Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China; Hainan Key Laboratory for Research and Development of Natural Products from Li Folk Medicine, Haikou 571101, China; Hainan Engineering Research Center of Agarwood, Haikou 571101, China.
Key Laboratory of Biology and Genetic Resources of Tropical Crops, Ministry of Agriculture, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China.
Fitoterapia. 2019 Apr;134:182-187. doi: 10.1016/j.fitote.2019.02.031. Epub 2019 Feb 28.
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 IC value of 441.6, and 155.6 μM, respectively.
从人工打孔沉香（Aquilaria sinensis (Lour.) Gilg）中分离出五个光学活性的环氧-5,6,7,8-四氢-2-(2-苯乙基)色酮衍生物（1-5），它们在稠合环己烯环中有四个手性中心。通过光谱技术（UV、IR、1D 和 2D NMR）和 MS 分析确定了它们的结构。通过 TDDFT-ECD 计算和 1、3-5 的 ECD 光谱确定了 2 的绝对构型，也确定了它们的构型分配。所有新化合物都含有一个稠合的环氧乙烷环，化合物 1 是沉香中唯一发现的 6,7-环氧-2-(2-苯乙基)-5,6,7,8-四氢色酮衍生物。首次通过改良的 Ellman 比色法测试了这些新化合物对乙酰胆碱酯酶的抑制活性。化合物 3 和 5 对乙酰胆碱酯酶表现出抑制活性，IC 值分别为 441.6 和 155.6 μM。
