菜油基长链辣椒素酯小型化合物库的制备与初步生物活性  

Synthesis of a Small Library of Long-chain Capsinoids with Acyl Moiety of Colza Oil and Their Preliminary Bioactivity

作　　者：董新荣[1,2] 刘仲华[2] 李雨虹[3] 谢达平[3] 何理[4] 

机构地区：[1]湖南农业大学理学院 [2]湖南农业大学天然产物研究中心 [3]湖南农业大学生物科学与技术学院,长沙410128 [4]华中农业大学生命科学技术学院,武汉430070

出　　处：《天然产物研究与开发》2009年第5期792-795,共4页Natural Product Research and Development

基　　金：国家科技部十五科技重点项目(No.2004BA542C);湖南省自然科学基金(07JJ6026)

摘　　要：以脂肪酶在有机介质中催化食用菜油与香草醇直接转酯反应合成了一个含菜油酰基的长链辣椒素酯小型化合物库。反应条件:5 mmol香草醇,2.5 mmol食用菜油溶于100 mL丙酮中,加入0.5 g固定化脂肪酶(Novo 435),置于30℃的摇床上以200 r/min反应24 h。分离固定化酶后,反应物以硅胶柱色谱分离,得到长链辣椒素酯小型库,收率34.1%。这个化合物库主要由亚麻酸香草醇酯(1)、亚油酸香草醇酯(2)、软脂酸香草醇酯(3)、油酸香草醇酯(4)、硬脂酸香草醇酯(5)、花生一烯酸香草醇酯(6)、芥酸香草醇酯(7)组成;它在50μg/mL时对PPARγ模型具有弱的激活作用,激活倍数为1.5。用制备性高效液相色谱对这个化合物库进行分离,得到化合物1～4、7,以1HNMR确证了结构,其中化合物7未见文献报道。In this paper, a small library of long-chain capsinoids （LCs）with acyl of colza oil was synthesized directly by transesterification of vanillyl alcohol with colza oil using lipase as catalyst in organic media. The mixture of 0.5 g immobilized lipase Novo 435 and 100 mL acetone solution containing 5 mmol vanillyl alcohol and 2.5 rmnol colza oil was shaken for 24 h in a temperature-controlled incubator shaker at 200 r/min and 30 ℃. The product was purified by silica gel chromatography with 34. 1% yield and a small natural long-chain capsinoids library,which was composed of vanillyl linolenate （1）, vanillyl linoleate （2）, vanillyl palmitate （3）, vanillyl oleate （4）, vanillyl stearate （ 5 ）, vanillyl eicosenoate （6） and vaniUyl docosenoate（7）mainly, was established and displays a low activity as a PPARγ agonist with activity times of 1.5 at 50 μg/mL. Compounds 1,2,3,4,7 were separated from the LCs by preparative reversed-phase high per- formance liquid chromatography and characterized by 1 H NMR and compound 7 was first reported.

关 键 词：辣椒素酯 脂肪酶 酶催化合成 有机介质 菜子油 

分 类 号：Q946.91[生物学—植物学] R284.1[医药卫生—中药学]