碳链长度对咖啡酸酯的抗氧化及抗增殖活性的影响  

The Effect for Lengths of the Alkyl Side Chain on the Antioxidant and Antiproliferative Activity of Caffeic Acid Phenethyl Ester

作　　者：罗辉[1] 王琪[2] 

机构地区：[1]井冈山大学医学院,江西吉安343009 [2]兰州大学化学化工学院,甘肃兰州730000

出　　处：《江西师范大学学报（自然科学版）》2012年第4期421-424,共4页Journal of Jiangxi Normal University(Natural Science Edition)

基　　金：江西省教育厅2012年度科技课题(GJJ12476)资助项目

摘　　要：咖啡酸苯乙酯（caffeic acid phenethyl ester,CAPE）是蜂胶中的主要活性成分,具有显著的抗氧化及抗肿瘤活性.研究了具有不同边链长度的CAPE类似物（咖啡酸丁酯、咖啡酸己酯、咖啡酸辛酯和咖啡酸十六烷基酯）对水溶性偶氮引发剂2,2′-偶氮二（2-脒基丙烷）二盐酸盐（AAPH）诱导的血红细胞膜氧化损伤的保护作用.其抗氧化活性顺序为：咖啡酸辛酯〉CAPE~咖啡酸丁酯〉咖啡酸己酯〉咖啡酸十六烷基酯.同时,测定了这些化合物抑制人肺癌细胞A549增殖活性,其活性顺序为：咖啡酸丁酯〉CAPE〉咖啡酸辛脂〉咖啡酸己脂〉咖啡酸十六烷基脂.研究结果表明：与CAPE相比,咖啡酸辛酯的抗氧化活性和咖啡酸丁酯抑制A549细胞增殖活性优于母体分子.咖啡酸酯的抗氧化活性和抑制A549细胞增殖的活性与其边链长度（亲脂性）并不呈简单的线性关系.＂合适＂的亲脂性和胞内的定位是影响化合物这些活性的重要因素.Caffeic acid phenethyl ester（CAPE） has been identified as an active component of propolis,and its antioxidant and cancer chemoprevention activities have attracted considerable attention.The antioxidant capacity of CAPE and caffeates with various lengths of the alkyl side chain against 2,2′-azobis（2-amidinopropane） hydrochloride（AAPH）-induced lipid peroxidation of human erythrocyte ghosts were evaluated.The antioxidant activity order was octyl caffeate〉CAPE〉butyl caffeate〉 hexyl caffeate〉hexadecyl caffeate.Furthermore,their antiproliferative effect against human lung adenocarcinoma A549 cells was also assessed with the activity order being butyl caffeate〉CAPE〉octyl caffeate〉hexyl caffeate〉hexadecyl caffeate.Octyl and butyl caffeates exhibited significantly higher antioxidant and antiproliferative activities than CAPE,respectively.It was found that the chain length affects the activities of caffeates in a nonlinear manner,and the suitable lipophilicity and intracellular localization of compounds are is the important parameters in determining their activites.

关 键 词：咖啡酸苯乙酯 抗氧化剂 脂质过氧化 构效关系 抗增殖 

分 类 号：O629[理学—有机化学]