Advertisement

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
Article

Abstract

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 

Abbreviations

ARE

antioxidant responsive element

GSTP1-1

glutathione S-transferase P1-1

HBSS

Hanks’ balanced salt solution

LDL

low-density lipoproteins

ROS

reactive oxygen species

RT-PCR

reverse transcription-polymerase chain reaction

S-9

sodium 3-(4′-hydroxyphenyl)propyl sulfonate

S-10

sodium 3-(4′-methoxyphenyl)propyl sulfonate

S-13

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

S-17

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

SIN-1

morpholinosydnonimine

TBARS

thiobarbituric acid-reactive substances

tBHQ

tert-butylhydroquinone

TS-9

sodium 3-(4′-hydroxyphenyl)propyl thiosulfonate

TS-10

sodium 3-(4′-methoxyphenyl)propyl thiosulfonate

TS-13

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

TS-17

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

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Menshchikova, E. B., Zenkov, N. K., Lankin, V. Z., Bondar, I. A., Krugovykh, N. F., and Trufakin, V. A. (2006) Oxidative Stress. Prooxidants and Antioxidants [in Russian], Slovo, Moscow.Google Scholar
  2. 2.
    Zenkov, N. K., Kandalintseva, N. V., Lankin, V. Z., Menshchikova, E. B., and Prosenko, A. E. (2003) Phenolic Bioantioxidants [in Russian], Novosibirsk.Google Scholar
  3. 3.
    Arts, I. C., and Hollman, P. (2005) Am. J. Clin. Nutr., 81, 317S–325S.PubMedGoogle Scholar
  4. 4.
    Kiselova, Y., Ivanova, D., Chervenkov, T., Gerova, D., Galunska, B., and Yankova, T. (2006) Phytother. Res., 20, 961–965.PubMedCrossRefGoogle Scholar
  5. 5.
    Rahman, I., Biswas, S. K., and Kirkham, P. A. (2006) Biochem. Pharmacol., 72, 1439–1452.PubMedCrossRefGoogle Scholar
  6. 6.
    Kontogiorgis, A. C., Pontiki, A. E., and Hadjipavlou-Litina, D. (2005) Mini. Rev. Med. Chem., 5, 563–574.PubMedCrossRefGoogle Scholar
  7. 7.
    Lankin, V. Z., Tikhaze, A. K., and Belenkov, Yu. N. (2004) Kardiologiya, 44, 72–81.PubMedGoogle Scholar
  8. 8.
    Manna, S. K., Mukhopadhyay, A., and Aggarwal, B. B. (2000) J. Immunol., 164, 6509–6519.PubMedGoogle Scholar
  9. 9.
    Takabe, W., Matsukawa, N., Kodama, T., Tanaka, K., and Noguchi, N. (2006) Free Rad. Res., 40, 21–30.CrossRefGoogle Scholar
  10. 10.
    Lyakhovich, V. V., Vavilin, V. A., Zenkov, N. K., and Menshchikova, E. B. (2006) Biochemistry (Moscow), 71, 962–974.CrossRefGoogle Scholar
  11. 11.
    Prosenko, A. E., Kim, A. M., and Krysin, A. P. (1993) RF Patent No. 1162781 [in Russian].Google Scholar
  12. 12.
    Levitova, E. N. (1977) in Modern Methods in Biochemistry (Orekhovich, V. N., ed.) [in Russian], Meditsina, Moscow, pp. 248–254.Google Scholar
  13. 13.
    Lowry, O., Rosebrough, W., Farr, A., and Randall, R. (1951) J. Biol. Chem., 193, 265–275.PubMedGoogle Scholar
  14. 14.
    Yagi, K. (1976) Biochem. Med., 15, 212–216.PubMedCrossRefGoogle Scholar
  15. 15.
    Menshchikova, E. B., Zenkov, N. K., Mikichur, N. I., and Safronov, I. D. (1992) Byul. SO RAMN, 12, 112–117.Google Scholar
  16. 16.
    Van Dyke, K., Sacks, M., and Qazi, N. (1998) J. Biolum. Chemilum., 13, 339–348.CrossRefGoogle Scholar
  17. 17.
    Zenkov, N. K., Menshchikova, E. B., and Shergin, S. M. (1990) Lab. Delo, 12, 33–35.PubMedGoogle Scholar
  18. 18.
    Chattopadhyay, N., Kher, R., and Godbole, M. (1993) Biotechniques, 15, 24–26.PubMedGoogle Scholar
  19. 19.
    Salvemini, D., Wang, Z. Q., Wyatt, P. S., Bourdon, D. M., Marino, M. H., Manning, P. T., and Currie, M. G. (1996) Br. J. Pharmacol., 118, 829–838.PubMedGoogle Scholar
  20. 20.
    Zhang, Y., Gonzalez, V., and Xu, M. J. (2002) J. Dermatol. Sci., 30, 205–214.PubMedCrossRefGoogle Scholar
  21. 21.
    Lee, K. W., and Lee, H. J. (2006) Biofactors, 26, 105–121.PubMedGoogle Scholar
  22. 22.
    Soobrattee, M. A., Neergheen, V. S., Luximon-Ramma, A., Aruoma, O. I., and Bahorun, T. (2005) Mutat. Res., 579, 200–213.PubMedGoogle Scholar
  23. 23.
    Shimizu, M., and Weinstein, I. B. (2005) Mutat. Res., 591, 147–160.PubMedGoogle Scholar

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

Personalised recommendations