Heme-mediated production of free radicals via preformed lipid hydroperoxide fragmentation

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 23, 2008, Pages 11478-11484

  Pazos, Manuel ^b   Andersen, Mogens L ^a   Skibsted, Leif H ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b INSTITUTO DE INVESTIGACIONES MARINAS   (Spain)

Author keywords

ESR; Free radicals; Heme group; Hydroperoxides; Lipid oxidation; Pro oxidant; Spin trapping

Indexed keywords

BENZENE DERIVATIVE; CUMENE HYDROPEROXIDE; FISH PROTEIN; FREE RADICAL; HEME; HEMOPROTEIN; LIPID PEROXIDE;

ANIMAL; ARTICLE; CHEMISTRY; RAINBOW TROUT;

ANIMALS; BENZENE DERIVATIVES; FISH PROTEINS; FREE RADICALS; HEME; HEMEPROTEINS; LIPID PEROXIDES; ONCORHYNCHUS MYKISS;

BOVINAE; ONCORHYNCHUS MYKISS;

EID: 58949089567     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf802359t     Document Type: Article

References (35)

1. Kanner, J. Oxidative processes in meat and meat products quality implications. Meat Sci. 1994, 36, 169-189.
2. Roberts, L. J.; Morrow, J. D. Products of the isoprostane pathway: unique bioactive compounds and markers of lipid peroxidation. Cell. Mol. Life Sci. 2002, 59, 808-820.
3. Halliwell, B. Lipid peroxidation, antioxidants and cardiovascular disease: how should we move forward? Cardiovasc. Res. 2000, 47, 410-418.
4. Montine, K. S.; Quinn, J. F.; Zhang, J.; Fessel, J. P.; Roberts, L. J.; Morrow, J. D.; Montine, T. J. Isoprostanes and related products of lipid peroxidation in neurodegenerative diseases. Chem. Phys. Lipids 2004, 128, 117-124.
5. Frankel, E. N. Lipid Oxidation; The Oily Press: Dundee, Scotland, 1998.
6. Girotti, A. W. Lipid hydroperoxide generation, turnover, and effector action in biological systems. J. Lipid Res. 1998, 39, 1529-1542.
7. Aw, T. Y. Determinants of intestinal detoxication of lipid hydroperoxides. Free Radical Res. 1998, 28, 637-646.
8. Lapidot, T.; Granit, R.; Kanner, J. Lipid hydroperoxidase activity of myoglobin and phenolic antioxidants in simulated gastric fluid. J. Agric. Food Chem. 2005, 53, 3391-3396.
9. Ursini, F.; Zamburlini, A.; Cazzolato, G.; Maiorino, M.; Bon, G. B.; Sevanian, A. Postprandial plasma lipid hydroperoxides: a possible link between diet and atherosclerosis. Free Radical Biol. Med. 1998, 25, 250-252.
10. Pazos, M.; Medina, I.; Hultin, H. O. Effect of ph on hemoglobin-catalized lipid oxidation in cod muscle membranes in vitro and in situ. J. Agric. Food Chem. 2005, 53, 3605-3612.
11. Pazos, M.; Lois, S.; Torres, J. L.; Medina, I. Inhibition of hemoglobin- and iron-promoted oxidation in fish microsomes by natural phenolics. J. Agric. Food Chem. 2006, 54, 4417-4423.
12. Richards, M. P.; Hultin, H. O. Contribution of blood and blood components to lipid oxidation in fish muscle. J. Agric. Food Chem. 2002, 50, 555-564.
13. Reeder, B. J.; Svistunenko, D. A.; Cooper, C. E.; Wilson, M. T. The radical and redox chemistry of myoglobin and hemoglobin: from in vitro studies to human pathology. Antioxid. Redox Signaling 2004, 6, 954-966.
14. O'Brien, P. J. Intracellular mechanisms for the decomposition of a lipid peroxide. I. Decomposition of a lipid peroxide by metal ions, heme compounds and nucleophiles. Can. J. Fish Aquat. Sci. 1969, 47, 485-492.
15. Omodeo-Sale, F.; Monti, D.; Olliaro, P.; Taramelli, D. Prooxidant activity of β-hematin (synthetic malaria pigment) in arachidonic acid micelles and phospholipid large unilamellar vesicles. Biochem. Pharmacol. 2001, 61, 999-1009.
16. Grunwald, E. W.; Richards, M. P. Studies with myoglobin variants indicate that released hemin is the primary promoter of lipid oxidation in washed fish muscle. J. Agric. Food Chem. 2006, 54, 4452-4460.
17. Richards, M. P.; Hultin, H. O. Effect of ph on lipid oxidation using trout hemolysate as a catalyst: a possible role for deoxyhemoglobin. J. Agric. Food Chem. 2000, 48, 3141-3147.
18. Fyhn, U. E.; Fyhn, H. J.; Davis, B. J.; Powers, D. A.; Fink, W. L.; Garlik, R. L. Hemoglobin heterogeneity in amozonian fishes. Comp. Biochem. Physiol. 1979, 62A, 39-66.
19. Svistunenko, D. A.; Dunne, J.; Fryer, M.; Nicholls, P.; Reeder, B. J.; Wilson, M. T.; Bigotti, M. G.; Cutruzzola, F.; Cooper, C. E. Comparative study of tyrosine radicals in hemoglobin and myoglobins treated with hydrogen peroxide. Biophys. J. 2002, 83, 2845-2855.
20. Brown, W. D. Chromatography of myoglobin on diethylaminoethyl cellulose columnas. J. Biol. Chem. 1961, 236, 2238-2240.
21. Duling, D. R. Simulation of multiple isotropic spin-trap EPR spectra. J. Magn. Reson. B 1994, 104, 105-110.
22. Iwahashi, H.; Albro, P. W.; McGown, S. R.; Tomer, K. B.; Mason, R. P. Isolation and identification of α-(4-pyridyl-1-oxide)-N-tert- butylnitrone radical adducts formed by the decomposition of the hydroperoxides of linoleic acid, linolenic acid, and arachidonic acid by soybean lipoxygenase. Arch. Biochem. Biophys. 1991, 285, 172-180.
23. Hix, S.; Kadiiska, M. B.; Mason, R. P.; Augusto, O. In vivo metabolism of tert-butyl hydroperoxide to methyl radicals. EPR spin-trapping and DNA methylation studies. Chem. Res. Toxicol. 2000, 13, 1056-1064.
24. Pazos, M.; Andersen, M. L.; Skibsted, L. H. Amino acid and protein scavenging of radicals generated by iron and hydroperoxides: an electron spin resonance (ESR) spin-trapping study. J. Agric. Food Chem. 2006, 54, 10215-10221.
25. Chamulitrat, W.; Hughes, M. F.; Eling, T. E.; Mason, R. P. Superoxide and peroxyl radical generation from the reduction of polyunsaturated fatty acid hydroperoxides by soybean lipoxygenase. Arch. Biochem. Biophys. 1991, 290, 153-159.
26. Barr, D. P.; Mason, R. P. Mechanism of radical production from the reaction of cytochrome-c with organic hydroperoxides - an ESR spin-trapping investigation. J. Biol. Chem. 1995, 270, 12709-12716.
27. Rehorek, D.; Janzen, E. G. On the formation of arseno aminoxyls (nitroxides) by spin trapping of arseno radicals. Polyhedron 1984, 3, 631-634.
28. Obrien, P. J. Intracellular mechanisms for the decomposition of a lipid peroxide. I. Decomposition of a lipid peroxide by metal ions, heme compounds and nucleophiles. Can. J. Biochem 1969, 47, 485-492.
29. Rota, C.; Barr, D. P.; Martin, M. V.; Guengerich, F. P.; Tomas, A.; Mason, R. P. Detection of free radicals produced from the reaction of cytochrome p-450 with linoleic acid hydroperoxide. J. Biochem. 1997, 328, 565-571.
30. Kalyanaraman, B.; Perezreyes, E.; Mason, R. P. Reduction of nitroso-spin traps in chemical and biological-systems - cautionary note. Tetrahedron Lett. 1979, 4809-4812.
31. Guo, Q.; Qian, S. Y.; Mason, R. P. Separation and identification of dmpo adducts of oxygen-centered radicals formed from organic hydroperoxides by HPLC-ESR, ESI-MS and MS/MS. J. Am. Soc. Mass. Spectrom 2003, 14, 862-871.
32. Kambayashi, Y.; Tero-Kubota, S.; Yamamoto, Y.; Kato, M.; Nakano, M.; Yagi, K.; Ogino, K. Formation of superoxide anion during ferrous ion-induced decomposition of linoleic acid hydroperoxide under aerobic conditions. J. Biochem. 2003, 134, 903-909.
33. Grunwald, E. W.; Richards, M. P. Mechanisms of heme protein-mediated lipid oxidation using hemoglobin and myoglobin variants in raw and heated washed muscle. J. Agric. Food Chem. 2006, 54, 8271-8280.
34. Nath, K. A.; Haggard, J. J.; Croatt, A. J.; Grande, J. P.; Poss, K. D.; Alam, J. The indispensability of heme oxygenase-1 in protecting against acute heme protein-induced toxicity in vivo. Am. J. Pathol. 2000, 156, 1527-1535.
35. Reeder, B. J.; Wilson, M. T. Mechanism of reaction of myoglobin with the lipid hydroperoxide hydroperoxyoctadecadienoic acid. Biochem. J. 1998, 330, 1317-1323.