Liao Ge, Mei Wen-Li, Kong Fan-Dong, Li Wei, Yuan Jing-Zhe, Dai Hao-Fu
College of Horticulture and Landscape Architecture, Hainan University, Haikou, 570228, PR 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, PR China.
Phytochemistry. 2017 Jul;139:98-108. doi: 10.1016/j.phytochem.2017.04.011. Epub 2017 Apr 21.
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 μg/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.
从白木香（Aquilaria sinensis (Lour.) Gilg）人工结香（打孔诱导）中分离得到了13个此前未被描述的5,6,7,8-四氢-2-(2-苯乙基)色酮，命名为四氢色酮A - M，以及9个已知化合物。基于广泛的核磁共振光谱分析明确确定了这些化合物的结构，并通过圆二色光谱分析、X射线晶体学、化学方法和莫舍尔法解析了其绝对构型。在50μg/mL的浓度下进行测试时，四氢色酮A、B、K - M和氧化沉香色酮An对乙酰胆碱酯酶表现出抑制活性，抑制率范围为17.5%至47.9%（以他克林作为阳性对照；抑制率：66.7%）。四氢色酮A - E、F - J在环己烯环上连接一个甲氧基和三个羟基，而非通常的四个羟基，并且四氢色酮K - M是7,8 - 环氧四氢色酮的首个实例。
