驱虫斑鸠菊化学成分及酪氨酸酶抑制活性研究

Chemical Constituents and Tyrosinase Inhibition Activities of the fruits from Vernonia anthelmintica

目的:研究驱虫斑鸠菊的化学成分,并探讨其中的黄酮类化合物对酪氨酸酶活性的影响。方法:驱虫斑鸠菊80%乙醇提取物通过硅胶柱层析、Sephadex LH-20柱和制备高效液相色谱等多种色谱方法分离纯化,并根据理化性质和波谱技术鉴定各单体化合物的结构。采用蘑菇酪氨酸酶多巴速率氧化法,考察分离得到的黄酮类化合物对酪氨酸酶抑制活性作用。结果:从驱虫斑鸠菊的果实中分离得到14个化合物,分别鉴定为:N-乙酰基吲哚-3-甲醛(1)、1-乙基吲哚-3-甲酸(2)、豆甾醇(3)、圣草酚(4)、芹菜素(5)、紫铆查尔酮(6)、紫铆素(7)、异鼠李素(8)、硫黄菊素(9)、木犀草素(10)、咖啡酸(11)、原儿茶酸(12)、3,5-二咖啡酰奎宁酸甲酯(13)、3,4-二咖啡酰奎宁酸甲酯(14)。化合物9对酪氨酸酶的抑制活性最强,IC50=0.424 mmol/L。结论:其中,化合物1、2、9、12~14为首次从该植物中分离得到,化合物1、2、9为首次从该属植物中分离得到。化合物9可作为一种潜在的天然酪氨酸酶抑制剂进行深入研究。

Objective： To study the chemical constituents of the fruits from Vernonia anthelmintica,and to study the effects of flavonoids on the activity of mushroom tyrosinase. Methods： The chemical constituents of 80% ethanol extract of Vernonia anthelmintica were isolated and purified by various chromatographic methods including silica gel,Sephadex LH-20 column chromatography,and preparative HPLC. Their structures were elucidated on the basis of spectroscopic data and physico-chemical methods. The inhibitory activity of flavonoids against tyrosinase was evaluated by measuring the oxidation rate of DL-dopa. Results： Fourteen compounds were isolated from the fruits of Vernonia anthelmintica,and the structures were identified as N-acetylindole-3-carboxaldehyde（ 1）,1-ethylindole-3-carboxylic acid（ 2）,stigmasterol（ 3）,eriodictyol（ 4）,apigenin（ 5）,butein（ 6）,butin（ 7）,isorhamnetin（ 8）,sulphuretin（ 9）,luteolin（ 10）,caffeic acid（ 11）,protocatechuic acid（ 12）,3,5-O-dicaffeoylquinic acid methyl ester（ 13）,3,4-O-dicaffeoylquinic acid methyl ester（ 14）. Compound 9 was a strong inhibitor of mushroom tyrosinase,IC50= 0. 424 mmol/L. Conclusion： Compounds 1,2,9,12 ~ 14 are isolated from this plant for the first time,compounds 1,2,9 are islolated from this genus for the first time. Compound 9 can be used as a potential natural tyrosinase inhibitor for further research.