菲律宾产丝沉香中2-(2-苯乙基)色酮二聚体及其胃黏膜保护活性  

2-(2-Phenylethyl)chromone dimers with gastroprotective effect from Aquilaria filaria in Philippines

作　　者：杨桃云 李薇[2] 陈惠琴[2] 吴妃 蔡彩虹[2] 梅文莉[2] 姜北 王昊[2] 戴好富 YANG Taoyun;LI Wei;CHEN Huiqin;WU Fei;CAI Caihong;MEI Wenli;JIANG Bei;WANG Hao;DAI Haofu(College of Pharmacy,Dali University,Dali 671003,China;Hainan Key Laboratory of Natural Products Research and Utilization of Li Folk Medicine,Hainan Engineering Technology Research Center of Agarwood,International Joint Research Center of Agarwood,Institute of Tropical Bioscience and Biotechnology,Chinese Academy of Tropical Agricultural Sciences,Haikou 571101,China)

机构地区：[1]大理大学药学院,云南大理671003 [2]中国热带农业科学院热带生物技术研究所,海南省沉香工程技术研究中心,沉香国际联合研究中心,海南省黎药资源天然产物研究与利用重点实验室,海南海口571101

出　　处：《中草药》2024年第24期8321-8327,共7页Chinese Traditional and Herbal Drugs

基　　金：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)。

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25μmol/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。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 25μmol/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.

关 键 词：丝沉香 沉香 2-(2-苯乙基)色酮二聚体 丝沉香酮M 胃黏膜上皮细胞 保护作用 

分 类 号：R284.1[医药卫生—中药学]