Natural occurring 2-(2-phenylethyl) chromones, structure elucidation and biological activities

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Natural occurring 2-(2-phenylethyl)chromones, structure elucidation andbiological activitiesSabrin R.M. Ibrahimab & Gamal A. Mohamedcd

a Department of Pharmacognosy and Pharmaceutical Chemistry,Faculty of Pharmacy, Taibah University, Al Madinah Al,Munawwarah 30078, Kingdom of Saudi Arabiab Department of Pharmacognosy, Faculty of Pharmacy, AssiutUniversity, Assiut 71526, Egyptc Department of Natural Products and Alternative Medicine,Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589,Kingdom of Saudi Arabiad Department of Pharmacognosy, Faculty of Pharmacy, Al-AzharUniversity, Assiut Branch, Assiut 71524, EgyptPublished online: 20 Dec 2014.

To cite this article: Sabrin R.M. Ibrahim & Gamal A. Mohamed (2014): Natural occurring 2-(2-phenylethyl) chromones, structure elucidation and biological activities, Natural Product Research:Formerly Natural Product Letters, DOI: 10.1080/14786419.2014.991323

To link to this article: http://dx.doi.org/10.1080/14786419.2014.991323

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Natural occurring 2-(2-phenylethyl) chromones, structure elucidation andbiological activities

Sabrin R.M. Ibrahimab* and Gamal A. Mohamedcd

aDepartment of Pharmacognosy and Pharmaceutical Chemistry, Faculty of Pharmacy, Taibah University,Al Madinah Al, Munawwarah 30078, Kingdom of Saudi Arabia; bDepartment of Pharmacognosy, Facultyof Pharmacy, Assiut University, Assiut 71526, Egypt; cDepartment of Natural Products and AlternativeMedicine, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia;dDepartment of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524,Egypt

(Received 9 October 2014; final version received 16 November 2014)

2-(2-Phenylethyl) chromone (PEC), an uncommon class of chromones, possesses aphenylethyl substituent at the C2 position. They have been isolated from a few plantspecies. They have promising biological activities such as neuro-protective, cytotoxic,acetylcholinesterase inhibitory, antibacterial and anti-inflammatory. This reviewfocuses on the naturally occurring PEC derivatives, their sources, physical and spectraldata, as well as biological activities.

Keywords: 2-(2-phenylethyl) chromones; physical data; spectral data; plant source;biological activities

1. Introduction

Natural products have been of great interest for many years, and have provided modern medicine

with numerous useful drug leads (Butler 2005; Newman & Cragg 2012). One family of natural

products being widely explored for their biological activity is that containing the chromone

skeleton (Middleton et al. 2000). Chromones are a class of natural products found in almost

every known terrestrial plant and over 4000 naturally occurring derivatives have been isolated

and structurally elucidated. They include 2-(2-phenylethyl) chromones (PECs) and flavonoids.

q 2014 Taylor & Francis

*Corresponding author. Email: [email protected]

Natural Product Research, 2014

http://dx.doi.org/10.1080/14786419.2014.991323

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mailto:[email protected]

mailto:[email protected]

http://dx.doi.org/10.1080/14786419.2014.991323

https://www.researchgate.net/publication/235784470_Natural_Products_to_Drugs_Natural_Product_Derived_Compounds_in_Clinical_Trials?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

https://www.researchgate.net/publication/12206219_Middleton_Jr_E_Kandaswami_C__Theoharides_TC_The_effects_of_plant_flavonoids_on_mammalian_cells_implications_for_inflammation_heart_disease_and_cancer._Pharmacol._Rev._52_673-751?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

https://www.researchgate.net/publication/267333936_Natural_products_as_sources_of_new_drugs_over_the_30_years_from_1981_to_2010?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

Perhaps the most widely studied chromones are the flavonoids, which bear a phenyl group at C-2

(Cazarolli et al. 2008; Ibrahim et al. 2012). PEC, a relatively small and under-explored class of

chromones, possesses a phenylethyl substituent at the C2 position, which is quite uncommon.

In addition to their unique structural feature, chromones within this family have demonstrated

neuroprotective activity, a property for potentially treating neurodegenerative disorders (Yoon

et al. 2006; Yang et al. 2012). They have been obtained only from a few plant species such

Eremophila georgei (Myoporaceae) (Picker et al. 1976), Bothriochloa ischaemum (Gramineae)

(Wang et al. 2001), Imperata cylindrica (Gramineae) (Yoon et al. 2006; Xuan et al. 2013),

Cucumis melo L. (Cucurbitaceae) (Ibrahim 2010, 2014) and Aquilaria spp. (Thymelaeaceae)

(Yang 1998). Flavonoid is derived from chalcone compound which is synthesised from a

molecule of 4-coumaroyl-CoA and three molecules of malonyl-CoA by chalcone synthase

(Shirley 1996). However, there has been no report on the biosynthesis of PEC yet. Reviewing the

available literature, we found no review concerning the naturally occurring PECs. Here, we

listed the PECs that have appeared in the literature over the past few decades, with their

biological activities, physical constants, spectral data, plant source and references. For each

compound these data were listed in the following order: name, structure, melting point (8C),optical rotation (concentration, solvent), UV (solvent, lmax nm, log 1), infrared (IR) (medium,

absorption band in cm21), 1H NMR (spectrometer frequency, solvent, chemical shift values in dppm, starting with H-3 and listed in order), 13C NMR (spectrometer frequency, solvent, chemical

shift in d values starting with C-2 and listed in order), plant source (family), molecular formula,

calculated molecular weight and reference(s). The 1H NMR data have been rounded to the

second decimal point and the 13C NMR data to the first decimal point. The molecular weight data

have been rounded to the fourth decimal point. The main aim of this review is to provide

knowledge to researchers for rapid identification of isolated PECs by comparison of physical and

spectral data. The highlight of bioactivity may possibly draw the attention of synthetic chemists

for design of new drugs using known PECs as raw materials. All the new PECs are arranged in

three groups. Group I contains PECs with a monomer-carbon skeleton, whereas group II

contains PECs with a dimer-carbon skeleton and group III contains PECs with a trimer-carbon

skeleton (Tables 1–3).

2. Characterisation of PECs by different spectroscopic data

2.1. Infrared spectroscopy

PECs showed IR absorption bands for a hydroxyl group (OH) at 3200–3500 cm21 and strong

absorption bands at 1630–1655 and 1582–1595 cm21 for g-pyrone moiety.

2.2. Mass spectroscopy (MS)

All the isolated PECs share the same basic skeleton (Mol. wt.m/z: 250) and substituted groups as

methoxy or/and hydroxyl. The number of methoxy or hydroxyl groups can be determined by

using the following equation (Mei et al. 2013): 30m þ 16n ¼ MW 2 250, where m is the

number of methoxy groups, n is the number of hydroxyl groups and MW is molecular weight.

PECs showed characteristic fragment ion peaks due to the haemolytic b-cleavage of the

CH2ZCH2 bond between the chromone moiety and phenyl moiety. Thus, the substituted benzyl

moieties possess characteristic fragment ions such as m/z 91 [C7H7], 107 [C7H6 þ OH], 121

[C7H6 þ OCH3] and 137 [C7H5 þ OH þ OCH3]. However, the substituted chromone moieties

provide characteristic fragment ions such as m/z 160 [C10H8O2], 176 [C10H7O2 þ OH], 190

[C10H7O2 þ OCH3] and 220 [C10H6O2 þ OCH3 £ 2]. Furthermore, it was reported that there is

a relationship between the positions of hydroxyl or methoxy groups and the relative abundances

of benzyl and chromone fragment ions (Mei et al. 2013; Xia et al. 2013).

2 S.R.M. Ibrahim and G.A. Mohamed

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Table 1. Naturally occurring PECs: Group-I (monomer-carbon skeleton).

Flindersiachromone 2-(2-phenylethyl)chromone (1)Pale yellow needles; mp 65–668C; IR gmax cm21: 1642, 1601, 1460,1380; 1H NMR (CDCl3, 80MHz): dH 6.12 (s, H-3), 8.17 (m, H-5), 7.37(m, H-6-8, 20-60), 3.05 (m, H-70, 80) (Hashimoto et al. 1985); 13C NMR(CDCl3, 20MHz): dC 168.32 (C-2), 110.22 (C-3), 178.03 (C-4), 124.94(C-5), 125.67 (C-6), 133.43 (C-7), 117.83 (C-8), 156.45 (C-9), 123.79(C-10), 139.73 (C-10), 128.63 (C-20, 60), 128.29 (C-30, 50), 126.54 (C-40),32.94 (C-70), 36.02 (C-80) (Hashimoto et al. 1985); HR-EI-MS m/z250.0981 [M]þ (calcd for C17H14O2, 250.0970); Japanese Agarwood(A. sinensis), family Thymelaeaceae (Hashimoto et al. 1985); Aquilariacrassna Pierre ex Lecomte, family Thymelaeaceae (Yagura et al. 2005);Flindersia laevicarpa C. T. White & Francis, family Rutaceae(Picker et al.1976).

6-Hydroxy-2-(2-phenylethyl) chromone (2)Solid; mp 214–2158C; UV (MeOH) lmax (log 1): 227 (4.42), 240 (4.39),272 (3.91), 330 (3.81) nm; IR gmax cm

21: 3270, 1640, 1620, 1602, 1583,1470; 1H NMR (400MHz, DMSO-d6): dH 6.12 (s, H-3), 7.47 (d,J ¼ 9.0Hz, H-5), 7.16–7.21 (m, H-7, 8), 7.23–731 (m, H-20-60), 2.97(m, H-70, 80), 9.96 (s, OH); 13C NMR (100MHz, DMSO-d6):dC 168.30(C-2), 108.64 (C-3), 176.67 (C-4), 107.50 (C-5), 154.58 (C-6), 122.72(C-7), 119.41 (C-8), 149.59 (C-9), 123.95 (C-10), 140.06 (C-10), 128.34(C-20), 128.29 (C-30), 126.18 (C-40), 128.29 (C-50), 128.34 (C-60), 32.06(C-70), 34.80 (C-80); A. sinensis, family Thymelaeaceae (Yang et al.1989).

6-Hydroxy-2-[2-(40-methoxyphenyl)ethyl]chromone (3)Solid; mp 167–1688C; UV (MeOH) lmax (log 1): 226 (4.46), 240 (4.33),274 (3.88), 330 (3.78) nm; IR gmax cm21: 3300, 1640, 1610, 1587,1500; 1H NMR (400MHz, CDCl3): dH 6.18 (s, H-3), 7.83 (d,J ¼ 3.0Hz, H-5), 7.24 (dd, J ¼ 9.0, 3.0Hz, H-7), 7.37 (d, J ¼ 9.0Hz,H-8), 7.08 (m, H-20, 60), 6.78 (m, H-30, 50), 2.95 (m, H-70, 80), 3.77 (s, 40-OCH3);

13C NMR (100MHz, CDCl3): dC 167.95 (C-2), 108.33 (C-3),176.40 (C-4), 107.57 (C-5), 154.58 (C-6), 122.31 (C-7), 118.84 (C-8),149.52 (C-9), 123.83 (C-10), 131.64 (C-10), 128.93 (C-20, 60), 113.64 (C-30, 50), 157.65 (C-40), 31.05 (C-70), 34.84 (C-80), 54.68 (40-OCH3); HR-EI-MS m/z 496.1049 [M]þ (calcd for C13H16O4, 296.1048); A. sinensis,family Thymelaeaceae (Yang et al. 1989).

6-Methoxy-2-[2-(40-methoxyphenyl)ethyl]chromone (4)1H NMR (400MHz, CDCl3): dH 6.13 (s, H-3), 7.55 (d, J ¼ 3.0Hz, H-5),7.24 (dd, J ¼ 9.1, 3.0Hz, H-7), 7.37 (d, J ¼ 9.1Hz, H-8), 7.11 (m, H-20,60), 6.82 (m, H-30, 50), 2.89 (m, H-70), 3.00 (m, H-80), 3.78 (s, 40-OCH3),3.89 (s, 6-OCH3);

13C NMR (100MHz, CDCl3):dC 168. 27 (C-2),109.55 (C-3), 178.16 (C-4), 104.90 (C-5), 151.33 (C-6), 123.50 (C-7),119.24 (C-8), 156.82 (C-9), 124.34 (C-10), 131.80 (C-10), 129.24 (C-20,60), 114.06 (C-30, 50), 158.28 (C-40), 32.21 (C-70), 36.38 (C-80), 55.29(40-OCH3), 55.93 (6-OCH3); A. sinensis, family Thymelaeaceae(Yang et al. 1989).

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Table 1. (Continued)

6-Hydroxy-7-methoxy-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]chromone (5)White amorphous solid; UV (MeOH) lmax (log 1): 231 (4.48), 281(4.09), 321 (4.00) nm; IR gmax cm

21: 3313 (OH), 2465, 1628, 1585 (g-pyrone), 1514, 1474, 1395, 1271, 1235, 1212, 1080, 977, 949, 842, 826;1H NMR (CDCl3/CD3OD (1:1,v/v), 600MHz): dH 6.06 (s, H-3), 7.37 (s,H-5), 7.05 (s, H-8), 6.69 (d, J ¼ 2.4Hz, H-20), 6.79 (d, J ¼ 8.4Hz, H-50), 6.63 (dd, J ¼ 8.4, 2.4Hz, H-60), 2.93 (m, H-70), 2.92 (m, H-80), 3.99(s, 7-OCH3), 3.81 (s, 40-OCH3);

13C NMR (CDCl3/CD3OD (1:1,v/v),150MHz): dC 170.4 (C-2), 109.7 (C-3), 179.9 (C-4), 108.4 (C-5), 146.4(C-6), 155.3 (C-7), 100.6 (C-8), 153.4 (C-9), 117.7 (C-10), 134.0 (C-10),116.3 (C-20), 147.3 (C-30), 147.4 (C-40), 112.7 (C-50), 120.4 (C-60), 33.4(C-70), 37.1 (C-80), 56.9 (7-OCH3), 56.4 (40-OCH3); EI-MS: m/z (rel.int.): 342 [M]þ (60), 324 (7), 253 (6), 206 (72), 149 (34), 137 (100), 83(27), 72 (25), 58 (38); HR-ESI-MS m/z: 343.1168 [M þ H]þ (calc. forC19H19O6, 343.1176); Chinese Eaglewood (A. sinensis (Lour.) Gilg),family Thymelaeaceae (Yang et al. 2012).

6,7-Dimethoxy-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]chromone (6)Yellow amorphous solid; UV (MeOH) lmax (log 1): 232 (4.43), 280(4.04), 316 (3.96) nm; IRgmax cm

21: 3359 (OH), 1639, 1595, 1505, 1473,1429, 1386, 1337, 1270, 1237, 1196, 1080, 1037, 968, 841, 817; 1HNMR(CDCl3, 600MHz): dH 6.11 (s, H-3), 7.51 (s, H-5), 6.87 (s, H-8), 6.79 (d,J ¼ 1.8Hz, H-20), 6.75 (d, J ¼ 8.4Hz, H-50), 6.65 (dd, J ¼ 8.4, 1.8Hz,H-60), 2.96 (t, J ¼ 7.8Hz, H-70), 2.87 (t, J ¼ 7.8Hz, H-80), 3.96 (s, 6-OCH3), 3.99 (s, 7-OCH3), 3.86 (s, 40-OCH3);

13C NMR (CDCl3,150MHz): dC 167.7 (C-2), 109.6 (C-3), 177.5 (C-4), 104.4 (C-5), 147.4(C-6), 154.3 (C-7), 99.6 (C-8), 152.5 (C-9), 116.9 (C-10), 133.0 (C-10),114.4 (C-20), 145.6 (C-30), 145.2 (C-40), 110.7 (C-50), 119.6 (C-60), 32.4(C-70), 36.1 (C-80), 56.3 (6-OCH3), 56.4 (7-OCH3), 56.0 (4

0-OCH3); EI-MS, m/z (rel. int.): 356 [M]þ (75), 338 (7), 220 (100), 191 (9), 149 (16),137 (81), 83 (15), 72 (17), 58 (24); HR-ESI-MSm/z: 357.1333 [M þ H]þ

(calc. for C20H21O6, 357.1333); Chinese Eaglewood (A. sinensis (Lour.)Gilg), family Thymelaeaceae (Yang et al. 2012).

7-Hydroxy-6-methoxy-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]chromone (7)Colourless needles (MeOH); mp 199–2018C; UV (MeOH) lmax (log 1):282 (4.23), 326 (4.15) nm; IR gmax cm

21: 3432 (OH), 1630, 1586, 1544,1509, 1482, 1424, 1394, 1281, 1254, 1218, 974, 849, 815; 1H NMR(C5D5N, 600MHz): dH 6.33 (s, H-3), 7.82 (s, H-5), 7.24 (s, H-8), 7.17 (d,J ¼ 1.8Hz, H-20), 6.89 (d, J ¼ 8.4Hz, H-50), 6.76 (dd, J ¼ 8.4, 1.8Hz, H-60), 2.95 (t, J ¼ 7.8Hz, H-70), 2.85 (t, J ¼ 7.8Hz, H-80), 3.71 (s, 6-OCH3),3.68 (s, 40-OCH3);

13C NMR (C5D5N, 150MHz): dC 167.8 (C-2), 109.7(C-3), 177.2 (C-4), 105.3 (C-5), 147.6 (C-6), 154.4 (C-7), 104.2 (C-8),153.4 (C-9), 116.8 (C-10), 133.8 (C-10), 116.9 (C-20), 148.3 (C-30), 147.3(C-40), 112.6 (C-50), 119.3 (C-60), 32.6 (C-70), 36.2 (C-80), 55.9 (6-OCH3),56.0 (40-OCH3); HR-ESI-MS m/z: 343.1178 [M þ H]þ (calc. forC19H19O6, 343.1176); Chinese Eaglewood (A. sinensis (Lour.) Gilg),family Thymelaeaceae (Yang et al. 2012).

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6,7-Dimethoxy-2-[2-(40-hydroxy-30-methoxyphenyl) ethyl]chromone (8)Yellow amorphous solid; (MeOH) lmax (log 1): 232 (4.44), 280 (4.03),315 (3.93) nm; IR gmax cm21: 3288 (OH), 2923, 1652, 1541, 1464,1404, 1242, 1172, 1083, 972, 721; 1H NMR (CD3OD, 400MHz): dH6.03 (s, H-3), 7.37 (s, H-5), 7.03 (s, H-8), 6.69 (d, J ¼ 2.0Hz, H-20),6.62 (d, J ¼ 8.0Hz, H-50), 6.56 (dd, J ¼ 8.0, 2.0 Hz, H-60), 2.93 (m, H-70), 2.89 (m, H-80), 3.84 (s, 6-OCH3), 3.90 (s, 7-OCH3), 3.68 (s, 40-OCH3);

13C NMR (CD3OD, 100MHz): dC 170.9 (C-2), 110.0 (C-3),179.8 (C-4), 104.8 (C-5), 149.3 (C-6), 156.6 (C-7), 101.0 (C-8), 154.4(C-9), 117.3 (C-10), 132.7 (C-10), 113.1 (C-20), 148.9 (C-30), 146.1 (C-40), 116.2 (C-50), 121.8 (C-60), 33.8 (C-70), 37.3 (C-80), 56.6 (6-OCH3),57.0 (7-OCH3), 56.3 (30-OCH3); HR-ESI-MS m/z: 357.1314 [M þ H]þ

(calc. for C20H21O6, 357.1333); Chinese Eaglewood (A. sinensis (Lour.)Gilg), family Thymelaeaceae (Yang et al. 2012).

6,7-Dihydroxy-2-[2-(40-methoxyphenyl)ethyl]chromone (9)Blue violet amorphous solid; (MeOH) lmax (log 1): 225 (4.70), 281(4.12), 327 (4.16) nm; IR gmax cm21: 3450 (OH), 1632, 1558, 1512,1457, 1393, 1271, 1241, 1179, 1034, 973, 837, 562; 1H NMR (CDCl3/CD3OD (1:1,v/v), 400MHz): dH 6.02 (s, H-3), 7.37 (s, H-5), 6.89 (s, H-8), 7.10 (d, J ¼ 8.0Hz, H-20), 6.81 (d, J ¼ 8.0Hz, H-30), 6.81 (d,J ¼ 8.0Hz, H-50), 7.10 (d, J ¼ 8.0Hz, H-60), 2.99 (t, J ¼ 7.2Hz, H-70),2.91 (t, J ¼ 7.2Hz, H-80), 3.76 (s, 40-OCH3);

13C NMR (CDCl3/CD3OD(1:1,v/v), 100MHz): dC 170.0 (C-2), 109.4 (C-3), 180.0 (C-4), 108.3 (C-5), 145.6 (C-6), 153.8 (C-7), 103.5 (C-8), 153.5 (C-9), 116.8 (C-10),132.9 (C-10), 130.1 (C-20), 114.7 (C-30), 159.3 (C-40), 114.7 (C-50),130.1 (C-60), 33.0 (C-70), 37.0 (C-80), 55.6 (40-OCH3); EI-MS m/z (rel.int.): 312 [M]þ (12), 191 (8), 163 (6), 149 (16), 121 (100), 83 (23), 72(37), 58 (53); HR-ESI-MS m/z: 313.1070 [M þ H]þ (calc. forC18H17O5, 313.1071); Chinese Eaglewood (A. sinensis (Lour.) Gilg),family Thymelaeaceae (Yang et al. 2012).

6-Hydroxy-7-methoxy-2-[2-(30,40-hydroxyphenyl)ethyl]chromone (10)White amorphous solid; UV (MeOH) lmax (log 1): 229 (4.38), 279(3.95), 323 (3.89) nm; IR gmax cm21: 3178 (OH), 1635, 1621, 1566,1509, 1487, 1383, 1276, 1215, 1081, 968, 847; 1H NMR (C5D5N,400MHz): dH 6.36 (s, H-3), 8.11 (s, H-5), 7.12 (s, H-8), 7.23 (d,J ¼ 8.0Hz, H-20), 7.15 (d, J ¼ 8.0Hz, H-30), 7.15 (d, J ¼ 8.0Hz, H-50),7.23 (d, J ¼ 8.0Hz, H-60), 2.98 (t, J ¼ 7.6Hz, H-70), 2.87 (t, J ¼ 7.6Hz,H-80), 3.86 (s, 7-OCH3);

13C NMR (C5D5N, 100MHz): dC 167.9 (C-2),109.7 (C-3), 177.3 (C-4), 109.1 (C-5), 146.6 (C-6), 154.2 (C-7), 103.5(C-8), 151.9 (C-9), 118.3 (C-10), 131.0 (C-10), 129.9 (C-20), 116.4 (C-30), 157.5 (C-40), 116.4 (C-50), 129.9 (C-60), 32.5 (C-70), 36.4 (C-80),56.2 (7-OCH3); HR-EI-MS m/z: 313.1066 [M þ H]þ (calc. forC18H17O5, 313.1071); Chinese Eaglewood (A.sinensis (Lour.) Gilg),family Thymelaeaceae (Yang et al. 2012).

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6,8-Dihydroxy-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]chromone (11)Sandy brown, amorphous solid; UV (MeOH) lmax (log 1): 242 (4.52),338 (3.74) nm; IR gmax cm21: 3349 (OH), 2538, 1627, 1585, 1552,1514, 1399, 1302, 1278, 1140, 1031, 987, 861, 845; 1H NMR (CD3OD,400MHz): dH 6.00 (s, H-3), 6.79 (d, J ¼ 2.8Hz, H-5), 6.68 (d,J ¼ 2.8Hz, H-7), 6.64 (d, J ¼ 2.0Hz, H-20), 6.74 (d, J ¼ 8.0Hz, H-50),6.57 (dd, J ¼ 8.0, 2.0Hz, H-60), 2.91 (m, H-70), 2.91 (m, H-80), 3.74 (s,40-OCH3);

13C NMR (CD3OD/CD3COCD3 (1:1,v/v), 100MHz): dC170.3 (C-2), 109.7 (C-3), 179.9 (C-4), 99.2 (C-5), 156.2 (C-6), 109.4 (C-7), 148.9 (C-8), 141.9 (C-9), 126.0 (C-10), 134.3 (C-10), 116.8 (C-20),147.4 (C-30), 147.7 (C-40), 112.8 (C-50), 120.4 (C-60), 33.2 (C-70), 36.9(C-80), 56.4 (40-OCH3); HR-ESI-MS m/z: 329.1013 [M þ H]þ (calc. forC18H17O6, 329.1020); Chinese Eaglewood (A. sinensis (Lour.) Gilg),family Thymelaeaceae (Yang et al. 2012).

6-Hydroxy-2-[2-(40-hydroxy-30-methoxyphenyl)ethenyl]chromone (12)Golden red amorphous solid; UV (MeOH) lmax (log 1): 258 (3.75), 365(3.92) nm; IR gmax cm

21: 3373 (OH), 3276, 1665, 1632, 1611, 1564,1475, 1400, 1283, 1257, 1234, 1160, 1124, 1032, 983, 965, 849; 1HNMR (C5D5N, 600MHz): dH 6.52 (s, H-3), 8.10 (brs, H-5), 7.51 (brd,J ¼ 8.4Hz, H-7), 7.58 (d, J ¼ 8.4Hz, H-8), 7.44 (brs, H-20), 7.25 (d,J ¼ 7.8Hz, H-50), 7.32 (brd, J ¼ 7.8Hz, H-60), 7.77 (d, J ¼ 15.6Hz, H-70), 7.02 (d, J ¼ 15.6Hz, H-80), 3.81 (s, 30-OCH3);

13C NMR (C5D5N,100MHz): dC 162.6 (C-2), 109.2 (C-3), 177.9 (C-4), 109.2 (C-5), 156.2(C-6), 123.7 (C-7), 119.8 (C-8), 150.0 (C-9), 125.9 (C-10), 127.9 (C-10),111.2 (C-20), 149.1 (C-30), 150.7 (C-40), 117.0 (C-50), 123.1 (C-60),137.4 (C-70), 117.8 (C-80), 55.9 (30-OCH3); HR-ESI-MS m/z: 311.0914[M þ H]þ (calc. for C18H15O5, 311.0914); Chinese Eaglewood(A. sinensis (Lour.) Gilg), family Thymelaeaceae (Yang et al. 2012).

5,7-Dihydroxy-2-(2-(3-methoxy-4-hydroxyphenyl)ethyl)chromone (13)Yellow crystals; mp 221–2228C; UV (MeOH): lmax 345, 256 nm; 1HNMR (400MHz, DMSO-d6): dH 6. 72 (s, H-3), 6.24 (d, J ¼ 2.0Hz, H-6), 6.50 (d, J ¼ 2.0Hz, H-8), 7.45 (brs, H-20), 6.94 (d, J ¼ 8.1Hz, H-50),7.43 (brd, J ¼ 8.1Hz, H-60), 2.80 (t, J ¼ 6.3Hz, H-70), 3.16 (t,J ¼ 6.3Hz, H-80), 13.15 (s, 5-OH), 3.98 (s, 30-OCH3);

13C NMR(100MHz, DMSO-d6): dC 164.3 (C-2), 103.2 (C-3), 182.1 (C-4), 161.7(C-5), 99.1 (C-6), 164.5 (C-7), 94.2 (C-8), 157.3 (C-9), 104.1 (C-10),121.9 (C-10), 113.8 (C-20), 146.2 (C-30), 148.2 (C-40), 116.3 (C-50),119.3 (C-60), 45.4 (C-70), 36.4 (C-80), 55.7 (30-OCH3); HR-EI-MS m/z:328.0945 [M]þ (calcd for C18H16O6, 328.0947); Seeds of C. meloL. var. reticulates, family Cucurbitaceae (Ibrahim 2014).

5,7-Dihydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (14)Yellow crystalline needles; mp 198–2008C; UV (MeOH) lmax: 341,258 nm; 1H NMR (400MHz, DMSO-d6): dH 6.70 (s, H-3), 6.18 (d,J ¼ 2.2Hz, H-6), 6.47 (d, J ¼ 2.2Hz, H-8), 7.78 (d, J ¼ 8.8Hz, H-20),6.93 (d, J ¼ 8.8Hz, H-30), 6.93 (d, J ¼ 8.8Hz, H-50), 7.78 (d,J ¼ 8.8Hz, H-60), 2.70 (t, J ¼ 6.9Hz, H-70), 3.03 (t, J ¼ 6.9Hz, H-80),12.96 (s, 5-OH); 13C NMR (100MHz, DMSO-d6): dC 163.8 (C-2),103.5 (C-3), 181.7 (C-4), 161.5 (C-5), 98.6 (C-6), 94.1 (C-8), 121.7 (C-10), 128.9 (C-20), 116.1 (C-30), 161.3 (C-40), 116.1 (C-50), 128.9 (C-60),39.4 (C-70), 37.2 (C-80); HR-EI-MS m/z: 298.0842 [M]þ (calcd forC17H14O5, 298.0841); Seeds of C. melo L. var. Reticulates, familyCucurbitaceae (Ibrahim 2010).

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5,7-Dihydroxy-2-[2-(3,4-dihydroxyphenyl)ethyl]chromone (15)Yellowish white needles (MeOH); mp 223–2258C; UV (MeOH) lmax:349, 254 nm; IR (KBr) gmax cm

21: 3425, 1652, 1616, 1580, 1169, 1084,951; 1H NMR (400MHz, DMSO-d6): dH 6.66 (s, H-3), 6.17 (d,J ¼ 2.2Hz, H-6), 6.44 (d, J ¼ 2.2Hz, H-8), 7.41 (d, J ¼ 2.2Hz, H-20),6.88 (d, J ¼ 8.2Hz, H-50), 7.39 (d, J ¼ 8.2, 2.2Hz, H-60), 2.70 (t,J ¼ 6.3Hz, H-70), 3.04 (t, J ¼ 6.3Hz, H-80), 12.98 (s, 5-OH); 13C NMR(100MHz, DMSO-d6): dC 164.3 (C-2), 103.2 (C-3), 182.0 (C-4), 161.9(C-5), 99.2 (C-6), 164.6 (C-7), 94.3 (C-8), 157.7 (C-9), 104.1 (C-10),121.9 (C-10), 113.8 (C-20), 146.2 (C-30), 150.1 (C-40), 116.4 (C-50),119.4 (C-60), 48.0 (C-70), 36.5 (C-80); HR-EI-MS m/z: 314.0789 [M]þ

(calcd for C17H14O6, 314.0790); Seeds of C. melo L. var. reticulates,family Cucurbitaceae (Ibrahim 2010).

7-Glucosyloxy-5-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (16)Yellow amorphous powder; UV (MeOH) lmax: 341, 260 nm; 1H NMR(400MHz, DMSO-d6): dH 6.86 (s, H-3), 6.45 (d, J ¼ 2.2Hz, H-6), 6.82(d, J ¼ 2.2Hz, H-8), 7.91 (d, J ¼ 8.8Hz, H-20), 6.94 (d, J ¼ 8.8Hz, H-30), 6.94 (d, J ¼ 8.8Hz, H-50), 7.91 (d, J ¼ 8.8Hz, H-60), 2.70 (t,J ¼ 6.3Hz, H-70), 3.03 (t, J ¼ 6.3Hz, H-80), 5.06 (d, J ¼ 7.6Hz, H-100),3.81–3.20 (m, H-200-600); 13C NMR (100MHz, DMSO-d6): dC 165.0 (C-2), 99.3 (C-6), 162.9 (C-7), 94.8 (C-8), 121.6 (C-10), 128.5 (C-20), 115.7(C-30), 161.5 (C-40), 115.7 (C-50), 128.5 (C-60), 39.1 (C-70), 37.5 (C-80),100.3 (C-100); HR-EI-MS m/z: 460.1368 [M]þ (calcd for C23H24O10,460.1369); Seeds of C. melo L. var. reticulates, family Cucurbitaceae(Ibrahim 2010).

8-Hydroxy-2-(2-phenylethyl)chromone (17)Yellow powder; UV (MeOH) lmax cm21: 233, 310 nm; 3431, 1559,1633; 1H NMR (400MHz, CD3OD): dH 6.20 (s, H-3), 7.70 (dd, J ¼ 7.6,1.6Hz, H-5), 7.25 (m, H-6), 7.23 (dd, J ¼ 7.6, 1.6Hz, H-7), 7.25 (m, H-20), 7.36 (m, H-30), 7.30 (m, H-40), 7.36 (m, H-50), 7.25 (m, H-60), 3.10 (t,J ¼ 6.5Hz, H-70), 3.03 (t, J ¼ 6.5Hz, H-80); 13C NMR (100MHz,CD3OD): dC 167.4 (C-2), 110.5 (C-3), 178.0 (C-4), 116.7 (C-5), 125.1(C-6), 118.8 (C-7), 144.6 (C-8), 145.0 (C-9), 124.3 (C-10), 139.8 (C-10),128.3 (C-20), 128.8 (C-30), 126.8 (C-40), 128.8 (C-50), 128.3 (C-60), 33.4(C-70), 35.6 (C-80); HR-ESI-MS m/z: 289.0847 [M þ Na]þ (calcd for289.0841, C17H14O3Na); Rhizomes of I. cylindrica Beauv. var. major(Nees) C. E. Hubb., family Poaceae (Xuan et al. 2013)

2-(2-Phenylethyl) chromone-8-O-b-D-glucopyranoside (18)Yellow powder; [a ]D þ8.6 (c ¼ 0.030, MeOH); UV (MeOH) lmax:233, 306 nm; IR (KBr) gmax cm21: 3450, 1578, 1494, 637; 1H NMR(400MHz, DMSO-d6): dH 6. 15 (s, H-3), 7.72 (dd, J ¼ 8.0, 1.0Hz, H-5),7.36 (t, J ¼ 8.0Hz, H-6), 7.62 (dd, J ¼ 8.0, 1.0Hz, H-7), 7.25 (m, H-20),7.25 (m, H-30), 7.16 (m, H-40), 7.25 (m, H-50), 7.25 (m, H-60), 3.13 (t,J ¼ 7.2Hz, H-70), 3.05 (t, J ¼ 7.2Hz, H-80), 5.09 (d, J ¼ 7.2Hz, H-100),3.62 (t, J ¼ 8.4 Hz, H-200), 3.51 (t, J ¼ 8.4Hz, H-300), 3.43 (t,J ¼ 8.4Hz, H-400), 3.48 (m, H-500), 3.89 (dd, J ¼ 12.0, 1.7Hz, H-600A),3.71 (dd, J ¼ 12.0, 4.9Hz, H-600B); 13C NMR (100MHz, DMSO-d6): dC171.5 (C-2), 110.7 (C-3), 180.4 (C-4), 119.2 (C-5), 126.2 (C-6), 122.1(C-7), 147.8 (C-8), 149.0 (C-9), 125.0 (C-10), 141.4 (C-10), 129.6 (C-20), 129.6 (C-30), 127.4 (C-40), 129.6 (C-50), 129.5 (C-60), 33.8 (C-70),37.0 (C-80), 103.0 (C-100), 75.0 (C-200), 78.2 (C-300), 71.3 (C-400), 78.2 (C-500), 62.5 (C-600); HR-ESI-MS m/z: 451.1371 [M þ Na]þ (calcd for451.1369, C23H24O8Na); Rhizomes of I. cylindrica Beauv. var. major(Nees) C. E. Hubb., family Poaceae (Xuan et al. 2013).

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6-Methoxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl]chromone (19)Colourless needles; mp 152–1538C; UV (MeOH) lmax (1): 228 (30241),242.0 (26636), 274 (8035), 322 (6136) nm; IR (KBr) gmax cm

21: 3200(OH), 1628, 1582 (g-pyrone), 1476, 1458, 1236, 1124, 972, 839, 824; 1HNMR (CDCl3, 300MHz): dH 6.16 (s, H-3), 7.55 (d, J ¼ 3.0Hz, H-5),7.25 (dd, J ¼ 9.0, 3.0Hz, H-7), 7.38 (d, J ¼ 9.0Hz, H-8), 6.67 (d,J ¼ 2.0Hz, H-20), 6.84 (d, J ¼ 8.0Hz, H-50), 6.70 (dd, J ¼ 8.0, 2.0Hz,H-60), 2.97 (m, H-70), 2.90 (m, H-80), 3.89 (6-OCH3), 3.82 (30-OCH3),5.61 (brs, OH); 13CNMR (CDCl3, 75MHz): dC 168.4 (C-2), 109.5 (C-3),178.2 (C-4), 104.8 (C-5), 156.8 (C-6), 123.6 (C-7), 119.2 (C-8), 151.3 (C-9), 124.2 (C-10), 131.6 (C-10), 114.5 (C-20), 144.2 (C-30), 146.5 (C-40),110.8 (C-50), 120.9 (C-60), 32.8 (C-70), 36.5 (C-80), 55.8 (6-OCH3), 55.9(30-OCH3); EI-MS m/z (rel. int.): 326 [M]þ (16.6), 310 (7.5), 190 (100),137 (29.8), 91 (32.1), 77 (5.8); HR-EI-MSm/z: 326.1149 [M]þ (calcd forC19H18O5: 326.1154); Agarwood (Aquilaria agallocha ROXB.), familyAquilariaceae (Konishi et al. 2002).

6,8-Dihydroxy-2-(2-phenylethyl)chromone (20)Colourless needles; mp 218–2208C; UV (MeOH) lmax (1): 204(25568), 244.5 (26062), 263.0 (11750), 338.0 (4254) nm; IR (KBr) gmax

cm21: 3310 (OH), 1634, 1592 (g-pyrone), 1554, 1490, 1399, 1300,1142, 852, 839; 1H NMR (C5D5N, 300MHz): dH 6.35 (s, H-3), 7.35 (d,J ¼ 2.8Hz, H-5), 7.35 (d, J ¼ 2.8Hz, H-7), 7.10–7.30 (m, H-20-60),2.94 (m, H-70), 2.81 (m, H-80), 12.30 (brs, OH), 12.70 (brs, OH); 13CNMR (C5D5N, 75MHz): dC 167.8 (C-2), 109.4 (C-3), 178.0 (C-4), 99.1(C-5), 156.5 (C-6), 109.5 (C-7), 149.4 (C-8), 140.6 (C-9), 126.4 (C-10),141.6 (C-10), 128.8 (C-20), 128.6 (C-30), 126.7 (C-40), 128.6 (C-50),128.8 (C-60), 33.1 (C-70), 35.9 (C-80); EI-MS m/z (rel. int.): 282 [M]þ

(18.2), 176 (2.4), 91 (100); HR-EI-MS m/z: 282.0898 [M]þ (calcd forC17H14O4: 282.0892)); Agarwood (A. agallocha ROXB.), familyAquilariaceae (Konishi et al. 2002).

6-Hydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (21)Colourless needles; mp 215–2188C; UV (MeOH) lmax (1): 227.5(36052), 240.0 (27427), 273 (8930), 328.5 (7003) nm; IR (KBr) gmax

cm21: 3326 (OH), 1635, 1626 (g-pyrone), 1589, 1516, 1472, 1226, 978,843, 822; 1H NMR (C5D5N, 300MHz): dH 6.35 (s, H-3), 8.06 (dd,J ¼ 2.5, 0.3Hz, H-5), 7.50 (dd, J ¼ 9.0, 2.5Hz, H-7), 7.54 (dd, J ¼ 9.0,0.3Hz, H-8), 7.15 (d, J ¼ 8.5Hz, H-30, 50), 7.22 (d, J ¼ 8.5Hz, H-20, 60),2.97 (m, H-70), 2.88 (m, H-80); 13CNMR (C5D5N, 75MHz): dC 168.6 (C-2), 109.4 (C-3), 177.8 (C-4), 109.0 (C-5), 156.2 (C-6), 123.5 (C-7), 119.8(C-8), 150.6 (C-9), 125.4 (C-10), 130.9 (C-10), 129.9 (C-20), 116.4 (C-30),157.5 (C-40), 116.4 (C-50), 129.9 (C-60), 32.4 (C-70), 36.5 (C-80); EI-MSm/z (rel. int.): 282 [M]þ (30.3), 176 (100), 147 (73), 137 (15.09), 107(69.7), 91 (33.4), 77 (14.3); HR-EI-MS m/z: 282.0895 [M]þ (calcd forC17H14O4: 282.0892); Agarwood (A. agallocha ROXB.), familyAquilariaceae (Konishi et al. 2002).

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6-Hydroxy-2-[2-(2-hydroxyphenyl)ethyl]chromone (22)Colourless needles; mp 185–1868C; UV (MeOH) lmax (1): 226.5(29174), 243.4 (23253), 274 (8434), 329 (6255) nm; IR (KBr) gmax

cm21: 3279 (OH), 1635, 1595 (g-pyrone), 1483, 1370, 1285, 1246,1208, 1034, 966, 849, 839 cm21; 1H NMR (C5D5N, 300MHz): dH 6.42(s, H-3), 8.06 (dd, J ¼ 2.5, 0.3Hz, H-5), 7.46 (dd, J ¼ 9.0, 2.5Hz, H-7),7.49 (dd, J ¼ 9.0, 0.3Hz, H-8), 6.92 (ddd, J ¼ 7.5, 7.5, 1.5Hz, H-30),7.15 (dd, J ¼ 7.5, 1.5 Hz, H-40), 7.22 (ddd, J ¼ 7.5, 7.5, 1.5Hz, H-50),7.29 (dd, J ¼ 7.5, 1.5Hz, H-60), 3.29 (m, H-70), 3.08 (m, H-80); 13CNMR (C5D5N, 75MHz): dC 169.2 (C-2), 109.3 (C-3), 177.8 (C-4),108.9 (C-5), 156.1 (C-6), 123.3 (C-7), 119.6 (C-8), 150.7 (C-9), 127.5(C-10), 128.8 (C-10), 156.8 (C-20), 115.7 (C-30), 128.1 (C-40), 119.8 (C-50), 130.6 (C-60), 32.4 (C-70), 36.5 (C-80); EI-MS m/z (rel. int.): 282[M]þ (37.7), 176 (100), 137 (29.6), 107 (22.2), 91 (20.4), 77 (12.3); HR-EI-MS m/z: 282.0888 [M]þ (calcd for C17H14O4, 282.0892); Agarwood(A. agallocha ROXB.) family Aquilariaceae (Konishi et al. 2002).

7-Hydroxy-2-(2-phenylethyl)chromone (23)Colourless needles; mp 163–1648C; UV (MeOH) lmax (1): 207 (20287),242 (13336), 249 (13424), 280 (6898), 296 (6703) nm; IR (KBr) gmax

cm21: 3326 (OH), 1636, 1576 (g-pyrone), 1456, 1395, 1250, 1175, 1093,993, 849; 1H NMR (CDCl3, 300MHz): dH 6.12 (s, H-3), 8.06 (d,J ¼ 8.6Hz, H-5), 6.95 (dd, J ¼ 8.6, 2.2Hz, H-6), 6.89 (d, J ¼ 2.2Hz, H-8), 7.17–7.32 (m, H-20-60), 3.03 (m, H-70), 2.91 (m, H-80); 13C NMR(CDCl3, 75MHz): dC 168.6 (C-2), 109.6 (C-3), 178.2 (C-4), 127.4 (C-5),114.9 (C-6), 161.8 (C-7), 102.9 (C-8), 158.4 (C-9), 115.0 (C-10), 139.7(C-10), 128.6 (C-20), 128.3 (C-30), 126.6 (C-40), 128.3 (C-50), 128.6 (C-60),33.0 (C-70), 36.0 (C-80); EI-MS m/z (rel. int.): 266 [M]þ (48.9), 249 (3.3),137 (8.5), 121 (2.2), 91 (100), 65 (4.9); HR-EI-MS m/z: 266.0940 [M]þ

(calcd for C17H14O3, 266.0943); Agarwood A. agallocha ROXB. familyAquilariaceae (Konishi et al. 2002).

6-Hydroxy-7-methoxy-2-(2-phenylethyl)chromone (24)Colourless needles; mp 187–1888C; UV (MeOH) lmax (1): 207 (34932),234 (27118), 279 (9976), 322 (10687) nm; IR (KBr) gmax cm21: 3320(OH), 1630, 1586 (g-pyrone), 1472, 1458, 1390, 1270, 1264, 1218, 1200,1197, 1082, 847 cm21; 1HNMR(C5D5N,300MHz):dH 6.32 (s,H-3), 8.12(s, H-5), 7.14 (s, H-8), 7.22–7.36 (m, H-20-60), 3.01 (m, H-70), 2.88 (m, H-80), 11.90 (brs, 6-OH), 3.98 (7-OCH3);

13C NMR (C5D5N, 75MHz): dC167.5 (C-2), 109.7 (C-3), 177.2 (C-4), 109.1 (C-5), 146.7 (C-6), 154.2 (C-7), 100.5 (C-8), 151.8 (C-9), 118.3 (C-10), 140.8 (C-10), 129.0 (C-20), 128.8(C-30), 126.8 (C-40), 128.8 (C-50), 129.0 (C-60), 33.1 (C-70), 35.9 (C-80),55.3 (7-OCH3);EI-MSm/z (rel. int.): 296 [M]þ (60.5), 190 (4.1), 167 (3.1),121 (3.8), 91 (100), 65 (4.5); HR-EI-MS m/z: 296.1041 [M]þ (calcd forC18H16O4: 296.1048); Agarwood (A. agallocha ROXB.), familyAquilariaceae (Konishi et al. 2002).

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5-Hydroxy-2-(2-phenylethyl)chromone (25)Yellow powder; UV (MeOH) lmax (log 1): 344 (3.83), 252 (4.41), 220(4.43) nm; IR (KBr) gmax cm

21: 2926, 1655, 1621, 1477, 1412, 1255,848, 805; 1H NMR (CDCl3, 300MHz): dH 6.00 (s, H-3), 6.71 (dd,J ¼ 8.4, 0.9Hz, H-6), 7.44 (t, J ¼ 8.4Hz, H-7), 6.80 (dd, J ¼ 8.4,0.9Hz, H-8), 7.12–7.27 (m, H-20-60), 2.99 (t, J ¼ 7.6Hz, H-70), 2.86 (t,J ¼ 7.6Hz, H-80); 12.45 (brs, 5-OH); 13C NMR (CDCl3, 100MHz): dC29.7 (C-70), 32.8 (C-80), 106.8 (C-8), 108.8 (C-3), 110.6 (C-10), 111.2(C-6), 126.7 (C-40), 128.2 (C-20,60), 128.7 (C-30,50), 135.2 (C-7), 139.4(C-10), 156.7 (C-9), 160.8 (C-5),169.8 (C-2), 183.5 (C-4); HR-EI-MSm/z: 266.0936 [M]þ (calcd for C17H14O3, 266.0943); Rhizomes of I.cylindrica Beauv., family Gramineae (Yoon et al. 2006).

AH3; 6-Hydroxy-2-(2-phenylethyl)chromone (26)Yellowish plates, mp 224–2258C; UV (MeOH) lmax (1): 207 (17660),226 (23437), 240 (21302), 265 (6230), 328 (5727), 332 (5828) nm; IR(KBr) gmax cm21: 3275 (OH), 1655, 1638 (g-pyrone), 1620, 1603,1583, 1465, 1400 (aromatic ring) cm21; 1H NMR (C5D5N, 300MHz):dH 6.30 (s, H-3), 8.04 (t, J ¼ 1.4Hz, H-5), 7.48 (m, H-7, 8), 7.27 (m, H-20-60), 2.92 (m, H-70), 2.92 (m, H-80), 12.13 (brs, OH); 13C NMR(C5D5N, 75MHz): dC 168.32 (C-2), 109.37 (C-3), 177.79 (C-4), 108.96(C-5), 156.24 (C-6), 123.48 (C-7), 119.61 (C-8), 150.56 (C-9), 125.29(C-10), 140.61 (C-10), 128.89 (C-20), 128.71 (C-30), 126.70 (C-40),128.71 (C-50), 128.89 (C-60), 32.95 (C-70), 35.82 (C-80); Agarwood‘Jinko’ (Aquilaria malaccensis LAM.), family Aquilariaceae (Shimadaet al. 1982).

AH4; 6-Methoxy-2-(2-phenylethyl)chromone (27)Colourless plates; mp 89–908C; UV (MeOH) lmax (1): 243 (10473),273 (6060), 321 (6766), 324 (6472) nm; IR (KBr) gmax cm21: 1652,1638 (g-pyrone), 1604, 1597, 1562, 1480, 1434 (aromatic ring); 1HNMR (C5D5N, 300MHz): dH 6.32 (s, H-3), 7.77 (d, J ¼ 3.2Hz, H-5),7.36 (m, H-7, 8), 7.27 (m, H-20-60), 2.92 (m, H-70, 80), 3.69 (6-OCH3);13C NMR (C5D5N, 75MHz): dC 168.34 (C-2), 109.61 (C-3), 177.35(C-4), 105.72 (C-5), 157.12 (C-6), 123.03 (C-7), 119.73 (C-8), 151.41(C-9), 124.91 (C-10), 140.57 (C-10), 128.91 (C-20), 128.75 (C-30),126.76 (C-40), 128.75 (C-50), 128.91 (C-60), 32.94 (C-70), 35.76 (C-80),55.61 (6-OCH3); Agarwood ‘Jinko’: (A. malaccensis LAM.), familyAquilariaceae (Shimada et al. 1982).

AH5; 6-Methoxy-2-[2-(3-methoxyphenyl)ethyl]chromone (28)Colourless plates; mp 111–1128C; UV (MeOH) lmax (1): 244 (12532),274 (10050), 321 (8512), 325 (8158) nm; IR (KBr) gmax cm

21: 1655,1640 (g-pyrone), 1610, 1600, 1587, 1483, 1467, 1433 (aromatic ring);1H NMR (C5D5N, 300MHz): dH 6.34 (s, H-3), 7.77 (d, J ¼ 3.2Hz, H-5), 7.36 (m, H-7, 8), 7.21 (m, H-20,60), 6.90 (m, H-30, 50), 2.94 (m, H-70,80), 3.68 (6-OCH3), 3.70 (30-OCH3);

13C NMR (C5D5N, 75MHz): dC168.56 (C-2), 109.64 (C-3), 177.56 (C-4), 105.75 (C-5), 157.16 (C-6),123.16 (C-7), 119.78 (C-8), 151.50 (C-9), 124.91 (C-10), 142.20 (C-10),114.59 (C-20), 160.40 (C-30), 112.34 (C-40), 129.99 (C-50), 121.03 (C-60), 33.04 (C-70), 35.79 (C-80), 55.69 (6-OCH3), 55.10 (30-OCH3);Agarwood ‘Jinko’ (A. malaccensis LAM.), family Aquilariaceae(Shimada et al. 1982).

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AH6; 6,7-Dimethoxy-2(2-phenylethyl)chromone (29)Colourless plates; mp 143–1448C; UV (MeOH) lmax (1): 212 (29247),234 (26339), 278 (9674), 317 (10597) nm; IR (KBr) gmax cm

21: 1658,1638 (g-pyrone), 1600, 1583, 1503, 1488, 1428 (aromatic ring); 1HNMR (C5D5N, 300MHz): dH 6.33 (s, H-3), 7.75 (s, H-5), 7.05 (s, H-8),7.30 (m, H-20-60), 2.95 (m, H-70, 80), 3.76 (6-OCH3), 3.86 (7-OCH3);

13CNMR (C5D5N, 75MHz): dC 167.66 (C-2), 109.84 (C-3), 176.84 (C-4),104.91 (C-5), 148.06 (C-6), 154.48 (C-7), 100.51 (C-8), 152.70 (C-9),117.44 (C-10), 140.74 (C-10), 128.97 (C-20), 128.78 (C-30), 126.77 (C-40), 128.78 (C-50), 128.97 (C-60), 33.07 (C-70), 35.82 (C-80), 55.89 (6-OCH3), 56.27 (7-OCH3); Agarwood ‘Jinko’ (A. malaccensis LAM.),family Aquilariaceae (Shimada et al. 1982).

5-Hydroxy-6-methoxy-2-(2-phenylethyl)chromone (30)Yellow needles; mp 1298C; UV (MeOH) lmax (log 1): 349 (3.43), 242(4.32), 202 (4.40) nm; IR gmax cm21: 2936, 1655, 1624, 1585, 1458,1412, 1281, 1234; 1H NMR (acetone-d6, 500MHz): dH 6.11 (s, H-3),7.39 (d, J ¼ 8.9Hz, H-7), 6.95 (d, J ¼ 8.9Hz, H-8), 7.27 (m, H-20-60),7.19 (m, H-40), 3.08 (t, J ¼ 7.1Hz, H-70), 3.01 (t, J ¼ 7.1Hz, H-80), 3.85(s, 6-OCH3), 12.77 (5-OH); 13C NMR (acetone-d6, 125MHz): dC171.76 (C-2), 108.27 (C-3), 184.80 (C-4), 150.54 (C-5), 144.18 (C-6),121.07 (C-7), 106.59 (C-8), 151.32 (C-9), 111.31 (C-10), 140.94 (C-10),129.21 (C-20, 60), 129.29 (C-30, 50), 127.15 (C-40), 33.30 (C-70), 36.40(C-80), 57.27 (6-OCH3); HR-EI-MS m/z: 296.1056 [M]þ (calcd forC18H16O4, 296.1049); Withered wood of A. sinensis Gilg, familyThymelaeaceae (Yagura et al. 2003).

Qinanone G; 6,7-dimethoxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (31)Pale yellow needles; mp 187–1898C; UV (MeOH) lmax (log 1): 207(3.48), 230 (3.32), 278 (1.51), 314 (1.20) nm; IR (KBr) gmax cm21:3448, 1633, 1513, 1477, 1383, 1272, 1084; 1H NMR (CDCl3,500MHz): dH 6.08 (s, H-3), 7.48 (s, H-5), 6.85 (s, H-8), 6.99 (d,J ¼ 8.3Hz, H-20, 60), 6.74 (d, J ¼ 8.3Hz, H-30, 50), 2.92 (m, H-70), 2.84(m, H-80), 3.93 (s, 6-OCH3), 3.96 (s, 7-OCH3);

13C NMR (CDCl3,125MHz): dC 168.2 (C-2), 109.4 (C-3), 178.0 (C-4), 104.2 (C-5), 147.5(C-6), 154.4 (C-7), 99.5 (C-8), 152.6 (C-9), 116.7 (C-10), 130.8 (C-10),129.2 (C-20, 60), 115.4 (C-30, 50), 155.1 (C-40), 32.2 (C-70), 36.3 (C-80),56.4 (6-OCH3), 56.2 (7-OCH3); HR-EI-MS m/z: 326.1161 [M]þ (calcdfor C19H18O5, 326.1154); Chinese Agarwood ‘Qi-Nan’ (A. sinensis),family Thymelaeaceae (Yang et al. 2014).

6-Hydroxy-2-(2-hydroxy-2-phenylethyl)chromone (32)White powder; mp 96–988C; [a ]D 23.08 (c ¼ 0.66, MeOH); UV(MeOH) lmax (log 1): 328 (3.83), 240 (4.41), 228 (4.43) nm; IR gmax

cm21: 3233, 1628, 1582, 1474, 1404, 1362, 1327, 1234, 1196; 1H NMR(C5D5N, 500MHz): dH 6.59 (s, H-3), 8.02 (brs, H-5), 7.44 (m, H-7, 8),7.69 (d, J ¼ 7.3Hz, H-20-60), 7.39 (t, J ¼ 7.3Hz, H-30, 50), 7.29 (t,J ¼ 7.3Hz, H-40), 5.53 (dd, J ¼ 8.7, 4.6Hz, H-70), 3.14 (dd, J ¼ 14.3,4.6Hz, H-80A), 3.20 (dd, J ¼ 14.3, 8.7Hz, H-80B); 13C NMR (C5D5N,125 MHz): dC 166.98 (C-2), 111.11 (C-3), 177.77 (C-4), 108.96 (C-5),156.21 (C-6), 123.48 (C-7), 119.80 (C-8), 150.69 (C-9), 125.47 (C-10),145.78 (C-10), 126.41 (C-20, 60), 128.77 (C-30, 50), 127.73 (C-40), 71.37(C-70), 45.26 (C-80); HR-EI-MS m/z: 282.0898 [M]þ (calcd forC17H14O4: 282.0892); Withered wood of A. sinensis GILG, familyThymelaeaceae (Yagura et al. 2003).

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2-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]chromone (33)Pale yellow amorphous solid; [a ]D þ126 (c ¼ 0.04, MeOH); UV(MeOH) lmax (log 1): 224 (2.29), 264 (0.68), 296 (0.59), 304 (sh) nm;IR (KBr) gmax cm

21: 3437, 1635, 1463, 1386, 1255; 1H NMR (CD3OD,500 MHz): dH 6.24 (s, H-3), 8.09 (dd, J ¼ 8.3, 1.6Hz, H-5), 7.46 (ddd,J ¼ 8.0, 7.2, 1.0Hz, H-6), 7.77 (ddd, J ¼ 8.4, 7.2, 1.6Hz, H-7), 7.56 (d,J ¼ 8.4Hz, H-8), 7.23 (d, J ¼ 8.5Hz, H-20, 60), 6.75 (d, J ¼ 8.5Hz, H-30, 50), 5.08 (dd, J ¼ 8.2, 5.5Hz, H-70), 3.10 (dd, J ¼ 14.3, 8.2Hz, H-80A), 3.04 (dd, J ¼ 14.3, 5.5Hz, H-80B); 13C NMR (CD3OD, 125MHz):dC 169.7 (C-2), 112.0 (C-3), 180.6 (C-4), 126.1 (C-5), 126.5 (C-6),135.4 (C-7), 109.4 (C-8), 158.1 (C-9), 124.4 (C-10), 135.6 (C-10), 128.2(C-20, 60), 116.2 (C-30, 50), 158.2 (C-40), 72.4 (C-70), 45.2 (C-80); HR-ESI-MS m/z: 283.0967 [M þ H]þ (calcd for C17H15O4, 283.0970);Chinese Agarwood ‘Qi-Nan’ (A. sinensis), family Thymelaeaceae(Yang et al. 2014).

2-[2-Hydroxy-2-(4-methoxyphenyl)ethyl]chromone (34)Pale yellow amorphous solid; [a ]D 23 (c ¼ 0.04, MeOH); UV(MeOH) lmax (log 1): 210 (2.18), 223 (2.12), 264 (0.63), 296 (0.54), 306(sh) nm; IR (KBr) gmax cm21: 3437, 1601, 1458; 1H NMR (CD3OD,500MHz): dH 6.23 (s, H-3), 8.15 (dd, J ¼ 7.9, 1.5Hz, H-5), 7.38 (ddd,J ¼ 7.5, 7.2, 1.0Hz, H-6), 7.66 (ddd, J ¼ 8.4, 7.2, 1.5Hz, H-7), 7.44 (d,J ¼ 8.4Hz, H-8), 7.36 (d, J ¼ 8.6Hz, H-20, 60), 6.91 (d, J ¼ 8.6Hz, H-30, 50), 5.18 (dd, J ¼ 8.4, 5.0Hz, H-70), 3.09 (dd, J ¼ 14.5, 8.4Hz, H-80A), 2.99 (dd, J ¼ 14.5, 5.0Hz, H-80B), 3.82 (s, 40-OCH3);

13C NMR(CD3OD, 125MHz): dC 166.1 (C-2), 111.7 (C-3), 178.2 (C-4), 125.0(C-5), 125.6 (C-6), 133.5 (C-7), 117.8 (C-8), 156.4 (C-9), 123.7 (C-10),135.0 (C-10), 127.0 (C-20, 60), 114.1 (C-30, 50), 159.5 (C-40), 71.5 (C-70),44.2 (C-80), 55.3 (40-OCH3); HR-ESI-MS m/z: 297.1121 [M þ H]þ

(calcd for C18H17O4, 297.1127); Chinese Agarwood ‘Qi-Nan’(A. sinensis), family Thymelaeaceae (Yang et al. 2014).

Aquilarone G; 40,6-dihydroxy-30,7-dimethoxy-2-(2-phenyl)ethylchromone (35)Pale yellow amorphous powder; UV (MeOH) lmax (log 1): 210 (4.54),231 (4.43), 281 (4.02), 322 (3.99) nm; IR (KBr) gmax cm

21: 3415, 1636,1567, 1518, 1459; 1H NMR (DMSO-d6, 500MHz): dH 6.03 (s, H-3),7.23 (s, H-5), 7.11 (s, H-8), 6.78 (d, J ¼ 2.0Hz, H-20), 6.64 (d,J ¼ 8.0Hz, H-50), 6.60 (dd, J ¼ 8.0, 2.0Hz, H-60), 2.87 (m, H-70), 2.87(m, H-80), 3.88 (7-OCH3), 3.67 (30-OCH3), 8.72 (brs, 40-OH), 9.71 (6-OH); 13C NMR (DMSO-d6, 125MHz): dC 167.7 (C-2), 108.7 (C-3),176.0 (C-4), 107.2 (C-5), 144.9 (C-6), 153.4 (C-7), 100.3 (C-8), 150.9(C-9), 116.5 (C-10), 130.8 (C-10), 112.5 (C-20), 147.4 (C-30), 144.8 (C-40), 115.3 (C-50), 120.4 (C-60), 31.8 (C-70), 35.2 (C-80), 56.1 (7-OCH3),55.4 (30-OCH3); HR-ESI-MS m/z: 343.117 (calcd for C19H19O6

[M þ H]þ, 343.1181); Resinous wood of A. sinensis (Lour.) Gilg,family Thymelaeaceae (Chen et al. 2012).

Aquilarone H; 40-hydroxy-6-methoxy-2-(2-phenyl)ethylchromone (36)White amorphous powder; UV (MeOH) lmax (log 1): 226 (4.43), 240(4.41), 328 (3.74) nm; IR (KBr) gmax cm

21: 3339, 1633, 1606, 1592,1482; 1H NMR (DMSO-d6, 500MHz): dH 6.14 (s, H-3), 7.36 (d,J ¼ 2.0Hz, H-5), 7.34 (dd, J ¼ 8.8, 2.0Hz, H-7), 7.56 (d, J ¼ 8.8Hz,H-8), 7.01 (d, J ¼ 8.5Hz, H-20, 60), 6.65 (d, J ¼ 8.5Hz, H-30, 50), 2.88(m, H-70), 2.87 (m, H-80), 3.82 (6-OCH3), 9.20 (40-OH); 13C NMR(DMSO-d6, 125MHz): dC 168.7 (C-2), 108.9 (C-3), 176.5 (C-4), 104.7(C-5), 156.3 (C-6), 122.9 (C-7), 119.7 (C-8), 150.6 (C-9), 123.7 (C-10),130.0 (C-10), 129.2 (C-20), 115.1 (C-30), 155.7 (C-40), 115.1 (C-50),129.1 (C-60), 31.3 (C-70), 35.2 (C-80), 55.6 (6-OCH3); HR-ESI-MS m/z:297.1121 (calcd for C18H17O4 [M þ H]þ, 297.1130); Resinous wood ofA. sinensis (Lour.) Gilg, family Thymelaeaceae (Chen et al. 2012).

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https://www.researchgate.net/publication/264360827_Nine_2-(2-Phenylethyl)chromone_Derivatives_from_the_Resinous_Wood_of_Aquilaria_sinensis_and_Their_Inhibition_of_LPS-Induced_NO_Production_in_RAW_264.7_Cells?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==


Aquilarone I; 30,6-dihydroxy-40-methoxy-2-(2-phenyl)ethylchromone (37).Yellow amorphous powder; UV (MeOH) lmax (log 1): 226 (4.46), 274(3.92), 328 (3.78) nm; IR (KBr) gmax cm

21: 3061, 1628, 1584, 1505,1475; 1H NMR (DMSO-d6, 400MHz): dH 6.0 (s, H-3), 7.24 (d,J ¼ 2.0Hz, H-5), 7.18 (dd, J ¼ 8.8, 2.0Hz, H-7), 7.47 (d, J ¼ 8.8Hz,H-8), 6.64 (d, J ¼ 2.0Hz, H-20), 6.78 (d, J ¼ 8.2Hz, H-50), 6.58 (dd,J ¼ 8.2, 2.0Hz, H-60), 2.88 (m, H-70), 2.85 (m, H-80), 3.69 (s, 40-OCH3),8.79 (brs, 30-OH), 10.29 (brs, 6-OH); 13C NMR (DMSO-d6, 100MHz):dC 168.4 (C-2), 108.6 (C-3), 176.6 (C-4), 107.4 (C-5), 154.6 (C-6),122.7 (C-7), 119.4 (C-8), 149.6 (C-9), 123.9 (C-10), 132.5 (C-10), 115.6(C-20), 146.3 (C-30), 146.0 (C-40), 112.2 (C-50), 118.7 (C-60), 31.4 (C-70),35.0 (C-80), 55.6 (40-OCH3); HR-ESI-MS m/z: 313.1070 (calcd forC18H17O5 [M þ H]þ, 313.1075); Resinous wood of A. sinensis (Lour.)Gilg, family Thymelaeaceae (Chen et al. 2012).

6-Methoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone (38)Yellow amorphous solid; UV (MeOH) lmax (log 1): 201(4.26), 226(2.97), 273 (0.73), 321 (0.53) nm; IR gmax cm21: 3429, 2928, 1637,1481, 1374, 1278, 1209, 1029; 1H NMR (CDCl3, 500MHz): dH 6.16 (s,H-3), 7.54 (d, J ¼ 3.0Hz, H-5), 7.24 (dd, J ¼ 9.1, 3.0Hz, H-7), 7.38 (d,J ¼ 9.1Hz, H-8), 6.81 (d, J ¼ 1.6Hz, H-20), 6.75 (d, J ¼ 8.2Hz, H-50),6.69 (dd, J ¼ 8.2, 1.6Hz, H-60), 2.97 (m, H-70), 2.90 (m, H-80), 3.88 (s,6-OCH3), 3.85 (s, 40-OCH3), 5.72 (brs, 30-OH); 13C NMR (CDCl3,125MHz): dC 168.4 (C-2), 109.6 (C-3), 178.3 (C-4), 104.9 (C-5), 156.9(C-6), 123.7 (C-7), 119.3 (C-8), 151.4 (C-9), 124.4 (C-10), 133.7 (C-10),114.6 (C-20), 145.6 (C-30), 145.2 (C-40), 111.0 (C-50), 119.8 (C-60), 32.5(C-70), 36.3 (C-80), 56.0 (6-OCH3), 55.9 (40-OCH3); HR-EI-MS m/z:326.1158 [M]þ (calcd for C19H18O5, 326.1154); Chinese Agarwood(A. sinensis), family Thymelaeaceae (Li et al. 2014).

5-Hydroxy-6-methoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]chromone (39)Yellow amorphous solid; UV (MeOH) lmax (log 1) 193 (3.79), 218(1.40), 234 (1.82), 304 (0.12) nm; IR gmax cm21: 3409, 1624, 1511,1480, 1457, 1278, 1234; 1H NMR (CDCl3, 500MHz): dH 6.00 (s, H-3),6.21 (d, J ¼ 9.0Hz, H-7), 6.87 (d, J ¼ 9.0Hz, H-8), 6.77 (d, J ¼ 2.0Hz,H-20), 6.75 (d, J ¼ 8.2Hz, H-50), 6.63 (dd, J ¼ 8.2, 2.0Hz, H-60), 2.87(m, H-70), 2.92 (m, H-80), 3.92 (s, 6-OCH3), 3.86 (s, 40-OCH3), 12.70(brs, 12-OH), 5.64 (brs, 30-OH); 13C NMR (CDCl3, 125MHz): dC 170.3(C-2), 108.0 (C-3), 184.1 (C-4), 149.5 (C-5), 143.4 (C-6), 119.1 (C-7),105.8 (C-8), 150.6 (C-9), 110.9 (C-10), 132.8 (C-10), 114.5 (C-20), 145.8(C-30), 145.4 (C-40), 110.9 (C-50), 119.8 (C-60), 32.4 (C-70), 36.4 (C-80),57.1 (6-OCH3), 56.1 (4

0-OCH3); HR-EI-MS m/z: 342.1101 [M]þ (calcdfor C19H18O6, 342.1103); Chinese Agarwood (A. sinensis), familyThymelaeaceae (Li et al. 2014).

2-(2-40-Methoxyphenylethyl)chromone (40)Pale yellow viscous oil; IR gmax cm

21: 1644, 1606, 1510, 1460, 1380;1H NMR (CDCl3, 80MHz): dH 6.11 (s, H-3), 8.17 (m, H-5), 7.19 (m, H-6-8, 20-60), 2.92 (m, H-70, 80), 3.75 (s, 40-OCH3);

13C NMR (CDCl3,20MHz): dC 168.50 (C-2), 110.21 (C-3), 178.10 (C-4), 124.92 (C-5),125.66 (C-6), 133.42 (C-7), 117.81 (C-8), 156.46 (C-9), 123.79 (C-10),131.75 (C-10), 129.24 (C-20, 60), 114.06 (C-30, 50), 158.32 (C-40), 32.07(C-70), 36.30 (C-80), 55.16 (40-OCH3); HR-EI-MS m/z: 280.1080 (calcdfor C18H16O3, 280.1098); Japanese Agarwood (A. sinensis), familyThymelaeaceae (Hashimoto et al. 1985).

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AH7; 5,8-Dihydroxy-2-(2-phenylethyl)chromone (41)Yellowish needles; mp 198–2018C; UV (EtOH) lmax (1) 240.5 (15125),300 (1681), 358.5 (2581) nm; IR (KBr) gmax cm

21: 3120 (OH), 1655,1615, 1586 (g-pyrone ring), 852, 822, 749 (phenyl); 1H NMR (CDCl3,400MHz): dH 6.05 (s, H-3), 6.66 (d, J ¼ 8.8Hz, H-6), 7.14 (d,J ¼ 8.8Hz, H-7), 2.92 (m, 70, 80), 7.25 (m, H-20-60), 11.64 (s, 5-OH),1.56 (s, 8-OH); 13C NMR (CDCl3, 100MHz): dC 170.14 (C-2), 108.82(C-3), 183.94 (C-4), 158.71 (C-5), 110.53 (C-6), 122.74 (C-7), 138.90(C-8), 152.92 (C-9), 111.51 (C-10), 140.23 (C-10), 128.84 (C-20, 60),128.57 (C-30, 50), 126.75 (C-40), 35.69 (C-70), 32.72 (C-80); KalimantanAgalwood (A. sinensis ‘Jinko’), family Aquilariaceae (Iwagoe et al.1988).

AH8; 6,7-Dimethoxy-2-[2-(4-methoxyphenyl)ethyl]chromone (42)Yellowish needles; mp 139–1408C; UV (MeOH) lmax (1) 230 (31672),316 (10999) nm; IR (KBr) gmax cm

21: 1640, 1600 (g-pyrone ring), 831(phenyl); 1H NMR (C5D5N, 400MHz): dH 6.35 (s, H-3), 6.94, 7.25 (dt,J ¼ 8.7, 3.0, 3.0Hz, aromatic H), 7.07 (s, H-8), 7.77 (s, H-5), 2.93 (m,70, 80), 3.66, 3.76, 3.86 (s, 40,6,7-OCH3);

13C NMR (C5D5N, 100MHz):dC 168.82 (C-2), 109.65 (C-3), 178.06 (C-4), 104.70 (C-5), 148.09 (C-6), 155.08 (C-7), 100.47 (C-8), 152.99 (C-9), 116.96 (C-10), 132.59 (C-10), 129.83 (C-20, 60), 114.50 (C-30, 50), 148.09 (C-40), 36.06 (C-70),32.16 (C-80), 55.32, 56.14, 56.58 (40,6,7-OCH3); Kalimantan Agalwood(A. sinensis ‘Jinko’) family Aquilariaceae (Iwagoe et al. 1988).

7-Hydroxy-6-methoxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (43)Brown amorphous powder; UV (MeOH) lmax (log 1): 317 (3.65), 278(3.71), 228 (4.15), 205 (4.18) nm; IR (KBr) gmax cm21: 2929, 1736,1637, 1513, 1475, 1383, 1279, 1247, 1217, 1179, 1116, 1081, 1034; 1HNMR (CDCl3, 500MHz): dH 6.06 (s, H-3), 7.52 (s, H-5), 6.93 (s, H-8),7.09 (d, J ¼ 8.6Hz, H-20, 60), 6.80 (d, J ¼ 8.6Hz, H-30, 50), 2.96 (dd,J ¼ 8.2, 7.2Hz, H-70), 2.85 (dd, J ¼ 8.2, 7.2Hz, H-80), 3.97 (6-OCH3),3.76 (s, 40-OCH3);

13C NMR (CDCl3, 125MHz): dC 167.9 (C-2), 109.4(C-3), 177.7 (C-4), 104.3 (C-5), 145.1 (C-6), 151.2 (C-7), 102.7 (C-8),152.8 (C-9), 117.0 (C-10), 131.8 (C-10), 129.2 (C-20, 60), 114.0 (C-30, 50),158.2 (C-40), 32.2 (C-70), 36.5 (C-80), 56.5 (6-OCH3), 55.3 (40-OCH3);HR-ESI-MSm/z: 327.1232 (calcd for C19H19O

þ5 [M þ H]þ , 327.1227);

Agarwood chips of A. malaccensis (AM), family Thymelaeaceae(Wu et al. 2012).

5-Hydroxy-6-methoxy-2-[2-(2-hydroxyphenyl)ethyl]chromone (44)Yellow needles; mp 175–1768C; 1H NMR (acetone-d6, 300MHz): dH6.10 (s, H-3), 7.43 (d, J ¼ 9.0Hz, H-7), 6.98 (d, J ¼ 9.0Hz, H-8), 6.87(d, J ¼ 7.5Hz, H-30), 7.07 (t, J ¼ 7.5Hz, H-40), 6.67 (t, J ¼ 7.5Hz, H-50), 7.15 (d, J ¼ 7.5Hz, H-60), 3.08 (t, J ¼ 6.0Hz, H-70), 3.02 (t,J ¼ 6.0Hz, H-80), 3.90 (6-OCH3), 12.85 (s, 5-OH), 8.52 (s, 2

0-OH); 13CNMR (acetone-d6, 75MHz): dC 172.4 (C-2), 108.0 (C-3), 184.8 (C-4),151.4 (C-5), 144.1 (C-6), 121.0 (C-7), 106.7 (C-8), 150.5 (C-9), 111.3(C-10), 127.0 (C-10), 156.0 (C-20), 115.8 (C-30), 128.4 (C-40), 120.3 (C-50), 130.9 (C-60), 28.4 (C-70), 34.9 (C-80), 57.3 (6-OCH3); ESI-MS m/z:313 [M þ H]þ; B. ischaemum L., family Gramineae (Wang et al. 2001).

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https://www.researchgate.net/publication/264328872_Eight_New_2-(2-Phenylethyl)chromone_(2-(2-Phenylethyl)-4H-1-benzopyran-4-one)_Derivatives_from_Aquilaria_malaccensis_Agarwood?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==


5-Hydroxy-2-[2-(2-hydroxyphenyl)ethyl]chromone (45)Light yellow needles; mp 172–1748C ; 1H NMR (DMSO-d6, 500MHz):dH 6.24 (s, H-3), 6.78 (d, J ¼ 8.1Hz, H-6), 7.63 (dd, J ¼ 8.4, 8.1Hz, H-7), 7.00 (d, J ¼ 8.4Hz, H-8), 6.87 (d, J ¼ 7.5Hz, H-30), 7.07 (t,J ¼ 7.5Hz, H-40), 6.67 (t, J ¼ 7.5Hz, H-50), 7.15 (d, J ¼ 7.5Hz, H-60),2.94 (s, H-70), 2.94 (s, H-80), 12.64 (s, 5-OH), 9.41 (s, 20-OH); 13C NMR(DMSO-d6,75MHz): dC 171.4 (C-2), 108.2 (C-3), 182.9 (C-4), 156.3(C-5), 110.8 (C-6), 135.8 (C-7), 107.3 (C-8), 159.9 (C-9), 109.8 (C-10),125.8 (C-10), 155.2 (C-20), 115.0 (C-30), 127.5 (C-40), 119.0 (C-50),129.9 (C-60), 27.1 (C-70), 33.6 (C-80): EI-MS m/z: 282 [M]þ; B.ischaemum L., family Gramineae (Wang et al. 2001).

Oxidoagarochromone A; 5,6:7,8-diepoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone (46)Brown gum; [a ]D 21.3 (c ¼ 0.35, MeOH); UV (MeOH) lmax (log 1):254 (4.11), 208 (4.39) nm; IR gmax cm21: 1658, 1620, 1466, 1404,1192; 1H NMR (CDCl3, 500MHz): dH 6.18 (s, H-3), 4.35 (d,J ¼ 3.3Hz, H-5), 3.84 (t, J ¼ 3.3Hz, H-6), 3.98 (t, J ¼ 3.3Hz, H-7),3.82 (d, J ¼ 3.3Hz, H-8), 7.19 (d, J ¼ 8.3Hz, H-20), 7.31 (m, H-30),7.24 (t, J ¼ 7.3Hz, H-40), 7.19 (m, H-50), 7.19 (d, J ¼ 8.3Hz, H-60),2.99 (m, H-70), 2.87 (t, J ¼ 7.6Hz, H-80); 13C NMR (CDCl3, 125MHz):dC 168.1 (C-2), 114.2 (C-3), 177.5 (C-4), 46.9 (C-5), 46.5 (C-6), 48.7(C-7), 47.7 (C-8), 161.1 (C-9), 120.8 (C-10), 139.2 (C-10), 128.2 (C-20),128.8 (C-30), 126.8 (C-40), 128.8 (C-50), 128.2 (C-60), 32.9 (C-70), 35.3(C-80); HR-FAB-MS m/z: 283.0976 [M þ H]þ (calcd for C17H15O4;283.0970); A. crassna Pierre ex Lecomte, family Thymelaeaceae(Yagura et al. 2005).

Oxidoagarochromone B; 5,6:7,8-diepoxy-2-[2-(4-methoxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (47)Pale yellow prisms; mp 142–144 8C; [a ]D þ 0.3 (c ¼ 0.31, MeOH); UV(MeOH) lmax (log1): 254 (4.06), 223 (4.33), 203 (4.37) nm; IR (KBr) gmax

cm21: 1658, 1620, 1512, 1462, 1404, 1246, 1192; 1H NMR (CDCl3, 500,MHz): dH 6.16 (s, H-3), 4.35 (d, J ¼ 3.4Hz,H-5), 3.84 (t, J ¼ 3.4Hz,H-6),3.98 (t, J ¼ 3.3Hz, H-7), 3.83 (d, J ¼ 3.4Hz, H-8), 7.09 (d, J ¼ 8.8Hz, H-20), 6.84 (d, J ¼ 8.8Hz, H-30), 6.84 (d, J ¼ 8.8Hz, H-50), 7.09 (d,J ¼ 8.8Hz, H-60), 2.94 (m, H-70), 2.83 (m, H-80), 3.79 (s, 40-OCH3);

13CNMR (CDCl3, 125MHz): dC 168.2 (C-2), 114.2 (C-3), 177.5 (C-4), 46.9(C-5), 46.5 (C-6), 48.6 (C-7), 47.7 (C-8), 161.1 (C-9), 120.8 (C-10), 131.2(C-10), 129.2 (C-20), 114.1 (C-30), 158.4 (C-40), 114.1 (C-50), 129.2 (C-60),32.0 (C-70), 35.6 (C-80), 55.3 (40-OCH3); HR-FAB-MS m/z: 313.1068[M þ H]þ (calcd for C18H17O5; 313.1076); A. crassna Pierre ex Lecomte,family Thymelaeaceae (Yagura et al. 2005).

Oxidoagarochromone C; 5,6:7,8-diepoxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-5,6,7,8-tetrahydro-chromone (48)

Pale yellow crystalline solid; mp 69–728C; [a ]D 211.8 (c ¼ 0.59,CHCl3); UV (MeOH) lmax (log 1): 254 (3.97), 207 (4.42) nm; IR (KBr)gmax cm21: 3217, 1659, 1612, 1512, 1466, 1408, 1273, 1242, 1196,1130; 1H NMR (CDCl3, 500MHz): dH 6.15 (s, H-3), 4.34 (d,J ¼ 3.3Hz, H-5), 3.84 (t, J ¼ 3.3Hz, H-6), 3.98 (t, J ¼ 3.3 Hz, H-7),3.84 (d, J ¼ 3.3Hz, H-8), 6.76 (d, J ¼ 2.2Hz, H-20), 6.77 (d,J ¼ 8.4Hz, H-50), 6.63 (d, J ¼ 8.3, 2.2Hz, H-60), 2.90 (m, H-70), 2.83(m, H-80), 3.87 (s, 40-OCH3), 5.65 (s, 3-OH); 13C NMR(CDCl3,125MHz): dC 168.2 (C-2), 114.2 (C-3), 177.6 (C-4), 46.9 (C-5), 46.4 (C-6), 48.6 (C-7), 47.7 (C-8), 161.1 (C-9), 120.8 (C-10), 132.4(C-10), 114.3 (C-20), 145.8 (C-30), 145.4 (C-40), 110.8 (C-50), 119.7 (C-60), 32.2 (C-70), 35.4 (C-80), 56.0 (40-OCH3); HR-FAB-MS m/z:329.1031 [M þ H]þ (calcd for C18H17O6; 329.1025); A. crassna Pierreex Lecomte, family Thymelaeaceae (Yagura et al. 2005).

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5,6-Epoxy-7b-hydroxy-8b-methoxy-2-(2-phenylethyl)chromone (49)Brown amorphous solid; [a ]D 251.0 (c ¼ 0.80, MeOH); UV (MeOH)lmax (log 1) 203 (4.12), 220 (2.89), 259 (1.07) nm; IR gmax cm

21: 3437,2925, 2858, 1661, 1614, 1452, 1409, 1094; 1H NMR (CD3COCD3, 500MHz): dH 6.10 (s, H-3), 3.75 (d, J ¼ 4.3Hz, H-5), 3.63 (dd, J ¼ 4.3,2.0Hz, H-6), 4.03 (d, J ¼ 4.7Hz, H-7), 4.45 (dd, J ¼ 4.7, 2.0Hz, H-8),7.19 (m, H-20), 7.30 (m, H-30), 7.23 (m, H-40), 7.30 (m, H-50), 7.19 (m,H-60), 3.00 (m, H-70), 2.89 (m, H-80), 3.34 (s, 8-OCH3);

13C NMR(CD3COCD3, 125MHz): dC 168.9 (C-2), 114.8 (C-3), 178.0 (C-4), 50.3(C-5), 58.0 (C-6), 68.8 (C-7), 71.0 (C-8), 165.5 (C-9), 121.8 (C-10),141.1 (C-10), 129.2 (C-20), 129.3 (C-30), 127.2 (C-40), 129.3 (C-50),129.2 (C-60), 33.3 (C-70), 35.5 (C-80), 60.6 (8-OCH3); HR-ESI-MS m/z:337.1046 [M þ Na]þ (calcd for C18H18O5Na, 337.1052); ChineseAgarwood of A. sinensis, family Thymelaeaceae (Li et al. 2014).

rel-(1aR,2R,3R,7bS)-1a,2,3,7b-Tetrahydro-2,3-dihydroxy-5-[2-(4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzopyran-7-one (50)

Pale yellow amorphous powder; [a ]D þ18 (c ¼ 0.178, MeOH); UV(MeOH) lmax (log 1): 253 (4.00), 223 (4.18), 203 (4.23) nm; IR (KBr)gmax cm

21: 3398, 1658, 1600, 1513, 1458, 1247, 1184, 1060; 1H NMR(CDCl3, 500MHz): dH 6.10 (s, H-3), 3.76 (d, J ¼ 4.4Hz, H-5), 3.83 (d,J ¼ 4.4Hz, H-6), 4.10 (d, J ¼ 7.7Hz, H-7), 4.69 (d, J ¼ 7.7Hz, H-8),7.06 (d, J ¼ 8.5Hz, H-20-60), 6.83 (d, J ¼ 8.5Hz, H-30-50), 2.91 (m, H-70), 2.82 (m, H-80), 3.77 (40-OCH3);

13C NMR (CDCl3, 125MHz): dC169.2 (C-2), 114.2 (C-3), 180.8 (C-4), 49.5 (C-5), 54.8 (C-6), 72.8 (C-7), 69.0 (C-8), 158.5 (C-9), 120.3 (C-10), 131.1 (C-10), 129.1 (C-20, 60),114.2 (C-30, 50), 158.4 (C-40), 32.0 (C-70), 35.4 (C-80), 55.3 (40-OCH3);HR-FAB-MS m/z: 331.1187 (calcd for C18H19O

þ6 [M þ H]þ,

331.1182); Agarwood chips of A. malaccensis (AM), familyThymelaeaceae (Wu et al. 2012).

rel-(1aR,2R,3R,7bS)-1a,2,3,7b-Tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7H-oxireno [f] [1]benzopyran-7-one (51)

White amorphous powder; [a ]D 238.9 (c ¼ 0.141, MeOH); UV(MeOH) lmax (log 1): 253 (4.03), 205 (4.24) nm; IR (KBr) gmax cm

21:3265, 2917, 1651, 1573, 1456, 1187, 1010; 1H NMR (CDCl3,500MHz): dH 6.12 (s, H-3), 3.76 (d, J ¼ 4.2Hz, H-5), 3.83 (d,J ¼ 4.2Hz, H-6), 4.10 (d, J ¼ 7.7Hz, H-7), 4.69 (d, J ¼ 7.7Hz, H-8),7.16 (m, H-20, 60), 7.30 (m, H-30, 50), 7.22 (m, H-40), 2.98 (m, H-70), 2.86(m, H-80); 13C NMR (CDCl3, 125MHz): dC 169.0 (C-2), 114.2 (C-3),180.7 (C-4), 49.5 (C-5), 54.7 (C-6), 72.9 (C-7), 69.0 (C-8), 158.5 (C-9),120.3 (C-10), 139.1 (C-10), 128.2 (C-20, 60), 128.8 (C-30, 50), 126.8 (C-40), 32.9 (C-70), 35.1 (C-80); HR-ESI-MS m/z: 301.1066 (calcd forC17H17O

þ5 [M þ H]þ, 301.1071); Agarwood chips of A. malaccensis

(AM), family Thymelaeaceae (Wu et al. 2012).

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rel-(1aR,2R,3R,7bS)-1a,2,3,7b-Tetrahydro-2,3-dihydroxy-5-[2-(3-hydroxy-4-methoxy phenyl) ethyl]-7H-oxireno[f] [1]benzopyran-7-one (52).

Brown amorphous powder; [a ]D þ60.9 (c ¼ 0.183, MeOH); UV(MeOH) lmax (log 1): 204 (4.47) nm; IR (KBr) gmax cm

21: 3388, 2931,1658, 1604, 1513, 1442, 1246, 1186, 1131, 1032.1; 1H NMR (CDCl3,500MHz): dH 6.10 (s, H-3), 3.77 (d, J ¼ 4.2Hz, H-5), 3.83 (d,J ¼ 4.2Hz, H-6), 4.10 (d, J ¼ 7.8Hz, H-7), 4.69 (d, J ¼ 7.8Hz, H-8),6.74 (d, J ¼ 1.6Hz, H-20), 6.75 (d, J ¼ 8.0Hz, H-50), 6.60 (dd, J ¼ 8.0,1.6Hz, H-60), 2.88 (m, H-70), 2.82 (m, H-80), 3.85 (s, 40-OCH3);

13CNMR (CDCl3, 125MHz): dC 169.2 (C-2), 114.2 (C-3), 180.8 (C-4), 49.5(C-5), 54.8 (C-6), 72.9 (C-7), 69.0 (C-8), 158.5 (C-9), 120.3 (C-10),132.3 (C-10), 114.3 (C-20), 145.8 (C-30), 145.4 (C-40), 110.8 (C-50),119.6 (C-60), 32.2 (C-70), 35.2 (C-80), 56.0 (40-OCH3); HR-ESI-MS m/z:347.1110 (calcd for C18H19O

þ7 [M þ H]þ, 347.1125); Agarwood chips

of A. malaccensis (AM), family Thymelaeaceae (Wu et al. 2012).

8-Chloro-5,6,7-trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (53)White amorphous powder; mp 102–1048C; [a ]D 217.9 (c ¼ 1.6,MeOH); IR (KBr) gmax cm

21: 3404, 1651, 1574,1513, 1451; 1H NMR(CD3OD, 400MHz): dH 6.14 (s, H-3), 4.77 (d, J ¼ 4.3Hz, H-5), 4.05(dd, J ¼ 4.3, 1.8Hz, H-6), 4.23 (dd, J ¼ 7.5, 1.8Hz, H-7), 4.86 (d,J ¼ 7.5Hz, H-8), 6.68 (d, J ¼ 1.5Hz, H-20), 6.81 (d, J ¼ 8.2Hz, H-50),6.63 (d, J ¼ 8.2, 1.5Hz, H-60), 2.89 (t, J ¼ 7.1Hz, H-70), 2.88 ((t,J ¼ 7.1Hz, H-80), 3.79 (s, 40-OCH3);

13C NMR (CD3OD, 100MHz): dC171.5 (C-2), 114.3 (C-3), 181.6 (C-4), 66.5 (C-5), 73.6 (C-6), 73.5 (C-7), 58.0 (C-8), 161.1 (C-9), 122.8 (C-10), 133.9 (C-10), 116.4 (C-20),147.4 (C-30), 147.7 (C-40), 113.1 (C-50), 120.7 (C-60), 33.1 (C-70), 36.3(C-80), 56.6 (40-OCH3); HR-ESI-MS m/z: 405.0720 [M þ Na]þ (calcdfor C18H19O7NaCl; 405.0717); Chinese Eaglewood (A. sinensis (Lour.)Gilg) family Thymelaeaceae (Liu et al. 2008).

(5S,6R,7S)-5,6,7-Trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (54)A white amorphous powder; mp 90–928C; [a ]D248 (c ¼ 0.5, MeOH);IR (KBr) gmax cm

21: 3403, 2464, 1659, 1583, 1514, 1452, 1280, 1069;1HNMR (CD3OD, 400MHz): dH 6.09 (s, H-3), 4.45 (d, J ¼ 4.6Hz,H-5),3.68 (dd, J ¼ 6.9, 4.6Hz, H-6), 3.90 (m, H-7), 2.83 (dd, J ¼ 17.8, 4.9Hz,H-8A), 2.55 (dd, J ¼ 17.8, 5.1Hz,H-8B), 6.66 (d, J ¼ 2.0Hz,H-20), 6.80(d, J ¼ 8.2Hz, H-50), 6.59 (d, J ¼ 8.2, 2.0Hz, H-60), 2.76 (overlapped,H-70), 2.76 (overlapped, H-80), 3.71 (s, 40-OCH3);

13C NMR (CD3OD,100MHz): dC 168.0 (C-2), 112.7 (C-3), 178.4 (C-4), 67.0 (C-5), 71.8 (C-6), 67.2 (C-7), 33.0 (C-8), 161.5 (C-9), 120.6 (C-10), 132.5 (C-10), 115.6(C-20), 146.1 (C-30), 146.3 (C-40), 112.3 (C-50), 118.8 (C-60), 31.3 (C-70),34.2 (C-80), 55.7 (40-OCH3); HR-ESI-MS m/z: 371.1101 [M þ Na]þ

(calcd for C18H20O7Na, 371.1107); Chinese Eaglewood (A. sinensis(Lour.) Gilg), family Thymelaeaceae (Dai et al. 2010).

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https://www.researchgate.net/publication/222738878_A_new_cytotoxic_2-(2-phenylethyl)chromone_from_Chinese_eaglewood?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==



(5S,6R,7R)-5,6,7-Trihydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (55)A white amorphous powder; mp 134–1368C; [a ]D 268 (c ¼ 0.5,MeOH); IR (KBr) gmax cm21: 3414, 2446, 1657, 1570, 1514, 1448,1279, 1107; 1H NMR (CD3OD, 400MHz): dH 6.10 (s, H-3), 4.61 (d,J ¼ 4.0Hz, H-5), 3.70 (dd, J ¼ 4.0, 1.8Hz, H-6), 3.96 (m, H-7), 2.74(overlapped, H-8A), 6.65 (d, J ¼ 1.6Hz, H-20), 6.80 (d, J ¼ 8.2Hz, H-50), 6.59 (dd, J ¼ 8.2, 1.6Hz, H-60), 2.76 (overlapped, H-70), 2.76(overlapped, H-80), 3.80 (s, 40-OCH3);

13C NMR (CD3OD, 100MHz):dC 168.0 (C-2), 112.5 (C-3), 178.6 (C-4), 65.0 (C-5), 69.0 (C-6), 67.4(C-7), 34.0 (C-8), 162.0 (C-9), 120.5 (C-10), 132.4 (C-10), 115.6 (C-20),146.0 (C-30), 146.3 (C-40), 112.2 (C-50), 118.6 (C-60), 31.3 (C-70), 34.1(C-80), 55.6 (40-OCH3); HR-ESI-MS m/z: 371.1103 [M þ Na]þ (calcdfor C18H20O7Na, 371.1107); Chinese Eaglewood (A. sinensis (Lour.)Gilg), family Thymelaeaceae (Dai et al. 2010).

5,6,7,8-Tetrahydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (56)Pale yellow powder; mp 109–1118C; [a ]D þ12.3 (c ¼ 1.0, MeOH); IR(KBr) gmax cm

21: 3409, 1652, 1570, 1514, 1456, 1285, 1110, 1049; 1HNMR (DMSO-d6, 400MHz): dH 6.07 (s, H-3), 4.58 (d, J ¼ 4.2Hz, H-5), 3.74 (dd, J ¼ 6.9, 4.2Hz, H-6), 3.83 (t, J ¼ 6.9Hz, H-7), 4.31 (t,J ¼ 6.9Hz, H-8), 6.67 (d, J ¼ 1.9Hz, H-20), 6.80 (d, J ¼ 8.0Hz, H-50),6.60 (dd, J ¼ 8.0, 1.9Hz, H-60), 2.80 (overlapped, H-70), 2.80(overlapped, H-80), 3.71 (s, 40-OCH3);

13C NMR (DMSO-d6, 100MHz): dC 168.0 (C-2), 112.7 (C-3), 178.5 (C-4), 64.7 (C-5), 72.7 (C-6),70.6 (C-7), 68.4 (C-8), 163.1 (C-9), 120.7 (C-10), 132.6 (C-10), 115.6(C-20), 146.0 (C-30), 146.3 (C-40), 112.2 (C-50), 118.7 (C-60), 31.1 (C-70),34.3 (C-80), 55.6 (40-OCH3); HR-ESI-MS m/z: 387.1053 [M þ Na]þ

(calcd for C18H20O8Na, 387.1056); Chinese Eaglewood (A. sinensis(Lour.) Gilg), family Thymelaeaceae (Dai et al. 2009).

8-Chloro-2-(2-phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydrochromone (57)White amorphous solid; [a ]D þ7.48 (c ¼ 1.0, MeOH); UV (MeOH)lmax (log 1): 253 (4.05) nm; IR gmax cm21: 3352, 2928, 1659, 1601,1435, 1188, 1095, 1041; 1H NMR (C5D5N, 500MHz): dH 6.27 (s, H-3),5.75 (d, J ¼ 3.5Hz, H-5), 4.92 (dd, J ¼ 3.5, 1.6Hz, H-6), 5.17 (dd,J ¼ 7.4, 1.6 Hz, H-7), 5.62 (d, J ¼ 7.4Hz, H-8), 7.20 (m, H-20, 60), 7.28(t, J ¼ 7.2Hz, H-30, 50), 7.19 (m, H-40), 2.86 (m, H-70), 2.71 (m, H-80);13C NMR (C5D5N, 125MHz): dC 168.43 (C-2), 113.71 (C-3), 179.43(C-4), 66.31 (C-5), 74.24 (C-6), 73.70 (C-7), 59.79 (C-8), 159.15 (C-9),124.00 (C-10), 140.41 (C-10), 128.69 (C-20, 60), 128.91 (C-30, 50), 126.72(C-40), 32.75 (C-70), 35.17 (C-80); HR-EI-MS m/z: 337.0833 [M þ H]þ

(calcd for C17H18O535Cl: 337.0832); Withered wood (A. sinensis Gilg),

family Thymelaeaceae (Yagura et al. 2003).

6,7-cis-Dihydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone (58)Brown amorphous solid; [a ]D 215.18 (c ¼ 1.0, MeOH); UV (MeOH)lmax (log 1): 251 (3.87), 203 (4.22) nm; IR gmax cm21: 3360, 2916,1659, 1605, 1443, 1180, 1084, 1038; 1H NMR (C5D5N, 500MHz): dH6.23 (s, H-3), 3.26 (dd, J ¼ 16.8, 6.0Hz, H-5A), 3.03 (dd, J ¼ 16.8,3.4Hz, H-5B), 4.40 (m, H-6), 4.42 (m, H-7), 3.16 (dd, J ¼ 17.2, 6.1Hz,H-8A), 2.95 (dd, J ¼ 17.2, 4.3Hz, H-8B), 7.20 (m, H-20, 60), 7.28 (t,J ¼ 7.2Hz, H-30, 50), 7.20 (m, H-40), 2.83 (t, J ¼ 7.6Hz, H-70), 2.67 (t,J ¼ 7.6Hz, H-80); 13C NMR (C5D5N, 125MHz): dC 167.29 (C-2),112.49 (C-3), 178.96 (C-4), 27.51 (C-5), 68.83 (C-6), 68.55 (C-7), 33.99(C-8), 161.02 (C-9), 119.57 (C-10), 140.67 (C-10), 128.72 (C-20, 60),128.90 (C-30, 50), 126.69 (C-40), 32.99 (C-70), 35.06 (C-80); HR-FAB-MS m/z: 87.1288 [M þ H]þ (calcd for C17H19O4: 287.1283); Witheredwood (A. sinensis Gilg), family Thymelaeaceae (Yagura et al. 2003).

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https://www.researchgate.net/publication/43135749_Two_new_2-(2-phenylethyl)chromone_from_Chinese_eaglewood?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

https://www.researchgate.net/publication/10770169_Four_New_2-(2-Phenylethyl)chromone_Derivatives_from_Withered_Wood_of_Aquilaria_sinensis?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==


AH1; Agarotetrol; (5S,6R,7R,8S)-2-(2-phenylethyl)-5e0,6e0,7e0,8e0-tetrahydroxy-5,6,7,8-tetrahydro-chromone (59)

Colourless needless; mp 179–1818C; [a ]D 221.38 (c ¼ 1.02, MeOH);UV (EtOH) lmax (1): 253 (12000), 208 (15800) nm; IR (KBr) gmax

cm21: 1658, 1600, 1581, 1244, 1182, 1039, 963, 693; 1H NMR (C5D5N,400MHz): dH 6.30 (s, H-3), 5.52 (d, J ¼ 7.0Hz, H-5), 5.19 (dd, J ¼ 7.0,2.0Hz, H-6), 5.05 (dd, J ¼ 4.0, 2.0Hz, H-7), 5.83 (d, J ¼ 4.0Hz, H-8),2.82 (m, H-70), 2.68 (m, H-80), 7.21 (m, H-20-60), 8.14 (brs, 5-OH), 7.30(brs, 6-OH), 7.30 (brs, 7-OH), 7.30 (brs, 8-OH); 13C NMR (C5D5N,100MHz): dC 171.2 (C-2), 114.0 (C-3), 181.8 (C-4), 70.1 (C-5), 72.5(C-6), 73.9 (C-7), 66.8 (C-8), 165.1 (C-9), 121.7 (C-10), 141.1 (C-10),129.5 (C-20, 60), 129.3 (C-30, 50), 127.3 (C-40), 33.7 (C-70), 36.2 (C-80);Agarwood ‘Jinko’ (A. malaccensis LAM.), family Aquilariaceae(Shimada, Konishi, Kiyosawa, Nishi, et al. 1986a).

AH2; Isoagarotetrol (5S,6R,7S,8R)-2-(2-phenylethyl)-5e0,6e0,7e0,8e0-tetrahydroxy-5,6,7,8-tetrahydrochromone(60)

Colourless plates; mp 174–1758C; [a ]D 258.68 (c ¼ 1.19, MeOH);UV (EtOH) lmax (1): 252 (13450), 208 (17300) nm; IR (KBr) gmax

cm21: 1660, 1600, 1582, 1250, 1199, 1042, 968, 697; 1H NMR (C5D5N,400MHz): dH 6.34 (s, H-3), 5.13 (brd, J ¼ 6.5Hz, H-5), 4.46 (dd,J ¼ 10.0, 6.5Hz, H-6), 4.51 (dd, J ¼ 10.0, 6.5 Hz, H-7), 5.42 (dd,J ¼ 6.5, 1.5Hz, H-8), 2.92 (m, H-70), 2.78 (m, H-80), 7.25 (m, H-20-60);8.05 (brs, 5-OH), 6.58 (brs, 6-OH), 4.99 (brs, 7-OH), 7.47 (brs, 8-OH);13C NMR (C5D5N, 100MHz): dC 169.1 (C-2), 113.6 (C-3), 180.9 (C-4),71.9 (C-5), 74.8 (C-6), 75.2 (C-7), 70.9 (C-8), 162.5 (C-9), 121.6 (C-10), 140.4 (C-10), 128.7 (C-20, 60), 128.9 (C-30, 50), 126.9 (C-40), 32.8 (C-70), 35.2 (C-80); Agarwood ‘Jinko’ (A. malaccensis LAM.), familyAquilariaceae (Shimada, Konishi, Kiyosawa, Nishi, et al. 1986a).

Aquilarone A; (5S,6S,7S,8R)-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahy-drochromone (61)

White amorphous powder; [a ]D þ18.0 (c ¼ 1.0, MeOH); UV (MeOH)lmax (log 1): 253 (3.87), 207 (4.22) nm; IR (KBr) gmax cm21: 3359,1656, 1589, 1515, 1446; 1H NMR (DMSO-d6, 50MHz): dH 6.12 (s, H-3), 4.59 (dd, J ¼ 5.5, 5.0Hz, H-5), 3.76 (ddd, J ¼ 6.0, 5.0, 2.0Hz, H-6),3.78 (ddd, J ¼ 5.0, 4.8, 2.0Hz, H-7), 4.36 (dd, J ¼ 6.5, 4.8Hz, H-8),6.66 (d, J ¼ 2.0Hz, H-20), 6.80 (d, J ¼ 8.0Hz, H-50), 6.59 (dd, J ¼ 8.0,2.0Hz, H-60), 2.75 (m, H-70), 2.82 (m, H-80), 3.71 (s, 40-OCH3), 5.05 (d,J ¼ 5.5Hz, 5-OH), 4.90 (d, J ¼ 6.0Hz, 6-OH), 5.35 (d, J ¼ 5.0Hz, 7-OH), 6.07 (d, J ¼ 6.5Hz, 8-OH), 8.82 (brs, 30-OH); 13C NMR (DMSO-d6, 125MHz): dC 168.5 (C-2), 112.8 (C-3), 178.4 (C-4), 64.0 (C-5), 66.6(C-6), 74.5 (C-7), 70.0 (C-8), 162.2 (C-9), 121.4 (C-10), 132.5 (C-10),115.6 (C-20), 146.3 (C-30), 146.1 (C-40), 112.2 (C-50), 118.7 (C-60), 31.2(C-70), 34.3 (C-80), 55.6 (40-OCH3); HR-ESI-MS m/z: 365.1230 (calcdfor C18H21O8 [M þ H]þ 365.1240); Resinous wood of A. sinensis(Lour.) Gilg, family Thymelaeaceae (Chen et al. 2012).

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Aquilarone B, (5S,6S,7S,8R)-2-(2-Phenylethyl)-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (62)Pale yellow amorphous powder; [a ]D þ13.1 (c ¼ 1.0, MeOH); UV(MeOH) lmax (log 1): 252 (4.07), 209 (4.24) nm; IR (KBr) gmax cm

21:3356, 1659, 1602, 1496, 1450; 1H NMR (DMSO-d6, 400MHz): dH 6.13(s, H-3), 4.58 (dd, J ¼ 5.2, 5.0Hz, H-5), 3.76 (ddd, J ¼ 5.6, 5.0, 2.0Hz,H-6), 3.78 (ddd, J ¼ 4.8, 4.0, 2.0Hz, H-7), 4.36 (dd, J ¼ 6.0, 4.0Hz, H-8), 7.16–7.26 (m, H-20-60), 2.75 (m, H-70), 2.82 (m, H-80), 5.04 (d,J ¼ 5.2Hz, 5-OH), 4.90 (d, J ¼ 5.6Hz, 6-OH), 5.35 (d, J ¼ 4.8Hz, 7-OH), 6.00 (d, J ¼ 6.0Hz, 8-OH); 13C NMR (DMSO-d6, 100 MHz): dC168.2 (C-2), 112.8 (C-3), 178.2 (C-4), 64.0 (C-5), 66.6 (C-6), 74.5 (C-7), 70.0 (C-8), 162.2 (C-9), 121.4 (C-10), 139.9 (C-10), 128.2 (C-20),128.3 (C-30), 126.1 (C-40), 128.3 (C-50), 128.2 (C-60), 31.7 (C-70), 34.0(C-80); HR-ESI-MS m/z: 319.1176 (calcd for C17H19O6 [M þ H]þ

319.1174); Resinous wood of A. sinensis (Lour.) Gilg, familyThymelaeaceae (Chen et al. 2012).

Aquilarone C; (5S,6S,7S,8R)-2-[2-(40-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone(63)

Pale yellow amorphous powder; [a ]D þ12.0 (c ¼ 1.0, MeOH); UV(MeOH) lmax (log 1): 252 (4.17), 209 (4.27) nm; IR (KBr) gmax cm

21:3405, 3309, 1662, 1578, 1514, 1451; 1H NMR (DMSO-d6, 400MHz):dH 6.12 (s, H-3), 4.58 (dd, J ¼ 5.5, 5.0Hz, H-5), 3.76 (ddd, J ¼ 6.0, 5.0,2.0Hz, H-6), 3.78 (ddd, J ¼ 5.0, 4.8, 2.0Hz, H-7), 4.36 (dd, J ¼ 6.5,4.8Hz, H-8), 7.15 (d, J ¼ 8.4Hz, H-20, 60), 6.83 (d, J ¼ 8.4Hz, H-30,50), 2.75 (m, H-70), 2.82 (m, H-80), 3.70 (s, 40- OCH3), 5.09 (d,J ¼ 5.5Hz, 5-OH), 5.09 (d, J ¼ 6.0Hz, 6-OH), 5.30 (d, J ¼ 5.0Hz, 7-OH), 5.90 (d, J ¼ 6.5Hz, 8-OH); 13C NMR (DMSO-d6, 100 MHz): dC168.5 (C-2), 112.9 (C-3), 178.4 (C-4), 64.0 (C-5), 66.7 (C-6), 74.6 (C-7), 70.1 (C-8), 162.2 (C-9), 121.4 (C-10), 131.8 (C-10), 129.3 (C-20),113.8 (C-30), 157.7 (C-40), 113.8 (C-50), 129.3 (C-60), 31.0 (C-70), 34.4(C-80), 55.0 (40-OCH3); HR-ESI-MS m/z: 349.1281(calcd for C18H21O7

[M þ H]þ, 349.1291); Resinous wood of A. sinensis (Lour.) Gilg,family Thymelaeaceae (Chen et al. 2012).

Aquilarone D; (5S,6R,7S,8R)-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetra-hydrochromone (64)

White needle-type crystals; mp 190–1918C; [a ]D 258.0 (c ¼ 1.0,MeOH); UV (MeOH) lmax (log 1): 253 (4.04), 213 (4.19) nm; IR (KBr)gmax cm

21: 3340, 1657, 1589, 1515; 1H NMR (DMSO-d6, 500MHz):dH 6.15 (s, H-3), 4.47 (dd, J ¼ 7.0, 3.0Hz, H-5), 3.49 (ddd, J ¼ 7.0, 4.5,4.5Hz, H-6), 3.43 (ddd, J ¼ 7.0, 4.5, 4.5Hz, H-7), 4.32 (dd, J ¼ 7.0,6.5Hz, H-8), 6.66 (d, J ¼ 2.0Hz, H-20), 6.81 (d, J ¼ 8.0Hz, H-50), 6.61(dd, J ¼ 8.0, 2.0Hz, H-60), 2.76 (m, H-70), 2.83 (m, H-80), 3.72 (s, 40-OCH3), 5.14 (d, J ¼ 3.0Hz, 5-OH), 5.34 (d, J ¼ 4.5Hz, 6-OH), 5.21 (d,J ¼ 4.5Hz, 7-OH), 5.83 (d, J ¼ 6.5Hz, 8-OH), 8.84 (brs, 30-OH); 13CNMR (DMSO-d6, 125MHz): dC 168.8 (C-2), 112.7 (C-3), 179.4 (C-4),68.8 (C-5), 73.2 (C-6), 73.5 (C-7), 70.0 (C-8), 161.6 (C-9), 120.1 (C-10), 132.5 (C-10), 115.6 (C-20), 146.3 (C-30), 146.0 (C-40), 112.2 (C-50),118.7 (C-60), 31.1 (C-70), 34.3 (C-80), 55.6 (40-OCH3); HR-ESI-MS m/z:365.1230 (calcd for C18H21O8 [M þ H]þ, 365.1239); Resinous wood ofA. sinensis (Lour.) Gilg, family Thymelaeaceae (Chen et al. 2012).

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Aquilarone E; (5S,6R,7R,8S)-2-[2-(30-hydroxy-40-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (65)

White needle-type crystals; mp 212–2138C; [a ]D 216.0 (c ¼ 1.0,MeOH); UV (MeOH) lmax (log 1): 281 (4.12), 252 (4.23), 212 (4.04)nm; IR (KBr) gmax cm21: 3357, 1656.9, 1590, 1514, 1447; 1H NMR(DMSO-d6, 500 MHz): dH 6.08 (s, H-3), 4.47 (dd, J ¼ 5.0, 4.0Hz, H-5),3.74 (ddd, J ¼ 4.0, 4.0, 2.0Hz, H-6), 3.84 (ddd, J ¼ 7.5, 6.0, 2.0Hz, H-7), 4.32 (dd, J ¼ 7.5, 6.5Hz, H-8), 6.68 (d, J ¼ 2.0Hz, H-20), 6.81 (d,J ¼ 8.5Hz, H-50), 6.61 (dd, J ¼ 8.5, 2.0Hz, H-60), 2.76 (m, H-70), 2.83(m, H-80), 3.72 (s, 40-OCH3), 5.18 (d, J ¼ 5.0Hz, 5-OH), 4.96 (d,J ¼ 4.0Hz, 6-OH), 5.08 (d, J ¼ 6.0Hz, 7-OH), 5.80 (d, J ¼ 6.5Hz, 8-OH), 8.82 (brs, 30-OH); 13C NMR (DMSO-d6, 125MHz): dC 167.9 (C-2), 112.6 (C-3), 178.4 (C-4), 64.7 (C-5), 72.7 (C-6), 70.6 (C-7), 68.4 (C-8), 163.1 (C-9), 120.7 (C-10), 132.6 (C-10), 115.6 (C-20), 146.3 (C-30),146.0 (C-40), 112.2 (C-50), 118.7 (C-60), 31.1 (C-70), 34.3 (C-80), 55.6(40-OCH3); HR-ESI-MS m/z: 365.1230 (calcd for C18H21O8 [M þ H]þ,365.1233); Resinous wood of A. sinensis (Lour.) Gilg, familyThymelaeaceae (Chen et al. 2012).

Aquilarone F; (5S,6R,7R,8S)-2-[2-(40-hydroxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone(66)

Pale yellow amorphous powder; [a ]D 215.0 (c ¼ 1.0, MeOH); UV(MeOH) lmax (log 1): 252 (4.07), 213 (4.23) nm; IR (KBr) gmax cm

21:3381, 1657, 1597, 1515, 1445; 1H NMR (DMSO-d6, 500MHz): dH 6.05(s, H-3), 4.47 (dd, J ¼ 4.5, 4.0Hz, H-5), 5.17 3.74 (ddd, J ¼ 4.0, 4.0,2.0Hz, H-6), 3.84 (ddd, J ¼ 7.5, 6.0, 2.0Hz, H-7), 4.321 (dd, J ¼ 7.5,6.5Hz, H-8), 7.01 (d, J ¼ 8.0Hz, H-20, 60), 6.66 (d, J ¼ 8.0Hz, H-30,50), 2.77 (m, H-70), 2.83 (m, H-80), (d, J ¼ 4.5Hz, 5-OH), 4.96 (d,J ¼ 4.0Hz, 6-OH), 5.10 (d, J ¼ 6.0Hz, 7-OH), 5.81 (d, J ¼ 6.5Hz, 8-OH); 13C NMR (DMSO-d6, 125 MHz): dC 168.0 (C-2), 112.7 (C-3),178.5 (C-4), 64.7 (C-5), 72.7 (C-6), 70.6 (C-7), 68.4 (C-8), 163.1 (C-9),120.7 (C-10), 130.1 (C-10), 129.2 (C-20), 115.1 (C-30), 155.6 (C-40),115.1 (C-50), 129.2 (C-60), 31.2 (C-70), 34.5 (C-80); HR-ESI-MS m/z:335.1124 (calcd for C17H19O7 [M þ H]þ, 335.1125); Resinous wood ofA. sinensis (Lour.) Gilg, family Thymelaeaceae (Chen et al. 2012).

AH16; (5S,6R,7S,8R)-2-(2-Phenylethyl)-5e0,6a,7e,8e0-tetrahydroxy-5,6,7,8-tetrahydrochromone (67)

White powder; mp 100–1058C; [a ]D þ4.76 (MeOH); UV (MeOH)lmax (1) 253 (36321) nm; IR (KBr) gmax cm

21:1658, 1595, 1452, 1409,1094; 1H NMR (C5D5N, 300MHz): dH 6.30 (s, H-3), 5.06 (d,J ¼ 4.1Hz, H-5), 4.96 (dd, J ¼ 4.1, 2.0Hz, H-6), 4.77 (dd, J ¼ 4.9,2.0Hz, H-7), 5.79 (d, J ¼ 4.9Hz, H-8), 2.71 (m, H-70), 2.72 (m, H-80),7.20 (m, H-20-60); Agarwood (A. sinensis), family Thymelaeaceae(Konishi, Iwagoe, Kiyosawa, et al. 1989a, Konishi T, Kiyosawa S,Shimada, et al. 1989b).

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(5S,6R,7S,8R,70R)-70-Hydroxyisoagarotetrol (68)Colourless needless; mp 185–1878C; [a ]D 269.9 (c ¼ 0.84, MeOH);UV (MeOH) lmax (1) 254 (11100), 218 (7800) nm; IR gmax cm

21: 3350(OH), 1657, 1579 (g-pyrone), 1600, 1460, 1420, 750 (benzene ring); 1HNMR (DMSO-d6, 300MHz): dH 6.14 (s, H-3), 4.30 (dd, J ¼ 6.1, 6.0Hz,H-5), 3.43 (ddd, J ¼ 8.6, 6.5, 4.5Hz, H-6), 3.48 (ddd, J ¼ 8.6, 5.9,4.5Hz, H-7), 4.47 (dd, J ¼ 5.9, 3.0Hz, H-8), 4.98 (ddd, J ¼ 8.0, 5.5,5.0Hz, H-70), 2.83 (dd, J ¼ 14.5, 5.5Hz, H-80A), 2.90 (dd, J ¼ 14.5,8.0, Hz, H-80B), 7.25, 7.34, 7.39 (m, H-20-60), 5.83 (d, J ¼ 6.0Hz, 5-OH), 5.34 (d, J ¼ 4.5Hz, 6-OH), 5.23 (d, J ¼ 4.5Hz, 7-OH), 5.15 (d,J ¼ 3.0Hz, 8-OH), 5.60 (d, J ¼ 5.0Hz, 70-OH); 13C NMR (DMSO-d6,75 MHz): dC 167.05 (C-2), 113.87 (C-3), 179.30 (C-4), 69.94 (C-5),73.14 (C-6), 73.45 (C-7), 68.77 (C-8), 161.46 (C-9), 120.08 (C-10),144.44 (C-10), 125.66 (C-20, 60), 128.06 (C-30, 50), 127.10 (C-40), 69.94(C-70), 42.91 (C-80). Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Konishi et al. 1992).

(5S,6R,7S,8R,70S)-70-Hydroxyisoagarotetrol (69)White powder; mp 95–988C; [a ]D 246.1 (c ¼ 1.4, MeOH); UV(MeOH) lmax (1): 254 (13040), 215 (11400) nm; IR gmax cm

21: 3400(OH), 1657, 1590 (g-pyrone), 1600, 1440, 750 (benzene ring); 1H NMR(DMSO-d6, 300MHz): dH 6.20 (s, H-3), 4.32 (d, J ¼ 6.1Hz, H-5), 3.43(dd, J ¼ 8.8, 6.1Hz, H-6), 3.48 (dd, J ¼ 8.8, 6.1Hz, H-7), 4.48 (d,J ¼ 5.7Hz, H-8), 4.98 (dd, J ¼ 8.5, 5.0 Hz, H-70), 2.81 (dd, J ¼ 14.5,8.5Hz, H-80A), 2.89 (dd, J ¼ 14.5, 5.0, Hz, H-80B), 7.26, 7.35, 7.39 (m,H-20-60); 13C NMR (DMSO-d6, 75MHz): dC 166.81 (C-2), 113.93 (C-3), 179.25 (C-4), 69.95 (C-5), 73.13 (C-6), 73.40 (C-7), 68.72 (C-8),161.50 (C-9), 120.09 (C-10), 144.37 (C-10), 125.67 (C-20, 60), 128.04 (C-30, 50), 127.10 (C-40), 69.66 (C-70), 42.94 (C-80); Agalwood (A. sinensis‘Jinko’), family Aquilariaceae (Konishi et al. 1992).

AH2a; 5a,6b,7a,8b-Tetrahydroxy-2-[2-(4-(methoxy-phenyl)ethyl]-5,6,7,8-tetrahydrochromone (70)Colourless needles; mp 198–1998C; [a ]D 267.7 (c ¼ 0.96, MeOH);UV (MeOH) lmax (1): 202 (18909), 223 (18300), 253 (14800) nm; IR(KBr) gmax cm

21: 3500–3200 (OH), 1650, 1610 (g-pyrone ring), 1179,1105, 1035, 1027, 821 (1,4-di-substituted benzene ring); 1H NMR(C5D5N, 400MHz): dH 6.33 (s, H-3), 5.11 (d, J ¼ 6.4Hz, H-5), 4.42(dd, J ¼ 7.0, 6.4Hz, H-6), 4.46 (dd, J ¼ 7.0, 6.7Hz, H-7), 5.35 (d,J ¼ 6.7Hz, H-8), 7.15 (d, J ¼ 8.9Hz, H-20, 60), 6.91 (d, J ¼ 8.9Hz, H-30, 50), 2.84 (m, H-70), 2.84 (m, H-80), 3.64 (40-OCH3);

13C NMR(C5D5N, 100 MHz): dC 169.28 (C-2), 113.55 (C-3), 180.93 (C-4), 71.78(C-5), 74.74 (C-6), 75.07 (C-7), 70.79 (C-8), 162.51 (C-9), 121.42 (C-10), 132.26 (C-10), 129.67 (C-20), 114.44 (C-30), 158.71 (C-40), 114.44(C-50), 129.67 (C-60), 31.90 (C-70), 35.46 (C-80), 55.16 (40-OCH3);Agarwood ‘Jinko’ (A. malaccensis LAM.), family Aquilariaceae(Shimada, Konishi, Kiyosawa, 1986b).

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AH2b; 5a,6b,7a,8b-Tetrahydroxy-2-[2-(2-(hydroxy-phenyl)ethyl]-5,6,7,8-tetrahydrochromone (71)Colourless needles; mp 135–1378C; [a ]D 240.0 (c ¼ 0.85, MeOH);UV (MeOH) lmax (1): 202 (22400), 214.8 (20500), 253 (15300) nm; IR(KBr) gmax cm

21: 3500–3200 (OH), 1660, 1590 (g-pyrone ring), 1190,1126, 1029, 1004, 775 (1,2-disubstituted benzene ring); 1H NMR(C5D5N, 400MHz): dH 6.39 (s, H-3), 5.08 (d, J ¼ 6.4Hz, H-5), 4.41(dd, J ¼ 7.0, 6.4Hz, H-6), 4.46 (dd, J ¼ 7.0, 6.7Hz, H-7), 5.36 (d,J ¼ 6.7Hz, H-8), 7.16 (m, H-30-60), 3.09 (m, H-70), 3.09 (m, H-80); 13CNMR (C5D5N, 100MHz): dC 170.12 (C-2), 113.31 (C-3), 181.11 (C-4),71.75 (C-5), 74.77 (C-6), 75.05 (C-7), 70.86 (C-8), 162.54 (C-9), 121.25(C-10), 127.23 (C-10), 156.66 (C-20), 115.76 (C-30), 128.16 (C-40),119.66 (C-50), 130.50 (C-60), 28.15 (C-70), 33.87 (C-80); Agarwood‘Jinko’ (A. malaccensis LAM.), family Aquilariaceae (Shimada,Konishi, Kiyosawa 1986b).

AH9; (5S,6S,7R)-5a0,6a,7a-Triacetoxy-2-[2-(2-acetoxyphenyl)ethyl]-5,6,7,8,8-pentahydrochrom-one (72)

Colourless needles; mp 147–1488C; [a ]D 211.1 (c ¼ 1.08, MeOH);UV (MeOH) lmax (1): 249 (12973) nm; IR (KBr) gmax cm21: 1754(ester), 1669, 1613 (g-pyrone), 822, 724 (phenyl); 1H NMR (CDCl3,400MHz): dH 6.12 (s, H-3), 6.02 (d, J ¼ 3.5Hz, H-5), 5.33 (dd, J ¼ 6.0,3.5Hz, H-6), 5.21 (br q, J ¼ 10.0, 5.5Hz, H-7), 2.99 (dd, J ¼ 18.0,5.0Hz, H-8A), 2.77 (dd, J ¼ 18.0, 5.0Hz, H-8B), 7.06 (dd, J ¼ 8.0,1.0Hz, H-30), 7.24 (m, H-40-60), 2.78, 2.87 (m, H-70, 80), 2.05, 2.07, 2.08,2.33 (s, 20,5,6,7-CH3CO);

13C NMR (CDCl3, 100MHz): dC 167.94 (C-2), 113.71 (C-3), 176.70 (C-4), 65.99 (C-5), 69.12 (C-6), 66.48 (C-7),27.71 (C-8), 162.26 (C-9), 117.89 (C-10), 132.46 (C-10), 149.74 (C-20),123.17 (C-30), 128.12 (C-40), 126.53 (C-50), 130.19 (C-60), 33.86 (C-70),30.11 (C-80), 20.52, 169.32, 169.98 (20,5,6,7-CH3CO), 20.62 (20,5,6,7-CH3CO); HR-EI-MS m/z 486.1531 [M]þ (calcd for C25H26O10,486.15242); Kalimantan Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Iwagoe et al. 1988).

rel-(5R,6S,7S,8R)-8-Chloro-5,6,7,8-tetrahydro-5,6,7-trihydroxy-2-[2-(4-methoxyphenyl) ethyl]-4H-1-benzopyran-4-one (73)

Pale brown amorphous powder; [a ]D -2.6 (c ¼ 0.138, MeOH); UV(MeOH) lmax (log 1): 253 (4.00), 203 (4.25) nm; IR (KBr) gmax cm

21:3399, 2917, 2849, 1734, 1657, 1610, 1513, 1438, 1247, 1180, 1099,1033; 1H NMR (CDCl3, 500MHz): dH 6.08 (s, H-3), 4.90 (d,J ¼ 7.2Hz, H-5), 4.25 (dd, J ¼ 7.2, 2.1Hz, H-6), 4.36 (dd, J ¼ 3.5,2.1Hz, H-7), 4.71 (d, J ¼ 3.5Hz, H-8), 7.06 (d, J ¼ 8.5Hz, H-20, 60),6.82 (d, J ¼ 8.5Hz, H-30, 50), 2.91 (m, H-70), 2.82 (m, H-80), 3.77 (s, 40-OCH3);

13C NMR (CDCl3, 125MHz): dC 169.7 (C-2), 113.6 (C-3),180.6 (C-4), 68.0 (C-5), 70.4 (C-6), 73.2 (C-7), 53.9 (C-8), 157.3 (C-9),121.2 (C-10), 131.2 (C-1‘), 129.2 (C-20, 60), 114.2 (C-30, 50), 158.4 (C-40), 32.0 (C-70), 35.6 (C-80), 55.3 (40-OCH3); HR-ESI-MS m/z: 367.0931(calcd for C18H20ClO

þ6 [M þ H]þ, 367.0943); Agarwood chips

(A. malaccensis (AM)), family Thymelaeaceae (Wu et al. 2012).

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rel-(5R,6S,7S,8R)-8-Chloro-5,6,7,8-tetrahydro-5,6,7-trihydroxy-2-[2-(3-hydroxy-4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (74)

White amorphous powder; [a ]D 23.9 (c ¼ 0.172, MeOH); UV(MeOH) lmax (log 1): 253 (3.91), 203 (4.37) nm; IR (KBr) gmax

cm21: 3354, 2918, 2849, 1734, 1657, 1590, 1513, 1437, 1276, 1241,1130, 1099, 1024; 1H NMR (CDCl3, 500MHz): dH 6.07 (s, H-3), 4.89(d, J ¼ 7.2Hz, H-5), 4.25 (dd, J ¼ 7.2, 2.2Hz, H-6), 4.36 (dd, J ¼ 3.5,2.2Hz, H-7), 4.71 (d, J ¼ 3.5Hz, H-8), 6.74 (d, J ¼ 2.0Hz, H-20), 6.74(d, J ¼ 8.2Hz, H-50), 6.60 (dd, J ¼ 8.2, 2.0Hz, H-60), 2.88 (m, H-70),2.81 (m, H-80), 3.85 (s, 40-OCH3);

13C NMR (CDCl3, 125MHz): dC172.2 (C-2), 115.1 (C-3), 182.3 (C-4), 67.3 (C-5), 74.4 (C-6), 74.4 (C-7), 58.9 (C-8), 161.9 (C-9), 123.7 (C-10), 134.7 (C-10), 117.2 (C-20),148.5 (C-30), 148.4 (C-40), 113.8 (C-50), 121.4 (C-60), 34.0 (C-70), 37.2(C-80), 57.3 (40-OCH3); HR-ESI-MS m/z: 383.0888 (calcd forC18H20ClO

þ7 ([M þ H]þ, 383.0892); Agarwood chips (A. malaccensis

(AM)), family Thymelaeaceae (Wu et al. 2012).

rel-(5R,6S,7R)-5,6,7,8-Tetrahydro-5,6,7-trihydroxy-2-(2-phenylethyl)-4H-1-benzopyran-4-one (75)rel-(5R,6S,7R)-5,6,7,8-Tetrahydro-5,6,7-trihydroxy-2-[2-(4-methoxyphenyl)ethyl]-4H-1-benzopyran-4-one (76)

Brown amorphous powder (mixture); [a ]D 210.6 (c ¼ 0.221, MeOH);UV (MeOH) lmax: 250, 203 nm; IR (KBr) gmax cm21: 3397, 2918,2848, 1733, 1658, 1601, 1513, 1439, 1246, 1179, 1032; 1H NMR(CDCl3, 500MHz, 75): dH 6.10 (s, H-3), 4.88 (brs, H-5), 4.05 (brs, H-6),4.08 (brs, H-7), 2.77 (m, H-8A), 2.94 (m, H-8B), 7.14 (m, H-20, 60), 7.27(m, H-30, 50), 7.19 (m, H-40), 2.92 (m, H-70), 2.79 (m, H-80); 13C NMR(CDCl3, 125MHz, 75): dC 168.8 (C-2), 113.0 (C-3), 180.5 (C-4), 65.8(C-5), 69.6 (C-6), 67.8 (C-7), 33.5 (C-8), 162.3 (C-9), 119.8 (C-10),139.4 (C-10), 128.2 (C-20, 60), 128.6 (C-30, 50), 126.6 (C-40), 32.9 (C-70),35.1 (C-80); 1H NMR (CDCl3, 500MHz, 76): dH 6.08 (s, H-3), 4.88 (brs,H-5), 4.05 (brs, H-6), 4.08 (brs, H-7), 2.77 (m, H-8A), 2.94 (m, H-8B),7.05 (d, J ¼ 8.5Hz, H-20, 60), 6.81 (d, J ¼ 8.5Hz, H-30, 50), 2.86 (m, H-70), 2.76 (m, H-80), 3.75 (40-OCH3);

13C NMR (CDCl3, 125MHz, 76):dC 168.9 (C-2), 113.0 (C-3), 180.5 (C-4), 65.8 (C-5), 69.6 (C-6), 67.8(C-7), 33.5 (C-8), 162.3 (C-9), 119.6 (C-10), 131.4 (C-10), 129.1 (C-20,60), 114.1 (C-30, 50), 158.3 (C-40), 32.0 (C-70), 35.4 (C-80), 55.2 (40-OCH3);HR-ESI-MS m/z: 303.1220 (calcd for C17H19O

þ5 [M þ H]þ,

303.1227, 75) and 333.1326 (C18H21Oþ6 [M þ H]þ, 333.1333, 76);

Agarwood chips (A. malaccensis (AM)), family Thymelaeaceae(Wu et al. 2012).

AH17; 5a,6b,7b-Trihydroxy-8a-methoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone (77)A white powder; mp 130–1358C; [a ]D þ1.94 (c ¼ 1.03, MeOH); UV(MeOH) lmax (1): 207 (18216), 252 (13678) nm; IR (KBr) gmax cm

21:3360 (OH), 1658, 1600 (g-pyrone ring); 1H NMR (DMSO-d6,300MHz): dH 6.10 (s, H-3), 4.32 (dd, J ¼ 8.1, 6.6 Hz, H-5), 3.74(ddd, J ¼ 8.1, 5.9, 2.1Hz, H-6), 3.93 (ddd, J ¼ 3.8, 3.7, 2.1Hz, H-7),4.14 (d, J ¼ 3.7Hz, H-8), 7.24, 7.26 (H-20-60), 2.87 (m, H-70), 2.96 (m,H-80), 5.83 (d, J ¼ 6.6Hz, 5-OH), 5.18 (d, J ¼ 5.9Hz, 6-OH), 5.09 (d,J ¼ 3.8Hz, 7-OH), 3.36 (s, 8-OCH3);

13C NMR (DMSO-d6, 75MHz):dC 168.20 (C-2), 113.54 (C-3), 179.60 (C-4), 71.37 (C-5), 72.91 (C-6),75.47 (C-7), 70.17 (C-8), 169.29 (C-9), 120.53 (C-10), 144.43 (C-10),128.83 (C-20), 128.56 (C-30), 126.63 (C-40), 128.56 (C-50), 128.83 (C-60), 35.15 (C-70), 32.74 (C-80), 58.94 (8-OCH3); FDMS m/z: 332 (calcdfor C18H20O6); Kalimantan Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Konishi, Iwagoe, Kiyosawa, et al. 1991a, Konishi,Iwagoe, Sugimoto, et al. 1991b).

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2.3. Nuclear magnetic resonance (NMR) spectroscopy

NMR spectroscopy is one the most powerful research techniques used for the structural elucidation

ofPECs.PECsNMRspectra showedkey signals atdH6.00–6.72 (s,H-3)/dC103.0–110.7 (C-3) andtwo coupled triplet or multiplet methylene groups at dH 2.70–2.99 (H-70)/32.0–48.0 (C-70) and2.87–3.16(H-80)/35.0–38.0 (C-80), in addition to signals for aromatic protons characteristic for the

presence of phenylethyl and chromone moieties (Supplementary Figures S1–S8).

3. Biological and pharmacological activities

At present a good number of plant extracts containing PECs derivatives are used as sedative,

analgesic, diuretic, anti-inflammatory, antipyretic, laxative, aphrodisiac, carminative, digestive

and to relieve gastric problems, coughs, rheumatism and high fever (Xiao 2002; Yoon et al.

2006; Liu et al. 2008; Chen et al. 2012; Li et al. 2014; Yang et al. 2014). This encouraged us for

extensive investigations of bioactivity of the PECs derivatives from these plant extracts. The

study of biological and pharmacological activities has revealed that the PECs exhibit a wide

range of bioactivities (Yang et al. 2012). In this review only the pharmacological or biological

activities of pure PECs are highlighted.

3.1. Neuro-protective activity

PEC derivatives (5–12) obtained from Aquilaria sinensis (Thymelaeaceae) exhibited

neuroprotective activities against glutamate-induced neurotoxicity in P12 pheochromocytoma

cells and corticosterone-induced neurotoxicity in human U251 glioma cells (Yang et al. 2012).

5-Hydroxy-2-(2-phenylethyl) chromone (25) isolated from rhizomes of I. cylindrica Beauv.

(Gramineae) showed significant neuroprotective activity against glutamate-induced neurotoxi-

city at 10.0mM concentration using MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazo-

lium bromide) assay (Yoon et al. 2006).

3.2. Cytotoxic activity

5,7-Dihydroxy-2-[2-(3-methoxy-4-hydroxyphenyl)ethyl] chromone (13) isolated from C. melo

L. (Cucurbitaceae) displayed significant cytotoxic activity against L5178Y cells, with an ED50


AH23; 5a,6b,7b,8a-Tetrahydroxy-2-[2-(2-hydroxyphenyl)ethyl]-5,6,7,8-tetrahydrochromone (78)Colourless needles; mp 143–1458C; UV (MeOH) lmax (1): 210(12846), 246 (9654) nm; IR (KBr) gmax cm

21: 3355 (OH), 1645, 1560(g-pyrone ring), 1222, 1095, 1010, 982, 740 (1,2-disubstitutedbenzene); 1H NMR (DMSO-d6, 300MHz): dH 6.09 (s, H-3), 4.31 (d,J ¼ 7.3Hz, H-5), 3.84 (dd, J ¼ 7.3, 2.0Hz, H-6), 3.75 (dd, J ¼ 3.8,2.0Hz, H-7), 4.49 (d, J ¼ 3.8Hz, H-8), 6.80 (dd, J ¼ 7.5, 1.6Hz, H-30),6.71 (d, J ¼ 7.5Hz, H-40), 7.02 (dt, J ¼ 7.5, 1.6Hz, H-50), 7.08 (dd,J ¼ 7.5, 1.6Hz, H-60), 2.81 (m, H-70), 2.88 (m, H-80); 13C NMR(DMSO-d6, 75MHz): dC 168.30 (C-2), 112.34 (C-3), 178.38 (C-4),68.32 (C-5), 70.59 (C-6), 72.59 (C-7), 64.61 (C-8), 163.00 (C-9), 120.64(C-10), 125.96 (C-10), 155.00 (C-20), 114.79 (C-30), 127.23 (C-40),118.81 (C-50), 129.60 (C-60), 26.72 (C-70), 32.24 (C-80); API-MS m/z:335.2 [M þ H]þ (calcd for C18H20O6); Kalimantan Agalwood (A.sinensis ‘Jinko’), family Aquilariaceae (Konishi, Iwagoe, Kiyosawa,et al. 1991a, Konishi, Iwagoe, Sugimoto, et al. 1991b).


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Table 2. Naturally occurring PECs: Group-II (dimer-carbon skeleton).

AH15; (5S,6S,7R,8S)-2-(2-Phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydro-5-[2-(2-phenylethyl)-7-hydroxy-chromonyl-6-oxy]chromone (79)

Colourless needles; mp 244–245 oC; [a ]D þ5.8 (MeOH);UV (MeOH) lmax (1): 244 (36321) nm; IR (KBr) gmax cm

21:1668, 1625, 1590; 1H NMR (DMSO-d6, 300MHz); Unit A:dH 6.16 (s, H-3), 5.34 (d, J ¼ 8.0Hz, H-5), 4.33 (dd, J ¼ 8.0,2.0Hz, H-6), 3.89 (dd, J ¼ 3.6, 2.1Hz, H-7), 4.59 (d,J ¼ 3.7Hz, H-8), 2.51 (m, H-700, 800), C6H5 [6.96 (dd, J ¼ 7.5,2.0Hz) and 7.17 (4H, m)]; Unit B: dH 6.11 (s, H-3), 7.23 (d,J ¼ 2.0Hz, H-50), 6.94 (d, J ¼ 2.0Hz, H-80), 9.95 (s, 7-OH),2.94 (m, H-700, 800), C6H5 [6.96 (dd, J ¼ 7.5, 2.0Hz) and 7.21(4H, m)]; 13C NMR (DMSO-d6, 75MHz); Unit A: dC 167.82(C-2), 113.11 (C-3), 177.81 (C-4), 77.96 (C-5), 68.87 (C-6),73.19 (C-7), 64.17 (C-8), 159.40 (C-9), 124.72 (C-10), 139.59(C-100), 128.19 (C-200, 600), 127.88 (C-300, 500), 126.06 (C-400),31.45 (C-700), 34.16 (C-80); Unit B: dC 167.45 (C-20), 108.60(C-30), 176.35 (C-40), 108.79 (C-50), 149.58 (C-60), 154.40 (C-70), 99.89 (C-80), 154.40 (C-90), 121.81 (C-100), 139.83 (C-100),128.19 (C-200, 600), 127.88 (C-300, 500), 126.06 (C-400), 31.74 (C-700), 34.52 (C-80); Agalwood ‘Jinko’ (A. malaccensis LAM.),family Aquilariaceae (Iwagoe et al. 1987).

AH10; (5S,6S,7R,8S)-2-(2-Phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydro-5-[2-(2-phenylethyl) chromonyl-6-oxy]chromone (80)

White powder; mp 110 oC; [a ]D2127.7 (MeOH); UV (MeOH)lmax (1): 241 (35818) nm; IR (KBr) gmax cm21: 1661, 1639,1610, 1582; 1HNMR (DMSO-d6, 400MHz);UnitA: dH 6.16 (s,H-3), 5.33 (d, J ¼ 8.2Hz, H-5), 4.27 (ddd, J ¼ 8.2, 6.5, 2.0Hz,H-6), 3.89 (ddd, J ¼ 4.2, 3.5, 2.0Hz, H-7), 4.59 (dd, J ¼ 5.5,3.5Hz,H-8), 2.61 (m,H-700), 3.02 (m,H-800), 5.65 (d, J ¼ 6.5Hz,6-OH), 5.35 (d, J ¼ 4.2Hz, 7-OH), 5.51 (d, J ¼ 5.5Hz, 8-OH),C6H5 [6.98 (m), 7.18 (m), and7.27 (m)];UnitB:dH6.22 (s,H-3),7.78 (d, J ¼ 3.0Hz,H-5), 7.62 (dd, J ¼ 8.5, 3.0Hz,H-7), 7.66 (d,J ¼ 8.5Hz,H-8), 2.61 (m,H-700), 3.02 (m,H-800),C6H5 [6.98 (m),7.18 (m), and 7.27 (m)]; 13C NMR (DMSO-d6, 100MHz); UnitA: dC 168.7 (C-2), 113.8 (C-3), 179.7 (C-4), 78.9 (C-5), 71.0 (C-6), 74.7 (C-7), 66.4 (C-8), 160.7 (C-9), 123.7 (C-10), 140.3 (C-100), 128.8 (C-200, 600), 128.5 (C-300, 500), 126.6 (C-400), 32.6 (C-700),35.2 (C-800); Unit B: dC 168.3 (C-20), 110.5 (C-30), 177.5 (C-40),109.6 (C-50), 157.7 (C-60), 124.9 (C-70), 119.7 (C-80), 151.9 (C-90), 124.7 (C-100), 140.5 (C-100), 128.9 (C-200, 600), 128.7 (C-300,500), 126.8 (C-400), 32.9 (C-700), 35.7 (C-800); FDMS m/z: 566,C34H30O8 [M]þ; Agalwood ‘Jinko’ (A. malaccensis LAM.),family Aquilariaceae (Iwagoe et al. 1986).

AH11; 2,20-Di-(2-phenylethyl)-8,60-dihydroxy-5,50-bichromone (81)

Pale yellowish powder; mp 239–242 oC; UV (MeOH) lmax

(1): 234 (42977) nm; IR (KBr) gmax cm21: 1640, 1600, 1580;

13CNMR (DMSO-d6, 20MHz);Unit C: dC 166.5 (C-2), 109.5(C-3), 177.5 (C-4), 129.2 (C-5), 127.1 (C-6), 121.1 (C-7), 144.9(C-8), 151.0 (C-9), 122.1 (C-10), 140.2 (C-100), 128.4 (C-200,600), 128.3 (C-300, 500), 126.2 (C-400), 31.9 (C-700), 34.3 (C-800);Unit D: dC 166.5 (C-20), 109.8 (C-30), 177.5 (C-40), 122.9 (C-50), 150.3 (C-60), 117.6 (C-70), 116.9 (C-80), 144.9 (C-90), 126.2(C-100), 140.2 (C-100), 128.4 (C-200, 600), 128.3 (C-300, 500), 126.2(C-400), 31.9 (C-700), 34.3 (C-800); FDMS m/z: 566, C34H30O8;Agalwood ‘Jinko’ (A. malaccensis LAM.), familyAquilariaceae (Iwagoe et al. 1986).

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AH21; Dioxan linked bi-2-(2-phenylethyl)chromone (82)White powder; mp 123–1258C; [a ]D 275.2 (c ¼ 1.09,MeOH); UV (MeOH) lmax (1): 232 (28229), 247 (25971) nm;IR (KBr) gmax cm21: 3370 (OH), 1660, 1630, 1600 (g-pyrone), 738, 690 (benzene ring); 1H NMR (DMSO-d6,300MHz); Unit A: dH 6.07 (s, H-3), 5.21 (d, J ¼ 7.9Hz, H-5), 4.30 (dd, J ¼ 7.9, 2.0Hz, H-6), 3.88 (ddd, J ¼ 4.0, 3.5,2.0Hz, H-7), 4.57 (d, J ¼ 4.9, 4.0Hz, H-8), 7.00 (dd, J ¼ 8.1,1.7Hz, 2H-phenyl), 7.13, 7.78 (m 4H-phenyl), 2.63 (m, H-7‘,80), 5.33 (d, J ¼ 3.5, Hz, 7-OH), 5.49 (d, J ¼ 4.9, Hz, 8-OH);Unit B: 6.13 (s, H-30), 7.78 (s, H-50), 6.99 (s, H-80), 2.97 (m,H-70, 80); 13C NMR (DMSO-d6, 75MHz); Unit A: dC 167.72(C-2), 113.01 (C-3), 177.89 (C-4), 78.27 (C-5), 68.70 (C-6),73.13 (C-7), 68.14 (C-8), 159.81 (C-9), 121.41 (C-10), 139.97(C-100), 128.21 (C-200, 600), 127.97 (C-300, 500), 31.52 (C-700),34.13 (C-800); Unit B: 167.54 (C-2), 108.01 (C-3), 175.85 (C-4), 109.99 (C-5), 146.84 (C-6), 153.70 (C-7), 103.25 (C-8),152.39 (C-9), 115.40 (C-10), 139.74 (C-100), 128.16 (C-200,600), 127.97 (C-300, 500), 32.01 (C-700), 34.42 (C-800); FD-MS m/z565 [M þ H]þ; Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Konishi, Iwagoe, Kiyosawa, et al. 1991a,Konishi, Iwagoe, Sugimoto, et al. 1991b).

AH12; (5S,6R,7R,8S)-2-(2-Phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)-7-methoxy-chromonyl-6-oxy]chromone (83)

Colourless needles; mp 2278C; [a ]D þ0.7 (c ¼ 14.5, CHCl3:MeOH, 1:1 v/v); UV (MeOH) lmax (1): 209 (51499), 233(42827), 288 (12783), 315 (10563) nm; IR (KBr) gmax cm

-1:3370 (OH), 1658, 1637, 1615, 1600 (g- pyrone); 1H NMR(DMSO-d6, 300MHz); Unit A: dH 6.18 (s, H-3), 4.44 (dd,J ¼ 7.8, 6.6Hz, H-5), 3.88 (ddd, J ¼ 7.8, 5.5, 2.0Hz, H-6),3.98 (ddd, J ¼ 3.5, 3.0, 2.0Hz, H-7), 5.30 (d, J ¼ 3.0Hz, H-8), 6.04 (d, J ¼ 5.5, Hz, 5-OH), 5.28 (d, J ¼ 5.5Hz, 6-OH),5.53 (d, J ¼ 3.5Hz, 7-OH), 2.93 (m, H-700), 2.98 (m, H-800),3.87 (s, 70-OCH3), C6H5 [7.29 (m), and 7.18 (m)]; Unit B: dH6.13 (s, H-30), 7.70 (s, H-50), 7.18 (s, H-80), C6H5 [7.29 (m)and 7.18 (m)], 2.93 (m, H-700), 2.98 (m, H-800);13C NMR(DMSO-d6, 75MHz); Unit A: dC 168.3 (C-2), 112.7 (C-3),177.5 (C-4), 67.8 (C-5), 70.6 (C-6), 68.4 (C-7), 72.2 (C-8),165.0 (C-9), 117.3 (C-10), 140.0 (C-100), 128.3 (C-200, 600),128.2 (C-300, 500), 126.1 (C-400), 31.6 (C-700), 34.0 (C-80); UnitB: dC 167.7 (C-20), 109.0 (C-30), 175.9 (C-40), 107.0 (C-50),145.7 (C-60), 154.7 (C-70), 100.6 (C-80), 152.1 (C-90), 116.1(C-100), 139.9 (C-100), 128.3 (C-200, 600), 128.2 (C-300, 500), 126.1(C-400), 32.0 (C-700), 34.7 (C-80), 56.2 (70-OCH3); KalimantanAgalwood (A. sinensis ‘Jinko’), family Aquilariaceae (Iwagoeet al. 1989).

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AH13; (5S,6R,7R,8S)-2-(2-Phenylethyl)-5,6,7-trihydroxy-5,6,7,8-tetrahydro-8-[2-(2-phenylethyl)chromonyl-6-oxy]chromone (84)

Colourless needles; mp 193–1948C; [a ]D þ2 (c ¼ 5.0,pyridine); UV (MeOH) lmax (1): 227 (47796), 240 (50437),250 (34589), 320 (6981) nm; IR (KBr) gmax cm21: 3410(OH), 1662, 1651, 1622, 1618, 1600 (g-pyrone); 1H NMR(DMSO-d6, 300MHz); Unit C: dH 6.18 (s, H-3), 4.44 (dd,J ¼ 7.9, 6.2Hz, H-5), 3.88 (ddd, J ¼ 7.9, 4.0, 2.0 Hz, H-6),4.02 (ddd, J ¼ 3.5, 3.0, 2.0Hz, H-7), 5.27 (d, J ¼ 3.0Hz, H-8), 6.04 (d, J ¼ 6.2Hz, 5-OH), 5.32 (d, J ¼ 4.0Hz, 6-OH),5.54 (d, J ¼ 3.5 Hz, 7-OH), 2.78 (m, H-700), 2.92 (m, H-800),C6H5 [7.29 (m) and 7.21 (m)]; Unit D: dH 6.21 (s, H-30), 7.63(d, J ¼ 3.2Hz, H-50), 7.43 (dd, J ¼ 9.3, 3.2Hz, H-70), 7.59 (d,J ¼ 9.3Hz, H-80), C6H5 [7.29 (m) and 7.21 (m)], 2.78 (m, H-700), 2.92 (m, H-800); 13C NMR (DMSO-d6, 75MHz); Unit C:dC 168.2 (C-2), 112.6 (C-3), 177.2 (C-4), 67.7 (C-5), 70.6 (C-6), 68.4 (C-7), 72.2 (C-8), 164.7 (C-9), 123.5 (C-10), 139.7(C-100), 128.1 (C-200, 600), 128.1 (C-300, 500), 125.9 (C-400), 31.6(C-700), 34.0 (C-80); Unit D: dC 168.0 (C-20), 108.7 (C-30),176.2 (C-40), 107.5 (C-50), 155.0 (C-60), 124.1 (C-70), 119.5(C-80), 150.6 (C-90), 117.2 (C-100), 139.7 (C-100), 128.1 (C-200,600), 128.1 (C-300, 500), 125.9 (C-400), 32.0 (C-700), 34.6 (C-800);FDMS m/z: 567 [M þ H]þ, 566 [M]þ; Kalimantan Agalwood(A. sinensis ‘Jinko’), family Aquilariaceae (Iwagoe et al.1989).

AH14; (5S,6S,7S,8R)-2-(2-Phenylethyl)-6,7,8-trihydroxy-5,6,7,8-tetrahydro-5-[2-(2-phenylethyl)chromonyl-6-oxy]chromone (85)

White powder; mp 86–888C; [a ]D þ64.4 (c ¼ 1.0, MeOH);UV (MeOH) lmax (1): 207 (37356), 232 (29375), 250(20659), 275 (10471), 310 (8037) nm; IR (KBr) gmax cm

21:3400 (OH), 1655, 1638, 1603, 1578 (g- pyrone); 1H NMR(DMSO-d6, 300 MHz); Unit E: dH 6.21 (s, H-3), 5.50 (dd,J ¼ 7.0, 1.0Hz, H-5), 3.75 (ddd, J ¼ 9.0, 7.0, 5.0Hz, H-6),3.68 (ddd, J ¼ 9.0, 6.5, 4.5Hz, H-7), 4.57 (ddd, J ¼ 6.5, 3.0,1.0Hz, H-8), 5.70 (d, J ¼ 5.0Hz, 6-OH), 5.40 (d, J ¼ 4.5Hz,7-OH), 5.20 (d, J ¼ 3.0Hz, 8-OH), 2.57 (m, H-700), 2.66 (m,H-800), C6H5 [7.98 (2H, m) and 7.18 (4H, m)]; Unit F: dH 6.21(s, H-30), 7.78 (d, J ¼ 2.5Hz, H-50), 7.58 (dd, J ¼ 9.0, 2.5Hz,H-70), 7.65 (d, J ¼ 9.0Hz, H-80), C6H5 [7.18 (m) and 7.21(m)], 3.01 (m, H-700, 800); 13C NMR (C5D5N, 75MHz): UnitE: dC 168.9 (C-2), 113.7 (C-3), 180.5 (C-4), 79.6 (C-5), 73.5(C-6), 74.9 (C-7), 70.6 (C-8), 158.9 (C-9), 122.5 (C-10), 140.2(C-100), 128.9 (C-200, 600), 128.7 (C-300, 500), 126.7 (C-400), 32.5(C-700), 35.4 (C-800); Unit F: dC 168.6 (C-20), 110.4 (C-30),177.5 (C-40), 109.6 (C-50), 157.5 (C-60), 124.7 (C-70), 119.8(C-80), 151.9 (C-90), 124.7 (C-100), 140.4 (C-100), 128.9 (C-200,600), 128.7 (C-300, 500), 126.7 (C-400), 32.9 (C-700), 35.8 (C-800);Kalimantan Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Iwagoe et al. 1989).


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Table 3. Naturally occurring PECs: Group-III (trimer-carbon skeleton).

AH20; Trimer between 22-(2-phenylethyl)chromone and 2 mol of agarotetrol at C5,80 and C6,5

0 (86)Colourless needles; mp 143–1458C; [a ]D 227.83 (c ¼ 0.97,MeOH); UV (MeOH) lmax (1): 212 (50063), 247 (48242) nm; IR(KBr) gmax cm

21: 3320 (OH), 1652, 1595 (g-pyrone ring); 1HNMR (DMSO-d6, 300 MHz); Unit A: dH 6.12 (s, H-3), 5.31 (d,J ¼ 8.3Hz, H-5), 4.36 (dd, J ¼ 8.3, 2.1Hz, H-6), 3.91 (dd,J ¼ 3.2, 2.1Hz, H-7), 4.58 (d, J ¼ 3.2Hz, H-8), 7.02, 7.20, 7.27(H-20-60), 2.62 (m,H-70), 2.86 (m,H-80);UnitB: dH 6.16 (s, H-3),4.87 (d, J ¼ 7.7Hz, H-5), 4.96 (dd, J ¼ 7.7, 1.9Hz, H-6), 3.98(dd, J ¼ 3.7, 1.9Hz, H-7), 4.60 (d, J ¼ 3.7Hz, H-8), 7.02, 7.20,7.27 (H-20-60), 2.68 (m, H-70), 2.94 (m, H-80);Unit C: dH 6.20 (s,H-30), 7.46 (d, J ¼ 9.3Hz,H-60), 7.88 (d, J ¼ 9.3Hz,H-70),), 3.00(m,H-700, 800); 13CNMR(DMSO-d6, 75MHz):UnitA:dC 167.82(C-2), 112.75 (C-3), 177.94 (C-4), 77.87 (C-5), 68.62 (C-6),72.86 (C-7), 64.53 (C-8), 159.58 (C-9), 120.34 (C-10), 139.76 (C-10), 128.31 (C-20), 128.21 (C-30), 126.01 (C-40), 128.21 (C-50),128.31 (C-60), 34.02 (C-70), 31.62 (C-80); Unit B: dC 167.82 (C-2), 112.95 (C-3), 177.96 (C-4), 66.97 (C-5), 82.88 (C-6), 70.33(C-7), 63.39 (C-8), 161.75 (C-9), 121.69 (C-10), 139.88 (C-10),128.31 (C-20), 128.21 (C-30), 126.10 (C-40), 128.21 (C-50), 128.31(C-60), 34.08 (C-70), 31.62 (C-80); Unit C: dC 167.97 (C-20),110.17 (C-30), 178.31 (C-40), 151.77 (C-50), 113.63 (C-60), 123.02(C-70), 144.47 (C-80), 149.51 (C-90), 117.98 (C-100), 139.96 (C-100), 128.31 (C-200), 128.21 (C-300), 126.17 (C-400), 128.21 (C-500),128.31 (C-600), 34.21 (C-700), 31.76 (C-800); FDMS m/z: 883[M þ H]þ; Kalimantan Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Konishi, Iwagoe, Kiyosawa, et al. 1991a;Konishi, Iwagoe, Sugimoto, et al. 1991b).

AH19a (87)White powder;mp 165–1678C; [a ]D233.89 (c ¼ 1.18,MeOH);UV (MeOH) lmax (log 1): 242 (4.56), 250 (4.57) nm; IR (KBr)gmax cm

21: 3380 (OH), 1655, 1648, 1638, 1603 (g-pyrone ring),690 (benzene ring); 1H NMR (DMSO-d6, 300MHz); Unit A: dH5.330 (d, J ¼ 7.5Hz,H-5), 4.291 (dd, J ¼ 7.5, 2.0Hz,H-6), 3.862(dd, J ¼ 4.0, 2.0Hz, H-7), 4.564 (d, J ¼ 4.0Hz, H-8), 6.911 (dd,J ¼ 7.0, 2.0Hz, 2H-phenyl), 6.953 (dd, J ¼ 7.1, 2.2Hz, 2H-phenyl), 7.121 (m, 7H-phenyl), 7.186 (m, 4H-phenyl), 2.535 (m,H-70), 2.894 (m, H-80); Unit B: dH 5.729 (d, J ¼ 7.8Hz, H-5),3.841 (dd, J ¼ 9.6, 7.8Hz,H-6), 3.637 (dd, J ¼ 9.6, 6.9Hz,H-7),4.480 (d, J ¼ 6.9Hz, H-8), 6.911 (dd, J ¼ 7.0, 2.0Hz, 2H-phenyl), 6.953 (dd, J ¼ 7.1, 2.2Hz, 2H-phenyl), 7.121 (m, 7H-phenyl), 7.186 (m, 4H-phenyl), 2.535 (m, H-70), 2.894 (m, H-80);Unit C: dH 7.856 (s, H-5), 7.806 (s, H-8); 13C NMR (DMSO-d6,75MHz); Unit A: dC 167.923 (C-2), 113.010 (C-3), 177.815 (C-4), 77.514 (C-5), 69.174 (C-6), 73.039 (C-7), 64.250 (C-8),157.782 (C-9), 121.485 (C-10), 139.428 (C-10), 127.823–128.280(C-20, 30, 50, 60), 126.106 (C-40), 31.185 (C-70), 33.966 (C-80);UnitB: dC 167.965 (C-2), 113.228 (C-3), 178.871 (C-4), 77.644 (C-5),71.817 (C-6), 73.305 (C-7), 68.602 (C-8), 159.456 (C-9), 122.006(C-10), 139.477 (C-10), 127.823–128.280 (C-20, 30, 50, 60),126.106 (C-40), 31.356 (C-70), 34.107 (C-80);Unit C: dC 167.340(C-2), 109.252 (C-3), 175.797 (C-4), 108.852 (C-5), 147.389 (C-6), 154.355 (C-7), 103.832 (C-8), 151.867 (C-9), 116.792 (C-10),139.854 (C-10), 127.823–128.280 (C-20, 30, 50, 60), 126.004 (C-40),31.920 (C-70), 34.757 (C-80); FDMS m/z: 883 [M þ H]þ;Kalimantan Agalwood (A. sinensis ‘Jinko’), familyAquilariaceae (Konishi, Iwagoe, Kiyosawa, et al. 1989a;Konishi, Kiyosawa, Shimada, et al. 1989b).

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of 5mM using MTT assay (Ibrahim 2014). 8-Chloro-5,6,7-trihydroxy-2-(3-hydroxy-4-

methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (53) isolated from A. sinensis

(Thymelaeaceae) showed cytotoxicity against human gastric cancer cell line (SGC-7901)

in vitro by the MTT method with IC50 value of 14.6mg/mL (Liu et al. 2008). 5,6,7,8-

Tetrahydroxy-2-(3-hydroxy-4-methoxyphenethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one (56)exhibited no cytotoxic activity against K562, SGC-7901, human liver cancer cell line

(SMMC-7721) (Dai et al. 2009). Compounds 31, 33 and 34 were also evaluated for their

cytotoxic activity against human myeloid leucaemia (K562), human hepatocellular carcinoma

(BEL-7402) and human gastric (SGC-7901) cancer cell lines by the MTT method. However, the

results showed that compounds 31, 33 and 34 were inactive against the three human cancer cell

lines (conc. 100mg/mL) (Yang et al. 2014).

3.3. AChE inhibitory activity

Acetylcholinesterase (AChE) inhibitory activity of these compounds was assayed by the

spectrophotometric method using S-acetylthiocholine iodide and 5,50 -dithio-bis-(2-nitroben-zoic) acid. The PECs, 2-[2-hydroxy-2-(4-hydroxyphenyl) ethyl] chromone (33) and 2-[2-

hydroxy-2-(4-methoxyphenyl) ethyl] chromone (34), isolated from A. sinensis showed weak

inhibitory activity with the inhibition percentage of 20.3 and 25.4%, respectively, at the

concentration of 50mg/mL (Yang et al. 2014). Compounds 38, 39 and 49 isolated from


AH19b (88)White powder; mp 130–1338C; [a ]D 264.04 (c ¼ 0.87,MeOH); UV (MeOH) lmax (log 1): 240 (4.59), 250 (4.70) nm;IR (KBr) gmax cm

21: 3360 (OH), 1655, 1642, 1633, 1600 (g-pyrone ring), 690 (benzene ring); 1H NMR (DMSO-d6,300MHz); Unit D: dH 5.537 (d, J ¼ 7.5Hz, H-5), 3.824 (dd,J ¼ 9.0, 7.5Hz, H-6), 3.663 (dd, J ¼ 9.0, 6.6Hz, H-7), 4.449(d, J ¼ 6.6Hz, H-8), 6.900 (dd, J ¼ 8.0, 2.0Hz, 2H-phenyl),6.940 (dd, J ¼ 8.0, 2.0Hz, 2H-phenyl), 7.123 (m, 7H-phenyl),7.229 (m, 2H-phenyl), 2.555 (m, H-70), 2.930 (m, H-80); UnitE: dH 5.515 (d, J ¼ 7.5Hz, H-5), 4.345 (dd, J ¼ 7.5, 2.0Hz, H-6), 3.896 (dd, J ¼ 4.0, 2.0Hz, H-7), 4.592 (d, J ¼ 4.0 Hz, H-8),6.900 (dd, J ¼ 8.0, 2.0Hz, 2H-phenyl), 6.940 (dd, J ¼ 8.0,2.0Hz, 2H-phenyl), 7.123 (m, 7H-phenyl), 7.229 (m, 2H-phenyl), 2.555 (m, H-70), 2.930 (m, H-80); Unit F: dH 7.884 (s,H-5), 7.726 (s, H-8); 13C NMR (DMSO-d6, 75MHz); Unit D:dC 167.882 (C-2), 112.958 (C-3), 177.936 (C-4), 77.863 (C-5),69.008 (C-6), 73.197 (C-7), 68.376 (C-8), 159.040 (C-9),122.043 (C-10), 139.531 (C-10), 127.770–128.268 (C-20, 30, 50,60), 126.087 (C-40), 31.307 (C-70), 33.954 (C-80); Unit E: dC167.986 (C-2), 113.312 (C-3), 178.849 (C-4), 77.323 (C-5),69.008 (C-6), 73.197 (C-7), 64.143 (C-8), 158.345 (C-9),121.467 (C-10), 139.480 (C-10), 127.770–128.268 (C-20, 30, 50,60), 126.087 (C-40), 31.307 (C-70), 34.754 (C-80); Unit F: dC167.348 (C-2), 108.849 (C-3), 175.793 (C-4), 109.264 (C-5),147.283 (C-6), 154.480 (C-7), 104.055 (C-8), 151.818 (C-9),116.890 (C-10), 139.955 (C-10), 127.770–128.268 (C-20, 30, 50,60), 126.010 (C-40), 31.890 (C-70), 34.754 (C-80); FDMS m/z:883 [M þ H]þ; Kalimantan Agalwood (A. sinensis ‘Jinko’),family Aquilariaceae (Konishi, Iwagoe, Kiyosawa, et al.1989a; Konishi, Kiyosawa, Shimada, et al. 1989b).


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https://www.researchgate.net/publication/40768355_A_New_2-(2-Phenylethyl)Chromone_from_Chinese_Eaglewood?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

https://www.researchgate.net/publication/261289004_New_chromone_and_triglyceride_from_Cucumis_melo_seeds?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

https://www.researchgate.net/publication/222738878_A_new_cytotoxic_2-(2-phenylethyl)chromone_from_Chinese_eaglewood?el=1_x_8&enrichId=rgreq-728cdd42-c91a-4b41-a00f-eacebc05979c&enrichSource=Y292ZXJQYWdlOzI2OTkzNDc1ODtBUzoxOTY4MTMwMzU0NDYyNzJAMTQyMzkzNTI5MjgxNg==

A. sinensis showed moderate AChE inhibitory activity with the inhibition percentage as 32.4%,

33.6% and 31.5%, respectively (conc. 50mg/mL) (Li et al. 2014).

3.4. Antibacterial activity

6-Methoxy-2-[2-(3-hydroxy-4-methoxyphenyl) ethyl] chromone (38), a PEC isolated from A.

sinensis, was evaluated for in vitro antibacterial activity against Staphylococcus aureus and

Ralstonia solanacearum using the filter paper disc agar diffusion method. It showed moderate

activity against S. aureus (conc. 10mg/mL) (Li et al. 2014).

3.5. Anti-inflammatory

Compounds 35–37 and 61–66 isolated from A. sinensis (Thymelaeaceae) exhibited potent

inhibitory activity against lipopolysaccharide-inducedNOproduction inRAW264.7macrophages,

with IC50 values in the range of 5.12–22.26mM compared with ibuprofen (IC50 94.12mM).

However, these compounds did not exhibit obvious inhibition against COX-2 (Chen et al. 2012).

Supplementary material

Supplementary material relating to this article is available online, alongside Figures S1–S8.

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Natural occurring 2-(2-phenylethyl) chromones, structure elucidation and biological activities

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