含氰基白藜芦醇衍生物的合成及抗癌活性研究  

Synthesis and antitumor activity study of cyano-containing resveratrol derivatives

作　　者：马军[1] 田玉顺[1] 

机构地区：[1]延边大学药学院,吉林延吉133002

出　　处：《延边大学医学学报》2016年第1期31-34,共4页Journal of Medical Science Yanbian University

基　　金：国家自然科学基金;NO.81260226

摘　　要：[目的]合成一系列二苯乙烯双键结构上含有氰基的白藜芦醇衍生物,并测定其体外抗癌活性.[方法]以3,5-二羟基苯甲酸为原料,经甲基化、还原、取代、Abozove重排、Wittig-Hornor反应和Knoevenegal反应合成白藜芦醇及其衍生物,利用1 H-NMR确认其结构,采用MTT法观察每种化合物对HCT116人结肠癌细胞的增殖抑制作用.[结果]二苯乙烯双键结构上含有氰基的白藜芦醇B环4′位引入甲氧基、乙氧基时其IC50值均小于0.20μmol/L,引入正丙氧基时IC50值小于15.00μmol/L,此3种化合物对HCT116人结肠癌细胞的增殖抑制作用均强于白藜芦醇(IC50=64.46μmol/L),当碳数超过3个时其IC50值均大于白藜芦醇的IC50值.[结论]二苯乙烯双键上含有氰基的白藜芦醇B环4′位引入甲氧基、乙氧基或正丙氧基时对HCT116人结肠癌细胞有增殖抑制作用,但正丁氧基等侧链碳数超过3个的羟基烷基化产物的增殖抑制作用较弱.OBJECTIVE A series of resveratrol derivative which containing a cyano group on vinyl aouoie bond structure of stilbene were synthesized and evaluated their antitumor activitiesin vitro. METHODS 3,5-dihydroxybenzoic acid acted as a starting material to synthesize resveratrol and its derivatives by a series of reactions such as methylation, reduction, substitution, abozove rearrangement, wittig-hornor reaction and knoevenagel reaction, and the structures were confirmed by 1H-NMR. Then inhibition of cell proliferationwas evaluated by MTT assay on human colon cancer cell HCTll6. RESULTS When para-hydroxy group of B ring was changed with para-methoxy or para-ethoxy group, the IC50 values were less than 0.20 μmol/L, and when para-hydroxy group of B ring was changed with n-propoxy group, the IC50 value was less than 15.00 μmol/L. Those derivatives had better anti-tumor activities than resveratrol （IC50 = 64. 46 μmol/L）. But when 4＇-OH group of B ring was changed with a chain whichhad more than three carbons such as n-butoxy, the IC50 value was higher than resveratrol＇ s. CONCLUSION When 4＇-OH group of B ring was changed with methoxy, ethoxy or n-propoxyin the resveratrol which introduced of cyano group on vinyl double bond structure of stilbene, the anti-tumor propertieswere stronger than resveratrol, but when the carbon numbersweremore than three, the anti-tumor activities were sharply decreased on HCT116 cells.

关 键 词：白藜芦醇 衍生物 MTT法 抗癌活性 

分 类 号：R914.5[医药卫生—药物化学]