刀豆化学成分及其雌激素样活性研究

Chemical constituents from the seeds of Canavalia gladiata and their estrogen⁃like activities

目的研究刀豆化学成分及其雌激素样活性。方法刀豆75%乙醇提取物采用多种色谱进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。采用稳定转染雌激素受体报告基因(ER-Luc)的人乳腺癌细胞(MCF-7)细胞评价雌激素样活性。结果从中分离得到12个化合物,分别鉴定为山柰酚-3-O-洋槐糖苷(1)、kaempferol3-O-[O-β-D-apio-D-furanosyl(1→2)-O-[α-L-rhamno-pyranosyl(1→6)]-β-D-galactopyranoside(2)、山柰酚-3-O-(2′-O-β-D-葡酰)-β-D-洋槐糖苷(3)、槲皮素-3-O-β-D-葡萄糖苷(4)、槲皮素-3-O-(6″-O-没食子酰基)-β-D-葡萄糖苷(5)、异杨梅苷(6)、杨梅素-3-O-芸香糖苷(7)、(3-ethenylphenyl)-1,2-ethanediol(8)、1,3,6-三没食子酰基葡萄糖苷(9)、breyniosideA(10)、4-hydroxy-3-methoxyphenol-1-O-β-D-(6′-O-galloyl)glucoside(11)、maesopsin-6-O-β-D-glucopyranoside(12)。化合物1、3~5、8~9在浓度为50μmol/L,化合物2、12在浓度为100μmol/L时表现出雌激素样活性。结论所有化合物均为首次从刀豆属植物中分离得到。化合物1、3~5、8~9雌激素样活性强于2、12。

AIM To study the chemical constituents from seeds of Canavalia gladiata(Jacq.)DC.,and their estrogen-like activities.METHODS The 75%ethanol extract from the seeds of C.gladiata was isolated and purified by various chromatography,then the structures of obtained compounds were identified by physicochemical properties and spectral data.The estrogen-like activities were evaluated by human breast cancer cells(MCF-7)stably transfected with estrogen receptor reporter gene(ER-Luc).RESULTS Twelve compounds were isolated and identified as biorobin(1),kaempferol 3-O-[O-β-D-apio-D-furanosyl(1→2)-O-[α-L-rhamno-pyranosyl(1→6)]-β-D-galactopyranoside(2),kaempferol 3-O-{β-D-glucopyranosyl(1→2)-[α-L-rhamonopyranosyl(1→6)]-β-D-galactopyranoside}(3),iso-quercitrin(4),quercetin 3-O-(6″-O-galloyl)-β-D-glucoside(5),isomyricitrin(6),myricetin-3-O-rutinoside(7)(3-ethenylphenyl)-1,2-ethanediol(8),1,3,6-tri-O-galloyl-β-D-glucopyranose(9),breynioside A(10),4-hydroxy-3-methoxyphenol-1-O-β-D-(6′-O-galloyl)glucoside(11),maesopsin-6-O-β-D-glucopyranoside(12).Compounds 1,3-5,8-9 in the concentration of 50μmol/L,and compounds 2,12 in 100μmol/L showed estrogen-like activities.CONCLUSION All compounds are isolated from the gene Canavalia for the first time.Compounds 1,3-5,8-9 showed stronger estrogen-like activities than compounds 2 and 12.