赛北紫堇中的酚类成分及其细胞毒活性研究

Phenolic compounds with cytotoxic activity from Corydalis impatiens

综合运用正相硅胶、凝胶Sephadex LH-20,ODS柱色谱以及半制备高效液相色谱等分离技术对罂粟科植物赛北紫堇的化学成分进行系统研究。运用NMR,MS等波谱方法以及理化性质结合文献数据鉴定了从赛北紫堇90%乙醇提取物中分离得到的20个酚类化合物,分别为:(3S)-5-guaiacyl-3-hydroxypentanoic methyl ester(1)、8-对羟苄基槲皮素(2)、8-对羟苄基山奈酚(3)、6-对羟苄基槲皮素(4)、槲皮素(5)、山奈酚(6)、金圣草黄素(7)、1,7-二羟基-3,8-二甲氧基(口山)酮(8)、1-羟基-2,3,5-三甲氧基(口山)酮(9)、1-羟基-2,3,4,6-四甲氧基(口山)酮(10)、p-hydroxyphenylferulate(11)、5,7-二羟基香豆素(12)、4,4′-二羟基二苄醚(13)、3-甲氧基-4-羟基苯乙醇(14)、3,4-二羟基苯乙醇(15)、对羟基苯乙醇(16)、对羟苄基乙基醚(17)、对羟基苯甲醇(18)、1,2,4-苯三酚(19)、邻二苯酚(20)。其中化合物1为一新的天然产物,2~4和7~20为首次从紫堇属中分离得到,化合物5和6为首次从赛北紫堇中分离得到。采用四甲基唑蓝法测定了20个化合物对人肝癌HepG2、SMMC-7721细胞的体外抑制活性,结果显示化合物2和3对人肝癌HepG2具有一定的抑制活性,IC50值分别为16.8和19.2μmol/L。

To investigate the chemical constituents from Corydalis impatiens,various column chromatography techniques,including silica gel,Sephadex LH-20,ODS and semi-preparative HPLC were used.The structures were identified by NMR,MS,physicochemical properties and/or comparison with literature data.As a result,twenty known phenolic compounds were isolated and identified as(3S)-5-guaiacyl-3-hydroxypentanoic methyl ester(1),8-C-p-hydroxybenzylquercetin(2),8-C-p-hydroxybenzylkaempferol(3),6-C-p-hydroxybenzylquercetin(4),quercetin(5),kaempferol(6),chrysoeriol(7),1,7-dihydroxy-3,8-dimethoxyxanthone(8),1-hydroxy-2,3,5-trimethoxyxanthone(9),1-hydroxy-2,3,4,6-tetramethoxyxanthone(10),p-hydroxyphenylferulate(11),esculetin(12),4,4′-dihydroxydibenzyl ether(13),3-methoxy-4-hydroxy-phenylethanol(14),3,4-dihydroxyphenylethanol(15),4-hydroxyphenylethanol(16),p-hydroxybenzylethyl ether(17),p-hydroxyphenylmethanol(18),1,2,4-trihydroxybenzene(19),1,2-benzenediol(20).Compound 1 is a new natural compound,2-4 and 7-20 were obtained from genus Corydalis for the first time,and 5 and 6 were isolated from this plant for the first time.All of the compounds obtained were evaluated in vitro by MTT assay against human hepatic cell line HepG2 and SMMC-7721.Compounds 2 and 3 exhibited moderate inhibition on HepG2 with IC50 values of 16.8 and 19.2 μmol/L,respectively.