisher: Sociedade Brasileira de Quimica, CODEN: QUNODK ISSN: 0100-4042. Journal; General Review written in Portuguese. CAN 143:263431 AN 2005:139257 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus. Ogata, Jun; Itoh, Yoshio; Ishida, Madoka; Yoshida, Hiroyuki; Ozeki, Yoshihiro. Department of Biotechnology, Faculty of Technology, Tokyo University of Agriculture and Technology, Tokyo, Japan. Plant Biotechnology (Tokyo, Japan) (2004), 21(5), 367-375. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 143:110338 AN 2005:126707 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Bioassay-guided fractionation of an ethanol ext. of a Madagascar collection of Schizolaena hystrix afforded three new flavanones, schizolaenone A (1), schizolaenone B (2), and 4'-O-methylbonannione A (3), as well as three known flavanones, nymphaeol A, bonannione A, and macarangaflavanone B, and the flavanol bonanniol A. The structures of compds. 1-3 were detd. by various one- and two-dimensional NMR techniques. All of the isolates were tested for cytotoxicity against the A2780 human ovarian cancer cell line. Nymphaeol A (IC50 = 5.5 μg/mL) exhibited the greatest cytotoxicity, while the other flavanones were found to be only weakly active.

Abstract

Cytotoxic flavanones of Schizolaena hystrix from the Madagascar rainforest. Murphy, Brian T.; Cao, Shugeng; Norris, Andrew; Miller, James S.; Ratovoson, Fidisoa; Andriantsiferana, Rabodo; Rasamison, Vincent E.; Kingston, David G. I. Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA, USA. Journal of Natural Products (2005), 68(3), 417-419. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 142:370747 AN 2005:128135 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Results of the present study indicate that myricetin significantly blocked both endogenous and TPA-induced MMP-2 enzyme activity by inhibiting its protein expression and enzyme activity. The blockade involved suppression of PKC translocation, ERK phosphorylation, and c-Jun protein expression.

Colorectal carcinoma is a leading cause of human mortality due to its high metastatic ability. Because the activation of matrix metalloproteinases (MMP) is a key factor in the metastatic process, agents with the ability to inhibit MMP activity have potential in the treatment of colorectal carcinoma. In the present study, among 36 flavonoids examd., myricetin was found to be the most potent inhibitor of MMP-2 enzyme activity in COLO 205 cells (IC50 = 7.82 μmol/L). Myricetin inhibition of MMP-2 enzyme activity was also found in the human colorectal carcinoma cell lines COLO 320HSR, COLO 320DM, HT 29, and COLO 205-X (IC50 = 11.18, 11.56, 13.25, and 23.51 μmol/L, resp.). In contrast, no inhibitory effect of MMP-2 protein expression or enzyme activity was obsd. in myricitrin (myricetin-3-rhamnoside)-treated cells. In 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated COLO 205 cells, an increase in MMP-2 protein expression and enzyme activity, as well as of protein kinase C (PKC) α protein translocation, extracellular signal-regulated kinase (ERK) 1/2 protein phosphorylation, and c-Jun protein expression was obsd. ERK inhibitor (PD98059) and PKC inhibitors (GF-109203X and H-7), but not p38 inhibitor (SB203580) or c-jun-NH2-kinase inhibitor (SP600125), significantly inhibited TPA-induced MMP-2 protein expression, with reduced ERK phosphorylation and c-Jun protein expression. Addn. of myricetin but not myricitrin suppressed TPA-induced MMP-2 protein expression in COLO 205 cells by blocking the TPA-induced events, including translocation of PKCα from cytosol to membrane, phosphorylation of ERK1/2 protein, and induction of c-Jun protein expression. Addn. of PD98059 or GF-109203X significantly enhanced the inhibitory effect of myricetin on MMP-2 enzyme activity induced by TPA. Furthermore, myricetin, but not myricitrin, suppressed TPA-induced invasion of COLO 205 cells in an in vitro invasion assay using Engelbreth-Holm-Swarm sarcoma tumor ext. Matrigel-coated Transwells.

Abstract


flavanone

The relative threshold dissocn. energies of flavonoid/transition metal/auxiliary ligand complexes [MII (flavonoid - H) auxiliary ligand]+ formed by electrospray ionization (ESI) were measured by energy-variable collisionally activated dissocn. (CAD) in a quadrupole ion trap (QIT). For each of the isomeric flavonoid diglycoside pairs, the rutinoside (with a 1-6 inter-saccharide linkage) requires a greater CAD energy and thus has a higher dissocn. threshold than its neohesperidoside (with a 1-2 inter-saccharide linkage) isomer. Likewise, the threshold energies of complexes contg. flavones are higher than those contg. flavanones. The monoglycoside isomers have characteristic threshold energies. The flavonoids that are glycosylated at the 3-O- position tend to have lower threshold energies than

Abstract

Threshold dissociation and molecular modeling of transition metal complexes of flavonoids. Zhang, Junmei; Brodbelt, Jennifer S.; Wang, Junmei. Department of Chemistry and Biochemistry, University of Texas, Austin, TX, USA. Journal of the American Society for Mass Spectrometry (2005), 16(2), 139-151. Publisher: Elsevier Inc., CODEN: JAMSEF ISSN: 1044-0305. Journal written in English. CAN 142:381475 AN 2005:124951 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Cultured cells of Sophora flavescens produce (2S)-naringenin-derived prenylated flavanone sophoraflavanone G and liquiritigenin-derived trifolirhizin 6'-O-malonate. The regulation of flavonoid biosynthesis was examd. by analyzing the metabolites produced in the cultured cells fed (2RS)-naringenin. The amt. of sophoraflavanone G in cells fed 0.1 or 0.3 mM (2RS)-naringenin was two-fold that in control cells, although the conversion ratio was only 5 to 10% of the administered (2S)-naringenin. On the other hand, (2R)-naringenin, which does not occur naturally, was efficiently converted into its 4',7-di-O-β-D-glucoside. (2S)-Naringenin prenylation activity was higher at the logarithmic growth stage. The cells fed (2RS)-naringenin at a lower concn. (below 0.1 mM), accumulated sophoraflavanone G as the main prenylated flavanone. In contrast, cells fed 0.3 mM (2RS)-naringenin accumulated 8-prenylnaringenin and leachianone G, intermediates of sophoraflavanone G in large amts. Accumulation of trifolirhizin 6'-O-malonate was suppressed by the addn. of naringenin.

Abstract

Metabolism of administered (2RS)-naringenin in flavonoid-producing cultured cells of Sophora flavescens. Yamamoto, Hirobumi; Kuribayashi, Hiroki; Seshima, Yasuharu; Zhao, Ping; Kouno, Isao; Taguchi, Goro; Shimomura, Koichiro. Plant Regulation Research Center, Faculty of Life Sciences, Toyo University, Gunma, Japan. Plant Biotechnology (Tokyo, Japan) (2004), 21(5), 355-359. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 143:189980 AN 2005:126705 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Yellow petals of carnations contain chalcone 2'-O-glucoside. The glucosylation occurs after the p-coumaroyl CoA and malonyl-CoA condensation reaction by chalcone synthase (CHS), but the enzyme(s) transferring glucose from UDP-glucose to the 2'-OH position of chalcone has not been identified. The full-length cDNA clones for 18 glucosyltransferase (GT) genes were isolated from petal tissue of carnation (Dianthus caryophyllus) bearing various flower colors. The 18 GTs encoded in the cDNAs were enzymically characterized in an E. coli expression system using chalcone, flavanone, flavone, flavonol and anthocyanidin as substrates. Three of the 18 were characterized as 3-GT possessing different substrate specificities for flavonoids and anthocyanidin and another two GTs catalyzed the transfer of glucose to the 2'-hydroxyl group of chalcone. In addn., these two enzymes glucosylated flavonol (3-OH and 7-OH), flavanone (7-OH), flavone (7-OH) and anthocyanidin (3-OH and 7-OH).

Abstract


flavanone

A new flavanone with epoxy-isopentyl moiety named parkintin (I) has been isolated from the methanol sol. part of Parkinsonia aculeata Linn. belonging to the family Caesalpiniaceae. The structure of parkintin has been established with the aid of spectroscopic techniques including COSY and HMBC expts.

Abstract

Parkintin: a new flavanone with epoxy-isopentyl moiety from Parkinsonia aculeata Linn. (Caesalpiniaceae). Ali, Muhammad Shaiq; Ahmed, Farman; Pervez, Muhammad Kashif; Azhar, Iqbal; Ibrahim, Syed Amir. H.E.J. Research Institute of Chemistry, University of Karachi, Karachi, Pak. Natural Product Research (2005), 19(1), 53-56. Publisher: Taylor & Francis Ltd., CODEN: NPRAAT ISSN: 1478-6419. Journal written in English. CAN 142:407613 AN 2005:121909 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The tyrosinase inhibitory activity of methanol exts. of the leaves of 39 plant species growing on the seashore of Iriomote island (Okinawa, Japan) was investigated. The exts. of Hibiscus tiliaceus, Carex pumila, and Garcinia subelliptica showed potent activity among them. The inhibitors in the ext. of Garcinia subelliptica were purified by assay-guided fractionation to give two biflavonoids. These were known compds. (2R,3S-5,7,4',5'',7'',3''',4'''-heptahydroxy flavanone[3-8''] flavone and 5,7,4',5'',7'',3''',4'''-heptahydroxy[3-8''] biflavanone), although their strong inhibitory activity toward tyrosinase is revealed for the first time in this work. One of these biflavonoids (2R,3S-5,7,4',5'',7'',3''',4'''-heptahydroxy flavanone[3-8''] flavone) showed much stronger activity (IC50 2.5 μM) than that of kojic acid (IC50 9.1 μM) when L-tyrosine was used as the substrate.

Abstract

Screening for tyrosinase inhibitors among extracts of seashore plants and identification of potent inhibitors from Garcinia subelliptica. Masuda, Toshiya; Yamashita, Daiki; Takeda, Yoshio; Yonemori, Shigetomo. Faculty of Integrated Arts and Sciences, University of Tokushima, Tokushima, Japan. Bioscience, Biotechnology, and Biochemistry (2005), 69(1), 197-201. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 143:56604 AN 2005:124095 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


those glycosylated at the 7-O- or 4'-O- position, and those that are C- bonded have lower threshold energies than the O- bonded isomers. The structural features that substantially influence the threshold energies include the aglycon type (flavanone vs. flavone), the type of disaccharide (rutinose vs. neohesperidose), and the linkage type (O- bonded vs. C- bonded). Various computational means were applied to probe the structures and conformations of the complexes and to rationalize the differences in threshold energies of isomeric flavonoids. The most favorable coordination geometry of the complexes has a plane-angle of .apprx.62°, which means that the deprotonated flavonoid and 2,2'-bipyridine within a complex do not reside on the same plane. Stable conformations of 5 Co complexes and 5 deprotonated flavonoids were identified. The conformations were combined with the point charges and He accessible surface areas to explain qual. the differences in threshold energies for isomeric flavonoids.


flavanone

Oxidative stress contributes to cellular injury following clin. and exptl. ischemia/reperfusion episodes. Oxidative injury can induce cellular and subcellular damage that results in apoptotic cell death. We tested whether 2',4',7-trihydroxyflavanone, a synthetic

Abstract

Inhibition of hydrogen peroxide-induced endothelial apoptosis by 2',4',7-trihydroxyflavanone, a flavonoid form. Choi, Yean-Jung; Lee, Myung-Kyu; Lee, Yong-Jin; Jeong, Yu-Jin; Park, Jung Han Yoon; Lim, Soon Sung; Kang, Young-Hee. Division of Life Sciences, Hallym University, Chuncheon, S. Korea. Journal of Medicinal Food (2004), 7(4), 408-416. Publisher: Mary Ann Liebert, Inc., CODEN: JMFOFJ ISSN: 1096-620X. Journal written in English. CAN 142:367560 AN 2005:107489 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


To investigate the nature of mutations induced by accelerated ions in higher plants, the effects of carbon-ion-irradn. were compared with those of electron-irradn. in Arabidopsis thaliana. Point-like mutations and rearrangements were induced at a similar frequency after carbon-ion-irradn., whereas point-like mutations were more frequently induced after electron-irradn. Sequence anal. revealed that carbon-ion-induced point-like mutations were mostly short deletions. In the case of rearrangements, deletions, inversions, insertions, and translocations were found. The estd. frequency of deletion induction was comparable to that of fast neutrons. Anal. of chromosome breakpoints revealed that carbon ions frequently deleted small regions around the breakpoints, whereas electron-irradn. often duplicated these regions. Moreover, for both types of radiation, broken ends with microhomologies were frequently rejoined. Results of the breakpoint and broken end analyses suggest that non-homologous end-joining (NHEJ) leads to the rejoining of double strand breaks (dsbs) after cells are exposed to both types of radiation, but the type of NHEJ that occurs as a result of damage is different. The results indicated that carbon-ion-induced mutations are most likely nulls and that the induced rearrangements may arise through a unique mechanism. These findings indicate that accelerated ions are a useful mutagen for both forward and reverse genetics for plants.

Abstract

Analysis of mutations induced by carbon ions in Arabidopsis thaliana. Shikazono, Naoya; Suzuki, Chihiro; Kitamura, Satoshi; Watanabe, Hiroshi; Tano, Shigemitsu; Tanaka, Atsushi. Department of Ion Beam Applied Biology, Japan Atomic Energy Research Institute (JAERI), Takasaki, Gunma, Japan. Journal of Experimental Botany (2005), 56(412), 587-596. Publisher: Oxford University Press, CODEN: JEBOA6 ISSN: 0022-0957. Journal written in English. CAN 143:20638 AN 2005:109886 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

CH 2O

Me

Me

H

I


flavanone

For detection and differentiation of isomeric flavonoids, electrospray ionization mass spectrometry is used to generate silver complexes of the type (Ag + flavonoid)+. Collisionally activated dissocn. (CAD) of the resulting 1:1 silver/flavonoid complexes allows isomer differentiation of flavonoids. Eighteen flavonoid diglycosides constituting seven isomeric series are distinguishable from each other based on the CAD patterns of their silver complexes. Characteristic dissocn. pathways allow identification of the site of glycosylation, the type of disaccharide (rutinose vs. neohesperidose), and the type of aglycon (flavonol vs. flavone vs. flavanone). This silver complexation method is more universal than previous metal complexation methods, as intense silver complexes are obsd. even for flavonoids that lack the typical metal chelation sites. To demonstrate the feasibility of using silver complexation and tandem mass spectrometry to characterize flavonoids in complex mixts., flavonoids extd. from grapefruit juice are sepd. by high-performance liq. chromatog. and analyzed via a postcolumn complexation ESI-MS/MS strategy. Diagnostic fragmentation pathways of the silver

Abstract

Silver complexation and tandem mass spectrometry for differentiation of isomeric flavonoid diglycosides. Zhang, Junmei; Brodbelt, Jennifer S. Department of Chemistry and Biochemistry, University of Texas, Austin, TX, USA. Analytical Chemistry (2005), 77(6), 1761-1770. Publisher: American Chemical Society, CODEN: ANCHAM ISSN: 0003-2700. Journal written in English. CAN 142:335137 AN 2005:96667 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Methanolic leaf exts. of Erythroxylum australe produced eight O-conjugated flavonoids. Six of the flavonoid aglycons were dihydroisoflavones (all dihydroorobol derivs.), one a flavanone, eriodictyol, and one a flavonol, quercetin. The major glycosides of the flavonoids included mono-glucosyl-rhamnosyls and dirhamnosyl-glucosides with either 3,5,7 or 3',4' linkage or a combination thereof. The array of flavonoids present in E. australe suggests kinship to E. ulei and linkage to the four cultivated alkaloid-bearing Erythroxylum, esp. the ancestral E. coca var. coca. Because of the uniqueness of the flavonoids present in leaf tissue of E. australe they are unambiguously useful as chemotaxonomic markers for the taxon.

Abstract

Flavonoids as chemotaxonomic markers for Erythroxylum australe. Johnson, Emanuel L.; Schmidt, Walter F. USDA ARS Weed Science Laboratory, Beltsville, MD, USA. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2004), 59(11/12), 769-776. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 142:460087 AN 2005:101678 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavonoid deriv., inhibits hydrogen peroxide (H2O2)-induced toxicity in human umbilical endothelial cells (HUVECs). Cultured HUVECs were incubated for 30 min with 0.2 mM H2O2 in the absence and presence of 2',4',7-trihydroxyflavanone at a non-toxic concn. of 50 μM. The effect of 2',4',7-trihydroxyflavanone on apoptosis parameters was compared with that of naringenin and two flavonol derivs., 2',4',7-trihydroxyflavonol and 2',4',6-trihydroxyflavonol. H2O2 induced cell death within 24 h over the range of 0.05-1.0 mM, and decreased cell viability by .apprx.30% at 0.2 mM. This cytotoxicity was assocd. with nuclear condensation and DNA fragmentation, indicating induction of apoptosis. 2',4',7-Trihydroxyflavanone, as well as naringenin, was effective as an inhibitor of oxidative stress, protecting cell viability with ≥85% viable cells compared with the control, and no apparent nuclear condensation or DNA fragmentation. In contrast, the flavonol derivs. had no such effect. In addn., immunocytochem. data and Western blot anal. revealed that, unlike flavonol derivs., the expression of Bcl-2 was markedly up-regulated, and that the expression of Bax and activation of caspase-3 were strongly inhibited by this flavanone deriv., thereby implicating antioxidant activity-related anti-apoptotic mechanisms of 2',4',7-trihydroxyflavanone. These results indicate that the synthetic flavonoid deriv. 2',4',7-trihydroxyflavanone is an effective antioxidant, preventing endothelial apoptosis induced by H2O2.


flavanone

It is an objective of our institution to establish a virtual lab. allowing for a reliable in silico estn. of the harmful effects triggered by drugs, chems. and their metabolites. In the recent past, we have developed the underlying technol. (Multi-dimensional QSAR: Quasar and Raptor) and compiled a pilot system including the 3D models of three receptors known to mediate endocrine-disrupting effects (the aryl hydrocarbon receptor, the estrogen receptor and the androgen receptor, resp.) and validated them against 310 compds. (drugs, chems., toxins). Within this set up we could demonstrate that our concepts are able to both recognize toxic compds. substantially

Abstract

In silico prediction of receptor-mediated environmental toxic phenomena - Application to endocrine disruption. Lill, M. A.; Dobler, M.; Vedani, A. Biographics Laboratory 3R, Basel, Switz. SAR and QSAR in Environmental Research (2005), 16(1-2), 149-169. Publisher: Taylor & Francis Ltd., CODEN: SQERED ISSN: 1062-936X. Journal written in English. CAN 143:21052 AN 2005:88952 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A quant. structure-antioxidant activity relationship (QSAR) study of 36 flavonoids was performed using the partial least squares projection of latent structures (PLS) method. The chem. structures of the flavonoids have been characterized by constitutional descriptors, two-dimensional topol. and connectivity indexes. Our PLS model gave a proper description and a suitable prediction of the antioxidant activities of a diverse set of flavonoids having clustering tendency.

Abstract

Quantitative structure-antioxidant activity relationships of flavonoid compounds. Farkas, Orsolya; Jakus, Judit; Heberger, Karoly. Bio-oxidation Group, Chemical Research Center, Hungarian Academy of Sciences, Budapest, Hung. Molecules (2004), 9(12), 1079-1088. Publisher: Molecular Diversity Preservation International, CODEN: MOLEFW ISSN: 1420-3049. http://www.mdpi.org/molecules/papers/91201079.pdf Journal; Online Computer File written in English. CAN 142:348110 AN 2005:93162 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Maximaflavanone-A, {4,6-γ,γ-dimethylallyl-2",2"-dimethylpyrano(6",5":7,8)flavanone} along with its flavone deriv. were synthesized. The synthesized compds. were characterized using UV, IR and 1H NMR spectral data.

Abstract

Synthesis of maximaflavanone-A and its derivative. Alam, Sayed; Islam, Azizul; Das, Naresh Chandra. Department of Chemistry, Bangladesh Institute of Technology, Rajshahi, Bangladesh. Journal of Bangladesh Academy of Sciences (2004), 28(2), 117-120. Publisher: Bangladesh Academy of Sciences, CODEN: JBACDF ISSN: 0378-8121. Journal written in English. CAN 143:367104 AN 2005:95098 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


complexes of the individual eluting flavonoids allow successful identification of the six flavonoids in the ext.


flavanone


Flavonoids including the aglycons, hesperetin (HT; 5,7,3'-trihydroxy-4'-methoxy-flavanone), and naringenin (NE; 5,7,4'-trihydroxy flavanone) and glycones, hesperidin (HD; 5,7,3'-trihydroxy-4'-methoxy-flavanone 7-rhamnoglucoside) and naringin (NI; 5,7,4'-trihydroxy flavanone 7-rhamnoglucoside), were used to examine the importance of rutinose at C7 on the inhibitory effects of flavonoids on lipopolysaccharide (LPS)-induced nitric oxide prodn. in macrophages. Both HT and NE, but not their resp. glycosides HD and NI, induced heme oxygenase 1 (HO-1) protein expression in the presence or absence of LPS and showed time and dose-dependent inhibition of LPS-induced nitric oxide (NO) prodn. and inducible nitric oxide synthase (iNOS) expression in RAW264.7, J774A.1, and thioglycolate-elicited peritoneal macrophages. Additive inhibitory effect of an HO-1 inducer hemin and NE or NI on LPS-induced NO prodn. and iNOS expression was identified, and HO enzyme inhibitor tin protoporphyrin (SnPP) attenuated the inhibitory effects of HT, NE, and hemin on LPS-induced NO prodn. Both NE and HT showed no effect on iNOS mRNA and protein stability in RAW264.7 cells. Removal of rutinose at C7 of HD and NI by enzymic digestion using hesperidinase (HDase) and naringinase (NIase) produce inhibitory activity on LPS-induced NO prodn., according to the prodn. of the aglycons, HT and NE, by high-performance liq. chromatog. (HPLC) anal. Furthermore, the amt. of NO produced by LPS or lipoteichoic acid (LTA) was significantly reduced in HO-1-overexpressing cells (HO-1/RAW264.7) compared to that in parental cells (RAW264.7). Results of the present study provide scientific evidence to suggest that rutinose at C7 is a neg. moiety in flavonoid inhibition of LPS-induced NO prodn., and that HO-1 is involved in the inhibitory mechanism of flavonoids on LPS-induced iNOS and NO prodn.

Abstract

Anti-inflammatory effect of heme oxygenase 1: Glycosylation and nitric oxide inhibition in macrophages. Lin, Hui-Yi; Shen, Shing-Chuan; Chen, Yen-Chou. Graduate Institute of Pharmaceutical Sciences, School of Pharmacy, Taipei Medical University, Taipei, Taiwan. Journal of Cellular Physiology (2004), Volume Date 2005, 202(2), 579-590. Publisher: Wiley-Liss, Inc., CODEN: JCLLAX ISSN: 0021-9541. Journal written in English. CAN 142:309475 AN 2005:82225 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The design and development of a truly nano heterogeneous catalyst for the Claisen-Schmidt condensation (CSC) of benzaldehydes with 2-hydroxyacetophenone to yield substituted chalcones followed by isomerization to afford flavanones with excellent yields and selectivity is described.

Abstract

Synthesis of flavanones using nanocrystalline MgO. Choudary, B. M.; Ranganath, K. V. S.; Yadav, Jagajit; Kantam, M. Lakshmi. Inorganic Chemistry Division, Indian Institute of Chemical Technology, Hyderabad, India. Tetrahedron Letters (2005), 46(8), 1369-1371. Publisher: Elsevier B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN 142:336154 AN 2005:85999 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


different from those used in the training set as well as to classify harmless compds. clearly as being non-toxic. This suggests that our approach can be used for the prediction of adverse effects of drug mols. and chems.


flavanone

From the stem wood of Erythrina latissima, two isoflavones and a flavanone were isolated and characterized as 7,3'-dihydroxy-4'-methoxy-5'-(γ,γ-dimethylallyl)isoflavone (erylatissin A, I), 7,3'-dihydroxy-6'',6''-dimethyl-4'',5''-dehydropyrano[2'',3'': 4',5']isoflavone (erylatissin B, II), (-)-7,3'-dihydroxy-4'-methoxy-5'-(γ,γ-dimethylallyl)flavanone (erylatissin C, III), resp., in addn. to 10 known flavonoids. Structures of these compds. were detd. on the basis of their spectroscopic data. These compds. showed antimicrobial activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Candida mycoderma. The isolated compds. also exhibited weak radical scavenging properties towards DPPH radical.

Abstract

Antimicrobial and radical scavenging flavonoids from the stem wood of Erythrina latissima. Chacha, Musa; Bojase-Moleta, Gomotsang; Majinda, Runner R. T. Department of Chemistry, University of Botswana, Gaborone, Botswana. Phytochemistry (Elsevier) (2005), 66(1), 99-104. Publisher: Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 142:313202 AN 2005:44361 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The authors describe for the first time a nontransgenic metabolic engineering approach to developing a high flavonoid tomato using a wild tomato species (Lycopersicon pennellii v. puberulum) and demonstrate the opportunities for restoring functional pathways using the genetic resources of wild species, resulting in prodn. of healthier foods.

Abstract

Utilization of the genetic resources of wild species to create a nontransgenic high flavonoid tomato. Willits, Michael G.; Kramer, Catherine M.; Prata, Rogerio T. N.; De Luca, Vincenzo; Potter, Brian G.; Steffens, John C.; Graser, Gerson. Syngenta Biotechnology, Inc., Research Triangle Park, NC, USA. Journal of Agricultural and Food Chemistry (2005), 53(4), 1231-1236. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 142:315578 AN 2005:55444 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The prenylated flavanone was synthesized from phloroacetophenone. All the new products were characterized by the spectral data and microanal.

Abstract

Synthesis of 5,7-dihydroxy-6,8-di-C-prenyl-4'-O-prenyl-flavanone. Hossain, M. Amzad; Saravanand; Ismail, Zhari. School of Pharmaceutical Sciences, University Sains Malaysia, Pulau Pinang, Malay. Pakistan Journal of Scientific and Industrial Research (2004), 47(5), 332-335. Publisher: Pakistan Council of Scientific and Industrial Research, CODEN: PSIRAA ISSN: 0030-9885. Journal written in English. CAN 143:248176 AN 2005:36854 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

HO

OH

OMe

Me Me

O

O

HO

OH

O

Me

Me

O

O

HO

OH

OMe

Me

Me

I

III

II


flavanone

US 2003-532158P P 20031223US 2003-483949P P 20030701Priority Application JP 2007326872 A 20071220 JP 2007-203287 20070803 JP 2007530417 T 20071101 JP 2006-518817 20040701






Compositions for manipulating the lifespan and stress response of cells and organisms. Sinclair, David A.; Howitz, Konrad T.; Zipkin, Robert E. (President and Fellows of Harvard College, USA; Biomol International L.P.). PCT Int. Appl. (2005), 224 pp. CODEN: PIXXD2 WO 2005002672 A2 20050113 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-US21465 20040701. Priority: US 2003-483949 20030701; US 2003-532158 20031223. CAN 142:127624 AN 2005:29238 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Heterogeneous catalytic synthesis of flavanones: an investigation of the functional group substitution effects, kinetics, and reaction mechanism. Hargrove, Sirena Colletta. Univ. of South Carolina, Columbia, SC, USA. Avail. UMI, Order No. DA3115113. (2003), 120 pp. From: Diss. Abstr. Int., B 2004, 64(12), 6201. Dissertation written in English. CAN 143:172427 AN 2005:29604 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract JP 2006-518817 A3 20040701US 2003-532158P P 20031223US 2003-483949P P 20030701Priority Application JP 2007326872 A 20071220 JP 2007-203287 20070803 US 20060084135 A1 20060420 US 2004-884062 20040701




Compositions for manipulating the lifespan and stress response of cells and organisms. Sinclair, David A. (President and Fellows of Harvard College, USA). PCT Int. Appl. (2005), 223 pp. CODEN: PIXXD2 WO 2005002555 A2 20050113 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-US21479 20040701. Priority: US 2003-483949 20030701; US 2003-532158 20031223. CAN 142:127622 AN 2005:29182 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Provided herein are methods and compns. for modulating the activity of sirtuin deacetylase protein family members; p53 activity; apoptosis; lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compd., such as a sphingolipid, e.g., sphingosine.

Abstract JP 2006-518817 A3 20040701WO 2004-US21465 W 20040701


flavanone

On page 448, Results section, "Reproducibility of this Aromatase Assay" subheading, sentence 1 should read: "The intra-assay reproducibility of the system was evaluated by calculation of coefficients of variation (CV), where CV = 100% × SD/mean.". Sentence 3 should read: "Inter-assay reproducibility in the aromatase assay was determined by comparing the IC50's calculated for each of the triplicate dose-response curves for 4-OHA and imazalil, which were chosen because their inhibitory effects covered a wide concentration range.".

Abstract

A novel nonradioactive method for measuring aromatase activity using a human ovarian granulosa-like tumor cell line and an estrone ELISA. [Erratum to document cited in CA142:033083]. Ohno, Ken; Araki, Naohiro; Yanase, Toshihiko; Nawata, Hajime; Iida, Mitsuru. EcoScreen R & D Section, Endocrine Disrupting Chemical Analysis Center, Otsuka Life Science Initiative, Otsuka Pharmaceutical Co., Ltd., Kawauchi-cho, Tokushima, Japan. Toxicological Sciences (2005), 83(2), 406. Publisher: Oxford University Press, CODEN: TOSCF2 ISSN: 1096-6080. Journal written in English. CAN 143:399952 AN 2005:24206 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Expanded CUG triplet repeats carrying mRNA seem to be responsible for myotonic dystrophy type 1 (DM1). To study the pathogenesis of DM1, we constructed a DM1 cell culture model using a PC12 neuronal cell line and screened flavonoids that ameliorate this mRNA gain of function. The expanded 250 CTG repeat was subcloned into the 3'-untranslated region of the luciferase gene yielding a stable transformant of PC12 (CTG-250). The cytotoxicity of CTG-250 was evaluated by intracellular LDH activity, and the cis-effect by luciferase activity. To find agents that alter CTG-250 toxic effects, 235 bioflavonoids were screened. An increased cis-effect and cytotoxicity were found when CTG-250 was treated with nerve growth factor to induce differentiation. Western blotting with anti-caspase-3 antibody suggested that cell death was caused by apoptosis. Screening anal. confirmed that a flavone (toringin), an isoflavones (genistein and formononetin), a flavanone (isosakuranetin), and DHEA-S prevent both the cytotoxicity and cis-effect of CTG-250 and that a flavanone (naringenin), isoflavone (ononin), and xanthylatin strongly inhibit the cis-effect of CTG repeats. In conclusion, we found that this neuronal cell line, which expresses the CUG repeat-bearing mRNA, showed cis-effects through the reporter gene and neuronal death after cell differentiation in vitro. However, some flavonoids and DHEA-S inhibit both the cis-effect and cytotoxicity, indicating that their chem. structures work to ameliorate both these toxic effects. This system makes it easy to evaluate the toxic effects of expanded CTG repeats and therefore should be useful for screening other DM1 treatments for their efficacies.

Abstract

Some flavonoids and DHEA-S prevent the cis-effect of expanded CTG repeats in a stable PC12 cell transformant. Furuya, Hirokazu; Shinnoh, Nobue; Ohyagi, Yasumasa; Ikezoe, Koji; Kikuchi, Hitoshi; Osoegawa, Manabu; Fukumaki, Yasuyuki; Nakabeppu, Yusaku; Hayashi, Toshimitsu; Kira, Jun-ichi. Department of Neurology, Neurological Institute, Graduate School of Medical Sciences, Kyushu University, Fukuoka, Japan. Biochemical Pharmacology (2005), 69(3), 503-516. Publisher: Elsevier B.V., CODEN: BCPCA6 ISSN: 0006-2952. Journal written in English. CAN 142:273870 AN 2005:28043 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Provided herein are methods and compns. for modulating the activity of sirtuin deacetylase protein family members; p53 activity; apoptosis, lifespan and sensitivity to stress of cells and organisms. Exemplary methods comprise contacting a cell with an activating compd., such as a flavone, stilbene, flavanone, isoflavone, catechin, chalcone, tannin or anthocyanidin; or an inhibitory compd., such as a sphingolipid, e.g., sphingosine. It is shown that sirtuin activators mimic calorie restriction and delay aging in metazoans.


flavanone




Preparation of rutin esters of flavonoids with ω-substituted C6-C22 fatty acids and used in cosmetics as skin protectors against damages due to UV-radiation. Moussou, Philippe; Falcimaigne, Aude; Ghoul, Mohamed; Danous, Louis; Pauly, Gilles. (Cognis France S.A., Fr.). PCT Int. Appl. (2005), 32 pp. CODEN: PIXXD2 WO 2005000831 A1 20050106 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-EP6281 20040611. Priority: EP 2003-13899 20030620. CAN 142:94063 AN 2005:14387 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Diets high in flavonoids have long been assocd. with nutritional recommendations, a healthy lifestyle, and the prevention of chronic diseases. However, identification of specific beneficial effects from specific flavonoids and flavonoid-rich foods has been a challenging area, probably due to a nonessential or conditional role for flavonoids in human nutrition. Nonetheless, recent efforts in the area of high flavonoid-contg. foods and cardiovascular disease have begun providing the first demonstrations of specific effects and mechanisms of action in well-controlled studies. The early studies have shown that flavonoids have several anti-atherosclerotic activities including anti-inflammatory, antioxidant, antiproliferative, antiplatelet, and provessel function activities. Cholesterol-lowering and antihypertensive effects of flavonoids have been studied and appear minimal in humans. The studies also demonstrate several possible mechanisms and pleiotropic effects of flavonoids that may be active in redn. in the risk of cardiovascular disease. Several subclasses of flavonoids may contribute toward the apparent beneficial effects and include flavones, flavonols, flavanones, catechins isoflavones, proanthocyanidins, and anthocyanidins. Further studies are necessary for confirmation of the beneficial effects, identification of dose-response relationships, and identification the most bioactive flavonoids.

Abstract

Flavonoids and Cardiovascular Disease. Gross, Myron. Molecular Epidemiology and Biomarker Research Laboratory, Department of Laboratory Medicine and Pathology, School of Medicine, Division of Epidemiology, School of Public Health, University of Minnesota, Minneapolis, MN, USA. Pharmaceutical Biology (Lisse, Netherlands) (2004), 42(Suppl.), 21-35. Publisher: Taylor & Francis The Netherlands, CODEN: PHBIFC ISSN: 1388-0209. Journal; General Review written in English. CAN 142:384781 AN 2005:22612 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The present invention provides a sepg. agent for optical isomers having a porous monolithic inorg. type carrier and polysaccharide or a deriv. thereof supported on the monolithic inorg. type carrier, and a sepn. column for optical isomers in which the sepg. agent for optical isomers is held in a column tube. According to the invention, the sepg. agent for optical isomers and the sepn. column for

Abstract JP 2004-16952 A 20040126JP 2003-155414 A 20030530Priority Application


EP 1500430 A3 20060524EP 1500430 A2 20050126 EP 2004-12766 20040528JP 2005017268 A 20050120 JP 2004-16952 20040126US 20040262229 A1 20041230 US 2004-854244 20040527Patent No. Kind Date Application No. Date Patent Family Information

Separating agent for optical isomers, method of production thereof, and separation column for optical isomers. Okamoto, Yoshio; Yamamoto, Chiyo; Bezhan, Chankvetadze. (Japan). U.S. Pat. Appl. Publ. (2004), 19 pp. CODEN: USXXCO US 2004262229 A1 20041230 Patent written in English. Application: US 2004-854244 20040527. Priority: JP 2003-155414 20030530; JP 2004-16952 20040126. CAN 142:93183 AN 2005:784 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention refers to esters of flavonoids such as flavones, flavonols, flavanones, flavanols, flavanolols, isoflavones, anthocyanins, proanthocyanidins, chalcones, aurones and hydroxycoumarins conjugated by an ester bond to an ω substituted C6-C22 fatty acid. These flavonoid derivs. exhibit excellent skin protecting properties esp. against damages due to UV-radiation. They show very good chem. stability and are easily incorporated into cosmetic and pharmaceutical formulations.


R: DE, ES, FR, GB, ITEP 1636204 A1 20060322 EP 2004-739782 20040611


flavanone

JP 2004-123479 A 20040419JP 2003-177333 A 20030620JP 2003-177332 A 20030620Priority Application US 20070161579 A1 20070712 US 2007-686038 20070314 US 7256214 B2 20070814US 20060292204 A1 20061228 US 2005-562019 20051219CN 101130536 A 20080227 CN 2007-10152920 20040618CN 1809551 A 20060726 CN 2004-80017013 20040618

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, FI, RO, CY, TR, BG, CZ, EE, HU, PL, SK

EP 1640371 A1 20060329 EP 2004-746433 20040618AU 2004249614 B2 20080403AU 2004249614 A1 20041229 AU 2004-249614 20040618JP 2005029778 A 20050203 JP 2004-123480 20040419JP 2005029560 A 20050203 JP 2004-123479 20040419


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


Flavanone compound and uses thereof. Kumazawa, Shigenori; Nakayama, Tsutomu; Shimoi, Kayoko; Goto, Takaki; Fukumoto, Syuichi; Arakaki, Tsutomu. (Pokka Corporation, Japan). PCT Int. Appl. (2004), 46 pp. CODEN: PIXXD2 WO 2004113318 A1 20041229 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2004-JP8964 20040618. Priority: JP 2003-177333 20030620; JP 2003-177332 20030620; JP 2004-123480 20040419; JP 2004-123479 20040419. CAN 142:86688 AN 2004:1154692 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


optical isomers which have high asymmetry recognition ability and can be used particularly at a high flow rate when used for the sepn. of optical isomers is provided. Thus, cellulose tris(3,5-dimethylphenylcarbamate) or amylose tris(3,5-dimethylphenylcarbamate) was supported on a monolithic inorg. type porous body and used to sep. a variety of substances into their individual enantiomers by HPLC. The inorg. porous body allows higher pressure to be applied during the loading of the stationary phase, resulting in higher doping and increased sepn. of optical isomers.


flavanone

Oral Silibinin Inhibits Lung Tumor Growth in Athymic Nude Mice and Forms a Novel Chemocombination with Doxorubicin Bibliographic Information Answer 692:

A comparison between the extn. yields of xanthones and flavanones from the root bark of the Maclura pomifera by solid-liq. extn. (SLE), matrix solid phase dispersion (MSPD), and an alternative method using sea sand as a sample disruptor, is presented here. Two extn. solvents were used for all extn. techniques, dichloromethane and methanol:water, (9:1, vol./vol.). The extn. procedures were reproducible as the R.S.D. values were less than 5% for almost all compds. A recovery above 80% was obtained for macluraxanthone using the sea sand extn. procedure. Statistical treatment, ANOVA-single factor, was used to evaluate the different extn. procedures, and homogenization of plant material with sand followed by elution with dichloromethane provided the most efficient and rapid extn. method.

Abstract

Novel methods to extract flavanones and xanthones from the root bark of Maclura pomifera. Teixeira, D. Martins; Teixeira da Costa, C. CLAV Rua Romao Ramalho n° 59, Departamento de Quimica, Universidade de Evora, Evora, Port. Journal of Chromatography, A (2005), 1062(2), 175-181. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 142:214643 AN 2004:1152170 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OHO

OH O

OH

OH

CH 2 CH C

Me

CH 2 CH C Me

Me

( )2

I

An antioxidant, antibacterial, antitumor agent, food or beverage, cosmetic, quasi-drug prepn., and medical product which each contains the novel flavanone compd. represented by the following structural formula. Alternatively, the antioxidant, antibacterial, antitumor agent, food or beverage, cosmetic, quasi-drug prepn., and medical product each contains at least one flavanone compd. selected among nymphaeol-A, nymphaeol-B, and nymphaeol-C. Structural formula (I).

Abstract US 2005-562019 A3 20051219CN 2004-80017013 A3 20040618WO 2004-JP8964 W 20040618JP 2004-123480 A 20040419


flavanone

The Differential Tissue Distribution of the Citrus Flavanone Naringenin Following Gastric Instillation. El Mohsen, Manal Bibliographic Information Answer 694:

Twenty six phenolic substances including representatives of the families, flavanones, flavanols and procyanidins, flavonols, isoflavones, phenolic acids and phenylpropanones were investigated for their effects on lipid oxidn., membrane fluidity and membrane integrity. The incubation of synthetic phosphatidylcholine (PC) liposomes in the presence of these phenolics caused the following effects: (a) flavanols, their related procyanidins and flavonols were the most active preventing 2,2'-azo-bis (2,4-dimethylvaleronitrile) (AMVN)-induced 2-thiobarituric acid-reactive substances (TBARS) formation, inducing lipid ordering at the water-lipid interface, and preventing Triton X-100-induced membrane disruption; (b) all the studied compds. inhibited lipid oxidn. induced by the water-sol. oxidant 2,2'-azo-bis (2-amidinopropane) (AAPH), and no family-related effects were obsd. The protective effects of the studied phenolics on membranes were mainly assocd. to the hydrophilicity of the compds., the degree of flavanol oligomerization, and the no. of hydroxyl groups in the mol. The present results support the hypothesis that the chem. structure of phenolics conditions their interactions with membranes. The interactions of flavonoids with the polar head groups of phospholipids, at the lipid-water interface of membranes, should be considered among the factors that contribute to their antioxidant effects.

Abstract

The interaction of flavonoids with membranes: potential determinant of flavonoid antioxidant effects. Erlejman, A. G.; Verstraeten, S. V.; Fraga, C. G.; Oteiza, P. I. Department of Biological Chemistry-IQUIFIB (UBA-CONICET); School of Pharmacy and Biochemistry, University of Buenos Aires, Argent. Free Radical Research (2004), 38(12), 1311-1320. Publisher: Taylor & Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in English. CAN 142:348946 AN 2004:1149813 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The acute and cumulative dose-related toxicity and drug resistance, mediated via nuclear factor κB (NFκB), of anthracycline anticancer drugs pose a major problem in cancer chemotherapy. Here, we report that oral silibinin (a flavanone) suppresses human non-small-cell lung carcinoma A549 xenograft growth (P = 0.003) and enhances the therapeutic response (P < 0.05) of doxorubicin in athymic BALB/c nu/nu mice together with a strong prevention of doxorubicin-caused adverse health effects. Immunohistochem. analyses of tumors showed that silibinin and doxorubicin decrease (P < 0.001) proliferation index and vasculature and increase (P < 0.001) apoptosis; these effects were further enhanced (P < 0.001) in combination treatment. Pharmacol. dose of silibinin (60 μmol/L) achieved in animal study was biol. effective (P < 0.01 to 0.001, growth inhibition and apoptosis) in vitro in A549 cell culture together with an increased efficacy (P < 0.05 to 0.001) in doxorubicin (25 nmol/L) combination. Furthermore, doxorubicin increased NFκB DNA binding activity as one of the possible mechanisms for chemoresistance in A549 cells, which was inhibited by silibinin in combination treatment. Consistent with this, silibinin inhibited doxorubicin-caused increased translocation of p65 and p50 from cytosol to nucleus. Silibinin also inhibited cyclooxygenase-2, an NFκB target, in doxorubicin combination. These findings suggest that silibinin inhibits in vivo lung tumor growth and reduces systemic toxicity of doxorubicin with an enhanced therapeutic efficacy most likely via an inhibition of doxorubicin-induced chemoresistance involving NFκB signaling.

Abstract

Targeting Nuclear Factor κB-Mediated Inducible Chemoresistance. Singh, Rana P.; Mallikarjuna, G. U.; Sharma, Girish; Dhanalakshmi, Sivanandhan; Tyagi, Anil K.; Chan, Daniel C. F.; Agarwal, Chapla; Agarwal, Rajesh. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Sciences Center, Denver, CO, USA. Clinical Cancer Research (2004), 10(24), 8641-8647. Publisher: American Association for Cancer Research, CODEN: CCREF4 ISSN: 1078-0432. Journal written in English. CAN 142:423170 AN 2004:1150200 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Phytoestrogens in cancer prevention: Characterization and beneficial effects of kurarinone, a new flavanone and a major phytoestrogen constituent of Sophora flavescens Ait. De Naeyer, A.; Vanden Berghe, W.; De Keukeleire, D.; Haegeman, G. Ghent University, Ghent, Belg. Editor(s): Bagchi, Debasis; Preuss, Harry G. Phytopharmaceuticals in Cancer Chemoprevention


We used RNA blot anal. to examine the expression of six genes of the anthocyanin biosynthesis pathway in the flowers and fruit skins at three developmental stages of white and red peaches and a deep-red nectarine [Prunus persica (L.) Batch]. In the red peach 'Akatsuki' and the deep-red nectarine 'Flavortop', expression levels of anthocyanin biosynthesis genes were related to anthocyanin accumulation in the fruit skin; expression of all six genes dramatically increased at Stage III of fruit development, and anthocyanin concn. also increased at this stage. In the white peach 'Mochizuki', however, expression of the chalcone synthase gene (CHS) and the dihydroflavonol 4-reductase gene (DFR) was undetectable in Stage III, although the chalcone isomerase gene (CHI), the flavanone 3-hydroxylase gene (F3H), the anthocyanidin synthase gene (ANS), and the UDP-glucose-flavonoid 3-O-glucosyltransferase gene (UFGT) were expressed. We occasionally found red pigment in the skin of 'Mochizuki' peach. In these red skin areas, both CHS and DFR were clearly expressed in Stage III. These results suggest that CHS and DFR are the key regulatory genes in the process of anthocyanin biosynthesis in mature red peach and nectarine.

Abstract

Expression of anthocyanin biosynthesis genes in the skin of peach and nectarine fruit. Tsuda, Tomomi; Yamaguchi, Masami; Honda, Chikako; Moriguchi, Takaya. Japan Society for the Promotion of Science, Japan. Journal of the American Society for Horticultural Science (2004), 129(6), 857-862. Publisher: American Society for Horticultural Science, CODEN: JOSHB5 ISSN: 0003-1062. Journal written in English. CAN 142:478752 AN 2004:1119662 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Citrus flavonoids have been investigated for their biol. activity, with both anti-inflammatory and -carcinogenic effects being reported. However, little information is known on the bioavailability of these compds. in vivo. The objectives of this study were to det. the tissue distribution of naringenin after gastric gavage of [3H]-naringenin to rats. Unlabeled naringenin was also used to quantify the levels of naringenin and its major metabolites in tissues and eliminated in the urine and feces. Significant radioactivity was detected in the plasma as well as all tissues examd. 2 h post-gavage. After 18 h, higher levels of radioactivity were retained in plasma and tissues (55% of the administered radioactivity). Investigation of the nature of metabolites, using unlabeled naringenin, revealed that the glucuronides were the major components in plasma, tissues and urine, in addn. to the colonic metabolite 3-(4-hydroxyphenyl) propionic acid, detected in the urine. The aglycon was the form extensively retained in tissues after 18 h post-gavage. Total identified metabolites detected after 18 h in most tissues were only 1-5% of the levels detected after 2 h. However, the brain, lungs and heart retained 27, 20 and 11%, resp., relative to the total metabolites detected at 2 h. While radioactive detection suggests increased levels of breakdown products of naringenin after 18 h vs. 2 h, the products identified using unlabeled naringenin are not consistent with this, suggesting that a predominant proportion of the naringenin breakdown products at 18 h are retained as smaller decompn. mols. which cannot yet be identified.

Abstract

Abd; Marks, Joanne; Kuhnle, Gunter; Rice-Evans, Catherine; Moore, Kevin; Gibson, Glenn; Debnam, Edward; Srai, S. Kaila. Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, Kings College London, London, UK. Free Radical Research (2004), 38(12), 1329-1340. Publisher: Taylor & Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in English. CAN 142:168926 AN 2004:1149811 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

A new flavanone glucoside, bidenoside F (I), and a new chalcone glucoside, bidenoside G (II), along with the known compd. iso-okanin 7-O-(4'',6''-diacetyl)-β-D-glucopyranoside have been isolated from the aerial parts of Bidens bipinnata L. The structures were detd. on

Abstract

New flavanone and chalcone glucosides from Bidens bipinnata Linn. Li, Shuai; Kuang, Hai-Xue; Okada, Yoshihito; Okuyama, Toru. Institute of Materia Medica, Peking Union Medical College, Chinese Academy of Medical Sciences, Beijing, Peop. Rep. China. Journal of Asian Natural Products Research (2005), 7(1), 67-70. Publisher: Taylor & Francis Ltd., CODEN: JANRFI ISSN: 1028-6020. Journal written in English. CAN 143:23018 AN 2004:1075119 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Microarray anal. of Vitis vinifera cv. Shiraz developing berries has revealed the expression patterns of several categories of genes. Microarray slides were constructed from 4608 PCR-amplified cDNA clones derived from a ripening grape berry cDNA library. The mRNA expression levels of the genes represented by these cDNAs were measured in flowers, week 2 post-flowering whole berries, week 5, week 8, week 10 (veraison, green berries), week 12 and week 13 berry skin. In addn., a comparison of RNA expression in pigmented and unpigmented berry skin at veraison (week 10) was undertaken. Image and statistical anal. revealed four sets of genes with distinctive and similar expression profiles over the course of berry development. The first set was composed of genes which had max. RNA expression in flowers, followed by a steady decrease in expression. The most prominent group within this set were genes which have a role in photosynthesis. The second set of cDNAs was dominated by genes involved in flavonoid biosynthesis and had a peak of expression week 2 post-flowering. The data indicate coordinate regulation of flavonoid biosynthetic genes which code for the enzymes 4-coumarate-CoA ligase, chalcone synthase, chalcone isomerase, flavanone hydroxylase, anthocyanidin reductase and cytochrome b5. The third set of cDNAs exhibited max. expression week 5 post-flowering, midway between flowering and veraison, a period of rapid berry growth. This set of cDNAs is dominated by genes which code for structural cell wall proteins. The fourth set of genes was dramatically up-regulated at veraison and remained up-regulated until 13 wk post-flowering. This set of genes was composed of a diverse range of genes, a reflection of the complexity of ripening, most with no known function.

Abstract

cDNA microarray analysis of developing grape (Vitis vinifera cv. Shiraz) berry skin. Waters, Daniel L. E.; Holton, Timothy A.; Ablett, Effie M.; Lee, L. Slade; Henry, Robert J. Centre for Plant Conservation Genetics, Southern Cross University, Lismore, Australia. Functional & Integrative Genomics (2005), 5(1), 40-58. Publisher: Springer GmbH, CODEN: FIGUBY ISSN: 1438-793X. Journal written in English. CAN 142:349920 AN 2004:1079119 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The biol. effects and potential health benefits of phytoestrogens are outlined. The focus is on the isolation and characterization of kurarinone from Sophora flavescens legume plant. Kurarinone was extd. from dried ground plant material, tested in vitro for estrogenic, cell proliferation, and anticancer effects, and was chem. characterized by 1H-NMR, 13C-NMR, and other techniques. Kurarinone holds promise as a prophylactic compd. that may have beneficial effects in the treatment of various postmenopausal disturbances and neoplastic disorders.

Abstract

(2005), 427-448. Publisher: CRC Press LLC, Boca Raton, Fla CODEN: 69GGT2 Conference written in English. CAN 143:25797 AN 2004:1081502 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Silica gel-supported InBr3 and InCl3: new catalysts for the facile and rapid oxidation of 2'-hydroxychalcones and flavanones to their corresponding flavones under solvent free conditions. Ahmed, Naseem; Ali, Hasrat; van Lier, Johan E. Department of Nuclear Medicine and Radiobiology, Faculty of Medicine, Universite de Sherbrooke, Sherbrooke, QC, Can. Tetrahedron Letters (2005), 46(2), 253-256. Publisher: Elsevier B.V., CODEN: TELEAY ISSN: 0040-4039. Journal written in English. CAN


In Discussion, paragraph 4, the following sentence should have read, "In TBT, the reduction of aromatase activity was also observed, however the cell viability was declined in parallel.". There are no Supplementary Data for this article.

Abstract

A novel nonradioactive method for measuring aromatase activity using a human ovarian granulosa-like tumor cell line and an estrone ELISA. [Erratum to document cited in CA142:033083]. Ohno, Ken; Araki, Naohiro; Yanase, Toshihiko; Nawata, Hajime; Iida, Mitsuru. EcoScreen R & D Section, Endocrine Disrupting Chemical Analysis Center, Otsuka Life Science Initiative, Otsuka Pharmaceutical Co., Ltd., Kawauchi-cho, Tokushima, Japan. Toxicological Sciences (2005), 83(1), 204. Publisher: Oxford University Press, CODEN: TOSCF2 ISSN: 1096-6080. Journal written in English. CAN 143:319235 AN 2004:1070107 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

OHOHCH 2

O

OH

AcO

OH

OAc

O

OH

O

OH

OHCH 2

O

OH

AcO

OH

OH

O

I

II

the basis of spectroscopic methods.


flavanone

Highly ordered large pore SBA-15 silica functionalized with up to 16% aminopropyl groups was synthesized for the first time via Abstract

Preparation of ordered large pore SBA-15 silica functionalized with aminopropyl groups through one-pot synthesis. Wang, Xueguang; Lin, Kyle S. K.; Chan, Jerry C. C.; Cheng, Soofin. Department of Chemistry, National Taiwan University, Taipei, Taiwan. Chemical Communications (Cambridge, United Kingdom) (2004), (23), 2762-2763. Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in English. CAN 142:134424 AN 2004:1037520 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The non-empirical assignment of the abs. configuration of (-)-naringenin, the aglycon of (-)-naringin, a flavanone glycoside abundant in the albedo of immature grapefruits and showing several interesting biol. properties, has been approached by two different methods: (a) the exciton anal. of the CD spectrum and (b) the ab initio calcn. of the optical rotatory power. Both the methods indicate the configurational correlation (-)/(S), as empirically suggested by Gaffield. A comparison of advantages and limitations of the two methods of anal. is also presented.

Abstract

Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power. Giorgio, Egidio; Parrinello, Nunziatina; Caccamese, Salvatore; Rosini, Carlo. Dipartimento di Chimica, Universita della Basilicata, Potenza, Italy. Organic & Biomolecular Chemistry (2004), 2(24), 3602-3607. Publisher: Royal Society of Chemistry, CODEN: OBCRAK ISSN: 1477-0520. Journal written in English. CAN 142:197715 AN 2004:1051487 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

MeO OMe

I

Silica gel supported InBr3 or InCl3 were explored as a solid-support catalysts for the facile and efficient oxidn., under solvent free conditions, of 2'-hydroxychalcones and flavanones to yield flavones, e.g., I, in good yield. The catalysts were easily prepd., stable, and efficient under mild reaction conditions.

Abstract 142:197716 AN 2004:1068432 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

To clarify the metabolic pathways of flavanones in mammals, the metab. of (±)-flavanone and (±)-4'-methoxyflavanone by rat liver microsomes and recombinant human P450s in which structural changes are readily identifiable were examd. The β-NADP (NADPH)-dependent formation of flavone plus (±)-2,3-trans-flavanonol and 4'-methoxyflavone plus (±)-2,3-trans-4'-methoxyflavanoonol, resp., by rat liver microsomes was obsd. The same metabolites were generated by recombinant human P450s in addn. to the formation of isoflavone from (±)-flavanone. The kinetic isotope effects in these reactions were examd. using deuterated (±)-flavanone and (±)-4'-methoxyflavanone. There was a strong isotope effect in the prodn. of flavonols, but the isotope effect in the prodn. of flavones was small. The results indicated that the P 450-mediated conversion of (±)-flavanone and of (±)-4'-methoxyflavanone to the corresponding metabolites proceeded via abstraction of a hydrogen radical from the C-2- or C-3-position of the flavanone skeleton. The antioxidant properties of flavanone and its metabolites were examd. by measuring superoxide-scavenging activity in a xanthine-xanthine oxidase-cytochrome c system. (±)-2,3-Trans-Flavanonol had higher activity

Abstract

Oxidation and rearrangements of flavanones by mammalian cytochrome P450. Kagawa, H.; Takahashi, T.; Ohta, S.; Harigaya, Y. Dep. Organic Synthesis, Sch. Pharm. Sci., Kitasato Univ., Minato-ku, Tokyo, Japan. Xenobiotica (2004), 34(9), 797-810. Publisher: Taylor & Francis Ltd., CODEN: XENOBH ISSN: 0049-8254. Journal written in English. CAN 142:232287 AN 2004:1028112 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Polyphenolic compds. are widely distributed in the vegetable kingdom and are therefore consumed regularly in the human diet. Epidemiol. studies suggest that foods rich in polyphenolic compds. contribute to reducing the risk of cancer. The purpose of our work is to: 1) study the possible cytotoxicity and antiproliferative effects of 13 polyphenolic compds. on 3 cell lines of melanocytes, 2 of melanoma (B16F10 and SK-MEL-1), and 1 of nontransformed melanocytes (Melan-a); and 2) identify the possible relationship between the chem. structure of the tested compds. and their effect on cellular viability. The said polyphenolic compds. corresponded to 8 flavonoids with varying hydroxyl and methoxyl substituents, related structurally through the oxidn. state of their flavonoid skeleton, a catechin polymer and 4 phenolic acids. The cytotoxic activity of all the studied compds. was modest or not apparent. The flavonoids luteolin, tangeretin, baicalein, quercetin, and myricetin, and gallic acid showed antiproliferative effects on the tested lines. Our results suggest that a correlation exists between the structural oxidn. state and the position, no., and nature of substituents of the polyphenolic compds. studied and their antiproliferative effects.

Abstract

Cytotoxicity and antiproliferative activities of several phenolic compounds against three melanocytes cell lines: relationship between structure and activity. Yanez, Josefa; Vicente, Vicente; Alcaraz, Miguel; Castillo, Julian; Benavente-Garcia, Obdulio; Canteras, Manuel; Lozano Teruel, Jose A. Department of Pathology, Faculty of Medicine, University of Murcia, Murcia, Spain. Nutrition and Cancer (2004), 49(2), 191-199. Publisher: Lawrence Erlbaum Associates, Inc., CODEN: NUCADQ ISSN: 0163-5581. Journal written in English. CAN 142:253667 AN 2004:1034484 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


co-condensation of tetra-Et orthosilicate (TEOS) and 3-aminopropyltriethoxysilane (APTES) using an amphiphilic block copolymer (Pluronic 123) as the structure-directing agent. This silica gave high catalytic activity and selectivity toward flavanone synthesis through aldol condensation and subsequent intramol. Michael addn. of benzaldehyde and 2-hydroxyacetophenone. The aldol condensation of benzaldehyde with (1-(2-hydroxyphenyl)ethanone gave 1-(2-hydroxyphenyl)-3-phenyl-2-propen-1-one. The Michael reaction of the latter then gave 2,3-dihydro-2-phenyl-4H-1-benzopyran-4-one (flavanone). The Knoevenagel reaction of (cyano)acetic acid Et ester with benzaldehyde gave 2-cyano-3-phenyl-2-propenoic acid Et ester.


flavanone

Aromatase is a key enzyme in steroidogenesis and plays an important role in sexual differentiation, fertility, and carcinogenesis. Abstract

A novel nonradioactive method for measuring aromatase activity using a human ovarian granulosa-like tumor cell line and an estrone ELISA. Ohno, Ken; Araki, Naohiro; Yanase, Toshihiko; Nawata, Hajime; Iida, Mitsuru. EcoScreen R & D Section, Endocrine Disrupting Chemical Analysis Center, Otsuka Life Science Initiative, Otsuka Pharmaceutical Co., Ltd., Kawauchi-cho, Tokushima, Japan. Toxicological Sciences (2004), 82(2), 443-450. Publisher: Oxford University Press, CODEN: TOSCF2 ISSN: 1096-6080. Journal written in English. CAN 142:33083 AN 2004:1009006 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Black chokeberry, Aronia melanocarpa (Michx.) Elliott (Rosaceae), was investigated for its flavonoid content. The flavanone eriodictyol 7-O-β-glucuronide, together with the quercetin derivs. 3-O-(6''-O-β-arabinosyl-β-glucoside), 3-O-(6''-α-rhamnosyl-β-galactoside), 3-O-(6''-α-rhamnosyl-β-glucoside), 3-O-β-galactoside and 3-O-β-glucoside, were detected in the fruits and flower umbels. The rare compds. 1-3 were isolated and structurally elucidated by use of 1D- and 2D-NMR expts. together with electrospray mass spectrometry. Compds. 4-6 were characterized by co-chromatog. and by liq. chromatog.-mass spectrometry. The black chokeberries contained >71 mg flavonols per 100 g fresh wt.

Abstract

Flavonoids from black chokeberries, Aronia melanocarpa. Slimestad, Rune; Torskangerpoll, Kjell; Nateland, Haavard S.; Johannessen, Tina; Giske, Nils H. PlantChem, Sandnes, Norway. Journal of Food Composition and Analysis (2004), Volume Date 2005, 18(1), 61-68. Publisher: Elsevier Ltd., CODEN: JFCAEE ISSN: 0889-1575. Journal written in English. CAN 143:210746 AN 2004:1023120 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. The paper reviews the antioxidant effect of flavonoids. The research development of extg. methods of flavonoids is discussed.

Abstract

Progress on antioxidant activation and extracting technology of flavonoids. Wang, Qiuan; Zhou, Bing; Shan, Yang. Chemistry and Chemical Engineering University College, Hunan University, Changsha, Hunan, Peop. Rep. China. Huagong Shengchan Yu Jishu (2004), 11(5), 29-32. Publisher: Huagong Shengchan Yu Jishu Bianjibu, CODEN: HSYJAC ISSN: 1006-6829. Journal; General Review written in Chinese. CAN 143:149876 AN 2004:1026426 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


than that of other flavonoids. Flavanones are metabolized by mammalian P450s, providing important information relevant to the metab. and pharmacol. action of dietary flavanones.


flavanone


Flavonoid glycosides with enzymic modification for prevention and treatment of type-II diabetes. Tamura, Wataru; Matsuyama, Kayo; Kagami, Yoshiaki. (Ezaki Glico Co., Japan). Jpn. Kokai Tokkyo Koho (2004), 6 pp. CODEN: JKXXAF JP 2004323469 A 20041118 Patent written in Japanese. Application: JP 2003-123434 20030428. Priority: . CAN 141:388723 AN 2004:993141 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A chiral selector, mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin, was synthesized through a facile synthetic route and chem. immobilized onto porous silica gel via hydrosilylation to afford a cyclodextrin based chiral stationary phase MeCD-CSP. This chiral stationary phase exhibited good enantioselectivity under std. HPLC conditions. The optimal resoln. of 1-(p-bromophenyl)ethanol and bromopheniramine was achieved under normal-phase conditions using a mobile phase comprising n-hexane and 2-propanol (IPA). The enantiosepn. of warfarin, suprofen and flavanones under reversed-phase conditions were optimized and efficient enantiosepns. for these analytes were obtained.

Abstract

Enantioseparation on mono(6A-N-allylamino-6A-deoxy)permethylated β-cyclodextrin covalently bonded silica gel. Lai, Xiang-Hua; Ng, Siu-Choon. Department of Chemistry, National University of Singapore, Singapore, Singapore. Journal of Chromatography, A (2004), 1059(1-2), 53-59. Publisher: Elsevier B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 142:147379 AN 2004:1004679 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Importantly, a variety of chems. in the environment may influence its activity and thereby disrupt endocrine function. In the current studies, we developed a novel nonradioactive method for measuring aromatase activity that uses a specific ELISA for estrone along with KGN human ovary granulosa-like carcinoma cells. This cell line has relatively high aromatase activity, and because it lacks 17α-hydroxylase, it secretes little or no androstenedione, 17β-estradiol, or estrone. Therefore, aromatase activity can be assayed simply by measuring the prodn. of estrone in the culture medium after addn. of the substrate, androstenedione. Furthermore, by making a slight change in the com. ELISA kit and optimizing the exptl. conditions, we developed a sensitive aromatase assay that could measure a wide range of estrone concns. with very low interference by androgens. We used this assay to investigate the effects of 23 chems. that have been previously reported to affect aromatase activity in vitro. We confirmed that 17 of 23 test chems. had inhibitory or inducible effects, although the specific effects of some were different than previously reported. In conclusion, we have developed a simple, sensitive, and nonradioactive assay that can be used for large-scale screening of compds. that can disrupt endocrine function by influencing aromatase activity.


flavanone

Petroleum ether, dichloromethane, and ethanolic exts. of the stem bark and leaves of Uvaria scheffleri (Annonaceae) exhibited antifungal activity against Aspergillus niger (wild strain), Aspergillus fumigatus (wild strain), and a Penicillium species (wild strain). The ethanol ext. of the stem bark was also active against Candida albicans (Strain H6392). The dichloromethane ext. of the leaves showed the highest antifungal activity and in addn. it showed antibacterial activity against Staphylococcus aureus (NCTC 6571). Fractionation of the dichloromethane ext. of the leaves yielded nine known compds. They included a 1 : 1 mixt. of stigmasterol (1) and β-sitosterol

Abstract

In Vitro Antibacterial and Antifungal Activities of Extracts and Compounds from Uvaria scheffleri. Moshi, Mainen; Joseph, Cosam; Innocent, Esther; Nkunya, Mayunga. Department of Pharmacology and Toxicology, Institute of Traditional Medicine, Dar Es Salaam, Tanzania. Pharmaceutical Biology (Lisse, Netherlands) (2004), 42(4-5), 269-273. Publisher: Taylor & Francis The Netherlands, CODEN: PHBIFC ISSN: 1388-0209. Journal written in English. CAN 143:74652 AN 2004:962011 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Recent studies on food function show that foods and their components exhibit anti-inflammatory and anti-allergic activities. We have investigated the suppressive effect of flavonoids on lipopolysaccharide (LPS)-induced prostaglandin (PG) prodn. on rat peritoneal macrophage and tumor necrosis factor (TNF)-α-stimulated E-selectin expression on human umbilical vein endothelial cells (HUVECs) carrying out a comparative examn. of the flavonoids. A comparison of the subclasses showed that flavone and flavanone on prostaglandin prodn., flavone and flavonol on E-selectin expression were relatively more effective than other subclasses. From the viewpoint of the structure, the C2-C3 double bond of C ring and the 4-oxo functional group are essential for their inhibition activities. The glycosylated derivs. of the various flavonoids exhibit less inhibitory activities than their corresponding aglycons.

Abstract

Inhibitory effects of several flavonoids on prostaglandin production and E-selectin expression in cultured animal cells. Takano-Ishikawa, Y.; Goto, M.; Yamaki, K. National Food Research Institute, Tsukuba, Ibaraki, Japan. Editor(s): Yagasaki, Kazumi. Animal Cell Technology: Basic & Applied Aspects, Proceedings of the Annual Meeting of the Japanese Association for Animal Cell Technology, 15th, Fuchu, Japan, Nov. 11-15, 2002 (2003), Meeting Date 2002, 417-421. Publisher: Kluwer Academic Publishers, Dordrecht, Neth CODEN: 69GBKC Conference written in English. CAN 142:133721 AN 2004:962523 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Molecular genetics of ascochyta blight resistance in chickpea (cicer arietinum l.): genomic and biochemical dissection of quantitative resistance. Cho, Seungho. Washington State Univ., Pullman, WA, USA. Avail. UMI, Order No. DA3110850. (2003), 103 pp. From: Diss. Abstr. Int., B 2004, 64(11), 5330. Dissertation written in English. CAN 142:352188 AN 2004:981829 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoid glycosides, including flavane, flavanone, flavanol, flavone, isoflavone, and chalcone, with enzymic modification on their sugar chain are claimed as drugs and health foods for prevention and treatment of type-II diabetes.


flavanone

Anthocyanin, one of the flavonoids, is a primary determinant of red color in onions. Inheritance studies indicate that a single gene dets. the color difference between yellow and red onions. In order to establish which gene might be responsible for this color difference, full-length cDNAs of five structural genes: chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and flavonol synthase (FLS) were cloned using degenerate PCR and RACE (Rapid

Abstract

Inactivation of DFR (Dihydroflavonol 4-reductase) gene transcription results in blockage of anthocyanin production in yellow onions (Allium cepa). Kim, Sunggil; Binzel, Marla L.; Park, Sunghun; Yoo, Kil-Sun; Pike, Leonard M. Vegetable and Fruit Improvement Center, Department of Horticultural Sciences, Texas A & M University, TX, USA. Molecular Breeding (2004), 14(3), 253-263. Publisher: Kluwer Academic Publishers, CODEN: MOBRFL ISSN: 1380-3743. Journal written in English. CAN 142:457757 AN 2004:959662 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Orange peel molasses, a byproduct of juice prodn., contains high concns. of phenols, including numerous flavanone and flavone glycosides, polymethoxylated flavones, hydroxycinnamates, and other misc. phenolic glycosides and amines. Extensive fractionation of these phenols was achieved by adsorption, ion exchange, and size exclusion chromatog. Size exclusion chromatog. effectively sepd. the different classes of flavonoids in ultrafiltered molasses, including the polymethoxylated flavones, flavanone-O-trisaccharides, flavanone- and flavone-O-disaccharides, and, finally, flavone-C-glycosides. Mass spectral anal. of the early-eluting flavonoid fractions off the size exclusion column revealed a broad collection of minor-occurring flavone glycosides, which included, in part, glycosides of limocitrin, limocitrol, and chrysoeriol. Most hydroxycinnamates in the molasses were recovered by ion exchange chromatog., which also facilitated the recovery of fractions contg. many other misc. phenols. Total antioxidant levels and total phenolic contents were measured for the sep. categories of phenols in the molasses. Inhibition of the superoxide anion redn. of nitroblue tetrazolium showed that a significant amt. of the total antioxidant activity in orange peel molasses was attributable to minor-occurring flavones. The misc. phenolic-contg. fractions, in which a large portion of the total phenolic content in molasses occurred, also constituted a major portion of the total antioxidants in ultrafiltered molasses.

Abstract

Fractionation of orange peel phenols in ultrafiltered molasses and mass balance studies of their antioxidant levels. Manthey, John A. Citrus and Subtropical Products Laboratory, Southern Atlantic Area, Agricultural Research Service, U.S. Department of Agriculture, Winter Haven, FL, USA. Journal of Agricultural and Food Chemistry (2004), 52(25), 7586-7592. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 142:112802 AN 2004:961916 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(2), which showed antifungal activity against Candida albicans. Others were 3-farnesylindole (3), 2',6'-dihydroxy-3',4'-dimethoxy-chalcone (4), 2'-hydroxy-3',4',6'-trimethoxychalcone (5), 5-hydroxy-7,8-dimethoxyflavanone (6), 5,7,8-trimethoxyflavanone (7), and a 3 : 2 mixt. of 2',6'-dihydroxy-4'-methoxychalcone (8) and 5,7-dihydroxyflavone (9). Compd. 7 and the mixt. of compds. 8 and 9 showed antibacterial activity against Escherichia coli (NCTC 10418, MIC 125 μg/mL) and Staphylococcus aureus (MIC 125 μg/mL), resp. The mixt. of compds. 8 and 9 was also active against Candida albicans (MIC 31.25 μg/mL), Aspergillus niger, Aspergillus fumigatus, and the Penicillium species (MIC 1000 μg/mL). We conclude that Uvaria scheffleri exts. contain compds. with antifungal and antibacterial activity. The activities obsd. in this study are weak. Based on previous studies, it is being speculated that, possibly, the most active compds. were lost during fractionation. Further work to isolate more antifungal and antibacterial compds. is suggested.


flavanone

The expression of anthocyanin biosynthesis genes during flower color development in Anthurium andraeanum (anthurium) was studied. A cDNA library was constructed from mRNA from the anthurium spathe, and full-length cDNA clones were identified for the flavonoid

Abstract

Temporal and spatial expression of flavonoid biosynthetic genes in flowers of Anthurium andraeanum. Collette, Vern E.; Jameson, Paula E.; Schwinn, Kathy E.; Umaharan, Pathmanathan; Davies, Kevin M. New Zealand Institute for Crop and Food Research Limited, Palmerston North, N. Z. Physiologia Plantarum (2004), 122(3), 297-304. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 142:257822 AN 2004:954432 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


To elucidate gene regulation of flower color formation, the gene expressions of the enzymes involved in flavonoid biosynthesis were investigated in correlation with their product during floral development in lisianthus. Full-length cDNA clones of major responsible genes in the central flavonoid biosynthetic pathway, including chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), flavonoid 3',5'-hydroxylase (F3'5'H), dihydroflavonol 4-reductase (DFR), anthocyanidin synthase (ANS), and flavonol synthase (FLS), were isolated and characterized. In lisianthus, the stage of the accumulation of flavonols and anthocyanins was shown to be divided clearly. The flavonol content increased prior to anthocyanin accumulation during floral development and declined when anthocyanin began to accumulate. CHS, CHI, and F3H were necessary for both flavonol and anthocyanin biosynthesis and were coordinately expressed throughout all stages of floral development; their expressions were activated independently at the stages corresponding to flavonol accumulation and anthocyanin accumulation, resp. Consistent with flavonol and anthocyanin accumulation patterns, FLS, a key enzyme in flavonol biosynthesis, was expressed prior to the expression of the genes involved in anthocyanin biosynthesis. The genes encoding F3'5'H, DFR, and ANS were expressed at later stages, just before pigmentation. The genes responsible for the flavonoid pathways branching to anthocyanins and flavonols were strictly regulated and were coordinated temporally to correspond to the biosynthetic order of their resp. enzymes in the pathways, as well as in specific organs. In lisianthus, FLS and DFR, at the position of branching to flavonols and anthocyanins, were supposed to play a crit. role in regulation of each biosynthesis.

Abstract

Regulation of gene expression involved in flavonol and anthocyanin biosynthesis during petal development in lisianthus (Eustoma grandiflorum). Noda, Naonobu; Kanno, Yoshiaki; Kato, Naoki; Kazuma, Kohei; Suzuki, Masahiko. Aomori Green BioCenter, Aomori, Japan. Physiologia Plantarum (2004), 122(3), 305-313. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 142:151971 AN 2004:954433 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Amplification of cDNA Ends). RT-PCR was carried out for these five genes to examine differential expression between yellow and red colored bulbs. Accumulation of the DFR gene transcript only occurred in red onions. In F3 populations which originated from the cross between yellow and red parents, DFR transcript was detected only in red F3 lines. To design mol. markers for selection of yellow and red DFR alleles, the DFR gene was sequenced from genomic DNA isolated from both types of onions. The genomic DNA sequence revealed the DFR gene consists of six exons and five introns. A PCR-RFLP marker was designed based on 2% polymorphic nucleotide sequence of the DFR gene between yellow and red onions. The co-segregation of markers and red color were obsd. in F2 segregating populations, supporting the conclusion that color difference in red and yellow onions is likely to be due to the lack of an active DFR gene.


flavanone

In the present study, we tried to investigate whether phorbol myristate acetate (PMA), trihydroxymethoxyflavanone rutinoside (TFR) and cationic polypeptides significantly affect mucin release (secretion) from cultured hamster tracheal surface epithelial cells. Confluent primary hamster tracheal surface epithelial (HTSE) cells were metabolically radiolabeled with 3H-glucosamine for 24 h and chased for 30 min in the presence of each agent to assess the effect on 3H-mucin release. The results were as follows: (1) Both PMA and TFR significantly increased mucin release from cultured HTSE cells: (2) Cationic polypeptides including poly-L-lysine (PLL, mw 7,500) and poly-L-arginine (PLA, mw 10,800) significantly inhibited mucin release from cultured HTSE cells, in a dose-dependent manner. This finding suggests us that PMA and TFR be further studied for the possible use as mild expectorants and cationic

Abstract

Effects of several agents on mucin release from cultured airway epithelial cells of rodents. Lee, Choong-Jae; Seok, Jeong-Ho; Lee, Jae-Heun; Hur, Gang-Min; Park, Ji-Sun; Bae, So-Hyun; Row, Sam-Gil; Park, Sang-Cheol. Department of Pharmacology, College of Medicine, Chungnam National University, S. Korea. Chungnam Uidae Chapchi (2003), 30(2), 45-53. Publisher: Chungnam National University, College of Medicine, CODEN: CUCHDS ISSN: 0253-6307. Journal written in Korean. CAN 142:385560 AN 2004:951451 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The flavanone naringenin (Nar), esp. abundant in the Mediterranean diet, is reported to have antiproliferative effects in many cancer cell lines. Antioxidant activities, kinase and glucose uptake inhibition have been proposed as mol. mechanisms for these effects. In addn., an antiestrogenic activity has been obsd. but, at the present, it is poorly understood whether this latter activity could play a role in the Nar antitumoral effects. Here, the authors tested the ability of Nar to activate a specific, rapid signal transduction pathway committed to the generation of an apoptotic cascade in the presence of one of the two estrogen receptor (ER) isoforms (i.e., ERα or ERβ). Cancer cells contg. transfected (human cervix epitheloid carcinoma HeLa cells) or endogenous ERα (human hepatoma HepG2 cells) or ERβ (human colon adenocarcinoma DLD-1 cells) were used. Our results show that Nar exerts an antiproliferative effect only in the presence of ERα or ERβ. Moreover, Nar stimulation induces the activation of p38/MAPK leading to the pro-apoptotic caspase-3 activation and to the poly(ADP-ribose) polymerase cleavage in all cancer cell lines considered. Notably, Nar shows an antiestrogenic effect only in ERα contg. cells; whereas in ERβ contg. cells, Nar mimics the 17β-estradiol effects. These findings indicate new steps in the mechanism underlying ER-dependent antiproliferative effects of Nar suggesting new potential chemopreventive actions of flavonoids on cancer growth.

Abstract

Mechanisms of Naringenin-induced Apoptotic Cascade in Cancer Cells: Involvement of Estrogen Receptor α and β Signalling. Totta, Pierangela; Acconcia, Filippo; Leone, Stefano; Cardillo, Irene; Marino, Maria. Dept. Biol., University Roma Tre, Rome, Italy. IUBMB Life (2004), 56(8), 491-499. Publisher: Taylor & Francis Ltd., CODEN: IULIF8 ISSN: 1521-6543. Journal written in English. CAN 142:86072 AN 2004:954022 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


biosynthetic enzymes chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR) and anthocyanidin synthase (ANS). These were used to measure transcript levels in the spathe during flower development, in cultivars with different flower colors, over the diurnal cycle, and in the spadix. CHS, F3H and ANS were expressed at all stages of spathe and spadix development. However, DFR transcript levels varied significantly between stages, and DFR may represent a key point of regulation. A diurnal rhythm of DFR transcript abundance in the spathe was also obsd., with transcript levels high at dawn and dusk and low at noon. Control of anthocyanin biosynthesis in anthurium spathe differs from that described for flowers of other species, with DFR a key regulatory point and a complex mix of developmental and environmental control signals.


flavanone

Answer 721:

From the herb of Galium fissurense, a new flavanone glucoside was isolated and characterized as 5,7,3'-trihydroxyflavanone-4'-O-β-D-glucopyranoside (1) from spectroscopic evidence. In addn., three known compds. (luteolin, apigenin-7-O-β-D-glucopyranoside, naringenin-7-O-β-D-glucopyranoside) were isolated for the first time from this plant. The free radical scavenging properties of the four compds. were studied by use of in vitro ESR spectrometry. The new compd. showed potent antioxidant activity.

Abstract

Novel flavanone glucoside with free radical scavenging properties from Galium fissurense. Orhan, D. Deliorman. Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, Ankara, Turk. Pharmaceutical Biology (Lisse, Netherlands) (2003), 41(7), 475-478. Publisher: Swets & Zeitlinger B.V., CODEN: PHBIFC ISSN: 1388-0209. Journal written in English. CAN 142:468999 AN 2004:925371 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Species of the genus Citrus accumulate large quantities of flavanones that affect fruit flavor and have been documented to benefit human health. Bitter species, such as grapefruit and pummelo, accumulate bitter flavanone-7-O-neohesperidosides responsible, in part, for their characteristic taste. Non-bitter species, such as mandarin and orange, accumulate only tasteless flavanone-7-O-rutinosides. The key flavor-detg. step of citrus flavanone-glycoside biosynthesis is catalyzed by rhamnosyltransferases; 1,2 rhamnosyltransferases (1,2RhaT) catalyze biosynthesis of the bitter neohesperidosides, while 1,6 rhamnosyltransferases (1,6RhaT) catalyze biosynthesis of the tasteless rutinosides. The authors report on the isolation and functional characterization of the gene Cm1,2RhaT from pummelo which encodes a citrus 1,2RhaT. Functional anal. of Cm1,2RhaT recombinant enzyme was conducted by biotransformation of the substrates using transgenic plant cell culture. Flavanones and flavones, but not flavonols, were biotransformed into 7-O-neohesperidosides by the transgenic BY2 tobacco cells expressing recombinant Cm1,2RhaT. Immunoblot anal. established that 1,2RhaT protein was expressed only in the bitter citrus species and that 1,6RhaT enzyme, whose activity was previously documented in non-bitter species, was not cross-reactive. Expression of Cm1,2RhaT at the RNA level was prominent in young fruit and leaves, but low in the corresponding mature tissue, thus correlating well with the developmental pattern of accumulation of flavanone-neohesperidosides previously established. Phylogenetic anal. of the flavonoid glycosyltransferase gene family places Cm1,2RhaT on a sep. gene cluster together with the only other functionally characterized flavonoid-glucoside rhamnosyltransferase gene, suggesting a common evolutionary origin for rhamnosyltransferases specializing in glycosylation of the sugar moieties of flavonoid glucosides.

Abstract

Citrus fruit bitter flavors: isolation and functional characterization of the gene Cm1,2RhaT encoding a 1,2 rhamnosyltransferase, a key enzyme in the biosynthesis of the bitter flavonoids of citrus. Frydman, Ahuva; Weisshaus, Oori; Bar-Peled, Maor; Huhman, David V.; Sumner, Lloyd W.; Marin, Francisco R.; Lewinsohn, Efraim; Fluhr, Robert; Gressel, Jonathan; Eyal, Yoram. Institute of Horticulture, The Volcani Center, ARO, Bet-Dagan, Israel. Plant Journal (2004), 40(1), 88-100. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 143:91696 AN 2004:950358 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


polypeptides, might function as a regulator for hypersecretion of mucus, both by direct acting on airway mucin-secreting cells, during the treatment of chronic airway diseases.


flavanone

Conversion from Arenes Having a Benzene Ring to Those Having a Picolinic Acid by Simple Growing Cell Reactions Using Bibliographic Information Answer 723:

Lipase Candida cylindracea (CCL) catalyzed acylation of (±)-cis-flavan-4-ols using vinyl acetate as the acyldonor in DME-toluene (1:2) gave (-)-(2R,4R)-4-acetoxyflavans and (+)-(2S,4S)-flavan-4-ols in high enantiomeric excess. (+)-(2S,4S)-Flavan-4-ols were converted to (-)-(2S)-flavan-4-ones.

Abstract

Enantioselective acylation of (±)-cis-flavan-4-ols catalyzed by lipase from Candida cylindracea (CCL) and the synthesis of enantiopure flavan-4-ones. Ramadas, Sathunuru; Krupadanam, G. L. David. Department of Chemistry, Osmania University, Hyderabad, India. Tetrahedron: Asymmetry (2004), 15(21), 3381-3391. Publisher: Elsevier B.V., CODEN: TASYE3 ISSN: 0957-4166. Journal written in English. CAN 142:93551 AN 2004:920914 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Provided are flavanone derivs. which decrease blood lipid level, inhibits cholesterol metab. related enzyme, treat and prevent arteriosclerosis, and protect liver function. Also, provided are a compn. for preventing or treating blood lipid level-related diseases comprising same. The flavanone deriv. having excellent improving effects on lipid metab. is represented by the formula(1), wherein R1 is R5 or R6CO-; R2 is H or R6CO-; R3 is H, CH3, R5 or R6CO-; R4 is H, OH, OR5 or R6COO-; R5 is unsubstituted or substituted C2-C5 alkyl with Ph which is substituted with at least one of C1-C3 alkyl, OH, Cl or NO2, unsubstituted or substituted C1-C5 alkyl with substituted naphthyl which is substituted with at least one of C1-C3 alkyl, OH, Cl or NO2, or C10-18 alkyl or alkenyl; and R6 is C10-18 alkenyl or unsubstituted or substituted aryl with at least one of C1-3 alkyl, OH or NO2.


Preparation of flavanone derivatives and composition for preventing or treating blood lipid level-related diseases. Bok, Seong Hae; Choi, Myeong Suk; Choi, Yang Gyu; Hyun, Byeong Hwa; Jung, Tae Suk; Kim, Ju Ryeong; Lee, Cheol Ho; Lee, Sang Gu; Mun, Seok Sik. (Korea Research Institute of Bioscience and Biotechnology, S. Korea). Repub. Korean Kongkae Taeho Kongbo (2002), No pp. given. CODEN: KRXXA7 KR 2002059027 A 20020712 Patent written in Korean. Application: KR 2000-87185 20001230. Priority: . CAN 142:113896 AN 2004:924419 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone


Protein and cDNA sequences of novel chalcone synthase (CHS), dihydroflavonol 4-reductase (BAN) and leucoanthocyanidin reductase (LAR) from Trifolium repens flavanone and use for stress-resistance plant. Spangenberg, German; Emmerling, Michael; Simmonds, Jason; Winkworth, Amanda; Panter, Stephen. (Agriculture Victoria Services Pty Ltd, Australia; Agresearch Limited). PCT Int. Appl. (2004), 117 pp. CODEN: PIXXD2 WO 2004090136 A1 20041021 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2004-AU494 20040414. Priority: AU 2003-901797 20030414; AU 2003-904369 20030814. CAN 141:344617 AN 2004:872846 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The Et acetate ext. of the stem bark of Erythrina abyssinica showed anti-plasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 7.9±1.1 and 5.3±0.7 μg/mL, resp. From this ext., a new chalcone, 2',3,4,4'-tetrahydroxy-5-prenylchalcone (trivial name 5-prenylbutein) and a new flavanone, 4',7-dihydroxy-3'-methoxy-5'-prenylflavanone (trivial name, 5-deoxyabyssinin II) along with known flavonoids have been isolated as the anti-plasmodial principles. The structures were detd. on the basis of spectroscopic evidence.

Abstract

Anti-plasmodial flavonoids from the stem bark of Erythrina abyssinica. Yenesew, Abiy; Induli, Martha; Derese, Solomon; Midiwo, Jacob O.; Heydenreich, Matthias; Peter, Martin G.; Akala, Hoseah; Wangui, Julia; Liyala, Pamela; Waters, Norman C. Department of Chemistry, University of Nairobi, Nairobi, Kenya. Phytochemistry (Elsevier) (2004), 65(22), 3029-3032. Publisher: Elsevier B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 142:71494 AN 2004:886419 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The comprehensive bioconversion of arom. compds. with a benzene ring to a picolinic acid was achieved with a recombinant Escherichia coli strain that expressed the six genes involved in biphenyl catabolism, these being the bphA1(2072)A2A3A4 genes encoding the evolved biphenyl dioxygenase, the bphB gene encoding dihydrodiol dehydrogenase, and the bphC gene encoding catechol 2,3-dioxygenase.

Abstract

Escherichia coli that Expressed the Six Bacterial Genes Involved in Biphenyl Catabolism. Shindo, Kazutoshi; Osawa, Ayako; Nakamura, Ryoko; Kagiyama, Yukiko; Sakuda, Shohei; Shizuri, Yoshikazu; Furukawa, Kensuke; Misawa, Norihiko. Department of Food and Nutrition, Japan Women's University, Tokyo, Japan. Journal of the American Chemical Society (2004), 126(46), 15042-15043. Publisher: American Chemical Society, CODEN: JACSAT ISSN: 0002-7863. Journal written in English. CAN 142:73462 AN 2004:902886 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Kurarinone, a lavandulyl flavanone, was isolated from a polyphenolic ext. of the roots of Sophora flavescens using fractionation guided by estrogenic activity, which was detd. by recombinant yeast and Ishikawa Var-I bioassays. Kurarinone showed weak estrogenic activity both in the yeast screen and in the Ishikawa Var-I assay with EC50 values of 4.6 and 1.66 μM, resp. Furthermore, kurarinone was found to have potent cytotoxic activity (IC50 value = 22.2 μM) against human MCF-7/6 breast cancer cells in the sulforhodamine-B assay.

Abstract

Estrogenic and Anticarcinogenic Properties of Kurarinone, a Lavandulyl Flavanone from the Roots of Sophora flavescens. De Naeyer, An; Vanden Berghe, Wim; Pocock, Victoria; Milligan, Stuart; Haegeman, Guy; De Keukeleire, Denis. Laboratory of Pharmacognosy and Phytochemistry, Faculty of Pharmaceutical Sciences, Ghent University, Ghent, Belg. Journal of Natural Products (2004), 67(11), 1829-1832. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 142:11348 AN 2004:866543 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The present invention relates to nucleic acid fragments encoding amino acid sequences for flavonoid biosynthetic enzymes in plants, and the use thereof for the modification of, for example, flavonoid biosynthesis in plants, and more specifically the modification of the content of condensed tannins. In particularly preferred embodiments, the invention relates to the combinatorial expression of chalcone synthase (CHS) and/or dihydroflavonol 4-reductase (BAN) and/or leucoanthocyanidin reductase (LAR) in plants to modify, for example, flavonoid biosynthesis or more specifically the content of condensed tannins.

Abstract WO 2004-AU494 W 20040414AU 2003-904369 A 20030814AU 2003-901797 A 20030414Priority Application US 20060195920 A1 20060831 US 2005-552857 20051014 NZ 542732 A 20080131 NZ 2004-542732 20040414



RW: BW, GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG


WO 2004090136 A1 20041021 WO 2004-AU494 20040414


flavanone

A procedure for the synthesis of 2,3-dihydro-2-phenyl-4-quinolinones, e.g., I, is reported. Anilines underwent condensation with Et benzoylacetate followed by heterocyclization to give the corresponding 2,3-dihydro-2-phenyl-4-quinolinones in good yields.

Abstract

Synthesis of new 2,3-dihydro-2-phenyl-4-quinolone derivatives; Aza analogs of flavanone. Park, Myung-Sook; Lee, Jae-In. College of Pharmacy, Duksung Women's University, Seoul, S. Korea. Bulletin of the Korean Chemical Society (2004), 25(8), 1269-1272. Publisher: Korean Chemical Society, CODEN: BKCSDE ISSN: 0253-2964. Journal written in English. CAN 142:261383 AN 2004:846710 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids are a large family of compds. assocd. with many biol. activities (e.g., antioxidant, estrogenic, antiinflammatory properties). Until now, the most examd. (iso)flavonoids with respect to bone health are the soy isoflavones, which have been shown to prevent bone loss in the ovariectomized rat and attenuate spinal bone loss in postmenopausal women. Citrus fruits are rich in flavanones. Hesperidin (Hp), is one of the main flavanones in oranges. The authors investigated its effect on bone metab. in intact and ovariectomized rats. The study was carried out on 40 3-mo-old Wistar female rats; 20 were sham operated (SH), while the others were ovariectomized (OVX). Among each group, 10 sham-operated (TSH) and 10 ovariectomized (TOVX) rats were fed a std. diet for 90 days following surgery, and the 20 remaining animals received the same regimen but with 0.5% hesperidin added (10 HpSH, 10 HpOVX). At necropsy, the ovariectomy-induced uterine wt. decrease did not differ between TOVX and HpOVX rats. Hesperidin consumption totally prevented the ovariectomy-induced demineralization (bone mineral d. TOVX: -6.2% vs. TSH; HpOVX vs. TSH: NS; HpOVX: +10.7% vs. TOVX), and significantly improved femoral metaphyseal d. (HpSH: +11.5% vs. TSH) in intact rats as well. The femoral diaphyseal d. was also significantly enhanced by hesperidin in both SH and OVX rats, while an improvement of bone strength was only obsd. in ovariectomized animals. Plasma osteocalcin concns. were higher in HpOVX (P < 0.05 vs. HpSH). Urinary deoxypyridinolin excretion was reduced (P < 0.01) in both HpSH and HpOVX rats compared to their controls. Finally, the plasma concn. of hesperetin (the aglycon form) was 12.53 ± 2.48 μM in hesperidin fed rats, bile the mol. stayed undetectable in control rats. These results indicate that, under our exptl. conditions, hesperidin consumption was able to improve bone mass acquisition in intact rats and exhibited a significant protection against ovariectomy-induced bone impairment.

Abstract

Hesperidin, a citrus flavanone, improves bone acquisition and prevents skeletal impairment in rats. Horcajada, Marie-Noelle; Coxam, Veronique. Unite des Maladies Metaboliques et Micronutriments, Groupe Osteoporose, INRA de Theix, Fr. Editor(s): Burckhardt, Peter; Dawson-Hughes, Bess; Heaney Robert P. Nutritional Aspects of Osteoporosis, [International Symposia on Nutritional Aspects of Osteoporosis], 5th, Lausanne, Switzerland, May 14-17, 2003 (2004), Meeting Date 2003, 109-126. Publisher: Elsevier, San Diego, Calif CODEN: 69FZF6 Conference written in English. CAN 142:92943 AN 2004:860105 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

A review. There are many epigenetic variables that affect the biol. responses of autocrine, paracrine and endocrine regulatory mols., which det. the growth and development of different cancers including prostate cancer (PCA). One of the focuses of the current cancer chemoprevention studies is the search for non-toxic chemopreventive agents that inhibit mitogenic and cell survival signaling in cancer cells. In general, advanced stage cancer cells harbor many constitutively active mitogenic signaling and anti-apoptotic mechanisms, which make them less dependent on external growth factors as well as resistant to chemotherapeutic agents. In this regard, silibinin (a naturally occurring flavanone) has shown the pleiotropic anticancer effects in different cancer cells. Our extensive studies with PCA have shown that inhibition of mitogenic and cell survival signaling, such as epidermal growth factor receptor, insulin-like growth factor receptor type I and nuclear factor kappa B signaling are the most likely mol. targets of silibinin's efficacy in PCA. We have obsd. that silibinin inhibits prostate tumor growth in animal models without any apparent signs of toxicity. At the same time, silibinin is also

Abstract

A cancer chemopreventive agent silibinin, targets mitogenic and survival signaling in prostate cancer. Singh, Rana P.; Agarwal, Rajesh. Department of Pharmaceutical Sciences, School of Pharmacy, University of Colorado Health Sciences Center, Denver, CO, USA. Mutat. Res. (2004), 555(1-2), 21-32. Publisher: Elsevier B.V., CODEN: MUREAV ISSN: 0027-5107. Journal; General Review written in English. CAN 141:360124 AN 2004:829293 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The relationship between the structure of 14 phenolic compds. and their molluscicidal activity against the molluscan intermediate host of urinary schistosomiasis, Bulinus truncatus, is discussed. It was found that among flavonoids tested, unhydroxylated flavone compd. and flavanone hesperidin were the most active (LC50 = 5.47 and 8.91 ppm, resp.), whereas gallic acid compd. with para-methoxy group was the most effective among phenolic acids tested (LC50 = 3.60 ppm). These results are encouraging and prove other biol. application of these compds.

Abstract

Study of the molluscicidal activity of some phenolic compounds: structure-activity relationship. Lahlou, Mouhssen. Laboratoire de Biochimie, Biologie Cellulaire et Moleculaire, Departement de Biologie, Unite de Formation et de Recherche: Biologie et Sante, Faculte des Sciences Ain Chock, Casablanca, Morocco. Pharmaceutical Biology (Lisse, Netherlands) (2004), 42(3), 258-261. Publisher: Taylor & Francis The Netherlands, CODEN: PHBIFC ISSN: 1388-0209. Journal written in English. CAN 142:387584 AN 2004:837081 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


N

O

MeO

H I


flavanone

Flavonoid biosynthesis in the tea plant Camellia sinensis: properties of enzymes of the prominent epicatechin and catechin pathways. Punyasiri, P. A. N.; Abeysinghe, I. S. B.; Kumar, V.; Treutter, D.; Duy, D.; Gosch, C.; Martens, S.; Forkmann, G.;


Compns. and methods for therapy of cystic fibrosis, asthma, and other conditions characterized by defective chloride transport a re provided. The compns. comprise one or more compds. such as flavones and/or isoflavones, ascorbate and/or derivs. thereof capable of stimulating chloride transport in epithelial tissues. Therapeutic methods involve the administration (e.g., orally or via inhalation) of such compns. to a patient afflicted with cystic fibrosis, asthma, and/or another condition responsive to stimulation of chloride transport. For example, L-ascorbic acid was found to be able to stimulate the CFTR activity through a cAMP mediated pathway.

Abstract EP 1998-953609 A3 19981016US 2001-982315 A2 20011017US 1998-174077 A3 19981016US 1997-951912 A2 19971016Priority Application US 7335683 B2 20080226US 20030096762 A1 20030522 US 2001-982315 20011017

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, FI, CYEP 1669067 A3 20061122EP 1669067 A2 20060614 EP 2005-17863 19981016US 6329422 B1 20011211 US 1998-174077 19981016US 5972995 A 19991026 US 1997-951912 19971016US 20040197272 A1 20041007 US 2004-769619 20040130Patent No. Kind Date Application No. Date Patent Family Information

Compositions and methods for therapy for diseases characterized by defective chloride transport. Fischer, Horst; Illek, Beate. (Children's Hospital Oakland, USA). U.S. Pat. Appl. Publ. (2004), 69 pp., Cont.-in-part of U.S. Ser. No. 982,315. CODEN: USXXCO US 2004197272 A1 20041007 Patent written in English. Application: US 2004-769619 20040130. Priority: US 97-951912 19971016; US 98-174077 19981016; US 2001-982315 20011017. CAN 141:320085 AN 2004:824855 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


physiol. available in different organs of the body including plasma and prostate, which is generally required for the pharmacol. dosing and translational mechanistic studies of the compd. There are substantial amt. of data to support the inhibitory effect of silibinin on mitogenic and cell survival signaling in PCA, which are reviewed in the present communication.


flavanone

Enzymic manufacture of aromatic diols from phenyl-containing aromatic compounds. Misawa, Norihiko; Shindo, Kazutoshi. (Marine Biotechnology Institute Co. Ltd., Japan). PCT Int. Appl. (2004), 90 pp. CODEN: PIXXD2 WO 2004078988 A1 20040916 Designated States W: AE. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT,


Petals of Osteospermum exhibit white, yellow and rose to lilac colors. Chem. and biochem. investigations elucidated the basis of flower color in Osteospermum. Besides carotenoids, which were shown to be responsible for the yellow color, flavonoids were identified to be the main color-giving compds. Different amts. of derivs. of the anthocyanidin delphinidin cause the rose to lilac color range. In addn. to delphinidin, derivs. of flavonols were found to be present in the petals. Enzyme assays elucidated the biosynthetic path leading to the formation of the 3'-, 4'-, and 5'-hydroxylated delphinidin. Because of distinct substrate specifities of the early enzymes of the flavonoid pathway, chalcone synthase, chalcone isomerase, and flavanone 3-hydroxylase, dihydrokaempferol is supposed to be the main branch point. This compd. was shown to be hydroxylated in 3'- and 5'- position by flavonoid 3', 5'-hydroxylase to dihydromyricetin which is subsequently reduced by dihydroflavonol 4-reductase to leucodelphinidin, the precursor of delphinidin. Mol. biol. investigations of two key steps allowed a confirmation of the enzymol. findings. The protein of a heterologously expressed full length chalcone synthase cDNA-clone was shown to preferentially use 4-coumaroyl-CoA as a substrate leading to the formation of naringenin after isomerisation by chalcone isomerase. In contrast to this, caffeoyl-CoA as a substrate resulted in the formation of only low amts. of eriodictyol. 3', 5'-Hydroxylation, which is indispensable for the formation of delphinidin, was demonstrated with the protein of a heterologously expressed F3'5'H full-length cDNA-clone. Fragments of the other main structural flavonoid genes of Osteospermum are now available and further mol. biol. investigation will be performed.

Abstract

Cloning and heterologous expression of flavonoid genes of Osteosopermum hybrids. Seitz, C.; Hauser, A.; Forkmann, G.; Martens, S. Department for Plant Sciences, Chair for Floriculture Crops and Horticultural Plant Breeding, Tu Muenchen, Freising, Germany. Acta Horticulturae (2004), 651(Proceedings of the 21st International Symposium on Classical Versus Molecular Breeding of Ornamentals, Part II, 2003), 107-114. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 142:149344 AN 2004:796009 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Leaves of tea (Camellia sinensis L.) contain extraordinary large amts. of (-)-epigallocatechin, (-)-epicatechin, (+)-gallocatechin, and (+)-catechin and derivs. of these compds. that show pos. effects on human health. The health-promoting effects of flavan-3-ols, esp. those of green tea, are of scientific and public interest. Furthermore, they play a crucial role in defense against pathogens of tea. Therefore, biosynthesis of these flavonoid compds. was investigated. The anthocyanidin reductase (ANR) enzyme recently described from Arabidopsis and Medicago was shown to be present in tea with very high activity. The nonradioactive ANR assay developed included HPLC anal. of reaction products; the enzyme produced epicatechin as well as epigallocatechin from the resp. anthocyanidins, thus explaining the very high contents of these compds. A strong combined dihydroflavonol 4-reductase/leucoanthocyanidin 4-reductase activity was demonstrated and catalyzed the key steps in catechin and gallocatechin formation. Together with the enzyme activities and substrate specificities of the preceding enzymic reactions, the biosynthesis of the most prominent flavonoids of tea is elucidated.

Abstract

Fischer, T. C. Biochemistry Division, Tea Research Institute of Sri Lanka, Talawakelle, Sri Lanka. Archives of Biochemistry and Biophysics (2004), 431(1), 22-30. Publisher: Elsevier, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN 142:52255 AN 2004:819364 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Phenolic profile and antioxidant activity of the Algerian ripe date palm fruit (Phoenix dactylifera). Mansouri, Abdelhak; Embarek, Guendez; Kokkalou, Eugene; Kefalas, Panagiotis. Laboratory of Chemistry of Natural Products, Department of Food Quality Management, Mediterranean Agronomic Institute of Chania (MAICh), Crete, Chania, Greece. Food Chemistry (2004), Volume Date 2005, 89(3), 411-420. Publisher: Elsevier B.V., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 142:5748 AN 2004:745165 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review on more than 450 newly reported compds. belonging to eight different classes of flavonoids recorded in the literature from Jan. 2001 to Dec. 2003. Brief mention is made of relevant data on the biol. activity of these flavonoids as cited in the original papers.

Abstract

Anthocyanins and other flavonoids. Williams, Christine A.; Grayer, Renee J. Plant Science Laboratories, The University of Reading, Reading, UK. Natural Product Reports (2004), 21(4), 539-573. Publisher: Royal Society of Chemistry, CODEN: NPRRDF ISSN: 0265-0568. Journal; General Review written in English. CAN 142:332850 AN 2004:746645 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The arom. diols which are useful antioxidants are manufd. from Ph group-contg. arom. compds. with arom. ring dioxygenase and arom. ring dihydrodiol desaturase, or (recombinant) microorganism producing the enzymes. Manuf. of arom. diol. 2-(2,3-dihydroxyphenyl)chromen-4-one from flavone with recombinant Escherichia coli harboring plasmid pBS2072B was shown.

Abstract JP 2003-57867 A 20030304Priority Application

RW: BW, GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI


SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in Japanese. Application: WO 2004-JP2654 20040303. Priority: JP 2003-57867 20030304. CAN 141:259473 AN 2004:756888 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. Kanaze, Feras Imad; Kokkalou, Eugene; Georgarakis, Manolis; Niopas, Ioannis. Department of Pharmacy, School of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki, Greece. Journal of Pharmaceutical and Biomedical Analysis (2004), 36(1), 175-181. Publisher: Elsevier B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 142:193597 AN 2004:733521 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. Previous collaborative work by our group has led to the discovery of several plant isolates and derivs. with activities in in vivo models of cancer chemoprevention, including deguelin, resveratrol, bruceantin, brassinin, 4'-bromoflavone, and oxomate. Using a panel of in vitro bioassays to monitor chromatog. fractionation, a diverse group of plant secondary metabolites has been identified as potential cancer chemopreventive agents from mainly edible plants. Nearly 50 new compds. have been isolated as bioactive principles in one or more in vitro bioassays in work performed over the last five years. Included among these new active compds. are alkaloids, flavonoids, stilbenoids, and withanolides, as well as a novel stilbenolignan and the first representatives of the norwithanolides, which have a 27-carbon atom skeleton. In addn., over 100 active compds. of previously known structure have been obtained. Based on this large pool of potential cancer chemopreventive compds., structure-activity relationships are discussed in terms of the quinone reductase induction ability of flavonoids and withanolides and the cyclooxygenase-1 and -2 inhibitory activities of flavanones, flavones and stilbenoids. Several of the bioactive compds. were active when evaluated in a mouse mammary organ culture assay, when used as a secondary discriminator in our work. The compds. (2S)-abyssinone II, (2S)-2',4'-dihydroxy-2''-(1-hydroxy-1-methylethyl)dihydrofuro[2,3-h]-flavanone, 3'-[γ-hydroxymethyl-(E)-γ-methylallyl]-2,4,2',4'-tetrahydroxychalcone 11'-O-coumarate, isolicoflavonol, isoliquiritigenin, and ixocarpalactone A are regarded as promising leads as potential cancer chemopreventive agents.

Abstract

Natural inhibitors of carcinogenesis. Kinghorn, A. Douglas; Su, Bao-Ning; Jang, Dae Sik; Chang, Leng Chee; Lee, Dongho; Gu, Jian-Qiao; Carcache-Blanco, Esperanza J.; Pawlus, Alison D.; Lee, Sang Kook; Park, Eun Jung; Cuendet, Muriel; Gills, Joell J.; Bhat, Krishna; Park, Hye-Sung; Mata-Greenwood, Eugenia; Song, Lynda L.; Jang, Meishiang; Pezzuto, John M. Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA. Planta Medica (2004), 70(8), 691-705. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal; General Review written in English. CAN 141:235488 AN 2004:742602 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The aim of this study was to det. the phenolic profile of seven different varieties of ripe date palm fruit (Phoenix dactylifera) from Algeria by LC-DAD-MS (ESI+), to investigate their resp. antioxidant activities by the DPPH⋅ method and to est. their phenolic content using the Folin-Ciocalteu method. The total phenolic content was in the range of 2.49±0.01 to 8.36±0.60 mg gallic acid equiv. (GAE) per 100 g fresh fruit. This fruit was shown to possess an antioxidant activity, giving values of antiradical efficient (AE) from 0.08±0.00 to 0.22±0.00. The phenolic contents and the antiradical efficiencies of the different varieties were highly correlated (R2 = 0.975). All the varieties were found to contain mainly p-coumaric, ferulic and sinapic acids and some cinnamic acid derivs. Three different isomers of 5-o-caffeoylshikimic acid were detected. Different types of flavonoids were identified, mainly flavones, flavanones and flavonol glycosides.

Abstract


flavanone

Comprehensive Study on Vitamin C Equivalent Antioxidant Capacity (VCEAC) of Various Polyphenolics in Scavenging a Free Radical and its Structural Relationship. Kim, Dae-Ok; Lee, Chang. Department of Food Science and Technology, Cornell University, Geneva, NY, USA. Critical Reviews in Food Science and Nutrition (2004), 44(4), 253-273. Publisher: Taylor &


A flavanone and a flavanone glycoside, together with vomifoliol, have been isolated for the first time from the aerial parts of the plant Echiochilon fruticosum and identified. Their structures were established on the basis of spectroscopic measurements, mainly 2D NMR using COSY, HMQC and HMBC expts.

Abstract

Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing in Tunisia. Hammami, S.; Ben Jannet, H.; Bergaoui, A.; Ciavatta, L.; Cimino, G.; Mighri, Z. Faculte des Sciences de Monastir, Laboratoire de Chimie des Substances Naturelles et de Synthese Organique, Monastir, Tunisia. Molecules (2004), 9(7), 602-608. Publisher: Molecular Diversity Preservation International, CODEN: MOLEFW ISSN: 1420-3049. http://www.mdpi.net/molecules/papers/90700602.pdf Journal; Online Computer File written in English. CAN 142:332890 AN 2004:719023 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new dihydroflavone glycoside was isolated from the underground parts of Glycyrrhiza uralensis. Its structure was elucidated as 7-hydroxyl-4'-O-β-D-(6''-O-α-hydroxylpropionyl) glucopyranosyl dihydroflavone by spectral methods.

Abstract

A new dihydroflavone glycoside from Glycyrrhiza uralensis. Liu, Hong Xia; Lin, Wen Han; Yang, Jun Shan. Institute of Medicinal Plant Development, Chinese Academy of Medical Science and Peking Union Medical College, Beijing, Peop. Rep. China. Chinese Chemical Letters (2004), 15(8), 925-926. Publisher: Chinese Chemical Society, CODEN: CCLEE7 ISSN: 1001-8417. Journal written in English. CAN 142:173310 AN 2004:725267 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A simple, specific, precise, accurate, and robust HPLC assay for the simultaneous anal. of hesperetin and naringenin in human urine was developed and validated. Urine samples were incubated with β-glucuronidase/sulfatase and the analytes were isolated by solid-phase extn. using C18 cartridges and sepd. on a C8 reversed phase column using a mixt. of methanol/water/acetic acid (40:58:2, vol./vol./v) at 45°. The method was found to be linear in the 50-1200 ng/mL concn. range for both hesperetin and naringenin (r > 0.999). The accuracy of the method was greater than 94.8%, while the intra- and inter-day precision for hesperetin was better than 4.9 and 8.2%, resp. and for naringenin was better than 5.3 and 7.8%, resp. Recovery for hesperetin, naringenin and internal std. 7-ethoxycoumarin was greater than 70.9%. The method has been applied for the detn. of hesperetin and naringenin in urine samples obtained from a male volunteer following a single 300 mg oral dose of each of the corresponding flavanone glycosides hesperidin and naringin. The intra- and inter-day reproducibility through enzyme hydrolysis was less than 3.9% for both total (free + conjugated) hesperetin and naringenin. Stability studies showed urine quality control samples to be stable for both hesperetin and naringenin through three freeze-thaw cycles and at room temp. for 24 h (error ≤ 3.6%).


flavanone

Purpose: It has been found that the no. of hydroxy groups in the mol. of flavones and flavanones affect the ocular blood flow Abstract

Effects of Dihydrogenation of Flavones and Number of Hydroxy Groups in the Molecules on Ocular Blood Flow in Rabbits and Retinal Function Recovery in Rats. Xu, Xin-Rong; Park, Young-Hyun; Chiou, George C. Y. Institute of Ocular Pharmacology and Department of Medical Pharmacology and Toxicology, Health Science Center College of Medicine, Texas A&M University System, College Station, TX, USA. Journal of Ocular Pharmacology and Therapeutics (2004), 20(4), 311-320. Publisher: Mary Ann Liebert, Inc., CODEN: JOPTFU ISSN: 1080-7683. Journal written in English. CAN 141:253664 AN 2004:682853 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Deuterium incorporation at the C-3 position of flavanones was achieved by treatment of flavanones and 2'-hydroxychalcones with D3PO4 and AcOD. The deuteration reaction mechanism for 2'-hydroxychalcones substrates is as follows. In the first step, 2'-hydroxychalcones cyclize to the corresponding flavanones by an intramol. Michael-type reaction. Then deuteriums are incorporated into the flavanones via enolization.

Abstract

Synthesis of deuterium-labeled flavanones. Kagawa, Hitoshi; Takahashi, Tetsuya; Uno, Mariko; Ohta, Shigeru; Harigaya, Yoshihiro. Department of Organic Synthesis, School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan. Chemical & Pharmaceutical Bulletin (2004), 52(8), 953-956. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 141:349942 AN 2004:686783 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Antioxidant capacity for a wide range of natural or synthetic polyphenolics was comprehensively evaluated by vitamin C equiv. antioxidant capacity (VCEAC) assay using free blue/green ABTS radicals. The polyphenolics tested are grouped into the following categories: vitamins (β-carotene, α-tocopherol, vitamin A, and vitamin C), phenolic acids (benzoic acid, phenylacetic acid, cinnamic acid, and their derivs.), flavonoids (anthocyanidin, flavanol, chalcone, flavanone, flavone, flavonol, isoflavone, and their derivs.), synthetic food additives (BHA, BHT, TBHQ, and PG), and other misc. polyphenolics (ellagic acid, sesamol, eugenol, thymol, etc.). A pos. linear relationship between VCEAC and the no. of free OH groups around the flavonoid framework was found, whereas, for phenolic acids, the linear relationship was not as good as with the flavonoid aglycons. Groups of chems. having comparable structures generally showed similar trends. Polyphenolics commonly showed a higher VCEAC compared to monophenolics. Compds. like gallic acid with 3 vicinal hydroxy substitutions on the arom. ring in phenolic acids or like epigallocatechin with 3 vicinal hydroxy substitutions on the B ring in flavonoids showed the highest antioxidant capacity among the groups. In the flavonoids, 2 characteristic chem. structures were very important, the catechol moiety in the B ring and the 3-OH functional group in a chroman ring. Glycosylated flavonoids showed less potent antioxidant capacity than their aglycon alone. Synthetic antioxidant food additives (BHA, TBHQ, and BHT) conventionally used in the food industry were less effective antioxidants than ascorbic acid. Other naturally occurring polyphenolics tested followed the expected general trends of phenolic acids and flavonoids.

Abstract

Francis, Inc., CODEN: CRFND6 ISSN: 1040-8398. Journal written in English. CAN 142:446241 AN 2004:690711 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

A review discussing the biotransformation of citrus flavanone glycoside contg. bioresources. Such transformations include enzymic hydrolysis of flavanone glycosides to improve citrus product quality; hydrolysis to produce rhamnose, flavanone glucosides, and flavanones; hydrogenation in basic medium to produce dihydrochalcone sweeteners; and enzymic glycosylation and esterification to

Abstract

Biotransformations of citrus flavanone glycosides. Ellenrieder, Guillermo. National University of Salta - National Research Council (CONICET), Argent. Editor(s): Pandey, Ashok. Concise Encyclopedia of Bioresource Technology (2004), 189-199. Publisher: Haworth Press, Binghamton, N. Y CODEN: 69FTU3 Conference; General Review written in English. CAN 142:296810 AN 2004:673997 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Induction of the migratory phenotype by flavonoids in these models of preneoplastic epithelial cells suggests a novel mechanism for colon cancer prevention.

Colonic epithelial cell migration is required for movement up to the apex of the crypt and, hence, normal differentiated cell function. This migratory phenotype is dependent upon wild-type adenomatous polyposis coli (Apc) expression. The purpose of this study is to det. whether specific flavonoids induce cell migration in colon epithelial cells either wild type or heterozygous for Apc genotype. Nontumorigenic murine colon epithelial cell lines with distinct Apc genotypes, young adult mouse colon (YAMC; Apc+/+) cells, and Immortomouse/Min colon epithelial (IMCE; ApcMin/+) cells were used to assess the ability of specific flavonoids to induce cell migration relative to migration induced by hepatocyte growth factor (HGF). The citrus flavanones naringenin and hesperetin did not induce cell migration comparable with HGF in either cell type. However, the glycosylated forms of these flavanones, naringin and hesperidin, induced migration differentially in YAMC and IMCE cells. Specifically, naringin and hesperidin induced the greatest migratory response in IMCE cells at 1 μM (P < 0.01) and induced migration greater than untreated control cells (P < 0.05) but equal to HGF-treated cells. In YAMC cells, hesperidin did not induce migration except at the 100-μM concn. Apigenin induced migration in IMCE cells at 1 (P < 0.05) and 50 μM (P < 0.01) and did not induce migration in the YAMC cells. Catechin induced migration at the highest concn. (300 μM) only in the IMCE cells, whereas epicatechin induced migration at the lowest concn. only (1 μM) in IMCE cells. Overall, the glycosylated citrus flavanones induced the greatest migratory response at the lowest concn. in IMCE cells. Co-treatment of IMCE cells with the global matrix metalloproteinase (MMP) inhibitor Ilomastat in the presence of naringin, hesperidin, or apigenin demonstrated that flavonoid-induced migration was dependent on MMP activity.

Abstract

Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: Implications of matrix metalloproteinase activity. Fenton, Jenifer I.; Hord, Norman G. Department of Food Science and Human Nutrition, Michigan State University, East Lansing, MI, USA. Nutrition and Cancer (2004), 48(2), 182-188. Publisher: Lawrence Erlbaum Associates, Inc., CODEN: NUCADQ ISSN: 0163-5581. Journal written in English. CAN 142:211519 AN 2004:675950 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


significantly. However, the effects of dihydrogenation of flavones into flavanones on ocular blood flow and retinal function recovery have not been studied and required investigation. Methods: The colored microsphere technique and electroretinog. method were used for the study of ocular blood flow and retinal function, resp. Results: Maximum effects on ocular blood flow were obtained when there were 3 hydroxy groups in the mol. of flavones and flavanones. Dihydrogenation of flavones to flavanones increased the ocular blood flow further. The same is true for retinal function recovery after ischemic insult. Conclusion: These results indicate that hydrogenation is an excellent way to convert natural flavones into more potent compds. of flavanones.


flavanone

High-performance liquid chromatography methods for the analysis of adrenergic amines and flavanones in Citrus aurantium L. var. amara. Pellati, Federica; Benvenuti, Stefania; Melegari, Michele. Department of Pharmaceutical Sciences, University of Modena and Reggio Emilia, Modena, Italy. Phytochemical Analysis (2004), 15(4), 220-225. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal written in English. CAN 141:195020 AN 2004:665481 CAPLUS


The validation of rapid, low-cost spectrophotometric procedures for the quantification of the 3 main groups of bioactive substances (flavones and flavonols, flavanones and dihydroflavonols, and total phenolics) in poplar-type propolis was performed. A spectrophotometric assay based on the formation of an aluminum chloride complex was applied for the quantification of total flavones and flavonols using galangin as std. Because of the high amt. of flavanones and dihydroflavonols in "poplar type" propolis, the introduction of a distinct procedure for their quantification was considered of special significance and the DAB9 colorimetric method was applied for the purpose. Total phenolic content was measured by the Folin-Ciocalteu procedure using a mixt. of pinocembrin and galangin as a ref. The procedures were validated using a model mixt. of compds. representing the poplar-type propolis compn. as found in previous studies. The accuracy (recovery) varied in the range 84-109%, and the relative std. deviation was 0.5-6.2%. The developed spectrophotometric procedures were applied to six poplar type propolis samples. The results were verified independently by a HPLC procedure. The 2 sets of results agreed satisfactory, as proven by Student's t-test.

Abstract

Validated methods for the quantification of biologically active constituents of poplar-type propolis. Popova, Milena; Bankova, Vassya; Butovska, Daniela; Petkov, Valentin; Nikolova-Damyanova, Boryana; Sabatini, Anna Gloria; Marcazzan, Gian Luigi; Bogdanov, Stefan. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulg. Phytochemical Analysis (2004), 15(4), 235-240. Publisher: John Wiley & Sons Ltd., CODEN: PHANEL ISSN: 0958-0344. Journal written in English. CAN 141:248846 AN 2004:665484 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Crystals of the title compd. are orthorhombic, space group Pbca, with a 11.5244(2), b 19.1647(3), c 24.83550(10) .ANG.; Z = 8, dc = 1.23; R = 0.055, Rw(F2) = 0.128 for 4838 reflections. The compd. consists of a pyrazolidine ring, three arom. rings and a flavanone moiety. The pyrazolidine ring is in an envelope conformation and the six membered ring in the flavanone moiety adopts sofa conformation. The structure has a C-H⋅⋅⋅O-type intermol. interaction.

Abstract

2,4,5-Triphenylspiro[pyrazolidine-3,3'-(4'-flavanone)]. Krishna, R.; Raj, S. Shanmuga Sundara; Velmurugan, D.; Fun, Hoong-Kun; Manikandan, S.; Raghunathan, R. Department of Crystallography and Biophysics, University of Madras, Chennai, India. Acta Crystallographica, Section C: Crystal Structure Communications (1999), C55(10), iii, IUC9900120. Publisher: Munksgaard International Publishers Ltd., CODEN: ACSCEE ISSN: 0108-2701. http://journals.iucr.org/c/issues/1999/10/00/issconts.html Journal written in English. CAN 141:197521 AN 2004:669276 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


synthesize new derivs.


flavanone

Fatty acid synthase (FAS) which is a potential antifungal target was employed for bioactivity-guided fractionation of the ethanol ext. of the twigs and leaves of Rheedia acuminata. Three flavanone-(3 8'')-flavone type biflavanoids, morelloflavone, morelloflavone-7-sulfate and volkensiflavone-7-sulfate, one flavanone-(3 8'')-flavanone type biflavanoid, GB-2a-7-sulfate, and the biflavone amentoflavone were isolated. They exhibited IC50 against FAS in a range of 3.5-22 μg/mL, but did not show activity in the cell-based antifungal assays. However, the isolation of these compds. has permitted us to revisit the stereochem. of this biosynthetically important group of natural products. Using spectroscopic methods and computational calcns., the abs. configurations and conformations of the three flavanone-(3 8'')-flavone type biflavanoids were clearly defined. The abs. configuration of the more complex biflavanoid, (+)-GB-2a-7-sulfate, was also deduced by interpretation of its CD data. In addn., the exchangeability of the C-3

Abstract

Absolute configuration and biological activity of biflavonoids from Rheedia acuminata. Li, Xing-Cong; Khan, Shabana I.; Jacob, Melissa; Walker, Larry A.; Ferreira, Daneel. National Center for Natural Products Research, University of Mississippi, University, MS, USA. Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, United States, August 22-26, 2004 (2004), CELL-107. Publisher: American Chemical Society, Washington, D. C CODEN: 69FTZ8 Conference; Meeting Abstract written in English. AN 2004:656076 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Due to their strain-release Lewis acidity, silacyclobutanes (siletanes) show enhanced reactivity in reactions such as the Mukaiyama aldol and aldehyde allylation. In efforts to identify novel applications of these substrates in org. synthesis, we discovered that the C-Si bond of a wide range (aryl, alkenyl, alkyl) of these silacycles can be mildly oxidized under the Tamao reaction protocol in high to excellent yields. Preliminary results and progress in the synthesis of a natural flavanone 2 using this methodol. will be discussed. Also, the design of a novel para-siletanylbenzyl (PSB) 3 protecting group will be mentioned.

Abstract

Silacyclobutane oxidations in organic synthesis. Lam, Hubert T. C.; Dudley, Gregory B. Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL, USA. Abstracts of Papers, 228th ACS National Meeting, Philadelphia, PA, United States, August 22-26, 2004 (2004), ORGN-294. Publisher: American Chemical Society, Washington, D. C CODEN: 69FTZ8 Conference; Meeting Abstract written in English. AN 2004:658559 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Reverse-phase HPLC coupled with photodiode array detection was used for the simultaneous sepn. and detn. of naturally occurring adrenergic amines (octopamine, synephrine and tyramine) in fruits and dry exts. of Citrus aurantium L. var. amara and in herbal medicines derived therefrom. Synephrine was the main component in fruits (0.10-0.35%) and in dry exts. (3.00-3.08%) and was present in the range 0.25-0.99% in herbal medicines. Flavanones were analyzed in the same samples using a reverse-phase HPLC technique which allowed the identification and quantification of neoeriocitrin, narirutin, naringin, hesperidin, neohesperidin, naringenin and hesperetin. C. aurantium fruits and derivs. contained mainly glycosylated flavanones: in particular, naringin and neohesperidin were found to be the major flavonoids and their concns. ranged from 1.80 to 26.30 and from 3.90 to 14.71 mg/g, resp. The levels of aglycons were very low in all samples tested.

Abstract (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Three compds., namely the interesting biflavanonol GB-2 (naringenin I-3, II-8-dihydroquercetin (I)), I-4',I-5,II-5,I-7,II-7-pentahydroxyflavanone(I-3,II-8)chromone [naringenin-(3→8) 5,7-dihydroxychromone (II)] and stigmasterol, were isolated from the leaves of Cratoxylum neriifolium Kurz. I and II show rotameric behavior due to the presence of a single bond between the highly substituted flavanone and flavanonol part and the flavanone and chromone part, resp. Complete NMR spectral assignments of I and II were done at 27 °C and 90 °C for the first time followed by a study of conformational behavior at room temp. by ROESY.

Abstract

Conformational analysis of the biflavanoid GB2 and a polyhydroxylated flavanone-chromone of Cratoxylum neriifolium. Kumar, Vineet; Brecht, Volker; Frahm, August Wilhelm. Department of Pharmaceutical Chemistry, Freiburg, Germany. Planta Medica (2004), 70(7), 646-651. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 142:6322 AN 2004:634609 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


proton of the flavanone moiety of morelloflavone by deuterium in acetone-d6/D2O at ambient temp. with retention of configuration indicates considerable chiral stability of this class of biflavonoids.


flavanone

Answer 753:

Biochem. basis for processing of various pectin-contg. fruits was discussed. The chem. compn. of fruit of cherry plum, nectarine, medlar and prickly pear was analyzed. The data on application of different substances for aromatization of wines and drinks are given. Antioxidant activity of a no. of species of the Crimean flora was investigated. Method of bioelectrog. proved to be useful for estn. of biol. and energy value in plant stuff and products.

Abstract

Biochemical basis for processing of plants for medicinal products. Ezhov, V. N.; Polonskaya, A. K. Nikitskii Bot. Sad Nats. Nauchnyi Tsentr, Ukr. Akad. Agrar. Nauk., Ukraine. Byulleten Glavnogo Botanicheskogo Sada (2003), 186 214-226. Publisher: Nauka, CODEN: BYGBAA ISSN: 0366-502X. Journal written in Russian. CAN 142:225381 AN 2004:619701 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

HO

OH

OH

OH

O

OOH

HO

OH

H

O

O

HO

OH

O

OOH

HO

OH

H

I

II


flavanone

Optimization of chromatographic conditions in thin layer chromatography of flavonoids and phenolic acids. Medic-Saric, Marica; Jasprica, Ivona; Smolcic-Bubalo, Asja; Mornar, Ana. Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb,


The metabolic modifications of birch (Betula pubescens) leaf phenolics in the digestive tract of its major defoliator, larvae of the autumnal moth Epirrita autumnata, were studied. The main phenolic acids of birch, i.e., chlorogenic and p-coumaroylquinic acids, were isomerized in the alk. digestive tract. Moreover, only 16 to 92% of the ingested amts. of chlorogenic acid were found in the feces of individual larvae; the missing portion is possibly being used in the formation of reactive o-quinones. Water-sol. flavonoid glycosides were mostly excreted unaltered. In contrast, lipophilic flavonoid aglycons were not excreted as such, but as glycosides after being detoxified by E. autumnata via glycosylation. When the larvae were fed with leaf-painted acacetin and kaempferide, i.e., two naturally occurring birch leaf flavonoid aglycons, acacetin-7-O-glucoside and kaempferide-3-O-glucoside appeared in larval feces as major metabolites. However, the efficiency of aglycon glycosylation varied, ranging from 17 to 33%, depending on the aglycon and its dietary level. There was also large variation in the efficiency of glycosylation, from 2 to 57%, among individual larvae. These results demonstrate a compd.-specific metab. of phenolic compds., leading to different phenolic profiles in the insect gut compared to its leaf diet.

Abstract

Metabolic modifications of birch leaf phenolics by an herbivorous insect: Detoxification of flavonoid aglycons via glycosylation. Salminen, Juha-Pekka; Lahtinen, Maria; Lempa, Kyoesti; Kapari, Lauri; Haukioja, Erkki; Pihlaja, Kalevi. Laboratory of Environmental Chemistry, Department of Chemistry, University of Turku, Turku, Finland. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2004), 59(5/6), 437-444. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 141:392174 AN 2004:613986 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Monolithic capillary columns contg. native silica gel were modified with cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC) and used for enantiosepns. in capillary liq. chromatog. The method adopted for in situ enantioselective modification of monolithic fused silica capillary columns by coating with CDMPC appears to be fairly simple and fast. High efficiency enantiosepns. of test racemic compds. and several chiral drugs were achieved in a short time. It was possible to increase the amt. of chiral selector present by multiple coating of monoliths with CDMPC. The baseline enantiosepn. of 2,2,2-trifluoro-1-(9-anthryl)ethanol was achieved in an anal. time <30 s with this capillary column. Reproducible enantiosepns. were obtained when the chiral selector was removed from the monolithic column by flushing it with appropriate solvent and the column recoated.

Abstract

High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified with cellulose tris(3,5-dimethylphenylcarbamate). Chankvetadze, Bezhan; Yamamoto, Chiyo; Tanaka, Nobuo; Nakanishi, Kazuki; Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, Georgia. Journal of Separation Science (2004), 27(10-11), 905-911. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 141:374263 AN 2004:616339 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

The inhibition of superoxide anion generation by neutrophils from Viscum articulactum. Leu, Yann-Lii; Kuo, Shih-Ming; Hwang, Tsong-Long; Chiu, Shau-Ting. Graduate Institute of Natural Products, College of Medicine, Chang Gung University, Tao-Yuan, Taiwan. Chemical & Pharmaceutical Bulletin (2004), 52(7), 858-860. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 141:346504 AN 2004:596854 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The major flavanone-7-O-glycoside constituents in citrus fruit juices (naringin, hesperidin, neohesperidin, narirutin, and eriocitrin) were sepd. as diastereomers by multidimensional LC. The method consisted of coupling 2 HPLC columns: a reversed-phase (RP18) column was used for the sepn. of flavanone glycosides, which were, then, individually switched into a carboxymethylated β-cyclodextrin (β-CD)-based column and resolved as the corresponding stereoisomers. The method was used for the full anal. of flavanone glycosides in fresh hand-squeezed and com. fruit juices by combining the quant. estn. with the diastereomeric anal. Quant. data were in general consistent with previously reported data in this field. CC-LC isomer anal. was carried out by coupling the β-CD column with a mass spectrometer operated with neg. ion electrospray ionization (ESI-MS). The results showed that hesperidin was present in orange juices almost exclusively as the 2S isomer, whereas narirutin had mainly the 2R configuration. In grapefruit juices, (2S)-naringin prevailed with the respect to the 2R isomer, whereas the opposite was true for narirutin. Lemon juices contained eriocitrin stereoisomers in equal amt. (50% each), but hesperidin was almost exclusively found as the 2S isomer. Significant differences of the diastereomeric ratios were obsd. between freshly squeezed juices and juices from com. sources.

Abstract

Separation of Flavanone-7-O-glycoside Diastereomers and Analysis in Citrus Juices by Multidimensional Liquid Chromatography Coupled with Mass Spectrometry. Aturki, Zeineb; Brandi, Valentina; Sinibaldi, Massimo. Istituto di Metodologie Chimiche, CNR-Area della Ricerca di Roma, Rome, Italy. Journal of Agricultural and Food Chemistry (2004), 52(17), 5303-5308. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 141:276457 AN 2004:606748 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids are one of the largest groups of natural compds. known. They are supposed to have numerous physiol. activities. There are many foods that contain flavonoids, but one of the most important sources of flavonoids is propolis. Besides flavonoids, phenolic acids are the main active substances of propolis. The list of uses and prepns. of propolis is almost endless and demands an accurate anal. method to define the substances in this natural product. It can be easily analyzed by chromatog. methods, but before testing a new type of propolis it is opportune to optimize chromatog. conditions. The aim of this study is to optimize the chromatog. conditions in TLC of flavonoids and phenolic acids, as std. compds. that may be present in Croatian propolis. The authors compared 9 different mobile phases, using information theory and numerical taxonomy methods and applying the computer search program KT1, to find the most appropriate mobile phase, the optimal combination of 2 and 3 mobile phases for sepn. of stds.

Abstract

Croatia. Croatica Chemica Acta (2004), 77(1-2), 361-366. Publisher: Croatian Chemical Society, CODEN: CCACAA ISSN: 0011-1643. Journal written in English. CAN 141:248845 AN 2004:610896 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Cloning and sequence analysis of flower tissue-specific expression gene promoter PchsA from Petunia hybrida. Hong, Yahui; Jiang, Hong; Xiao, Langtao; Huang, Huang; Zhang, Wen. Department of Biotechnology, HNAU, Changsha, Hunan Province, Peop. Rep. China. Hunan Nongye Daxue Xuebao (2003), 29(6), 474-477. Publisher: Hunan Nongye Daxue Xuebao Bianjibu, CODEN: HNDXFL ISSN: 1007-1032. Journal written in Chinese. CAN 141:289896 AN 2004:567363 CAPLUS (Copyright (C)


Two pterocarpans [(6aR,11aR)-maackiain, (6aR,11aR)-medicarpin], one flavanone [(2S)-7-hydroxy-6-methoxy-flavanone], one isoflavan (sativan) and two isoflavones (pseudobaptigenin, genistein) were isolated from the Spatholobus suberectus (Leguminosae). Their chem. structures were detd. by comparison of their spectroscopic parameters of CD, EIMS, 1D-NMR and 2D-NMR with those reported in the literatures. All of these compds. are reported for the first time from this plant.

Abstract

Flavonoids from Spatholobus suberectus. Yoon, Jeong Seon; Sung, Sang Hyun; Park, Jong Hee; Kim, Young Choong. College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University, Seoul, S. Korea. Archives of Pharmacal Research (2004), 27(6), 589-592. Publisher: Pharmaceutical Society of Korea, CODEN: APHRDQ ISSN: 0253-6269. Journal written in English. CAN 142:71467 AN 2004:591500 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The leaf essential oil of Syzygium Jambos (Linn)⋅Alston (Myrtaceae) was isolated by steam distn. and sepd. by GC. The sepd. components were identified by GC/MS, the main components were α-caryophyllene, β-pinene, linalool, β-ocimene, α-terpineol, γ-terpinen, trans-nerolidol. The pulp essential oil of Syzygium Jambos (Linn)⋅Alston contained nerolidol with high percentage (16.4 %). The chem. compns. of petroleum ether and methanol exts. of the flower of Syzygium Jambos (Linn)⋅Alston were identified by GC/MS. The main components were found to be flavonoids 8-hydroxy-6-methoxy flavanone, 5,7-dihydroxyflavanone, 6,8-dihydroxy-5-methylflavanone, 5-hydroxy, 7-methoxy, 6,8-di-Me flavanone, and 5,7-dimethoxy flavanone. The main components of the petroleum ether ext. of the bark of Syzygium Jambos (Linn)⋅Alston were 9,12-octadecadienoic acid (23.5 %), 9-octadecenoic acid (15.4 %) and n-hexadecanoic acid (13.7 %).

Abstract

Chemical compositions of Syzygium Jambos (Linn)⋅Alston. Hoang, Van Luu; Nguyen, Quang Tue. Dept. Chem., Vinh University, Vietnam. Tap Chi Phan Tich Hoa, Ly Va Sinh Hoc (2004), 9(1), 20-23, 19. Publisher: Vietnam Analytical Sciences Society, CODEN: TCPTAH Journal written in Vietnamese. CAN 141:415578 AN 2004:595171 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new flavanones, (2S)-pinocembrin 7-O-[β-D-apiosyl(1→2)]-β-D-glucoside (1), and (2S)-pinocembrin 7-O-[cinnamoyl(1→5)-β-D-apiosyl(1→2)]-β-D-glucoside (2) together with eighteen known compds., which include five known flavanones, nine benzenoids, one inositol and three triterpenoids, were isolated and characterized from fresh Viscum articulactum. Structures of new compds. were detd. by spectral anal. Among them, oleanolic acid (18) showed a significant inhibition effect on superoxide anion generation by human neutrophils in response to formyl-L-methionyl L-leucyl-L-phenylalanine (fMLP).


flavanone

A new flavanone glycoside, naringenin-4'-O-β-D-glucuronopyranoside was isolated from leaves of Impatiens balsamina together with a known but rare flavanone monoglycoside: naringenin 4'-O-β-D-glucopyranoside, four rare flavonol diglycosides: quercetin 3-O-α-L-rhamnopyranosyl(1→6)-β-D-galactopyranoside, kaempferol-3-O-α-L-rhamnopyranosyl-7-O-α-L-arabinopyranoside, quercetin-3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranoside, quercetin-3-O-α-L-arabinopyranosyl(1→2)-β-D-glucopyranoside and three

Abstract

A new flavanone glycoside from leaves of Impatiens balsamina. Hasan, A.; Tahir, M. N.; Malik, A.; Sharif, C. A.; Khan, M. A. Department of Chemistry, Quaid-i-Azam University, Islamabad, Pak. Journal of the Chemical Society of Pakistan (2004), 26(2), 167-170. Publisher: Chemical Society of Pakistan, CODEN: JCSPDF ISSN: 0253-5106. Journal written in English. CAN 141:310655 AN 2004:563001 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The distribution of seven flavonoids, eriocitrin, luteolin 3'-O-β-D-glucuronide, hesperidin, diosmin, isoscutellarein 7-O-glucoside, hispidulin 7-O-glucoside, and genkwanin, has been studied in Rosmarinus officinalis leaves, flowers, stems, and roots during plant growth. The max. level reached by luteolin 3'-O-β-D-glucuronide in leaves during June-August suggests the existence of a delay between the activation of the enzymes involved in the flavanone and flavone biosynthesis. The presence of hesperidin and diosmin in the vascular system is significant, and hesperidin shows even higher levels than the phenolic diterpenes and rosmarinic acid. The distribution of flavonoids obsd. in R. Officinalis suggests a functional and structural relationship between phytoregulators and flavonoids, where flavonoids would be "protectors" of the activity of phytoregulators. A hypothesis for the general pathway of biosynthesis of these compds. in plants of the family Labiatae is proposed.

Abstract

Flavonoid Distribution during the Development of Leaves, Flowers, Stems, and Roots of Rosmarinus officinalis. Postulation of a Biosynthetic Pathway. Del Bano, Maria Jose; Lorente, Juan; Castillo, Julian; Benavente-Garcia, Obdulio; Marin, Maria Piedad; Del Rio, Jose Antonio; Ortuno, Ana; Ibarra, Isidro. Research and Development Department, Nutrafur-Furfural Espanol S.A., Alcantarilla, Murcia, Spain. Journal of Agricultural and Food Chemistry (2004), 52(16), 4987-4992. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 141:239991 AN 2004:566923 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


According to the sequence of flower tissue-specific expression gene CHSA promoter in Petunia hybrida reported by Ingrid M., we designed and synthesized a pair of primers. With total DNA of Petunia hybrida used as template, we got a DNA fragment about 370 bp amplified by PCR procedure, reclaimed the product and cloned it into plasmid vector pUCm-T. We confirmed the recombinant after transformation and filtration. Then the recombinant T-vectors were identified by restriction enzymes and subjected to sequence anal. The result shows that this fragment's length is 370 bp. We use DSgene analyze software to analyze the sequence and find that it has all the basic conservative sequences of a promoter, TATA box, CCAAT box, anther box, G-box, TACPyAT box, box1, box2, Capsite etc. These sequences are totally the same as what is reported, and the fragment is proved to share 96% homol. with the reported sequence by Internet BLAST program and DSgene analyze software.

Abstract 2008 ACS on SciFinder (R))


flavanone

While the wild-type morning glory (Ipomoea tricolor) displays bright-blue flowers and dark-brown seeds, its spontaneous mutant, Blue Star, carrying the mutable ivory seed-variegated (ivs-v) allele, exhibits pale-blue flowers with a few fine blue spots and ivory seeds with tiny dark-brown spots. The mutable allele is caused by an intragenic tandem duplication of 3.3 kbp within a gene for transcriptional

Abstract

An intragenic tandem duplication in a transcriptional regulatory gene for anthocyanin biosynthesis confers pale-colored flowers and seeds with fine spots in Ipomoea tricolor. Park, Kyeung-Il; Choi, Jeong-Dao; Hoshino, Atsushi; Morita, Yasumasa; Iida, Shigeru. National Institute for Basic Biology, Okazaki, Japan. Plant Journal (2004), 38(5), 840-849. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 141:289738 AN 2004:534817 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The presence of OH groups at certain positions and the double bond at C2-C3 in the flavonoid mols., which produces lipophilic action, can affect the increment on ocular blood flow and retinal function recovery. O-methylation can increase ocular blood flow and retinal function recovery as well.

We have recently reported that the effect of a flavonoid on ocular blood flow depends upon the no. of hydroxy (OH) groups in its backbone structure. To elucidate the structural features on the no. and type of functional groups present in the flavonoid mol. plus the no. of OH groups, flavonoids with four to five OH groups, with or without methoxy groups, were studied on their effects to affect the ocular blood flow and the retinal function recovery. A colored microsphere technique was used to det. the ocular blood flow in albino rabbit eyes and electroretinog. was used to measure the retinal function recovery. Flavonols with four free OH groups produced no effects on the ocular blood flow (fisetin, kaempferol), whereas flavanone and flavones with four free OH groups and without the C2-C3 double bond produced the rapid increment on ocular blood flow (dihydrofisetin and luteolin, resp.). Similarly, flavonols with five free OH groups produced no effects on the ocular blood flow (morin, quercetin). Yet, flavanone with five free OH groups and without the C2-C3 double bond produced the rapid increment on ocular blood flow (dihydroquercetin). Flavanols with five free OH groups and without the C2-C3 double bond and the carbonyl group produced no effects on the ocular blood flow (catechin). Flavonols with four free OH groups and a methoxy group on the 7 position produced no effects on the ocular blood flow (Rhamnetin). Flavonols with four free OH groups and a methoxy group at the 5 (5-methylquercetin) or 3' position (isorhamnetin) produced pos. effects on the ocular blood flow also. Flavonol with five methoxy groups but no OH group produced pos. effects on the ocular blood flow (pentamethylquercetin). Flavonols with an excessive no. of OH groups, having both a catechol-like structure in the C ring and a catechol at the B ring, produced no effect on the ocular blood flow (rhamnetin, quercetin). Parallel results were obtained on retinal function recovery after ischemic insult.

Abstract

Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes. Park, Young-Hyun; Xu, Xin-Rong; Chiou, George C. Y. Institute of Ocular Pharmacology and Department of Medical Pharmacology and Toxicology, Texas A and M University College of Medicine, College Station, TX, USA. Journal of Ocular Pharmacology and Therapeutics (2004), 20(3), 189-200. Publisher: Mary Ann Liebert, Inc., CODEN: JOPTFU ISSN: 1080-7683. Journal written in English. CAN 141:133568 AN 2004:553349 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavonol monoglycosides: kaempferol-7-O-α-L-rhamnopyranoside, kaempferol-7-O-β-D-allopyranoside and quercetin-3-O-β-D-glucopyranoside. Their structures were detd. by means of co-chromatog., UV, EI-MS, FAB-MS and 1HNMR spectroscopy.


flavanone

Answer 767:

Aromatase, a cytochrome P 450 hemoprotein that is responsible for estrogen biosynthesis by conversion of androgens into estrogens, is an attractive target in the treatment of hormone-dependent breast cancer. As a result, a no. of synthetic steroidal or nonsteroidal aromatase inhibitors have been successfully developed. In addn., there are several classes of natural products that exert potent activities in aromatase inhibition, with the flavonoids being most prominent. Previous studies have exploited flavone and flavanone scaffolds for the development of new aromatase inhibitors. In this paper, the design, synthesis, and biol. evaluation of a novel series of 2-(4'-pyridylmethyl)thioisoflavones as the first example of synthetic isoflavone-based aromatase inhibitors is described.

Abstract

Synthesis and Aromatase Inhibitory Activity of Novel Pyridine-Containing Isoflavones. Kim, Young-Woo; Hackett, John C.; Brueggemeier, Robert W. Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH, USA. Journal of Medicinal Chemistry (2004), 47(16), 4032-4040. Publisher: American Chemical Society, CODEN: JMCMAR ISSN: 0022-2623. Journal written in English. CAN 141:225176 AN 2004:528519 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


We succeeded in a first total synthesis of flavocommelin (I), a component of the blue supramol. pigment, commelinin, from Commelina communis, by direct 6-C-glycosylation of the flavan (II) using perbenzylglucosyl fluoride in the presence of MS 5 .ANG. in CH2Cl2 and a catalytic amt. of BF3⋅Et2O. After 6-C-glycosylation of II, oxidn. with CAN to flavanone and subsequent 4'-O-glycosylation, promoted with a combination of BF3⋅Et2O and DTBMP, afforded diglucosylflavanone. DDQ oxidn. of diglucosylflavanone. and deprotection successively gave I.

Abstract

Total Synthesis of Flavocommelin, a Component of the Blue Supramolecular Pigment from Commelina communis, on the Basis of Direct 6-C-Glycosylation of Flavan. Oyama, Kinichi; Kondo, Tadao. Chemical Instrument Center and Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Japan. Journal of Organic Chemistry (2004), 69(16), 5240-5246. Publisher: American Chemical Society, CODEN: JOCEAH ISSN: 0022-3263. Journal written in English. CAN 141:243735 AN 2004:528528 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


activator contg. a basic helix-loop-helix (bHLH) DNA-binding motif. Each of the tandem repeats is flanked by a 3-bp sequence AAT, indicating that the 3-bp microhomol. is used to generate the tandem duplication. The transcripts in the pale-blue flower buds of the mutant contain an internal 583-bp tandem duplication that results in the prodn. of a truncated polypeptide lacking the bHLH domain. The mRNA accumulation of most of the structural genes encoding enzymes for anthocyanin biosynthesis in the flower buds of the mutant was significantly reduced. The transcripts identical to the wild-type mRNAs for the transcriptional activator were present abundantly in blue spots of the variegated flowers, whereas the transcripts contg. the 583-bp tandem duplication were predominant in the pale-blue background of the same flowers. The flower and seed variegations studied here are likely to be caused by somatic homologous recombination between an intragenic tandem duplication in the gene encoding a bHLH transcriptional activator for anthocyanin biosynthesis, whereas various flower variegations are reported to be caused by excision of DNA transposons inserted into pigmentation genes.


flavanone

New prenylated flavones from the roots of Ficus beecheyana. Lee, Ching-kuo; Lu, Chung-kuang; Kuo, Yuen-Hsiung; Chen, Jian-Zhi; Sun, Guang-Zhong. Graduate Institute of Pharmacognosy Science, Taipei Medical University, Taipei, Taiwan. Journal of the Chinese Chemical Society (Taipei, Taiwan) (2004), 51(2), 437-441. Publisher: Chinese Chemical Society, CODEN: JCCTAC


Microarray technol. has given plant biologists the ability to simultaneously monitor changes in the expression of hundreds of genes, and yet, to date, this technol. has not been applied to ecol. phenomena. In native tobacco (Nicotiana attenuata), prior attack of sap-feeding mirids (Tupiocoris notatus) results in vaccination of the plant against subsequent attacks by chewing hornworms (Manduca sexta). This vaccination is mediated by a combination of direct and indirect defenses and tolerance responses, which act in concert with the attack preferences of a generalist predator. Here, we use microarrays enriched in herbivore-elicited genes with a principal components anal. (PCA) to characterize transcriptional 'imprints' of single, sequential, or simultaneous attacks by these two main herbivores of N. attenuata. The PCA identified distinctly different imprints left by individual attack from the two species after 24 h, but not after 5 days. Moreover, imprints of sequential or simultaneous attacks differed significantly from those of single attack, suggesting the existence of a distinct gene expression program responsive to the combination of biol. stressors. A dissection of the transcriptional imprints revealed responses in direct and indirect defense genes that were well correlated with obsd. increases in defense metabolites. Attack from both herbivores elicits a switch from growth- to defense-related transcriptional processes, and herbivore-specific changes occur largely in primary metab. and signaling cascades. PCA of these polygenic transcriptional imprints characterizes the ephemeral changes in the transcriptome that occur during the maturation of ecol. relevant phenotypic responses.

Abstract

Herbivore-induced plant vaccination. Part II. Array-studies reveal the transience of herbivore-specific transcriptional imprints and a distinct imprint from stress combinations. Voelckel, Claudia; Baldwin, Ian T. Max Planck Institute for Chemical Ecology, Jena, Germany. Plant Journal (2004), 38(4), 650-663. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 141:221752 AN 2004:518089 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Covalent immobilization of 3,5-dimethylphenylcarbamate deriv. of cellulose was performed in situ onto native silica monoliths cladded in a 50 mm × 4.6 mm polyether ether ketone HPLC column. The covalent attachment of cellulose deriv. at 16-19% (wt./wt.) was performed via an epoxide moiety. The column obtained by this technique combines the high enantiomer-resolving ability of the polysaccharide deriv. with favorable dynamic properties of monolithic HPLC columns. The covalent attachment of the cellulose deriv. enables this column to be used in combination with the mobile phases which are incompatible with coated-type polysaccharide columns due to soly. of chiral selector in some org. solvents.

Abstract

High-performance liquid chromatographic enantioseparations on monolithic silica columns containing a covalently attached 3,5-dimethylphenylcarbamate derivative of cellulose. Chankvetadze, Bezhan; Ikai, Tomoyuki; Yamamoto, Chiyo; Okamoto, Yoshio. Molecular Recognition and Separation Science Laboratory, School of Chemistry, Tbilisi State University, Tbilisi, Georgia. Journal of Chromatography, A (2004), 1042(1-2), 55-60. Publisher: Elsevier Science B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 141:199170 AN 2004:522450 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Abstract

Chemical components of Anaphalis sinica Hance. Hua, Yan; Wang, Han-Qing. State Key Laboratory of OSSO, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Peop. Rep. China. Journal of the Chinese Chemical Society (Taipei, Taiwan) (2004), 51(2), 409-415. Publisher: Chinese Chemical Society, CODEN: JCCTAC ISSN: 0009-4536. Journal written in English. CAN 141:257384 AN 2004:514899 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

OH

OH

OH

O

MeMe

Me

Me

O

O

OH

OH

OH

OMeMe

MeMe

I

II

Two new prenylated flavanones, ficubee A (I) and ficubee B (II), resp., as 7,8-(2,2-dimethylpyrano)-6-prenyl-5,3',4'-trihydroxyflavone and 6,7-(2,2-dimethylpyrano)-8-prenyl-5,3',4'-trihydroxyflavone were isolated from the roots of Ficus beecheyana together with twelve known compds.: β-sitosterol, 5-stigmasten-3β,7α-diol, 5-stigmasten-3β,7β-diol, 3β-hydroxystigmast-5-en-7-one, 4-hydroxybenzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, 1-(4-hydroxyphenyl)-ethanone, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxycinnamic acid, seseline, xanthyletin, and psoralene. The structures of these secondary metabolites were detd. by spectroscopic means and in comparison with published data.

Abstract

ISSN: 0009-4536. Journal written in English. CAN 141:257387 AN 2004:514903 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Enzymic acylation of flavonoids. Moussou, Philippe; Falcimaigne, Aude; Pauly, Gilles; Ghoul, Mohamed; Engasser, Jean-Marc; Ardhaoui, Melika. (Cognis France S.A., Fr.). Eur. Pat. Appl. (2004), 11 pp. CODEN: EPXXDW EP 1426445 A1 20040609 Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, SK. Patent written in German. Application: EP 2002-292969 20021203. Priority: . CAN 141:5893 AN 2004:470353


RNase P, a ribonucleoprotein responsible for the 5' maturation of precursor tRNAs (ptRNAs) in all organisms, can be enticed to cleave any target mRNA that forms a ptRNA-like structure and sequence-specific complex when bound to an RNA, termed the EGS (external guide sequence). In the present study, F3H (flavanone 3-hydroxylase), a key enzyme in the flavonoid biosynthetic pathway that participates in the formation of red-colored anthocyanins, was used as a target for RNase P-mediated gene disruption in maize cells. Transient expression of an EGS complementary to the F3H mRNA resulted in suppression of F3H to 29% of the control, as indicated by a reduced no. of anthocyanin-accumulating cells. This decrease was not obsd. in expts. where a disabled mutant EGS was expressed. Our results demonstrate the potential of employing plant RNase P, in the presence of an appropriate gene-specific EGS, as a tool for targeted degrdn. of mRNAs.

Abstract

RNase P as a tool for disruption of gene expression in maize cells. Rangarajan, Sunita; Raj, M. L. Stephen; Hernandez, J. Marcela; Grotewold, Erich; Gopalan, Venkat. Department of Biochemistry, The Ohio State University, Columbus, OH, USA. Biochemical Journal (2004), 380(3), 611-616. Publisher: Portland Press Ltd., CODEN: BIJOAK ISSN: 0264-6021. Journal written in English. CAN 141:118794 AN 2004:502282 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

HO

OH

CH 2

O

O

OHMe

Et

Me Me

I

Twenty components (including a new flavanone) were isolated and identified from the whole plant of Anaphalis sinica Hance. Their structures were detd. on the basis of spectral anal. and chem. transformation. These components are 6-[(5-methyl-6-ethyl-4-hydroxy-pyrone-3-yl)-methylene]glabranine (I), kaempferol, tiliroside, quercetin, quercetin-3-O-β-D-glucoside, scutellarin , 5,7-dihydroxy-8-methoxyflavone, 5,7-dihydroxy-4'-methoxy-flavone-7-O-α-L-rhamnopyranosyl(1→6)-β-D-glucopyranoside, helipyrone , 4'-hydroxydehydrokawain, panamin (II), ursolic acid, pomolic acid, 3-acetyloleanolic acid, a mixt. of N-(2-hydroxy-acyl)-4-hydroxy-8(E)-ene-sphingenine, O-methyl-D-inositol, a mixt. of β-sitosterol and stigmasterol and a mixt. of daucosterol and stigmasterol-β-D-glucoside. Among them, I is a new compd., and 13CNMR data of II is reported for the first time.


flavanone

The reaction of 2'-hydroxyacetophenone with benzaldehyde was studied over H-ZSM-5, Mg-ZSM-5 and Ba-ZSM-5 catalysts at 140°. The products were 2'-hydroxychalcone and flavanone. The conversion of 2'-hydroxyacetophenone increased with time and attained a max. of 40-50% conversion over all the catalysts. Though the yield of chalcone and flavanone increased with increase in time, the yield of flavanone was less than 2'-hydroxychalcone over all the catalysts. The order of activity of the catalysts was Mg-ZSM-5 > Ba-ZSM-5 > H-ZSM-5. The influence of temp. in the range of 100-160° on conversion and products yield was studied over Mg-ZSM-5.

Abstract

Liquid phase reaction of 2'-hydroxyacetophenone and benzaldehyde over ZSM-5 catalysts. Saravanamurugan, S.; Palanichamy, M.; Arabindoo, Banumathi; Murugesan, V. Department of Chemistry, Anna University, Chennai, India. Journal of Molecular Catalysis A: Chemical (2004), 218(1), 101-106. Publisher: Elsevier Science B.V., CODEN: JMCCF2 ISSN: 1381-1169. Journal written in English. CAN 141:395381 AN 2004:465828 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A process is provided for the enzymic acylation of glycosylated flavonoids. Thus, rutin was acylated with palmitic acid by the immobilized lipase Novozyme 435 in a tert-amyl alc. solvent system. The reaction was conducted at 60 °C under vacuum (150 mbar). Water was removed from the gas phase by a mol. sieve. After 48 h reaction time, 90% of the substrates were consumed. The enzyme was removed by filtration, and unreacted substrates were removed by solvent extn.


R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, FI, RO, CY, TR, BG, CZ, EE, HU, SK

EP 1567655 A2 20050831 EP 2003-812154 20031122

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI, SK, TR

W: JP, KR, USWO 2004050889 A3 20040812WO 2004050889 A2 20040617 WO 2003-EP13143 20031122

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR, BG, CZ, EE, SK

EP 1426445 A1 20040609 EP 2002-292969 20021203Patent No. Kind Date Application No. Date Patent Family Information CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 776:

There is increasing evidence to suggest that toxic oxygen radicals play a role in the pathogenesis of ischemia/reperfusion (I/R) injury in the kidney. This study was designed to investigate the effects of naringin (Ng), a bioflavonoid in I/R induced renal failure in rats. The protective effect of naringin against the damage inflicted by reactive oxygen species (ROS) during renal I/R was investigated in Sprague-Dawley rats using histopathol. and biochem. parameters. In one set of expts. animals were unilaterally nephrectomized, and subjected to 45 min of left renal pedicle occlusion and in another set both the renal pedicles were occluded for 45 min followed by 24 h of reperfusion. Naringin (400 mg kg-1, p.o.) was administered 60 min prior to ischemia. At the end of the reperfusion period, rats were sacrificed. Thiobarbituric acid reactive substances (TBARS), reduced glutathione (GSH) levels, catalase (CAT), and superoxide dismutase (SOD) activities were detd. in renal tissue. Serum creatinine and blood urea nitrogen (BUN) concns. were measured for the evaluation of renal function. Ischemic control animals demonstrated severe deterioration of renal function, renal morphol. and a significant renal oxidative stress. Pretreatment of animals with naringin markedly attenuated renal dysfunction, morphol. alterations, reduced elevated TBARS levels and restored the depleted renal antioxidant enzymes. The findings imply that ROS play a causal role in I/R induced renal injury and naringin exert renoprotective effects probably by the radical scavenging and antioxidant activities.

Abstract

The effect of naringin, a bioflavonoid on ischemia-reperfusion induced renal injury in rats. Singh, Devinder; Chopra, Kanwaljit. University Institute of Pharmaceutical Sciences, Pharmacology Division, Panjab University, Chandigarh, India. Pharmacological Research (2004), 50(2), 187-193. Publisher: Elsevier, CODEN: PHMREP ISSN: 1043-6618. Journal written in English. CAN 141:405859 AN 2004:463795 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The human fecal anaerobe, E. ramulus, is capable of degrading various flavonoids, including the flavone, naringenin. The 1st step in the proposed degrdn. pathway is the isomerization of naringenin to the corresponding chalcone. Here, cell-free exts. of E. ramulus were found to exhibit chalcone isomerase (I) activity. I from E. ramulus was purified to homogeneity. Its apparent mol. wt. was estd. to be 136 and 129 kDa according to gel filtration and native PAGE, resp. I was composed of a single type of subunit of 30 kDa mol. wt. Purified I catalyzed the isomerization of naringenin chalcone, isoliquiritigenin, and butein, 3 chalcones that differ in their hydroxylation pattern. N-bromosuccinimide, but also naringenin and phloretin, inhibited purified I considerably. This is the 1st report of a bacterial I. The physiol. function of the purified enzyme was unclear, but an involvement in the conversion of the flavanone, naringenin, to the chalcone was proposed. The N-terminal amino acid sequence (15 residues) of I was detd. and showed no identity with known protein sequences in databases.

Abstract

First bacterial chalcone isomerase isolated from Eubacterium ramulus. Herles, Claudia; Braune, Annett; Blaut, Michael. Abteilung Gastrointestinale Mikrobiologie, Deutsches Institut fuer Ernaehrungsforschung Potsdam-Rehbruecke, Nuthetal, Germany. Archives of Microbiology (2004), 181(6), 428-434. Publisher: : Springer-Verlag, CODEN: AMICCW ISSN: 0302-8933. Journal written in English. CAN 141:345449 AN 2004:464149 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The increase in conversion was small between 100 and 120°, but above 120 °C there was a marked increase in conversion. The optimal catalyst loading was found to be 0.75 g for 10 mmol reactants. Study of influence of time on Mg-ZSM-5 at 160° revealed a rapid increase in conversion and products yield up to 3 h and a steady state afterwards. The role of solvent in this reaction was studied with DMSO, nitrobenzene and a mixt. of DMSO and nitrobenzene. High conversion was obsd. with DMSO.


flavanone

Microwave-induced, solvent-free transformations of benzoheteracyclanones by HTIB (Koser's reagent). Patonay, Tamas; Levai, Albert; Riman, Eva; Varma, Rajender S. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. ARKIVOC (Gainesville, FL, United States) (2004), (7), 183-195. Publisher: Arkat USA Inc., CODEN: AGFUAR http://www.arkat-usa.org/ark/journal/2004/Antus/SA-1044B/1044B.pdf Journal; Online Computer File written in English. CAN 141:79219 AN 2004:457592 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


N

O

Me

H

O

O

OOH

NMe

O

Me

Me

O

OOH

NMe

O

Me

Me

NMe

O

Me

Me

O

e

e

M

M

I

III

II

⋅

⋅

⋅

⋅

Paramagnetic and diamagnetic flavone and flavanone derivs. modified on the C or B rings were synthesized by condensation, Sonogashira reaction, lithiation, and the Baker-Venkataraman procedure. Thus, reacting aldehyde I with Ag2O/NaOH/THF gave the acid, which was condensed with 2,6-dihydroxyacetophenone to give (pyrrolidinylphenyl)chromene II and the biradical III.

Abstract

Synthesis of paramagnetic and diamagnetic flavones and flavanones. Kalai, Tamas; Kulcsar, Gyozo; Osz, Erzsebet; Jeko, Jozsef; Suemegi, Balazs; Hideg, Kalman. Institute of Organic and Medicinal Chemistry, University of Pecs, Pecs, Hung. ARKIVOC (Gainesville, FL, United States) (2004), (7), 266-276. Publisher: Arkat USA Inc., CODEN: AGFUAR http://www.arkat-usa.org/ark/journal/2004/Antus/SA-1108B/1108B.pdf Journal; Online Computer File written in English. CAN 141:54093 AN 2004:458973 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Flavonoids exist extensively in plants and Chinese herbs, and several biol. effects of flavonoids have been demonstrated. The antitumor effects in colorectal carcinoma cells (HT29, COLO205, and COLO320HSR) of eight flavanones including flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone, 7-OH flavanone, naringenin, naringin, and taxifolin were investigated. Results of the MTT assay indicate that 2'-OH flavanone showed the most potent cytotoxic effect on these three cells, and cell death induced by 2'-OH flavanone was via the occurrence of DNA ladders, apoptotic bodies, and hypodiploid cells, all characteristics of apoptosis. Induction of caspase 3 protein processing and enzyme activity assocd. with cleavage of poly(ADP-ribose) polymerase (PARP) was identified in 2'-OH flavanone-treated cells, and a peptidyl inhibitor (Ac-DEVD-FMK) of caspase 3 attenuated the cytotoxicity of 2'-OH flavanone in COLO205 and HT-29 cells. Elevation of p21 (but not p53) and a decrease in Mcl-1 protein were found in 2'-OH flavanone-treated COLO205 and HT-29 cells. Elevation of intracellular reactive oxygen species (ROS) was detected in 2'-OH flavanone-treated cells by the 2',7'-dichlorodihydrofluorescein diacetate (DCHF-DA) assay, and ROS scavengers including 4,5-dihydro-1,3-benzene disulfonic acid (tiron), catalase, superoxide dismutase (SOD), and pyrrolidine dithiocarbamate (PDTC) suppressed the 2'-OH flavanone-induced cytotoxic effect. S.c. injection of COLO205 induced tumor formation in nude mice, and

Abstract

Structurally related antitumor effects of flavanones in vitro and in vivo: involvement of caspase 3 activation, p21 gene expression, and reactive oxygen species production. Shen, Shing-Chuan; Ko, Ching Huai; Tseng, Shi-Wen; Tsai, Shu-Huei; Chen, Yen-Chou. School of Medicine, Department of Dermatology, Taipei Medical University, Taipei, Taiwan. Toxicology and Applied Pharmacology (2004), 197(2), 84-95. Publisher: Elsevier Science, CODEN: TXAPA9 ISSN: 0041-008X. Journal written in English. CAN 141:116667 AN 2004:422083 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Four lavandulyl flavanones, (2S)-2'-methoxykurarinone (1), sophoraflavanone G (2), leachianone A (3), and (-)-kurarinone (4), which are isolated from the roots of Sophora flavescens were tested for in vitro antimalarial activity against Plasmodium falciparum. Compds. 1-3 showed moderate antimalarial activities with EC50 values of 2.4×10-6, 2.6×10-6, and 2.1×10-6M, resp. These compds. did not show selective toxicity against P. falciparum in the toxicity test on mouse mammalian tumor cells, however, it is suggested that the position of methoxyl groups in flavanone skeleton plays an important role on antimalarial activity.

Abstract

Antimalarial activity of lavandulyl flavanones isolated from the roots of Sophora flavescens. Kim, Youn Chul; Kim, Hye-Sook; Wataya, Yusuke; Sohn, Dong Hwan; Kang, Tai Hyun; Kim, Myung Soo; Kim, Yong Man; Lee, Geon-Mok; Chang, Jong-Duk; Park, Hyun. College of Pharmacy, Wonkwang University, Iksan, S. Korea. Biological & Pharmaceutical Bulletin (2004), 27(5), 748-750. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 141:85431 AN 2004:448716 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The microwave-activated reactions of [hydroxy(tosyloxy)iodo]benzene (HTIB) with various chromanones, thiochromanones and dihydroquinolones under solvent-free conditions have been studied. In addn. to the common dehydrogenation reaction, 2,3-migration also has been obsd. in the case of flavanone and 2,2-disubstituted chromanones. 3-Tosyloxychromanones were isolated from the reaction of chromanone and 2-methylchromanone for the first time. Substrates with nucleophilic heteroatoms such as thiochromanones and 2-phenyl-2,3-dihydro-4-quinolone reacted by electrophilic attack of the heteroatom.

Abstract


flavanone

Answer 782:

Certain phenols possessing at least one unsubstituted ortho position have been found to undergo rapid, regioselective ortho nitration with CAN (cerium (IV) ammonium nitrate) in the presence of NaHCO3 at room temp. to yield o-nitrophenols in high yields. Substituents tolerating these nitration conditions ranged from the activating methoxy and Me groups to the moderately deactivating Cl, Br, CHO and CO2Me groups. In contrast, phenols that contained a strongly deactivating group such as nitro or cyano or 2,6-disubstituted phenols were not nitrated by the CAN/NaHCO3 reagent. More complex nitrophenols such as 6-hydroxy-5-nitro-1,3-benzoxathiol-2-one, 7-hydroxy-6-nitro-3,4,8-trimethylcoumarin, 6-hydroxy-5-flavanone, 1-(4-hydroxy-3-nitrophenyl)-1H-tetrazole-5-thiol, 2-(2-hydroxy-3-nitrophenyl)benzoxazole were also prepd. in good yields by the CAN/NaHCO3 reagent.

Abstract

Facile, high-yield, regioselective synthesis of ortho-nitrophenols using cerium (IV) ammonium nitrate. Sathunuru, Ramadas; Rao, U. Narasimha; Biehl, Ed. Chem. Dep., Southern Methodist Univ., Dallas, TX, USA. ARKIVOC (Gainesville, FL, United States) (2003), (15), 124-133. Publisher: Arkat USA Inc., CODEN: AGFUAR http://arkat-usa.org/ark/journal/2003/General_Part(xv)/03-918D/918D.pdf Journal; Online Computer File written in English. CAN 141:71310 AN 2004:395133 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Yellow flavonols represent important plant pigments in Asteraceae. In contrast to common flavonols, they show addnl. hydroxyl groups in position 6 and/or 8 of the arom. A-ring in addn. to the basic 5,7-hydroxylation pattern. A novel flavonol 6-hydroxylase (F6H) introducing a hydroxyl group in position 6 of quercetin was demonstrated in enzyme prepns. from petals of Tagetes patula and Tagetes erecta. The enzyme was classified as cytochrome P 450 dependent monooxygenase by photoreversible carbon monoxide inhibition, inhibition by NADPH-cytochrome P 450 reductase specific antibodies and cytochrome P 450 specific inhibitors. The flavone luteolin was barely accepted as a substrate. Methylated flavonols, quercetin 7-O-glucoside, flavanones, and dihydroflavonols were not accepted as substrates. The presence of the enzyme was demonstrated in various varieties showing different coloration.

Abstract

The A-ring specific hydroxylation of flavonols in position 6 in Tagetes sp. is catalyzed by a cytochrome P450 dependent monooxygenase. Halbwirth, Heidrun; Forkmann, Gert; Stich, Karl. Institute for Technical BioScience, Technical University of Vienna, Vienna, Austria. Plant Science (Amsterdam, Netherlands) (2004), 167(1), 129-135. Publisher: Elsevier, CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 141:203321 AN 2004:404607 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Primary tumor cells (COLO205-X) derived from a tumor specimen elicited by COLO205 were established, and 2'-OH flavanone showed an significant apoptotic effect in COLO205-X cells in accordance with the appearance of DNA ladders, caspase 3 protein processing, PARP protein cleavage, and increasing p21 protein. These results revealed in vitro, ex vivo, and in vivo antitumor activities of 2'-OH flavanone via apoptosis induction, and indicates that 2'-OH flavanone is an active compd. worthy of development for cancer chemotherapy.

2'-OH flavanone showed a significant inhibitory effect on tumor formation. The appearance of apoptotic cells with H&E staining, and an increase in p21, but not p53, protein by immunohistochem. were obsd. in tumor tissues under 2'-OH flavanone treatment.


flavanone

Quantitative determination of astilbin in rabbit plasma by liquid chromatography. Guo, Jianming; Xu, Qiang; Chen, Ting. School of Life Sciences, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, Peop. Rep. China. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2004), 805(2), 357-360. Publisher:


Estrogen receptor α (ERα) mediates 17β-estradiol (E2) actions through the transcription of E2-sensitive target genes. In addn., rapid non-genomic signaling (e.g., MAPK/ERK) occurs. It is now well accepted that these rapid membrane-initiated responses account for E2-related cancer. Beside many beneficial effects on human health, nutritional flavonoids exert protective and anticarcinogenic effects on E2-related cancer. The mechanism underlying these effects seems to be related to flavonoids antioxidant properties and/or to their ability to alter signal transduction protein kinases. In addn., an antiestrogenic activity has been proposed but not yet defined. However, the identification and characterization of the responsible mechanisms for flavonoid antitumoral effects is poorly understood. Here, we investigated the possibility that the antimitogenic effects of flavonoids are transduced by modulating ERα-mediated rapid signaling. The ability of two flavonoids, the flavanone naringenin and the flavanol quercetin, with respect of E2, to induce ERα activities has been studied in the human cervix epitheloid carcinoma cell line (HeLa) devoid of any estrogen receptors and rendered E2-sensitive by transient transfection with a human ERα expression vector. Our results indicate that flavonoids act as E2 mimetic on ERα transcriptional activity, whereas they impair the activation of rapid signaling pathways committed to E2-induced proliferation. The resulting decoupling of ERα signal transduction could be proposed as a new mechanism in the protective effects of flavonoids against E2-related cancer.

Abstract

Nutritional Flavonoids Modulate Estrogen Receptor α Signaling. Virgili, Fabio; Acconcia, Filippo; Ambra, Roberto; Rinna, Alessandra; Totta, Pierangela; Marino, Maria. Department of Biology, University 'Roma Tree', Rome, Italy. IUBMB Life (2004), 56(3), 145-151. Publisher: Taylor & Francis Ltd., CODEN: IULIF8 ISSN: 1521-6543. Journal written in English. CAN 140:399573 AN 2004:384299 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asym. oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic α-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of (R,R)-Mn(III) salen catalyst induced an S abs. configuration at the position α in the whole series.

Abstract

Synthesis of Racemic and Enantiomerically Enriched α-Oxyfunctionalized Benzocyclanones and Chromanones by Dimethyldioxirane and Dimethyldioxirane/Mn(III) salen System. Patonay, Tamas; Jekoe, Jozsef; Kiss-Szikszai, Attila; Levai, Albert. Department of Organic Chemistry, University of Debrecen, Debrecen, Hung. Monatshefte fuer Chemie (2004), 135(6), 743-756. Publisher: Springer-Verlag Wien, CODEN: MOCMB7 ISSN: 0026-9247. Journal written in English. CAN 141:332012 AN 2004:392983 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 787:

Choline hydroxide was used as a basic catalyst for aldol condensation reactions to produce new C-C bonds between several ketones and aldehydes. Choline supported on MgO exhibited higher TOF values than other well known basic catalysts in these reactions.

Abstract

Supported choline hydroxide (ionic liquid) as heterogeneous catalyst for aldol condensation reactions. Abello, Sonia; Medina, Francisco; Rodriguez, Xavier; Cesteros, Yolanda; Salagre, Pilar; Sueiras, Jesus E.; Tichit, Didier; Coq, Bernard. Dept. de Quimica i Enginyeria Quimica, Universitat Rovira i Virgili, Tarragona, Spain. Chemical Communications (Cambridge, United Kingdom) (2004), (9), 1096-1097. Publisher: Royal Society of Chemistry, CODEN: CHCOFS ISSN: 1359-7345. Journal written in English. CAN 141:88895 AN 2004:347796 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A polyketide synthase has been suggested to play an important role in cannabinoid biosynthesis in Cannabis sativa L. This enzyme catalyzes the biosynthesis of olivetolic acid, one of the precursors for cannabinoid biosynthesis. Using a reverse transcriptase-polymerase chain reaction (RT-PCR) based on the DNA homol. of chalcone synthase (EC 2.3.1.156) and valerophenone synthase (EC 2.3.1.156) of hop (Humulus lupulus), a cDNA encoding a polyketide synthase in C. sativa was identified. The coding region of the gene is 1170 bp long encoding a 389 amino acid protein of a predicted 42.7 kDa mol. mass and with a pI of 6.04. The gene shares a high homol. with a chalcone synthase gene of H. lupulus, 85% and 94% homol. on the level of DNA and protein, resp. Over-expression of the construct in Escherichia coli M15 resulted in a 45 kDa protein. The protein has chalcone synthase activity as well as valerophenone synthase activity, a chalcone synthase-like activity. Using n-hexanoyl-CoA and malonyl-CoA as substrates did not give olivetol or olivetolic acid as a product.

Abstract

Cloning and over-expression of a cDNA encoding a polyketide synthase from Cannabis sativa. Raharjo, Tri J.; Chang, Wen-Te; Verberne, Marianne C.; Peltenburg-Looman, Anja M. G.; Linthorst, Huub J. M.; Verpoorte, Robert. Department of Chemistry, Gadjah Mada University, Yogyakarta, Indonesia. Plant Physiology and Biochemistry (Amsterdam, Netherlands) (2004), 42(4), 291-297. Publisher: Elsevier, CODEN: PPBIEX ISSN: 0981-9428. Journal written in English. CAN 141:49452 AN 2004:363040 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A simple method for detg. the concn. of astilbin, a flavanone, in rabbit plasma was developed. After liq.-liq. extn., the flavanone was detected by HPLC on a 4.6-μm octadecyl-silica column (Nova-Pak C-18) at 291 nm. Linear calibration graphs for astilbin were constructed from 0.44 to 22.17 μM. The limit of quantitation was 0.44 μM in plasma. The method was applied to pharmacokinetic studies after a single i.v. and an oral administration of the compd. to rabbits.

Abstract

Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal written in English. CAN 140:399239 AN 2004:381715 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 789:

Certain flavonoids inhibit glucose uptake in cultured cells. In this report, we show that the grapefruit flavanone naringenin inhibited insulin-stimulated glucose uptake in proliferating and growth-arrested MCF-7 breast cancer cells. Our findings indicate that naringenin inhibits the activity of phosphoinositide 3-kinase (PI3K), a key regulator of insulin-induced GLUT4 translocation, as shown by impaired phosphorylation of the downstream signaling mol. Akt. Naringenin also inhibited the phosphorylation of p44/p42 mitogen-activated protein kinase (MAPK). Inhibition of the MAPK pathway with PD98059, a MAPK kinase inhibitor, reduced insulin-stimulated glucose uptake by approx. 60%. The MAPK pathway therefore appears to contribute significantly to insulin-stimulated glucose uptake in breast cancer cells. Importantly, decreasing the availability of glucose by lowering the glucose concn. of the culture medium inhibited proliferation, as did treatment with naringenin. Collectively, our findings suggest that naringenin inhibits the proliferation of MCF-7 cells via impaired glucose uptake. Because a physiol. attainable dose of 10 μM naringenin reduced insulin-stimulated glucose uptake by nearly 25% and also reduced cell proliferation, naringenin may possess therapeutic potential as an anti-proliferative agent.

Abstract

Naringenin Inhibits Glucose Uptake in MCF-7 Breast Cancer Cells: A Mechanism for Impaired Cellular Proliferation. Harmon, Anne W.; Patel, Yashomati M. Department of Nutrition, University of North Carolina School of Public Health, Chapel Hill, NC, USA. Breast Cancer Research and Treatment (2004), 85(2), 103-110. Publisher: Kluwer Academic Publishers, CODEN: BCTRD6 ISSN: 0167-6806. Journal written in English. CAN 141:405701 AN 2004:343882 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

HO OH

OH

Me O I

The crude methanolic ext. of Zuccagnia punctata was active toward the fungal pathogens of soybean Phomopsis longicolla and Colletotrichum truncatum. Assay-guided fractionation led to the isolation of two chalcones, one flavanone, and a new caffeoyl ester deriv. (I) as the compds. responsible for the antifungal activity. Another new caffeoyl ester deriv. was isolated from the antifungal chloroform ext. but proved to be inactive against the soybean-infecting fungi up to 50 μg/mL.

Abstract

Antifungal chalcones and new caffeic acid esters from Zuccagnia punctata acting against soybean infecting fungi. Svetaz, Laura; Tapia, Alejandro; Lopez, Silvia N.; Furlan, Ricardo L. E.; Petenatti, Elisa; Pioli, Rosanna; Schmeda-Hirschmann, Guillermo; Zacchino, Susana A. Pharmacognosy School of Biochemical and Pharmaceutical Sciences, National University of Rosario, Rosario, Argent. Journal of Agricultural and Food Chemistry (2004), 52(11), 3297-3300. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 141:50610 AN 2004:344645 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Flavonoids are important plant-specific secondary metabolites synthesized from 4-coumaroyl CoA, derived from the general phenylpropanoid pathway, and three malonyl-CoAs. The synthesis involves a plant type III polyketide synthase, chalcone synthase. We report the cloning and coexpression in Escherichia coli of phenylalanine ammonia lyase, cinnamate-4-hydroxylase, 4-coumarate:CoA ligase, and chalcone synthase from the model plant Arabidopsis thaliana. Simultaneous expression of all four genes resulted in a blockage after the first enzymic step caused by the presence of nonfunctional cinnamate-4-hydroxylase. To overcome this problem we fed exogenous 4-coumaric acid to induced cultures. We obsd. high-level prodn. of the flavanone naringenin as a result. We were also able to produce phloretin by feeding cultures with 3-(4-hydroxyphenyl)propionic acid. Feeding with ferulic or

Abstract

Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli. Watts, Kevin T.; Lee, Pyung Cheon; Schmidt-Dannert, Claudia. Department of Biochemistry, Molecular Biology and Biophysics, University of Minnesota, St. Paul, MN, USA. ChemBioChem (2004), 5(4), 500-507. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: CBCHFX ISSN: 1439-4227. Journal written in English. CAN 141:70297 AN 2004:327565 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


substrate naringenin, and in some cases much higher than with eriodictyol. Methylation in the A-ring, however, strongly reduced or abolished the activities with all four enzymes. The results suggested that B-ring 3' methylation is no hindrance for flavonoid dioxygenases. These results characterized a new type of flavonoid O-methyltransferase, and also provided new insights into the catalytic capacities of key dioxygenases in flavonoid biosynthesis.

Catharanthus roseus (Madagascar periwinkle) flavonoids have a simple methylation pattern. Characteristic are B-ring 5' and 3' methylations and a methylation in the position 7 of the A-ring. The first two can be explained by a previously identified unusual O-methyltransferase (CrOMT2) that performs two sequential methylations. We used a homol. based RT-PCR strategy to search for cDNAs encoding the enzyme for the A-ring 7 position. Full-length cDNAs for three proteins were characterized (CrOMT5, CrOMT6, CrOMT7). The deduced polypeptides shared 59-66% identity among each other, with CrOMT2, and with CrOMT4 (a previously characterized protein of unknown function). The five proteins formed a cluster sep. from all other OMTs in a relationship tree. Anal. of the genes showed that all C. roseus OMTs had a single intron in a conserved position, and a survey of OMT genes in other plants revealed that this intron was highly conserved in evolution. The three cDNAs were cloned for expression of His-tagged recombinant proteins. CrOMT5 was insol., but CrOMT6 and CrOMT7 could be purified by affinity chromatog. CrOMT7 was inactive with all compds. tested. The only substrates found for CrOMT6 were 3'-O-methyl-eriodictyol (homoeriodictyol) and the corresponding flavones and flavonols. The mass spectrometric anal. showed that the enzyme was not the expected 7OMT, but a B-ring 4'OMT. OMTs with this specificity had not been described before, and 3',4'-dimethylated flavonoids had not been found so far in C. roseus, but they are well-known from other plants. The identification of this enzyme activity raised the question whether methylation could be a part of the mechanisms channeling flavonoid biosynthesis. We investigated four purified recombinant 2-oxoglutarate-dependent flavonoid dioxygenases: flavanone 3β-hydroxylase, flavone synthase, flavonol synthase, and anthocyanidin synthase. 3'-O-Methyl-eriodictyol was a substrate for all four enzymes. The activities were only slightly lower than with the std.

Abstract

Flavonoid methylation: a novel 4'-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Schroeder, Gudrun; Wehinger, Elke; Lukacin, Richard; Wellmann, Frank; Seefelder, Wallburga; Schwab, Wilfried; Schroeder, Joachim. Institut fuer Biologie II, Universitaet Freiburg, Freiburg, Germany. Phytochemistry (Elsevier) (2004), 65(8), 1085-1094. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 141:102019 AN 2004:341268 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 793:

Spectrometric analyses of flavonoids in twenty propolis samples, collected from ten different geog. localities in northern Croatia using two complementary methods, are reported. Flavones and flavonols were detd. using aluminum chloride and expressed as quercetin equiv. while flavanones were detd. using 2,4-dinitrophenylhydrazine and expressed as naringenin. Contents of flavones and flavonols were similar for most samples and ranged from 2 to 2.3%, except for one sample with a concn. of 1.3% and one sample in which it was not possible to detect flavones and flavonols. The content of flavanones in propolis samples is very variable. 55% Of samples contained flavanones between 15 and 24% and 45% of samples between 4 and 14%. Total levels of flavonoids in raw propolis samples ranged between 5 and 26%; for the majority of samples (75%), the total level of flavonoids ranged between 15 and 25.9%. The high variability of flavanone concn. will affect the biol. activity of propolis prepns.

Abstract

Quantitative analysis of the flavonoids in raw propolis from northern Croatia. Kosalec, Ivan; Bakmaz, Marina; Pepeljnjak, Stjepan; Vladimir-Knezevic, Sanda. Institute of Microbiology Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia. Acta Pharmaceutica (Zagreb, Croatia) (2004), 54(1), 65-72. Publisher: Croatian Pharmaceutical Society, CODEN: ACPHEE ISSN: 1330-0075. Journal written in English. CAN 141:137026 AN 2004:302581 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Formulations contg. citrus polymethoxylated flavones (PMF), mainly tangeretin, or citrus flavanone glucosides hesperidin and naringin were evaluated for blood cholesterol-lowering potential in hamsters with diet-induced hypercholesterolemia. PMF metabolites were also investigated. Diets contg. 1% PMF decreased blood serum total and very-low-d. lipoprotein (VLDL) + LDL cholesterol by 19-27 and 32-40%, resp., and decreased serum triacylglycerol levels. Comparable decreases were achieved by feeding 3% mixt. of hesperidin and naringin (1:1), implying lower hypolipidemic potency of the hesperidin/naringin mixt. vs. PMF. HPLC-MS anal. identified high blood serum, liver, and urine concns. of tangeretin metabolites, including dihydroxytrimethoxyflavone and monohydroxytetramethoxyflavone glucuronides and aglycons. The total liver concns. of tangeretin derivs. corresponded to hypolipidemic concns. of intact tangeretin in earlier expts. in vitro. PMF may be novel flavonoids with cholesterol- and triacylglycerol-lowering potential. Elevated liver levels of PMF metabolites may be directly responsible for their hypolipidemic effects in vivo.

Abstract

Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced hypercholesterolemia. Kurowska, Elzbieta M.; Manthey, John A. KGK Synergize Inc., London, ON, Can. Journal of Agricultural and Food Chemistry (2004), 52(10), 2879-2886. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 141:38062 AN 2004:322142 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


caffeic acid did not yield the corresponding flavanones. We have also cloned and partially characterized a new tyrosine ammonia lyase from Rhodobacter sphaeroides. Tyrosine ammonia lyase was substituted for phenylalanine ammonia lyase and cinnamate-4-hydroxylase in our E. coli clones and three different growth media were tested. After 48 h induction, high-level prodn. (20.8 mg L-1) of naringenin in metabolically engineered E. coli was obsd. for the first time.


flavanone

Proteomic analysis on symbiotic differentiation of mitochondria in soybean nodules. Hoa, Le Thi-Phuong; Nomura, Mika; Kajiwara, Hideyuki; Day, David Alexander; Tajima, Shigeyuki. Department of Life Science, Faculty of Agriculture, Kagawa University, Kagawa, Japan. Plant and Cell Physiology (2004), 45(3), 300-308. Publisher: Japanese Society of Plant Physiologists, CODEN: PCPHA5 ISSN: 0032-0781. Journal written in English. CAN 141:85768 AN 2004:284264 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Nucleotide variation in eight effectively unlinked genes was surveyed in species-wide samples of the closely related outbreeding species Arabidopsis halleri and A. lyrata ssp. petraea and in three of these genes in A. lyrata ssp. lyrata and A. thaliana. Significant genetic differentiation was obsd. more frequently in A. l. petraea than in A. halleri. Av. ests. of nucleotide variation were highest in A. l. petraea and lowest in A. l. lyrata, reflecting differences among species in effective population size. The low level of variation in A. l. lyrata is concordant with a bottleneck effect assocd. with its origin. The A. halleri/A. l. petraea speciation process was studied, considering the orthologous sequences of an outgroup species (A. thaliana). The high no. of ancestral mutations relative to exclusive polymorphisms detected in A. halleri and A. l. petraea, the significant results of the multilocus Fay and Wu H tests, and haplotype sharing between the species indicate introgression subsequent to speciation. Av. among-population variation in A. halleri and A. l. petraea was .apprx.1.5- and 3-fold higher than that in the inbreeder A. thaliana. The detected redn. of variation in A. thaliana is less than that expected from differences in mating system alone, and therefore from selective processes related to differences in the effective recombination rate, but could be explained by differences in population structure.

Abstract

Multilocus analysis of variation and speciation in the closely related species Arabidopsis halleri and A. lyrata. Ramos-Onsins, Sebastian E.; Stranger, Barbara E.; Mitchell-Olds, Thomas; Aguade, Montserrat. Departament de Genetica, Facultat de Biologia, Universitat de Barcelona, Barcelona, Spain. Genetics (2004), 166(1), 373-388. Publisher: Genetics Society of America, CODEN: GENTAE ISSN: 0016-6731. Journal written in English. CAN 141:20487 AN 2004:296073 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The acetone ext. of Sophora flavescens (Leguminosae) exhibited lethal activity against Trypanosoma cruzi. Column chromatog. sepn. of the ext. guided by trypanocidal activity afforded a new prenylated flavanone (4), together with nine known flavonoids: sophoraflavanone G (1), (-)-kurarinone (2), kushenol L (3), 2'-methoxykurarinone (5), 7,4'-dihydroxy-5-methoxy-8-(γ,γ-dimethylallyl)-flavanone (6), leachianone A (7), 8-prenylnaringenin (8), noranhydroicaritin (9) and alopecurone G (10). The structure of the new flavanone 4 was detd. on the basis of spectroscopic analyses. The min. lethal concns. of these compds. against epimastigotes of T. cruzi were 3.7 μM (1), 14 μM (2), 7.1 μM (3), 7.2 μM (4), 6.9 μM (5), 71 μM (6), 5.5 μM (7), 18 μM (8), 4.4 μM (9) and 3.6 μM (10).

Abstract

Trypanocidal flavonoids from Sophora flavescens. Matsuo, Kenji; Ito, Michiho; Honda, Gisho; Qui, Tran Kim; Kiuchi, Fumiyuki. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, Japan. Natural Medicines (Tokyo, Japan) (2003), 57(6), 253-255. Publisher: Japanese Society of Pharmacognosy, CODEN: NMEDEO ISSN: 1340-3443. Journal written in English. CAN 141:363081 AN 2004:301938 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

In the search for new proteinase inhibitors we have focused on the screening and Computer Assisted Drug Design (CADD) studies of polyphenolic compds. In this paper we report CADD of flavonoles and flavones as trypsin inhibitors concomitant by the screening

Abstract

Structural aspects of flavonoids as trypsin inhibitors. Maliar, Tibor; Jedinak, Andrej; Kadrabova, Jana; Sturdik, Ernest. VULM, Modra, Slovakia. European Journal of Medicinal Chemistry (2004), 39(3), 241-248. Publisher: Elsevier Science Ltd., CODEN: EJMCA5 ISSN: 0223-5234. Journal written in English. CAN 140:417263 AN 2004:271052 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A reversed-phase high-performance liq. chromatog. (HPLC) sepn. with photo-diode array detection was developed for the simultaneous detn. of flavonoids extd. from Citrus bergamia juice. It employs a C18 reversed-phase column and a linear gradient elution system with methanol/water with 5% acetic acid (vol./vol.), as mobile phase. The method was validated in terms of detection limits (LOD), quantitation limits (LOQ), linearity, precision and accuracy. Limits of detection ranged from a low of 0.007 mg mL-1 (narirutin) to a high of 0.018 mg mL-1 (didymin). The limits of quantitation were between a low of 0.011 mg mL-1 (7-OH flavanone) and a high of 0.024 mg mL-1 (didymin). An excellent linear response was obsd. over the range specified for all analytes, as confirmed by the correlation coeff. with ranged from 0.9982 and 0.9999. The intra-day R.S.D.% ranged from 0.11 to 3.64%. The intermediate precision R.S.D.% were not higher than 7.62%. The accuracy of the method was confirmed with an av. recovery ranging, except for neoeriocitrin, between 88.07% and 102.45%. Since the extn. conditions can affect analyte recovery, a suitable optimization strategy of the procedure was needed. The exptl. parameters optimized were extn. time, temp., and solvents. A multivariate approach was used to provide direct evaluation of the selected variables and related interactions. The D-optimal design was constructed by applying the exchange algorithm. All exptl. results were computed by NEMROD-W software. This methodol. led us to obtain the best recovery for all the flavonoids in the least no. of expts.

Abstract

Study of the extraction procedure by experimental design and validation of a LC method for determination of flavonoids in Citrus bergamia juice. Calabro, M. L.; Galtieri, V.; Cutroneo, P.; Tommasini, S.; Ficarra, P.; Ficarra, R. Facolta di Farmacia, Dipartimento Farmaco-Chimico, Universita di Messina, Messina, Italy. Journal of Pharmaceutical and Biomedical Analysis (2004), 35(2), 349-363. Publisher: Elsevier Science B.V., CODEN: JPBADA ISSN: 0731-7085. Journal written in English. CAN 141:70418 AN 2004:281860 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Symbiotic interactions between legume plants and rhizobia induce specific metabs. and intracellular organelles in nodules. For surveying symbiotic differentiation of a key organelle, mitochondria, protein constituents of soybean nodule and root mitochondria were compared after two-dimensional electrophoresis, and the proteins were characterized in combination with matrix-assisted desorption/ionization time-of-flight mass spectrometry, electrospray ionization mass spectrometry and N-terminal amino acid sequencing. Of the proteins that were detected only in nodule mitochondria, phosphoserine aminotransferase, flavanone 3-hydroxylase, coproporphyrinogen III oxidase, one ribonucleoprotein and three unknown proteins were identified. Seven up-regulated, eight down-regulated and two strongly suppressed protein spots in nodule mitochondria were also assigned protein identities. The physiol. roles of these differential expressions were discussed in relation to nodule-specific metabs. in soybean nodules.

Abstract


flavanone

Answer 800:

This paper presents the synthesis and characterization of new halogenated ether derivs. of flavans, flavanols and flavanones, obtained by reaction of the corresponding Me ethers with hydrogen halides in the presence of dimethyldioxirane as an oxidative agent.

Abstract

Synthesis of new halogenated flavonoids by reaction with hydrogen halides in the presence of dimethyldioxirane. Arnone, Alberto; Nasini, Gianluca; Panzeri, Walter; Vajna de Pava, Orso; Zucca, Cristina. Politecnico di Milano, Dipartimento di Chimica, Materiali ed Ingegneria Chimica "Giulio Natta", C.N.R. Istituto di Chimica del Riconoscimento Molecolare Sezione A. Quilico, Milan, Italy. Journal of Chemical Research, Synopses (2003), (11), 683-684, M1141-M1150. Publisher: Science Reviews, CODEN: JRPSDC ISSN: 0308-2342. Journal written in English. CAN 141:173989 AN 2004:265780 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The estrogenic flavanone rac-8-prenylnaringenin (8-PN) and 3 derivs. (rac-7-(O-prenyl)naringenin-4'-acetate (7-O-PN), rac-5-(O-prenyl)naringenin-4',7-diacetate (5-O-PN), and rac-6-(1,1-dimethylallyl)naringenin (6-DMAN) were prepd. by chem. synthesis and analyzed with respect to their toxicity and possible cell cycle effects in human acute myeloid leukemia (HL-60) cells. With the exception of 5-O-PN, all the other naringenins showed only weak toxic effects at concns. below 50 μmol/l. A cell cycle anal. over several cell generations up to 4 days was carried out using the fluorescent dye carboxyfluorescein diacetate N-succinimidyl ester (CFSE) followed by propidium iodide (PI) staining at the end of the expt. The well-studied flavonol quercetin was included in the anal. as a ref. substance. All flavonoids affected cell proliferation, but the extent and the resulting changes in the proliferation pattern were specific for each substance. In contrast to the radical scavenging activity of quercetin, the tested flavanones showed no anti-oxidative properties using several different test systems. Similarly, the mitochondrial membrane potential (ΔΨm) was hardly effected by these compds., while both menadione and quercetin strongly reduced the potential after 1 h of treatment. The reported chem. modification of interesting lead substances (like the strongly estrogenic 8-PN) presents a promising approach to modulate the properties of a relevant substance in a pharmacol. desirable way. The low toxicity and weak cytostatic properties of the tested naringenin derivs. is encouraging for further studies on known naringenin target mols.

Abstract

Toxicity and Cell Cycle Effects of Synthetic 8-Prenylnaringenin and Derivatives in Human Cells. Tokalov, Sergey V.; Henker, Yvonne; Schwab, Pia; Metz, Peter; Gutzeit, Herwig O. Institut fuer Zoologie, TU Dresden, Dresden, Germany. Pharmacology (2004), 71(1), 46-56. Publisher: S. Karger AG, CODEN: PHMGBN ISSN: 0031-7012. Journal written in English. CAN 141:133681 AN 2004:267933 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


results. 5,7-Dihydroxy flavonoid have been found to be a perspective trypsin/trypsin-like-enzyme inhibitor. Flavanones and isoflavones are less effective trypsin inhibitors due to a lost of the optimal geometry leading to hydrogen bond interactions. Four different interaction modes were obsd., flavonoids are stabilized in S1 region of β-trypsin by formation of two (apigenin) or at least one hydrogen bond and other significant electrostatic interactions. Quercetin, myricetin and morin have shown to be the best trypsin inhibitors tested. In general, flavonoids with suitably located hydroxy groups and planar conformation are the building blocks able to replace guanidinobenzoyl part of successful inhibitors. Physiol. nature of flavonoids reveals biotechnol. source of new trypsin inhibitors as antipancreatitis, anticancer and anti-inflammation drugs.


flavanone

Biosynthetic production of flavonoid and isoflavonoid nutraceuticals by genetic manipulation of enzymes in plants. Dixon, Richard A.; Liu, Chang-jun; Deavours, Bettina. (The Samuel Roberts Noble Foundation, Inc., USA). PCT Int. Appl. (2004), 80 pp. CODEN: PIXXD2 WO 2004024079 A2 20040325 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2003-US28454 20030910. Priority: US 2002-409447 20020910. CAN 140:282425 AN


A review. Antitumor effects of flavonoid by the inhibition of cancer cell proliferation is reviewed including the classification of flavonoid such as flavan, flavone, flavonol, flavanol, isoflavone, flavanone, chalkone, and anthocyanidin, as well as its antitumor mechanism through genetic regulation and p53-RB pathway with examples.

Abstract

Growth inhibition of cancer by flavonoid. Yoshida, Tatsushi; Sakai, Toshiyuki. Department of Molecular-Targeting Cancer Prevention, Graduate School of Medical Science, Kyoto Prefectural University of Medicine, Kyoto, Japan. Ketsueki, Shuyoka (2003), 47(6), 571-574. Publisher: Kagaku Hyoronsha, CODEN: KETSBI ISSN: 0915-8529. Journal; General Review written in Japanese. CAN 141:16670 AN 2004:256603 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavonoids represent a diverse group of natural pigments widely distributed in the plant kingdom and are an important component of human diet due to their high content in fruits and vegetables. Since many flavonoids have been shown to be potent inhibitors, substrates, and even inducers of various cytochrome P 450 isoforms, there is considerable interest in studying interactions of this class of mols. with the cytochrome P 450 enzyme system. In this study, the metab. of several simple flavanones by rat liver microsomes was investigated and compared. In addn. to the expected arom. hydroxylation products, several novel metabolic pathways were obsd. including C-ring desatn. to form the corresponding flavones, oxidn. of the B-ring to generate an unusual quinol oxidn. product, B-ring cleavage with the formation of chromone derivs., and redn. of carbonyl group to form flavan-4-ol derivs. The metabolites were characterized and identified primarily by using liq. chromatog.-tandem mass spectrometry with comparison to authentic stds. Formation of flavones from dietary flavanones might have biol. significance since flavones often exhibit pharmacol. activities that are different from those of flavanones. However, little is known about the pharmacol. activities of the other types of flavanone metabolites.

Abstract

New metabolic pathways for flavanones catalyzed by rat liver microsomes. Nikolic, Dejan; Van Breemen, Richard B. Department of Medicinal Chemistry and Pharmacognosy, UIC/National Institutes of Health Center for Botanical Dietary Supplements Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA. Drug Metabolism and Disposition (2004), 32(4), 387-397. Publisher: American Society for Pharmacology and Experimental Therapeutics, CODEN: DMDSAI ISSN: 0090-9556. Journal written in English. CAN 141:133508 AN 2004:263276 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Anti-inflammatory activities of two flavanones, sigmoidin A and sigmoidin B, from Erythrina sigmoidea. Njamen, Dieudonne; Mbafor, Joseph Tanyi; Fomum, Zacharias Tanee; Kamanyi, Albert; Mbanya, Jean-Claude; Recio, M. Carmen; Giner, Rosa M.; Manez, Salvador; Rios, Jose Luis. Laboratory of Animal Physiology, Department of Animal Biology and Physiology, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon. Planta Medica (2004), 70(2), 104-107. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 140:332102 AN 2004:242555 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention provides method and compns. for the modulation of flavanone and/or isoflavone prodn. in plants. Transgenic plants having novel phenotypes are generated by down-regulating flavanone 3-hydroxylase by loss-of-function mutations or antisense oligonucleotides, and up-regulation of isoflavone synthase, chalcone isomerase, and/or chalcone synthase by cloning their genes into the recipient plants. Introduction of isoflavone synthase into plants in which the flavanone 3-hydroxylase is down-regulated results in significant improvement to the levels of accumulation of the isoflavone genistein; this can be coupled with increasing flux into the prodn. of naringenin to result in even further enhancement of isoflavone prodn. Increased expression of isoflavones in particular in plants may be used to increase the nutritional value of food plants for both human and animal consumption. The invention overcomes limitations of the prior art which prevented accumulation of high levels of isoflavones in plants.

Abstract WO 2003-US28454 W 20030910US 2002-409447P P 20020910Priority Application NZ 538259 A 20080328 NZ 2003-538259 20030910


EP 1555870 A2 20050727 EP 2003-752235 20030910US 20040128711 A1 20040701 US 2003-659755 20030910AU 2003270537 B2 20080320AU 2003270537 A1 20040430 AU 2003-270537 20030910

RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW

WO 2004024079 A3 20050519WO 2004024079 A2 20040325 WO 2003-US28454 20030910Patent No. Kind Date Application No. Date Patent Family Information 2004:252297 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Naringenin from Citrus junos Has an Inhibitory Effect on Acetylcholinesterase and a Mitigating Effect on Amnesia. Heo, Ho Jin; Kim, Mi-Jeong; Lee, Jung-Min; Choi, Soo Jung; Cho, Hong-Yon; Hong, Bumshik; Kim, Hye-Kyung; Kim, Eunki; Shin, Dong-Hoon. Graduate School of Biotechnology, Korea University, Seoul, S. Korea. Dementia and Geriatric Cognitive Disorders (2004), 17(3), 151-157. Publisher: S. Karger AG, CODEN: DGCDFX ISSN: 1420-8008. Journal written in English. CAN 141:236293 AN 2004:238126 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Red wine is a rich source of polyphenolic components such as anthocyanins and flavonoids. The inhibitory effects of red wine polyphenolics on human breast cancer cells have been demonstrated earlier, but their effects on normal cells have not been fully established. Red wine (Merlot) was fractionated by hydrophobic interaction chromatog. and different flavonoid fractions with increasing hydrophobicity were obtained. These fractions were tested for their inhibitory effect on human breast cancer cells (MCF-7), normal human mammary epithelial cells (HMEC), and a non-tumorigenic MCF-10A cell line. By contrast to the authentic flavonoids such as quercetin, naringenin and catechin which inhibited the growth of HMEC much more than that of MCF-7 cancer cells, a red wine fraction, that was comprised mainly of the flavonoid aglycons, showed maximal inhibition of the growth of breast cancer cells, with relatively low cytotoxicity towards HMEC and MCF-10A cells. In the presence of this flavonoid fraction, the normal cells grew normally, whereas the breast cancer cells underwent a change in morphol. into spherical forms. Cytotoxicity analyses suggested that these cells had become apoptotic. The efficiency of inhibition of cell proliferation by various flavonoid fractions appeared to be related to their inhibition of calcium and calmodulin-promoted phosphodiesterase activity, suggesting that flavonoids may interfere with calcium second messenger function. The results suggest that certain grape wine ingredients have anticancer properties and these ingredients may be helpful for developing designer functional foods with cancer-preventive properties.

Abstract

Selective Cytotoxicity of a Red Grape Wine Flavonoid Fraction Against MCF-7 Cells. Hakimuddin, Fatima; Paliyath, Gopinadhan; Meckling, Kelly. Department of Food Science, University of Guelph, Guelph, ON, Can. Breast Cancer Research and Treatment (2004), 85(1), 65-79. Publisher: Kluwer Academic Publishers, CODEN: BCTRD6 ISSN: 0167-6806. Journal written in English. CAN 141:288645 AN 2004:241380 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two prenylated flavanones isolated from Erythrina sigmoidea Hua (sigmoidin A and sigmoidin B) were studied for their ability to inhibit the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and arachidonic acid metab. In addn., the compds. were studied in two exptl. models of inflammation induced in mouse ears by 12-O-tetradecanoylphorbol 13-acetate (TPA) and the phospholipase A2-induced mouse paw edema. Both sigmoidins A and B proved to be potent scavengers of the DPPH radical, while the study of the inhibition of arachidonic acid metab. demonstrated that these same compds. were selective inhibitors of 5-lipoxygenase, with no effect on cyclooxygenase-1 activity. Dose-response inhibitor potency was established for sigmoidin A (IC50 = 31 μM). In the assay of phospholipase A2-induced mouse paw edema, only the sigmoidin B deriv. inhibited edema formation at 60 min, showing a percentage of inhibition below that obtained with cyproheptadine (59% vs. 74%). In the TPA test, sigmoidins A and B decreased the induced edema by 89% and 83%, resp. This is the first time that the anti-inflammatory activity and antioxidant properties of these prenylflavanones have been reported. The results indicate that the compds. have different mechanisms of action depending on whether one or two prenyl groups are present in ring B.

Abstract


flavanone

Previous studies demonstrated that hydroxyl groups play important roles in the antioxidative activities of flavonoids; however, the importance of structurally related hydroxylation in their apoptosis-inducing activities is still undefined. In the present study, flavanone with hydroxylation at C4' and C6 had a significant cytotoxic effect in human leukemia HL-60 cells accompanied by the occurrence of DNA ladders, apoptotic bodies, and hypodiploid cells, characteristics of apoptosis. The replacement of a hydroxyl group (OH) by a methoxyl (OCH3) group at C4' or C6 attenuated the apoptotic effect in cells, and there was no significant cytotoxicity of flavanone or flavanone with OH or OCH3 in C7-treated HL-60 cells. Induction of enzyme activity of caspase-3 and -9, but not caspase-1 and -8,

Abstract

Hydroxylation at C4' or C6 is essential for apoptosis-inducing activity of flavanone through activation of the caspase-3 cascade and production of reactive oxygen species. Ko, Ching Huai; Shen, Shing-Chuan; Chen, Yen Chou. School of Pharmacy, Graduate Institute of Pharmaceutical Sciences, Taipei Medical University, Taipei, Taiwan. Free Radical Biology & Medicine (2004), 36(7), 897-910. Publisher: Elsevier, CODEN: FRBMEH ISSN: 0891-5849. Journal written in English. CAN 141:98988 AN 2004:213137 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In aq. soln., Medicago sativa chalcone isomerase (CHI) enhances the reaction rate for the unimol. rearrangement of chalcone (CHN) into flavanone by seven orders of magnitude. Conformations of CHN and their relative free energies in water and CHI were investigated by the thermodn. perturbation method. In water, CHN adopts two conformations (I and II) with conformation I being higher in energy than conformation II by 3 kcal/mol. Only I can give rise to a near attack conformer (NAC) where the nucleophile O2' and the electrophile C9 are placed in proximity. In CHI, I binds less tightly than II by ≈ 2 kcal/mol, resulting in the free energy for NAC formation being ≈ 2 kcal/mol higher in the enzyme than in water. This unfavorable feature in the ground state of the CHI reaction requires the predominant catalytic advantage to be taken in the step of NAC → transition state (TS). From the mol. dynamics simulations of apo-CHI, CHI complexed with CHN (CHI⋅CHN) and CHI⋅TS, the authors found: (i) Lys-97-general-acid catalysis of the O2'- nucleophilic addn.; (ii) expulsion of three water mols. in the process of TS formation; (iii) release of enzyme structural distortion on TS formation. In the conclusion, CHI's remarkable efficiency of stabilizing the TS and its relatively poor ability in organizing the ground state is compared with chorismate mutase whose catalytic prowess, when compared with water, originates predominantly from the enhanced NAC population at the active site.

Abstract

Transition state stabilization by general acid catalysis, water expulsion, and enzyme reorganization in Medicago savita chalcone isomerase. Hur, Sun; Newby, Zachary E. R.; Bruice, Thomas C. Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA, USA. Proceedings of the National Academy of Sciences of the United States of America (2004), 101(9), 2730-2735. Publisher: National Academy of Sciences, CODEN: PNASA6 ISSN: 0027-8424. Journal written in English. CAN 140:352558 AN 2004:231195 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This study was performed to identify safe and more effective acetylcholinesterase (AChE) inhibitors in the treatment of Alzheimer's disease. The total methanol ext. of Citrus junos had a significant inhibitory effect on AChE in vitro. By sequential fractionation of C. junos, the active component was finally identified as naringenin. Naringenin inhibited AChE activity in a dose-dependent manner. In this study, we also evaluated the anti-amnesic activity of naringenin, a major flavanone constituent isolated from C. junos, in vivo using ICR mice with amnesia induced by scopolamine (1 mg/kg body wt.). Naringenin, when administered to mice at 4.5 mg/kg body wt., significantly ameliorated scopolamine-induced amnesia as measured in both the passive avoidance and the Y-maze test. These results suggest that naringenin may be a useful chemopreventive agent against Alzheimer's disease.


flavanone

Significance of C-terminal sequence elements for Petunia flavanone 3β-hydroxylase activity. Wellmann, Frank; Matern, Ulrich; Lukacin, Richard. Institut fur Pharmazeutische Biologie, Philipps-Universitat Marburg, Marburg, Germany. FEBS Letters (2004), 561(1-3), 149-154. Publisher: Elsevier Science B.V., CODEN: FEBLAL ISSN: 0014-5793. Journal written in English. CAN 140:402307 AN 2004:192433 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention relates to an inhibitor of type-2 helper T cell (Th2)-derived cytokine, suitable for use in a cosmetic or food to prevent hyperactive Th2-related symptoms, e.g. allergic inflammation and atopic symptoms, etc., wherein the inhibitor contains catechin deriv., flavonol deriv., flavanone deriv. coumarin deriv. Vitis seed ext., Fuscoporia ext., and/or Malus peel ext. The effect of Fuscoporia obliqua ext. on IL-4, INF-γ, and Th1/Th2 in peripheral blood mononuclear cells (PBMC) cells was examd. A cosmetic cream contg. Fuscoporia obliqua ext. 3 % was formulated, and applied to patients with atopic dermatitis.


Type-2 helper T cell-derived cytokine inhibitors containing defined natural components. Kishida, Kotaro; Uno, Katsuko; Tanaka, Hiroshi; Kitatani, Noritake. (Narisu Cosmetic Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2004), 12 pp. CODEN: JKXXAF JP 2004075619 A 20040311 Patent written in Japanese. Application: JP 2002-239293 20020820. Priority: . CAN 140:222916 AN 2004:198515 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The apoptosis-inducing activity of 4'-OH- or 6-OH-flavanone was also obsd. in another leukemia cell line (Jurkat), but was not found in mature monocytic cells (THP-1) and normal human polymorphonuclear neutrophils (PMNs). This suggests that hydroxylation at C4' or C6 is important to the apoptosis-inducing activities of flavanone through ROS prodn., and that activation of the caspase-3 cascade, downstream of caspase-9 activation, is involved.

accompanied by release of cytochrome C from mitochondria to cytosol and the appearance of cleaved of PARP (85 kDa), D4-GDI (23 kDa), and caspase-3 (p17/p15) fragments, was identified in 4'-OH- or 6-OH- flavanone-treated HL-60 cells. Caspase-3 and -9 inhibitors Ac-DEVD-FMK and Ac-LEHD-FMK, but not caspase-1 and -8 inhibitors Ac-YVAD-FMK and Ac-LETD-FMK, attenuated 4'-OH- or 6-OH-flavanone-induced cell death. And, inhibition of caspase-9 activity by Ac-LEHD-FMK suppresses caspase-3 protein procession induced by 4'-OH- and 6-OH-flavanone, indicative of caspase-9 activation locating upstream of caspase-3. A decrease in the antiapoptotic protein Mcl-1 and increases in the pro-apoptotic proteins Bax and Bad were found in 4'-OH- or 6-OH-flavanone-treated HL-60 cells. Induction of endogenous ROS prodn. was detected in 4'-OH- or 6-OH-flavanone-treated HL-60 cells by the DCHF-DA assay. Antioxidants such as N-acetylcysteine (NAC), catalase (CAT), superoxide dismutase (SOD), and allopurinol (ALL), but not pyrrolidine dithiocarbamate (PDTC) or diphenylene iodonium (DPI), significantly inhibited 4'-OH- or 6-OH-flavanone-induced ROS prodn., with blocking of the apoptosis induced by 4'-OH- or 6-OH-flavanone.


flavanone

Leaves of Chrysanthemum morifolium cv. Ramat were extd. sequentially with hexane, Et acetate, and methanol. The methanol fraction, when incorporated into artificial diet, was found to reduce the growth of cabbage looper (Trichoplusia ni Hubner) larvae at concns. between 500 and 5000 ppm of diet. Fractionation of the methanol ext. on a Sephadex column yielded five fractions, three of which reduced the wt. of larvae relative to the control. One fraction was analyzed using HPLC and found to contain three main constituents. These compds. were purified using a combination of gel permeation chromatog. on Sephadex LH20 and HPLC, and analyzed by 1H and 13C NMR as well as undergoing chem. and phys. analyses. The compds. were identified as chlorogenic acid, 3,5-O-dicaffeoylquinic acid. and 3',4',5-trihydroxyflavanone 7-O-glucuronide. At concns. between 100 to 1000 ppm, these compds. reduced both growth and photosynthesis of Lemna gibba L. with the order of efficacy being flavanone > chlorogenic acid > 3,5-O-dicaffeoylquinic acid. Furthermore, when incorporated sep. into an artificial diet, these compds., at 10 to 1000 ppm, enhanced or

Abstract

A flavanone and two phenolic acids from Chrysanthemum morifolium with phytotoxic and insect growth regulating activity. Beninger, Clifford W.; Abou-Zaid, Mamdouh M.; Kistner, Adrienne L. E.; Hallett, Rebecca H.; Iqbal, Muhammad J.; Grodzinski, Bernard; Hall, J. Christopher. Department of Environmental Biology, University of Guelph, Guelph, ON, Can. Journal of Chemical Ecology (2004), 30(3), 589-606. Publisher: Kluwer Academic/Plenum Publishers, CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 141:239809 AN 2004:185175 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review with 44 refs. on advances in study on chem. constituents in Hypericum Linn. with subdivision headings: (1) dianthranone derivs.; (2) flavanone alcs.; (3) flavones and flavone alcs.; (4) xanthones; (5) coumarins; (6) phenolic acids; phloroglucinols; (8) volatile oils; and (9) others.

Abstract

Advances in study on chemical constituents in Hypericum Linn. Lu, Hongfei; Chu, Qinggang; Hu, Zhenghai. College of Life and Environment Science, Zhejiang Normal University, Jinhua, Peop. Rep. China. Zhongcaoyao (2002), 33(12), 1135-1138. Publisher: Zhongcaoyao Zazhi Bianjibu, CODEN: CTYAD8 ISSN: 0253-2670. Journal; General Review written in Chinese. CAN 140:353626 AN 2004:187678 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavanone 3β-hydroxylase (FHT), a 2-oxoglutarate-dependent dioxygenase (2-ODD), catalyzes the hydroxylation of (2S)-flavanones to (2R/3R)-dihydroflavonols in plants as a key step towards the biosynthesis of flavonols, anthocyanins and catechins. Crystallog. studies of 2-ODDs typically revealed a jelly roll in the enzyme core, and the C-terminus of the enzyme polypeptides was proposed to form a lid covering the active site cavity, thereby reducing the chances for oxidative or proteolytic damage and unfolding. Moreover, it has been proposed that in some cases the C-terminus is involved in substrate selectivity of 2-ODDs. In a systematic approach with highly active Petunia FHT, four C-terminally truncated enzyme forms were generated by deletion of five, 11, 24 or 29 amino acids. The recombinant FHTs preserved their substrate selectivity, but the specific activity decreased gradually with the extent of truncation. An enzyme chimera was subsequently constructed by a domain swapping approach, thereby replacing the C-terminal 52 amino acids of Petunia FHT with the equiv. region of flavonol synthase (FLS) from Citrus unshiu, an enzyme that shows ambiguous FLS and FHT activity. The chimeric dioxygenase still revealed exclusively FHT activity, albeit at a moderate level. The data predict that the selectivity of FHT is not governed by the C-terminal sequence that accounts for about 13% of the enzyme polypeptide chain.

Abstract


flavanone


Two kinds of flavonoids from Sophora flavescens Aits, dihydroflavonoids and dihydroflavonols, were studied by using electrospray ionization tandem mass spectrometry(ESI-MSn). [M-H]- of these two kinds of flavonoids were obsd. in the neg. ion mode under ESI conditions, which provided us the mol. wts. of them. Cross-ring reactions, arisen from MS2 spectra of both dihydroflavonoids and dihydroflavonols, gave the fragment ions by the loss of neutral species. The differences of their cleavage positions were then proposed, dihydroflavonoids cleave at C2-O bond and C4-C10 bond, but dihydroflavonols cleave at C2-O bond and C3-C4 bond. The loss of neutral species from dihydroflavonoids and dihydroflavonols were also discussed, the former were several relative big neutral species, while the latter were some small species, such as CO, CO2, H2O and B-ring. The differences between dihydroflavonoids and dihydroflavonols were mainly arisen by hydroxy group at C-3 of the C-ring, which were the characteristic for dihydroflavonoids and dihydroflavonols under the ESI-MSn conditions.

Abstract

Studies on flavonoids from Sophora flavescens ait using ESI-MS. Bai, Yu; Guo, Ming-Quan; Song, Feng-Rui; Liu, Zhi-Qiang; Liu, Shu-Ying. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Peop. Rep. China. Gaodeng Xuexiao Huaxue Xuebao (2004), 25(2), 284-288. Publisher: Gaodeng Jiaoyu Chubanshe, CODEN: KTHPDM ISSN: 0251-0790. Journal written in Chinese. CAN 140:353674 AN 2004:175474 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytophthora citrophthora causes serious losses in Citrus fruits through brown rot lesion. The effect of infection with P. citrophthora on Citrus sinensis (cv. Valencia Late) fruits was studied, with particular ref. to the levels of the flavanones hesperidin and isonaringin and the polymethoxyflavones sinensetin, nobiletin, tangeretin, and heptamethoxyflavone, because flavonoids are most probably involved as natural defense or resistance mechanisms in this genus. Changes in the levels of these flavonoids were detected after infection. The hesperidin and isonaringin contents fell by 13 and 67%, resp., whereas the contents of their corresponding aglycons, hesperetin and naringenin, increased, suggesting the hydrolyzing effect of this fungus on the glycosylated flavanones. The heptamethoxyflavone, nobiletin, sinensetin, and tangeretin levels increased by 48, 28, 26, and 24%, resp. The in vitro study revealed that these compds. acted as antifungal agents, the most active being the aglycons (naringenin and hesperetin), followed by the polymethoxyflavones and flavanone glycosides. The participation of these flavonoids in the defense mechanism of this Citrus species is discussed.

Abstract

Changes in the Levels of Polymethoxyflavones and Flavanones as Part of the Defense Mechanism of Citrus sinensis (Cv. Valencia Late) Fruits against Phytophthora citrophthora. Del Rio, J. A.; Gomez, P.; Baidez, A. G.; Arcas, M. C.; Botia, J. M.; Ortuno, A. Plant Biology Department Faculty of Biology, University of Murcia, Espinardo, Spain. Journal of Agricultural and Food Chemistry (2004), 52(7), 1913-1917. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 140:353759 AN 2004:178988 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


reduced growth of the cabbage looper (Trichoplusia ni) and gypsy moth (Lymantria dispar L.).


flavanone

Xanthohumol metabolites in feces of rats. Nookandeh, Aslieh; Frank, Norbert; Steiner, Frank; Ellinger, Renate; Schneider, Bernd; Gerhauser, Clarissa; Becker, Hans. Institute for Pharmacognosy and Analytical Phytochemistry, University of the Saarland, Saarbrucken, Germany. Phytochemistry (Elsevier) (2004), 65(5), 561-570. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 140:399280 AN 2004:173234 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The compds. of flavonoid, an important group in nature, can prevent coronary heart disease and anticancer by virtue of the characteristics of antioxidn. Nine flavonoids most often seen in grape wine, namely apigenin, baicalein, naringenin, luteolin, hesperetin, galangin, kaempferol, quercetin, and myricetin, were detd. HPLC and CZE. A successful resoln. was obtained from an unusual additive of THF in mobile phase by HPLC. One notable thing is that the mixt. of luteolin and quercetin could be sepd. for the first time by HPLC. In addn., the better detection limit was still attainable even with the use of THF. The detection limits of CZE performed in borate buffer were hundreds-fold better than in previous reports. Furthermore, the retention and migration behavior of the analytes studied were discussed. As the result of this study, the elution order of flavone and flavanone was reversed to the contention proposed by Wulf et al. It was predictable from the interaction with THF. Consequently, the exts. from grape wine with solid-phase extn. were analyzed by developing methods of HPLC and CZE. The obtained recoveries ranged from 90 to 107% and the relative std. deviations were under 6.3%.

Abstract

Determination of flavonoids by high-performance liquid chromatography and capillary electrophoresis. Wang, Shu-Ping; Huang, Kuo-Jun. Department of Applied Chemistry, Providence University, Hsien, Taiwan. Journal of Chromatography, A (2004), 1032(1-2), 273-279. Publisher: Elsevier Science B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 140:286370 AN 2004:174136 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effect of solar radiation on flavonoid biosynthesis was studied in bilberry (Vaccinium myrtillus L.) leaves. Expression of flavonoid pathway genes of bilberry was studied in the upper leaves of bilberry, exposed to direct sunlight, in the shaded leaves growing lower in the same plants and in fruits. Bilberry-specific digoxigenin-dUTP-labeled cDNA fragments of five genes from the general phenylpropanoid pathway coding phenylalanine ammonia-lyase and from the flavonoid pathway coding chalcone synthase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, and anthocyanidin synthase were used as probes in gene expression anal. Anthocyanins, catechins, proanthocyanidins, flavonols and hydroxycinnamic acids from the leaves and fruits were identified and quantified using high-performance liq. chromatog. combined with a diode array detector. An increase in the expression of the studied flavonoid pathway genes was obsd. in leaves growing under direct sun exposure. Also, the concns. of anthocyanins, catechins, flavonols and hydroxycinnamic acids were higher in the leaves exposed to direct sunlight. However, the concn. of polymeric procyanidins was lower in sun-exposed leaves, whereas that of prodelphinidins was slightly increased. The results give further support for the protective role of flavonoids and hydroxy cinnamic acids against high solar radiation in plants. Also, the roles of different flavonoid compds. as a defense against stress caused by sun exposure is discussed.

Abstract

Activation of flavonoid biosynthesis by solar radiation in bilberry (Vaccinium myrtillus L.) leaves. Jaakola, Laura; Maeaettae-Riihinen, Kaisu; Kaerenlampi, Sirpa; Hohtola, Anja. Department of Biology/Botany, University of Oulu, Oulu, Finland. Planta (2004), 218(5), 721-728. Publisher: Springer-Verlag, CODEN: PLANAB ISSN: 0032-0935. Journal written in English. CAN 141:36210 AN 2004:175033 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Bilberry (Vaccinium myrtillus L.) is the characteristic understory species in boreal forests. In Northern Europe it is among the most important wild berries. Bilberry is preferably a shade plant and when growing under direct sunlight, the upper leaves of the plants turn red. This phenomenon is regarded to provide protection against UV-B irradn. via the prodn. of anthocyanins and other protective flavonoids. The aim of the present study was to clarify the role of flavonoid biosynthesis of the bilberry plants growing in the direct sunlight. Expression of flavonoid pathway genes of bilberries was studied in the upper leaves of bilberry, exposed to direct sunlight, in the shade leaves growing lower in the same plants and in berries. Bilberry-specific digoxigenin-dUTP labeled cDNA fragments of five

Abstract

Flavonoid biosynthesis in bilberry (Vaccinium myrtillus L.). Jaakola, L.; Hohtola, A.; Maatta, K.; Torronen, R.; Karenlampi, S. Department of Biology/Botany, University of Oulu, Oulu, Finland. Acta Horticulturae (2003), 618 415-419. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 141:36206 AN 2004:165424 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Camellia sinensis (tea) is a com. important crop that is valued for its secondary metabolites. Higher levels of catechins are accumulated in young leaves than in mature leaves. To understand the mol. regulation of secondary metab. in tea leaves, differentially expressed genes of interest should be identified, cloned, and studied in detail. A total of 588 cDNA clones from a subtractive cDNA library were randomly picked, sequenced, and analyzed. High-quality sequences were isolated for 508 of these clones. BlastX comparisons indicated that about 8.7% of the clones encoded enzymes involved in secondary metab., with a particularly high abundance of flavonoid-metab. proteins (5.1%). These ESTs facilitated the isolation and characterization of genes involved in the flavonoid pathway in tea: chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), flavonoid 3',5'-hydroxylase (F3'5'H), flavonol synthase (FLS), dihydroflavonol 4-reductase (DFR), and leucoanthocyanidin reductase (LCR). The three genes encoding F3H, DFR, and LCR were more highly expressed in young leaves than in mature leaves. These results indicate that flavonoid biosynthesis genes from tea are differentially regulated in the developmental stages. The subtractive cDNA library and EST database described in this study represent a valuable resource for future research aimed at improving economically important secondary metabolic characteristics in crops.

Abstract

EST analysis of genes involved in secondary metabolism in Camellia sinensis (tea), using suppression subtractive hybridization. Park, Jong-Sug; Kim, Jung-Bong; Hahn, Bum-Soo; Kim, Kyung-Hwan; Ha, Sun-Hwa; Kim, Jong-Bum; Kim, Yong-Hwan. RDA, Metabolic Engineering Division, National Institute of Agricultural Biotechnology, Suwon, S. Korea. Plant Science (Amsterdam, Netherlands) (2004), 166(4), 953-961. Publisher: Elsevier, CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 141:48191 AN 2004:169536 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Xanthohumol (1), isolated from hop, was fed to rats in a dose of 1000 mg kg-1 body wt. The feces of the animals were collected after 24 and 48 h and analyzed for metabolites of 1. Approx. 89% of the recovered flavonoid-compds. consisted of unchanged 1. Sixteen metabolites and six previously known metabolites were isolated and characterized by coupling techniques (HPLC-NMR, HPLC-MS and HPLC-DAD). Their structures were elucidated by spectroscopic methods, esp. using NMR spectroscopy. Twenty metabolites had a modified chalcone structure and two metabolites were flavanone derivs.

Abstract


flavanone

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, EP 1394248 A1 20040303 EP 2002-255669 20020814JP 3734463 B2 20060111JP 2004065209 A 20040304 JP 2002-233324 20020809US 7049427 B2 20060523US 20040038407 A1 20040226 US 2002-224493 20020821Patent No. Kind Date Application No. Date Patent Family Information

Protein and cDNA sequences modified dominant-negative Mazus chalcone synthase and uses therefor. Hanummappa, Mamatha; Choi, Goh; Choi, Giltsu. (Korea Kumho Petrochemical Co., Ltd, S. Korea). U.S. Pat. Appl. Publ. (2004), 18 pp. CODEN: USXXCO US 2004038407 A1 20040226 Patent written in English. Application: US 2002-224493 20020821. Priority: . CAN 140:212059 AN 2004:162364 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Irradn. is rapidly becoming the preferred method of quarantine treatment against fruit flies for citrus fruit and improving shelf life of the fruit during storage. Citrus fruit contain several biol. active functional components that are known to prevent chronic diseases such as cancer and cardiovascular diseases. The preventative activity has been assocd. with polyphenol content in citrus fruit. RioRed grapefruit (Citrus paradisi) were harvested in the middle of Mar., 2001 and exposed to gamma irradn. from a Cs137 source at levels recommended to control fruit flies (0, 150, 300 Gy) and then stored at 10 °C and 90-95% relative humidity (RH) for 36 days, followed by an addnl. 20 days at 20 °C to simulate marketing conditions. Stored fruit treated with 300 Gy had less water loss compared to other treatments. Irradn. treatments had no consistent effect on total sol. solids (TSS) and titratable acidity. Stem end breakdown and peel pitting were slightly higher in fruits treated with 300 Gy at the end of the storage period. Irradiated fruits had higher total phenolic content than controls during storage. Fruits irradiated with 300 Gy had higher flavanone content (naringin, narirutin and total flavanones) compared with control, immediately after irradn. and at the end of the storage. Organoleptic characters were more affected by storage than by irradn. treatments. Sensory panel preferred fruits exposed to 300 Gy irradn. after the storage compared to other treatments. Irradn. may be useful in retaining the beneficial flavanones that have been shown to have preventative effect on degenerative diseases in addn. to insect control.

Abstract

Ionizing radiation and storage effects on postharvest quality of Rio Red grapefruit. Vanamala, J. K. P.; Cobb, B. G.; Pike, L. M.; Patil, B. S. Department of Horticultural Sciences, Texas A+M University, College Station, TX, USA. Acta Horticulturae (2003), 628(Vol. 2, Issues and Advances in Postharvest Horticulture, Volume 2), 635-641. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 140:405856 AN 2004:165381 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


genes from the flavonoid pathway, phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR), and anthocyanidin synthase (ANS), were used as probes for detg. the expression of the flavonoid pathway genes in bilberries. The results indicate the activation of the expression of flavonoid pathway genes in bilberry leaves exposed to the direct sunlight.


flavanone

Suppression of infection-induced endotoxin shock in mice by a Citrus flavanone naringin. Kawaguchi, Kiichiro; Kikuchi, Sei-ichi; Hasunuma, Ryoichi; Maruyama, Hiroko; Ryll, Roland; Kumazawa, Yoshio. Medicinal Plant Garden, School of


Amyloid β protein (Aβ)-induced free radical-mediated neurotoxicity is known as a leading hypothesis for a cause of Alzheimer's disease. Aβ increased free radical prodn. and lipid peroxidn. in PC12 nerve cells, resulting in apoptosis and cell death. The protective effect of naringenin, a major flavanone constituent isolated from Citrus junos, against Aβ-induced neurotoxicity was investigated using PC12 cells. Pretreatment with isolated naringenin and vitamin C prevented the generation of the Aβ-induced reactive oxygen species. Naringenin resulted in the decrease of Aβ toxicity in a manner of concn. dependence, which was assessed by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. However, treatment with these antioxidants inhibited the Aβ-induced neurotoxic effect. The antiamnestic activity of naringenin in vivo was also evaluated using ICR mice with amnesia induced by scopolamine (1 mg/kg body wt.). Naringenin, when administered to ICR mice at 4.5 mg/kg body wt., significantly ameliorated scopolamine-induced amnesia as measured in the passive avoidance test. Therefore, these results indicate that micromol. Aβ-induced in vitro oxidative cell stress is reduced by naringenin and naringenin may be a useful chemopreventive agent against a neurodegenerative disease such as Alzheimer's disease.

Abstract

Effect of Antioxidant Flavanone, Naringenin, from Citrus junos on Neuroprotection. Heo, Ho Jin; Kim, Dae-Ok; Shin, Soo Cheol; Kim, Mi Jeong; Kim, Byung Gee; Shin, Dong-Hoon. Department of Food Science and Technology, Cornell University, Geneva, NY, USA. Journal of Agricultural and Food Chemistry (2004), 52(6), 1520-1525. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 140:297366 AN 2004:158228 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention includes modified Mazus chalcone synthase (CHS) nucleic acids, which encode a modified chalcone synthase that has alanine instead of cysteine at the 165 th amino acid of Mazus CHS and either glycine or lysine instead of methionine at the 138 th amino acid of Mazus CHS. The property of the encoded modified Mazus CHS is characterized by its dominant-neg. inhibition of CHS. The invention also includes plants having at least one cell expressing the modified Mazus CHS. Such plants are characterized by the decreased content of anthocyanins. The invention also includes vectors comprising at least a portion of the modified Mazus CHS nucleic acids. The invention also includes methods using such vectors for producing plants having the decreased content of anthocyanins.

Abstract JP 2002-233324 A 20020809US 2002-224493 A 20020821Priority Application KR 2002087927 A 20021123 KR 2002-69616 20021111 CN 1478894 A 20040303 CN 2002-141485 20020830

TR, BG, CZ, EE, SK


flavanone

Abstract

Synthesis, fungicidal activity and quantitative structure-activity relationships of novel flavanone derivatives. Yang, Guang-Fu; Ding, Yu; Yang, Hua-Zheng; Wu, Xiao-Jun. College of Chemistry, Central China Normal University, Wuhan, Peop. Rep. China. Gaodeng Xuexiao Huaxue Xuebao (2004), 25(1), 71-75. Publisher: Gaodeng Jiaoyu Chubanshe, CODEN: KTHPDM ISSN: 0251-0790. Journal written in Chinese. CAN 140:406652 AN 2004:105281 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The female flowers of hops are used throughout the world as a flavoring agent for beer. Recently, there has been increasing interest in the potential estrogenic properties of hop exts. Among the possible estrogenic compds. in hops, 8-prenylnaringenin is perhaps most significant due to its high in vitro potency exceeding that of other known phytoestrogens. Since data regarding the pharmacokinetic properties of this compd. are lacking, we investigated the in vitro metab. of 8-prenylnaringenin by human liver microsomes. A total of 12 metabolites were identified, and biotransformation occurred on the prenyl group and the flavanone skeleton. The major site of oxidn. was on the terminal Me groups, and of the two possible isomers, the trans isomer was more abundant. The double bond on the prenyl group was also oxidized to an epoxide that was opened by intramol. reaction with the neighboring hydroxyl group. On the flavanone skeleton, the major site of oxidn. was at 3' position on the B ring. Other metabolites included oxidn. at carbon-3 as well as desatn. of the C ring to produce 8-prenylapigenin. An unusual hydroxy quinone product formed by ipso hydroxylation of the B ring of 8-prenylnaringenin was also detected. This product was probably an intermediate for the B ring cleavage product, 8-prenylchromone.

Abstract

Metabolism of 8-prenylnaringenin, a potent phytoestrogen from hops (Humulus lupulus), by human liver microsomes. Nikolic, Dejan; Li, Yongmei; Chadwick, Lucas R.; Grubjesic, Simonida; Schwab, Pia; Metz, Peter; van Breemen, Richard B. Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL, USA. Drug Metabolism and Disposition (2004), 32(2), 272-279. Publisher: American Society for Pharmacology and Experimental Therapeutics, CODEN: DMDSAI ISSN: 0090-9556. Journal written in English. CAN 141:16823 AN 2004:141147 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The protective effect of the Citrus flavanone naringin was demonstrated in an endotoxin shock model based on Salmonella infection. I.p. infection with 108 CFU Salmonella typhimurium aroA caused lethal shock in lipopolysaccharide (LPS) -responder but not LPS-non-responder mice. Administration of 1 mg naringin 3 h before infection resulted in protection from lethal shock, similar to LPS-non-responder mice. The protective effect of naringin was time- and dose-dependent. Treatment with naringin resulted not only in a significant decrease in bacterial nos. in spleens and livers, but also in a decrease in plasma LPS levels. In addn., naringin markedly suppressed TNF-α and normalized the activated states of blood coagulation factors such as prothrombin time, fibrinogen concn. and platelet nos. caused by infection. Interestingly, treatment with naringin suppressed high levels of sol. CD14 and high mobility group-1 mol. caused by infection.

Abstract

Pharmaceutical Sciences, Kitasato University, Japan. Planta Medica (2004), 70(1), 17-22. Publisher: Georg Thieme Verlag, CODEN: PLMEAA ISSN: 0032-0943. Journal written in English. CAN 140:296938 AN 2004:156702 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


Crop species in the Solanaceae, which includes tomato (Lycopersicon esculentum), potato (Solanum tuberosum), pepper (Capsicum spp.), and eggplant (S. melongena), exhibit natural variation in the types, levels, and tissue-specific expression patterns of anthocyanin pigments. While the identities of the genes underpinning natural variation in anthocyanin traits in these crops are largely unknown, many structural genes and regulators of anthocyanin biosynthesis have been isolated from the solanaceous ornamental species Petunia. To identify candidate genes that may correspond to loci controlling natural variation in the four crops, 13 anthocyanin-related genes were localized on a tomato F2 genetic map. Gene map positions were then compared to mapped mutants in tomato and through comparative genetic maps to natural variants in potato, eggplant, and pepper. Similar map positions suggest that the tomato mutants anthocyaninless, entirely anthocyaninless, and anthocyanin gainer correspond to flavonoid 3'5'-hydroxylase (f3'5'h), anthocyanidin synthase, and the Petunia Myb domain transcriptional regulatory gene an2, resp. Similarly potato R, required for the prodn. of red pelargonidin-based pigments, P, required for prodn. of purple delphinidin-based pigments, and I, required for tissue-specific expression in tuber skin, appear to correspond to dihydroflavonol 4-reductase, f3'5'h and an2, resp. The map location of an2 also overlaps pepper A and eggplant fap10.1, lla10.1, lra10.1, sa10.1, pa10.1 and ca10.1, suggesting that a homologous regulatory locus has been subjected to parallel selection in the domestication of many solanaceous crops. To test the hypothesis that tomato anthocyaninless corresponds to f3'5'h, a portion of the gene was sequenced. A premature stop codon was obsd. in an anthocyaninless mutant, but not in wild-type.

Abstract

Candidate gene analysis of anthocyanin pigmentation loci in the Solanaceae. De Jong, W. S.; Eannetta, N. T.; De Jong, D. M.; Bodis, M. Department of Plant Breeding, Cornell University, Ithaca, NY, USA. Theoretical and Applied Genetics (2004), 108(3), 423-432. Publisher: Springer-Verlag, CODEN: THAGA6 ISSN: 0040-5752. Journal written in English. CAN 141:2031 AN 2004:95065 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

R

R'

I

Fourteen novel flavanone derivs. I (R = Me, Cl; R' = Cl, NO2, Me, OMe, OCH2Ph, OCH2Ph-4-Cl) were designed and synthesized, and structures were confirmed by 1H NMR, MS and elemental anal. Title compds. fungicidal IC50 in vitro against rice blast disease were tested and the quant. relationship between their structures and fungicidal activities was analyzed by using comparative mol. field anal. (CoMFA) and Hansch-Fujita approach. The results show that the hydrophobicity, polarity effect and the energy of the highest unoccupied orbital are very important to fungicidal activity. If the mol. was easy to polarize and had a lower LUMO energy, it would show a high fungicidal activity. Correlation results show that lgK is the most suitable parameter to describe the hydrophobicity of the title compds. compared to two other hydrophobic parameters, .sum.π and clgP. The results of 3D-QSAR anal. suggests that the introduction of steric bulk group onto the 2,3,4-position and small steric bulk onto the 6-position of B ring will be favorable to the activity of the compd. The CoMFA analyses on the electronic property requirement are consistent with those derived from the Hansch-Fujita approach.


flavanone

Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Rechner, Andreas R.; Smith, Martin A.; Kuhnle, Gunter; Gibson, Glenn R.; Debnam, Edward S.; Srai, S. Kaila S.; Moore, Kevin P.; Rice-Evans, Catherine A. School of Biomedical Sciences, Wolfson Centre for Age-Related Diseases, Antioxidant Research Group, King's College London, London, UK. Free Radical Biology & Medicine (2004), 36(2), 212-225. Publisher: Elsevier, CODEN: FRBMEH ISSN: 0891-5849.


We have recently reported the presence of the anxiolytic flavone 6-methylapigenin (MA) and of the sedative and sleep-enhancing flavanone glycoside 2S (-) hesperidin (HN) in Valeriana officinalis and Valeriana wallichii. MA, in turn, was able to potentiate the sleep-inducing properties of HN. The present paper reports the identification in V. officinalis of the flavone glycoside linarin (LN) and the discovery that it has, like HN, sedative and sleep-enhancing properties that are potentiated by simultaneous administration of valerenic acid (VA). These effects should be taken into account when considering the pharmacol. actions of valeriana exts.

Abstract

Sedative and sleep-enhancing properties of linarin, a flavonoid-isolated from Valeriana officinalis. Fernandez, Sebastian; Wasowski, Cristina; Paladini, Alejandro C.; Marder, Mariel. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica Biologicas, Buenos Aires, Argent. Pharmacology, Biochemistry and Behavior (2004), 77(2), 399-404. Publisher: Elsevier Science Inc., CODEN: PBBHAU ISSN: 0091-3057. Journal written in English. CAN 140:264360 AN 2004:78728 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review. The genus Dorstenia contains many plants that are used as anti-infection, anti-snakebite and anti-rheumatic remedies in the medicinal plant therapy of several countries in Africa, Central and South America. The genus is now recognized as a rich source of prenyl and geranyl-substituted coumarins, chalcones, flavanones, flavones and flavonols. Three naturally occurring styrenes were reported from D. barnimiana. The geranyl substituted furocoumarin, O-[3-(2,2-dimethyl-3-oxo-2H-furan-5-yl)butyl]bergaptol, has been found in many species. D. poinsettifolia furnished the unusual substituted 4-phenyldihydrofurocoumarin. Prenylated and geranylated flavonoids have so far been reported only from African Dorstenia species. 5, 3'-Digeranyl-3,4,2',4'-tetrahydroxychalcone isolated from D. proropens, is the only example of a bis-geranylated chalcone in the literature. A part from 7,8- (2,2-dimethylpyrano-4'-methoxyflavanone ( dorspoinsettifolin) from D. poinsettifolia and 3',4'- (2,2-dimethylpyrano-6-prenyl-7-hydroxyflavanone (dinklagin A) from D. dinklagei, all flavanone derivs. named dorsmanins A - J described here are from D. mannii. These dorsmanins appear to be derived from 6,8-diprenyl-5,7,3',4'-tetrahydroxyflavanone and a possible biosynthetic scheme for them is presented. D. Zenkeri yield a bichalcone deriv. which is believed to arise from dorstenone another prenylated bichalcone isolated from D. barteri. The latter is probably formed via an enzymic Diels-Alder reaction of 3'-prenyl-4,2',4'-trihydroxychalcone (isobavachalcone) and its dehydroderivative. D. psilurus provided all the triprenylated flavonoids found so far in Dorstenia and, of these, dorsilurin E is unique having ring B of the flavonoid structure modified to a dienone. The pharmacol. data on this genus are scanty. Exts. of D. multiradiata show antileishmanial activity. Exts. and /or compds. from other species show anti-inflammatory, analgesic, anti-oxidant and citotoxic activities.

Abstract

The chemistry and pharmacology of the genus Dorstenia (Moraceae). Ngadjui, Bonaventure T.; Abegaz, Berhanu M. Department of Organic Chemistry, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon. Studies in Natural Products Chemistry (2003), 29(Bioactive Natural Products (Part J)), 761-805. Publisher: Elsevier Science B.V., CODEN: SNPCE2 Journal; General Review written in English. CAN 140:353612 AN 2004:83826 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The optically-active flavanones or chromanones I (R1, R2 = H, OH, alkoxy, alkyl, hydroxyalkyl; R3 = Me, Ph which may be substituted with OH and/or alkoxy) are prepd. by (1) treating dithiane or dithiolane derivs. II (R = H; R1, R2 = same as above; X = F, Cl; n = 2, 3) (III) with bases and reacting with optically-active epoxides IV (R3 = same as above), (2) cyclizing the resulting optically-active alc. II (R = CH2CHR3OH; R1, R2, R3, X, n = same as above) (V) upon treatment with bases, and (3) hydrolyzing the resulting optically-active spiro compd. VI (R1, R2, R3, n = same as above). BuLi was added dropwise to a THF soln. of III (R1 = R2 = H, X = F, n = 3), prepd. by reacting 2-FC6H4CHO with HS(CH2)3SH, at -18° and the reaction mixt. was stirred for 3 h. The reaction mixt. was treated with (S)-(-)-propylene oxide for a day to give 71.0% (-)-V (R1 = R2 = H, R3 = Me, X = F, n = 3). This was treated with Me3COK at 80° for 30 min and further treated with addnl. Me3COK under reflux for 1 h to give 90.7% (-)-VI (R1 = R2 = H, R3 = Me, n = 3). A mixt. of HgCl2, CaCO3, and MeCN/H2O was stirred at room temp. for 1 h and treated with an acetone soln. of the spiro compd. for 3 h to give 74.0% (-)-I (R1 = R2 = H, R3 = Me).


Preparation of optically-active flavanones or chromanones from dithiane or dithiolane derivatives. Noda, Yoshihiro. (Nihon University, Japan). Jpn. Kokai Tokkyo Koho (2004), 10 pp. CODEN: JKXXAF JP 2004026726 A 20040129 Patent written in Japanese. Application: JP 2002-185820 20020626. Priority: . CAN 140:128274 AN 2004:76471 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The metab. of chlorogenic acid, naringin, and rutin, representative members of three common families of dietary polyphenols, the hydroxycinnamates, the flavanones, and the flavonols, resp., was studied in an in vitro mixed culture model of the human colonic microflora. Time- and concn.-dependent degrdn. of all three compds. was obsd., which was assocd. with the following metabolic events after cleavage of the ester or glycosidic bond: redn. of the aliph. double bond of the resulting hydroxycinnamate caffeic acid residue; dehydroxylation and ring fission of the heterocyclic C-ring of the resulting deglycosylated flavanone, naringenin, and of the deglycosylated flavonol, quercetin (which differed depending on the substitution). The metabolic events, their sequences, and major phenolic end products, as identified by GC-MS or LC-MS/MS, were elucidated from the structural characteristics of the investigated compds. The major phenolic end products identified were 3-(3-hydroxyphenyl)-propionic acid for chlorogenic acid, 3-(4-hydroxyphenyl)-propionic acid and 3-phenylpropionic acid for naringin, and 3-hydroxyphenylacetic acid and 3-(3-hydroxyphenyl)-propionic acid for rutin. The degree of degrdn. of the compds. studied was significantly influenced by the substrate concn. as well as individual variations in the compn. of the fecal flora. The results support extensive metab. of dietary polyphenols in the colon, depending on substrate concn. and residence time, with resultant formation of simple phenolics, which can be considered biomarkers of colonic metab. if subsequently absorbed. It is also apparent that a relatively small no. of phenolic degrdn. products are formed in the colon from the diverse group of natural polyphenols.

Abstract Journal written in English. CAN 140:374511 AN 2004:78576 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous Bibliographic Information Answer 831:

Citrus beverages are often part of our daily diet. Recent animal, case and cohort control as well as epidemiol. studies have shown that certain functional components [carotenoids (lycopene and β-carotene), limonoids, flavones (naringin and naringin rutinoside), folate, and vitamin C] of citrus prevent chronic diseases such as cancer and cardiovascular diseases. Functional components from 3 single strength com. "Rio Red" grapefruit (Citrus paradisi Macf.) juice products namely cartons (100% pure fresh juice and not from conc.), cans (100% juice from conc.), and cocktails (35% juice from conc.), were analyzed by reverse phase liq. chromatog. The levels of vitamin C significantly decreased when half-gal grapefruit juice cartons were stored at 4°C for six weeks, but the levels of limonin 17-β-D glucopyranoside (LG) were not affected during the same period. Total flavanone and lycopene levels were significantly higher at 6 wk compared to initial levels. Although a significant loss of vitamin C levels was found when cans were stored at room temp. (24°C) for 12 mo, LG levels were markedly increased during the same period. Furthermore, total flavanone and carotenoid levels were changed during storage, but no specific trend was obsd. When cocktail in polyethylene toluene (PET) containers was stored at room temp., the levels of vitamin C were significantly decreased; however, LG and lycopene levels were increased. Our expts. suggest that the functional components in grapefruit juice change during storage, depending on the container used. To remain competitive in international and national markets, optimization of these components may be important for the processing industry.

Abstract

Functional components in citrus beverages. Patil, Bhimanagouda S. Kingsville Citrus Center, Texas A and M University, Weslaco, TX, USA. ACS Symposium Series (2004), 871(Nutraceutical Beverages), 103-122. Publisher: American Chemical Society, CODEN: ACSMC8 ISSN: 0097-6156. Journal written in English. CAN 140:286508 AN 2004:73018 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

O

SS

O

O

SS

R1

2R3

*

RX

R1

2R

CH 2 n

R

R3*

R1

2R

CH 2 n

R3*

I

V IIV

II


flavanone

Abstract

Effect of flavonoids on feeding preference and development of the crucifer pest Mamestra configurata Walker. Onyilagha, Joseph C.; Lazorko, Jennifer; Gruber, Margaret Y.; Soroka, Juliana J.; Erlandson, Martin A. Saskatoon Research Centre, Agriculture and Agri-Food Canada, Saskatoon, SK, Can. Journal of Chemical Ecology (2004), 30(1), 109-124. Publisher: Kluwer Academic/Plenum Publishers, CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 140:401732 AN 2004:66446 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Certain naturally occurring flavonoids affect immunoregulatory activities in vitro and in vivo against cytokine prodn. Since tumor necrosis factor (TNF)-α is one of the major inflammatory cytokines, the effects of various dietary flavonoids on TNF- α prodn. in lipopolysaccharide (LPS)-stimulated J774.1 cells were evaluated in vitro. Flavones, flavonols, and chalcone are the most potent inhibitors of prodn. of TNF-α. Flavanone, naringenin, anthocyanidin, pelargodinin, and cyanidin exhibit moderate inhibitory activity. In contrast, genistein isoflavone displays weak inhibition, while eriodictyol flavanone is inactive. It is clear that the double bond between carbons 2 and 3 and the ketone group at position 4 of flavonoids are necessary for potent inhibitory effect. The difference in inhibitory action appears to depend on the categorized subclass of flavonoids.

Abstract

Inhibitory Effect of Some Flavonoids on Tumor Necrosis Factor-α Production in Lipopolysaccharide-Stimulated Mouse Macrophage Cell Line J774.1. Mudiyanselage Theja Herath, Herath; Takano-Ishikawa, Yuko; Yamaki, Kohji. Industrial Technology Institute, Colombo, Sri Lanka. Journal of Medicinal Food (2003), 6(4), 365-370. Publisher: Mary Ann Liebert, Inc., CODEN: JMFOFJ ISSN: 1096-620X. Journal written in English. CAN 141:167193 AN 2004:68470 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Naringenin and hesperetin, the aglycons of the flavanone glucosides naringin and hesperidin occur naturally in citrus fruits. They exert a variety of pharmacol. effects such as antioxidant, blood lipid-lowering, anticarcinogenic and inhibit selected cytochrome P 450 enzymes resulting in drug interactions. A specific, sensitive, precise, and accurate solid-phase extn. HPLC assay for the simultaneous detn. of naringenin and hesperetin in human plasma was developed and validated. After addn. of 7-ethoxycoumarin as internal std., plasma samples were incubated with β-glucuronidase/sulfatase, and the analytes were isolated from plasma by solid-phase extn. using C18 cartridges and sepd. on a C8 reversed phase column with MeOH/H2O/HOAc (40:58:2, vol./vol./v) as the eluent at 45°. The method was linear in the 10-300 ng/mL concn. range for both naringenin and hesperetin (r > 0.999). Recovery for naringenin, hesperetin and internal std. was >76.7%. Intra- and inter-day precision for naringenin ranged from 1.4 to 4.2% and from 1.9 to 5.2%, resp., and for hesperetin ranged from 1.3 to 4.1% and from 1.7 to 5.1%, resp. Accuracy was better than 91.5 and 91.3% for naringenin and hesperetin, resp.

Abstract

determination of naringenin and hesperetin in human plasma. Kanaze, Feras Imad; Kokkalou, Eugene; Georgarakis, Manolis; Niopas, Ioannis. School of Health Sciences, Department of Pharmacy, Aristotle University of Thessaloniki, Thessaloniki, Greece. Journal of Chromatography, B: Analytical Technologies in the Biomedical and Life Sciences (2004), 801(2), 363-367. Publisher: Elsevier B.V., CODEN: JCBAAI ISSN: 1570-0232. Journal written in English. CAN 140:245964 AN 2004:69538 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Chalcone dibromide on treatment with Ph hydrazine hydrochloride or isonicotinic acid hydrazide afforded the corresponding 3,5-diaryl-1-phenyl/isonicotinoyl-2-pyrazolines, e.g., I, which have also been obtained from chalcones under similar conditions. Further, some of the chalcones on treatment with acetoacetic ester have been converted to the corresponding 3,5-diaryl-6-carbethoxycyclohex-2-en-1-ones, e.g., I. Structure elucidation has been done on the basis of elemental anal. and spectral studies. The synthesized compds. have been screened for their antibacterial and the pyrazolines for both antibacterial and herbicidal activities.

Abstract

Synthesis and biological activity of some new 3,5-diaryl-1-phenyl/isonicotinoyl-2-pyrazolines and 3,5-diaryl-6-carbethoxy cyclohexenone derivatives. Vijayvergiya, Deepika; Kothari, Seema; Verma, B. L. Department of Chemistry, Faculty of Science, M.L. Sukhadia University, Udaipur, India. Indian Journal of Heterocyclic Chemistry (2003), 13(2), 105-110. Publisher: Prof. R. S. Varma, CODEN: IJCHEI ISSN: 0971-1627. Journal written in English. CAN 141:225382 AN 2004:38752 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Fire blight, caused by Erwinia amylovora, is a in pome fruit disease. Hitherto, an effective control could only be achieved by using antibiotics, but this implies potential risks for human health, livestock and environment. A new approach allows transient inhibition of a step in the flavonoid pathway, thereby inducing the formation of a novel antimicrobial 3-deoxyflavonoid controlling fire blight in apple and pear leaves. This compd. is closely related to natural phytoalexins in sorghum. The approach does not only provide a safe method to control fire blight: Resistance against different pathogens is also induced in other crop plants. Treatment with prohexadione-Ca led to luteoliflavan accumulation in apple leaves. Synthetic luteoforol controlled E. amylovora, in vitro. An overview is given of the flavanone 4-reductase activity of various crops.

Abstract

Induction of antimicrobial 3-deoxyflavonoids in pome fruit trees controls fire blight. Halbwirth, Heidrun; Fischer, Thilo C.; Roemmelt, Susanne; Spinelli, Francesco; Schlangen, Karin; Peterek, Silke; Sabatini, Emidio; Messina, Christian; Speakman, John-Bryan; Andreotti, Carlo; Rademacher, Wilhelm; Bazzi, Carlo; Costa, Guglielmo; Treutter, Dieter; Forkmann, Gert; Stich, Karl. Institute of Technical BioScience, Technical University of Vienna, Vienna, Austria. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2003), 58(11/12), 765-770. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 140:248645 AN 2004:64742 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Thirty-seven flavonoid compds. (9 flavones, 18 flavonols, 8 flavanones, and 2 flavanonols) were investigated for their effect on feeding choice with bertha armyworm (Mamestra configurata Walker; BAW). Feeding choice was dependent upon subtle differences in biochem. structure. Unsubstituted flavone and flavanone were the strongest feeding deterrents in the choice bioassay, while 7,4'-dihydroxyflavone and dihydroquercetin stimulated BAW to feed. The constitutive flavonoids of Brassica napus, isorhamnetin-3-sophoroside-7-glucoside and kaempferol-3,7-diglucoside, were effective deterrents when supplemented at concns. higher than endogenous levels. In a no-choice bioassay, flavone reduced both larval wt. as well as larval and pupal development time.


flavanone

Synthesis and fungicidal activity of flavanone derivatives containing isopentenyl group. Hu, Li-Hong; Qin, Zhang-Lan; Li, Chao; Huang, Qin; Wang, Fen-Hua. Department of Chemistry, Central China Normal University, Wuhan, Peop. Rep. China.


The isomerization of 2'-hydroxychalcones to their corresponding flavanones, in good to excellent yield using silica supported-Bi(III) chloride as a catalyst under dry conditions at 70-80°C is reported.

Abstract

An improved procedure for the isomerisation of 2'-hydroxy-substituted chalcones to flavanones using silica supported-BiCl3 under dry conditions. Ahmed, Naseem; Ansari, W. H. Dep. Chem., Aligarh Muslim Univ., Aligarh, India. Journal of Chemical Research, Synopses (2003), (9), 572-573. Publisher: Science Reviews, CODEN: JRPSDC ISSN: 0308-2342. Journal written in English. CAN 140:217414 AN 2004:27751 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


NN

OMe

Br

Br

HO

O

N

O

OH OMe

CO 2Et

I

II


flavanone

Method to increase isoflavonoid levels through genetic engineering to modulate to gene expression in phenylpropanoid biosynthetic pathway in transgenic plants. McGonigle, Brian; Odell, Joan T. (E. I. Du Pont de Nemours & Co., USA). PCT Int. Appl. (2003), 55 pp. CODEN: PIXXD2 WO 2003106633 A2 20031224 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2003-US18663 20030612. Priority: US 2002-388280 20020613. CAN 140:56623 AN 2003:1007113 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Anthocyanidin synthase (ANS), flavonol synthase (FLS), and flavanone 3β-hydroxylase (FHT) are involved in the biosynthesis of flavonoids in plants and are all members of the family of 2-oxoglutarate- and ferrous iron-dependent oxygenases. ANS, FLS, and FHT are closely related by sequence and catalyze oxidn. of the flavonoid "C ring"; they have been shown to have overlapping substrate and product selectivities. In the initial steps of catalysis, 2-oxoglutarate and dioxygen are thought to react at the ferrous iron center producing succinate, carbon dioxide, and a reactive ferryl intermediate, the latter of which can then affect oxidn. of the flavonoid substrate. Here the authors describe work on ANS, FLS, and FHT utilizing several different substrates carried out in 18O2/16OH2, 16O2/18OH2, and 18O2/18OH2 atmospheres. In the 18O2/16OH2 atmosphere close to complete incorporation of a single 18O label was obsd. in the dihydroflavonol products (e.g. (2R,3R)-trans-dihydrokaempferol) from incubations of flavanones (e.g. (2S)naringenin) with FHT, ANS, and FLS. This and other evidence supports the intermediacy of a reactive oxidizing species, the oxygen of which does not exchange with that of water. In the case of products formed by oxidn. of flavonoid substrates with a C-3 hydroxyl group (e.g. (2R,3R)-trans-dihydroquercetin), the results imply that oxygen exchange can occur at a stage subsequent to initial oxidn. of the C-ring, probably via an enzyme-bound C-3 ketone/3,3-gem-diol intermediate.

Abstract

Mechanistic Studies on Three 2-Oxoglutarate-dependent Oxygenases of Flavonoid Biosynthesis: anthocyanidin synthase, flavonol synthase, and flavanone 3β-hydroxylase. Turnbull, Jonathan J.; Nakajima, Jun-ichiro; Welford, Richard W. D.; Yamazaki, Mami; Saito, Kazuki; Schofield, Christopher J. The Dyson Perrins Laboratory, The Oxford Centre for Molecular Sciences, Oxford, UK. Journal of Biological Chemistry (2004), 279(2), 1206-1216. Publisher: American Society for Biochemistry and Molecular Biology, CODEN: JBCHA3 ISSN: 0021-9258. Journal written in English. CAN 140:249135 AN 2004:10881 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Twelve isopentenyl flavanone derivs. were synthesized by the Friedel-Crafts reaction of isopentenyl cinnamic acid with substituted phenols, giving the products with yield 69% to 30%. The structures of title compds. were confirmed by elemental anal., IR, 1H NMR and MS. The phys., chem. and spectroscopic properties of these compds. were characterized. Biol. test showed that some of compds. had good fungicidal activity towards Anthracnosis cucumaria, Rhizotonia Solani Kuhn, Piricularia oryzae Cav, Fusarium graminearum Schwabe. It indicated that isopentenyl substituents might eventually enhance fungicidal activity of this kind of compds.

Abstract

Yingyong Huaxue (2003), 20(12), 1161-1165. Publisher: Kexue Chubanshe, CODEN: YIHUED ISSN: 1000-0518. Journal written in Chinese. CAN 140:321205 AN 2004:11346 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Abstract

Constituents of the stem bark of Pongamia pinnata with the potential to induce quinone reductase. [Erratum to document cited in CA139:320060]. Carcache-Blanco, Esperanza J.; Kang, Young-Hwa; Park, Eun Jung; Su, Bao-Ning; Kardono, Leonardus B. S.; Riswan, Soedarsono; Fong, Harry H. S.; Pezzuto, John M.; Kinghorn, A. Douglas. Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL, USA. Journal of Natural Products (2004), 67(1), 126. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 140:420632 AN 2003:1001851 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This invention pertains to methods of increasing isoflavonoid prodn. in isoflavonoid-producing plants by transforming plants with at least one construct expressing at least a portion of a flavanone 3-hydroxylase, a C1 myb transcription factor, and an R-type myc transcription factor that regulate expression of genes in the phenylpropanoid pathway. Specifically, isoflavone levels in Glycine max (soybean) are increased via metabolic engineering of the complex phenylpropanoid biosynthetic pathway through suppression of flavanone 3-hydroxylase (F3H) to block the anthocyanin branch of the pathway, in combination with expressing C1/R fusion protein CRC to activate other related gene expression. The F3H suppression vector AC21 contains a portion of FSH gene (antisense presumably, not specified, under the control of a seed-specific promoter) that can promote formation of a stem loop structure and thus inhibit F3H gene expression. The CRC vector (pOY135) encodes a fusion protein (under the control of phaseolin promoter) which contain corn C1 myb domain to amino acid 125, the entire coding region of the Lc allele of R, and C1 transcription activation domain (from amino acid 126 to the C-terminus of C1). Higher levels of isoflavones (4-times than wild-type), and decreased genistein and increased the daidzein levels are detected in transgenic soybean seed.

Abstract WO 2003-US18663 W 20030612US 2002-388280P P 20020613Priority Application AU 2003236501 A1 20031231 AU 2003-236501 20030612 US 7189895 B2 20070313US 20040006795 A1 20040108 US 2003-459159 20030611


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW



flavanone

An Arabidopsis thaliana T-DNA mutagenized population (GABI-Kat) for flanking sequence tag-based reverse genetics. Rosso, Mario G.; Li, Yong; Strizhov, Nicolai; Reiss, Bernd; Dekker, Koen; Weisshaar, Bernd. GABI-Kat, Max Planck Institute for Plant Breeding Research, Cologne, Germany. Plant Molecular Biology (2003), 53(1-2), 247-259. Publisher: Kluwer Academic Publishers, CODEN: PMBIDB ISSN: 0167-4412. Journal written in English. CAN 140:247814 AN 2003:985380 CAPLUS


Chromatog. sepns. are an expanding technol. for the sepn. of high value products, particularly in the area of pharmaceutics, food, and fine chems. The simulated moving bed (SMB) process as a continuous chromatog. sepn. process is an interesting alternative to conventional batch chromatog., and gained more and more impact recently. In this paper, flavanone enantiomers were sepd. by simulated moving bed process. The best purities of the products obtained were 100% for the raffinate and 82% for the ext.

Abstract

Separation of flavanone enantiomers by simulated moving bed (SMB) process. Katsuyama, Hirokazu; Uemura, Yoshimitsu; Yoshida, Masahiro; Hatate, Yasuo. Grad. Sch. Appl. Chem. Eng., Kagoshima Univ., Japan. Kagoshima Daigaku Kogakubu Kenkyu Hokoku (2003), 45 79-85. Publisher: Kagoshima Daigaku Kogakubu, CODEN: KDKKBA ISSN: 0451-212X. Journal written in Japanese. CAN 140:43699 AN 2003:986115 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chalcononaringenin 2'-O-glucoside (Ch2'G) was found to be the major pigment mol. in the petals of carnations bearing yellow flowers. The concn. of this pigment varied from 5.5 to 100.0% (relative value with amts. in the line '7154-03' assumed to be 100%) in 31 carnation genotypes investigated. The transcription of both phenylalanine ammonia-lyase (PAL) and chalcone synthase (CHS) genes was active in the petals of both yellow carnation flowers and a cyanic control cultivar. The transcripts derived from the chalcone-flavanone isomerase (CHI) gene in the petals of yellow carnation flowers were below the level detectable by Northern blot anal., but could be detected by RT-PCR. This is possible to produce subtle amts. of CHI protein translated from suspicious amts. of the mRNA to catalyze chalcone, resulting in the variation of the concn. of Ch2'G. Other probable factors caused to the variation include the amt. of substrates supplying the flavonoid biosynthetic pathway, spontaneous isomerization flowing over the CHI step producing flavonol derivs., and chalcone 2'-glucosyltransferase (CHGT) activity.

Abstract

Variation in chalcononaringenin 2'-O-glucoside content in the petals of carnations (Dianthus caryophyllus) bearing yellow flowers. Yoshida, Hiroyuki; Itoh, Yoshio; Ozeki, Yoshihiro; Iwashina, Tsukasa; Yamaguchi, Masa-atsu. Applied Plant Research Center, Japan Tobacco, Inc., Oyama, Tochigi, Japan. Scientia Horticulturae (Amsterdam, Netherlands) (2004), 99(2), 175-186. Publisher: Elsevier Science B.V., CODEN: SHRTAH ISSN: 0304-4238. Journal written in English. CAN 140:403403 AN 2003:998914 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


On page 1197, the relative stereochem. of compd. 5 was incorrect; the correct structure is given. On pages 1200-1201, the correct trivial name for compd. 6 [7,2',6'-trimethoxy-6",6"-dimethylpyrano-(3',4':2",3")-chalcone] is 7-O-methylpraecansone B, and not 7-methoxypraecansone B as given.


flavanone

Tandem mass spectrometric methods were evaluated for the characterization of the interglycosidic linkage type and differentiation of four pairs of isomeric flavonoid O-diglycosides. Metastable ion spectra of the protonated rhoifolin and its isomer, isorhoifolin differ by the interglycosidic linkage type between the two monosaccharides. Different relative abundances of the Y0 (protonated aglycon) and

Abstract

Mass spectrometric methods for characterization and differentiation of isomeric O-diglycosyl flavonoids. Cuyckens, F.; Ma, Y. L.; Van den Heuvel, H.; Claeys, M. Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belg. Advances in Mass Spectrometry (2001), 15 891-892. Publisher: John Wiley & Sons Ltd., CODEN: AMSPAH ISSN: 0568-000X. Journal written in English. CAN 141:28767 AN 2003:974939 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The antiproliferative activity of several natural and synthetic flavonoids and some related compds. was evaluated in vitro against a cell line derived from a human cervical carcinoma (WISH cells). According to their activities, the most potent derivs. were 2'-nitroflavone (14), 2',6-dinitroflavone (15) and the Bu ester of caffeic acid (29). When these compds. were tested in the presence of recombinant human interferon-α2b (rhIFN-α2b), a cytokine exhibiting an antimitogenic action on WISH cells, an additive effect on cell growth inhibition was obsd. Time course studies of the antiproliferative action exerted by the active derivs. or the rhIFN-α2b suggested that these compds. induced cell death.

Abstract

Antiproliferative activity of various flavonoids and related compounds: additive effect of interferon-αg2b. Blank, Viviana C.; Poli, Cecilia; Marder, Mariel; Roguin, Leonor P. Facultad de Farmacia y Bioquimica, Instituto de Quimica y Fisicoquimica Biologicas, Buenos Aires, Argent. Bioorganic & Medicinal Chemistry Letters (2004), 14(1), 133-136. Publisher: Elsevier Science B.V., CODEN: BMCLE8 ISSN: 0960-894X. Journal written in English. CAN 140:246359 AN 2003:981464 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The GABI-Kat population of T-DNA mutagenized Arabidopsis thaliana lines with sequence-characterized insertion sites is used extensively for efficient progress in plant functional genomics. Here we provide details about the establishment of the material, demonstrate the population's functionality and discuss results from quality control studies. T-DNA insertion mutants of the accession Columbia (Col-0) were created by Agrobacterium tumefaciens-mediated transformation. To allow selection of transformed plants under greenhouse conditions, a sulfadiazine resistance marker was employed. DNA from leaves of T1 plants was extd. and used as a template for PCR-based amplification of DNA fragments spanning insertion site borders. After sequencing, the data were placed in a flanking sequence tag (FST) database describing which mutant allele was present in which line. Anal. of the distribution of T-DNA insertions revealed a clear bias towards intergenic regions. Insertion sites appeared more frequent in regions in front of the ATG and after STOP codons of predicted genes. Segregation anal. for sulfadiazine resistance showed that 62% of the transformants contain an insertion at only one genetic locus. In quality control studies with gene-specific primers in combination with T-DNA primers, 76% of insertions could be confirmed. Finally, the functionality of the GABI-Kat population was demonstrated by exemplary confirmation of several new transparent testa alleles, as well as a no. of other mutants, which were identified on the basis of the FST data.

Abstract (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The invention relates to optically active high-mol. compds. I and stationary-phase materials contg. the same, wherein Ar = arom. ring; R1, R2 = H or org. group; R3, R4 = substituent; n = ≥2 integer; X = (CH2)m, arom. group, vinyl group, heteroatom, or heteroatom-contg. group; and m = ≥0 integer, the compd. may have 2-4 R3s and/or 2-4 R4s which may be each the same or different from each other. The high-mol. compds. exhibit optical activity by virtue of their stacking helical structures wherein the arom. groups are distorted, thus being useful as optically active stationary phases for HPLC or polarized-light absorbers. Thus, 312.5 mg (-)-menthol was treated with 0.3 g potassium hydride to give menthoxy potassium, 2.02 mmol dibenzofulvene were polymd. in the presence of 2.0 mL 0.2M of the resulting menthoxy potassium at -78° for 24 h to give a polymer with Mn 1070 and polydispersity 1.47, which was used as a stationary phase for the sepn. of racemic compds., showing good efficiency.

Abstract WO 2003-JP5726 W 20030507JP 2002-132599 A 20020508Priority Application US 20050234267 A1 20051020 US 2004-513658 20041108

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, FI, RO, CY, TR, BG, CZ, EE, HU, SK

EP 1528070 B1 20071128EP 1528070 A1 20050504 EP 2003-728039 20030507CA 2485305 A1 20031211 CA 2003-2485305 20030507

RW: AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI, SK, TR

W: CA, JP, USWO 2003102039 A1 20031211 WO 2003-JP5726 20030507Patent No. Kind Date Application No. Date Patent Family Information

Optically active high-molecular compounds. Nakano, Tamaki. (Japan Science and Technology Corporation, Japan). PCT Int. Appl. (2003), 20 pp. CODEN: PIXXD2 WO 2003102039 A1 20031211 Designated States W: CA, JP, US. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR. Patent written in Japanese. Application: WO 2003-JP5726 20030507. Priority: JP 2002-132599 20020508. CAN 140:17462 AN 2003:972114 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Y1 (loss of 146 units) ions was also obsd. in the spectra of kaempferol-7-O-neohesperidoside and nicotiflorin. Another significant difference is that a weak ion (Y*) can only be seen in the spectra of nicotiflorin. The Y*/Y1 ratio is much smaller for rutin, a flavonoid 3-O-rutinoside, than for hesperidin, a flavonoid 7-O-rutinoside. The isomeric flavonoids, naringin and narirutin, contain flavanone but differ in the interglycosidic linkage type between rhamnose and glucose.


flavanone

Abstract

Foliar flavonoids of the most primitive group, sect. Distegocarpus within the genus Carpinus. Chang, Chin-Sung; Jeon, Jeong Ill. Department of Forest Resources and the Arboretum, Seoul National University, Suwon, S. Korea. Biochemical Systematics and Ecology (2004), 32(1), 35-44. Publisher: Elsevier Science B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 140:318002 AN 2003:939870 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Bladder cancer is the fourth and eighth most common cancer in men and women in the United States, resp. Survivin, a member of inhibitor of apoptosis protein (IAP) gene family, is deregulated in a wide range of malignancies, including carcinoma of the bladder urothelium. Recent advances have identified survivin as a novel intervention target to induce apoptosis in cancer cells by phytochems. or synthetic agents. Silibinin is a naturally occurring flavanone, isolated from milk thistle ext., and has been shown to possess cancer prevention/intervention potential against various cancers. In several animal and human studies, it is found to be safe and non-toxic. Human bladder transitional-cell papilloma RT4 cells were treated with silibinin and analyzed for survivin protein and mRNA levels by Western blotting and real-time RT-PCR, resp. Silibinin treatment of cells for 24 h at 100 μM dose resulted in .apprx.50% decrease in survivin protein level; however, treatment at 200 μM dose for 24 and 48 h showed a complete loss in survivin protein without any change in actin used as loading control. Employing RT-PCR anal. we also obsd. that silibinin causes a strong to complete decrease in survivin mRNA levels. In other studies, down-regulation of survivin by silibinin was assocd. with a very strong and prominent caspases-9 and -3 activation as well as PARP cleavage. Quant. apoptotic assay showed that silibinin decreased survivin levels and caspases-PARP cleavages, in accord with a strong apoptotic death and growth inhibition of RT4 cells. Together, these findings suggest that more studies are needed to investigate in vivo effect of silibinin on survivin expression and assocd. biol. effects in bladder cancer that could provide useful information for silibinin efficacy in the prevention/intervention of human bladder cancer.

Abstract

Silibinin down-regulates survivin protein and mRNA expression and causes caspases activation and apoptosis in human bladder transitional-cell papilloma RT4 cells. Tyagi, Anil K.; Agarwal, Chapla; Singh, Rana P.; Shroyer, Kenneth R.; Glode, L. Michael; Agarwal, Rajesh. School of Pharmacy, Department of Pharmaceutical Sciences, University of Colorado Health Sciences Center, Denver, CO, USA. Biochemical and Biophysical Research Communications (2003), 312(4), 1178-1184. Publisher: Elsevier Science, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 140:156969 AN 2003:940059 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


R

R

X

R43

Ar Ar

1 R2

n

I


flavanone

Priority Application JP 2003339399 A 20031202 JP 2002-155547 20020529 Patent No. Kind Date Application No. Date Patent Family Information

Genotyping of strawberry by PCR. Matsumoto, Akira; Kuniji, Miyuki; Fukino, Nobuko. (Nogyo Gijutsu Kenkyu Kiko, Japan). Jpn. Kokai Tokkyo Koho (2003), 14 pp. CODEN: JKXXAF JP 2003339399 A 20031202 Patent written in Japanese. Application: JP 2002-155547 20020529. Priority: . CAN 139:393524 AN 2003:936311 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A rapid screening assay for chems. inhibiting 11β-hydroxysteroid dehydrogenase (11β-HSD) type 1 or type 2 using lysates from stably transfected cells was developed. Here, we tested a series of environmental chems. for anti-11β-HSD activities. Inhibition of 11β-HSD2, which may cause cortisol-dependent activation of the mineralocorticoid receptor with sodium retention and hypertension, was obsd. for several compds., with diethylcarbamate being the most potent inhibitor (IC50 6.3 μM). Abietic acid inhibited both 11β-HSD1 (IC50 27 μM for redn. and 2.8 μM for oxidn.) and 11β-HSD2 (IC50 12 μM). Our results demonstrate for the first time that flavanone selectively inhibits 11β-HSD1 reductase activity: this enzyme being considered as essential for the local activation of glucocorticoids and representing a potential target for the therapeutic treatment of diabetes type 2. Flavanone and 2'-hydroxyflavanone efficiently inhibited reductive (IC50 18 and 10 μM) but not oxidative activity. We obsd. a reduced inhibitory effect of hydroxylated flavanone derivs. and of flavones contg. a double-bond between atom C2 and C3. Flavanone was specific for 11β-HSD1 and did not inhibit 11β-HSD2. Our results reveal that a variety of environmental compds. exert distinct inhibitory effects on 11β-HSD1 and 11β-HSD2, opening the possibility for selectively modulating local cortisone/cortisol availability in vivo.

Abstract

A rapid screening assay for inhibitors of 11β-hydroxysteroid dehydrogenases (11β-HSD): flavanone selectively inhibits 11β-HSD1 reductase activity. Schweizer, Roberto A. S.; Atanasov, Atanas G.; Frey, Brigitte M.; Odermatt, Alex. Division of Nephrology and Hypertension, Department of Clinical Research, University of Berne, Bern, Switz. Molecular and Cellular Endocrinology (2003), 212(1-2), 41-49. Publisher: Elsevier Science Ltd., CODEN: MCEND6 ISSN: 0303-7207. Journal written in English. CAN 140:246101 AN 2003:937804 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Foliar flavonoids in five taxa of the section Distegocarpus of Carpinus from China, Korea, and Japan were examd. Eleven compds., including monoglycosides of the flavonols myricetin, kaempferol and quercetin and the flavone luteolin along with hesperidin, were isolated and identified. The flavonoid profiles were relatively simple, but showed distinct differentiation among taxa. Flavonoid chem., morphol. characteristics, and geog. distribution patterns were in accord with the idea that section Distegocarpus appeared to have differentiated into two groups from the ancestor; one group (fangiana-type) consisting of C. fangiana and C. rankanensis, and the other (japonica-type) consisting of C. cordata and C. japonica. C. japonica was considered as the most primitive extant species of the section with respect to flavonoid compds. as well as morphol. characteristics. Within the fangiana-type, however, C. fangiana represented a more advanced species than C. rankanensis only with respect to morphol. The fact that the presence of a flavanone, which was a direct precursor to flavones and flavonols, was found in C. fangiana did not show correlation with the result of morphol. advancement within the fangiana group.


flavanone

Synthesis of a series of novel spiro[3,4-diaryl-4,5-dihydroisoxazole-5,31-flavan-41-one] I (R = H, Me, MeO, Cl, NO2; R1 = H, Cl) was accomplished in good yields by the regioselective 1,3-dipolar cycloaddn. reaction of nitrile oxide to 3-arylmethylideneflavan-4-ones.

Abstract

An easy access to spiroisoxazoline[5,31]flavan-41-one through 1,3-dipolar cycloaddition reaction of nitrile oxide to unusual dipolarophiles. Manikandan, Santhanaraman; Jayashankaran, Jayadevan; Raghunathan, Raghavachary. Department of Chemistry, University of North Carolina at Chapel Hill, NC, USA. Synthetic Communications (2003), 33(23), 4063-4069. Publisher: Marcel Dekker, Inc., CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 140:146042 AN 2003:929245 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The Raman spectrum of Artocarpus heterophyllus heartwood, which proved to be a rich source of flavonoids, exhibited two characteristic bands, at 1247cm-1 and 745cm-1. The bands also appeared in the Raman spectrum of the yellow-brown needles extd. from the heartwood with methanol. Based on the Raman measurements of flavones and related compds., it was predicted that the Raman band at 1247cm-1 may be attributed to flavonoid-type compds. No vibrational band corresponding to the characteristic Raman bands was obsd. by diffuse reflectance IR spectroscopy. Thus, it was suggested that observation of the characteristic bands is an advantage of Fourier transform-Raman spectroscopy for nondestructive anal. of wood.

Abstract

Characteristic Raman bands for Artocarpus heterophyllus heartwood. Yamauchi, Shigeru; Shibutani, Sakae; Doi, Shuichi. Institute of Wood Technology, Akita Prefectural University, Noshiro, Japan. Journal of Wood Science (2003), 49(5), 466-468. Publisher: Springer-Verlag Tokyo, CODEN: JWSCFG ISSN: 1435-0211. Journal written in English. CAN 141:107787 AN 2003:933838 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The DNA is extd. from calyx-contg. fruit and/or leaf of strawberry and analyzed by PCR for genotyping. The introns of the APX (ascorbic acid peroxidase), chalcone synthase (CHI), and flavanone-3-hydroxylase (F3H) genes were amplified by PCR for genotyping. Also used were strain-specific DNA markers such as APX insertion sequence.

Abstract JP 2002-155547 20020529


flavanone

Leachianone G (LG) 2''-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme, was identified in Sophora flavescens Ait. cultured cells. The enzyme transfers a dimethylallyl group to the 2'' position of another dimethylallyl group attached at position 8 of LG to form sophoraflavanone G, a branched monoterpenoid-conjugated flavanone characteristic to this plant. This membrane-bound dimethylallyltransferase required Mg2+ (optimum concn. was 10 mM) for the reaction and had an optimum pH of 8.8. It utilized dimethylallyl diphosphate as the sole prenyl donor, and the 2'-hydroxy function in LG was indispensable to the activity. The apparent Km values for dimethylallyl diphosphate and LG were 59 and 2.3 μM, resp. Subcellular localization of three enzymes that participated

Abstract

Characterization of leachianone G 2''-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme for the formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures. Zhao, Ping; Inoue, Kenichiro; Kouno, Isao; Yamamoto, Hirobumi. Medicinal Plant Garden, Course of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki, Japan. Plant Physiology (2003), 133(3), 1306-1313. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 140:107355 AN 2003:915173 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Microbial transformation of xanthohumol using the culture broth of Cunninghamella echinulata NRRL 3655 afforded (2S)-8-[4''-hydroxy-3''-methyl-(2''-Z)-butenyl]-4',7-dihydroxy-5-methoxyflavanone (5) and (2S)-8-[5''-hydroxy-3''-methyl-(2''-E)-butenyl]-4',7-dihydroxy-5-methoxyflavanone (6). Xanthohumol (1) and flavanone 6 as well as (E)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':4',3']-2',4-dihydroxy-6'-methoxychalcone (2), (2S)-2''-(2'''-hydroxyisopropyl)-dihydrofurano[2'',3'':7,8]-4'-hydroxy-5-methoxyflavanone (3) obtained with Pichia membranifaciens showed antimalarial activity against Plasmodium falciparum.

Abstract

Identification and biological activity of microbial metabolites of xanthohumol. Herath, Wimal; Ferreira, Daneel; Khan, Shabana Iqrar; Khan, Ikhlas Ahmad. National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS, USA. Chemical & Pharmaceutical Bulletin (2003), 51(11), 1237-1240. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:196011 AN 2003:917443 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

NO

RPh

O

R1 I


flavanone

In pome fruit trees, the growth retardant prohexadione-Ca induces the formation of 3-deoxycatechins, which correlates with an increased resistance against fire blight and also against some fungal diseases. The formation of 3-deoxycatechins is due to the channeling of intermediates unusual for pome fruits, which requires the presence of a flavanone 4-reductase (FNR) activity. Here, it is investigated, whether the crop plants strawberry, grapevine, cranberry, cherry, peach, plum, elder, and kiwi fruit react in the same way to prohexadione-Ca application. The presence of FNR activity is shown by enzymic investigations and the formation of a 3-deoxycatechin after prohexadione-Ca application in planta. Furthermore, by cloning of the corresponding cDNAs and studies with the

Abstract

Effect of prohexadione-Ca on various fruit crops: flavonoid composition and substrate specificity of their dihydroflavonol 4-reductases. Gosch, C.; Puhl, I.; Halbwirth, H.; Schlangen, K.; Roemmelt, S.; Andreotti, C.; Costa, G.; Fischer, T. C.; Treutter, D.; Stich, K.; Forkmann, G. Chair of Floriculture Crops and Horticultural Plant Breeding, Department of Plant Sciences, Technical University of Munich, Freising, Germany. European Journal of Horticultural Science (2003), 68(3), 144-151. Publisher: Verlag Eugen Ulmer GmbH & Co., CODEN: EJHSAS ISSN: 1611-4426. Journal written in English. CAN 140:176691 AN 2003:904275 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A large no. of natural, synthetic and environmental chems. are capable of disrupting the endocrine systems of exptl. animals, wildlife and humans. These so-called endocrine disrupting chems. (EDCs), some mimic the functions of the endogenous androgens, have become a concern to the public health. Androgens play an important role in many physiol. processes, including the development and maintenance of male sexual characteristics. A common mechanism for androgen to produce both normal and adverse effects is binding to the androgen receptor (AR). In this study, the authors used Comparative Mol. field Anal. (CoMFA), a 3D quant. structure-activity relationship (3D-QSAR) technique, to examine AR-ligand binding affinities. A CoMFA model with r2=0.902 and q2=0.571 was developed using a large training data set contg. 146 structurally diverse natural, synthetic, and environmental chems. with a 106-fold range of relative binding affinity (RBA). By comparing the binding characteristics derived from the CoMFA contour map with these obsd. in a human AR crystal structure, the authors found that the steric and electrostatic properties encoded in this training data set are necessary and sufficient to describe the RBA of AR ligands. Finally, the CoMFA model was challenged with an external test data set; the predicted results were close to the actual values with av. difference of 0.637 logRBA. This study demonstrates the utility of this CoMFA model for real-world use in predicting the AR binding affinities of structurally diverse chems. over a wide RBA range.

Abstract

Comparative molecular field analysis (CoMFA) model using a large diverse set of natural, synthetic and environmental chemicals for binding to the androgen receptor. Hong, H.; Fang, H.; Xie, Q.; Perkins, R.; Sheehan, D. M.; Tong, W. Northrop Grumman Information Technol., Jefferson, AR, USA. SAR and QSAR in Environmental Research (2003), 14(5-6), 373-388. Publisher: Taylor & Francis Ltd., CODEN: SQERED ISSN: 1062-936X. Journal written in English. CAN 140:265890 AN 2003:908996 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


in the formation of the lavandulyl group was also investigated by sucrose d. gradient centrifugation. Two prenyltransferases, naringenin 8-dimethylallyltransferase and LG 2''-dimethylallyltransferase, were localized in the plastids, whereas 8-dimethylallylnaringenin 2'-hydroxylase, which catalyzes the crucial step in the lavandulyl-group formation, was assocd. with the endoplasmic reticulum. These results suggest the close cooperation between the plastids and the endoplasmic reticulum in the formation of lavandulyl groups.


flavanone


Five new furoquinoline alkaloids, namely tecleabine (1), tecleoxine (2), isotecleoxine (3), methylnkolbisine (4) and chlorodesnkolbisine (5) were isolated from the aerial parts of Teclea nobilis, together with seven known furoquinoline derivs.; one acridone alkaloid, and one known flavanone. The structures of the alkaloids 1-5 were established by 1D and 2D NMR spectral data, including COSY, HMQC and HMBC expts., as well as HRMS.

Abstract

Furoquinoline alkaloids from Teclea nobilis. Al-Rehaily, Adnan J.; Ahmad, Mohammad S.; Muhammad, Ilias; Al-Thukair, Assad A.; Perzanowski, Herman P. College of Pharmacy, Department of Pharmacognosy, King Saud University, Riyadh, Saudi Arabia. Phytochemistry (Elsevier) (2003), 64(8), 1405-1411. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 140:142614 AN 2003:903485 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Rose (Rosa x bybrida), a popular and widely spread garden plant, is infected by numerous plant diseases, which are mainly caused by fungal and even by bacterial pathogens such as Erwinia amylovora, the causal agent of fire blight. Recently, prohexadione-Ca, a 2-oxoglutarate specific inhibitor originally developed as a growth retardant, was reported to influence the flavonoid compn. of apple and pear leaves and, thus, to increase resistance against fire blight and other diseases. It was supposed that this approach could also mediate resistance in roses. As the first step, the induction of the antimicrobial 3-deoxyflavonoid in rose leaves after prohexadione-Ca application was investigated in a time course expt. Due to the presence of disturbing phenolic compds. impeding the prepn. and testing of enzymes, enzyme prepn. procedures and assays had to be adapted and optimized for rose leaves. Std. enzyme assays are described for phenylalanine ammonia lyase (PAL), chalcone synthase/chalcone isomerase (CHS/CHI), flavanone 3-hydroxylase (FHT), dihydroflavonol 4-reductase (DFR) and flavanone 4-reductase (FNR). Cloning and heterologous expression showed that the DFR of rose exhibits FNR activity as well. Treatment of rose leaves with prohexadione-Ca led to the inhibition of FHT and to the formation of the 3-deoxyflavonoid luteoliflavan. Likewise, induction effects on PAL, CHS and DFR/FNR activity were also obsd. In general, it could be shown that rose leaves produce 3-deoxyflavonoids after prohexadione-Ca treatment and, therefore, this method can be considered as a potential protection strategy for roses that will be studied phytopathol. in a next step.

Abstract

Can prohexadione-Ca induce antimicrobial flavonoids in rose? Schlangen, K.; Gosch, C.; Roemmelt, S.; Knott, J.; Fischer, T. C.; Treutter, D.; Forkmann, G.; Stich, K.; Halbwirth, H. Institute of Technical BioScience, Technical University of Vienna, Vienna, Austria. European Journal of Horticultural Science (2003), 68(3), 137-143. Publisher: Verlag Eugen Ulmer GmbH & Co., CODEN: EJHSAS ISSN: 1611-4426. Journal written in English. CAN 140:178386 AN 2003:904273 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


heterologously expressed enzymes it is shown that the DFR enzymes of grapevine, cranberry and strawberry possess also FNR activity. Conclusively, all the crop plants studied have the potential to form 3-deoxyflavonoids. However, the changes in the flavonoid compn. obsd. after prohexadione-Ca treatment were not exactly the same in all species studied here. In kiwi fruit leaves, a strong accumulation of flavanones rather than the formation of large amts. of 3-deoxycatechins is obsd.


flavanone

WO 2003094910 A1 20031120 WO 2003-EP2445 20030310AU 2003218721 A1 20031111 AU 2003-218721 20030310

R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR


Use of 8-prenylflavanones for anti-angiogenesis therapy and for fibrinolytic therapy. Schleuning, Wolf-Dieter; Pepper, Michael. (Schering Aktiengesellschaft, Germany). Eur. Pat. Appl. (2003), 21 pp. CODEN: EPXXDW EP 1360959 A1 20031112 Designated States R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT, IE, SI, LT, LV, FI, RO, MK, CY, AL, TR. Patent written in English. Application: EP 2002-90170 20020510. Priority: . CAN 139:364765 AN 2003:891962 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two new herbertane sesquiterpenoids, (-)-herbertene-1,12-diol and (-)-γ-herbertenol, a new aromadendrane, 9-acetoxy-10-hydroxyaromadendrane, a new rosane diterpenoid, 5,15-rosadiene-3,11-dione and a new phytane, 2Z-phytene-1,15,20-triol, along with the known (-)-α-herbertenol have been isolated from the liverwort Tylimanthus renifolius. Several flavones and flavanones with an unsubstituted ring B were also identified. This is the first report of this class of flavonoids from the Hepaticae. All structures were elucidated by NMR spectroscopy.

Abstract

Secondary metabolites from the liverwort Tylimanthus renifolius. Feld, Hildegard; Zapp, Josef; Becker, Hans. Pharmakognosie und Analytische Phytochemie, FR 8.7, Universitat des Saarlandes, Saarbrucken, Germany. Phytochemistry (Elsevier) (2003), 64(8), 1335-1340. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 140:142604 AN 2003:903474 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Five prenylated flavonoids, 8-(1,1-dimethylallyl)genistein (1), 5,7,3',4'-tetrahydroxy-2',5'-di(3-methylbut-2-enyl)isoflavone (2), 5,7,3'-trihydroxy-2'-(3-methylbut-2-enyl)-4',5'-(3,3-dimethylpyrano)isoflavone (3), (2R)-5,2',4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4a) and (2S)-5, 2', 4'-trihydroxy-8,5'-di(3-methylbut-2-enyl)-6,7-(3,3-dimethylpyrano)flavanone (4b), were isolated from the roots of Moghania philippinensis. The structures of these compds. were detd. on the basis of spectroscopic and chem. means.

Abstract

Prenylated flavonoids from Moghania philippinensis. Ahn, Eun-Mi; Nakamura, Norio; Akao, Teruaki; Komatsu, Katsuko; Qui, Ming-Hua; Hattori, Massao. Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan. Phytochemistry (Elsevier) (2003), 64(8), 1389-1394. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 140:142611 AN 2003:903482 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Polymer-bound cellulose phenylcarbamate derivatives as chiral stationary phases for enantioselective HPLC. Ling, Frank; Brahmachary, Enugurthi; Xu, Mingcheng; Svec, Frantisek; Frechet, Jean M. J. Department of Chemistry, University of California, Berkeley, CA, USA. Journal of Separation Science (2003), 26(15-16), 1337-1346. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 140:174062 AN 2003:882197 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OHO

OH

Me Me

O

O

Me Me

HO

OH

OHR1 R2

R3

R4

I II

The present invention provides the use of 8-prenylflavanones such as I: wherein R1 = H, a OH group in position 2', 3' or 4'; a OMe group in position 2', 3' or 4' or a OEt group in position 3' or 4'; R2 = H, a OH group in position 3', 4', 5' or 6'; a OMe group in position 3' or 4' or a OEt group in position 5'; R3 = H, a OH group in position 4', 5' or 6' or a OMe group in position 4', 5' or 6'; R4 = H, OH; for the prepn. of a pharmaceutical compn. for the treatment or prevention of angiogenesis-related diseases and for the treatment or prevention of thrombotic disorders. Thus, (±)-8-prenylnaringenin (II) inhibits in vitro angiogenesis induced by bFGF, VEGF or a combination of bFGF and VEGF, in a dose-dependent manner. A quant. anal. revealed that II inhibited BME cell invasion with an IC50 of between 3-10μM, irresp. of the angiogenic stimulus.

Abstract WO 2003-EP2445 W 20030310EP 2002-90170 A 20020510Priority Application JP 2005526122 T 20050902 JP 2004-502996 20030310


EP 1503752 A1 20050209 EP 2003-711961 20030310

RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


flavanone

Some of the medicinal properties of lemons are due to the flavonoids they contain since they are involved in many biol. activities and have many health-related functions. The levels of the principal flavanones and flavone found in different cultivars of Citrus limon, are analyzed in an attempt to identify the most interesting as regards the content of such secondary compds. The results show that the immature fruits from cultivars Lisbon and Fino-49 are ideal for obtaining the flavanone hesperidin, while the mature fruits of

Abstract

Citrus limon: a source of flavonoids of pharmaceutical interest. Del Rio, J. A.; Fuster, M. D.; Gomez, P.; Porras, I.; Garcia-Lidon, A.; Ortuno, A. Facultad de Biologia, Departamento de Biologia Vegetal, Universidad de Murcia, Murcia, Spain. Food Chemistry (2003), Volume Date 2004, 84(3), 457-461. Publisher: Elsevier Science, CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 140:187071 AN 2003:877612 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


In higher plants, secondary metabolites are often converted to their glycoconjugates by glycosyltransferases (GTases). We cloned a cDNA encoding GTase (NtGT2) from tobacco (Nicotiana tabacum L.). The recombinant enzyme expressed in Escherichia coli (rNTGT2) showed glucosylation activity against several kinds of phenolic compds., particularly the 7-hydroxyl group of flavonoids and 3-hydroxycoumarin. The Km values of kaempferol and 3-hydroxycoumarin with rNTGT2 are 6.5 μM and 23.6 μM, resp. The deduced amino acid sequence of NTGT2 shows 60-70% identity to that of anthocyanin 5-O-glucosyltransferase (A5GT); rNTGT2 did not show activity against the anthocyanins tested. NtGT2 gene expression was induced by treating tobacco cells with plant hormones such as salicylic acid. We consider that NtGT2 gene might have evolved from the same ancestral gene as the A5GT genes to the stress-inducible GTases that react on several phenolic compds.

Abstract

Cloning and characterization of a glucosyltransferase that reacts on 7-hydroxyl group of flavonol and 3-hydroxyl group of coumarin from tobacco cells. Taguchi, Goro; Ubukata, Takahisa; Hayashida, Nobuaki; Yamamoto, Hirobumi; Okazaki, Mitsuo. Research Center for Human and Environmental Sciences, Division of Gene Research, Shinshu University, 3-15-1 Tokida, Ueda, Japan. Archives of Biochemistry and Biophysics (2003), 420(1), 95-102. Publisher: Elsevier Science, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN 140:89776 AN 2003:881361 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Novel chiral stationary phases (CSP) were prepd. by coating the internal surface of monodisperse macroporous poly(2-aminoethyl methacrylate-co-ethylene dimethacrylate) beads with dimethylphenylcarbamate derivs. of regenerated cellulose. The coating was achieved either by simple adsorption or by chem. bonding using a diisocyanate linker. Sepn. of enantiomers in normal-phase HPLC mode was used to evaluate the enantioselectivity of all CSPs. The influence of the properties of the polymer support such as pore size, pore vol., and content of the amine functionalities, reaction and sepn. conditions such as wt. ratio of modified cellulose selector to polymer beads, amt. of diisocyanate crosslinker, and the compn. of the mobile phase on chiral discrimination and chromatog. resoln. were also systematically studied. The CSPs prepd. by chem. anchoring were more stable and a wider range of solvents including dichloromethane could be used for the sepns. Compared to the coated-type CSPs, the chem. bonded stationary phases enabled the enantiosepns. of a larger no. of racemates and exhibited enantioselectivity fully comparable to their counterparts prepd. using porous silica as a support. However, the benefits of tailored macroporous polymer supports demonstrated earlier with brush-type CSPs did not enhance the performance of the chiral stationary phases prepd. from cellulose-based selectors.

Abstract


flavanone

Being acyanic: An unavoidable fate for many white flowers? Seitz, C.; Oswald, N.; Boerstling, D.; Forkmann, G.; Martens, S. Department fuer Pflanzenwissenschaften, Lehrstuhl fuer Zierpflanzenbau, TU Muenchen, Freising, Germany. Acta Horticulturae


From an Et acetate-sol. fraction of the exudate obtained from the stems of Angelica keiskei (Umbelliferae), 17 compds., viz. five chalcones (1-5), seven coumarins (6-12), three flavanones (13-15), one diacetylene (16), and one 5-alkylresorcinol (17), were isolated. These compds. were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor-promoters. With the exception of three compds. (10, 16, and 17), all other compds. tested showed potent inhibitory effects on EBV-EA induction (92-100% inhibition at 1×103 mol ratio/TPA). In addn., upon evaluation of these compds. for the inhibitory effects against activation of (±)-(E)-methyl-2-[(E)-hydroxy-imino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for antitumor-initiators, two chalcones (2 and 3) and six coumarins (6-11) exhibited potent inhibitory effects.

Abstract

Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects. Akihisa, Toshihiro; Tokuda, Harukuni; Ukiya, Motohiko; Iizuka, Masao; Schneider, Stefan; Ogasawara, Kazuya; Mukainaka, Teruo; Iwatsuki, Kenji; Suzuki, Takashi; Nishino, Hoyoku. College of Science and Technology, Nihon University, 1-8 Kanda Surugadai, Chiyoda-ku, Tokyo, Japan. Cancer Letters (Oxford, United Kingdom) (2003), 201(2), 133-137. Publisher: Elsevier, CODEN: CALEDQ ISSN: 0304-3835. Journal written in English. CAN 140:296986 AN 2003:866551 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chitin carbamate derivs. including 4-substituted and 3,5-disubstituted phenylcarbamates, 1-phenylethylcarbamates, and cycloalkylcarbamates were synthesized and coated on macroporous silica gel to evaluate their chiral recognition abilities as chiral stationary phases (CSPs) for HPLC. Among the derivs., the 3,5-dimethylphenyl, 4-chlorophenyl, and 4-trifluoromethylphenylcarbamates showed relatively high-chiral recognition abilities when a hexane-2-propanol mixt. was used as the eluent. The CSPs based on the chitin 3,5-dimethylphenyl and 3,5-dichlorophenylcarbamates could be stably used in the presence of chloroform and Et acetate as a component of the eluents, and a few racemates were more sufficiently resolved by the addn. of a small amt. of chloroform in the mobile phase. Some racemates were more efficiently resolved under the reversed phase condition.

Abstract

High-performance liquid chromatographic enantioseparation using chitin carbamate derivatives as chiral stationary phases. Yamamoto, Chiyo; Hayashi, Tomoko; Okamoto, Yoshio. Graduate School of Engineering, Department of Applied Chemistry, Nagoya University, Chikusa-ku, Nagoya, Japan. Journal of Chromatography, A (2003), 1021(1-2), 83-91. Publisher: Elsevier Science B.V., CODEN: JCRAEY ISSN: 0021-9673. Journal written in English. CAN 140:191761 AN 2003:869869 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


cultivar Fino-49 and the leaves of cultivar Eureka are the most interesting for obtaining the flavone diosmin and the flavanone eriocitrin.


flavanone

CA 2484080 A1 20031030 CA 2003-2484080 20030418US 20030229136 A1 20031211 US 2002-126407 20020418


W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW


Preparation of novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents. Zaveri, Nurulain; Chao, Wan-Ru. (SRI International, USA; Stanford Research Institute International). PCT Int. Appl. (2003), 72 pp. CODEN: PIXXD2 WO 2003089423 A2 20031030 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2003-US12658 20030418. Priority: US 2002-126407 20020418. CAN 139:350577 AN 2003:855920 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


For a range of white flowering ornamental species possessing favorable phenotypical and economical properties, there is an ardent desire of breeders to get them colored. Unfortunately, classical approaches often fail in this respect which has led to an increased interest in understanding the underlying reasons for this failure. Here, attention is focused on flavonoids as the main group of color-giving compds. in flowers. Flavonoid biosynthesis is a well-examd. pathway. In particular, it has been possible to demonstrate and characterize the activity of flavonoid enzymes resulting in the formation of anthocyanins, which are responsible for colors ranging from orange and red to lilac and blue. The lack of activity of one or more enzymes of this pathway leads to acyanic flowers. In white spatha of Zantedeschia aethiopica cv. 'Nili' and white petals of Osteospermum-Hybrid cv. 'Zimba' early enzymes of flavonoid biosynthesis chalcone synthase (CHS), chalcone isomerase (CHI) and flavanone 3-hydroxylase (FHT) were proven to be active, resulting in the formation of dihydrokaempferol (DHK). This compd. was shown to be 3'-hydroxylated to dihydroquercetin (DHQ) by flavonoid 3'-hydroxylase (F3'H) in Zantedeschia and to be 3'- and 5'-hydroxylated to DHQ and dihydromyrecetin (DHM) by flavonoid 3'5'-hydroxylase (F3'5'H) in Osteospermum. Whereas redn. of dihydroflavonols by DFR to leucoanthocyanidins did not occur in 'Zimba', it was clearly detected in 'Nili'. This suggests a lack of anthocyanidin synthase (ANS) activity in 'Nili'. ANS converts leucoanthocyanidins to resp. anthocyanidins. Particle gun bombardment of 'Nili' spatha with plasmids contg. Ans from M. incana led to red spots, thus supporting this hypothesis. On the other hand, 'Zimba' petals did not show any spotting under bombardment both with plasmids contg. Ans and plasmids contg. Dfr from Gerbera-Hydrids suggesting the regulatory blocking of a complete set of late enzymes.

Abstract

(2003), 612 83-88. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 140:178270 AN 2003:858632 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Novel compds. useful as chemotherapeutic, chemopreventive, and antiangiogenic agents are provided. The compds. are flavanoids, including flavanones, flavanols, and chalcones. The compds. I [R1 - R3 = OH, halo, SH, alkoxy, aryloxy, aralkoxy; R1R2 = cycle; R2R3 = cycle; α, β and γ = optional bonds, (providing that when α is absent, β is present, and when β is absent, α is present; when α is present, preferred R4 moieties are selected from O, S, NH and CH2, and when γ is absent, preferred R4 groups are selected from OH, SH, NH2 and CH3; when γ is present, the preferred R5 substituent is O, while when γ is absent, the preferred R5 substituent is OH);R6 - R9 = H, alkyl, alkenyl, aryl, aralkyl, alkoxy, aryloxy, aralkoxy (providing that R6 and R7, R7 and R8 or R8 and R9 = maybe linked to form a 5- or 6-membered ring and fused 5- and/or 6-membered rings, the rings being arom., alicyclic, heteroarom., heteroalicyclic with 0 - 4 non-hydrogen atoms and 0 - 3 heteroatoms); R10, R11 = H, OH, alkyl, alkoxy, halo]. Thus, SR 13179 (II) was prepd. from 2-acetyl-α-naphthol and 3,4,5-trimethoxybenzaldehyde in EtOH contg. piperidine and pyridine, followed by redn. with NaBH4 in THF/EtOH.. Pharmaceutical compns. are provided as well as are methods of synthesis and use. The antiangiogenic activity of SR 13179 (II) was tested vs. human vascular endothelial cells [IC50 = 1.41 mM vs. MCF-7 cells and IC50 = 3.01 mM vs. MDA-MB-231 cells].

Abstract WO 2003-US12658 W 20030418US 2002-126407 A 20020418Priority Application JP 2005533760 T 20051110 JP 2003-586144 20030418


EP 1495014 A2 20050112 EP 2003-724194 20030418AU 2003231069 A1 20031103 AU 2003-231069 20030418


flavanone

Synthesis and antimicrobial study of some new chloro-substituted 4-aroyl isoxazolines. Parhate, Vandana V.; Maurya, M. R.; Rajput, P. R.; Wagh, P. P.; Rai, M. K. Department of Chemistry, Vidya Bharti Mahavidyalaya, Amravati, India. Asian Journal of Chemistry (2003), 15(3 & 4), 1825-1827. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077.


Some new 4-aroyl substituted pyrazolines and pyrazoles were synthesized by condensation of Ph hydrazine hydrochloride with 3-aroyl flavanones in DMF contg. small amt. of piperidine. Also, 4-aroyl-substituted pyrazoles were synthesized by reaction with 4-aroyl-substituted pyrazolines with DMSO-I2-H2SO4 system or DMSO-I2 system. Structures of the compds. were characterized by IR spectra, PMR spectra and chem. properties.

Abstract

Synthesis and characterization of 4-aroyl substituted pyrazolines and pyrazoles. Bodkhe, Pravin S.; Patil, K. N.; Doshi, A. G. Department of Chemistry, Vidyabharti Mahavidyalaya, Amravati, India. Asian Journal of Chemistry (2003), 15(3 & 4), 1853-1855. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in English. CAN 140:181369 AN 2003:849644 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH

OMe

OMe

OMe

R4

R5R6R7

R8R9

R1

R2

R3

R10

R11

α

β

γ

I

II


flavanone

Answer 873:

Three new diterpenoids, excoecarins V1-V3 and a new flavanone glycoside were isolated from the fresh stem of Excoecaria agallocha L. Their structures were elucidated as: 2α,3α,18-trihydroxy-3β,20-epoxybeyer-15-ene, ent-2,3-secokaur-16-en-2,3-dioic acid, ent-3,4-seco-16α-hydroxyatis-4(19)-en-3-oic acid, and 3,5,7,3',5'-pentahydroxy-2R,3R-flavanonol 3-O-α-L-rhamnopyranoside on the basis of spectroscopic data, chem. evidence, and/or X-ray anal.

Abstract

Three diterpenoids (excoecarins V1-V3) and a flavanone glycoside from the fresh stem of Excoecaria agallocha. Konishi, Tenji; Yamazoe, Kiyonori; Kanzato, Masahiro; Konoshima, Takao; Fujiwara, Yasuhiro. Kyoto Pharmaceutical University, Kyoto, Japan. Chemical & Pharmaceutical Bulletin (2003), 51(10), 1142-1146. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:317993 AN 2003:835784 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new prenylated flavanone, licoleafol, and a new prenylated dihydrostilbene, uralstilbene, together with four known compds., 8-dimethylallyleriodictyol, sophoraflavanone B, gancaonin R, and 6-dimethylallyleriodictyol, were isolated from the leaves of Glycyrrhiza uralensis collected in Kazakhstan. HPLC anal. of the leaves of Glycyrrhiza plants collected in Kazakhstan showed that both G. uralensis-specific and Glycyrrhiza glabra-specific compds. were detected in the leaves of the morphol. intermediate-type plants, suggesting that the intermediate-type plant is a hybrid of G. glabra and G. uralensis. In addn., HPLC profiles of leaf exts. from offspring of intermediate-type plants were divided into the three types:the G. uralensis type, G. glabra type, and the intermediate type. From these results, it appears likely that the intermediate-type plant back-crosses with G. glabra and G. uralensis to generate a G. glabra-type plant and a G. uralensis-type plant, resp.

Abstract

Field survey of Glycyrrhiza plants in central Asia (2). Characterization of phenolics and their variation in the leaves of Glycyrrhiza plants collected in Kazakhstan. Hayashi, Hiroaki; Zhang, Shui-Li; Nakaizumi, Tomoko; Shimura, Kumiko; Yamaguchi, Misako; Inoue, Kenichiro; Sarsenbaev, Kanat; Ito, Michiho; Honda, Gisho. Gifu Pharmaceutical University, Gifu, Japan. Chemical & Pharmaceutical Bulletin (2003), 51(10), 1147-1152. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:317994 AN 2003:835785 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Some new chloro-substituted 4-aroyl isoxalines were synthesized by the interaction of chloro-substituted 3-aroyl flavanones with NH2OH⋅HCl in DMSO contg. a few drops of piperidine. The structural assignments of these compds. are based on their elemental anal., chem. properties and spectral data. The newly synthesized chloro-substituted 4-aroyl isoxazolines were evaluated for their antimicrobial activity against E. coli, S. aureus, P. aeruginosa, P. vulgaris by disk diffusion method. The antibacterial results obtained are very encouraging.

Abstract Journal written in English. CAN 140:181351 AN 2003:849633 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Diterpenes and sesquiterpenes from the bark of Taxus yunnanensis. Nguyen, Nhan Trung; Banskota, Arjun H.; Tezuka, Bibliographic Information Answer 875:

Citrus fruits of different species and cultivars, ("Red blush" grapefruit, "Palazzelli" mandarin-type fruit, "Minneola" tangelo and "Salustiana" and "Shamouti" orange) were minimally processed as segments or juices and cold-stored for up to 12 or 15 days, resp. The flavanone glycosides, ascorbic acid (AA) content and antioxidant capacity were detd. during storage. Minimal processing had almost no effect on the main chem. constituents, but ascorbic acid decreased significantly in "Minneola" and "Salustiana" segments, with values ranging from 1.63 to 5.10 mg/g of dry matter, although only in the last samples taken. One of 3 juices (Salustiana) also showed a decrease in AA content. The segments and juices showed different behavior during storage with regard to the flavonoid content, which ranged from 0.77 mg to 8.32 mg/g dry matter in Palazzelli mandarin and Red blush grapefruit, resp. A significant increase in total flavonoids (mainly hesperidin) was found in the segments, while the juices showed a diminution in flavonoid content. Antioxidant capacity increased significantly in "Red blush" grapefruit juices and "Salustiana" orange segments, decreased in "Salustiana" juices and "Minneola" tangelo segments and remained const. in the other samples. The antioxidant capacity, moreover, was clearly correlated (r=0.968 and r=0.889 in segments and juices, resp.) with the ascorbic acid content rather than with the presence of flavanone glycosides.

Abstract

Changes of flavonoids, vitamin C and antioxidant capacity in minimally processed citrus segments and juices during storage. Del Caro, Alessandra; Piga, Antonio; Vacca, Vincenzo; Agabbio, Mario. Dipartimento di Scienze Ambientali Agrarie e Biotecnologie Agro-Alimentari, Universita degli Studi, Sassari, Italy. Food Chemistry (2003), Volume Date 2004, 84(1), 99-105. Publisher: Elsevier Science, CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 140:127375 AN 2003:820808 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The antioxidant activities of naturally occurring plant compds. were measured in a lipid peroxidn. system consisting of Et arachidonate and Fenton's reagent. Inhibitory effects of 24 plant-derived flavonoids and 5 phenolic acids on malonaldehyde (MA) formation from Et arachidonate were examd. using gas chromatog. (GC) with a nitrogen-phosphorus detector (NPD). Luteolin, which showed the strongest antioxidant activity, inhibited MA formation by 94% and 97% at the levels of 0.5 and 1.0 mM, resp. The antioxidant activities of the flavones and flavonols decreased in the following order: luteolin > rhamnetin > fisetin > kaempferol > morin > quercetin. Among the flavanones tested, hesperitin, taxifolin, and naringenin exhibited appreciable antioxidant activities (61-84%) at the 1.0 mM level. The inhibitory effect of epigallocatechin gallate (82.5% at the 1.0 mM level) was the strongest among the flavan-3-ols tested. Ferulic acid had the most potent antioxidant activity (74.6% at the 1.0 mM level) of the phenolic acids tested.

Abstract

Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate. Lee, Kwang-Geun; Shibamoto, Takayuki; Takeoka, Gary R.; Lee, Sung-Eun; Kim, Jeong-Han; Park, Byeoung-Soo. Department of Food Science and Technology, Dongguk University, Seoul, S. Korea. Journal of Agricultural and Food Chemistry (2003), 51(24), 7203-7207. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 140:27006 AN 2003:829822 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

The treatment of grape berries (Vitis vinifera L. cv. Cabernet Sauvignon) with the ethylene-releasing compd., 2-chloroethylphosphonic acid (2-CEPA), at veraison is a method known to enhance grape skin color. We obsd. that it produced a 6-fold increase, up to 30 pmol g-1 FW, of the cluster internal ethylene compared to untreated controls within the 24 h following treatment. This ethylene upsurge was assocd. with increased levels of chalcone synthase (CHS) and flavanone 3-hydroxylase (F3H) transcripts, which persisted over the following 20 days. Transcript levels of leucoanthocyanidin dioxygenase (LDOX) and UDP glucose-flavonoid 3-O-glucosyl transferase (UFGT) were similarly enhanced by 2-CEPA, although to a lesser extent. The effect on UFGT was confirmed at the protein level by an immunoblot anal. The transcript accumulation of dihydroflavonol 4-reductase (DFR) was unaffected by 2-CEPA treatment. Examn. of the levels of CHS, F3H and UFGT mRNAs in berries during bunch exposure to ethylene, revealed elevated levels of each transcript

Abstract

Exogenous ethylene stimulates the long-term expression of genes related to anthocyanin biosynthesis in grape berries. El-Kereamy, Ashraf; Chervin, Christian; Roustan, Jean-Paul; Cheynier, Veronique; Souquet, Jean-Marc; Moutounet, Michel; Raynal, Jose; Ford, Christopher; Latche, Alain; Pech, Jean-Claude; Bouzayen, Mondher. UMR 990, Genomique et Biotechnologie des Fruits, INRA-INP/ENSA Toulouse, Castanet, Fr. Physiologia Plantarum (2003), 119(2), 175-182. Publisher: Blackwell Publishing Ltd., CODEN: PHPLAI ISSN: 0031-9317. Journal written in English. CAN 140:108179 AN 2003:788233 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Phytochem. anal. of the root bark of Bauhinia variegata Linn yielded a new flavanone, (2S)-5,7-dimethoxy-3',4'-methylenedioxyflavanone (1) and a new dihydrodibenzoxepin, 5,6-dihydro-1,7-dihydroxy-3,4-dimethoxy-2-methyldibenz [b,f]oxepin (2) together with three known flavonoids (3-5). The structures of the new compds. were detd. on the basis of spectral studies.

Abstract

A flavanone and a dihydrodibenzoxepin from Bauhinia variegata. Reddy, Mopuru V. B.; Reddy, Muntha K.; Gunasekar, Duvvuru; Caux, Cristelle; Bodo, Bernard. Department of Chemistry, Natural Products Division, Sri Venkateswara University, Tirupati, India. Phytochemistry (Elsevier) (2003), 64(4), 879-882. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 140:56467 AN 2003:803911 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Two taxane-type diterpenes, 10β-acetoxy-2α,5α,7β,9α-tetrahydroxytaxa-4(20),11-dien-13-one and 2α-acetoxy-9α-benzoyloxy-5α,7β,10β,15-tetrahydroxy-11(15 1)- abeotaxa-4(20),11-dien-13-one, and two new drimane-type sesquiterpenes, 1β-acetoxy-7-drimen-11α-ol-12,11-lactone and 1β-acetoxy-11,12-epoxy-6-drimen-8α,11α-diol, were isolated from the bark of Taxus yunnanensis together with 35 known taxane-type diterpenes, a known drimane-type sesquiterpene and a known flavanone.

Abstract

Yasuhiro; Nobukawa, Takahiro; Kadota, Shigetoshi. Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan. Phytochemistry (Elsevier) (2003), 64(6), 1141-1147. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 140:56477 AN 2003:803949 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 880:

Four prenylated flavanones were isolated from the methanol ext. of the flowers of Azadirachta indica (neem tree) as potent antimutagens against Trp-P-1 (3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole) in the Salmonella typhimurium TA98 assay by activity-guided fractionation. Spectroscopic properties revealed that these compds. were 5,7,4'-trihydroxy-8-prenylflavanone (I), 5,4'-dihydroxy-7-methoxy-8-prenylflavanone (II), 5,7,4'-trihydroxy-3',8-diprenylflavanone (III), and 5,7,4'-trihydroxy-3',5'-diprenylflavanone (IV). All isolated compds. were found for the first time in this plant. The antimutagenic IC50 values of compds. I-IV were 2.7 ± 0.1, 3.7 ± 0.1, 11.1 ± 0.1, and 18.6 ± 0.1 μM in the preincubation mixt., resp. These compds. also similarly inhibited the mutagenicity of Trp-P-2 (3-amino-1-methyl-5H-pyrido[4,3-b]indole) and PhIP (2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine). Compds. I-IV strongly inhibited ethoxyresorufin O-dealkylation activity of cytochrome P 450 1A isoforms, which catalyze N-hydroxylation of heterocyclic amines. However, compds. I-IV did not show significant inhibition against the direct-acting mutagen NaN3. Thus, the antimutagenic effect of compds. I-IV would be mainly based on the inhibition of the enzymic activation of heterocyclic amines.

Abstract

Prenylated flavanones isolated from flowers of Azadirachta indica (the neem tree) as antimutagenic constituents against heterocyclic amines. Nakahara, Kazuhiko; Roy, Molay Kumar; Ono, Hiroshi; Maeda, Ikuko; Ohnishi-Kameyama, Mayumi; Yoshida, Mitsuru; Trakoontivakorn, Gassinee. Japan International Research Center for Agricultural Sciences (JIRCAS), Tsukuba, Ibaraki, Japan. Journal of Agricultural and Food Chemistry (2003), 51(22), 6456-6460. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 139:377970 AN 2003:761583 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Naringin is the chief flavanone glycoside of grapefruit (Citrus paradisi). It is responsible for part of the bitter taste of the fruit and can cause the inhibition of some cytochrome P450s. The direct sepn. of (2R)- and (2S)-naringin in the albedo of grapefruits was obtained in normal phase HPLC mode using Chiralcel OD as chiral stationary phase and n-hexane/ethanol with 0.1% of TFA as mobile phase. Chiralpak AD was almost ineffective in the sepn. This procedure was used to evaluate the stereochem. at C-2 during maturation of the grapefruit. The CD curves of (2R)- and (2S)-naringin isolated by semipreparative chiral HPLC were detd. and the elution order of the chromatog. peaks was related to the abs. C-2 configuration. Partial resoln. of the C-2 diastereomers of narirutin was obtained on Chiralpak AD.

Abstract

Chiral HPLC separation and CD spectra of the C-2 diastereomers of naringin in grapefruit during maturation. Caccamese, Salvatore; Manna, Luigi; Scivoli, Giovanna. Dipartimento di Scienze Chimiche, Universita di Catania, Catania, Italy. Chirality (2003), 15(8), 661-667. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN 140:92770 AN 2003:781511 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


within the first 6 h of treatment when compared to nonethylene-treated controls. HPLC analyses of berry skin exts. showed that levels of each of the anthocyanins analyzed (delphinidin, cyanidin, petunidin, peonidin and malvidin) increased over the 10 days following the ethylene burst, and decreased thereafter. However, anthocyanin levels at harvest were still higher in ethylene treated grapes than in controls. This data is the first evidence that ethylene triggers gene expression related to anthocyanin synthesis in grapes, and in addn., our results also confirm the existence of other regulatory modes in the anthocyanin biosynthetic pathway.


flavanone

A novel biflavonoid named licobichalcone (I) was isolated from the roots of Glycyrrhiza uralensis cultivated in China, along with twelve known compds., including five chalcones, two isoflavones, two flavanones, two flavones and one pterocarpan. The structures were elucidated on the basis of chem. and spectroscopic evidence.

Abstract

A novel biflavonoid from roots of Glycyrrhiza uralensis cultivated in China. Bai, Hong; Li, Wei; Koike, Kazuo; Dou, Deqiang; Pei, Yuping; Chen, Yingjie; Nikaido, Tamotsu. School of Chinese Traditional Medicine, Shenyang Pharmaceutical University, Shenyang, Peop. Rep. China. Chemical & Pharmaceutical Bulletin (2003), 51(9), 1095-1097. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:56448 AN 2003:745724 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


There is considerable interest in the biol. properties of flavonoids in terms of their antioxidant and cytoprotective actions. The interaction of the flavanone hesperetin with human skin fibroblasts (FEK4) has revealed the potential for metab. to hesperetin glucuronide and its subsequent extrusion. As a consequence of this observation, the effectiveness of hesperetin glucuronides, in comparison with that of the aglycon form, in protecting against UV-A radiation has been investigated. The results indicate that hesperetin glucuronides, but not hesperetin, protect against UV-A-induced necrotic cell death.

Abstract

Hesperetin glucuronide, a photoprotective agent arising from flavonoid metabolism in human skin fibroblasts. Proteggente, Anna R.; Basu-Modak, Sharmila; Kuhnle, Gunter; Gordon, Matthew J.; Youdim, Kuresh; Tyrrell, Rex; Rice-Evans, Catherine A. Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, King's College London, London, UK. Photochemistry and Photobiology (2003), 78(3), 256-261. Publisher: American Society for Photobiology, CODEN: PHCBAP ISSN: 0031-8655. Journal written in English. CAN 140:249272 AN 2003:749311 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Study of 202 Natural, Synthetic, and Environmental Chemicals for Binding to the Androgen Receptor. Fang, Hong; Tong, Weida; Branham, William S.; Moland, Carrie L.; Dial, Stacy L.; Hong, Huixiao; Xie, Qian; Perkins, Roger; Owens, William; Sheehan, Daniel M. Northrop Grumman Information Technology, Jefferson, AR, USA. Chemical Research in Toxicology (2003), 16(10),


Studies on the chem. constituents of the flowers of Azadirachta indica have led to the isolation of 2 new flavanones, flowerine (5-hydroxy-7,4'-dimethoxy-8-(3-methylbut-2-enyl)flavan-4-one), and flowerone (5,7,8,4'-tetrahydroxy-3'-(3-methylbut-3-enyl)flavan-4-one), and 2 new triterpenoids, O-methylazadironolide (7α-(acetoxy)-23ξ-methoxy-21,23-epoxy-24,25,26,27-tetranorapotirucalla-1,14,20(22)-trien-3,21-dione), and diepoxyazadirol ((20S,23S,24R)-7-α-(acetoxy)-25-hydroxy-21,24:23,24-diepoxyapotirucalla-1,14-dien-3-one), along with the known triterpenoid trichilenone acetate (7α-(acetoxy)-14,15:21,23-diepoxy-24,25,26,27-tetranorapotirucalla-1,20,22-trien-3-one), 2 known flavanones, nimbaflavone (5,7-dihydroxy-4'-methoxy-8,3'-bis(3-methylbut-2-enyl)-flavan-4-one) and 3'-prenylnaringenin (5,7,4'-trihydroxy-3'-(3-methylbut-2-enyl) flavan-4-one), and 4-(2-hydroxyethyl)phenol. Their structures were elucidated through spectral studies, including 2D-NMR expts., and chem. transformation. Compds. 5, 7 and 8 are heretofore unreported from any part of tree, while 6 was isolated earlier from leaves.

Abstract

Chemical constituents of the flowers of Azadirachta indica. Siddiqui, Bina S.; Ali, Syed Tariq; Rasheed, Munawwer; Kardar, Muhammad Nadeem. H.E.J. Research Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi, Karachi, Pak. Helvetica Chimica Acta (2003), 86(8), 2787-2796. Publisher: Verlag Helvetica Chimica Acta, CODEN: HCACAV ISSN: 0018-019X. Journal written in English. CAN 140:73989 AN 2003:740995 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OH

OH

OMe

CO

CO

OMe

OH

OH

OH

HO

I


flavanone

Cuticular waxes and flavonol aglycons of mistletoes. Haas, Klaus; Bauer, Markus; Wollenweber, Eckhard. Universitaet Bibliographic Information Answer 885:

Prenylated 2'-hydroxychalcones and flavanones from the inflorescences of the female hop plant (Humulus lupulus) were shown to inhibit peroxynitrite-mediated oxidn. of low-d. lipoproteins (LDL) at low micromolar concns. LDL oxidn. was induced by the peroxynitrite generator, 3-morpholinosydnonimine (SIN-1), and measured by the formation of conjugated dienes and thiobarbituric reactive substances. Human intake of prenylated chalcones and flavanones is mainly through beer, which contains up to 4 mg/L of these polyphenols. The two main oxidn. products obtained by SIN-1 and peroxynitrite treatment of xanthohumol (XN), the principal prenylflavonoid of hops, were the aurone, auroxanthohumol (AUXN), and an endoperoxy deriv. of XN, named endoperoxyxanthohumol (EPOX). In addn., the reaction produced smaller amts. of the nitro and nitroso derivs. of XN and EPOX. The formation of these nitrated products was enhanced in the presence of sodium bicarbonate (25 mM). SIN-1-induced formation of AUXN is considered to be a superoxide-mediated reaction, while the structure of EPOX points to a two electron oxidn. reaction involving a Michael type addn. with peroxynitrite as the nucleophile, followed by cyclization yielding a (1,2)-dioxepin-5-one ring structure. The flavanone isomer of XN, isoxanthohumol (IsoXN), unexpectedly showed a slight prooxidant effect instead of an inhibitory effect on LDL oxidn. Except for the formation of minor nitrated products, IsoXN remained largely unmodified upon treatment with SIN-1/peroxynitrite. Taken together, our results suggest that the α,β-unsatd. keto functionality of chalcones is most reactive toward superoxide and peroxynitrite anions.

Abstract

Inhibition of Peroxynitrite-Mediated LDL Oxidation by Prenylated Flavonoids: The α,β-Unsaturated Keto Functionality of 2'-Hydroxychalcones as a Novel Antioxidant Pharmacophore. Stevens, Jan F.; Miranda, Cristobal L.; Frei, Balz; Buhler, Donald R. Department of Chemistry, Oregon State University, Corvallis, OR, USA. Chemical Research in Toxicology (2003), 16(10), 1277-1286. Publisher: American Chemical Society, CODEN: CRTOEC ISSN: 0893-228X. Journal written in English. CAN 139:286054 AN 2003:726787 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A no. of environmental and industrial chems. are reported to possess androgenic or antiandrogenic activities. These androgenic endocrine disrupting chems. may disrupt the endocrine system of humans and wildlife by mimicking or antagonizing the functions of natural hormones. The present study developed a low cost recombinant androgen receptor (AR) competitive binding assay that uses no animals. We validated the assay by comparing the protocols and results from other similar assays, such as the binding assay using prostate cytosol. We tested 202 natural, synthetic, and environmental chems. that encompass a broad range of structural classes, including steroids, diethylstilbestrol and related chems., antiestrogens, flutamide derivs., bisphenol A derivs., alkylphenols, parabens, alkyloxyphenols, phthalates, siloxanes, phytoestrogens, DDTs, PCBs, pesticides, organophosphate insecticides, and other chems. Some of these chems. are environmentally persistent and/or com. important, but their AR binding affinities have not been previously reported. To the best of our knowledge, these results represent the largest and most diverse data set publicly available for chem. binding to the AR. Through a careful structure-activity relationship (SAR) examn. of the data set in conjunction with knowledge of the recently reported ligand-AR crystal structures, we are able to define the general structural requirements for chem. binding to AR. Hydrophobic interactions are important for AR binding. The interaction between ligand and AR at the 3- and 17-positions of testosterone and R1881 found in other chem. classes are discussed in depth. The SAR studies of ligand binding characteristics for AR are compared to our previously reported results for estrogen receptor binding.

Abstract

1338-1358. Publisher: American Chemical Society, CODEN: CRTOEC ISSN: 0893-228X. Journal written in English. CAN 139:360170 AN 2003:739052 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Inhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage cell line. Sakata, Keiko; Hirose, Yoshinobu; Qiao, Zheng; Tanaka, Takuji; Mori, Hideki. Department of Tumor Pathology, School


OH

O

O

O

II III

The comparative photostability of curcumin, and two non-phenolic curcuminoids: 1,7-diphenyl-1,6-heptadiene-3,5-dione (unsubstituted curcumin) (I) and dimethylcurcumin in non-degassed dil. solns. (≈3-5 × 10-5 mol l-1) has been established by UV-visible absorption spectroscopy; disappearance quantum yields were measured. The similar behavior of the three studied curcuminoids is indicative of only a moderate role of phenol groups in the photodegrdn. process. Structural anal. of the photodegrdn. products of compd. I in more concd. soln. (≈3.6 × 10-3 mol l-1) shows formation of benzaldehyde, cinnamaldehyde, 2'-hydroxy-5',6'-benzochalcone (II), flavanone III and some other unidentified photoproducts. Flavanone III is formed by irradn. of chalcone II. It represents a unique example of photochem. conversion of a diarylheptanoid mol. into a flavonoid, another very important class of natural products.

Abstract

Studies on the photochemistry of 1,7-diphenyl-1,6-heptadiene-3,5-dione, a non-phenolic curcuminoid model. Sundaryono, Agus; Nourmamode, Aziz; Gardrat, Christian; Grelier, Stephane; Bravic, Georges; Chasseau, Daniel; Castellan, Alain. Laboratoire de Chimie des Substances Vegetales, UPRES EA-494, Universite Bordeaux, Fr. Photochemical & Photobiological Sciences (2003), 2(9), 914-920. Publisher: Royal Society of Chemistry, CODEN: PPSHCB ISSN: 1474-905X. Journal written in English. CAN 140:76922 AN 2003:709486 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Cuticular waxes of Viscum album subspecies and of V. cruciatum have been examd. for their micromorphol. and chem. compn. Wax crystalloids occur preferably as irregular platelets and rodlets, while deviant structures are found in small areas. Among the triterpenoids forming the wax layer, oleanolic acid is prevailing with some 80%. The quant. compn. of the long-chain aliphatics, which comprise several classes, is rather variable. Flavonoid aglycons, occurring as very minor components of the cuticular waxes, comprise the flavonols kaempferol and quercetin and a series of their Me derivs., in some taxa also the flavanone naringenin. Neither the crystalloid structures nor the chem. compn. of the wax allow to discriminate the 2 species, or male and female plants, or plants grown on conifers or on dicotyledoneous hosts.

Abstract

Hohenheim, Institut fuer Botanik 210, Stuttgart, Germany. Zeitschrift fuer Naturforschung, C: Journal of Biosciences (2003), 58(7/8), 464-470. Publisher: Verlag der Zeitschrift fuer Naturforschung, CODEN: ZNCBDA ISSN: 0939-5075. Journal written in English. CAN 140:38792 AN 2003:716927 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

An anal. based upon structure-activity relationships (SAR) of the COX-2-inhibiting properties of flavonoids, a group of potential cancer chemopreventive agents, reveals that there is a dual structural basis for these activities. Each of these structural determinants (pharmacophores) alone is sufficient for activity. One of the pharmacophores is a 2D 6.9 .ANG. distance descriptor that spans the A and C rings and includes the 4-oxo and 7-hydroxyl moieties. The potency assocd. with that pharmacophore is detd. by a series of structural modulators that can increase, decrease, or even abolish the COX-2-inhibiting potential assocd. with that pharmacophore. The

Abstract

SAR: flavonoids and COX-2 inhibition. Rosenkranz, Herbert S.; Thampatty, Bhavani P. Department of Biomedical Sciences, Florida Atlantic University, Boca Raton, FL, USA. Oncology Research (2003), Volume Date 2002, 13(12), 529-535. Publisher: Cognizant Communication Corp., CODEN: ONREE8 ISSN: 0965-0407. Journal written in English. CAN 140:246066 AN 2003:690440 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The varied biol. activity of flavanones mainly depends on their phys. and chem. properties. In order to obtain information on the acid-base behavior of flavanones of chem. and biol. interest the isomerization of 4'-methoxy-flavanone was studied and the formation const. of its enolate was detd. by UV spectrometry. The kinetic expts. were performed in aq. medium at 25±0.1 °C, keeping the ionic strength (0.07, KCl) and pH (10.8) const. The obtained results were interpreted by a four-step mechanism, which considered the existence of flavanone enolate as a key intermediate. Some stereochem. and mechanistic aspects of the reaction were explained by means of reactivity indexes and thermodn. magnitudes calcd. by ab initio methods in ethanol and water, which support the proposed mechanism. It is concluded that the kinetic methodol. here proposed to study the enolization properties of flavanones seems to be quite convenient to overcome the marked intrinsic instability of these substances in alk. media.

Abstract

Isomerization of 4'-methoxy-flavanone in alkaline medium. Determination of the enolate formation constant. Andujar, S. A.; Filippa, M. A.; Ferretti, F. H.; Blanco, S. E. Facultad de Quimica, Bioquimica y Farmacia, Area de Quimica-Fisica, Universidad Nacional de San Luis, San Luis, Argent. THEOCHEM (2003), 636 157-166. Publisher: Elsevier Science B.V., CODEN: THEODJ ISSN: 0166-1280. Journal written in English. CAN 140:41703 AN 2003:705925 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Previous data have shown that a citrus flavanone, hesperidin possesses chemopreventive efficacies. The authors designed to investigate the inhibitory effect of hesperidin on lipopolysaccharide (LPS)-induced over-expression of cyclooxygenase-2 (COX-2), inducible nitric oxide synthase (iNOS) proteins, over-prodn. of prostaglandin E2 (PGE2) and nitric oxide (NO) using mouse macrophage cells. Treatment with hesperidin suppressed prodn. of PGE2, nitrogen dioxide (NO2), and expression of iNOS protein. In the case of COX-2, hesperidin did not affect the protein level. The authors' data indicate hesperidin as a COX-2 and iNOS inhibitor, which might be related to the anti-inflammatory and anti-tumorigenic efficacies.

Abstract

of Medicine, Gifu University, Gifu, Japan. Cancer Letters (Oxford, United Kingdom) (2003), 199(2), 139-145. Publisher: Elsevier Science Ltd., CODEN: CALEDQ ISSN: 0304-3835. Journal written in English. CAN 140:156879 AN 2003:708643 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


O

O

HO

OH

R

I

Eight flavanone derivs. I (R = Ph, substituted Ph) were prepd. by condensation of RCHO with malonic acid followed by cyclization with 1,3,5-benzenetriol. The biol. examn. showed that some of these compds. had good molluscicidal activity.

Abstract

Synthesis and molluscicidal activity of flavanone derivatives. Qin, Zhanglan; Hu, Lihong; Pan, Kehua; Wei, Yunjie. Department of Chemistry, Central China Normal University, Wuhan, Peop. Rep. China. Huaxue Yanjiu Yu Yingyong (2002), 14(4), 475-476, 483. Publisher: Huaxue Yanjiu Yu Yingyong Bianjibu, CODEN: HYYIFM ISSN: 1004-1656. Journal written in Chinese. CAN 140:321201 AN 2003:686094 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A no. of flavonoids have been detected in buds and young needles in seven species of the genus Picea, four within the genus Pinus and seven species within the genus Abies. The flavonoids were characterized by means of chromatog. (HPLC), spectroscopic (UV) and spectrometric (MS) properties. Twenty-six flavonols, two flavones, four dihydroflavonols together with one dihydrochalcone and one flavanone are reported, together with the relative abundances of the compds. within each species. Several flavonoids are reported for the first time from the investigated trees.Among the flavonol glycosides found both in Picea and Abies, six 3-(6''-acetyl-glucosides) and other acetyl-glucosides were detected. The most abundant sugar-moieties connected to the flavonoids are glucose and rutinose. Flavonol-rhamnosides are present only in the Abies species. This genus also contains two flavone C-glycosides that occur as the main flavonoids in some of the species. The Pinus species stood out for their less diverse content of flavonoids at this stage of development compared to Picea and Abies.

Abstract

Flavonoids in buds and young needles of Picea, Pinus and Abies. Slimestad, R. PlantChem, Sandnes, Norway. Biochemical Systematics and Ecology (2003), 31(11), 1247-1255. Publisher: Elsevier Science B.V., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 141:20376 AN 2003:686440 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


second pharmacophore describes a para-substituted phenolic B ring that requires unsubstituted meta and ortho positions. Based upon this, it indicates that hydroxylation at the 4'-position and a free 5'-position are sufficient for COX-2-inhibiting activity. The potency assocd. with this pharmacophore is modulated by log P2 and by the mol. wt.


flavanone

Constituents of the Stem Bark of Pongamia pinnata with the Potential to Induce Quinone Reductase. Carcache-Blanco, Esperanza J.; Kang, Young-Hwa; Park, Eun Jung; Su, Bao-Ning; Kardono, Leonardus B. S.; Riswan, Soedarsono; Fong, Harry H. S.; Pezzuto, John M.; Kinghorn, A. Douglas. Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL, USA. Journal of Natural Products (2003), 66(9), 1197-1202. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 139:320060 AN 2003:679486 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Micellar electrokinetic chromatog. (MEKC) was applied for enantiosepn. of selected flavanones, including naringin, hesperidin, neohesperidin, naringenin, hesperetin, pinostrobin, isosakuranetin, eriodictyol, and homoeriodictyol. γ-Cyclodextrin (γ-CD) and sodium cholate (SCh) were used as chiral modifiers inducing enantio-selectivity to the background electrolyte. From among many studied selectors only these two appeared to possess the best enantioselective properties in respect to studied flavanones. The mechanisms of their action are a little different; SCh used above crit. micelle point concn. forms chiral micelles itself while γ-CD is deprived of this property and requires addn. of surfactants as, e.g., sodium dodecyl sulfate. SCh enables sepn. of flavanone glycosides diastereomers while sepn. of enantiomers of flavanone aglycons may be achieved with γ-CD. Consideration of structural relation led to the suggestion that interaction of sugar moiety of glycosides with SCh micelles give rise to chiral recognition. MEKC appeared to be a suitable and efficient anal. tool to follow enantiomeric compn. of flavanones.

Abstract

Separation of some chiral flavanones by micellar electrokinetic chromatography. Asztemborska, Monika; Miskiewicz, Magdalena; Sybilska, Danuta. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, Pol. Electrophoresis (2003), 24(15), 2527-2531. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: ELCTDN ISSN: 0173-0835. Journal written in English. CAN 139:403128 AN 2003:684012 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The 2S- and 2R-diastereomers of major flavanone-7-O-glycosides found in sweet orange (Citrus sinensis), mandarine (Citrus deliciosa), grapefruit (Citrus paradisi), lemon (Citrus limon), and sour or bitter orange juice (Citrus aurantium) were sepd. for the first time by chiral capillary electrophoresis (CE) employing various buffers with combined chiral selectors. Native cyclodextrins (CDs), neutral and charged CD derivs. were examd. as chiral additives to the background electrolyte (BGE). Sepn. efficiency has not proved satisfactory with one single CD as chiral selector in the buffer, a full and simultaneous sepn. could often be achieved only by using combined buffer with two different CDs. Chiral sepn. of major flavanones in sweet orange, mandarine and grapefruit juices raised more difficulties than in lemon and sour orange juices as narirutin will not readily build complexes with most CDs. Diastereomeric flavanones of mature and immature grapefruits were compared and some differences were found: naringin showed different diastereomeric ratio and 2S-prunin appeared only in immature grapefruit. Marmalade was also examd. by chiral CE. Its major flavanones corresponded to flavanone pattern of mixed sour and sweet oranges.

Abstract

Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis. Gel-Moreto, Nuria; Streich, Rene; Galensa, Rudolf. Institut fuer Lebensmittelwissenschaft und -chemie, Rheinische Friedrich-Wilhelms-Universitaet Bonn, Bonn, Germany. Electrophoresis (2003), 24(15), 2716-2722. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: ELCTDN ISSN: 0173-0835. Journal written in English. CAN 139:322532 AN 2003:684036 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 897:

The flavonoid compds. of Larix sibirica Ledeb. and Larix gmelinii (Rupr.) Rupr. bark were investigated. Their classification was carried out according to modern views on their biochem. interrelations. It was shown that in the bark there were representatives of practically all flavonoid classes, from flavanone naringenin up to biflavonoids, proanthocyanidins and condensed tannins. Notably, the flavonoid compds. can be classified into two basic groups, judging from B ring hydroxylation type, p-hydroxyphenyl (monosubstituted) and catechol (disubstituted), with the prevalence of the first type. Obviously, biflavonoids of a spiro-type are present in oligo- and polymeric flavonoids compds. as structural parts.

Abstract

Flavonoid compounds of Larix sibirica and Larix gmelinii bark. Ivanova, S. Z.; Fedorova, T. E.; Ivanova, N. V.; Fedorov, S. V.; Ostroukhova, L. A.; Malkov, Yu. A.; Babkin, V. A. Irk. Inst. Khim. im. A. E. Favorskogo, SO RAN, Irkutsk, Russia. Khimiya Rastitel'nogo Syr'ya (2003), Volume Date 2002, (4), 5-13. Publisher: IzdatelÏstvo Altaiskogo Gosudarstvennogo Universiteta, CODEN: KRSHC4 ISSN: 1029-5151. Journal written in Russian. CAN 140:300406 AN 2003:669598 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effects of abscisic acid (ABA) and 2,4-D on the expression of seven anthocyanin biosynthetic pathway genes in 'Kyoho' grape berries were investigated. In untreated berries, the expression of the UDP-glucose-flavonoid: 3-O-glucosyltransferase (UFGT) gene was detected only at 42 d after full bloom (DAB), whereas the phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS), chalcone isomerase (CHI), flavanone-3-hydroxylase (F3H), dihydroflavonol 4-reductase (DFR) and leucoanthocyanidin dioxygenase (LDOX) genes were expressed throughout the growing period. ABA increased anthocyanin content in the skin and the expression of PAL, CHS, CHI, DFR and UFGT genes at 7 d after treatment. In contrast, 2,4-D inhibited the accumulation of anthocyanin and the expression of all the genes examd. Thus, the anthocyanin levels resulting from the application of ABA and 2,4-D were correlated with the expression of anthocyanin biosynthetic pathway genes.

Abstract

Abscisic acid and 2,4-dichlorophenoxyacetic acid affect the expression of anthocyanin biosynthetic pathway genes in 'Kyoho' grape berries. Ban, T.; Ishimaru, M.; Kobayashi, S.; Shiozaki, S.; Goto-Yamamoto, N.; Horiuchi, S. Faculty of Life and Environmental Science, Shimane University, Kamihonjo, Matsue, Shimane, Japan. Journal of Horticultural Science & Biotechnology (2003), 78(4), 586-589. Publisher: Headley Brothers Ltd., CODEN: JHSBFA ISSN: 1462-0316. Journal written in English. CAN 139:287621 AN 2003:670508 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Activity-guided fractionation of the petroleum ether and Et acetate exts. of the stem bark of Pongamia pinnata, using cultured Hepa 1c1c7 mouse hepatoma cells to evaluate quinone reductase (QR) inducing activity, led to the isolation of four new flavanone derivs. (1-4), one new flavone (5), one new chalcone (6), and 13 known compds. of the flavonoid, terpenoid, and fatty acid types. The structures of 1-6 were characterized on the basis of the interpretation of their spectroscopic data. The abs. stereochem. of compds. 1-4 was detd. from their CD data and by Mosher ester detn. All isolates obtained were evaluated in the quinone reductase induction assay.

Abstract


flavanone

Answer 899:

Petunia hybrida and Citrus paradisi have significantly different flavonoid accumulation patterns. Petunia sp. tend to accumulate flavonol glycosides and anthocyanins while Citrus paradisi is known for its accumulation of flavanone diglycosides. One possible point of regulation of flavanone metab. is flavanone 3-hydroxylase (F3H) expression. To test whether this is a key factor in the different flavanone usage by Petunia hybrida and Citrus paradisi, F3H mRNA expression in seedlings of different developmental stages was measured using semiquant. RT-PCR. Primers were designed to conserved regions of F3H and used to amplify an approx. 350 bp segment for quantitation by PhosphorImaging. Primary leaves of 32-day-old grapefruit seedlings and a grapefruit flower bud had the highest levels of F3H mRNA expression. Petunia seedlings had much lower levels of F3H mRNA expression relative to grapefruit. The highest expression in petunia was in primary leaves and roots of 65-day-old seedlings. These results indicate that preferential use of naringenin for prodn. of high levels of flavanone glycosides in young grapefruit leaves cannot be attributed to decreased F3H mRNA expression.

Abstract

Flavanone 3-hydroxylase expression in Citrus paradisi and Petunia hybrida seedlings. Pelt, Jennifer L.; Downes, W. Andrew; Schoborg, Robert V.; McIntosh, Cecilia A. Department of Biological Sciences, East Tennessee State University, Johnson City, TN, USA. Phytochemistry (Elsevier) (2003), 64(2), 435-444. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:361685 AN 2003:667815 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OO

OH

OH

MeMe

CH 2O

I

Bioactivity-guided fractionation of the EtOAc ext. from leaves of Piper crassinervium yielded three prenylated hydroquinones - the E and Z isomers of 1,4-dihydroxy-2-(3',7'-dimethyl-1'-oxo-2',6'-octadienyl)benzene and I - together with the known flavanones naringenin and sakuranetin. The structures were detd. by means of spectroscopic anal. (NMR, IR, UV and MS), including two-dimensional NMR spectroscopy expts. (1H-1H COSY, HMQC, HMBC and NOESY). The antifungal activity was detd. by direct bioautog. against Cladosporium cladosporioides and C. sphaerospermum.

Abstract

Antifungal flavanones and prenylated hydroquinones from Piper crassinervium Kunth. Danelutte, Ana Paula; Lago, Joao Henrique G.; Young, Maria Claudia M.; Kato, Massuo J. Instituto de Quimica, Universidade de Sao Paulo, Sao Paulo, Brazil. Phytochemistry (Elsevier) (2003), 64(2), 555-559. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:361624 AN 2003:667829 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

O

O

O

O

O

N

Me

OH

O

H

N

HMe

O

O

Et

R1

R2

R3

I

III

II

Several flavones I (R1 = MeO; R2 = H; R1R2 = OCH2O), flavanones II (R3 = H, MeO), and 5'-substituted-2'-hydroxy chalcones, e.g., III, have been synthesized through Claisen Schmidt condensation. Condensation of 5-Chloromethyl-2-hydroxyacetophenone with various arom. aldehydes yielded chalcones, which were cyclized, in the presence of SeO2, to the corresponding flavones I. Condensation of 5-(2-methylphenylamino)methyl-2-hydroxyacetophenone with arom. aldehydes gave the corresponding chalcones and flavones. The synthesized flavonoid derivs. were evaluated for their antiinflammatory activity on carrageenan induced paw edema in rats and in vitro antibacterial activity. The results have been encouraging.

Abstract

Synthesis, antiinflammatory and antibacterial activity of some new flavonoidal derivatives. Khan, M. S. Y.; Hasan, S. M. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, New Delhi, India. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (2003), 42B(8), 1970-1974. Publisher: National Institute of Science Communication, CODEN: IJSBDB ISSN: 0376-4699. Journal written in English. CAN 140:128244 AN 2003:661356 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Comparative performances of selected chiral HPLC, SFC, and CE systems with a chemically diverse sample set. Borman, Bibliographic Information Answer 902:

Pyridinyl derivs. of chalcones and flavones have been synthesized in order to investigate their antioxidant properties. Flavones are synthesized by oxidative cyclization of the chalcones in the presence of alk. solns. of hydrogen peroxide. However, under the alk. conditions used to synthesize the chalcones, cycloisomerization of ortho-hydroxy chalcones to isomeric flavanones complicates the transformation of these compds. to the desired flavones. To prevent this, the hydroxy groups of di-and trihydroxyacetophenones are replaced with methoxy groups. Protection of the phenolic oxygens with Me groups facilitates condensation and impedes cycloisomerization of resulting chalcone to the flavanone. Demethylation results on treatment of the dimethoxychalcones with trimethylsilyliodide (TMSI). The deprotected polyhydroxychalcones can then be oxidatively cyclized to the desired flavones. All the products synthesized were analyzed by either GC-MS or HPLC, and proton NMR spectroscopy.

Abstract

Synthesis of 1-(di- and trihydroxyphenyl)-3-pyridinepropenones: Precursors for pyridine 3-chromones. Rafiq, Somaira; Wachter, Nanette M. Department of Chemistry, Hofstra University, Hempstead, NY, USA. Abstracts of Papers, 226th ACS National Meeting, New York, NY, United States, September 7-11, 2003 (2003), CHED-189. Publisher: American Chemical Society, Washington, D. C CODEN: 69EKY9 Conference; Meeting Abstract written in English. AN 2003:630530 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new butenylflavanone, (2S)-5-hydroxy-7-methoxy-8-[(E)-3-oxo-1-butenyl]flavanone (1), and a new rotenoid, 4',5'-dihydro-11,5'-dihydroxy-4'-methoxytephrosin (2), as well as three active flavonoids of previously known structure, isoliquiritigenin (3), genistein (4), and chrysoeriol (5), along with nine known inactive compds., α-toxicarol (6), sumatrol, 6a,12a-dehydro-α-toxicarol, 11-hydroxytephrosin, obovatin, marmesin, lupenone, benzyl benzoate, and benzyl trans-cinnamate, were isolated from an Et acetate-sol. ext. of the stems of Tephrosia toxicaria, using a bioassay based on the induction of quinone reductase (QR) in cultured Hepa 1c1c7 mouse hepatoma cells to monitor chromatog. fractionation. The structures of compds. 1 and 2 were elucidated by spectroscopic data interpretation. All isolates were evaluated for their potential cancer chemopreventive properties utilizing an in vitro assay to det. quinone reductase induction. Selected compds. were tested in a mouse mammary organ culture assay to evaluate the inhibition of 7,12-dimethylbenz[a]anthracene (DMBA)-induced preneoplastic lesions.

Abstract

Potential Cancer Chemopreventive Flavonoids from the Stems of Tephrosia toxicaria. Jang, Dae Sik; Park, Eun Jung; Kang, Young-Hwa; Hawthorne, Michael E.; Vigo, Jose Schunke; Graham, James G.; Cabieses, Fernando; Fong, Harry H. S.; Mehta, Rajendra G.; Pezzuto, John M.; Kinghorn, A. Douglas. Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, and Department of Surgical Oncology, College of Medicine, University of Illinois at Chicago, Chicago, IL, USA. Journal of Natural Products (2003), 66(9), 1166-1170. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 139:304575 AN 2003:657115 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Luteolin and Orobol were synthesized in three steps via chloromethyl Me ether protected ketone phenol and aldehyde phenol, forming chalcone deriv., further oxidative intramol. cyclization, giving polyhydroxy flavanone and isoflavanone. The overall yield of Luteolin

Abstract

Synthesis of Luteolin and Orobol. Ge, Xia; Li, Jianqi. Shanghai Institute of Pharmaceutical Industry, Shanghai, Peop. Rep. China. Zhongguo Yiyao Gongye Zazhi (2003), 34(4), 159-161. Publisher: Zhongguo Yiyao Gongye Zazhi Bianjibu, CODEN: ZYGZEA ISSN: 1001-8255. Journal written in Chinese. CAN 140:111145 AN 2003:597202 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Potent antioxidative hydroxyflavanones were produced with Aspergillus saitoi from hesperidin or naringin, which are flavanone glycosides in citrus fruit with weak antioxidative activity. The hydroxyflavanone produced from hesperidin was identified as 8-hydroxyhesperetin (8-HHE), a novel substance, and those from naringin were identified as carthamidin (6-hydroxynaringenin) and isocarthamidin (8-hydroxynaringenin) by FAB-MS, 1H-NMR and 13C-NMR analyses. The antioxidative activity of these hydroxyflavanones was examd. by using the free radical-scavenging system of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and the Me linoleate oxidn. system. The hydroxyflavanones (8-HHE, carthamidin, and isocarthamidin) exhibited stronger activity than the flavanone glycosides (hesperidin or naringin) and their aglycons (hesperetin or naringenin). The activity of 8-HHE and isocarthamidin was comparable to that of α-tocopherol, and that of carthamidin was weaker than that of isocarthamidin. The hydroxyflavanones, which were hydroxylated on A ring of flavanone by Aspergillus saitoi, were obtained as potent antioxidants.

Abstract

New potent antioxidative hydroxyflavanones produced with Aspergillus saitoi from flavanone glycoside in citrus fruit. Miyake, Yoshiaki; Minato, Kenichiro; Fukumoto, Syuichi; Yamamoto, Kanefumi; Oya-Ito, Tomoko; Kawakishi, Syunro; Osawa, Toshihiko. Fundamental Technical Research Department of Pokka Corporation Ltd., Aichi, Japan. Bioscience, Biotechnology, and Biochemistry (2003), 67(7), 1443-1450. Publisher: Japan Society for Bioscience, Biotechnology, and Agrochemistry, CODEN: BBBIEJ ISSN: 0916-8451. Journal written in English. CAN 139:306597 AN 2003:613685 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Pharmaceutical companies have a continuous need to resolve new racemates. Anal. may be required in aq. and nonaq. media, or in the presence of several different sets of potentially interfering compds. There is often a preparative requirement. For these reasons analysts may require a no. of different sepn. systems capable of resolving a given pair of enantiomers. The authors wished to improve upon existing approaches that address this situation and undertook a program of work to screen over 100 racemates, selected for their chem. diversity, on over 100 different chiral HPLC, SFC, and CE systems. Here the authors report results of this comparison and illustrate the use of rapid gradient screening as a valuable tool for chiral method development.

Abstract

Phil; Boughtelower, Bob; Cattanach, Kaye; Crane, Kathy; Freebairn, Keith; Jonas, Greg; Mutton, Ian; Patel, Asha; Sanders, Matt; Thompson, Duncan. Strategic Technologies, GlaxoSmithKline, Stevenage, UK. Chirality (2003), 15(Suppl.), S1-S12. Publisher: Wiley-Liss, Inc., CODEN: CHRLEP ISSN: 0899-0042. Journal written in English. CAN 139:373796 AN 2003:625324 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


A method was developed for the sepn. of diastereomers of flavanone-7-O-glycosides by capillary electrophoresis using sulfobutyl ether-β-cyclodextrin (SBE-β-CD) in the background electrolyte. The effect of the concn. of the CD additive, buffer pH, and org. modifier on the migration times and resoln. for five flavanone glycosides (naringin, hesperidin, neohesperidin, narirutin, and eriocitrin) was studied. Baseline sepns. of these compds. as pairs of diastereoisomers were achieved with 20 mM tetraborate buffer at pH 7 contg. 5 mg/mL of SBE-β-CD and 10% (vol./vol.) of methanol. The developed method was used for the qual. anal. of the diastereomeric compn. of the major flavanone glycosides in different citrus juices. The ability of SBE-β-CD to discriminate flavanone enantiomers was also studied.

Abstract

Separation of diastereomers of flavanone-7-O-glycosides by capillary electrophoresis using sulfobutyl ether-β-cyclodextrin as the selector. Aturki, Zeineb; Sinibaldi, Massimo. Istituto di Metodologie Chimiche, CNR - Area della Ricerca di Roma, Rome, Italy. Journal of Separation Science (2003), 26(9/10), 844-850. Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, CODEN: JSSCCJ ISSN: 1615-9306. Journal written in English. CAN 139:316176 AN 2003:589969 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Benzophenone derivs., such as polyprenylated benzoylphloroglucinols and xanthones, are biol. active secondary metabolites. The formation of their C13 skeleton is catalyzed by benzophenone synthase (BPS; EC 2.3.1.151) that has been cloned from cell cultures of Hypericum androsaemum. BPS is a novel member of the superfamily of plant polyketide synthases (PKSs), also termed type III PKSs, with 53-63% amino acid sequence identity. Heterologously expressed BPS was a homodimer with a subunit mol. mass of 42.8 kDa. Its preferred starter substrate was benzoyl-CoA that was stepwise condensed with three malonyl-CoAs to give 2,4,6-trihydroxybenzophenone. BPS did not accept activated cinnamic acids as starter mols. In contrast, recombinant chalcone synthase (CHS; EC 2.3.1.74) from the same cell cultures preferentially used 4-coumaroyl-CoA and also converted CoA esters of benzoic acids. The enzyme shared 60.1% amino acid sequence identity with BPS. In a phylogenetic tree, the two PKSs occurred in different clusters. One cluster was formed by CHSs including the one from H. androsaemum. BPS grouped together with the PKSs that functionally differ from CHS. Site-directed mutagenesis of amino acids shaping the initiation/elongation cavity of CHS yielded a triple mutant (L263M/F265Y/S338G) that preferred benzoyl CoA over 4-coumaroyl-CoA.

Abstract

Benzophenone synthase and chalcone synthase from Hypericum androsaemum cell cultures: cDNA cloning, functional expression, and site-directed mutagenesis of two polyketide synthases. Liu, Benye; Falkenstein-Paul, Hildegard; Schmidt, Werner; Beerhues, Ludger. Institut fuer Pharmazeutische Biologie, Braunschweig, Germany. Plant Journal (2003), 34(6), 847-855. Publisher: Blackwell Publishing Ltd., CODEN: PLJUED ISSN: 0960-7412. Journal written in English. CAN 140:195315 AN 2003:592032 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


and Orobol was 22% and 15%, resp.


flavanone

Twelve pure compds., namely viridiflorol; squalene; β-sitosterol; 5-hydroxy-3,6,7,3',4'-pentamethoxy flavone; Abstract

Chemical constituents of Vitex negundo leaves. Singh, Virendra; Dayal, Rameshwar; Bartley, John P. Chemistry Division, Forest Research Institute, Dehra dun, India. Journal of Medicinal and Aromatic Plant Sciences (2003), 25(1), 94-98. Publisher: Central Institute of Medicinal and Aromatic Plants, CODEN: JMASF6 Journal written in English. CAN 140:108101 AN 2003:565179 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Four chalcone glycosides, including three new natural products, and three flavanones were isolated from the methanol ext. of stem bark of Maclura tinctoria. The new compds. have been characterized as 4'-O-β-D-(2''-p-coumaroyl)glucopyranosyl-4,2',3'-trihydroxychalcone, 4'-O-β-D-(2''-p-coumaroyl-6''-acetyl)glucopyranosyl-4,2',3'-trihydroxychalcone, and 3'-(3-methyl-2-butenyl)-4'-O-β-D-glucopyranosyl-4,2'-dihydroxychalcone (I); the known derivs. were elucidated as 4'-O-β-D-(2''-acetyl-6''-cinnamoyl)glucopyranosyl-4,2',3'-trihydroxychalcone, eriodictyol 7-O-β-D-glucopyranoside, naringenin, and naringenin 4'-O-β-D-glucopyranoside. Their structures were detd. by 1D and 2D NMR and ESIMS. The antioxidant activity of all isolated compds. was detd. by measuring free-radical-scavenging effects using two different assays, namely, the Trolox Equiv. Antioxidant Capacity (TEAC) assay and the coupled oxidn. of β-carotene and linoleic acid (autoxidn. assay). The results showed that I was the most active in both antioxidant assays.

Abstract

Antioxidant Chalcone Glycosides and Flavanones from Maclura (Chlorophora) tinctoria. Cioffi, Giuseppina; Escobar, Luis Morales; Braca, Alessandra; De Tommasi, Nunziatina. Dipartimento di Scienze Farmaceutiche, Universita di Salerno, Fisciano, Italy. Journal of Natural Products (2003), 66(8), 1061-1064. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 139:242982 AN 2003:576500 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The absorption and fluorescence emission spectra of substituted flavanones viz., flavanone, 6-Me flavanone, and 6-methyl-4'-methoxy flavanone, have been reported in various polar and nonpolar org. solvents. The values of excited state dipole moments of these flavanones have been calcd., using solvatochromic data. The values of excited state dipole moments for all these mols. studied, are higher than their corresponding values in the ground state. Also the excited state dipole moment of 6-methyl-4'-methoxy flavanone > 6-Me flavanone > flavanone. Further, the values of percentage polarization of these mols. in various solvents of different polarity have been obtained and interpreted in terms of Perrin's theory as well as dipole-dipole interaction. Also, the effect of temp. on fluorescence intensity in H2O and a nonpolar solvent have been obsd. The variations in the fluorescence intensity have been discussed in terms of the positions of 1(π π*) and 3(n π*) energy levels of the mols. studied.

Abstract

Influence of solvents and temperature on the photophysical characteristics of flavanones. Giri, Rajesh; Tiwari, Yatendra. Department of Physics, Rajdhani College (Delhi University), New Delhi, India. Indian Journal of Pure and Applied Physics (2003), 41(7), 530-537. Publisher: National Institute of Science Communication, CODEN: IJOPAU ISSN: 0019-5596. Journal written in English. CAN 139:329605 AN 2003:587691 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Three anthocyanin regulatory genes of maize (Zea mays; Lc, B-Peru, and C1) were introduced into alfalfa (Medicago sativa) in a strategy designed to stimulate the flavonoid pathway and alter the compn. of flavonoids produced in forage. Lc constructs included a full-length gene and a gene with a shortened 5'-untranslated region. Lc RNA was strongly expressed in Lc transgenic alfalfa foliage, but accumulation of red-purple anthocyanin was obsd. only under conditions of high light intensity or low temp. These stress conditions induced chalcone synthase and flavanone 3-hydroxylase expression in Lc transgenic alfalfa foliage compared with non-transformed plants. Genotypes contg. the Lc transgene construct with a full-length 5'-untranslated region responded more quickly to stress conditions and with a more extreme phenotype. High-performance liq. chromatog. anal. of field-grown tissue indicated that flavone content was reduced in forage of the Lc transgenic plants. Leucocyanidin reductase, the enzyme that controls entry of metabolites into the proanthocyanidin pathway, was activated both in foliage and in developing seeds of the Lc transgenic alfalfa genotypes. Proanthocyanidin polymer was accumulated in the forage, but (+)-catechin monomers were not detected. B-Peru transgenic and C1 transgenic populations displayed no visible phenotypic changes, although these transgenes were expressed at detectable levels. These results support the emerging picture of Lc transgene-specific patterns of expression in different recipient species. These results demonstrate that proanthocyanidin biosynthesis can be stimulated in alfalfa forage using an myc-like transgene, and they pave the way for the development of high quality, bloat-safe cultivars with ruminal protein bypass.

Abstract

Expression of anthocyanins and proanthocyanidins after transformation of alfalfa with maize Lc. Ray, Heather; Yu, Min; Auser, Patricia; Blahut-Beatty, Laureen; McKersie, Brian; Bowley, Steve; Westcott, Neil; Coulman, Bruce; Lloyd, Alan; Gruber, Margaret Y. Saskatoon Research Centre, Agriculture and Agri-Food Canada, Saskatoon, SK, Can. Plant Physiology (2003), 132(3), 1448-1463. Publisher: American Society of Plant Biologists, CODEN: PLPHAY ISSN: 0032-0889. Journal written in English. CAN 139:225152 AN 2003:555282 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Isoflavone levels in Glycine max (soybean) were increased via metabolic engineering of the complex phenylpropanoid biosynthetic pathway. Phenylpropanoid pathway genes were activated by expression of the maize C1 and R transcription factors in soybean seed, which decreased genistein and increased the daidzein levels with a small overall increase in total isoflavone levels. Cosuppression of flavanone 3-hydroxylase to block the anthocyanin branch of the pathway, in conjunction with C1/R expression, resulted in higher levels of isoflavones. The combination of transcription factor-driven gene activation and suppression of a competing pathway provided a successful means of enhancing accumulation of isoflavones in soybean seed.

Abstract

Metabolic engineering to increase isoflavone biosynthesis in soybean seed. Yu, Oliver; Shi, June; Hession, Aideen O.; Maxwell, Carl A.; McGonigle, Brian; Odell, Joan T. Experimental Station, Crop Genetics, E.I. du Pont de Nemours & Company, Inc., Wilmington, DE, USA. Phytochemistry (Elsevier) (2003), 63(7), 753-763. Publisher: Elsevier Science B.V., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:258149 AN 2003:563752 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


5-hydroxy-3,7,3',4'-tetramethoxy flavone; 5,3'-dihydroxy-7,8,4'-trimethoxy flavanone; p-hydroxybenzoic acid; 3,4-dihydroxy benzoic acid; luteolin 7-glucoside; isoorientin; agnuside and 2'-p-hydroxybenzoyl mussaenosidic acid were isolated and characterized by spectral data (UV, IR, NMR & MS) from the different extractives of the leaves. Squalene is reported for the first time from the V. negundo leaves. Agnuside was found to possess significant hepatoprotective activity while viridiflorol exhibited dose dependant antifeedant against Sitophilus oryzae and ovipositional activity against Callosobruchus chinensis.


flavanone

2,4,6-Tris(methoxymethoxy)acetophenone was first mono-alkylated with 3-methylbut-2-enyl bromide to yield 5-methyl-1-[2,4,6-tris(methoxymethoxy)phenyl]hex-4-en-1-one (I). The base-catalyzed aldol condensation of I with substituted benzaldehydes gave chalcones in good yields. One-pot cyclization and deprotection of the chalcones afforded (±)-C-3-prenylated flavanones II (R1 = R3 = OH; R2 = R4 = H; R1 = R4 = H; R2 = R3 = OH; R1 = R2 = R4 = H; R3 = OMe, OH; R1 = R3 = R4 = OMe; R2 = H).

Abstract

First Synthesis of (±)-C-3-Prenylated Flavanones. Xu, Jin; Wang, Haishan; Mui Sim, Mui. Medicinal and Combinatorial Chemistry Laboratory, Institute of Molecular and Cell Biology, Singapore, Singapore. Synthetic Communications (2003), 33(15), 2737-2750. Publisher: Marcel Dekker, Inc., CODEN: SYNCAV ISSN: 0039-7911. Journal written in English. CAN 139:395780 AN 2003:539685 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review is given on the radiochem. marking of flavonoids with 11C for radiopharmaceutical examns. with positron emission tomog. 11C synthesis methods are outlined and examples of resulting flavonoids are given such as hesperitin, glycetein, xanthotumol-like flavonoids and flavanones, and resveratrol.

Abstract

Flavonoids: Mechanism of action and application possibilities (part 2). Bergmann, Ralf; Wuest, Frank; Pietzsch, Jens. Institut fuer Bioanorganische und Radiopharmazeutische Chemie, Forschungszentrum Rossendorf, Dresden, Germany. Bioforum (2003), 26(6), 384-385. Publisher: GIT Verlag GmbH & Co. KG, CODEN: BFRME3 ISSN: 0940-0079. Journal; General Review written in German. CAN 139:113689 AN 2003:553014 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Antitumor agents, esp. useful for treatment of skin cancers, contain artocarpins I (R = H, C1-10 alkyl, acyl) as active ingredients. IC50 of artocarpin (II) against B16 melanoma cells was 5.4 μM, vs. 50 μM of vinblastine sulfate. II also inhibited proliferation of human melanoma cells, human breast cancer MCF-7 cells, human leukemia HL 60 cells, and HeLa cells. In vivo antitumor effect of II in mice bearing B16 melanoma cells was excellent.


Antitumor agents containing artocarpin or its analogs. Kondo, Ryuichiro; Shimizu, Kuniyoshi; Yoshikawa, Keisuke. (Kansai Koso Co., Ltd., Japan). Jpn. Kokai Tokkyo Koho (2003), 4 pp. CODEN: JKXXAF JP 2003192590 A 20030709 Patent written in Japanese. Application: JP 2001-394637 20011226. Priority: . CAN 139:63323 AN 2003:527529 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O Me

Me

O

O

OOH

HO

Me

Me

OMOM

OMOM

MOM

R1

R3

R4

R2

I

II


flavanone

Study on the chemical constituents of Populus davidiana Dode. Zhou, Shan; Lin, Mao; Wang, Yinghong; Liu, Xin. Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing, Peop. Rep. China. Tianran Chanwu Yanjiu Yu Kaifa (2002), 14(5), 43-45. Publisher: Tianran Chanwu Yanjiu Yu Kaifa Bianjibu, CODEN: TCYKE5 ISSN: 1001-6880. Journal written in Chinese. CAN 139:361600 AN 2003:522493 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The invention relates to a cometic compn. for refilling, e.g. shampoo, body soap, cleansing gel, etc., wherein the compn. contains ketone fragrances having a steam pressure at 25° of 0.001-7 mmHg and a HLB of 2-13, and wherein the compn. is sealed in a container having aluminum deposition layer. The cosmetic compn. of the present invention has improved stability, esp. the aroma stability.


Cosmetic composition packaged with material having Al-deposition layer for refilling. Nishida, Yuichi; Kon, Akira; Tobe, Hidetake. (Lion Corp., Japan). Jpn. Kokai Tokkyo Koho (2003), 16 pp. CODEN: JKXXAF JP 2003192560 A 20030709 Patent written in Japanese. Application: JP 2001-403023 20011227. Priority: . CAN 139:73723 AN 2003:525350 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


OO

O O

O O

R

R

R

R

I


flavanone

Answer 919:

Analyses of attainable primary amino acid sequences, assigned secondary structures and superimposed tertiary structures of 142 isopenicillin N synthase (IPNS) related non-heme iron-dependent oxygenases and oxidases (designated as NHIDOX) were examd. in this study. Despite having low sequence homologies (.apprx.20%), these enzymes were found to possess conserved structural domains (delineated as modules I and II) that fold into jelly-roll motifs, juxtaposed by adjacent stabilizing elements. The seven highly conserved residues, corresponding to His214, Asp216 and His270 in Aspergillus nidulans IPNS (IPNS_AN) for iron binding, Arg279 and Ser281 for substrate/co-substrate binding, as well as Gly40 and Gly254 with yet undetd. functions, are arrayed closely within these conserved modules. Complex hydrogen bonding interactions of these conserved residues with residues found in specific α-helixes and β-strands of the conserved core motif are apparently involved in stabilizing these structures. Although the NHIDOX enzymes appear to share conserved active center architecture, differences in their hydrogen bonding networks were obsd., particularly those involving the substrate/co-substrate binding ligands and the two conserved glycines. These may modulate functional versatilities, relative sizes of the jelly-roll motifs, and the specific amino acid residues involved in stabilization and folding of the active center.

Abstract

Conserved structural modules and bonding networks in isopenicillin N synthase related non-haem iron-dependent oxygenases and oxidases. Sim, Janet; Wong, Esther; Chin, Hong Soon; Sim, Tiow Suan. Faculty of Medicine, Department of Microbiology, National University of Singapore, Singapore, Singapore. Journal of Molecular Catalysis B: Enzymatic (2003), 23(1), 17-27. Publisher: Elsevier Science B.V., CODEN: JMCEF8 ISSN: 1381-1177. Journal written in English. CAN 140:141603 AN 2003:521546 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. constituents of Spatholobus suberectus (jixueteng) Dunn were studied. The constituents of Spatholobus suberectus were sepd. with various chromatog. techniques. The structures were elucidated by physico-chem. properties and spectral data. Eight compds. were isolated from Spatholobus suberectus Dunn and identified as suberectin (1), formononetin (2), daidzein, calycosin (4), pyromucic acid (5), 1,3,5-benzenetriol (6), succinic acid (7), and β-sitosterol (8). Suberectin was a new compd. and characterized as 7,3',4'-trihydroxy-6-methoxyflavanone based on chem. and spectral evidence. Compds. 4, 5, 6, and 7 were obtained from Spatholobus genus for the first time.

Abstract

Studies on the chemical constituents of Spatholobus suberectus Dunn. Cui, Yanjun; Liu, Ping; Chen, Ruoyun. Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, Peop. Rep. China. Yaoxue Xuebao (2002), 37(10), 784-787. Publisher: Yaoxue Xuebao Bianjibu, CODEN: YHHPAL ISSN: 0513-4870. Journal written in Chinese. CAN 140:14805 AN 2003:522473 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


From the bark of Populus davidiana Dode., seven flavonoids were isolated and identified as galangin, chrysin, tectochrysin, genkwanin, ombuin, pinocembrin and trans-3-acetoxy-5,7-dihydroxyflavanone, resp. Ombuin and trans-3-acetoxy-5,7-dihydroxy-flavanone were isolated from the genus for the first time. Galangin, tectochrysin and ombuin had strong anti-inflammatory activity.

Abstract


flavanone

JP 2005513492 T 20050512 JP 2003-556165 20021217


EP 1458475 A2 20040922 EP 2002-805798 20021217AU 2002364659 B2 20080228AU 2002364659 A1 20030715 AU 2002-364659 20021217

RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, SI, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW

WO 2003055594 A3 20031224WO 2003055594 A2 20030710 WO 2002-FR4391 20021217FR 2834227 A1 20030704 FR 2001-16933 20011227Patent No. Kind Date Application No. Date Patent Family Information

Chiral stationary phases made from esters or carbamates of polysaccharides or oligosaccharides. Duval, Raphael; Leveque, Hubert. (Chiralsep, Fr.). Fr. Demande (2003), 23 pp. CODEN: FRXXBL FR 2834227 A1 20030704 Patent written in French. Application: FR 2001-16933 20011227. Priority: . CAN 139:78012 AN 2003:516845 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The bpha1(2072)A2A3A4 gene cluster codes for a modified biphenyl dioxygenase holoenzyme with broad substrate specificity. In the previous report, we have shown the biotransformation of flavone, flavanone, 6-hydroxyflavone and 6-hydroxyflavanone by Streptomyces lividans cells carrying bphA1(2072)A2A3A4. In the present study, we successfully biotransformed chalcone and 7-hydroxyisoflavone, which are categorized with other groups of flavonoids, by using recombinant Escherichia coli cells expressing the same genes. We also biotransformed various flavonoids by E. coli cells expressing the bphB (dihydrodiol dehydrogenase) gene in addn. to the bphA1(2072)A2A3A4 genes. Flavone, flavanone, 6-hydroxyflavone, 6-hydroxyflavanone, chalcone, and 7-hydroxyisoflavone, which were used as substrates, were converted with high efficiency to their corresponding diols, whose structures were detd. by HREI-MS, 1H NMR and 13C NMR data. The antioxidative activity of these generated diol compds. was markedly higher than that of the substrates used.

Abstract

Enzymatic synthesis of novel antioxidant flavonoids by Escherichia coli cells expressing modified metabolic genes involved in biphenyl catabolism. Shindo, Kazutoshi; Kagiyama, Yukiko; Nakamura, Ryoko; Hara, Akihiro; Ikenaga, Hiroshi; Furukawa, Kensuke; Misawa, Norihiko. Department of Food and Nutrition, Japan Women's University, Bunkyo-ku, Tokyo, Japan. Journal of Molecular Catalysis B: Enzymatic (2003), 23(1), 9-16. Publisher: Elsevier Science B.V., CODEN: JMCEF8 ISSN: 1381-1177. Journal written in English. CAN 140:320063 AN 2003:521545 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Molecular cloning and analysis of anthocyanin biosynthesis genes preferentially expressed in apple skin. Kim, Sung-Hyun; Lee, Jae-Rin; Hong, Sung-Tae; Yoo, Yung-Keun; An, Gynheung; Kim, Seong-Ryong. Department of Life Science, Sogang University, Mapo-gu, Seoul, S. Korea. Plant Science (Shannon, Ireland) (2003), 165(2), 403-413. Publisher: Elsevier


Hispidone, a new flavanone, has been isolated from Onosma hispida and assigned the structure (2S)-5,2'-dihydroxy-7,4',5'-trimethoxyflavanone (1) by spectroscopic methods. In addn., (2S)-5,2'-dihydroxy-7,5'-dimethoxyflavanone (2), benzoic acid (3), and 4-hydroxy benzoic acid (4) are also reported for the first time from this species.

Abstract

Cholinesterase inhibitory constituents from Onosma hispida. Ahmad, Ijaz; Anis, Itrat; Malik, Abdul; Nawaz, Sarfraz Ahmad; Choudhary, Muhammad Iqbal. International Centre of Chemical Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi, Pak. Chemical & Pharmaceutical Bulletin (2003), 51(4), 412-414. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 139:374803 AN 2003:503045 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Chiral stationary phases for the chromatog. sepn. or concn. of org., mineral or organo-mineral enantiomers consist of an ester or carbamate or a mixt. of esters and carbamates of polysaccharides or oligosaccharides and a solid org. or mineral support. The support can be an org. polymer, such as polyamides, polystyrene, polyvinylalcs., polyacrylamides, polyolefins, polyvinylethers, polyalkylvinylketones, polyalkynes, polyisocyanates, polyisonitriles, polyoxiranes, polythiiranes, polyazirdines, polyesters, polythioesters, polyurethanes, polyureas, polysulfonamides, or phenol-formaldehyde resins. The support can be an inorg. material, such as titania, alumina, magnesium silicate, zeolites, diatomaceous earth, clays, silicates, or phosphates. The support material has a particle size of 1 μm to 10 mm and a pore size of 1-4000 .ANG.. The optically active material has the general formula PS-(OZ)n with PS representing a polysaccharide or an oligosaccharide with at least 6 glycosidic units, n is 12-30000, and OZ represents OH, -O-C(O)-NH-R, or -O-C(O)-R with R being a C1-40-alkyl, aryl, or alkylaryl group which can be substituted by hetero atoms, such as N, S, O, P, Cl, F, Br, I, or Si. Preferably R can be Ph, tolyl, 3,5-dimethylphenyl, 4-chlorophenyl, 3,5-dichlorophenyl, or 4-tert-butylphenyl. The polysaccharides or oligosaccharides can be cellulose, amylose, starch, chitosan, α, β, or γ-cyclodextrins. The stationary phase is prepd. by dissolving the ester or carbamate of the polysaccharide or oligosaccharide in a polar org. solvent, adding a soln. or suspension of the support, followed by evapg. the solvent at about 100°C, and drying.

Abstract WO 2002-FR4391 W 20021217FR 2001-16933 A 20011227Priority Application NO 2004003125 A 20040927 NO 2004-3125 20040721 US 20050209100 A1 20050922 US 2004-876777 20040628IN 2004CN01422 A 20060210 IN 2004-CN1422 20040624CN 1617762 A 20050518 CN 2002-827629 20021217


flavanone

Answer 925:

This study examd. the effects of astilbin, a flavanone, on delayed-type hypersensitivity reactions and its mechanisms of action on cell migration. Astilbin significantly inhibited the sheep red blood cell-induced footpad reaction and picryl-chloride-induced ear dermatitis without affecting the organ wts., when administered during the effector phase but not the induction phase. The flavanone also significantly inhibited the migration to gelation of spleen cells isolated from mice with ear dermatitis in a transwell system. Furthermore, the isolated spleen cells from normal mice were incubated with astilbin in the presence of Con A, or those from mice with ear dermatitis were cultured with astilbin. In the supernatants collected, the activity of matrix metalloproteinases (MMPs) MMP-2 and MMP-9 was remarkably inhibited by astilbin. These results suggest that astilbin may inhibit delayed-type hypersensitivity reactions through selectively suppressing the lymphocyte functions, including cell migration, via down-regulating MMP activity.

Abstract

Astilbin suppresses delayed-type hypersensitivity by inhibiting lymphocyte migration. Cai, Yu; Chen, Ting; Xu, Qiang. State Key Laboratory of Pharmaceutical Biotechnology, School of Life Sciences, Nanjing University, Nanjing, Peop. Rep. China. Journal of Pharmacy and Pharmacology (2003), 55(5), 691-696. Publisher: Pharmaceutical Press, CODEN: JPPMAB ISSN: 0022-3573. Journal written in English. CAN 139:301593 AN 2003:489931 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A photochem. cyclization reaction of 1-(2'-hydroxy-1'-naphthyl)-3-(1-naphthyl)-2-propen-1-one (1,1-NHC) to give a flavanone deriv. took place in benzene, but did not take place in methanol and the controlling factor of the reaction was discussed based on laser transient spectroscopy and product anal.

Abstract

Mechanistic approach to the cyclization reaction of a 2'-hydroxychalcone analogue with light and solvent. Kaneda, Kaoru; Arai, Tatsuo. Department of Chemistry, University of Tsukuba, Ibaraki, Japan. Organic & Biomolecular Chemistry (2003), 1(12), 2041-2043. Publisher: Royal Society of Chemistry, CODEN: OBCRAK ISSN: 1477-0520. Journal written in English. CAN 139:337755 AN 2003:491903 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Anthocyanin is the major color pigment in plants. In order to understand anthocyanin biosynthesis mechanism in apple, the cDNAs encoding flavanone 3-hydroxylase (F3H), dihydroflavonol reductase (DFR), anthocyanidin synthase (ANS), and UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGT) were isolated from cDNA libraries prepd. from the skin tissues of apple (Malus domestica Borkh. cv. Fuji). Deduced amino acid sequences of the cDNAs showed high homol. to the sequences from other plants. Each gene is a member of a multigene family. The mRNAs of anthocyanin biosynthetic genes were detected preferentially in the skin tissue and expression of the genes was coordinately induced by light. The transcripts were detected abundantly in the skins of cultivars with red skin, but rarely in that of a cultivar carrying non-red fruit, suggesting that these genes have major roles in detn. of apple skin color.

Abstract

Science Ltd., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 139:241076 AN 2003:499086 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone


The morphol., ultrastructure, d. and distribution of trichomes on leaves of Betula pendula, B. pubescens ssp. pubescens, B. pubescens ssp. czerepanovii and B. nana were examd. by means of light, scanning and transmission electron microscopy. The compn. of flavonoids in ethanolic leaf surface exts. was analyzed by HPLC. All taxa examd. contained both glandular and non-glandular trichomes (short and/or long hairs) but differed from each other in trichome ultrastructure, d. and location on the leaf. Leaves of B. pubescens were more hairy than those of B. pendula, but the latter species had a higher d. of glandular trichomes. Of the two subspecies of B. pubescens, leaves of ssp. pubescens had more short hairs on the leaf surface and four times the d. of glandular trichomes of leaves of ssp. czerepanovii, whereas, in the latter subspecies, short hairs occurred largely on leaf veins, as in B. nana. The glandular trichomes were peltate glands, consisting of medullar and cortical cells, which differed structurally. Cortical cells possessed numerous small, poorly developed plastids and small vacuoles, whereas medullar cells had several large plastids with well-developed thylakoid systems and fewer vacuoles. In B. pubescens subspecies, vacuoles of the glandular cells contained osmiophilic deposits, which were probably phenolic, whereas in B. pendula, vacuoles of glandular trichomes were characterized by the presence of numerous myelin-like membranes. The compn. of epicuticular flavonoids also differed among species. The two subspecies of B. pubescens and B. nana shared the same 12 compds., but five of these occurred only in trace amts. in B. nana. Leaf surface exts. of B. pendula contained just six flavonoids, three of which occurred only in this species. In summary, the structure, d. and distribution of leaf trichomes and the compn. of epicuticular flavonoids represent good taxonomic markers for Finnish birch species.

Abstract

Comparative analysis of leaf trichome structure and composition of epicuticular flavonoids in Finnish birch species. Valkama, Elena; Salminen, Juha-Pekka; Koricheva, Julia; Pihlaja, Kalevi. Section of Ecology, Department of Biology, University of Turku, Turku, Finland. Annals of Botany (Oxford, United Kingdom) (2003), 91(6), 643-655. Publisher: Oxford University Press, CODEN: ANBOA4 ISSN: 0305-7364. Journal written in English. CAN 140:73945 AN 2003:457594 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The main objective of this study was to evaluate the capability of 120 arom. chems. to bind to the human alpha estrogen receptor (hERα) by the use of quantum similarity methods. The exptl. data were segregated into two categories, i.e., those compds. with and without estrogenicity activity (active and inactive). To identify potential ligands, semiquant. structure-activity relationships were developed for the complete set correlating the presence or lack of binding affinity to the estrogen receptor with structural features of the mols. The structure-activity relationships were based upon mol. similarity indexes, which implicitly contain information related to changes in the electron distributions of the mols., along with indicator variables, accounting for several structural features. In addn., the whole set was split into several chem. classes for modeling purposes. Models were validated by dividing the complete set into several training and test sets to allow for external predictions to be made.

Abstract

Molecular Quantum Similarity Analysis of Estrogenic Activity. Saliner, Ana Gallegos; Amat, Lluis; Carbo-Dorca, Ramon; Schultz, T. Wayne; Cronin, Mark T. D. Institute of Computational Chemistry, University of Girona, Girona, Spain. Journal of Chemical Information and Computer Sciences (2003), 43(4), 1166-1176. Publisher: American Chemical Society, CODEN: JCISD8 ISSN: 0095-2338. Journal written in English. CAN 139:174985 AN 2003:487449 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Answer 930:

Three Uvaria species, namely U. klaineana, U. mocoli and U. versicolor were tested in vitro against Dermatophagoides pteronyssinus, the European house dust mite. The most active exts. were the Uvaria versicolor stems crude methanol and hexane exts. with EC50 values of 0.095 g/m2 and 0.12 g/m2, resp. The bioassay-guided fractionation of the hexane ext. led to the isolation of benzyl benzoate which exhibited an EC50 value of 0.045 g/m2. A new flavanone, versuvanone, and the known oxoaporphine liriodenine were also isolated from this species and showed EC50 values > 1.5 g/m2. A weak acaricidal activity (0.85 g/m2) was obsd. for the dichloromethane ext. of Uvaria klaineana, due to the presence of benzyl benzoate. Uvaria mocoli was inactive. The structures of compds. were elucidated using 2D-NMR techniques.

Abstract

Acaricidal activity of Uvaria versicolor and Uvaria klaineana (Annonaceae). Akendengue, B.; Ngou-Milama, E.; Bourobou-Bourobou, H.; Essouma, J.; Roblot, F.; Gleye, C.; Laurens, A.; Hocquemiller, R.; Loiseau, P.; Bories, C. Departement de Chimie-Biochimie, Faculte de Medecine et des Sciences de la Sante, Libreville, Gabon. Phytotherapy Research (2003), 17(4), 364-367. Publisher: John Wiley & Sons Ltd., CODEN: PHYREH ISSN: 0951-418X. Journal written in English. CAN 139:360378 AN 2003:430291 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A review discussing the detn. of flavanones, chalcones, and dihydrochalcones in plant and food anal. Abstract

Analysis and purification of flavanones, chalcones and dihydrochalcones. Tomas-Barberan, Francisco A.; Gil-Izquierdo, Angel; Ferreres, Federico; Gil, Maria I. Departamento de Ciencia y Tecnologia de Alimentos, CEBAS (CSIC), Murcia, Spain. Editor(s): Santos-Buelga, Celestino; Williamson, Gary. Methods in Polyphenol Analysis (2003), 359-371. Publisher: Royal Society of Chemistry, Cambridge, UK CODEN: 69DZBQ Conference; General Review written in English. CAN 140:144804 AN 2003:430347 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The formation of procyanidin and anthocyanin in grape cells is markedly increased by treatment with salicylic acid. The activity of phenylalanine ammonia-lyase and chalcone-flavanone isomerase increased in close relation to the formation of these phenolics. Salicylic acid-induced elevation of these enzyme activities occurred more rapidly than elevation induced by light irradn. In the cells, the phenolics were degraded in a different manner by salicylic acid treatment than that by light irradn. Salicylic acid might be used as a simple and effective stimulant for the formation of procyanidin as well as anthocyanin in large scale cultures of plant cells.

Abstract

Effects of salicylic acid on the production of procyanidin and anthocyanin in culture grape cells. Obinata, Noe; Yamakawa, Takashi; Takamiya, Mikiko; Tanaka, Norie; Ishimaru, Kanji; Kodama, Tohru. Dep. Biotechnol., The Univ. Tokyo, Tokyo, Japan. Plant Biotechnology (Tokyo, Japan) (2003), 20(2), 105-111. Publisher: Japanese Society for Plant Cell and Molecular Biology, CODEN: PLBIF6 ISSN: 1342-4580. Journal written in English. CAN 139:81999 AN 2003:450918 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Photochemical synthesis of 2,2'-biflavanones from flavone. Chen, Arh-Hwang; Kuo, Wei-Bao; Chen, Chia-Wen. Department of Chemistry, National Kaohsiung Normal University, Kaohsiung, Taiwan. Journal of the Chinese Chemical Society (Taipei, Taiwan) (2003), 50(1), 123-127. Publisher: Chinese Chemical Society, CODEN: JCCTAC ISSN: 0009-4536. Journal written in English. CAN 139:179641 AN 2003:405003 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Flavone synthases (FNSs) catalyze the oxidn. of flavanones to flavones, i.e., the formation of apigenin from (2S)-naringenin. While many plants express a microsomal-type FNS II, the sol. FNS I appears to be confined to a few species of the Apiaceae and was cloned recently from parsley plants. FNS I belongs to the FeII/2-oxoglutarate-dependent dioxygenases characterized by short conserved sequence elements for cofactor binding, and its evolutionary context and mode of action are under investigation. Using a homol.-based reverse transcription polymerase chain reaction approach, two addnl. flavonoid-specific dioxygenases were cloned from immature parsley leaflets, which were identified as flavanone 3β-hydroxylase (FHT) and flavonol synthase (FLS) after expression in yeast cells. Sequence alignments revealed marginal differences among the parsley FNS I and FHT polypeptides of only 6%, while much less identity (about 29%) was obsd. with the parsley FLS. Analogous to FNS I, FLS oxidizes the flavonoid γ-pyrone by introducing a C2,C3 double bond, and (2R,3S)-dihydrokaempferol (cis-dihydrokaempferol) was proposed recently as the most likely intermediate in both FNS I and FLS catalysis. Incubation of either FNS I or FLS with cis-dihydrokaempferol exclusively produced kaempferol and confirmed the assumption that flavonol formation occurs via hydroxylation at C3 followed by dehydration. However, the lack of apigenin in these incubations ruled out cis-dihydrokaempferol as a free intermediate in FNS I catalysis. Furthermore, neither (+)-trans-dihydrokaempferol nor unnatural (-)-trans-dihydrokaempferol and 2-hydroxynaringenin served as a substrate for FNS I. Overall, the data suggest that FNS I has evolved uniquely in some Apiaceae as a paraphyletic gene from FHT, irresp. of the fact that FNS I and FLS catalyze equiv. desatn. reactions.

Abstract

Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley. Martens, Stefan; Forkmann, Gert; Britsch, Lothar; Wellmann, Frank; Matern, Ulrich; Lukacin, Richard. Institut fuer Pharmazeutische Biologie, Philipps-Universitaet Marburg, Marburg, Germany. FEBS Letters (2003), 544(1-3), 93-98. Publisher: Elsevier Science B.V., CODEN: FEBLAL ISSN: 0014-5793. Journal written in English. CAN 139:193554 AN 2003:411677 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


From the stem bark of Erythrina burttii, a new isoflavone, 5,2',4'-trihydroxy-7-methoxy-6-(3-methylbut-2-enyl)isoflavone (trivial name, 7-O-methylluteone) and a new flavanone, 5,7-dihydroxy-4'-methoxy-3'-(3-methylbutadienyl)-5'-(3-methylbut-2-enyl)flavanone (trivial name, burttinonedehydrate) along with three known isoflavonoids (8-prenylluteone, 3-O-methylcalopocarpin and genistein) were isolated. The structures were detd. on the basis of spectroscopic evidence.

Abstract

Two prenylated flavonoids from the stem bark of Erythrina burttii. Yenesew, Abiy; Irungu, Beatrice; Derese, Solomon; Midiwo, Jacob O.; Heydenreich, Matthias; Peter, Martin G. Department of Chemistry, University of Nairobi, Nairobi, Kenya. Phytochemistry (Elsevier) (2003), 63(4), 445-448. Publisher: Elsevier Science Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:258094 AN 2003:414843 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

In plants, chalcones are precursors for a large no. of flavonoid-derived plant natural products and are converted to flavanones by chalcone isomerase or nonenzymically. Chalcones are synthesized from tyrosine and phenylalanine via the phenylpropanoid pathway involving phenylalanine ammonia lyase (PAL), cinnamate-4-hydroxylase (C4H), 4-coumarate:CoA ligase (4CL), and chalcone synthase (CHS). For the purpose of prodn. of flavanones in Escherichia coli, three sets of an artificial gene cluster which contained three genes of heterologous origins-PAL from the yeast Rhodotorula rubra, 4CL from the actinomycete Streptomyces coelicolor A3(2), and CHS from the licorice plant Glycyrrhiza echinata-were constructed. The constructions of the three sets were done as follows: (i) PAL, 4CL, and CHS were placed in that order under the control of the T7 promoter (PT7) and the ribosome-binding sequence (RBS) in the pET vector, where the initiation codons of 4CL and CHS were overlapped with the termination codons of the preceding genes; (ii) the three genes were transcribed by a single PT7 in front of PAL, and each of the three contained the RBS at appropriate positions; and (iii) all three genes contained both PT7 and the RBS. These pathways bypassed C4H, a cytochrome P 450 hydroxylase, because the bacterial 4CL enzyme ligated CoA to both cinnamic acid and 4-coumaric acid. E. coli cells contg. the gene clusters produced two

Abstract

Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster. Hwang, Eui Il; Kaneko, Masafumi; Ohnishi, Yasuo; Horinouchi, Sueharu. Department of Biotechnology, Graduate School of Agriculture and Life Sciences, The University of Tokyo, Tokyo, Japan. Applied and Environmental Microbiology (2003), 69(5), 2699-2706. Publisher: American Society for Microbiology, CODEN: AEMIDF ISSN: 0099-2240. Journal written in English. CAN 139:178740 AN 2003:377628 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The chem. components of Oxytropis falcata from petroleum ether have been studied by the GC-MS-DC, and 57 constituents have been identified. The major components are (z,z,z)-9, 12, 15-octadeca-trien-1-ol(14.73%), (E)-1-(2,6-dihydroxy-4-methoxyl)-3-phenyl-2-propen-1-one (7.68%), hexadecanoic acid ethylester(6.49%), linolenic acid ethylester (4.35%), 23,24-dihydro stigmasterol (4.30%), 2-phenyl-5,7-dihydroxy flavanone(1.93%) etc. The major components come up to 86.70%.

Abstract

GC-MS analysis of chemical component of Oxytropis falcata extracted by petroleum ether. Zheng, Shang-zhen; Que, Sheng; Xu, Xian-fang; Shen, Xu-wei. College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, Peop. Rep. China. Xibei Shifan Daxue Xuebao, Ziran Kexueban (2003), 39(2), 51-53. Publisher: Xibei Shifan Daxue, CODEN: XDXKEH ISSN: 1001-988X. Journal written in Chinese. CAN 140:117508 AN 2003:400848 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Photolysis of flavone (4) with the electron-donating amines including triethylamine or 2-(N,N-dimethylamino)ethanol in acetonitrile, benzene or methylene dichloride can easily afford two hydrodimers of 2,2'-biflavanone(racemate) (5a) and 2,2'-biflavanone(meso) (5b) and one reductive product of flavanone (6). Their yields were dependent on the molar ratios of substrate to amine, the kinds of amines, the solvents used and the irradn. sources. Higher yields were afforded 2,2'-biflavanone(racemate) (5a), 2,2'-biflavanone(meso) (5b) and flavanone (6) (30.0%, 20.9% and 15.8%, resp.) in the reaction condition of 1/2 molar ratio of flavone (4) to triethylamine in acetontrile with fourteen hours of irradn.

Abstract


flavanone

WO 2003040306 A3 20040219WO 2003040306 A2 20030515 WO 2002-NZ239 20021107Patent No. Kind Date Application No. Date Patent Family Information

Sequence homologs of genes for enzymes of structural macromolecule biosynthesis of forage grasses and their uses in altering forage composition. Demmer, Jeroen; Forster, Richard L.; Gibson, John Bryan; Shenk, Michael Andrew; Norriss, Michael Geoffrey; Glenn, Matthew; Saulsbury, Keith Martin; Hall, Claire. (Genesis Research and Development Corporation Limited, N. Z.; Wrightson Seeds Limited). PCT Int. Appl. (2003), 240 pp. CODEN: PIXXD2 WO 2003040306 A2 20030515 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SI, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2002-NZ239 20021107. Priority: US 2001-337703 20011107. CAN 138:380491 AN 2003:376999 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Epidemiol. evidence has suggested that consumption of fruit and vegetables reduces the risk of both cancer and cardiovascular diseases, potentially through the biol. actions of components such as vitamin C, vitamin E, flavonoids, and carotenoids. Citrus species are extremely rich sources in vitamin C and flavanones, a class of compds. which belongs to the flavonoids family. A comparison of the phenolic compns., the ascorbic acid contents and the antioxidant activities of fresh Sicilian orange juices from pigmented (Moro, Tarocco and Sanguinello) and non-pigmented (Ovale, Valencia and Navel) varieties of orange (Citrus sinensis L. Osbeck), was undertaken. The simultaneous characterization and quantification of the major flavanone, anthocyanin and hydroxycinnamate components were attained by HPLC with diode array detection. Differences between varieties in terms of the flavanone glycoside content, particularly hesperidin, were obsd., with the Tarocco juices reporting the highest content. Furthermore, cyanidin-3-glucoside and cyanidin-3-(6''-malonyl)-glucoside were predominant in all the pigmented varieties, but their concn. was higher in the juices of the Moro variety. Quant., the major antioxidant component of all juices was ascorbic acid and its concn. was significantly correlated (r = 0.74, P < 0.001) with the total antioxidant activity of the juices, detd. in vitro using the ABTS radical cation decolorization assay. Similarly, hydroxycinnamates (r = 0.73, P < 0.01) and anthocyanins (r = 0.98, P < 0.001) content showed a good correlation with the detd. antioxidant capacity. Therefore orange juices, particularly those rich in anthocyanins, may represent a significant dietary source of flavonoids.

Abstract

The compositional characterisation and antioxidant activity of fresh juices from Sicilian sweet orange (Citrus sinensis L. Osbeck) varieties. Proteggente, Anna R.; Saija, Antonella; De Pasquale, Anna; Rice-Evans, Catherine A. Antioxidant Research Group, Wolfson Centre for Age-Related Diseases, GKT School of Biomedical Sciences, King's College London, London, UK. Free Radical Research (2003), 37(6), 681-687. Publisher: Taylor & Francis Ltd., CODEN: FRARER ISSN: 1071-5762. Journal written in English. CAN 139:52025 AN 2003:377531 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanones, pinocembrin from phenylalanine and naringenin from tyrosine, in addn. to their precursors, cinnamic acid and 4-coumaric acid. Of the three sets, the third gene cluster conferred on the host the highest ability to produce the flavanones. This is a new metabolic engineering technique for the prodn. in bacteria of a variety of compds. of plant and animal origin.


flavanone

Previous studies have shown that flavonoids inhibit glucose uptake in cultured cells. In this report, we show that the grapefruit flavanone naringenin inhibited insulin-stimulated glucose uptake in 3T3-L1 adipocytes in a dose-dependent manner. Naringenin acts by inhibiting the activity of phosphoinositide 3-kinase (PI3K), a key regulator of insulin-induced GLUT4 translocation. Although naringenin did not alter the phosphotyrosine status of the insulin receptor, insulin receptor substrate proteins, or PI3K, it did inhibit the phosphorylation of the downstream signaling mol. Akt. In an in vitro kinase assay, naringenin inhibited PI3K activity. A physiol. attainable dose of 6 μM naringenin reduced insulin-stimulated glucose uptake by approx. 20%. This inhibitory effect remained 24 h after the removal of naringenin from the culture medium. Collectively, our findings suggest that the regular consumption of naringenin in grapefruit may exacerbate insulin resistance in susceptible individuals via impaired glucose uptake in adipose tissue.

Abstract

Naringenin inhibits phosphoinositide 3-kinase activity and glucose uptake in 3T3-L1 adipocytes. Harmon, Anne W.; Patel, Yashomati M. Department of Nutrition, University of North Carolina School of Public Health, Chapel Hill, NC, USA. Biochemical and Biophysical Research Communications (2003), 305(2), 229-234. Publisher: Elsevier Science, CODEN: BBRCA9 ISSN: 0006-291X. Journal written in English. CAN 139:95198 AN 2003:363859 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Sequence homologs of genes for enzymes of lignin, fructan and tannin biosynthesis are identified in the forage grasses Lolium perenne and Festuca arundinacea. The genes may be used as targets in the modulation of patterns of macromol. biosynthesis and the nutritional compn. and value of forage grasses (no data). Candidate genes were identified in leaf and stem expression libraries by BLAST searching against public sequence databases. Candidate genes for sucrose phosphatase, sucrose synthase, acid invertase and peroxidase were shown to encode the enzymes by assay of gene products in Escherichia coli or Pchia pastoris. Candidate fructosyltransferase genes were tested for their effects on fructan compn. of Nicotiana benthamiana.

Abstract WO 2002-NZ239 W 20021107US 2001-337703P P 20011107Priority Application NZ 532712 A 20061222 NZ 2002-532712 20021107


EP 1451327 A2 20040901 EP 2002-795456 20021107AU 2002360228 B2 20080410AU 2002360228 A1 20030519 AU 2002-360228 20021107CA 2465917 A1 20030515 CA 2002-2465917 20021107

RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SC, SD, SE, SG, SI, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW


flavanone

Metab. of 7-O-methylnaringenin (sakuranetin, I) by Cunninghamella elegans NRRL 1392 yielded naringenin and naringenin-4'-sulfate. C. elegans also converted 5,3',4'-trihydroxy-7-methoxyflavanone (7-methyleriodictyol, II) into eriodictyol-4'-sulfate. Furthermore, incubation of 5,4'-dihydroxy-7,3'-dimethoxyflavanone (III) with the same fungus gave homoeriodictyol (5,7,4'-trihydroxy-3'-methoxyflavanone) and homoeriodicytol-7-sulfate. The structures of the new metabolites were established by spectral anal. including 2D-NMR, HR-ESI-FT-MS beside hydrolysis by acid.

Abstract

O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans. Abdel-Rahim, Sayed Ibrahim; Galal, Ahmed Mohamed; Ahmed, Mohammed Shamim; Mossa, Gabir Salem. Pharmacognosy Department, College of Pharmacy, Tanta University, Tanta, Egypt. Chemical & Pharmaceutical Bulletin (2003), 51(2), 203-206. Publisher: Pharmaceutical Society of Japan, CODEN: CPBTAL ISSN: 0009-2363. Journal written in English. CAN 140:4098 AN 2003:355011 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effect of hesperetin, naringenin and its glycoside form on the Sindbis neurovirulent strain (NSV) replication in vitro was studied. All flavanones tested were not cytotoxic on Baby Hamster cells 21 clone 15 (BHK-21). Antiviral effect was evaluated by a colorimetric assay using MTT (3-(4,5 dimethylthiazol-2-yl)-2,5-dipheyl-tetrazolium bromide) and by plaque redn. assay. Hesperetin and naringenin had inhibitory activity on NSV infection. The 50% inhibitory doses (ID50%) of both compds. were 20.5 and 14.9 μg/mL resp., as established by plaque assay. However their glycosides, hesperidin and naringin did not have inhibitory activity. Implying that the presence of rutinose moiety of flavanones blocks the antiviral effect. Oxygenation on the 3' positions at the B rings on the hesperetin skeleton decrease the anti viral activity at 25 μg/mL.

Abstract

Anti-sindbis activity of flavanones hesperetin and naringenin. Paredes, Adriana; Alzuru, Mariaelena; Mendez, Jeannette; Rodriguez-Ortega, Morella. Biomedical Institute, Venezuelan Central University, Caracas, Venez. Biological & Pharmaceutical Bulletin (2003), 26(1), 108-109. Publisher: Pharmaceutical Society of Japan, CODEN: BPBLEO ISSN: 0918-6158. Journal written in English. CAN 139:173242 AN 2003:363084 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Activity-guided fractionation of an EtOAc-sol. ext. of the leaves of Muntingia calabura collected in Peru, using an in vitro quinone reductase induction assay with cultured Hepa 1c1c7 (mouse hepatoma) cells, resulted in the isolation of a flavanone with an unsubstituted B-ring, (2R,3R)-7-methoxy-3,5,8-trihydroxyflavanone, as well as 14 known compds., which were mainly flavanones and

Abstract

Activity-guided isolation of the chemical constituents of Muntingia calabura using a quinone reductase induction assay. Su, Bao-Ning; Park, Eun Jung; Vigo, Jose Schunke; Graham, James G.; Cabieses, Fernando; Fong, Harry H. S.; Pezzuto, John M.; Kinghorn, A. Douglas. College of Pharmacy, Program for Collaborative Research in the Pharmaceutical Sciences and Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL, USA. Phytochemistry (Elsevier) (2003), 63(3), 335-341. Publisher: Elsevier Science Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:176139 AN 2003:345378 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


O

OH O

O

O

O

OH O

O

O

O

OH O

O

O

Me

H

Me

H

OH

Me

H

OMe

I

III

II


flavanone

Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a satd. three carbon Abstract

Dihydrochalcones: Evaluation as Novel Radical Scavenging Antioxidants. Nakamura, Yoshimasa; Watanabe, Shigeo; Miyake, Nobuyuki; Kohno, Hiroyuki; Osawa, Toshihiko. Laboratory of Food and Biodynamics Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya, Japan. Journal of Agricultural and Food Chemistry (2003), 51(11), 3309-3312. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 139:30718 AN 2003:322574 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


From the roots of Deguelia hatschbachii, the known flavonoids scandenin (I), Me robustate (II) and 4',5-dihydroxy-6-(3,3-dimethylalyll)-7-methoxy flavanone (III) were isolated and characterized by comparison of their spectroscopic data with those found in the literature. Now the inclusion of 1D- and 2D-NMR and MS/MS data has allowed the complete assignment of all hydrogen and carbon chem. shifts in their NMR spectra, as well as the elucidation of the fragmentation pathways of I-III in the mass spectrometer.

Abstract

New spectral data of some flavonoids from Deguelia hatschbachii A.M.G. Azevedo. Magalhaes, Aderbal F.; Tozzi, Ana M. G. A.; Magalhaes, Eva G.; Moraes, Valeria R. de S. Instituto de Quimica, Universidade Estadual de Campinas, CP 6154, Campinas - SP, Brazil. Journal of the Brazilian Chemical Society (2003), 14(1), 133-137. Publisher: Sociedade Brasileira de Quimica, CODEN: JOCSET ISSN: 0103-5053. Journal written in English. CAN 139:130617 AN 2003:325780 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Several flavones and flavanones were isolated from chloroform extd. air-dried South American Cunila species. The flavonoid aglycons accumulation was obsd. mainly in C. incana, C. angustifolia and C. incisa.

Abstract

Flavones and flavanones from South American Cunila species. de Loreto Bordignon, S. A.; Montanha, J. A.; Schenkel, E. P. Curso de Biologia, Universidade Luterana do Brasil, Canoas, Brazil. Biochemical Systematics and Ecology (2003), 31(7), 785-788. Publisher: Elsevier Science Ltd., CODEN: BSECBU ISSN: 0305-1978. Journal written in English. CAN 140:38766 AN 2003:325973 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavones. The structure including abs. stereochem. of compd. 5 was detd. by spectroscopic (HRMS, 1D and 2D NMR, and CD spectra) methods. Of the isolates obtained, in addn. to 5, (2S)-5-hydroxy-7-methoxyflavanone, 2',4'-dihydroxychalcone, 4,2',4'-trihydroxychalcone, 7-hydroxyisoflavone and 7,3',4'-trimethoxyisoflavone were found to induce quinone reductase activity.


flavanone

Genes encoding flavonoid biosynthesis enzymes in white clover and perennial ryegrass and their use in genetic Bibliographic Information Answer 946:

Some new 3,5-diaryl-4-aroyl-1-benzoyl-Δ2-pyrazolines were synthesized by the action of benzhydrazide on 3-aroyl flavanones in pyridine medium. Structure of these compds. was established on the basis of spectral anal. and elemental anal.

Abstract

Synthesis of 3,5 diaryl-4-aroyl-1-benzoyl-Δ2-pyrazolines. Jaware, Miss K. N.; Ganorkar, Rajesh P.; Jamode, V. S. Department of Chemistry, Amravati University, Amravati, India. Asian Journal of Chemistry (2003), 15(2), 833-836. Publisher: Asian Journal of Chemistry, CODEN: AJCHEW ISSN: 0970-7077. Journal written in English. CAN 139:214382 AN 2003:310744 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The effect of several solvents on the heterogeneous synthesis of flavanone from benzaldehyde and 2-hydroxyacetophenone over a solid MgO catalyst was examd. exptl. through kinetic and FTIR spectroscopic studies. High-boiling-point solvents considered were DMSO, tetralin, mesitylene, benzonitrile, and nitrobenzene. Kinetic results indicate that the presence of different solvents in this reaction system affects the rate, kinetic dependencies, and selectivities toward flavanone and 2'-hydroxychalcone. DMSO in particular, significantly promotes the rates of both steps used in this synthesis (i.e., the Claisen-Schmidt condensation reaction of benzaldehyde with 2-hydroxyacetophenone and the subsequent isomerization of the 2'-hydroxychalcone intermediate to flavanone). The effect is more pronounced for the second reaction. Even the presence of small amts. of DMSO in other solvents, such as benzonitrile and nitrobenzene, results in strong promotion of the flavanone synthesis scheme. Results of FTIR spectroscopic studies indicate that the interaction of MgO with DMSO gave stable surface sulfate species. The presence of these species on the catalyst surface affects the adsorption behavior of benzaldehyde and 2-hydroxyacetophenone.

Abstract

The effect of solvents on the heterogeneous synthesis of flavanone over MgO. Drexler, Michele T.; Amiridis, Michael D. Department of Chemical Engineering, University of South Carolina, Columbia, SC, USA. Journal of Catalysis (2003), 214(1), 136-145. Publisher: Elsevier Science, CODEN: JCTLA5 ISSN: 0021-9517. Journal written in English. CAN 139:68822 AN 2003:313155 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


bridge. In the present study, the authors systematically examd. the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidn. in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The 1H NMR anal. indicated that the active dihydrochalcone has a time-averaged conformation in which the arom. A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by redn. of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential. The results are discussed in relation to the use of dihydrochalcones as pharmaceuticals and food additives.


flavanone


The present invention relates to nucleic acids and nucleic acid fragments encoding amino acid sequences for flavonoid biosynthetic enzymes in plants, and the use thereof for the modification of flavonoid biosynthesis in plants. More particularly, the flavonoid biosynthetic enzyme is selected from the group consisting of chalcone isomerase, chalcone synthase, chalcone reductase, dihydroflavonol 4-reductase, leucoanthocyanidin reductase, flavonoid 3',5'-hydrolase, flavanone 3-hydroxylase, flavonoid 3'-hydroxylase, phenylalanine ammonia-lyase, and vestitone reductase, found in white clover (Trifolium repens) and perennial ryegrass (Lolium perenne).

Abstract WO 2002-AU1345 W 20021004AU 2001-8113 A 20011005Priority Application US 20050069884 A1 20050331 US 2004-491823 20041025 NZ 531985 A 20060127 NZ 2002-531985 20021004


EP 1442122 A1 20040804 EP 2002-800506 20021004AU 2002333038 B2 20080207AU 2002333038 A1 20030422 AU 2002-333038 20021004CA 2461058 A1 20030417 CA 2002-2461058 20021004

RW: GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW, AM, AZ, BY, KG, KZ, MD, RU, TJ, TM, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, SK, TR, BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG

W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW

WO 2003031622 A1 20030417 WO 2002-AU1345 20021004Patent No. Kind Date Application No. Date Patent Family Information

manipulation of flavonoid biosynthesis in plants. Spangenberg, German; Sawbridge, Timothy Ivor; Ong, Eng Kok; Emmerling, Michael. (Agriculture Victoria Services Pty. Ltd., Australia; Agresearch Limited). PCT Int. Appl. (2003), 732 pp. CODEN: PIXXD2 WO 2003031622 A1 20030417 Designated States W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, OM, PH, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW. Designated States RW: AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE, TR, BF, BJ, CF, CG, CI, CM, GA, ML, MR, NE, SN, TD, TG. Patent written in English. Application: WO 2002-AU1345 20021004. Priority: AU 2001-8113 20011005. CAN 138:298914 AN 2003:301224 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Flavonoids, phenolic acids and abscisic acid of Australian and New Zealand Leptospermum honeys were analyzed by HPLC. Fifteen flavonoids were isolated in Australian jelly bush honey (Leptospermum polygalifolium), with an av. content of 2.22 mg/100 g honey. Myricetin (3,5,7,3',4',5'-hexahydroxyflavone), luteolin (5,7,3',4'-tetrahydroxyflavone) and tricetin (5,7,3',4',5'-pentahydroxyflavone) were the main flavonoids identified. The mean content of total phenolic acids in jelly bush honey was 5.14 mg/100 g honey, with gallic and coumaric acids as the potential phenolic acids. Abscisic acid was quantified as twice the amt. (11.6 mg/100 g honey) of the phenolic acids in this honey. The flavonoid profile mainly consisted of quercetin (3,5,7,3',4'-pentahydroxyflavone), isorhamnetin

Abstract

Flavonoids, phenolic acids and abscisic acid in Australian and New Zealand Leptospermum honeys. Yao, Lihu; Datta, Nivedita; Tomas-Barberan, Francisco A.; Ferreres, Federico; Martos, Isabel; Singanusong, Riantong. School of Land and Food Sciences, Food Science and Technology, The University of Queensland, Gatton, Australia. Food Chemistry (2003), 81(2), 159-168. Publisher: Elsevier Science Ltd., CODEN: FOCHDJ ISSN: 0308-8146. Journal written in English. CAN 138:320239 AN 2003:264789 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Br

HO

Br

OH

CO CH S C

SBu

O

O

Br

Br

HO Ph

Bu

NR 1R2

R1

I

II

Thermal stability and biol. activity of some N,N-dialkyl dithiocarbamates (I) and corresponding flavanones (II) were evaluated. The biol. activity tests were conducted on wheat (Triticum aestivum) and a medicinal plant Stachys sieboldii, as well as on several species of bacteria. Several compds. showed germination and plant growth inhibiting and/or stimulating activities at different concns., as well as antibacterial properties.

Abstract

Study of the thermal stability and biological activity of phenacyl N,N-dialkyl dithiocarbamates and the corresponding flavanones. Finaru, Adriana; Grosu, Mirela; Prisecaru, Maria; Segal, Eugen. Universite De Bacau, Laboratoire de Synthese Organique et Analyse Structurale, Bacau, Rom. Studii si Cercetari Stiintifice: Chimie si Inginerie Chimica, Biotehnologii, Industrie Alimentara (Universitatea Bacau) (2002), 3(1-2), 65-70. Publisher: University of Bacau, Dep. of Chemistry and Food Science & Technology, CODEN: SCSCC6 ISSN: 1582-540X. Journal written in French. CAN 140:37366 AN 2003:265355 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

The main objective of this EU project is the study of natural defense mechanisms of pome fruit against fire blight, a disease of relevant importance in several rosaceous species all over the world and quite recently in Italy. The recent outbreaks of the disease in Italy as well as the situation in other European countries justify the attention given by several research institutions to face this disease. A multidisciplinary approach was chosen to achieve the objective of the project including horticultural, bacteriol., biochem., and mol. biol. methods. The goals partially achieved by the project partners concern the availability of dioxygenase inhibitors, of plant material susceptible and tolerant to Erwinia amylovora to test, of preliminary results of practical applications on pome fruit species and varieties and the involvement of some flavonoids involved in defense reactions vs. Erwinia amylovora. The most significant results

Abstract

Induction of pathogen resistance in pear by transiently altering the flavonoid metabolism with specific enzyme inhibitors. Stich, K.; Halbwirth, H.; Kampan, W.; Treutter, D.; Rommelt, S.; Peterek, S.; Forkmann, G.; Fisher, T. C.; Martens, S.; Meisel, B.; Costa, G.; Andreotti, C.; Sabatini, E.; Bazzi, C.; Rademacher, W. Institute of Applied Botany, Technical University of Vienna, Austria. Acta Horticulturae (2002), 596(Vol. 1, Proceedings of the VIIIth International Symposium on Pear, 2000, Volume 1), 513-521. Publisher: International Society for Horticultural Science, CODEN: AHORA2 ISSN: 0567-7572. Journal written in English. CAN 139:114514 AN 2003:252803 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


Orange juice manufd. on an industrial scale was subjected to digestion under in vitro gastrointestinal conditions (pH, temp., and enzyme and chem. conditions) to evaluate the influence of individual industrial processing treatments on flavanone soly., stability, and ability to permeate through a membrane under simulated physiol. conditions. Four industrial processes including squeezing, std. pasteurization, concn., and freezing were evaluated. Hand squeezing was compared with industrial squeezing. After in vitro gastrointestinal digestion of the orange juices, the flavanones able to permeate through a dialysis membrane, and those remaining in the retentate were evaluated by HPLC as were those present in the insol. fraction. In all of the assayed orange juices, a high content of pptd. chalcones (≈70% of the total flavanones) was formed under the physiol. conditions of the gastrointestinal tract. Hand squeezing provided a higher concn. of flavanones in the permeated fraction and lower transformation to chalcones than industrial squeezing. Std. pasteurization did not influence the soly. and permeability of the orange juice flavanones and chalcones. Industrial concn. did not affect the amt. of flavanones able to permeate but decreased the chalcones produced. Juices produced from frozen orange juice contained considerably smaller amts. of both sol. flavanones and insol. chalcones.

Abstract

Influence of Industrial Processing on Orange Juice Flavanone Solubility and Transformation to Chalcones under Gastrointestinal Conditions. Gil-Izquierdo, Angel; Gil, Maria Isabel; Tomas-Barberan, Francisco Abraham; Ferreres, Federico. Research Group on Quality, Safety and Bioactivity of Plant Foods, Departamento Ciencia y Tecnologia de Alimentos, CEBAS-CSIC, Murcia, Spain. Journal of Agricultural and Food Chemistry (2003), 51(10), 3024-3028. Publisher: American Chemical Society, CODEN: JAFCAU ISSN: 0021-8561. Journal written in English. CAN 139:6032 AN 2003:263862 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


(3,5,7,4'-tetrahydroxyflavone 3'-Me ethyl), chrysin (5,7-dihydroxyflavone), luteolin and an unknown flavanone in New Zealand manuka (Leptospermum scoparium) honey with an av. content of total flavonoids of 3.06 mg/100 g honey. The content of total phenolic acids was up to 14.0 mg/100 g honey, with gallic acid as the main component. A substantial quantity (32.8 mg/100 g honey) of abscisic acid was present in manuka honey. These results showed that flavonoids and phenolic acids could be used for authenticating honey floral origins, and abscisic acid may aid in this authentication.


flavanone

Answer 953:

Two types of anthocyanins are formed in tissues of Zea mays (maize), the common 3-hydroxyanthocyanins and the rare 3-deoxyanthocyanins. Their formation is generally controlled by independent regulatory genes. Whereas the formation of 3-hydroxyanthocyanins is well established, the enzymes involved in the biosynthesis of the 3-deoxyanthocyanins remained unclear for a long time. In order to elucidate the key reaction involved, the redn. of flavanones to flavan 4-ols, dihydroflavonol 4-reductase (DFR) and flavanone 4-reductase (FNR) activities were investigated using enzyme prepns. from silks of different maize lines as well as from transgenic petunia and yeast, resp., expressing the A1 gene of maize. This gene is known to encode DFR. DFR and FNR activities could not be sepd. by biochem. investigations and the use of different enzyme inhibitors. In maize genotypes with recessive alleles (a1a1) of the A1 gene, neither DFR nor FNR activity was present. Moreover, heterologous expression of A1 in petunia and yeast has shown that the gene encodes for a reductase, which is able to convert both dihydroflavonols (DFR activity) and flavanones (FNR activity) to flavan 3,4-diols and flavan 4-ols, resp. Thus, DFR and FNR activities are provided by one and the same enzyme with a broad substrate acceptance, which even includes the 5-deoxydihydroflavonols. Further studies suggested that the anthocyanin type formed in the silks essentially depends on the strength of flavanone 3-hydroxylase activity.

Abstract

Biochemical formation of anthocyanins in silk tissue of Zea mays. Halbwirth, Heidrun; Martens, Stefan; Wienand, Udo; Forkmann, Gert; Stich, Karl. Institute for Technical BioScience, Technical University of Vienna, Vienna, Austria. Plant Science (Shannon, Ireland) (2003), 164(4), 489-495. Publisher: Elsevier Science Ireland Ltd., CODEN: PLSCE4 ISSN: 0168-9452. Journal written in English. CAN 139:130646 AN 2003:249474 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


To clarify the structure-activity relationships of flavonoids for nitric oxide (NO) prodn. inhibitory activity, we examd. the inhibitory effects of 73 flavonoids on NO prodn. in lipopolysaccharide-activated mouse peritoneal macrophages. Among those flavonoids, apigenin (IC50=7.7 μM), diosmetin (8.9 μM), and tetra-O-methylluteolin (2.4 μM), and hexa-O-methylmyricetin (7.4 μM) were found to show potent inhibitory activity, and the results suggested the following structural requirements of flavonoids: (1) the activities of flavones were stronger than those of corresponding flavonols; (2) the glycoside moiety reduced the activity; (3) the activities of flavones were stronger than those of corresponding flavanones; (4) the flavones and flavonols having the 4'-hydroxyl group showed stronger activities than those lacking the hydroxyl group at the B ring and having the 3',4'-dihydroxyl group; (5) the flavonols having the 3',4'-dihydroxyl group (catechol type) showed stronger activities than those having the 3',4',5'-trihydroxyl group (pyrogallol type); (6) the 5-hydroxyl group tended to enhance the activity; (7) methylation of the 3-, 5-, or 4'-hydroxyl group enhanced the activity; (8) the activities of isoflavones were weaker than those of corresponding flavones; (9) methylation of the 3-hydroxyl group reduced the cytotoxicity. In addn., potent NO prodn. inhibitors were found to inhibit induction of inducible nitric oxide synthase (iNOS) without iNOS enzymic inhibitory activity.

Abstract

Structural Requirements of Flavonoids for Nitric Oxide Production Inhibitory Activity and Mechanism of Action. Matsuda, Hisashi; Morikawa, Toshio; Ando, Shin; Toguchida, Iwao; Yoshikawa, Masayuki. Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Japan. Bioorganic & Medicinal Chemistry (2003), 11(9), 1995-2000. Publisher: Elsevier Science Ltd., CODEN: BMECEP ISSN: 0968-0896. Journal written in English. CAN 139:173163 AN 2003:251385 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


obtained up to now are presented here.


flavanone

Anastatins A and B, new skeletal flavonoids with hepatoprotective activities from the desert plant Anastatica hierochuntica. Yoshikawa, Masayuki; Xu, Fengming; Morikawa, Toshio; Ninomiya, Kiyofumi; Matsuda, Hisashi. Kyoto Pharmaceutical University, Yamashina-ku, Kyoto, Japan. Bioorganic & Medicinal Chemistry Letters (2003), 13(6), 1045-1049. Publisher: Elsevier Science


Treatment with the dioxygenase inhibitor prohexadione-Ca leads to major changes in the flavonoid metab. of apple (Malus domestica) and pear (Pyrus communis) leaves. Accumulation of unusual 3-deoxyflavonoids is obsd., which have been linked to an enhanced resistance toward fire blight. The committed step in this pathway is the redn. of flavanones. Crude exts. from leaves are able to perform this reaction. There was previous evidence that DFR enzymes of certain plants possess addnl. flavanone 4-reductase (FNR) activity. Such an FNR activity of DFR enzymes is proved here by heterologous expression of the enzymes. The heterologously expressed DFR/FNR enzymes of Malus and Pyrus possess distinct differences in substrate specificities despite only minor differences of the amino acid sequences. Kinetic studies showed that dihydroflavonols generally are the preferred substrates. However, with the obsd. substrate specificities the occurrence of 3-deoxyflavonoids in vivo after application of prohexadione-Ca can be explained.

Abstract

Molecular cloning, substrate specificity of the functionally expressed dihydroflavonol 4-reductases from Malus domestica and Pyrus communis cultivars and the consequences for flavonoid metabolism. Fischer, Thilo C.; Halbwirth, Heidrun; Meisel, Barbara; Stich, Karl; Forkmann, Gert. TUM Weihenstephan, Freising, Germany. Archives of Biochemistry and Biophysics (2003), 412(2), 223-230. Publisher: Elsevier Science, CODEN: ABBIA4 ISSN: 0003-9861. Journal written in English. CAN 139:129726 AN 2003:226528 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


This study characterized the chem. responses of Eucalyptus globulus and Eucalyptus nitens to artificial inoculation with a basidiomycete decay fungus. Nine-year-old trees responded to mech. wounding or inoculation with the decay fungus by producing new wound wood characterized by the presence of dark extractives 17 mo after wounding. Anal. of crude wound wood exts. by HPLC coupled to neg. ion electrospray mass spectrometry revealed the presence of a complex mixt. of many unidentified formylated phloroglucinol compds. (FPCs), in addn. to a diverse range of other polyphenolic compds. (hydrolyzable tannins, proanthocyanidins, flavanone glycoside, stilbene glycosides). Prior to this study, FPCs have only been reported from leaves and buds of Eucalyptus spp. Unequivocal evidence for the presence of macrocarpal A and B, and sideroxylonal A and B in the crude exts. was obtained, as well as evidence for a wide range of as yet unreported FPCs. Subsequent preliminary in vitro fungal and bacterial bioassays did not support an antimicrobial role for FPCs in host-pathogen interactions in eucalypts.

Abstract

Novel detection of formylated phloroglucinol compounds (FPCs) in the wound wood of Eucalyptus globulus and E. nitens. Eyles, Alieta; Davies, Noel W.; Mohammed, Caroline. Co-Operative Research Centre for Sustainable Production Forestry, Tasmania, Australia. Journal of Chemical Ecology (2003), 29(4), 881-898. Publisher: Kluwer Academic/Plenum Publishers, CODEN: JCECD8 ISSN: 0098-0331. Journal written in English. CAN 139:130728 AN 2003:239081 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))



flavanone

Reversed-phase HPLC determination of mangiferin, isomangiferin and hesperidin in Cyclopia and the effect of harvesting date on the phenolic composition of C. genistoides. Joubert, Elizabeth; Otto, Frank; Gruener, Sabine; Weinreich, Bernd. ARC Infruitec-Nietvoorbij, The Fruit Vine and Wine Institute of the Agricultural Research Council, Stellenbosch, S. Afr. European Food


The title flavanone deriv. was prepd. from phloroacetophenone in a multistep synthesis. All the products were characterized using spectral data and microanal.

Abstract

Synthesis of 5,7-dihydroxy-6,8-diprenyl-4'-O-prenylflavanone. Hossain, M. Amzad. Chemistry Division, Atomic Energy Centre, Dhaka, Bangladesh. Bangladesh Journal of Scientific and Industrial Research (1999), 34(3-4), 466-470. Publisher: Bangladesh Council of Scientific and Industrial Research, CODEN: BJSIBL ISSN: 0304-9809. Journal written in English. CAN 139:381343 AN 2003:204924 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A new antifungal flavanone, muscanone (1), was isolated along with known naringenin (2) from Commiphora wightii (Arn.) Bhandari (Burseraceae) by directing the fractionation of an EtOH ext. of the air-dried trunk of C. wightii with microbial sensitivity assay. The structures of 1 and 2 were detd. from EIMS, HREIMS, DEPT, 1H-1H COSY, HSQC and HMBC spectral data. Muscanone (1) was identified as 3-O-(1'',8'',14''-trimethylhexadecanyl)naringenin and was found to be active against Candida albicans. The isolation, structure elucidation, NMR spectral assignments, and bioactivities of 1 and 2 are reported.

Abstract

Muscanone: a 3-O-(1'',8'',14''-trimethylhexadecanyl)naringenin from Commiphora wightii. Fatope, Majekodunmi O.; Al-Burtomani, Suad Khamis S.; Ochei, John O.; Abdulnour, Abdulrahman O.; Al-Kindy, Salma M. Z.; Takeda, Yoshio. College of Science, Department of Chemistry, Sultan Qaboos University, Muscat, Oman. Phytochemistry (Elsevier) (2003), 62(8), 1251-1255. Publisher: Elsevier Science Ltd., CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 139:82015 AN 2003:212162 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


New skeletal flavonoids, anastatins A and B, were isolated from the methanolic ext. of an Egyptian medicinal herb, the whole plants of Anastatica hierochuntica. Their flavanone structures having a benzofuran moiety were detd. on the basis of chem. and physicochem. evidence. Anastatins A and B were found to show hepatoprotective effects on D-galactosamine-induced cytotoxicity in primary cultured mouse hepatocytes and their activities were stronger than those of related flavonoids and com. silybin.

Abstract

B.V., CODEN: BMCLE8 ISSN: 0960-894X. Journal written in English. CAN 139:154654 AN 2003:215763 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Citrus limonoid and flavonone glucosides demonstrated potential benefits to reduce risks of cancer and cardiovascular diseases. Citrus molasses obtained from waste residue has been used for animal feed. Since large concn. of glucosides of limonoid and

Abstract

Utilization of citrus by-products to improve human health. Raman, Girija; Ananthkrishnan, S.; Poulose, Shibu; Patil, Bhimanagouda S. Citrus Center, Texas A&M University-Kingsville, Weslaco, TX, USA. Abstracts of Papers, 225th ACS National Meeting, New Orleans, LA, United States, March 23-27, 2003 (2003), AGFD-108. Publisher: American Chemical Society, Washington, D. C CODEN: 69DSA4 Conference; Meeting Abstract written in English. AN 2003:178621 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The hot water and 70% ethanol exts. of dried mad-dog skullcap (Scutellaria lateriflora) both bound to the 5-HT7 receptor, with 87.2±6.2% and 56.7±1.3% inhibition of [3H]-LSD binding to the receptor at 100 μg/mL, resp. The online anal. of a 70% ethanol ext. by HPLC-UV/MS resulted in the identification of five flavones. Fractionation of the ethanol ext. resulted in the isolation of three flavone-glucuronides and a flavanone-glucuronide (9), including one new compd., lateriflorin (5,6,-dihydroxy-7-glucuronyloxy-2'-methoxyflavone) (8). The structure of 8 was detd. by NMR (1H NMR, 13C NMR, and NOESY expts.) and MS anal. From the results obtained in the testing of the pure compds., it is evident that the activity on the 5-HT7 receptor is at least partly due to the presence of flavonoids. Scutellarin and ikonnikoside I showed the highest inhibition of [3H]-LSD binding with IC50 values of 63.4 and 135.1 μM, resp.

Abstract

Inhibition of [3H]-LSD Binding to 5-HT7 Receptors by Flavonoids from Scutellaria lateriflora. Gafner, Stefan; Bergeron, Chantal; Batcha, Laura L.; Reich, Jesse; Arnason, John T.; Burdette, Joanna E.; Pezzuto, John M.; Angerhofer, Cindy K. Tom's of Maine, Kennebunk, ME, USA. Journal of Natural Products (2003), 66(4), 535-537. Publisher: American Chemical Society, CODEN: JNPRDF ISSN: 0163-3864. Journal written in English. CAN 138:348628 AN 2003:199720 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


A reversed-phase HPLC method for sepn. of polyphenols in honeybush tea (Cyclopia spp.) is presented. Sepn. of eriodictyol, luteolin, medicagol, formononetin, mangiferin, isomangiferin, hesperetin and hesperidin was investigated. A C12 stationary phase was required to sep. mangiferin and isomangiferin. The method was used to quantify the 3 major polyphenols (mangiferin, isomangiferin and hesperidin) in C. genistoides, C. intermedia, C. maculata and C. sessiliflora and to study the effect of harvesting date on these compds. in 2 types of C. genistoides. The highest levels of the xanthones, mangiferin (3.61 g/100 g) and isomangiferin (0.54 g/100 g), and the flavanone, hesperidin (1.74 g/100 g), were found for C. genistoides (both xanthones) and C. intermedia, resp. Cyclopia sessiliflora contained the lowest levels of mangiferin (1.04 g/100 g) and hesperidin (0.29 g/100 g). The mangiferin content of both the Overberg and West Coast types decreased with harvesting date. The Overberg type contained more mangiferin, but hesperidin was more prominent in the West Coast type.

Abstract

Research and Technology (2003), 216(3), 270-273. Publisher: Springer-Verlag, CODEN: EFRTFO ISSN: 1438-2377. Journal written in English. CAN 139:35283 AN 2003:200090 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavanone

Answer 963:

A review on identification of hair growth-promoting astilbin from Hypericum perforatum, structure-activity relationship of astilbin, synthesis and hair growth promoting effect of astilbin analog trans-3,4-dimethyl-3-hydroxyflavanone (t-flavanone), and application of t-flavanone-contg. hair prepns. to androgenetic alopecia.

Abstract

Effect of t-flavanone on hair growth. Hotta, Mitsuyuki; Imokawa, Genji. Biological Science Laboratories, Kao Corporation, Tochigi, Japan. Fragrance Journal (2003), 31(2), 33-40. Publisher: Fureguransu Janaru Sha, CODEN: FUJAD7 ISSN: 0288-9803. Journal; General Review written in Japanese. CAN 138:390502 AN 2003:163783 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


The MultiCASE expert system was used to construct a quant. structure-activity relationship model to screen chems. with estrogen receptor (ER) binding potential. Structures and ER binding data of 313 chems. were used as inputs to train the expert system. The training data set covers inactive, weak as well as very powerful ER binders and represents a variety of chem. compds. Substructural features assocd. with ER binding activity (biophores) and features that prevent receptor binding (biophobes) were identified. Although a single phenolic hydroxyl group was found to be the most important biophore responsible for the estrogenic activity of most of the chems., MultiCASE also identified other biophores and structural features that modulate the activity of the chems. Furthermore, the findings supported the authors' previous hypothesis that a 6 A distant descriptor may describe a ligand-binding site on an ER. Quant. structure-activity relationship models for the chems. assocd. with each biophore were constructed as part of the expert system and can be used to predict the activity of new chems. The model was cross validated via 10×10%-off tests, giving an av. concordance of 84.04%.

Abstract

Structure-activity relationship study of a diverse set of estrogen receptor ligands (I) using MultiCASE expert system. Klopman, Gilles; Chakravarti, Suman K. Department of Chemistry, Case Western Reserve University, Cleveland, OH, USA. Chemosphere (2003), 51(6), 445-459. Publisher: Elsevier Science Ltd., CODEN: CMSHAF ISSN: 0045-6535. Journal written in English. CAN 139:129225 AN 2003:166165 CAPLUS (Copyright (C) 2008 ACS on SciFinder (R))


flavonone are present in citrus byproducts, our goal was to isolate functional components from byproducts of citrus for potential health promoting properties. Due to the structural similarity of the glucosides of flavonone and limonoids, isolation of the pure glucosides from the mixt. was tedious. A rapid sepn. technique using a combination of adsorption chromatog. and flash chromatog. was designed to isolate these compds. from the mixt. of glucosides. The citrus molasses was de-pectinised and passed through ion-exchange resins to obtain an ext. rich in glucosides. This enriched ext. was agitated under cold conditions to sep. the glucosides, which are present in max. concn. The freeze-dried ext. was further sepd. using flash chromatog. technique. A small four-step gradient method using acetonitrile and water as mobile phase was developed. Structurally similar glucosides may be sepd. to the extent of 85%. This system can be used as a rapid technique for sepn. of closely related limonoid and flavanone glucosides. This isolation technique would be useful to isolate and purify the minor fractions of functional components in a larger quantity. Furthermore, larger quantity of minor fraction would be useful to establish structural relation with biol. activity.


flavanone

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