Formation of /Nε-(carboxymethyI)lysine and loss of lysine in casein glucose-Fatty acid model systems

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 3, 2010, Pages 1954-1958

  Lima, Maria ^a   Assar, Shima H ^b   Ames, Jennifer M ^c  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

^b UNIVERSITY OF SOUTH CAROLINA   (United States)

^c NORTHUMBRIA UNIVERSITY   (United Kingdom)

Author keywords

Advanced glycatlon end products; Advanced lipoxldatlon end products; CML precursors; N (carboxymethyl)lyslne; Ultrapressure liquid chromatography Tandem mass spectrometry

Indexed keywords

CASEIN; DRUG DERIVATIVE; FATTY ACID; GLUCOSE; LYSINE; N(6) CARBOXYMETHYLLYSINE; N(6)-CARBOXYMETHYLLYSINE;

ANIMAL; ARTICLE; CATTLE; CHEMICAL MODEL; CHEMISTRY;

ANIMALS; CASEINS; CATTLE; FATTY ACIDS; GLUCOSE; LYSINE; MODELS, CHEMICAL;

EID: 76449095750     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf903562c     Document Type: Article

References (30)

1. Nursten, H. The Maillard Reaction Chemistry, Biochemistry and Implications; Royal Society of Chemistry: Cambridge, U.K., 2005.
2. Ahmed, M. U.; Thorpe, S. R.; Baynes, J. W. Identification of Nε-(carboxymethyl)lysine as a degradation product of fructoselysine in glycated protein. J. Biol. Chem. 1986, 261, 4889-4894.
3. 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.
4. ε- (carboxymethyl)lysine, is a product of both lipid peroxidation and glycoxidation reactions. J. Biol. Chem. 1996, 271, 9982-9986.
5. Refsgaard, H. H.; Tsai, L.; Stadtman, E. R. Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proc. Natl. Acad. Sci. U.S.A. 1999, 97, 611-616.
6. Baynes, J. W.; Thorpe, S. R. Glycoxidation and lipoxidation in atherogenesis. Free Radical Biol. Med. 2000, 28, 1708-1716.
7. (7) Drusch, S.; Faist, V.; Erbersdobler, H. F. Determination of Nε--carboxymethyllysine in milk products by a modified reversedphase HPLC method. Food Chem. 1999, 65, 547-553. (Pubitemid 29142478)
8. (8) Goldberg, T.; Cai, W.; Peppa, M.; Dardaine, V.; Baliga, B. S.; Uribarri, J.; Vlassara, H. Advanced glycoxidation end products in commonly consumed foods. J. Am. Diet. Assoc. 2004, 104, 1287-1291. (Pubitemid 39036519)
9. Ahmed, N.; Mirshekar-Syahkal, B.; Kennish, L.; Karachalias, N.; Babaei-Jadidi, R.; Thornalley, P. J. Assay of advanced glycation end-products in selected beverages and food by liquid chromatography with tandem mass spectrometric detection. Mol Nutr. Food Res. 2005, 49, 691-699.
10. Guy, P. A.; Fenaille, F. Contribution of mass spectrometry to assess quality of milk-based products. Mass Spectrom. Rev. 2006, 25, 290-326.
11. ε-(carboxymethyl)lysine in food systems by ultra performance liquid chromatography-mass spectrometry. Amino Acids 2009, 36, 317-326.
12. s1 casein in goat's milk with different genotypes by capillary electrophoresis. J. Chromatogr., A 2004, 1054, 279-284.
13. Folch, J.; Lees, M.; Stanely, G. H. S. A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem. 1957, 226, 497-509.
14. 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.
15. Namiki, M.; Hayashi, T. A new mechanism of the Maillard reaction involving sugar fragmentation and free radical formation. In The Maillard Reaction in Foods and Nutrition; Waller, G. R., Feather, M. S., Eds.; American Chemical Society: Washington, DC, 1983; pp 21-46.
16. Hodge, J. E. Dehydrated foods: chemistry of browning reactions in model systems. J. Agrie. Food Chem. 1953, 1, 928-943.
17. Glomb, M. A.; Monnier, V. M. Mechanism of protein modification by glyoxal and glycoaldehyde, reactive intermediates of the Maillard reaction. J. Biol. Chem. 1995, 270, 10017-10026.
18. Brock, J. W. C.; Hinton, D. J. S.; Cotham, W. E.; Metz, T. O.; Thorpe, S. R.; Baynes, J. W.; Ames, J. M. Proteomic analysis of the site specificity of glycation and carboxymethylation of ribonuclease. J. Proteome Res. 2003, 2, 506-513.
19. Wells-Knecht, M. C.; Thorpe, S. R.; Baynes, J. W. Pathways of formation of glycoxidation products during glycation of collagen. Biochemistry 1995, 34, 15134-15141.
20. Watkins, N. G.; Negliafisher, C. I.; Dyer, D. G.; Thorpe, S. R.; Baynes, J. W. Effect of phosphate on the kinetics and specificity of glycation of protein. J. Biol. Chem. 1987, 262, 7207-7212.
21. (21) Scaloni, A.; Valentina, P.; Franco, P.; Fedele, E.; Froio, R.; Ferrara, L.; Bergamo, P. Characterization of heat-induced lactosylation products in caseins by immunoenzymatic and mass spectrometric methodologies. Biochim. Biophys. Acta 2002, 7595, 30-39. (Pubitemid 41128019)
22. Baynes, J. W.; Ahmed, M. U.; Fisher, C. I.; Hull, C. J.; Lehman, T. A.; Watkins, N. G.; Thorpe, S. R. Studies on glycation of protein and Maillard reactions of glycated protein under physiological conditions. In Amino-Carbonyl Reactions in Food and Biological Systems; Fujimaki, M., Kato, H., Namiki, M., Eds.; Elsevier: Amsterdam, The Netherlands, 1986; pp 421-431.
23. Fu, M. X.; Knecht, K. J.; Thorpe, S. R.; Baynes, J. W. Role of oxygen in cross-linking and chemical modification of collagen by glucose. Diabetes 1992, 41, 42-48.
24. (24) Miyata, T.; Inagi, R.; Asahi, K.; Yamada, Y.; Horie, K.; Sakai, H.; Uchida, K; Kurokawa, K. Generation of protein carbonyls by gluoxidation and lipoxidation reactions with autoxidation products of ascorbic acid and polyunsaturated fatty acids. FEBS Lett. 1998, 437, 24-28. (Pubitemid 28498234)
25. Fenaille, F.; Parisod, V.; Visani, P.; Populaire, S.; Tabet, J.; Guy, P. A. Modifications of milk constituents during processing: a preliminary benchmarking study. Int. Dairy J. 2006, 16, 728-739.
26. Westwood, M. E.; Thornalley, P. J. Glycation and advanced glycation end-products. In The Glycation Hypothesis of Atherosclerosis; Colaco, C. A. L. S., Ed.; Springer-Verlag: Heidelberg, Germany, 1997; pp 58-87.
27. Esterbauer, H.; Schaur, R. J.; Zollner, H. Chemistry and biochemistry of 4-hydroxynonenal, malondialdehyde and related aldehydes. Free Radical Biol. Med. 1991, 11, 81-128.
28. (28) Ishii, T.; Kumazawa, S.; Sakurai, T.; Nakayama, T.; Uchida, K. Mass spectroscopic characterization of protein modification by malondialdehyde. Chem. Res. Toxicol. 2006, 19, 122-129. (Pubitemid 43185470)
29. (29)Requena,J.R.;Fu,M.X.;Ahmed,M.U.;Jenkins,A.J.;Lyons,T.J.;Baynes,J.W. ;Thorpe,S.R.Quantificationofmalondialdehydeand4-hydroxynonenaladducts- lysineresiduesinnativeandoxidizedhumanlow-densitylipoprotein.Biochem.J.1997,322, 317-325.(Pubitemid27095558)
30. (30)Belkner,J.;Wiesner,R.;Rathman,J.;Sigal,E.;Kuhn,H.Oxygena- tionoflipoproteinsbymammalianlipoxygenases.Eur.J.Biochem.1993,275,215-261. (Pubitemid23106053)