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Five new epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromones from Chinese agarwood by artificial holing

文献类型： 外文期刊

作者： Li, Wei 1 ; Liao, Ge 1 ; Wang, Hao 1 ; Dong, Wen-Hua 1 ; Yang, Li 1 ; Kong, Fan-Dong 1 ; Cai, Cai-Hong 1 ; Wang, Jun 1 ; Man 1 ;

作者机构： 1.Chinese Acad Trop Agr Sci, Inst Trop Biosci & Biotechnol, Minist Agr, Key Lab Biol & Genet Resources Trop Crops, Haikou 571101, Hainan, Peoples R China

2.Hainan Key Lab Res & Dev Nat Prod Li Folk Med, Haikou 571101, Hainan, Peoples R China

3.Hainan Engn Res Ctr Agarwood, Haikou 571101, Hainan, Peoples R China

4.Univ Debrecen, Dept Organ Chem, POB 400, H-4002 Debrecen, Hungary

关键词： Agarwood; Artificial holing; Chiral tetrahydrochromone; TDDFT-ECD; AChE inhibitory activity

期刊名称：FITOTERAPIA （ 影响因子：2.882； 五年影响因子：3.202 ）

ISSN： 0367-326X

年卷期： 2019 年 134 卷

页码：

收录情况： SCI

摘要： Five optically active epoxy-5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone derivatives (1-5) with four chirality centers in the condensed cyclohexene ring were isolated from artificial holing agarwood originating from Aquilaria sinensis (Lour.) Gilg. Their structures were elucidated by spectroscopic techniques (UV, IR, 1D and 2D NMR) and MS analyses. The absolute configuration of 2 was elucidated by TDDFT-ECD calculations and ECD spectra of 1, 3-5 allowed their configurational assignment as well. All of the new compounds contained a condensed oxirane ring, and compound 1 was the only 6,7-epoxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone derivative that has ever been found in agarwood. AChE inhibitory activity was tested for the first time of these new compounds by using modified Ellman's colorimetric method. Compounds 3 and 5 exhibited inhibitory activity against AChE with IC50 value of 441.6, and 155.6 mu M, respectively.

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