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Flavonoids from Guizotia Abyssinica

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Flavonoids from Guizotia Abyssinica J Chin Med 18(3,4): 121-128, 2007 121 FLAVONOIDS FROM GUIZOTIA ABYSSINICA Wen-Lung Kuo1, Chien-Chih Chen2, Po-Hao Chang1, Lee-Ying Cheng3, Bor-Jinn Shien1*, Yu-Ling Huang2* 1Department of Chemistry, Chung Yuan University, Taoyuan, Taiwan 2National Research Institute of Chinese Medicine, Taipei, Taiwan 3Seed Improvement and Propagation Station, Taichung, Taiwan ( Received 17th May 2007, accepted 6h June 2007 ) Nine flavonoids, (–)-liquiritigenin (1), (–)-7,3',4'-trihydroxyflavanone (2), (–)-7,8,3',4'-tetrahydr oxyflavanone (3), 7,3',4'-trihydroxylflavone (4), quercetin (5), isoliquiritigenin (6), butein (7), okanin (8), and 3,2',4'-trihydroxy-4,3'-dimethoxychalcone (9), were isolated from the aerial parts of Guizotia abyssinica. The structures of these compounds were identified on the basis of their spectral data and comparison with those in the literature. Key words: Guizotia abyssinica, Asteraceae, aerial part, flavonoid. 4,9 10 11 INTRODUCTION isoliquiritigenin (6), butein (7), okanin (8), and 3,2',4'-trihydroxy-4,3'-dimethoxychalcone (9),4,10,11 Guizotia abyssinica (L.f.) Cass. belongs to the were isolated from the water soluble portion of its family of Asteraceae and grows in the countries like MeOH extract. The structures of these compounds India and Ethiopiais. Guizotia abyssinica is primarily were identified on the basis of their spectral analyses cultivated in India and its seeds have high content of and comparison with spectroscopic and physical data linoleic acid. The oil of the seeds of G. abyssinica in literature. is traditionally used for treatment of rheumatism.1,2 The phytochemical study of this plant has not been MATERIALS AND reported. In our investigation on the chemical METHODS constituents of G. abyssinica, nine compounds, (–)-liquiritigenin (1),3,4 (–)-7,3',4'-trihydroxyfla General Methods vanone (2),5 (–)-7,8,3',4'-tetrahydroxylflavanone Optical rotations were recorded on a Jasco (3),6 7,3',4'-trihydroxyflavone (4),7 quercetin (5),4,8 DIP-370 polarimeter. IR spectra were measured on a *Corresponding authors: Bor-Jinn Shien, Phone: 886-3-2653328, Fax: 886-3-2653399, E-mail: [email protected]; Yu- Ling Huang, Phone: 886-2-28201999 ext. 6241, Fax: 886-2-28264276, E-mail: [email protected] 122 FLAVONOIDS FROM GUIZOTIA ABYSSINICA Nicolet Avatar 320 FT-IR spectrophotometer. EIMS collected at the Seed Improvement and Propagation and HREIMS spectra were recorded on a Finnigan Station, Hsinshe, Taichung, Taiwan. The voucher MAT GCQ and a Finnigan/Thermo Quest MAT 95XL specimen was deposited at the Herbarium of the Mass spectrometers, respectively. The NMR spectra National Research Institute of Chinese Medicine, were recorded on a Bruker AC-400 spectrometers. R.O.C. Melting point was determinted on a Yanaco MP-I3 micro melting point apparatus. For thin-layer Extraction and Isolation chromatography analysis, silica gel 60 F254 plates The air-dried aerial parts of Guizotia abyssinica (Merck) were used. (22 Kg) were extracted at 50°C with MeOH (120 L× 3). After evaporation of the solvent, the concentrated Plant Material MeOH extract was separated into water-soluble The aerial parts of Guizotia abyssinica were and water-insoluble portions. The water-soluble Wen-Lung Kuo, Chien-Chih Chen, Po-Hao Chang, Lee-Ying Cheng, Bor-Jinn Shien, Yu-Ling Huang 123 portion was subjected to a Diaion HP-20 column (–)-Liquiritigenin (1) 25 and eluted with H2O and then MeOH to afford H2O Brown solid; mp 180-182°C; [α]D –18.9° (c -1 and MeOH fractions. The MeOH fraction (200 0.9, MeOH); IR vmax (KBr) cm : 3474, 1661, 1603, g) was rechromatographed on a silica gel column 1571, 1514, 1472, 1335, 1267, 1162; 1H NMR (400 eluting with n-hexane/EtOAc and EtOAc/MeOH MHz, acetone-d6) δ: 2.62 (1H, dd, J = 2.8, 16.8 Hz, mixtures as solvent systems to give 24 fractions (Fr- H-3), 3.00 (1H, dd, J = 12.8, 16.8 Hz, H-3), 5.40 1~Fr-24). The fraction Fr-5, eluate of n-hexane- (1H, dd, J = 2.8, 12.8 Hz, H-2), 6.38 (1H, d, J = 2.4 EtOAc (5:1), was further chromatographed on a silica Hz, H-8), 6.54 (1H, dd, J = 2.4, 8.8 Hz, H-6), 6.87 gel column eluting with n-hexane-EtOAc (1:1) and (2H, d, J = 8.8 Hz, H-3', 5' ), 7.36 (2H, d, J = 8.8 Hz, Sephadex LH-20 (MeOH) to give (–)-liquiritigenin H-2', H-6' ), 7.68 (1H, d, J = 8.8 Hz, H-5); 13C NMR (1, 13.1 mg), isoliquiritigenin (6, 29.8 mg), and (100 MHz, acetone-d6) δ: 43.8 (C-3), 79.5 (C-2), 3,2',4'-trihydroxy-4,3'-dimethoxychalcone (9, 4.6 102.8 (C-8), 110.9 (C-6), 113.5 (C-10), 115.2 (C-3' mg). The fraction Fr-8, eluate of n-hexane-EtOAc and C-5' ), 128.0 (C-2' and C-6' ), 128.5 (C-5), 130.4 (1:1), was reseparated on a silica gel column eluting (C-1' ), 157.7 (C-4' ), 163.8 (C-9), 165.9 (C-7), 189.6 + with a gradient solvent system of CHCl3/Me2CO (5:1 (C-4); EIMS m/z (rel. int.): 256 [M] (C15H12O4, 100), →1:1) to afford five fractions (Fr-8-1~Fr-8-5). The 239 (12), 163 (11), 150 (12), 137 (37), 120 (15). fraction Fr-8-4, eluate of CHCl3/Me2CO (2:1), was further purified by silica gel (CHCl3/Me2CO = 3:1) (–)-7,3',4'-Trihydroxyflavanone (2) 25 and Sephadex LH-20 (MeOH) columns to give (–)-7 Yellow syrup; [α]D –38.8° (c 0.8, MeOH); IR -1 ,3',4'-trihydroxyflavanone (2, 29.8 mg) and butein (7, νmax (KBr) cm : 3274, 1650, 1608, 1461, 1324, 1277, 1 10.8 mg). Fraction Fr-8-5, eluate of CHCl3/Me2CO 1156, 1114, 809; H NMR (400 MHz, acetone-d6) δ: (1:1), was purified over silica gel (CHCl3/Me2CO = 2.68 (1H, dd, J = 2.8, 16.8 Hz, H-3), 3.00 (1H, dd, 3:1) and Sephadex LH-20 (MeOH) columns to afford J = 12.8, 16.8 Hz, H-3), 5.31 (1H, dd, J = 2.8, 12.8 quercetin (5, 12.9 mg) and (–)-7,8,3',4'-tetrahydrox Hz, H-2), 6.35 (1H, d, J = 2.4 Hz, H-8), 6.49 (1H, dd, yflavanone (3, 23.5 mg). The fraction Fr-10, eluate J = 2.4, 8.8 Hz, H-6), 6.73 (1H, d, J = 8.0 Hz, H-5' ), of n-hexane-EtOAc (1:2), was rechromatographed 6.72 (1H, dd, J= 2.0, 8.0 Hz, H-6' ), 6.92 (1H, d, on a silica gel column eluting with a gradient solvent J = 2.0 Hz, H-2' ), 7.72 (1H, d, J = 8.8 Hz, H-5); 13C system of CHCl3/Me2CO (5:1→1:1) to afford four NMR (100 MHz, acetone-d6) δ: 44.1 (C-3), 79.9 (C-2), fractions (Fr-10-1~Fr-10-4). The fraction Fr-10-2, 103.1 (C-8), 110.5 (C-6), 114.0 (C-2' ), 114.6 (C-10), eluate of CHCl3/Me2CO (3:1), was further purified 115.3 (C-5' ), 118.5 (C-6' ), 128.8 (C-5), 131.4 (C-1' ), over silica gel (CHCl3/Me2CO＝3:1) and Sephadex 145.3 (C-4' ), 145.6 (C-3' ), 163.8 (C-9), 164.6 (C-7), + LH-20 (MeOH) columns to obtain 7,3',4'-trihydroxy 189.9 (C-4); EIMS m/z (rel. int.): 272 [M] (C15H12O5, flavone (4, 2.7 mg). The fraction Fr-10-3, eluate of 100), 255 (18), 163 (17), 150 (48), 137 (40). CHCl3/Me2CO (2:1), was purified through a silica gel (CHCl3/Me2CO = 2:1) and Sephadex LH-20 (MeOH) (–)-7,8,3',4'-Tetrahydroxyflavanone (3) 25 columns to afford okanin (8, 506.0 mg). Yellow syrup, [α]D –110.0° (c 0.3, MeOH); IR 124 FLAVONOIDS FROM GUIZOTIA ABYSSINICA -1 νmax (KBr) cm : 3358, 1656, 1608, 1524, 1456, 1319, 8.8 Hz, H-6' ), 7.81 (1H, d, J = 2.0 Hz, H-2' ), 12.1 1 13 1282; H NMR (400 MHz, acetone-d6) δ: 2.64 (1H, (1H, s, 5-OH); C NMR (100 MHz, acetone-d6) δ: dd, J = 2.8, 16.8 Hz, H-3), 3.01 (1H, dd, J = 12.8, 94.5 (C-8), 99.2 (C-6), 104.1 (C-10), 115.8 (C-2' ), 16.8 Hz, H-3), 5.37 (1H, dd, J = 2.8, 12.8 Hz, H-2), 116.2 (C-5' ), 121.5 (C-6' ), 123.8 (C-1' ), 136.8 (C-3), 6.58 (1H, d, J = 8.8 Hz, H-6), 6.86 (1H, d, J = 8.0 Hz, 145.9 (C-3' ), 147.0 (C-2), 148.1 (C-4' ), 157.8 (C-9), H-5' ), 6.85 (1H, dd, J = 1.6, 8.0 Hz, H-6' ), 7.03 (1H, 162.3 (C-5), 165.1 (C-7), 176.6 (C-4); EIMS m/z (rel. + d, J = 1.6 Hz, H-2' ), 7.28 (1H, d, J = 8.8 Hz, H-5); int.): 302 [M] (C15H10O7, 100), 284 (55), 274 (12), 13 C NMR (100 MHz, acetone-d6) δ: 44.1 (C-3), 80.3 229 (9). (C-2), 109.6 (C-6), 114.0 (C-2' ), 114.8 (C-10), 115.0 (C-5'), 117.9 (C-5), 118.4 (C-6' ), 131.0 (C-1' ), 132.7 Isoliquiritigenin (6) (C-8), 145.1 (C-3' ), 145.5 (C-4' ), 150.8 (C-9), 151.7 Orange solid; mp 189-191°C; IR νmax (KBr) (C-7), 190.2 (C-4); EIMS m/z (rel.
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