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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 02: 312 - 318

DOI: https://doi.org/10.6023/cjoc201210051

Articles

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

  • Yao Chunsuo ,
  • Lin Mao ,
  • Yang Qingyun
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  • 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 date: 2012-10-29

  Revised date: 2012-11-17

  Online published: 2012-11-26

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Abstract

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

Cite this article

Yao Chunsuo , Lin Mao , Yang Qingyun . Preparation of Active Gnetol Dimers by Oxidative Coupling Reaction and Acid-Catalyzed Dimerization[J]. Chinese Journal of Organic Chemistry, 2013 , 33(02) : 312 -318 . DOI: 10.6023/cjoc201210051

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