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Effects of phytic acid on the myoglobin-t-butylhydroperoxide-catalysed oxidation of uric acid and peroxidation of erythrocyte membrane lipids

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Abstract

Phytic acid stimulated the myoglobin-t-butylhydroperoxide (TBHP)-catalysed oxidation of uric acid, but inhibited the peroxidation of erythrocyte membrane lipids induced by the same system. Butylated hydroxy-toluene, a free radical chain reaction-terminating antioxidant, also suppressed the myoglobin-TBHP-induced lipid peroxidation. Moreover, phytic acid inhibited the hydroxyl radical-induced degradation of deoxyribose, but the extent of inhibition in this system was reduced by increasing the ferric ion concentration, suggesting that these effects of phytic acid on the myoglobin-TBHP-mediated oxidation are more likely attributable to its metal chelating properties rather than to a free radical scavenging action. The effectiveness of phytic acid, a naturally occurring antioxidant, in the inhibition of both iron- (as previously shown) and myoglobin-dependent lipid peroxidation suggests its possible therapeutic application as a non-toxic antioxidant for ameliorating the extent of oxy-radical-mediated myocardial ischemia/reperfusion damage.

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Abbreviations

ASC:

Ascorbic acid

BHT:

Butylated Hydroxytoluene

DMSO:

Dimethyl Sulfoxide

TBHP:

t-Butylhydroperoxide

TBA:

Thiobarbituric Acid

TBARS:

Thiobarbituric Acid-reactive Substances

References

  1. Simpson PJ, Mickelson JK, Lucchesi BR: Free radical scavengers in myocardial ischemia. Fed Proc 46: 2413–2421, 1987

    Google Scholar 

  2. Flaherty JT, Weisfeldt ML: Reperfusion injury. Free Rad Biol Med 5: 409–419, 1988

    Google Scholar 

  3. Burton KP: Evidence for direct toxic effects of free radicals on the myocardium. Free Rad Biol Med 4: 15–24, 1988

    Google Scholar 

  4. Godin DV: Role of reactive oxygen derived radicals in ischemic heart disease. Can J Cardiol 5: 235–238, 1989

    Google Scholar 

  5. Godin DV, Ko KM, Garnett ME: Altered antioxidant status in ischemic/reperfused rabbit myocardium: effects of allopurinol. Can J Cardiol 5: 365–371, 1989

    Google Scholar 

  6. Godin DV, Bhimji S, McNeill JH: Effects of allopurinol pretreatment on myocardial ultrastructure and arrhythmias following coronary artery occlusion and reperfusion. Virchows Arch. [Cell Pathol] 52 327–341, 1986

    Google Scholar 

  7. Godin DV, Bhimji S: Effects of allopurinol on myocardial ischemic injury induced by coronary artery ligation and reperfusion. Biochem Pharmacol 36: 2101–2107, 1987

    Google Scholar 

  8. Myers CL, Weiss SJ, Kirsh MM, Shepard BM, Shlafer M: Effects of supplementing hypothermic crystalloid cardioplegic solution with catalase, superoxide dismutase, allopurinol, or desferoxamine on functional recovery of globally ischemic and reperfused isolated hearts. J Thorac Cardiovasc Surg 91: 281–289, 1986

    Google Scholar 

  9. van der Kraaij AMM, van Eijk HG, Koster JF: Prevention of postischemic cardiac injury by the orally active iron chelator 1,2-dimethyl-3-hydroxyl-4-pyridine (Ll) and the antioxidant (+)-cyanidanol-3. Circulation 80: 158–164, 1989

    Google Scholar 

  10. Wittenberg JB: Myoglobin-facilitated oxygen diffusion: Role of myoglobin in oxygen entry into muscle. Physiol Rev 50: 559–636, 1970

    Google Scholar 

  11. Tajima G, Shikama K: Autoxidation of oxymyoglobin. An overall stoichiometry including subsequent side reactions. J Biol Chem 262: 12603–12605, 1987

    Google Scholar 

  12. Fox JB, Nicholas RA, Ackerman SA, Swift CE: A multiple wavelength analysis of the reaction between hydrogen peroxide and metmyoglobin. Biochemistry 13: 5178–5186, 1974

    Google Scholar 

  13. Wallace WJ, Houtchens RA, Maxwell JC, Caughey WS: Mechanism of autooxidation for hemoglobins and myoglobins. Promotion of superoxide production by protons and anions. J Biol Chem 257: 4966–4977, 1982

    Google Scholar 

  14. Arroyo CM, Kramer JH, Dickens BF, Weglicki WB: Identification of free radicals in myocardial ischemia/reperfusion by spin trapping with nitrone DMPO. FEBS Lett 221: 101–104, 1987

    Google Scholar 

  15. Bolli R, Jeroundi MO, Patel BS, DuBose CM, Lai EK, Roberts R, McCay PB: Direct evidence that oxygen-derived free radicals contribute to postischemic myocardial dysfunction in the intact dog. Proc Natl Acad Sci USA 86: 4695–4699, 1989

    Google Scholar 

  16. Kanner J, Harel S: Lipid peroxidation and oxidation of several compounds by H2O2 activated metmyoglobin. Lipids 20: 625–628, 1985

    Google Scholar 

  17. Rice HR, Lee MY, Brown WD: Interactions of heme proteins with hydrogen peroxide: protein crosslinking and co-valent binding of benzo[a]pyrene and 17-betaestradiol. Arch Biochem Biophys 221: 417–427, 1983

    Google Scholar 

  18. Graf E, Empson KL, Eaton JW: Phytic acid. A natural antioxidant. J Biol Chem 262: 11647–11650, 1987

    CAS  PubMed  Google Scholar 

  19. Ko KM, Godin DV: Ferric ion-induced peroxidation of erythrocyte membrane lipids: effects of phytic acid and butylated hydroxytoluene. Mol Cell Biochem 95: 125–131, 1990.

    Google Scholar 

  20. Howell RR, Wyngaarden JB: On the mechanism of peroxidation of uric acid by hemoproteins. J Biol Chem 235: 3544–3550, 1960

    Google Scholar 

  21. Godin DV, Schrier SL: Mechanism of inactivation of adenosine triphosphate by carbodiimides. Biochemistry 9: 4068–4077, 1970

    Google Scholar 

  22. Halliwell B, Gutteridge JMC, Aruoma OI: The deoxyrihose method: A simple test-tube assay for determination of rate constants for reactions of hydroxyl radicals. Anal Biochem 165: 215–219, 1987

    Google Scholar 

  23. Millikan GA: Muscle hemoglobin. Physiol Rev 19: 503–554, 1939

    Google Scholar 

  24. Jones DP, Kennedy FG: Intracellular O2 gradients in cardiac myocytes. Lack of a role for myoglobin in facilitation of intracellular O2 diffusion. Biochem Biophys Res Commun 105: 419–424, 1982

    Google Scholar 

  25. Galaris D, Cadenas E, Hochstein P: Glutathione-dependent reduction of peroxides during ferryl- and met-myoglobin interconversion: a potential protective mechanism in muscle. Free Rad Biol Med 6: 473–478, 1989

    Google Scholar 

  26. Galaris D, Cadenas E, Hochstein P: Redox cycling of myoglobin and ascorbate: A potential protective mechanism against reperfusion injury in muscle. Arch Biochem Biophys 273: 497–504, 1989

    Google Scholar 

  27. Ames BN, Cathart R, Schwiers E, Hochstein P: Uric acid provides an antioxidant defense in humans against oxidantand radical-caused aging and cancer: A hypothesis. Proc Natl Acad Sci USA 78: 6858–6852, 1981

    Google Scholar 

  28. Davies KJA, Sevanian A, Muakkassah-Kelly SF, Hochstein P: Uric acid-iron ion complexes. A new aspect of the antioxidant functions of uric acid. Biochem J 235: 747–754, 1986

    Google Scholar 

  29. Thornalley PJ, Trotta RJ, Stern A: Free radical involvement in the oxidative phenomena induced by tert-butylhydroperoxide in erythrocytes. Biochim Biophys Acta 759: 16–22, 1983

    Google Scholar 

  30. Porter WL: Recent trends in food applications of antioxidants. In: MG Simic and M Karel (eds) Autoxidation in Food and Biology Systems. Plenum Press, New York, 1980, pp 295–366

    Google Scholar 

  31. Vincent SH, Grady RW, Shaklai N, Snider JM, Muller-Eberhard U: The influence of heme-binding proteins in heme-catalysed oxidations. Arch Biochem Biophys 265: 539–550, 1988

    Google Scholar 

  32. Martell AE: Chelates of ascorbic acid. Formation and catalytic properties. In: Ascorbic Acid: Chemistry, Metabolism and Uses. Advances in Chemistry Series 200. PA Seib and BM Tolbert (eds). Am Chem Soc, Washington, DC, pp 153–180, 1982

    Google Scholar 

  33. Brown JM, Beehler CJ, Berger EM, Grosso MA, Whitman GJ, Terada LS, Leff JA, Harken AH, Repine JE: Albumin decreases hydrogen peroxide and reperfusion injury in isolated rat hearts. Inflammation 13: 583–589, 1989

    Google Scholar 

  34. Brown JM, Grosso MA, Terada LS, Beehler CJ, Toth KM, Whitman GJ, Harken AH, Repine JE: Erythrocytes decrease myocardial hydrogen peroxide levels and reperfusion injury. Am J Physiol 256: H584-H588, 1989

    Google Scholar 

  35. Brown JM, Grosso MA, Terada LS, Whitman GJR, Banerjee A, White CW, Harken AH, Repine JE: Endotoxin pretreatment increases endogenous myocardial catalase activity and decreases ischemia-reperfusion injury of isolated rat hearts. Proc Natl Acad Sci USA 86: 2516–2520, 1989

    Google Scholar 

  36. Halliwell B: Superoxide-dependent formation of hydroxyl radicals in the presence of iron chelates: is it a mechanism for hydroxyl radical production in biochemical systems? FEBS Lett 92: 321–326, 1978

    Google Scholar 

  37. Gutteridge JMC: The role of superoxide and hydroxyl radicals in phospholipid peroxidation catalysed by iron salts. FEBS Lett 150: 454–458, 1982

    Google Scholar 

  38. Arduini A, Mezzetti A, Porreca E, Lapenna D, DeJulia J, Marzio L, Polidoro G, Cucurullo F: Effect of ischemia and reperfusion on antioxidant enzymes and mitochondrial inner membrane protein in perfused rat hearts. Biochem Biophys Acta 970: 113–121, 1988

    Google Scholar 

  39. Vallance BD, Hume R, Weyers E: Reassessment of changes in leukocyte and serum ascorbic acid after acute myocardial infarction. Br Heart J 40: 64–68, 1978

    Google Scholar 

  40. Galaris D, Eddy L, Arduini A, Cadenas E, Hochstein P: Mechanisms of reoxygenation injury in myocardial infarction: implications of a myoglobin redox cycle. Biochem Biophys Res Comm 160: 1162–1168, 1989

    Google Scholar 

  41. Kuzuya T, Hoshida S, Nishida M, Kim Y, Fuji H, Kitabatake A, Kamada T, Tada M: Role of free radicals and neutrophils in canine myocardial reperfusion injury: myocardial salvage by a novel free radical scavenger, 2-octadecylascorbic acid. Cardiovas Res 23: 323–330, 1989

    Google Scholar 

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Ko, K.M., Godin, D.V. Effects of phytic acid on the myoglobin-t-butylhydroperoxide-catalysed oxidation of uric acid and peroxidation of erythrocyte membrane lipids. Mol Cell Biochem 101, 23–29 (1991). https://doi.org/10.1007/BF00238434

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  • DOI: https://doi.org/10.1007/BF00238434

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