Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Anti-inflammatory and PPAR Transactivational Effects of Components from Ginkgo biloba Seeds

  • Received : 2014.03.31
  • Accepted : 2014.05.13
  • Published : 2014.09.20
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Abstract

Keywords

Experimental

Plant Materials. The seeds of G. biloba were purchased from herbal market at Kumsan, Chungnam, Korea, in August, 2010. The plant material was identified by one of us (Y. H. Kim). A voucher specimen (CNU10110) was deposited at herbarium, College of Pharmacy, Chungnam National University.

Extraction and Isolation. The dried seeds (10.5 kg) were extracted three times with hot MeOH under reflux. After concentration, the MeOH extract (200 g) was suspended in H2O and then partitioned successively with n-hexane, CH2Cl2, and EtOAc to give n-hexane (sA, 110 g), CH2Cl2 (sB, 1.1 g), EtOAc (sC, 1.3 g) and aqueous (sD, 80 g) fractions, respectively. The aqueous fraction sD was chromatographed on a column of highly porous polymer (Diaion HP-20) and eluted with a step-wise gradient of 0, 30, 60 and 100% (v/v) MeOH in H2O to give four fractions (sD1-sD4). Fraction sD2 (27 g) was separated by YMC RP column chromatography (CC), using MeOH-H2O (1:2) as eluents to give six subfractions (sD2.1-sD2.6). Compound 9 (7 mg) was isolated by silica gel CC, eluting with CH2Cl2-MeOH (9:1) from subfraction sD2.1 (200 mg). Subfraction sD2.2 was separated by CC over silica gel, eluting with CH2Cl2-MeOH (10:1), and further purified by silica gel CC, using CH2Cl2-acetone (2:1) as eluents, to obtain compounds 4 (9 mg) and 2 (6 mg). Compound 13 (11 mg) was isolated by preparative TLC using CH2Cl2-MeOH-H2O (4:1:0.1) from subfraction sD2.4 (50 mg). Subfraction sD2.3 (200 mg) was separated by silica gel CC, eluting with CH2Cl2-MeOH-H2O (5:1:0.1) to give two subfractions sD2.31-sD2.32. Compounds 6 (10 mg) and 7 (5 mg) were isolated by preparative TLC using CH2Cl2-MeOH-H2O (3:1:0.1) from subfractions sD2.31 (35 mg) and sD2.32 (42 mg), respectively. Compound 10 (8 mg) was isolated by CC over silica gel, eluting with CH2Cl2-MeOH (10:1) from subfraction sD2.6 (65 mg). Subfraction sD2.5 (0.3 g) was separated by silica gel CC, eluting with CH2Cl2-MeOH-H2O (6:1:0.1) to give two subfractions sD2.51-sD2.52. Compounds 1 (3 mg) and 3 (9 mg) were isolated by preparative TLC using CH2Cl2-MeOH-H2O (4:1:0.1) from subfractions sD2.51 (80 mg) and sD2.52 (66 mg), respectively. Fraction sD3 (8 g) was separated by silica gel CC, eluting with CH2Cl2-MeOH (10:1) to provide four subfractions (sD3.1-sD3.4). Compounds 8 (13 mg) and 5 (11 mg) were isolated by precipitation and filtered with MeOH from subfractions sD3.1 (100 mg) and sD3.2 (97 mg), respectively. Compounds 11 (14 mg) and 12 (10 mg) were isolated by preparative TLC using CH2Cl2-MeOH-H2O (4:1:0.1) from subfractions sD3.3 (170 mg) and sD3.4 (106 mg), respectively.

(2E,4E)-Dihydrophaseic Acid (1): Colorless, viscous liquid; +16.7 (c 0.1, MeOH). HRESIQTOFMS: m/z 281.1387 [M-H]− (calcd for C15H21O5, 281.1389), m/z 317.1157 [M+Cl]− (calcd for C15H22O5Cl, 317.1156). 1H NMR (600 MHz, CD3OD) δ 7.69 (d, J = 15.6 Hz, H-4), 6.22 (d, J = 15.6 Hz, H-5), 5.81 (s, H-2), 4.06 (m, H-3'), 3.77 (dd, J = 6.6, 1.8 Hz, H-7'α), 3.66 (d, J = 6.6 Hz, H-7'β), 1.98 (m, H-4'α), 1.93 (s, H3-6), 1.80 (m, H-2'α), 1.72 (dd, J = 13.8, 10.2 Hz, H-4'β), 1.64 (m, H-2'β), 1.11 (s, H3-9'), 0.89 (s, H3-10'); 13C NMR (150 MHz, CD3OD) δ 174.6 (C-1), 139.8 (C-3), 132.1 (C-4), 129.2 (C-5), 127.2 (C-2), 86.8 (C-5'), 82.2 (C-8'), 76.3 (C-7'), 65.1 (C-3'), 48.8 (C-1'), 45.0 (C-4'), 43.5 (C-2'), 19.5 (C-6), 18.7 (C-9'), 15.4 (C-10').

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