Antioxidant and Antiinflammatory Activity of New Water-Soluble Sulfur-Containing Phenolic Compounds

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N. K. Zenkov¹, E. B. Menshchikova^1*, N. V. Kandalintseva², A. S. Oleynik², A. E. Prosenko², O. N. Gusachenko³, O. A. Shklyaeva³, V. A. Vavilin⁴, and V. V. Lyakhovich⁴

¹Scientific Center of Clinical and Experimental Medicine, Siberian Branch of the Russian Academy of Medical Sciences, ul. Timakova 2, 630117 Novosibirsk, Russia; fax: (383) 333-6456; E-mail: lemen@soramn.ru

²Novosibirsk State Pedagogical University, ul. Vilyuiskaya 28, 630126 Novosibirsk, Russia; fax: (383) 268-1856; E-mail: chemistry@ngs.ru

³Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences, ul. Lavrentieva 8, 630090 Novosibirsk, Russia; fax: (383) 333-3677; E-mail: niboch@niboch.nsc.ru

⁴Institute of Molecular Biology and Biophysics, Siberian Branch of the Russian Academy of Medical Sciences, ul. Timakova 2, 630117 Novosibirsk, Russia; fax: (383) 332-3147; E-mail: lyakh@soramn.ru

^* To whom correspondence should be addressed.

Received January 31, 2007

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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.

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KEY WORDS: oxidative stress, phenolic antioxidants, antioxidant responsive element

DOI: 10.1134/S0006297907060077

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