Model studies on the oxidation of benzoyl methionine in a carbohydrate degradation system

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 19, 2014, Pages 4425-4433

  Hellwig, Michael ^a   Löbmann, Katja ^a   Orywol, Tom ^a   Voigt, Annegrit ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Amadori products; dicarbonyl compounds; methionine; protein oxidation; reductone

Indexed keywords

CARBOHYDRATES; OXIDATION; PROTEINS;

AMADORI PRODUCT; DICARBONYL COMPOUNDS; METHIONINE; PROTEIN OXIDATION; REDUCTONE;

AMINO ACIDS;

BENZOIC ACID DERIVATIVE; CARBOHYDRATE; METHIONINE;

CHEMICAL MODEL; CHEMISTRY; OXIDATION REDUCTION REACTION;

BENZOATES; CARBOHYDRATES; METHIONINE; MODELS, CHEMICAL; OXIDATION-REDUCTION;

EID: 84900818883     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf500733f     Document Type: Article

References (44)

1. Berlett, B. S.; Stadtman, E. R. Protein oxidation in aging, disease, and oxidative stress J. Biol. Chem. 1997, 272, 20313-20316
2. Dean, R. T.; Fu, S.; Stocker, R.; Davies, M. J. Biochemistry and pathology of radical-mediated protein oxidation Biochem. J. 1997, 324, 1-18
3. Lund, M. N.; Heinonen, M.; Baron, C. P.; Estévez, M. Protein oxidation in muscle foods: a review Mol. Nutr. Food Res. 2011, 55, 83-95
4. Meltretter, J.; Seeber, S.; Humeny, A.; Becker, C. M.; Pischetsrieder, M. Site-specific formation of Maillard, oxidation, and condensation products from whey proteins during reaction with lactose J. Agric. Food Chem. 2007, 55, 6096-6103
5. Hayashi, R.; Suzuki, F. Determination of methionine sulfoxide in protein and food by hydrolysis with p -toluenesulfonic acid Anal. Biochem. 1985, 149, 521-528
6. Todd, J. M.; Marable, N. L.; Kehrberg, N. L. Methionine sulfoxide determination after alkaline hydrolysis of amino acid mixtures, model protein systems, soy products and infant formulas J. Food Sci. 1984, 49, 1547-1551
7. Baxter, J. H.; Lai, C.-S.; Phillips, R. R.; Dowlati, L.; Chio, J. J.; Luebbers, S. T.; Dimler, S. R.; Johns, P. W. Direct determination of methionine sulfoxide in milkproteins by enzyme hydrolysis/high-performance liquid chromatography J. Chromatogr., A 2007, 1157, 10-16
8. Tannenbaum, S. R.; Barth, H.; Le Roux, J. P. Loss of methionine in casein during storage with autoxidizing methyl linoleate J. Agric. Food Chem. 1969, 17, 1353-1354
9. S1-casein on emulsification with oxidized lipid Agric. Biol. Chem. 1987, 51, 477-481
10. 13C]glucose model systems J. Agric. Food Chem. 2001, 49, 800-803
11. Pfeiffer, Y. V.; Kroh, L. W. Investigation of reactive -dicarbonyl compounds generated from the Maillard reactions of l -methionine with reducing sugars via their stable quinoxaline derivatives J. Agric. Food Chem. 2010, 58, 8293-8299
12. Cuq, J.-L.; Besancon, P.; Chartier, L.; Cheftel, C. Oxidation of methionine residues of food proteins and nutritional availability of protein-bound methionine sulfoxide Food Chem. 1978, 3, 85-102
13. Kroh, L. W. Caramelisation in food and beverages Food Chem. 1994, 51, 373-379
14. Weenen, H. Reactive intermediates and carbohydrate fragmentation in Maillard chemistry Food Chem. 1998, 62, 393-401
15. Wolff, S. P.; Crabbe, M. J. C.; Thornalley, P. J. The autoxidation of glyceraldehydes and other simple monosaccharides Experientia 1984, 40, 244-246
16. Wolff, S. P.; Dean, R. T. Glucose autoxidation and protein modification-the potential role of autoxidative glycosylation in diabetes Biochem. J. 1987, 245, 243-250
17. Thornalley, P. J.; Langborg, A.; Minhas, H. S. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose Biochem. J. 1999, 344, 109-116
18. Ortwerth, B. J.; James, H.; Simpson, G.; Linetsky, M. The generation of superoxide anions in glycation reactions with sugars, osones, and 3-deoxyosones Biochem. Biophys. Res. Commun. 1998, 245, 161-165
19. Azevedo, M.; Falcao, J.; Raposo, J.; Manso, C. Superoxide radical generation by Amadori compounds Free Radical Res. Commun. 1988, 4, 331-335
20. Elgawish, A.; Glomb, M.; Friedlander, M.; Monnier, V. M. Involvement of hydrogen peroxide in collagen cross-linking by high glucose in vitro and in vivo J. Biol. Chem. 1996, 271, 12964-12971
21. Mossine, V. V.; Linetsky, M.; Glinsky, G. V.; Ortwerth, B. J.; Feather, M. S. Superoxide free radical generation by Amadori compounds: the role of acyclic forms and metal ions Chem. Res. Toxicol. 1999, 12, 230-236
22. Gillery, P.; Monboisse, J. C.; Maquart, F. X.; Borel, J. P. Glycation of proteins as a source of superoxide Diabetes Metab. 1988, 14, 25-30
23. Rockland, L. B. Saturated salt solutions for static control of relative humidity between 5 and 40 °C Anal. Chem. 1960, 32, 1375-1376
24. Hellwig, M.; Henle, T. Formyline, a new glycation compound from the reaction of lysine and 3-deoxypentosone Eur. Food Res. Technol. 2010, 230, 903-914
25. Hellwig, M.; Degen, J.; Henle, T. 3-Deoxygalactosone, a "new" 1,2-dicarbonyl compound in milk products J. Agric. Food Chem. 2010, 58, 10752-10760
26. Hellwig, M.; Henle, T. Release of pyrraline in absorbable peptides during simulated gastrointestinal digestion of casein glycated by 3-deoxyglucosone Eur. Food Res. Technol. 2013, 237, 47-55
27. Dubourg, J.; Naffa, P. Oxydation des hexoses reducteurs par loxygene en milieu alcalin Bull. Soc. Chim. Fr. 1959, 9, 1353-1362
28. Bechara, E. J. H.; Dutra, F.; Cardoso, V. E. S.; Sartori, A.; Olympio, K. P. K.; Penatti, C. A. A.; Adhikari, A.; Assuncao, N. A. The dual face of endogenous -aminoketones: pro-oxidizing metabolic weapons Comp. Biochem. Physiol. C 2007, 146, 88-110
29. Liao, M.-L.; Seib, P. A. Chemistry of l -ascorbic acid related to foods Food Chem. 1988, 30, 289-312
30. Pischetsrieder, M.; Rinaldi, F.; Gross, U.; Severin, T. Assessment of the antioxidative and prooxidative activities of two aminoreductones formed during the Maillard reaction: effects on the oxidation of β-carotene, N -acetylhistidine, and cis -alkenes J. Agric. Food Chem. 1998, 46, 2945-2950
31. Yaylayan, V. A.; Huyghues-Despointes, A. Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions, and spectroscopic properties Crit. Rev. Food Sci. Nutr. 1994, 34, 321-369
32. Hodge, J. E.; Rist, C. E. The Amadori rearrangement under new conditions and its significance for non-enzymatic browning reactions J. Am. Chem. Soc. 1953, 75, 316-322
33. Pischetsrieder, M.; Schoetter, C.; Severin, T. Formation of an aminoreductone during the Maillard reaction of lactose with N -acetyllysine or proteins J. Agric. Food Chem. 1998, 46, 928-931
34. Oliver, C. M.; Melton, L. D.; Stanley, R. A. Creating proteins with novel functionality via the Maillard reaction: a review Crit. Rev. Food Sci. Nutr. 2006, 46, 337-350
35. Garrison, W. M.; Bennett, W.; Jayko, M. E. Radiation-induced oxidation of protein in aqueous solution Radiat. Res. 1962, 16, 483-502
36. Hofmann, T.; Bors, W.; Stettmaier, K. Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids J. Agric. Food Chem. 1999, 47, 379-390
37. Glomb, M. A.; Tschirnich, R. Detection of -dicarbonyl compounds in Maillard reaction systems and in vivo J. Agric. Food Chem. 2001, 49, 5543-5550
38. Smuda, M.; Glomb, M. A. Novel insights into the Maillard catalyzed degradation of maltose J. Agric. Food Chem. 2011, 59, 13254-13264
39. Gobert, J.; Glomb, M. A. Degradation of glucose: reinvestigation of reactive -dicarbonyl compounds J. Agric. Food Chem. 2009, 57, 8591-8597
40. Voigt, M.; Smuda, M.; Pfahler, C.; Glomb, M. A. Oxygen-dependent fragmentation reactions during the degradation 1-deoxy- d -erythro-hexo-2,3- diulose J. Agric. Food Chem. 2010, 58, 5685-5691
41. Nukaya, H.; Inaoka, Y.; Ishida, H.; Tsuji, K.; Suwa, Y.; Wakabayashi, K.; Kosuge, T. Modification of the amino group of guanosine by methylglyoxal and other -ketoaldehydes in the presence of hydrogen peroxide Chem. Pharm. Bull. 1993, 41, 649-653
42. Weenen, H. Reactive intermediates and carbohydrate fragmentation in Maillard chemistry Food Chem. 1998, 62, 393-401
43. Hollnagel, A.; Kroh, L. W. Formation of -dicarbonyl fragments from mono- and disaccharides under caramelization and Maillard reaction conditions Z. Lebensm. Unters. Forsch. 1998, 207, 50-54
44. Yaylayan, V. A.; Keyhani, A. Origin of 2,3-pentanedione and 2,3-butanedione in d -glucose/ l -alanine Maillard model systems J. Agric. Food Chem. 1999, 47, 3280-3284