Competitive reduction of perferrylmyoglobin radicals by protein thiols and plant phenols

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 46, 2014, Pages 11279-11288

  Jongberg, Sisse ^a   Lund, Marianne N ^a   Skibsted, Leif H ^a   Davies, Michael J ^b,c  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b HEART RESEARCH INSTITUTE   (Australia)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Myofibrillar proteins; Myoglobin; Plant phenols; Protein oxidation; Protein radicals

Indexed keywords

BODY FLUIDS; ELECTRON SPIN RESONANCE SPECTROSCOPY; PARAMAGNETIC RESONANCE; PHENOLS; PROTEINS;

BOVINE SERUM ALBUMINS; COMPETITIVE REDUCTION; EFFICIENT PROTECTIONS; ELECTRON PARAMAGNETIC RESONANCE SPECTROSCOPY; MYOFIBRILLAR PROTEINS; MYOGLOBIN; PHENOLIC COMPOUNDS; PROTEIN OXIDATION;

PLANT EXTRACTS;

BOVINE SERUM ALBUMIN; FREE RADICAL; IRON; MUSCLE PROTEIN; MYOGLOBIN; PERFERRYL IRON; PHENOL DERIVATIVE; PLANT EXTRACT; THIOL DERIVATIVE;

ANIMAL; BOVINE; CHEMISTRY; HORSE; ILEX; PIG;

ANIMALS; CATTLE; FREE RADICALS; HORSES; ILEX; IRON; MUSCLE PROTEINS; MYOGLOBIN; PHENOLS; PLANT EXTRACTS; SERUM ALBUMIN, BOVINE; SULFHYDRYL COMPOUNDS; SWINE;

EID: 84913534844     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf5041433     Document Type: Article

References (43)

1. George, P.; Irvine, D. H. The reaction between metmyoglobin and hydrogen peroxide. Biochem. J. 1952, 52, 511-517.
2. Gibson, J. F.; Ingram, D. J. E.; Nicholls, P. Free Radical Produced in the Reaction of Metmyoglobin with Hydrogen Peroxide. Nature 1958, 181, 1398-1399.
3. Kroger-Ohlsen, M.; Carlsen, C. U.; Andersen, M. L.; Skibsted, L. H. Pseudoperoxidase activity of myoglobin: Pigment catalyzed formation of radicals in meat systems. In ACS symposium series 807, Free Radicals in Food; Morelle, M., Shahidi, F., Ho, C., Eds.; American Chemical Society: Washington, DC, 2002; pp 138-150.
4. Davies, M. J. Identification of a globin-free radical in equine myoglobin treated with peroxides. Biochim. Biophys. Acta, Bioenerg. 1991, 1077, 86-90.
5. Gunther, M. R.; Kelman, D. J.; Corbett, J. T.; Mason, R. P. Selfperoxidation of Metmyoglobin Results in Formation of an Oxygenreactive Tryptophan-centered Radical. J. Biol. Chem. 1995, 270, 16075-16081.
6. Libardi, S. H.; Skibsted, L. H.; Cardoso, D. R. Oxidation of carbon monoxide by perferrylmyoglobin. J. Agric. Food Chem. 2014, 62, 1950-1955.
7. Witting, P. K.; Douglas, D. J.; Mauk, A. G. Reaction of human myoglobin and H2O2. Involvement of a thiyl radical produced at cysteine 110. J. Biol. Chem. 2000, 275, 20391-20398.
8. DeGray, J. A.; Gunther, M. R.; Tschirret-Guth, R. A.; Ortiz de Montellano, P. R.; Mason, R. P. Peroxidation of a specific tryptophan of metmyoglobin by hydrogen peroxide. J. Biol. Chem. 1997, 272, 2359-2362.
9. Irwin, J. A.; Østdal, H.; Davies, M. J. Myoglobin-Induced Oxidative Damage: Evidence for Radical Transfer from Oxidized Myoglobin to Other Proteins and Antioxidants. Arch. Biochem. Biophys. 1999, 362, 94-104.
10. Kelman, D. J.; DeGray, J. A.; Mason, R. P. Reaction of Myoglobin with Hydrogen Peroxide Forms a Peroxyl Radical Which Oxidizes Substrates. J. Biol. Chem. 1994, 269, 7458-7463.
11. Davies, M. J.; Dean, R. T. Radical-mediated protein oxidation; Oxford Science Publications: Oxford, 2003.
12. Lund, M. N.; Luxford, C.; Skibsted, L. H.; Davies, M. J. Oxidation of myosin by heme proteins generates myosin radicals and protein cross-links. Biochem. J. 2008, 410, 565-574.
13. Frederiksen, A. M.; Lund, M. N.; Andersen, M. L.; Skibsted, L. H. Oxidation of porcine myosin by hypervalent myoglobin: The role of thiol groups. J. Agric. Food Chem. 2008, 56, 3297-3304.
14. Uniprot Consortium, Myosin heavy chain 2b, MYH4-PIG. URL: http://www.uniprot.org/uniprot/Q9TV62 (2014, July 7).
15. Xiong, Y. L.; Park, D.; Ooizumi, T. Variation in the cross-linking pattern of porcine myofibrillar protein exposed to three different oxidative environments. J. Agric. Food Chem. 2009, 57, 153-159.
16. Lund, M. N.; Lametsch, R.; Hviid, M. S.; Jensen, O. N.; Skibsted, L. H. High-Oxygen Packaging Atmosphere Influences Protein Oxidation and Tenderness of Porcine longissimus dorsi during Chill Storage. Meat Sci. 2007, 77, 295-303.
17. Shah, M. A.; Bosco, S. J. D.; Mir, S. A. Plant extracts as natural antioxidants in meat and meat products. Meat Sci. 2014, 98, 21-33.
18. Rodríguez-Carpena, J. G.; Morcuende, D.; Estévez, M. Avocado by-products as inhibitors of color deterioration and lipid and protein oxidation in raw porcine patties subjected to chilled storage. Meat Sci. 2011, 89, 166-173.
19. Rababah, T.; Hettiarachchy, N.; Horax, R.; Eswaranandam, S.; Mauromoustakos, A.; Dickson, J.; Niebuhr, S. Effect of electron beam irradiation and storage at 5C on thiobarbituric acid reactive substances and carbonyl content in chicken breast meat infused with antioxidants and selected plant extracts. J. Agric. Food Chem. 2004, 52, 8236-8241.
20. Lara, M. S.; Gutierrez, J. I.; Timón, M.; Andrés, A. I. Evaluation of two natural extracts (Rosmarinus officinalis L. and Melissa officinalis L.) as antioxidants in cooked pork patties packed in MAP. Meat Sci. 2011, 88, 481-488.
21. Jongberg, S.; Tørngren, M. A.; Gunvig, A.; Skibsted, L. H.; Lund, M. N. Effect of green tea or rosemary extract on protein oxidation in Bologna type sausages prepared from oxidatively stressed pork. Meat Sci. 2013, 93, 538-546.
22. Jongberg, S.; Lund, M. N.; Ostdal, H.; Skibsted, L. H. Phenolic antioxidant scavenging of myosin radicals generated by hypervalent myoglobin. J. Agric. Food Chem. 2012, 60, 12020-12028.
23. Lundblad, R. L. Techniques in protein modification; CRC Press: Boca Raton, FL, 1995.
24. Singleton, V. L.; Rossi, J. A. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am. J. Enol. Vitic. 1965, 16, 144-158.
25. Park, D.; Xiong, Y. L. Oxidative modification of amino acids in porcine myofibrillar protein isolates exposed to three oxidizing systems. Food Chem. 2007, 103, 607-616.
26. Koutina, G.; Jongberg, S.; Skibsted, L. H. Protein and lipid oxidation in Parma ham during production. J. Agric. Food Chem. 2012, 60, 9737-9745.
27. Ellman, G. L. Tissue Sulfhydryl Groups. Arch. Biochem. Biophys. 1959, 82, 70-77.
28. Jongberg, S.; Terkelsen, L. S.; Miklos, R.; Lund, M. N. Green tea extract impair meat emulsion properties by disturbing protein disulfide cross-linking. Meat Sci. 2015, 100, 2-9.
29. Andersen, H. J.; Skibsted, L. H. Kinetics and Mechanism of Thermal Oxidation and Photooxidation of Nitrosylmyoglobin in Aqueous Solution. J. Agric. Food Chem. 1992, 40, 1741-1750.
30. Kajer, T. B.; Fairfull-Smith, K. E.; Yamasaki, T.; Yamada, K.; Fu, S.; Bottle, S. E.; Hawkins, C. L.; Davies, M. J. Inhibition of myeloperoxidase- and neutrophil-mediated oxidant production by tetraethyl and tetramethyl nitroxides. Free Radical Biol. Med. 2014, 70, 96-105.
31. Lametsch, R.; Larsen, M. R.; Essén-Gustavsson, B.; Jensen-Waern, M.; Lundstrom, K.; Lindahl, G. Postmortem changes in pork muscle protein phosphorylation in relation to RN genotype. J. Agric. Food Chem. 2011, 59, 11608-11615.
32. 2-activated metmyoglobin and other proteins. Free Radical Biol. Med. 1997, 23, 754-761.
33. Turell, L.; Radi, R.; Alvarez, B. The thiol pool in human plasma: The central contribution of albumin to redox processes. Free Radical Biol. Med. 2013, 65, 244-253.
34. Bravo, L.; Goya, L.; Lecumberri, E. LC/MS characterization of phenolic constituents of mate (Ilex paraguariensis, St. Hil.) and its antioxidant activity compared to commonly consumed beverages. Food Res. Int. 2007, 40, 393-405.
35. Brewer, M. S. Natural antioxidants: Sources, compounds, mechanisms of action, and potential applications. Comp. Rev. Food Sci. Food Saf. 2011, 10, 221-247.
36. Heck, C. I.; De Mejia, E. G. Yerba mate tea (Ilex paraguariensis): A comprehensive review on chemistry, health implications, and technological considerations. J. Food Sci. 2007, 72, R138-R151.
37. Østdal, H.; Andersen, H. J.; Davies, M. J. Formation of longlived radicals on proteins by radical transfer from heme enzymes - A common process? Arch. Biochem. Biophys. 1999, 362, 105-112.
38. Chen, Y. R.; Chen, C. L.; Chen, W.; Zweier, J. L.; Augusto, O.; Radi, R.; Mason, R. P. Formation of protein tyrosine orthosemiquinone radical and nitrotyrosine from cytochrome c-derived tyrosyl radical. J. Biol. Chem. 2004, 279, 18054-18062.
39. Dalsgaard, T. K.; Nielsen, J. H.; Brown, B. E.; Stadler, N.; Davies, M. J. Dityrosine, 3,4-dihydroxyphenylalanine (DOPA), and radical formation from tyrosine residues on milk proteins with globular and flexible structures as a result of riboflavin-mediated photooxidation. J. Agric. Food Chem. 2011, 59, 7939-7947.
40. Silva, F. A. M.; Borges, F.; Guimarães, C.; Lima, J. L. F. C.; Matos, C.; Reis, S. Phenolic acids and derivatives: Studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J. Agric. Food Chem. 2000, 48, 2122-2126.
41. Bentayeb, K.; Rubio, C.; Batlle, R.; Nerín, C. Direct determination of carnosic acid in a new active packaging based on natural extract of rosemary. Anal. Bioanal. Chem. 2007, 389, 1989-1996.
42. Herrero-Martínez, J. M.; Sanmartin, M.; Rosés, M.; Bosch, E.; Ráfols, C. Determination of dissociation constants of flavonoids by capillary electrophoresis. Electrophoresis 2005, 26, 1886-1895.
43. Lorrain, B.; Dangles, O.; Genot, C.; Dufour, C. Chemical modeling of heme-induced lipid oxidation in gastric conditions and inhibition by dietary polyphenols. J. Agric. Food Chem. 2010, 58, 676-683.