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Kinetic characteristics of the reaction of resveratrol with peroxyl radicals and natural thiols in aqueous medium

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Abstract

The method of competing reactions was used to determine the rate constants of the reaction of resveratrol (RVT) with peroxyl radicals formed on decomposition of the azoinitiator ААРН in aqueous solutions at 37 °С. The polymethine dye A (3,3′-di-γ-sulfopropyl-9-metylthiacarbocyanine-betaine pyridinium salt) was used as a competing acceptor of radicals. It was found that resveratrol can be involved in the reaction with natural thiols, glutathione (GSH) and cysteine (CSH), in aqueous solutions at 37 °С. The reaction of RVT with thiols (thiol—еne reaction) follows a chain mechanism and accelerates in the presence of Н2О2. The results obtained can be useful for understanding the physiological role of thiols in oxidation processes.

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References

  1. P. Langcake, R. J. Pryce, Physiology and Plant Pathology, 1976, 9, 77.

    Article  CAS  Google Scholar 

  2. L. Frémont, Life Sci., 2000, 66, 663.

    Article  Google Scholar 

  3. S. Renaud, M. de Lorgeril, Lancet, 1992, 339, 1523.

    Article  CAS  Google Scholar 

  4. M. Jang, L. Cai, G. O. Udeani, K. V. Slowing, C. E. Tho-mas, C. W. Beecher, H. H. Fong, N. R. Farnsworth, A. D. Kinghorn, R. G. Mehta, R. C. Moon, J. M. Pezzuto, Science, 1997, 275, 218.

    Article  CAS  Google Scholar 

  5. C. R. Pace-Asciak, S. Hahn, E. P. Diamandis, G. Soleas, D. M. Goldberg, Clin. Chim. Acta, 1995, 235, 207.

    Article  CAS  Google Scholar 

  6. A. A. E. Bertelli, L. Giovannini, D. Gianessi, M. Migliori, W. Bernini, M. Fregoni, A. Bertelli, Int. J. Tiss. Reac., 1995, 17, 1.

    CAS  Google Scholar 

  7. D. K. Das, M. Sato, P. S. Ray, G. Maulik, R. M. Engelman, A. A. E. Bertelli, A. Bertelli, Drugs Exp. Clin. Res., 1999, 25, 115.

    CAS  Google Scholar 

  8. J. C. Ruf, Drugs Exp. Clin. Res., 1999, 25, 125.

    CAS  Google Scholar 

  9. Z. Meng, H. Jing, L. Gan, H. Li, B. Luo, Am. J. Transl. Res., 2016, 8, 2641.

    CAS  Google Scholar 

  10. B. N. Zordoky, I. M. Robertson, J. R. Dyck, Biochim. Bio-phys. Acta, 2015, 1852, 1155.

    Article  CAS  Google Scholar 

  11. L. Belguendouz, L. Fremont, M. T. Gozzelino, Biochem. Pharmacol., 1998, 55, 811.

    Article  CAS  Google Scholar 

  12. A. Plauth, A. Geikowski, S. Cichon, S. J. Wowro, L. Lied-gens, M. Rousseau, C. Weidner, L. Fuhr, M. Kliem, G. Jenkins, S. Lotito, L. J. Wainwright, S. Sauer, Free Rad. Biol. Med., DOI: 10.1016/j.freeradbiomed.2016.08.006.

    Google Scholar 

  13. B. Olas, P. Nowak, J. Kolodziejczyk, M. Ponczek, B. Wa-chowicz, J. Nutr. Biochem., 2006, 17, 96.

    Article  CAS  Google Scholar 

  14. B. Tadolini, C. Juliano, L. Piu, F. Franconi, L. Cabrini, Free Rad. Res., 2000, 33, 105.

    Article  CAS  Google Scholar 

  15. Y. J. Cai, J. G. Fang, L. P. Ma, L. Yang, Z. L. Liu, Biochim. Biophys. Acta, 2003, 1637, 31.

    Article  CAS  Google Scholar 

  16. L. Frémont, L. Belguendouz, S. Delpal, Life Sci., 1999, 64, 2511.

    Article  Google Scholar 

  17. P. Brito, L. M. Almeida, T. C. Dinis, Free Rad. Res., 2002, 36, 621.

    Article  CAS  Google Scholar 

  18. D. Pietraforte, L. Turco, E. Azzini, M. Minetti, Biochim. Biophys. Acta, 2002, 1583, 176.

    Article  CAS  Google Scholar 

  19. H. Berrougui, G. Grenier, S. Loued, G. Drouin, A. Khalil, Atherosclerosis, 2009, 207, 420.

    Article  CAS  Google Scholar 

  20. B. Fauconneau, P. Waffo-Teguo, F. Huguet, L. Barrier, A. Decendit, J.-M. Merillon, Life Sci., 1997, 61, 2103.

    Article  CAS  Google Scholar 

  21. D. G. Soares, A. C. Andreazza, M. Salvador, J. Agric. Food Chem., 2003, 51, 1077.

    Article  CAS  Google Scholar 

  22. E. T. Denisov, T. G. Denisova, Handbook of Antioxidants, CRC Press, Boca Raton, 2000.

    Google Scholar 

  23. J.-G. Fang, M. Lu, Z.-H. Chen, H.-H. Zhu, Y. Li, L.Yang, L.-M Wu, Z.-L. Liu, Chem. Eur. J., 2002, 8, 4191.

    Article  CAS  Google Scholar 

  24. A. M. Alonso, C. Domínguez, D. A. Guille′n, C. G. Barroso, J. Agric. Food. Chem., 2002, 50, 3112.

    Article  CAS  Google Scholar 

  25. A. Amorati, F. Ferroni, G. F. Pedulli, L. Valgimigli, J. Org. Chem., 2003, 68, 9654.

    Article  CAS  Google Scholar 

  26. R. Amorati, M. Lucarini, V. Mugnaini, G. Franco Pedulli, J. Org. Chem., 2004, 69, 7101.

    Article  CAS  Google Scholar 

  27. L. Camont, F. Collin, M. Couturier, P. Thérond, D. Jore, M. Gardès-Albert, D. Bonnefont-Rousselot, Biochimie, 2012, 94, 741.

    Article  CAS  Google Scholar 

  28. L. Camont, C. H. Cottart, Y. Rhayema, V. Nivet-Antoinea, R. Djelidi, F. Collin, J. L. Beaudeuxa, D. Bonnefont-Rous-selot, Anal. Chim. Acta, 2009, 634, 121.

    Article  CAS  Google Scholar 

  29. Y. Rhayem, P. Therond, L. Camont, M. Couturier, J.-L. Beaudeux, A. Legrand, D. Jore, M. Gardes-Albert, D. Bon-nefont-Rousselot, Chem. Phys. Lipids, 2008, 155, 48.

    Article  CAS  Google Scholar 

  30. S. Stojanovic, О. Brede, Phys. Chem. Chem. Phys., 2002, 4, 757.

    Article  CAS  Google Scholar 

  31. L.-Y. Jiang, S. He, K.-Z. Jiang, C.-R. Sun, Y.-J. Pan, J. Agric. Food Chem., 2010, 58, 9020. DOI:10.1021/jf102005z.

    Article  CAS  Google Scholar 

  32. D. D. Li, R. M. Han, R. Liang, C. H. Chen, W. Lai, J. P. Zhang, L. H. Skibsted, J. Phys. Chem. B, 2012, 116, 7154.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  35. A. Samadi, I. Andreu, C. Ferreri, S. Dellonte, C. Chatgilia-loglu, J. Am. Oil Chem. Soc., 2004, 81, 753.

    Article  CAS  Google Scholar 

  36. R. K. Rolston, G. Perry, X. Zhu, R. J. Castellani, B. E. Dwyer, H. Lee, R. B. Petersen, M. A. Smith, Agro Food Ind. Hi Tech., 2009, 19, 33.

    Google Scholar 

  37. B. Halliwell, J. C. Gutteridge, Free Rad. Biol. Med., 1995, 18, 125.

    Article  CAS  Google Scholar 

  38. I. S. Young, J. V. Woodside, J. Clin. Pathol., 2001, 54, 176.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  40. K. M. Zinatullina, O. T. Kasaikina, V. A. Kuzmin, N. P. Khrameeva, B. I. Shapiro, Russ. Chem. Bull., 2017, 66, 1300.

    Article  CAS  Google Scholar 

  41. K. M. Zinatullina, O. T. Kasaikina, V. A. Kuzmin, N. P. Khrameeva, B. I. Shapiro, Russ. Chem. Bull., 2016, 65, 282].

    Article  Google Scholar 

  42. E. T. Denisov, I. F. Afanasév, Oxidation and Antioxidants in Organic Chemistry and Biology, CRC Press Taylor & Francis Group, London—New York—Singapore, 2005.

    Book  Google Scholar 

  43. V. A. Roginsky, Fenoínyye antioksidanty: reaktsionnaya sposobnost′ i effektivnost′ [Phenolic Antioxidants: Reactivity and Efficiency], Nauka, Moscow, 1988, 247 pp. (in Russian).

    Google Scholar 

  44. V. A. Roginsky, Arch. Biochem. Biophys., 2003, 414, 261.

    Article  CAS  Google Scholar 

  45. B. Frei, R. Stocker, B. N. Ames, Proc. Natl. Acad. Sci. USA, 1988, 85, 9748.

    Article  CAS  Google Scholar 

  46. C. E. Hoyle, C. N. Bowman, Angew. Chem., Int. Ed., 2010, 49, 1540.

    Article  CAS  Google Scholar 

  47. M. J. Kade, D. J. Burke, C. J. Hawker, J. Polymer Sci. Part A: Polymer Chem., 2010, 48, 743.

    Article  CAS  Google Scholar 

  48. O. Turunk, M. A. R. Meier, Macromol. Rapid Commun., 2010, 31, 1822.

    Article  Google Scholar 

  49. U. Biermann, W. Butte, R. Koch, P. A. Fokou, O. Turunk, M. A. R. Meier, J. O. Metzger, Eur. J. Lipid Sci. Technol., 2012, 18, 8201.

    CAS  Google Scholar 

  50. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed., 2001, 40, 2004.

    Article  CAS  Google Scholar 

  51. E. A. Mengele, D. A. Krugovov, O. T. Kasaikina, Russ. Chem. Bull., 2015, 64, 846.

    Article  CAS  Google Scholar 

  52. K. M. Zinatullina, N. P. Khrameeva, E. A. Mengele, O. T. Kasaikina, V. A. Kuzmin, 1st Int. Symp. on Lipid Oxidation and Antioxidants, Book of Abstracts, Porto, Portugal, 2016, 17; http://www.eurofedlipid.org/meetings/porto2016/t.

    Google Scholar 

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Authors and Affiliations

  1. N. N. Semenov Institute of Chemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    K. M. Zinatullina & O. T. Kasaikina

  2. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    K. M. Zinatullina, N. P. Khrameeva, B. I. Shapiro & V. A. Kuzmin

  3. P. G. Demidov Yaroslavl State University, 14 ul. Sovetskaya, 150000, Yaroslavl, Russian Federation

    K. M. Zinatullina & O. T. Kasaikina

  4. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    O. T. Kasaikina & V. A. Kuzmin

Authors
  1. K. M. Zinatullina
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  2. N. P. Khrameeva
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  3. O. T. Kasaikina
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  4. B. I. Shapiro
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Correspondence to K. M. Zinatullina.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2145—2151, November, 2017.

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Zinatullina, K.M., Khrameeva, N.P., Kasaikina, O.T. et al. Kinetic characteristics of the reaction of resveratrol with peroxyl radicals and natural thiols in aqueous medium. Russ Chem Bull 66, 2145–2151 (2017). https://doi.org/10.1007/s11172-017-1995-1

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  • DOI: https://doi.org/10.1007/s11172-017-1995-1

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