5,6,7,8-Tetrahydro-2-(2-phenylethyl)chromones from artificial agarwood of Aquilaria sinensis and their inhibitory activity against acetylcholinesterase

被引:46
作者
Liao, Ge [2 ]
Mei, Wen-Li [1 ]
Kong, Fan-Dong [1 ]
Li, Wei [1 ]
Yuan, Jing-Zhe [1 ]
Dai, Hao-Fu [1 ]
机构
[1] Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Key Lab Biol & Genet Resources Trop Crops, Minist Agr, Haikou 571101, Peoples R China
[2] Hainan Univ, Coll Hort & Landscape Architecture, Haikou 570228, Peoples R China
关键词
Aquilaria sinensis; Thymelaeaceae; Artificial agarwood; 5,6,7,8-Tetrahydro-2-(2-phenylethyl)chromones; AChE inhibitory activity; FLIGHT MASS-SPECTROMETRY; CHINESE EAGLEWOOD; 2-(2-PHENYLETHYL)CHROMONE DERIVATIVES; REAL-TIME; WOOD;
D O I
10.1016/j.phytochem.2017.04.011
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Thirteen previously undescribed 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones named tetrahydrochromone A-M, together with nine known ones, were isolated from artificial agarwood (induced by holing) originating from Aquilaria sinensis (Lour.) Gilg. The structures of these compounds were unambiguously determined based on extensive NMR spectroscopic analyses, and the absolute configuration was resolved by CD analyses, X-ray crystallographic, chemical and Mosher's method. Tetrahydrochromone A, B, K-M, and Oxidoagarochromone An exhibited inhibitory activity against AChE with the percentage inhibition range from 17.5% to 47.9% (with Tacrine as the positive control; inhibition ratio: 66.7%) when tested at 50 mu g/mL. Tetrahydrochromone A-E, F-J feature one methoxy and three hydroxys linked at the cyclohexene ring rather than usual four hydroxys, and tetrahydrochromone K-M represent the first examples of 7,8-epoxy tetrahydrochromones. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:98 / 108
页数:11
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