Issue

Vol. 26 No. 7 (2014): Vol 26 Issue 7

Copyright (c) 2014 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Bioactivity of Resveratrol Analogues

https://doi.org/10.14233/ajchem.2014.16226
Junli Ao
Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, P.R. China
Yuanmou Chen
Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, P.R. China
Xiaoling Xu
Shanxi Medical University Clinical Training Center, Taiyuan, Shanxi Province, P.R. China
Xu Zhang
Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, P.R. China
Yue Yu
Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, P.R. China
Peng Yu
Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, P.R. China
Erbing Hua
Key Laboratory of Industrial Microbiology of Ministry of Education, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, P.R. China

Corresponding Author(s) : Erbing Hua

huarb@tust.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 7 (2014): Vol 26 Issue 7

Abstract

It has been reported that resveratrol enhanced SIRT1 expression and significantly mimicked calorie restriction by stimulating Sir2 which is the most homologic homologue of SIRT1 of mammalian. A series of novel resveratrol derivatives were designed and synthesized as novel SIRT1 activator candidates. These synthesized compounds were characterized by spectral (1H NMR) analysis and examined for their Sir2 activation against yeast parental strain-BY4743 at a concentration of 100 μM/L by Bioscreen C MBR machine. Several compounds showed a promising Sir2 activation activity compared with resveratrol. Meanwhile, the structure-activity relationships with Sirt2 activation activities were also discussed.

Keywords

Resveratrol analogues Synthesis SIRT1 activator Wittig-horner reaction Structure-activity-relationship
Ao, J., Chen, Y., Xu, X., Zhang, X., Yu, Y., Yu, P., & Hua, E. (2014). Synthesis and Bioactivity of Resveratrol Analogues. Asian Journal of Chemistry, 26(7), 2092–2098. https://doi.org/10.14233/ajchem.2014.16226
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. J.L. Richard, Arch. Mal. Coeur Vaiss., 80, 21 (1987).
  2. M.J. Takaoka, J. Faculty Sci. Hokkaido Imperial Univ., 3, 1 (1940).
  3. R.H. Wang, K. Sengupta, C. Li, H.S. Kim, L. Cao, C. Xiao, S. Kim, X. Xu, Y. Zheng, B. Chilton, R. Jia, Z.M. Zheng, E. Appella, X.W. Wang, T. Ried and C.X. Deng, Cancer Cell, 14, 323 (2008); doi:10.1016/j.ccr.2008.09.001.
  4. H.I. Rocha-Gonzalez, M. Ambriz-Tututi and V. Granados-Soto, Resveratrol. CNS Neurosci. Ther., 14, 234 (2008); doi:10.1111/j.1755-5949.2008.00045.x.
  5. L.M. Vieira de Almeida, C.C. Piñeiro, M.C. Leite, G. Brolese, R.B. Leal, C. Gottfried and C.A. Gonçalves, Neurochem. Res., 33, 15 (2008).
  6. H.A. Ali, K. Kondo and Y. Tsuda, Chem. Pharm. Bull. (Tokyo), 40, 1130 (1992); doi:10.1248/cpb.40.1130.
  7. K. Thakkar, R.L. Geahlen and M. Cushman, J. Med. Chem., 36, 2950 (1993); doi:10.1021/jm00072a015.
  8. M. Murias, N. Handler, T. Erker, K. Pleban, G. Ecker, P. Saiko, T. Szekeres and W. Jäger, Bioorg. Med. Chem., 12, 5571 (2004); doi:10.1016/j.bmc.2004.08.008.
  9. P. Kopp, Eur. J. Endocrinol., 138, 619 (1998); doi:10.1530/eje.0.1380619.
  10. M. Jang and J.M. Pezzuto, Drugs Exp. Clin. Res., 25, 65 (1999).
  11. L.A. Stivala, M. Savio and F. Carafoli, J. Biol. Chem., 276, 22586 (2001); doi:10.1074/jbc.M101846200.
  12. F. Daroch, M. Hoeneisen and C.L. Gonzalez, Microbios, 104, 85 (2001).
  13. W.B. Wang, H.C. Lai, P.R. Hsueh, R.Y. Chiou, S.B. Lin and S.J. Liaw, J. Med. Microbiol., 55, 1313 (2006).
  14. S.F. Zaidi, K. Ahmed, T. Yamamoto, T. Kondo, K. Usmanghani, M. Kadowaki and T. Sugiyama, Biol. Pharm. Bull., 32, 1935 (2009).
  15. H. Arichi, Y. Kimura, H. Okuda, K. Baba, M. Kozawa and S. Arichi, Chem. Pharm. Bull. (Tokyo), 30, 1766 (1982); doi:10.1248/cpb.30.1766.
  16. C.R. Pace-Asciak, S. Hahn, E.P. Diamandis, G. Soleas and D.M. Goldberg, Clin. Chim. Acta, 235, 219 (1996).
  17. C.K. Chen, M.-H. Wang and I.-J. Chen, Gen. Pharmacol., 27, 629 (1996); doi:10.1016/0306-3623(95)02089-6.
  18. R.A. Frye, Biochem. Biophys. Res. Commun., 273, 793 (2000).
  19. K.T. Howitz, K.J. Bitterman, H.Y. Cohen, D.W. Lamming, S. Lavu, J.G. Wood, R.E. Zipkin, P. Chung, A. Kisielewski, L.-L. Zhang, B. Scherer and D.A. Sinclair, Nature, 425, 191 (2003); doi:10.1038/nature01960.
  20. K.J. Bitterman, O. Medvedik and D.A. Sinclair, Microbiol. Mol. Biol. Rev., 67, 376 (2003); doi:10.1128/MMBR.67.3.376-399.2003.
  21. S.M. Jazwinski, Exp. Gerontol., 34, 1 (1999); doi:10.1016/S0531-5565(98)00053-9.
  22. M. Kaeberlein, in ed.: P.M. Conn, Longevity and Aging in the Budding Yeast. In Handbook of Models for Human Aging, Elvesier Press, Boston, pp. 109-120 (2006)..
  23. P.W. Piper, Yeast, 23, 215 (2006); doi:10.1002/yea.1354.
  24. B.K. Kennedy, N.R. Austriaco and J. Zhang, Cell, 80, 485 (1995); doi:10.1016/0092-8674(95)90499-9.
  25. M. Kaeberlein, M. McVey and L. Guarente, Genes Dev., 13, 2570 (1999); doi:10.1101/gad.13.19.2570.
  26. A.K. Bhattacharya and G. Thyagarajan, Chem. Rev., 81, 415 (1981); doi:10.1021/cr00044a004.
  27. H.J. Cristau, F. Darviche, E. Torreilles and J.-M. Fabre, Tetrahedron Lett., 39, 2103 (1998); doi:10.1016/S0040-4039(98)00061-6.
  28. T. Nagasaki, M. Ukon, S. Arimori and S. Shinkai, J. Chem. Soc., Chem. Commun., 608 (1992); doi:10.1039/C39920000608.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0