[关键词]
[摘要]
目的 研究菲律宾产丝沉香植物Aquilaria filaria所产沉香中2-(2-苯乙基)色酮二聚体及其胃黏膜上皮细胞保护活性。方法 采用薄层色谱、硅胶柱色谱、半制备HPLC等多种色谱技术分离丝沉香的化学成分,经高分辨质谱、1D和2D NMR等波谱学方法鉴定化合物结构。采用牛磺胆酸诱导建立人胃黏膜上皮细胞GES-1损伤模型对化合物进行胃黏膜保护活性测试。结果 从菲律宾产丝沉香中分离鉴定了4个2-(2-苯乙基)色酮二聚体,分别为6-methoxy-2-phenethyl-7-(((5S,6R,7S,8R)-5,6,7-trihydroxy-2-(2-hydroxyphenethyl)-4-oxo-5,6,7,8-tetrahydro-4H-chromen-8-yl)oxy)-4H-chromen-4-one(1)和6''-hydroxy-4'''-methoxy-crassin B(2)、3'''-hydroxy-crassin G(3)、4'-demethoxyl-3'''-hydroxy-crassin G(4)。化合物1和4在25 μmol/L浓度时,相对模型组人胃黏膜上皮细胞存活率分别提高了(11.41±2.45)%、(5.70±2.20)%,阳性对照硫糖铝人胃黏膜上皮细胞存活率提高了(12.93±1.23)%。结论 化合物1为新化合物,命名为丝沉香酮M(aquifilarone M);化合物1~4为首次从菲律宾产丝沉香中分离得到;化合物1和4表现出人胃黏膜上皮细胞保护活性。
[Key word]
[Abstract]
Objective To investigat 2-(2-phenylethyl) chromone dimers from agarwood of Aquilaria filaria in Philippines and gastric mucosal epithelial cell protective activity. Methods All compounds were isolated by using thin-layer chromatography, silica gel column chromatography, semi-preparative HPLC and other chromatographic techniques. Their structures were elucidated based on modern spectroscopic methods, including high-resolution mass spectrometry (HRMS), 1D and 2D nuclear magnetic resonance (NMR). The isolates were evaluated for their protective effects on taurocholic acid (TCA) induced gastric mucosal GES-1 cell injury. Results A total of four 2-(2-phenylethyl) chromone dimers were isolated from A. filaria, and identified as 6-methoxy-2-phenethyl-7-(((5S,6R,7S,8R)-5,6,7-trihydroxy-2-(2-hydroxyphenethyl)-4-oxo-5,6,7,8-tetrahydro-4H-chromen-8-yl)oxy)-4H-chromen-4-one (1), 6''-hydroxy-4'''-methoxy-crassin B (2), 3'''-hydroxy-crassin G (3), 4'-demethoxyl-3'''-hydroxy-crassin G (4). Compared with the model group, the survival rate of human gastric mucosal epithelial cells was increased by (11.41 ±2.45) % and (5.70 ±2.20) % when the concentration of compounds 1 and 4 was 25 μmol/L, respectively. The positive control, sucralfate, increased cell viability by (12.93 ±1.23)%. Conclusion Compound 1 is a new compound, named aquifilarone M. Compounds 1—4 are isolated from A. filaria for the first time. Both compounds 1 and 4 show protective activity of human gastric mucosal epithelial cells.
[中图分类号]
R284.1
[基金项目]
海南省重大科技计划项目(ZDKJ2021031);财政部和农业农村部国家现代农业产业技术体系(CARS-21);中国热带农业科学院国家热带农业科学中心科技创新团队项目(CATASCXTD202406);海南省科技人才创新项目(KJRC2023C25)