阿魏酰氨基酸乙酯的合成及其抗氧化活性研究  

Synthesis and anti-oxidant activity of feruloylamino acid ethyl ester

作　　者：郭晓丹 宋京九 祝钧[1] GUO Xiao-dan;SONG Jing-jiu;ZHU Jun(School of Science,Beijing Technology and Business University,Beijing 100048,China)

机构地区：[1]北京工商大学理学院,北京100048

出　　处：《日用化学工业》2020年第9期624-628,共5页China Surfactant Detergent & Cosmetics

基　　金：北京市高等学校教学名师支持项目(19005753005);2019年研究生科研项目提升计划。

摘　　要：以阿魏酸和氨基酸乙酯盐酸盐为原料,1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC·HCl)和1-羟基苯并三唑(HOBt)为催化剂,采用EDC缩合法合成阿魏酰蛋氨酸乙酯(Ⅰ)、阿魏酰异亮氨酸乙酯(Ⅱ)、阿魏酰苏氨酸乙酯(Ⅲ)和阿魏酰苯丙氨酸乙酯(Ⅳ)。利用核磁共振氢谱(1 H NMR)和高效液相色谱-质谱(HPLC-MS)对产物结构进行表征,并且比较了阿魏酰氨基酸乙酯和阿魏酸在清除DPPH自由基和ABTS自由基方面的活性。结果表明:合成的4种阿魏酰氨基酸乙酯能够较好的清除自由基,且清除率均大于阿魏酸单体;阿魏酰苯丙氨酸乙酯(Ⅳ)清除DPPH自由基和ABTS自由基能力最强,IC 50分别为37.567和1.689µmol/L。红细胞溶血实验表明:合成的阿魏酰氨基酸衍生物Ⅰ、Ⅲ、Ⅳ的刺激性均小于阿魏酸。Ferulic methionine ethyl ester(Ⅰ),feruli isoleucine ethyl ester(Ⅱ),feruli threonine ethyl ester(Ⅲ)and feruli phenylalanine ethyl ester(Ⅳ)were synthesized by EDC condensation using ferulic acid and amino acid ethyl ester hydrochloride as raw materials,and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride(EDC·HCl)and 1-hydroxybenzotriazole(HOBt)as catalysts.The structure of the products was characterized by 1 H NMR and HPLC-MS,and the activities of ferulic acid and ethyl ferulic acid in scavenging DPPH and ABTS free radicals were compared.The results show that the four kinds of ferulic acid ethyl ester scavenged free radicals better,and the scavenging rates are higher than that of ferulic acid monomer.The ferryl phenylalanine ethyl ester(Ⅳ)has the strongest ability to scavenge DPPH free radicals and ABTS free radicals,with IC 50 of 37.567 and 1.689μmol/L,respectively.The red blood cells hemolysis test show that the irritation of the synthesized derivatives of ferulic acidⅠ,ⅢandⅣis less than that of ferulic acid.

关 键 词：阿魏酸 阿魏酰氨基酸酯衍生物 DPPH自由基 ABTS自由基 化妆品添加剂 

分 类 号：TQ658[化学工程—精细化工]