Phytochemistry Letters 6 (2013) iii–xii

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Phytochemistry Letters

journal homepage: www.elsevier .com/locate/phytol

Contents

Glabretal-type triterpenoids from Dysoxylum mollissimum

Consolacion Y. Ragasa, Oscar B. Torres, Leonisa O. Bernardo, Emelina H. Mandia, Ming-Jaw Don and Chien-Chang Shen

� New glabretal-type triterpenoids (1a–2b) were isolated from Dysoxylum mollissimum. � The structures of 1a–2b were eluci-dated by NMR spectroscopy and mass spectrometry. � Squalene, polyprenol, lutein and linoleic acid were also isolated.

doi:10.1016/S1874-3900(13)00180-8

Tetraoxygenated xanthones and bifl avanoids from the twigs of Garcinia merguensis

Kongkiat Trisuwan, Vatcharin Rukachaisirikul, Souwalak Phongpaichit and Nongporn Hutadilok-Towatana

� One new tetraoxygenated xanthone and six known compounds were isolated from the twigs of Garcinia merguensis. � Structures were elucidated by 1D and 2D NMR spectroscopy. � Their antibacterial and antioxidation activities were evaluated. � This is the fi rst report of the isolated compounds from the twigs of Garcinia merguensis.

pp 511–513

pp 514–518

pp 505–510Triterpenoid saponins from Piptadeniastrum africanum (Hook. f.) Brenan

Olivier Placide Noté, Azefack Léon Tapondjou, Anne-Claire Mitaine-offer, Tomofumi Miyamoto, Dieudonné Emmanuel Pegnyemb and Marie-Aleth Lacaille-Dubois

� Saponin content of Piptadeniastrum africanum was investigated. � One new and two known triterpene glycosides were isolated. � Direct interpretation of the spectroscopic data and comparison with the literature permitted their structure elucidation.

LETTERS

iv Phytochemistry Letters 6 (2013) iii–xii

A new triterpenic diester from the aerial parts of Chrysanthemum macrocarpum

Naima Boutaghane, Laurence Voutquenne-Nazabadioko, Alain Simon, Dominique Harakat, Kaddour Benlabed and Zahia Kabouche

� A new triterpenic dipalmitoylester (1) was isolated from aerial parts of Chrysanthemum macrocarpum. � Two cyclitols (2–3) and eleven known fl avonoids and triterpenes were also isolated. � Their structures were established by NMR and HRESIMS spectroscopy. � The chloroform frac-tion and taraxasterol showed antibacterial activity. � The chloroform fraction and taraxasterol showed cytotoxicity on human colon cancer HT-29 cells and human prostate carcinoma PC3 cells.

Isolation of two new phenolic compounds from the fruit of Chaenomeles speciosa (Sweet) Nakai

Guang-Hui Huang, Zhong-Xin Xi, Jun-Li Li, Cheng Chen, Gen-Jin Yang, Lian-na Sun, Wan-Sheng Chen and Hai-Ying Zhu

� Two new phenolic compounds specpolyphenol A and specphenoside A were obtained from Chaenomeles speciosa (Sweet) Nakai. � Three known phenyl glycosides were fi rst time isolated from Chaenomeles speciosa (Sweet) Nakai. � This study enriched the chemical information of Chaenomeles speciosa (Sweet) Nakai for the anti-infl ammatory activities.

Five new agarofuran sesquiterpene polyesters from Osyris lanceolata

Elizabeth M.O. Yeboah and Runner R.T. Majinda

� Phytochemical studies were carried out on Osyris lanceolata, Santalaceae. � Five new agarofuran-type sesquiterpene polyesters are presented in this report. � Structure elucidation was based on mass, 1D and 2D NMR spectroscopic analyses.

A new fused tetracyclic heterocyclic antioxidant from Serratia sp. PAMC 25557

Hari Datta Bhattarai, Babita Paudel, Kim Il Chan, Hyuncheol Oh and Joung Han Yim

� A new fused tetracyclic heterocycle compound 1 is described. � 1D & 2DNMR spectroscopic methods were used for the structure elucidation. � Spatozoate, compound 2 was originally reported from the marine alga Spatoglossum variable but is new to bacterial source. � Compound 1 showed antioxidant activity.

pp 536–538

pp 531–535

pp 526–530

pp 519–525

Phytochemistry Letters 6 (2013) iii–xii v

Ring A rearranged limonoids from the fruits of Aphanamixis grandifolia and their cytotoxicity evaluation

Yao Zhang, Jun-Song Wang, Yu-Cheng Gu and Ling-Yi Kong

� Four ring A rearranged limonoids isolated from Aphanamixis grandifolia. � Their structures were elucidated by modern spectroscopic methods. � The cytotoxic activities were evaluated in vitro against human cancer cell lines.

New derivatives from the aerial parts of Boerhaavia diffusa L. (Nyctaginaceae)

Thi My Lien Do, Anh Vu Truong, Thi Nga Vo, Travis G. Pinnock, Lawrence M. Pratt, Dominique Guillaume and Kim Phi Phung Nguyen

� Two new rotenoids, a new sesquiterpene lactone, a new phenylpropanoid were isolated from aerial part of B. diffusa. � A mixture of two atropisomers was isolated from B. diffusa. � Their structures were established on the basis of 1D and 2D NMR spectroscopy and HR-ESI-MS.

Chromone acyl glucosides and an ayanin glucoside from Dasiphora parvifolia

Toshihiro Murata, Erdenechimeg Selenge, Kento Suganuma, Yusuke Asai, Javzan Batkhuu and Fumihiko Yoshizaki

� Two new chromone acyl glucosides were isolated from Dasiphora parvifolia. � A new ayanin glucoside was isolated from Dasiphora parvifolia. � The DPPH radical scavengers and the hyaluronidase inhibitors were investigated.

Indazole-type alkaloids from the seeds of Nigella glandulifera

Yu-Ming Liu, Yu-Hu Jiang, Qing-Hua Liu and Bao-Quan Chen

� Two rare indazole-type alkaloids, nigeglapine (1) and nigeglaquine (2) were isolated from the seeds of Nigella glandulifera. � The structures were confi rmed on the basis of chemical and spectroscopic data. � This is the fi rst report of the natural occurrence of glycosylated indazole-type alkaloids. � Compounds 1 and 2 were highly applicable as chemical markers. � Indazole-type alkaloids show signifi cant role in the chemo-taxonomy of Nigella.

pp 556–559

pp 552–555

pp 544–551

pp 539–543

vi Phytochemistry Letters 6 (2013) iii–xii

A new meroterpenoid isolated from roots of Ptaeroxylon obliquum Radlk.

Daniel Agostinho, Leslie Boudesocque, Isabelle Thery-Kone, Françoise Debierre-Grockiego, Alain Gueiffi er, Cécile Enguehard-Gueiffi er and Hassan Allouchi

� A new monoterpene chromone was isolated from roots of Ptaeroxylon obliquum. � Extensive NMR and single crystal X-ray analysis were performed. � Biosynthesis pathway is proposed involving specifi c cyclase. � Activity on Toxoplasma gondii replication was investigated.

Tangshenosides from Codonopsis lanceolata roots

Jing Ren, Zhe Lin and Zhong Yuan

� Seven tangshenosides (1–7) were isolated from the roots of Codonopsis lanceolata. � 1 was a new symmetrical compound. � Tangshenosides have chemotaxonomic signifi cance.

Mandshunosides C–E from the roots and rhizomes of Clematis mandshuricaLing Li, Mei-Ling Gou and Yu-Xin He

� Triterpene saponins from the roots and rhizomes of Clematis mandshurica were stud-ied. � Three new and four known compounds were isolated. � Their structures were elucidated on the basis of spectroscopic evidence. � Inhibitory activities against human colorectal cancer cell lines were investigated.

Isolation and structure determination of two new hydrophobic microcystins from Microcystis sp. (CAWBG11)

Jonathan Puddick, Michèle R. Prinsep, Susanna A. Wood, S. Craig Cary, David P. Hamilton and Alistair L. Wilkins

� Two new hydrophobic microcystin congeners from Microcystis CAWBG11. � In-depth characteriza-tion by nuclear magnetic resonance spectroscopy. � Stereochemistry of the amino acids determined by the Advanced Marfey’s method.

pp 575–581

pp 570–574

pp 567–569

O

O

O

O

OCH

H CO

OCH

OCH

O

O

HO

HOOH

O

OH

OO

HO

HO OH

HO

O

HO

HOOH

OH

tangshenoside VIII

pp 560–566

Phytochemistry Letters 6 (2013) iii–xii vii

New diprenylated dihyrochalcones from leaves of Artocarpus elasticus

Faiqah Ramli, Mawardi Rahmani, Nur Kartinee Kassim, Najihah Mohd Hashim, Mohd Aspollah Sukari, Abdah Md Akim andRusea Go

� Two new diprenylated dihydrochalcones, named elastichalcone A and elastichalcone B, were isolated from leaves of Artocarpus elasticus. � The structures were elucidated on the basis of spectroscopic data. � The compounds were evaluated for free radical scavenging activity. � Elastichalcone B exhibited strong free radical scavenging activity with IC50 value of 11.30 �g/ml.

Sesquiterpenoids from the aerial parts of Chloranthus elatior

Juan Xiong, Shu-Ting Liu, Yu Tang, Wen-Xuan Wang, Van-Binh Bui, Yun Zhao, Hui Fan, Guo-Xun Yang and Jin-Feng Hu

� Three new and ten known sesquiterpenoids were isolated from Chloranthus elatior. � The absolute confi guration of 1 was established. � Compound 3 is the fi rst maaliane-type sesquiterpene from the genus Chloranthus.

A new benzoic acid derivative isolated from Piper cf. cumanense Kunth (Piperaceae)

Jorge E. Parra, Oscar J. Patiño, Juliet A. Prieto, Wilman A. Delgado and Luis E. Cuca

� New benzoic acid derivative, cumenic acid, has been isolated from the infl orescences of Piper cf. cumanense Kunth. � Cumenic acid structure was identifi ed on basis of spectroscopic analysis and comparison with literature data. � The compound showed antifungal activity against Fusarium oxysporum f. sp. dianthi and Botrytis cinerea.

Cytotoxic meroterpenoids from the macroalga Cystoseira abies-marina

Vera L.M. Gouveia, Ana M.L. Seca, M. Carmo Barreto, Ana I. Neto, Anake Kijjoa and Artur M.S. Silva

� Four new terpenoids were isolated from Cystoseira abies-marina. � Two are tetraprenyltoluquinols (cystoazorols A and B). � Another two are a pair of meronorsesquiterpene isomers (cystoazorones A and B). � Cystoazorol A was the most active against HeLa mainly in log phase of growth. � Cystoazorols A and B showed signifi cant antioxidant effect.

pp 593–597

pp 590–592

pp 586–589

pp 582–585

OOH

O

OH

OOH

HO

OH

O

1

viii Phytochemistry Letters 6 (2013) iii–xii

Cytotoxic glucosydic iridoids from Veronica americana

Jorge A. Moreno-Escobar, Laura Alvarez, Verónica Rodríguez-López and Silvia Marquina Bahena

� Two new acylated iridoids and four known aromatic acids were isolated. � They were isolated using bioassay-guided fractionations. � Structures have been elucidated by 2D NMR and FABMS spectrometry. � The iridoids showed selective activity against the human cancer cell lines HF-6 and PC-3.

6-Hydroxy-5,6-seco-stemocurtisine: A novel seco-stemocurtisine-type alkaloid

Pitchaya Mungkornasawakul, Stephen G. Pyne, Anthony C. Willis, Arayar Jatisatienr, Duang Phuthsuk and Wilford Lie

� The fi rst Stemona alkaloid with a seco-pyrido[1,2-a]azepine structure is reported. � The structure was elucidated using spectroscopic and X-ray crystallo-graphic analysis. � Biosynthesis proposed by azepine ring cleavage of co-isolated stemocurtisine.

pp 610–613

pp 606–609

pp 602–605

pp 598–601

Four new cassane diterpenes from the seeds of Caesalpinia minax

Peng Zhao, Hongqiang Chen, Hao Wang, Jing Xu, Meicheng Wang, Yuli Wang, Da-Qing Jin and Yuanqiang Guo

� Four new cassane diterpenes were isolated from the seeds of Caesalpinia minax. � Their structures were elucidated on the basis of 1D and 2D NMR and mass spectroscopic data analyses. � The phytochemical investigation further revealed the chemical constituents of Caesalpinia minax. � The cassane diterpenes are may be regarded as the characteristic constituents of Caesalpinia minax.

Two new isodrimene sesquiterpenes from the fungal culture broth of Polyporus arcularius

Junnosuke Otaka and Hiroshi Araya

� Two new isodrimene sesquiterpenes (1, 2) were isolated from the fermentation broth of Poluporus arcularius. � (1S,2S)-1-phenyl-1,2-dihydroxypropane (3) was isolated as a natural compound for the fi rst time. � The structures were elucidated on the basis of spectroscopic data. � Compound 1 showed plant growth inhibition to lettuce seedling hypocotyl at IC50 1.3 mM.

Phytochemistry Letters 6 (2013) iii–xii ix

�-Glucosidase inhibitory constituents from Chrozophora plicata

Asia Tabussum, Naheed Riaz, Muhammad Saleem, Muhammad Ashraf, Maqsood Ahmad, Umber Alam, Bushra Jabeen, Abdul Malik and Abdul Jabbar

� We isolated fi ve (1–5) new secondary metabolites from Chrozophora plicata. � Their structures were established by using spectroscopic and spectrometric techniques. � Structure of plicatanin A (3) was confi rmed through single crys-tal X-ray technique. � All the isolates (1–12) were found inhibitors of enzyme �-glucosidase except compound 9.

20(R)-Ginsenoside Rf: A new ginsenoside from red ginseng extract

Sang Myung Lee, Seok Chang Kim, Joonseok Oh, Jin Hee Kim and MinKyun Na

� 20(R)-ginsenoside Rf is produced from its epimer in acidic conditions. � The conversion occurs during the production of red ginseng. � Utilization of this fi nding updates the chemical profi le of ginseng products

Four new �-lactones from the endophytic Streptomyces sp. T1B1

Jia-Xin Yuan, Ying Zeng, Cheng Zou and Pei-Ji Zhao

� The strain T1B1 was isolated from the old bast tissue of Taxus yunnanensis. � Strain T1B1 was determined to be Streptomyces sp. according to the 16S rRNA analysis. � Four new �-lactones were isolated and determined.

Three new xanthones from the stems of Garcinia oligantha and their anti-TMV activ-ity

Yu-Ping Wu, Wei Zhao, Zhen-Yuan Xia, Guang-Hui Kong, Xiu-Ping Lu, Qiu-Fen Hu and Xue-Mei Gao

� Three new xanthones, oliganthins E–G were isolated from Garcinia oligan-tha. � Five known xanthones were isolated from Garcinia oligantha. � 1, 2, 6, 7, and 8 showed anti-TMV activities with inhibition rates above 10%.

pp 629–632

O

OOR1

OMe

OR2

OHHO

OH

1 R1 = Me; R2 = H

2 R1 = H; R2 = Me

13

57 9

1311

1415

1617

O

O

3

OMe

MeO O

OAc

OH

13

57

1311

9

14

15

16

pp 625–628

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pp 614–619

x Phytochemistry Letters 6 (2013) iii–xii

A new complex triterpenoid saponin from Calliandra pulcherrima with haemolytic activity and adjuvant effect

Bernadete Pereira da Silva and José Paz Parente

� A new complex triterpenoid saponin was isolated from Calliandra pulcherrima. � The structure was established by spectroscopic techniques and chemical conversions. � The compound exhibited signifi cant immuno-logical adjuvant activity

New phenanthrene glycosides from Dendrobium denneanum and their cytotoxic activity

Fu Li, Hong-Mei Pan, Xin Liu, Bin Chen, Ya-Xiong Tang, Xing-Jun Xi and Ming-Kui Wang

� Six new phenanthrene glycosides were isolated from the stem of Dendrobium denneanum. � Their structures were deduced by extensive spectroscopic analysis. � Some compounds showed moderate cytotoxic activities against SNU387 tumor cells.

Trinorsesquiterpenoids from Inula racemosa

Yan-Yan Ma, Deng-Gao Zhao, Ying Zhai, Ya Li and Kun Gao

� Compounds 1–4 were rarely reported trinorsesquiterpe-noids. � The structure of a previously reported trinorses-quiterpenoid was revised to compound 2. � The absolute configuration of compounds 1–3 was determined. � Compound 2 showed signifi cant antiproliferative activities.

A case of mistaken identity: Lupeol-3-(3�R)-hydroxy-stearate can be mistakenly identifi ed as lupeol acetate when only analyzed by GC–MS

Alejandro Yam-Puc, Fabiola Escalante-Erosa, Karlina García-Sosa, Fabiola G. Ramírez-Torres, Manuel J. Chan-Bacab, Wolfgang Eisenreich, Claudia Huber, Nihat Knispel, Gregorio Godoy-Hernández and Luis M. Peña-Rodríguez

� Lupeol-3-(3�R)-hydroxy-stearate can be misidentifi ed as lupeol acetate by only GC–MS. � Thermolysis of lupeol-3-(3�R)-hydroxystearate produces lupeol acetate and hexadecanal. � Thermolysis of �-hydroxy-esters is highly favored.

pp 649–652

pp 645–648

O

OH

1

O

OH

O

2 3

HO

9

74

15

14

1

pp 640–644

pp 633–639

Phytochemistry Letters 6 (2013) iii–xii xi

Induced defenses of Veronica spicata: Variability in herbivore-induced volatile organic compounds

Delia M. Pinto-Zevallos, Heidi Hellén, Hannele Hakola, Saskya van Nouhuys and Jarmo K. Holopainen

� We measured induced volatile organic compounds emitted by Veronica spicata. � Melitaea cinxia feeding and oviposition induced different compounds. � Increase of terpenoids and green leaf volatiles was associated with larval feeding. � Increase of two ketones was associated with oviposition. � Oviposition also resulted in suppression of green leaf volatiles.

Microbial transformation of �-lapachone to its glycosides by Cunninghamella elegans ATCC 10028b

Camila R. Paludo, Eduardo A. da Silva-Junior, Raquel A. Santos, Mônica T. Pupo, Flávio S. Emery and Niege A.J.C. Furtado

� Microbial transformation of �-lapachone furnished two new glycosylated derivatives. � These metabolites are similar to those that occur in phase II of human metabolism. � The major derivative was less active and more selective than �-lapachone. � The results are valu-able for the development of rational approaches in drug design.

Austdiol, fulvic acid and citromycetin derivatives from an endolichenic fungus, Myxotrichum sp.

Chao Yuan, Hai-Ying Wang, Chang-Sheng Wu, Yang Jiao, Ming Li, Yan-Yan Wang, Shu-Qi Wang, Zun-Tian Zhao and Hong-Xiang Lou

� The fi rst report of austdiol, fulvic acid and citromycetin derivatives from endophytic fungus isolated from lichen. � The fi rst report of chlorine-connected metabolite from endolichenic fungus. � Compounds 2 and 5 display very weak cytotoxicity against cell line K562.

Novel isolation of resveratrol dimer O-glucosides with enantiomeric aglycones from the leaves of Shorea cordifolia

Tetsuro Ito, Kouko Nishiya, Masayoshi Oyama, Toshiyuki Tanaka, Jin Murata, Dedy Darnaedi and Munekazu Iinuma

� Two new glucosides of resveratrol dimers were isolated from Shorea cordifolia. � Absolute confi gurations of isolates were determined based on CD spectral properties. � Co-occurrence of O-glucosides of resveratrol dimers with enantiomeric aglycones was exhibited.

pp 667–670

pp 662–666

pp 657–661

O

OH

O

O

HO

OHOH

HO

O

O

OH

O

OHOH

HO

OH

O

O

O

Cunninghamellaelegans

2 31

pp 653–656

xii Phytochemistry Letters 6 (2013) iii–xii

pp 681–685Acylated iridoid glycosides and acylated rhamnopyranoses from Gmelina arborea fl owers

Wei Gu, Xiao-Jiang Hao, Hong-Xin Liu, Yue-Hu Wang and Chun-Lin Long

� Gmelina arborea fl ower is a medicinal-edible plants in Xishuangbanna, China. � The major chemical components including 5 new compounds of G. arborea fl ower were isolated and identifi ed. � The in vitro hepatopro-tective activity of selected chemical constituents were tested.

3-Hydroxyisofl avanones from the stem bark of Dalbergia melanoxylon: Isolation, antimycobacterial evaluation and molecular docking studies

Peggoty Mutai, Matthias Heydenreich, Grace Thoithi, Grace Mugumbate, Kelly Chibale and Abiy Yenesew

� Two new 3-hydroxyisofl avanones were isolated from Dalbergia melanoxylon. � Kenusanone F 7-methyl ether showed activity against Mycobacterium tuberculosis H37Rv strain. � The new compounds have high affi nity for the mycobacterial drug target INHA.

Omphalocarpoidone, a new lanostane-type furano-spiro-�-lactone from the wood of Tridesmostemon omphalocarpoides Engl. (Sapotaceae)

Chi G. Fru, Louis P. Sandjo, Victor Kuete, Johannes C. Liermann, Dieter Schollmeyer, Samuel O. Yeboah, Renameditswe Mapitse, Berhanu M. Abegaz, Bonaventure T. Ngadjui and Till Opatz

� A new spiro-lanostane has been isolated from Tridesmostemon ompha-locarpoides Engl. � Its structure was determined by 2D NMR spectroscopy and X-ray crystallography. � Eight known compounds were isolated from the same organism. � Two known metabolites show a signifi cant antibac-terial activity against Escherichia coli.

pp 676–680

pp 671–675