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Protective effect of estrogens and catecholestrogens against peroxidative membrane damagein vitro

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Lipids

Abstract

The antioxidant effects of natural estrogens (estrone E1; 17β-estradiol), synthetic estrogens (17α-ethynylestradiol, EE2; mestranol, MES; diethylstilbestrol, DES) and catechle-strogens (2-hydroxyestradiol; 4-hydroxyestradiol 4-OHE2) on lipid peroxidation induced by different means in rat liver microsomes were investigated. The extent of lipid peroxidation was determined by measuring thiobarbituric acid reactive substances. Prooxidants included Fe3+/ADP/reduced NADPH, Fe2+/ascorbate,tert-butyl hydroperoxide (t-BOOH) and 2,2′-azobis (2-amidinopropane) (AAPH). Estrogens and catecholestrogens decreased lipid peroxidation in all four systems tested. In the iron/ascorbate model it was shown that (i)-OHE2 and DES had analogous patterns of inhibition, irrespective of the presence of NADPH or the functional integrity of the microsómes, and (ii) the antioxidant activities of E1, EE2 and MES were dependent on the assay conditions with the activity being markedley higher when estrogen metabolism was favored. When peroxidation was initiated by the peroxyl radical generator AAPH, the inhibitory effects observed were least pronounced. Our data also showed that, in each of the systems, all inhibitors displayed the same order of inhibitory potency with DES and catecholestrogens being the most potent antioxidants under all experimental conditions used. The present results confirm earlier findings and point toward a link between estrogen metabolism and estrogen antioxidant activity. The data also indicate that estrogens and catecholestrogens interact with the peroxidative process at different levels with their interactions with iron or the metal-derived species being the most important modes of inhibition.

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Abbreviations

AAPH:

2,2′-azobis(2-amidinopropane)

DES:

diethylstilbestrol

DMSO:

dimethylsulfoxide

E1 :

estrone

E2 :

17β-estradiol

EE2 :

17α-ethynylestradiol

IC50 :

half inhibitory concentration

MDA:

malondialdehyde

MES:

mestranol

2-OHE2 :

2-hydroxyestradiol

4-OHE2 :

4-hydroxyestradiol

TBA:

thiobarbituric acid

TBARS:

thiobarbituric acid reactive substances

TCA:

trichloroacetic acid

t-BOOH:

tert-butyl hydroperoxide

References

  1. Haaf, H., Li, S.A., and Li, J.J. (1987)Carcinogenesis 8, 209–215.

    PubMed  CAS  Google Scholar 

  2. Lamartiniere, C.A., and Pardo, G.A. (1988)J. Biochem. Toxicol. 3, 87–103.

    Article  PubMed  CAS  Google Scholar 

  3. Morgan, P., Maggs, J.L., Bulman-Page, P.C., Hussain, F., and Park, B.K. (1992)Biochem. Pharmacol. 43, 985–994.

    Article  PubMed  CAS  Google Scholar 

  4. Lax, E.R. (1987)J. Steroid Biochem. 27, 1119–1128.

    Article  PubMed  CAS  Google Scholar 

  5. Liehr, J.G., and Roy, D. (1990)Free Rad. Biol. Med. 8, 415–423.

    Article  PubMed  CAS  Google Scholar 

  6. Cho, B.H., Smith, T.L., Park, J.R., and Kummerow, F.A. (1988)Lipids 23, 853–856.

    Article  PubMed  CAS  Google Scholar 

  7. Roy, D., and Liehr, J.G. (1989)Cancer Res. 49, 1475–1480.

    PubMed  CAS  Google Scholar 

  8. Yagi, K., and Komura, S. (1986)Biochem. Inst. 13, 1051–1055.

    CAS  Google Scholar 

  9. Sugioka, K., Shimosegawa, Y., and Nakano, M. (1987)FEBS Lett. 210, 37–39.

    Article  PubMed  CAS  Google Scholar 

  10. Nakano, M., Sugioka, K., Naito, I., Takekoshi, S., and Niki, I. (1987)Biochem. Biophys. Res. Commun. 142, 919–924.

    Article  PubMed  CAS  Google Scholar 

  11. Mooradian, A.D. (1993)J. Steroid Biochem. Molec. Biol. 45, 509–511.

    Article  PubMed  CAS  Google Scholar 

  12. Ruiz-Larrea, M.B., Garrido, M.J., and Lacort, M. (1993)J. Biochem. 113, 563–567.

    PubMed  CAS  Google Scholar 

  13. Ruiz-Larrea, M.B., Leal, A.M., Liza, M., Lacort, M., and de Groot, H. (1994)Steroids 59, 383–388.

    Article  PubMed  CAS  Google Scholar 

  14. Martinez, M.J., Ruiz, J.I., Lacort, M., and Ochoa, B. (1991)Biochim. Biophys. Acta 1085, 106–111.

    PubMed  CAS  Google Scholar 

  15. Bradford, M.N. (1976)Anal. Biochem. 72, 248–254.

    Article  PubMed  CAS  Google Scholar 

  16. Fee, J.A., and Teitelbaum, H.D. (1972)Biochem. Biophys. Res. Commun. 49, 150–158.

    Article  PubMed  CAS  Google Scholar 

  17. Afanasév, I.B., Dorozhko, A.I., Brodskii, A.V., Kostyuk, V.A., and Potapovitch, A.I. (1988)Biochem. Pharmacol. 38, 1763–1769.

    Article  Google Scholar 

  18. Pulla Reddy, A.Ch., and Lokesh, B.R. (1992)Mol. Cell. Biochem. 111, 117–124.

    Article  Google Scholar 

  19. Weglicki, W.B., and Mak, I.T. (1992)Mol. Cell. Biochem. 118, 105–111.

    Article  PubMed  CAS  Google Scholar 

  20. Liu, G., Zhang, T., Wang, B., and Wang, Y. (1992)Biochem. Pharmacol. 43, 147–152.

    Article  PubMed  CAS  Google Scholar 

  21. Halliwell, B., and Gutteridge, J.M.C. (eds.) (1989)Free Radicals in Biology and Medicine, 2nd edn., pp. 188–276, Clarendon Press, oxford.

    Google Scholar 

  22. Puntarulo, S., and Cederbaum, A.I. (1988)Arch. Biochem. Biophys. 264, 482–491.

    Article  PubMed  CAS  Google Scholar 

  23. Samokyszyn, V.M., Miller, D.M., Reif, D.W., and Aust, S.D. (1989) inMembrane Lipid Oxidation (Vigo-Pelfrey, C., ed.) Vol. I, pp. 101–129, CRC Press, Boca Raton.

    Google Scholar 

  24. Minotti, G., and Aust, S.D. (1987)Chem. Phys. Lipids 44, 191–208.

    Article  PubMed  CAS  Google Scholar 

  25. Scheschonka, A., Murphy, M.E., and Sies, H. (1990)Chem. Biol. Interactions 74, 233–252.

    Article  CAS  Google Scholar 

  26. Yamamoto, Y., Haga, S., Niki, E., and Kamiya, Y. (1984)Bull. Chem. Soc. Japan. 59, 1260–1264.

    Article  Google Scholar 

  27. Barclay, L.R.C., Locke, S.J., aacNeil, J.M., and VanKessel, J. (1984)J. Am. Chem. Soc. 106, 2479–2481.

    Article  CAS  Google Scholar 

  28. Cadenas, E., and Sies, H. (1982)Eur. J. Biochem. 124, 349–356.

    Article  PubMed  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. Departmento de Fisiología, Facultad de Medicina, Universidad del Pais Vasco, P.O. Box 699, Bilbao, Spain

    Mercedes Lacort, Ana M. Leal, Mariana Liza, César Martín, Rosa Martínez & M. Begoña Ruiz-Larrea

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  1. Mercedes Lacort
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  2. Ana M. Leal
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  3. Mariana Liza
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  4. César Martín
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  5. Rosa Martínez
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  6. M. Begoña Ruiz-Larrea
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Lacort, M., Leal, A.M., Liza, M. et al. Protective effect of estrogens and catecholestrogens against peroxidative membrane damagein vitro . Lipids 30, 141–146 (1995). https://doi.org/10.1007/BF02538267

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  • DOI: https://doi.org/10.1007/BF02538267

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