Biochemistry (Moscow)

, Volume 72, Issue 6, pp 644–651 | Cite as

Antioxidant and antiinflammatory activity of new water-soluble sulfur-containing phenolic compounds

  • N. K. Zenkov
  • E. B. Menshchikova
  • N. V. Kandalintseva
  • A. S. Oleynik
  • A. E. Prosenko
  • O. N. Gusachenko
  • O. A. Shklyaeva
  • V. A. Vavilin
  • V. V. Lyakhovich


We synthesized a series of structurally related water-soluble alkyl phenols — sodium 4-hydroxyphenyl propyl sulfonates and thiosulfonates with different number of tert-butyl groups at the ortho-position. In experimental systems of transient metal-induced ethyl oleate and low-density lipoprotein oxidation the antioxidant activity of the compounds increased when the tert-butyl group number at the ortho-position increased and when the sulfonate group was replaced with thiosulfonate. Compounds containing thiosulfonate group in para-propyl substituent also more effectively inhibited reactive oxygen metabolites generated in xanthine-xanthine oxidase system and during morpholinosydnonimine decomposition compared to sulfonate-containing analogs. Phenols with one tert-butyl group at the ortho-position have been shown to exhibit the highest antiinflammatory activity in the model of carrageenan-induced rat paw inflammation, as well as with regard to the expression of the glutathione S-transferase P1-1 gene in HepG2 human hepatoma cell line. Thus, it can be reasonably speculated that the antiinflammatory activity of sulfur-containing phenolic antioxidants in vivo is mediated by their effect on redox-sensitive transcription factors.

Key words

oxidative stress phenolic antioxidants antioxidant responsive element 



antioxidant responsive element


glutathione S-transferase P1-1


Hanks’ balanced salt solution


low-density lipoproteins


reactive oxygen species


reverse transcription-polymerase chain reaction


sodium 3-(4′-hydroxyphenyl)propyl sulfonate


sodium 3-(4′-methoxyphenyl)propyl sulfonate


sodium 3-(3′-tert-butyl-4′-hydroxyphenyl)propyl sulfonate


sodium 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propyl sulfonate




thiobarbituric acid-reactive substances




sodium 3-(4′-hydroxyphenyl)propyl thiosulfonate


sodium 3-(4′-methoxyphenyl)propyl thiosulfonate


sodium 3-(3′-tert-butyl-4′-hydroxyphen-yl)propyl thiosulfonate


sodium 3-(3′,5′-di-tert-butyl-4′-hydroxyphenyl)propyl thiosulfonate


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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • N. K. Zenkov
    • 1
  • E. B. Menshchikova
    • 1
  • N. V. Kandalintseva
    • 2
  • A. S. Oleynik
    • 2
  • A. E. Prosenko
    • 2
  • O. N. Gusachenko
    • 3
  • O. A. Shklyaeva
    • 3
  • V. A. Vavilin
    • 4
  • V. V. Lyakhovich
    • 4
  1. 1.Scientific Center of Clinical and Experimental MedicineSiberian Branch of the Russian Academy of Medical SciencesNovosibirskRussia
  2. 2.Novosibirsk State Pedagogical UniversityNovosibirskRussia
  3. 3.Institute of Chemical Biology and Fundamental MedicineSiberian Branch of the Russian Academy of SciencesNovosibirskRussia
  4. 4.Institute of Molecular Biology and BiophysicsSiberian Branch of the Russian Academy of Medical SciencesNovosibirskRussia

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