有机化学 ›› 2013, Vol. 33 ›› Issue (02): 312-318.DOI: 10.6023/cjoc201210051 上一篇    下一篇

研究论文

氧化偶联反应和酸催化反应制备活性买麻藤醇二聚体衍生物

姚春所, 林茂, 杨庆云   

  1. 中国医学科学院 北京协和医学院 药物研究所 天然药物活性物质与功能国家重点实验室 北京 100050
  • 收稿日期:2012-10-29 修回日期:2012-11-17 出版日期:2013-02-25 发布日期:2012-11-26
  • 通讯作者: 林茂 E-mail:linmao@imm.ac.cn

Preparation of Active Gnetol Dimers by Oxidative Coupling Reaction and Acid-Catalyzed Dimerization

Yao Chunsuo, Lin Mao, Yang Qingyun   

  1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050
  • Received:2012-10-29 Revised:2012-11-17 Online:2013-02-25 Published:2012-11-26

以天然得到的买麻藤醇为原料, 以FeCl3·6H2O为氧化剂进行氧化偶联反应和酸催化二聚反应, 获得了2个新的买麻藤醇二聚体及一个新的苯基萘衍生物: 4-[1-(2,6-二羟基苯基)-2-(3,5-二羟基苯基)乙基]-2-[(1E)-2-(3,5-二羟基苯基)乙烯基]-1,3-苯二醇(1), 2-[1-(2,6-二羟基苯基)-2-(3,5-二羟基苯基)乙基]-5-[(1E)-2-(2,6-二羟基苯基)乙烯基]-1,3-苯二醇(2)和4-(6,8-二甲氧基-2-萘基)-1,3-苯二醇(3). 应用波谱分析的方法确定了它们的结构, 并分别讨论了它们可能的形成机理. 其中, 化合物12首次为人工合成的二苯乙烯链状二聚体. 活性测试结果表明, 化合物1, 23显示有较强的抗氧化活性, 其IC50值分别为6.29×10-9, 4.19×10-6和2.96×10-5 mol·L-1; 化合物2还显示有较强的抗炎活性.

关键词: 买麻藤醇二聚体, 氧化偶联反应, 生物活性

Oxidative coupling reaction with FeCl3?6H2O as oxidant and acid-catalyzed dimerization of natural gnetol in methanol afforded two new gnetol dimers and one new phenyl naphthalene derivative: 4-[1-(2,6-dihydroxyphenyl)-2-(3,5- dihydroxyphenyl)ethyl]-2-[(1E)-2-(3,5-dihydroxyphenyl)ethenyl]-1,3-benzenediol (1), 2-[1-(2,6-dihydroxyphenyl)-2-(3,5-di- hydroxyphenyl)ethyl]-5-[(1E)-2-(2,6-dihydroxyphenyl)ethenyl]-1,3-benzenediol (2) and 4-(6,8-dimethoxyl-2-naphthalenyl)- 1,3-benzenediol (3). Their structures were elucidated on the basis of spectral analysis, and their possible formation mechanisms were discussed. 1 and 2 were new linear stilbene dimers synthesized for the first time. Pharmacological tests showed 1, 2 and 3 to exhibit potent anti-oxidation activity with IC50 values of 6.29?10-9, 4.19?10-6, and 2.96?10-5 mol稬-1, respectively, and 2 was shown to have potent anti-inflammatory activity.

Key words: gnetol dimer, oxidative coupling reaction, bioactivity