ARTICLE

Preparation of Active Resveratrol Dimeric Derivatives by Oxidative Coupling Reaction Using AgOAc as Oxidant

  • Zhang Yuan ,
  • Wang Xianfen ,
  • Hou Qi ,
  • Lin Mingbao ,
  • Yao Chunsuo ,
  • Shi Jiangong
Expand
  • a 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;
    b College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024

Received date: 2014-02-05

  Revised date: 2014-03-19

  Online published: 2014-04-01

Abstract

Oxidative coupling reaction of resveratrol in methanol using silver acetate as oxidant gave seven resveratrol dimeric derivatives 17. Their structures and relative configurations were determined on the basis of spectral analysis, and their formation mechanisms were discussed, respectively. Among them, compounds 3, 4 and 5 were determined as new stilbene dimers, and compounds 6 and 7 were synthesized as natural compounds for the first time. All the compounds were evaluated for anti-inflammatory activities.

Cite this article

Zhang Yuan , Wang Xianfen , Hou Qi , Lin Mingbao , Yao Chunsuo , Shi Jiangong . Preparation of Active Resveratrol Dimeric Derivatives by Oxidative Coupling Reaction Using AgOAc as Oxidant[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 886 -892 . DOI: 10.6023/cjoc201402006

References

[1] Langcake, P.; Pryce, R. J. Experientia 1977, 33, 151.

[2] Shikishima, Y.; Takaishi, Y.; Honda, G.; Ito, M.; Takeda, Y.; Kodzhimatov, O. K.; Ashurmetov, O. Phytochemistry 2001, 56, 377.

[3] Huang, K. S.; Wang, Y. H.; Li, R. L.; Lin, M. J. Nat. Prod. 2000, 63, 86.

[4] Waffo-Teguo, P.; Lee, D.; Cuendet, M.; Merillon, J. M.; Pezzuto, J. M.; kinghorn, A. D. J. Nat. Prod. 2001, 64, 136.

[5] Cichewicz, R. H.; Kouzi, S. A.; Hamann, M.T. J. Nat. Prod. 2000, 63, 29.

[6] Hirano, Y.; Kondo, R.; Skai, K. J. Wood Sci. 2002, 48, 64.

[7] Rodriguez-Bonilla, P.; Mendez-Cazorla, L.; Lopez-Nicolas J. M.; Gaarcia-Carmona, F. Phytochemistry 2011, 72, 100.

[8] Ponzoni, C.; Beneventi, E.; Cramarossa, M. R.; Raimondi, S.; Trevisi, G.; Pagnoni, U. M.; Riva, S.; Forti, L. Adv. Synth. Catal. 2007, 349, 1497.

[9] Nicdotra, S.; Cramarossa, M. R.; Mucci, A.; Pagnoni, U. M.; Riva S.; Forti, L. Tetrahedron 2004, 60, 595.

[10] Sako, M.; Hosokawa, H.; Ito, T.; Iinuma M. J. Org. Chem. 2004, 69, 2598.

[11] Huo, C. H.; L, H.; Zhao, Y. Y.; Wang, B.; Zhang, Q. Y. Phytochemistry 2008, 69, 788.

[12] Braga, A. C. H.; Zacchino, S., Badano, H.; Sierra, M. G.; Ruveda, E. A. Phytochemistry 1984, 23, 2025.

[13] Wilkens, A.; Paulsen, J.; Wray, V.; Winterhalter, P. J. Agric. Food Chem. 2010, 58, 6754.

[14] Kim, H. K.; Saleem, M.; Seo, S. H.; Jin, C.; Lee, Y. S. Planta Med. 2005, 71, 973.

[15] Bu, P. B.; Li, Y. R.; Jiang, M.; Wang, X. L.; Wang, F.; Lin, S.; Zhu, C. G.; Shi, J. G. China J. Chin. Mater. Med. 2013, 38, 13 (in Chinese).

(卜鹏滨, 里艳茹, 姜明, 王晓良, 王芳, 林生, 朱承根, 石建功, 中国中药杂志, 2013, 38, 13.)

Outlines

/