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以蒸馏水为溶剂回流提取水飞蓟种子,提取物依次过D101大孔树脂、MCI树脂、MPLC色谱、HPLC色谱等色谱分离纯化得到7个化合物。经NMR解析确定化合物1~7分别为tricin 4’-O-[threo-β-guaiacyl-(7″-O-methyl)-glyceryl]ether(1),tricin 4’-O-[erythro-β-guaiacyl-(7″-O-methyl)-glyceryl]ether(2),5’-methoxyhydnocarpin-D(3),palstatin(4),(8R,7’S,8’R)-5,5’-dimethoxy-7-oxolariciresinol 9’-O-D-xylopyranoside(5),9-O-D-glucopyranoside(6),(-)-haplomyrtoside(7)。化合物1,3~5具有较强的抗流感病毒(H5N1)活性,IC_(50)分别为0.65,0.21,0.32和0.56μmol·L~(-1),SI(SI=TC50/IC_(50))分别为12.5,3.5,10.6,7.8。化合物1,2,6,7具有较好的抗人肝癌细胞(Hep G-2)活性,IC_(50)分别为0.35,0.25,0.53,0.66μmol·L~(-1)。化合物1~7为从该植物中首次分离得到。
Silybum marianum seeds were extracted with distilled water as solvent, and the compounds were separated and purified by D101 macroporous resin, MCI resin, MPLC and HPLC. Compounds 1 to 7 were confirmed to be tricin 4’-O- [threo-β-guaiacyl- (7 "-O-methyl) -glyceryl] ether (1) and tricin 4’-O- [erythro-β- 5’-methoxyhydnocarpin-D (3), palstatin (4), (8R, 7’S, 8’R) -5,5’-dimethoxy- 7-oxolariciresinol 9’-OD-xylopyranoside (5), 9-OD-glucopyranoside (6), (-) - haplomyrtoside (7). Compounds 1, 3 and 5 showed strong anti-influenza virus (H5N1) activity with IC50 of 0.65,0.21,0.32 and 0.56μmol·L -1, SI (SI = TC50 / IC 50) ) Were 12.5, 3.5, 10.6, 7.8 respectively. Compounds 1, 2, 6, and 7 showed good activity against Hep G-2 cells with IC50 of 0.35,0.25,0.53,0.66μmol·L -1, respectively. Compounds 1 to 7 were isolated from this plant for the first time.