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Pro- and antioxidant characteristics of natural thiols

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Abstract

In aqueous solutions at physiological temperature, the mechanism of antioxidative action of natural thiols (glutathione, cysteine, and homocysteine) mainly involves reactions with reactive oxygen species (ROS), peroxyl radicals and hydrogen peroxide. Reduction of hydrogen peroxide by thiols is accompanied by radical generation. The kinetic characteristics of these processes, including those for the reactions of hydrogen peroxide and glutathione immobilized on solid supports such as sodium montmorillonite (clay) and cellulose were determined. Prooxidative effects of thiols are related with the reactions of thiyl radicals formed in the exchange reactions of thiols with other radicals and in the reactions between thiols and hydroperoxides. Thiyl radicals are known to react easily with double bonds. Resveratrol and caffeic acid, phenolic antioxidants containing double bond in their molecules, were shown to be consumed when reacted with glutathione and the process accelerated in the presence of hydrogen peroxide.

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References

  1. H. Sies, in Oxidative Stress, Ed. H. Sies, Academic Press, London, 1985, 507 pp.

  2. H. Sies, D. P. Jones, in Encyclopedia of Stress, Ed. G. Fink, Vol. 3, Elsevier, San Diego, 2007, p.45.

  3. S. Reuter, S. C. Gupta, M. M. Chaturvedi, B. B. Aggarwal, Free Radic. Biol. Med., 2010, 49, 1603.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. O. I. Aruoma, J. Am. Oil Chem. Soc., 1998, 75,199.

    Article  CAS  Google Scholar 

  5. W. Sajevicz, M. Zalewska, H. Milnerowicz, Toxicol. in Vitro, 2015, 29,149.

    Google Scholar 

  6. B. G. Hill, A. Bhatnagar, IUBMB Life, 2007, 59,21.

    Article  CAS  PubMed  Google Scholar 

  7. B. G. Harbrecht, M. Di Silvio, V. Chough, Y. M. Kim, R. L. Simmons, T. R. Billiar, Ann. Surg., 1997, 225,76.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Y. Wang, M. Qiao, J. J. Mieyal, L. M. Asmis, R. Asmis, Free Rad. Biol. Med., 2006, 41,775.

    Article  CAS  PubMed  Google Scholar 

  9. C. S. Sevier, C. A. Kaiser, Nat. Rev. Mol. Cell Biol., 2002, 3,836.

    Article  CAS  PubMed  Google Scholar 

  10. A. C. Burtis, E. R. Ashwood, W. B. Saunders, Tietz Fundament als of Clinical Chemistry, Elsevier, Philadelphia, 1996.

    Google Scholar 

  11. P. White, S. Threlfell, G. Hignett, A. Wain, N. Lawrence, J. Davis, R. Compton, Analyst, 2002, 127,797.

    Article  CAS  PubMed  Google Scholar 

  12. H. Refsum, A. Smith, P. Ueland, E. Nexo, R. Clarke, J. McPartlin, C. C. Johnston, F. Engbaek, J. Schneede, C. McPartlin, J. Scott, Clin. Chem., 2004, 50,3.

    Article  CAS  PubMed  Google Scholar 

  13. N. Lawrence, R. Deo, J. Wang, Talanta, 2004, 63,443.

    Article  CAS  PubMed  Google Scholar 

  14. H. Refsum, P. Ueland, O. Nygård, S. Vollset, Ann. Rev. Med., 1998, 49,31.

    Article  CAS  PubMed  Google Scholar 

  15. M. S. Elgawish, N. Kishikawab, N. Kurodab, Analyst, 2015, 140, 8148.

    Article  CAS  PubMed  Google Scholar 

  16. F. Ursini, A. Bindoli. Chem. Phys. Lipids, 1987, 44,255.

    Article  CAS  PubMed  Google Scholar 

  17. R. Brigelius-Flohe, Free Radic. Biol. Med., 1999, 27,951.

    Article  CAS  PubMed  Google Scholar 

  18. K. Socha, J. Kochanowicz, E. Karpinska, J. Soroczynska, M. Jako niuk, Z. Mariak, M. H. Borawska, Nutrition J., 2014, 13,62.

    Article  CAS  Google Scholar 

  19. S. Sonthalia, D. Daulatabad, R. Sarkar, Indian J. Dermatol. Venereol. Leprol., 2016, 82,262.

    Article  PubMed  Google Scholar 

  20. E. Y. Park, N. Shimura, T. Konishi, Y. Sauchi, S. Wada, W. Aoi, J. Agric. Food Chem., 2014, 62, 6183.

    Article  CAS  PubMed  Google Scholar 

  21. F. Watanabe, E. Hashizume, G. P. Chan, A. Kamimura, Clin. Cosmet. Investig. Dermatol., 2014, 7,267.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Y. Shindo, T. Hashimoto, Arch. Dermatol. Res., 1995, 287,747.

    Article  CAS  PubMed  Google Scholar 

  23. E. A. Mengele, D. A. Krugovov, O. T. Kasaikina, Russ. Chem. Bull. (Int. Ed.), 2015, 64,846.

    Article  CAS  Google Scholar 

  24. C. Chatgilialoglu, C. Ferreri, Acc. Chem. Res., 2005, 38,441.

    Article  CAS  PubMed  Google Scholar 

  25. C. Ferreri, C. Costantino, L. Landi, Q. G. Mulazzani, C. Chatgilialoglu, Chem. Commun., 1999,407.

    Google Scholar 

  26. A. Samadi, I. Andreu, C. Ferreri, S. Dellonte, C. Chatgilialoglu, J. Am. Oil Chem. Soc., 2004, 81,753.

    Article  CAS  Google Scholar 

  27. K. M. Zinatullina, O. T. Kasaikina, V. A. Kuzmin, N. P. Khrameeva, B. I. Shapiro, Russ. Chem. Bull. (Int. Ed.), 2016, 65, 2825.

    Article  CAS  Google Scholar 

  28. K. M. Zinatullina, O. T. Kasaikina, V. A. Kuzmin, N. P. Khrameeva, B. I. Shapiro, Russ. Chem. Bull. (Int. Ed.), 2017, 66, 1300.

    Article  CAS  Google Scholar 

  29. K. M. Zinatullina, N. P. Khrameeva, O. T. Kasaikina, B. I. Shapiro, V. A. Kuzmin, Russ. Chem. Bull. (Int. Ed.), 2017, 66, 2145.

    Article  CAS  Google Scholar 

  30. M. R. Olthof, P. C. Hollman, M. B. Katan, J. Nutr., 2001, 131,66.

    Article  CAS  PubMed  Google Scholar 

  31. N. Rajendra Prasad, A. Karthikeyan, S. Karthikeyan, B. V. Reddy, Mol. Cell Biochem., 2011, 349,11.

    Article  CAS  PubMed  Google Scholar 

  32. C. Magnani, V. L. B. Isaac, M. A. Corrêa, H. R. N. Salgado, Anal. Methods, 2014, 6, 3203.

    Article  CAS  Google Scholar 

  33. G. L. Ellman. Arch. Biochem. Biophys., 1959, 82,70.

    Article  CAS  PubMed  Google Scholar 

  34. C. D. Pereira, N. Minamino, T. Takao, Anal. Chem., 2015, 87, 10785.

    Article  CAS  PubMed  Google Scholar 

  35. C. K. Riener, G. Kada, H. J. Gruber, Anal. Bioanal. Chem., 2002, 373, 266; DOI:10.1007/s00216-002-1347-2.

    Article  CAS  PubMed  Google Scholar 

  36. A. A. Yakovleva, N. V. Gulyaeva, Biomedetsinskaya khimiya [Biomedical Chemistry], 2004, 50, No. 4, 390 (in Russian).

    Google Scholar 

  37. Pat. RF: 2515319, Bull. Izobret. [Invention Bulletin], 2014, No. 13 (in Russian).

  38. O. T. Kasaikina, Catal. Sustain. Energy, 2014, 1, 21.

    Google Scholar 

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Correspondence to K. M. Zinatullina.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0726–0730, April, 2018.

Based on the materials of the III Interdisciplinary Symposium on Medicinal, Organic, and Biological Chemistry and Pharmaceuticals (MOBI-ChemPharma-2017; May 28–31, 2017; Sevastopol, Russia).

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Zinatullina, K.M., Kasaikina, O.T., Kuzmin, V.A. et al. Pro- and antioxidant characteristics of natural thiols. Russ Chem Bull 67, 726–730 (2018). https://doi.org/10.1007/s11172-018-2129-0

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  • DOI: https://doi.org/10.1007/s11172-018-2129-0

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