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Anti-inflammatory and PPAR Transactivational Effects of Components from Ginkgo biloba Seeds
Anti-inflammatory and PPAR Transactivational Effects of Components from Ginkgo biloba Seeds
Bulletin of the Korean Chemical Society. 2014. Sep, 35(9): 2843-2846
Copyright © 2014, Korea Chemical Society
  • Received : March 31, 2014
  • Accepted : May 13, 2014
  • Published : September 20, 2014
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About the Authors
Nguyen Thi Thanh Ngan
Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
Tran Hong Quang
Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam
Seok Bean Song
College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea.
Young Ho Kim
College of Pharmacy, Chungnam National University, Daejeon 305-764, Korea.

Abstract
Keywords
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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 H 2 O and then partitioned successively with n -hexane, CH 2 Cl 2 , and EtOAc to give n -hexane (sA, 110 g), CH 2 Cl 2 (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 H 2 O to give four fractions (sD1-sD4). Fraction sD2 (27 g) was separated by YMC RP column chromatography (CC), using MeOH-H 2 O (1:2) as eluents to give six subfractions (sD2.1-sD2.6). Compound 9 (7 mg) was isolated by silica gel CC, eluting with CH 2 Cl 2 -MeOH (9:1) from subfraction sD2.1 (200 mg). Subfraction sD2.2 was separated by CC over silica gel, eluting with CH 2 Cl 2 -MeOH (10:1), and further purified by silica gel CC, using CH 2 Cl 2 -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 CH 2 Cl 2 -MeOH-H 2 O (4:1:0.1) from subfraction sD2.4 (50 mg). Subfraction sD2.3 (200 mg) was separated by silica gel CC, eluting with CH 2 Cl 2 -MeOH-H 2 O (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 CH 2 Cl 2 -MeOH-H 2 O (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 CH 2 Cl 2 -MeOH (10:1) from subfraction sD2.6 (65 mg). Subfraction sD2.5 (0.3 g) was separated by silica gel CC, eluting with CH 2 Cl 2 -MeOH-H 2 O (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 CH 2 Cl 2 -MeOH-H 2 O (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 CH 2 Cl 2 -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 CH 2 Cl 2 -MeOH-H 2 O (4:1:0.1) from subfractions sD3.3 (170 mg) and sD3.4 (106 mg), respectively.
(2E,4E)-Dihydrophaseic Acid (1) : Colorless, viscous liquid;
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+16.7 ( c 0.1, MeOH). HRESIQTOFMS: m/z 281.1387 [M-H] (calcd for C 15 H 21 O 5 , 281.1389), m/z 317.1157 [M+Cl] (calcd for C 15 H 22 O 5 Cl, 317.1156). 1 H NMR (600 MHz, CD 3 OD) 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, H 3 -9'), 0.89 (s, H 3 -10'); 13 C NMR (150 MHz, CD 3 OD) 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').
Supporting Information. The HRESIQTOFMS and NMR spectra of compound 1, physicochemical properties of compounds 2-13, and experimental information.
Acknowledgements
This study was supported by Priority Research Center Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2009-0093815), Republic of Korea.
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