有机化学 ›› 2013, Vol. 33 ›› Issue (9): 1982-1987.DOI: 10.6023/cjoc201303030 上一篇    下一篇

研究简报

酸催化α-细辛脑二聚反应及其产物抗癌活性研究

徐盈盈a, 梁志武a, 刘开建a, 陈辉b, 向建南a   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 湖南大学生物学院 长沙 410082
  • 收稿日期:2013-03-19 修回日期:2013-05-23 发布日期:2013-05-31
  • 通讯作者: 向建南 E-mail:jnxiang@hnu.cn
  • 基金资助:

    国家自然科学基金(No. 21276068);湖南省自然科学基金(No. 11JJ5008);湖南省科技厅重点(No. 2010SK2001)资助项目

Acid-Catalyzed Dimerization of α-Asarone and Anticancer Evaluation of the Dimers

Xu Yingyinga, Liang Zhiwua, Liu Kaijiana, Chen Huib, Xiang Jiannana   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b School of Biology, Hunan University, Changsha 410082
  • Received:2013-03-19 Revised:2013-05-23 Published:2013-05-31
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21276068), the Natural Science Foundation of Hunan Province (No. 11JJ5008), the Department of Science and Technology Foundation of Hunan Province (No. 2010SK2001)

E-1-(2,4,5-三甲氧基苯基)-2-丙烯(α-细辛脑)为原料, 酸催化选择性合成脱碳木脂素类化合物a及二氢化茚类化合物b, 其结构经核磁﹑质谱和元素分析表征确认. 研究了催化剂种类、反应溶剂和温度等条件对两种化合物产率比的影响, 45 ℃时, HCl为催化剂, 乙醇为溶剂, 化合物a/b的总收率为98% (a: 41%, b: 57%); 30 ℃时, AlCl3为催化剂, 乙醇为溶剂, 化合物a的产率可达75%, 没有b生成, 对a的选择性为100%; 45 ℃时, 以BF3·Et2O溶液为催化剂, CH2Cl2为溶剂, 化合物a的产率为20%, 化合物b的产率可达60%. 采用MTT法, 分别评价了化合物a/b对四种癌细胞(MCF-7, Bel-7402, A549及Hela)的抑制作用, 结果表明: 化合物a对MCF-7, Hela (IC50值分别为: 120.2, 117.3 μmol·L-1), 化合物b则对MCF-7, A549 (IC50值分别为: 66.1, 72.4 μmol·L-1)显示出比相同条件下5-Fu更好的抗癌抑制活性. 同时, 研究了a/b浓度﹑作用时间对癌细胞抑制率的影响.

关键词: 二氢化茚, 脱碳木脂素, 选择性, 抗癌抑制活性

The decarbonization of lignan a and dihydroindene b were synthesized through α-asarone by acid-catalyzed. Compounds a/b were identified by 1H NMR, 13C NMR, MS and elemental analysis. The effects of catalysts, solvents and temperature on yields of a/b have been evaluated. The total yield of a/b reached 98% (a: 41%, b: 57%) with HCl as catalyst and ethanol as solvent at 45 ℃. The yield of compound a was up to 75% with AlCl3 as catalyst and ethanol as solvent at 30 ℃, b was not formed in this condition, and the selectivity of a was 100%. When using BF3·Et2O as catalyst and methylene chloride as solvent at 45 ℃, the yield of compound a was 20% and b was formed in yield of 60%. The cytotoxic activities of two compounds against MCF-7, Bel-7402, A549 and Hela were evaluated in vitro by the MTT assay. The results indicated that compounds a/b exhibited better cytotoxic activities against four cancer cells than 5-Fu. Especially, the IC50 values of a to MCF-7 and Hela reached 120.2 and 117.3 μmol·L-1 as well as the IC50 of b to MCF-7 and A549 reached 66.1 and 72.4 μmol·L-1, respectively. At the same time, the concentration of a/b and time of operation to influence inhibitory activity were explored.

Key words: dihydroindene, decarbonization of lignan, selectivity, anticaner activity