Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (02): 312-318.DOI: 10.6023/cjoc201210051 Previous Articles     Next Articles



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 发布日期:2012-11-26
  • 通讯作者: 林茂

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 Published:2012-11-26

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