Skip to main content
Log in

Membrane-active properties and antiradical activity of gossypol and its derivatives

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

A novel asymmetric gossypol derivative was synthesized. The antioxidant activity of gossypol and certain of its derivatives at the aldehyde groups and the interaction of these compounds with model membranes were studied. It was shown that the antiradical and membrane activities of the gossypol derivatives were determined by the structure of the substituent and that gossypol and its derivatives were partially localized in the lipid bilayer and possibly induced formation of a new interdigitating phase.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig.1
Fig.2
Fig.3

Similar content being viewed by others

References

  1. S. J. Segal, ed., Gossypol: A Potential Contraceptive for Men, Plenum Press, New York (1985).

    Google Scholar 

  2. K. Dodou, Expert Opin. Invest. Drugs, 14, 1419 (2005).

    Article  CAS  Google Scholar 

  3. C. M. Cater and C. M. Lyman, J. Am. Oil Chem. Soc., 64, 649 (1969).

    Article  Google Scholar 

  4. Z.-M. Guo, F. Wan, Z.-P. Gu, G.-P. Wu, and S.-X. Peng, People's Repub. China, 22, 597 (1987).

    Google Scholar 

  5. P. Przybylski, G. Bejcar, G. Schroeder, and B. Brzezinski, J. Mol. Struct., 654, 245 (2003).

    Article  CAS  Google Scholar 

  6. K. Dodou, R. J. Anderson, W. J. Lough, D. A. P. Small, M. D. Shelley, and P. W. Groundwater, Bioorg. Med. Chem., 13, 4228 (2005).

    Google Scholar 

  7. Yu. A. Vladimirov and A. I. Archakov, Peroxide Oxidation of Lipids in Biological Membranes [in Russian], Nauka, Moscow (1972).

    Google Scholar 

  8. T. Yokozawa, C. P. Chen, T. Tanaka, G.-I. Nonaka, and I. Nishioka, Biochem. Pharmacol., 56, 13 (1998).

    Article  Google Scholar 

  9. T. V. Pochinok, M. L. Tarakhovskii, V. A. Portnyagina, M. F. Denisova, V. A. Vonsyatskii, A. N. Aleksandrov, and V. A. Mel'nichuk, Khim. Farm. Zh., No. 5, 565 (1985).

  10. A. I. Glushenkova and I. P. Nazarova, Gossypol, Its Derivatives and Their Use [in Russian], Fan, Tashkent (1993).

    Google Scholar 

  11. A. L. Markman and V. P. Rzhekhin, Gossypol and Its Derivatives [in Russian], Pishchevaya Promyshlennost', Moscow (1965).

    Google Scholar 

  12. W. Droge, Physiol. Rev., 83, 47 (2001).

    Google Scholar 

  13. N. V. Gordienko, M. V. Zamaraeva, A. I. Gagel'gans, B. A. Salakhutdinov, T. F. Aripov, and A. I. Ismailov, Biol. Membr., 10, 470 (1993).

    Google Scholar 

  14. A. B. Rubin, Biophysics. Biophysics of Cellular Processes, Vysshaya Shkola, Moscow (1987).

    Google Scholar 

  15. T. J. McIntosh, R. V. McDaniel, and S. A. Simon, Biochim. Biophys. Acta. Biomembranes, 731, 109 (1983).

    Article  CAS  Google Scholar 

  16. S. A. Simon and T. J. McIntosh, Biochim. Biophys. Acta, 773, 169 (1984).

    Article  PubMed  CAS  Google Scholar 

  17. J. N. Israelachvili, S. Marcelja, and R. G. Horn, Q. Rev. Biophys., 13, 121 (1980).

    Article  PubMed  CAS  Google Scholar 

  18. M. Auger, H. C. Jarreli, I. C. P. Smith, D. J. Siminovitch, H. H. Mantsch, and P. T. T. Wong, Biochemistry, 27, 6086 (1988).

    Article  PubMed  CAS  Google Scholar 

  19. C. H. Pominski, C. Hall, R. F. Miller, and C. Boatner, J. Am. Oil. Chem. Soc., 28, 472 (1951).

    Article  CAS  Google Scholar 

  20. R. F. Miller and R. Adams, J. Am. Chem. Soc., 59, 1736 (1937).

    Article  CAS  Google Scholar 

  21. T. F. Aripov, I. A. Rosenshtein, B. A. Salakhutdinov, A. A. Lev, and V. A. Gotlib, Gen. Physiol. Biophys., 6, 343 (1987).

    PubMed  CAS  Google Scholar 

Download references

Acknowledgement

The research was performed with financial support of Project P181 of the foundation STSU/ARS USDA.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. I. Tukfatullina.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 265–266, May–June, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tukfatullina, I.I., Tilyabaev, K.Z., Mamadrakhimov, A. et al. Membrane-active properties and antiradical activity of gossypol and its derivatives. Chem Nat Compd 44, 440–445 (2008). https://doi.org/10.1007/s10600-008-9087-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-008-9087-y

Key words

Navigation