Inactivation of creatine kinase induced by quercetin with horseradish peroxidase and hydrogen peroxide: Pro-oxidative and anti-oxidative actions of quercetin

Food and Chemical Toxicology

Volumn 41, Issue 6, 2003, Pages 759-765

  Miura, T ^a   Muraoka, S ^a   Fujimoto, Y ^a  

^a HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Anti oxidant; Creatine kinase; Flavonoid; Pro oxidant; Quercetin; Quercetin radical; Sulfhydryl enzyme

Indexed keywords

ADENOSINE DIPHOSPHATE; CATECHIN; CATECHOL; CREATINE KINASE; CREATINE PHOSPHATE; FLAVONOID; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; IRON; KAEMPFEROL; LIPID; LUTEOLIN; QUERCETIN; RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; STABILIZING AGENT; TAXIFOLIN; THIOL GROUP; TRYPTOPHAN; ZINC ION;

ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; COMPARATIVE STUDY; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG MECHANISM; DRUG SENSITIVITY; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME CONFORMATION; ENZYME INACTIVATION; ENZYME INHIBITION; HEART; HOMOGENATE; KINETICS; LIPID PEROXIDATION; LIVER MICROSOME; MALE; MOLECULAR INTERACTION; NONHUMAN; OXIDATION; PROTEIN PROTEIN INTERACTION; RAT; STRUCTURE ACTIVITY RELATION;

ARMORACIA RUSTICANA;

EID: 0038064452     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0278-6915(03)00005-X     Document Type: Article

References (32)

1. Awad H.M., Boersma M.G., Vervoort J., Rietjens I.M. Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts. Archives of Biochemistry and Biophysics. 378:2000;224-233.
2. Bonnichsen R.K., Brink G. Alcohol dehydrogenase. Methods in Enzymology. 1:1955;495-496.
3. Bors W., Heller W., Michel C. The chemistry of flavonoids. Rice-Evans C.A., Packer L. Flavonoids in Health and Disease. 1997;111-136 Marcel Dekker, New York.
4. Bors W., Michel C., Saran M. Flavonoid antioxidants. rate constants for reactions with oxygen radicals Methods in Enzymology. 234:1994;420-429.
5. Buege J.A., Aust S.D. Microsomal lipid peroxidation. Methods in Enzymology. 52:1978;302-310.
6. Cao G., Sofic E., Prior R.L. Antioxidant and prooxidant behavior of flavonoids. structure-activity relationships Free Radical Biology and Medicine. 22:1997;749-760.
7. Cotelle N., Bernier J.L., Catteau J.P., Pommery J., Wallet J.C., Gaydou E.M. Antioxidant properties of hydroxy-flavones. Free Radical Biology and Medicine. 20:1996;35-43.
8. Das D., Banerjee R.K. Effect of stress on the antioxidant enzymes and gastric ulceration. Molecular and Cellular Biochemistry. 125:1993;115-125.
9. Deschner E.E., Ruperto J., Wong G., Newmark H.L. Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia. Carcinogenesis. 12:1991;1193-1196.
10. Ellman G.L. Tissue sulfhydryl groups. Archives of Biochemistry and Biophysics. 82:1959;70-77.
11. Fantone J.C., Word P.A. Role of oxygen-derived free radicals and metabolites in leukocyte-dependent inflammatory reactions. American Journal of Pathology. 107:1982;397-418.
12. Ferrandiz M.L., Alcaraz M.J. Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Agents and Actions. 32:1991;283-288.
13. Gil B., Sanz M.J., Terencio M.C., Ferrandiz M.L., Bustos G., Paya M., Gunasegaran R., Alcaraz M.J. Effects of flavonoids on Naja naja and human recombinant synovial phospholipases A2 and inflammatory responses in mice. Life Sciences. 54:1994;333-338.
14. Gonzalez Flecha B.S., Repetto M., Evelson P., Boverris A. Inhibition of microsomal lipid peroxidation by α-tocopherol and α-tocopherol acetate. Xenobiotica. 21:1991;1013-1022.
15. Jovanovic S.V., Steenken S., Simic M.G. Antioxidant properties of flavonoids: reduction potentials and electron transfer reactions of flavonoid radicals. Rice-Evans C.A., Packer L. Flavonoids in Health and Disease. 1998;137-161 Marcel Dekker, New York.
16. Laughton M.J., Halliwell B., Evans P.J., Hoult J.R. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation, hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochemical Pharmacology. 38:1989;2859-2865.
17. Metodiewa D., Jaiswal A.K., Cenas N., Dickancaite E., Segura-Aguilar J. Quercetin may act as a cytotoxic prooxidant after its metabolic activation to semiquinone and quinoidal product. Free Radical Biology and Medicine. 26:1999;107-116.
18. Middleton E. Jr., Kandaswami C. Effects of flavonoids on immune and inflammatory cell functions. Biochemical Pharmacology. 43:1992;1167-1179.
19. Miura T., Muraoka S., Fujimoto Y. Effect of estrogens on the oxidative damage induced by ferrylmyoglobin. Journal of Steroid Biochemistry and Molecular Biology. 67:1998;57-62.
20. Miura T., Muraoka S., Fujimoto Y. Inactivation of creatine kinase induced by dopa and dopamine in the presence of ferrylmyoglobin. ChemicoBiological Interactions. 123:1999;51-61.
21. Miura T., Muraoka S., Fujimoto Y. Inhibition of lipid peroxidation by pindolol. Pharmacology and Toxicology. 84:1999;130-134.
22. Miura T., Muraoka S., Fujimoto Y. Phenylbutazone radicals inactivate creatine kinase. Free Radical Research. 34:2001;167-175.
23. Monks T.J., Hanzlik R.P., Cohen G.M., Ross D., Graham D.G. Quinone chemistry and toxicity. Toxicology and Applied Pharmacology. 112:1992;2-16.
24. Prinsze C., Dubbelman T.M.A.R., Van Steveninck J. Protein damage induced by small amount of photodynamically generated singlet oxygen or hydroxyl radicals. Biochimica et Biophysica Acta. 1038:1990;152-157.
25. Redinbaugh M.G., Turley R.B. Adaptation of the bicinchoninic acid protein assay for use with microtiter plates and sucrose gradient fraction. Analytical Biochemistry. 153:1986;267-271.
26. Rice-Evans C.A., Miller N.J., Bolwell P.G., Bramley P.M., Pridham J.B. The relative antioxidant activities of plant-derived polyphenolic flavonoids. Free Radical Research. 22:1995;375-383.
27. Rump A.F., Schussler M., Acar D., Cordes A., Ratke R., Theisohn M., Rosen R., Klaus W., Fricke U. Effects of different inotropes with antioxidant properties on acute regional myocardial ischemia in isolated rabbit hearts. General Pharmacology. 26:1995;603-611.
28. Simons J.M., Hart B.A., Ip Vai Ching T.R., Van Dijk H., Labadie R.P. Metabolic activation of natural phenols into selective oxidative burst agonists by activated human neutrophils. Free Radical Biology and Medicine. 8:1990;251-258.
29. Sugihara N., Arakawa T., Ohnishi M., Furuno K. Anti- and pro-oxidative effects of flavonoids on metal-induced lipid hydroperoxide-dependent lipid peroxidation in cultured hepatocytes loaded with alpha-linolenic acid. Free Radical Biology and Medicine. 27:1999;1313-1323.
30. Terao J., Piskula M., Yao Q. Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers. Archives of Biochemistry and Biophysics. 308:1994;278-284.
31. Watts D.C. Creatine kinase. Boyer P.D. The Enzymes. VII. 1973;383-455 Academic Press, New York.
32. Zhou H.M., Tsou C.L. An essential tryptophan residue for rabbit muscle creatine kinase. Biochimica et Biophysica Acta. 830:1985;59-63.