沉香中2-(2-苯乙基)色酮类成分及其胃保护活性

2-(2-Phenylethyl)chromones from resinous wood of Aquilariae Lignum Resinatum and its gastroprotective effects

目的研究沉香Aquilariae Lignum Resinatum的2-(2-苯乙基)色酮类成分及其胃黏膜上皮细胞保护活性。方法采用硅胶和ODS等多种色谱技术对沉香中2-(2-苯乙基)色酮进行分离纯化,结合波谱数据及其理化性质对化合物进行结构鉴定;采用牛磺胆酸诱导人胃黏膜上皮细胞GES-1损伤模型对分离得到的单体化合物进行胃黏膜保护活性筛选。结果从沉香醋酸乙酯萃取部位中分离得到5个化合物,分别鉴定为(5R,6S,7S)-5,6,7-三羟基-2-苯乙基-5,6,7,8-四氢-4H-色烯-4-酮(1)、(6S,7S,8S)-6,7,8-三羟基-2-(3-羟基-4-甲氧基)-5,6,7,8-四氢-4H-色烯-4-酮(2)、oxidoagarochromone C(3)、rel-(1αR,2R,3R,7βR)-1α,2,3,7β-tetrahydro-2,3-dihydroxy-5-[2-(4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzopyran-7-one(4)、沉香色酮J(5)。化合物3~5在20μmol/L浓度时,相对模型组细胞存活率分别提高(27.17±4.38)%、(16.02±2.95)%和(14.84±2.86)%。结论化合物1为新化合物,命名为四氢色酮N,通过计算电子圆二色谱(electronic circular dichroism,ECD)确定了其绝对构型。化合物3~5能显著改善牛磺胆酸诱导的人胃黏膜上皮细胞GES-1损伤,表现出一定的胃黏膜上皮细胞保护活性。

Objective To investigate the 2-(2-phenylethyl)chromone constituents from Chenxiang(Aquilariae Lignum Resinatum)and its gastroprotective effects.Methods The chemical constituents were isolated and purified by silica gel,and ODS column chromatographies.Their structures were determined on the basis of their physicochemical properties and spectroscopic data.The isolates were evaluated for their protective effects on taurocholic acid(TCA)-induced gastric mucosal GES-1 cell injury.Results Five compounds were isolated from the ethyl acetate-soluble fraction of Aquilariae Lignum Resinatum and their structures were identified as(5R,6S,7S)-5,6,7-trihydroxyl-2-phenethyl-5,6,7,8-tetrahydro-4H-chromen-4-one(1),(6S,7S,8S)-6,7,8-trihydroxyl-2-(3-hydroxyl-4-methoxylphenylethyl)-5,6,7,8-tetrahydro-4H-chromen-4-one(2),oxidoagarochromone C(3),rel-(1αR,2R,3R,7βR)-1α,2,3,7β-tetrahydro-2,3-dihydroxy-5-[2-(4-methoxyphenyl)ethyl]-7H-oxireno[f][1]benzopyran-7-one(4)and aquilarone J(5).Compounds 3—5 could significantly protect TCA-induced GES-1 cell injury,with increase of cell viabilities by(27.17±4.38)%,(16.02±2.95)%and(14.84±2.86)%,respectively.Conclusion Compound 1 is a new compound named tetrahydrochromone N.Its absolute configuration was determined by ECD calculation.Compounds 3—5 significantly recovered the decreased GES-1 cell viability induced by TCA injury,showing a significant protective effect of gastric mucosal epithelial cells.