Characterisation of Maillard reaction products derived from LEKFD - A pentapeptide found in β-lactoglobulin sequence, glycated with glucose - By tandem mass spectrometry, molecular orbital calculations and gel filtration chromatography coupled with continuous photodiode array

Food Chemistry

Volumn 145, Issue , 2014, Pages 892-902

  Yamaguchi, Keiko ^a   Homma, Takeshi ^a   Nomi, Yuri ^b   Otsuka, Yuzuru ^b  

^a JAPAN WOMEN'S UNIVERSITY   (Japan)

^b OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Lactoglobulin; Maillard reaction; Modified peptide

Indexed keywords

GEL-FILTRATION; GEL-FILTRATION CHROMATOGRAPHY; LACTOGLOBULIN; MAILLARD REACTION; MAILLARD REACTION PRODUCTS; PHOTODIODE ARRAYS; SCHIFF-BASE; TANDEM MASS SPECTROMETRY;

AMINO ACIDS; BIOACTIVITY; CHEMICAL REACTIONS; FINITE DIFFERENCE METHOD; FUNCTIONAL GROUPS; GEL PERMEATION CHROMATOGRAPHY; GLUCOSE; IONS; MASS SPECTROMETRY; MOLECULAR ORBITALS; ORBITAL CALCULATIONS; PEPTIDES;

GLYCOSYLATION;

GLUCOSE; PENTAPEPTIDE; SCHIFF BASE;

ARTICLE; CALCULATION; ELECTROSPRAY MASS SPECTROMETRY; GEL FILTRATION CHROMATOGRAPHY; GLYCATION; HEAT; PROTEIN CROSS LINKING; PROTEIN DEGRADATION; TANDEM MASS SPECTROMETRY;

MAILLARD REACTION; MODIFIED PEPTIDE; Β-LACTOGLOBULIN;

ANIMALS; CATTLE; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPEPTIDES; ELECTROCHEMICAL TECHNIQUES; GLYCOPROTEINS; GLYCOSYLATION; HOT TEMPERATURE; LACTOGLOBULINS; MAILLARD REACTION; MODELS, MOLECULAR; OLIGOPEPTIDES; PEPTIDE FRAGMENTS; PROTEIN CONFORMATION; PROTEIN STABILITY; PROTEOLYSIS; SCHIFF BASES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 84884527661     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2013.08.134     Document Type: Article

References (56)

1. J.M. Ames Evidence against dietary advanced glycation endproducts being a risk to human health Molecular Nutrition & Food Research 51 9 2007 1085 1090 (Pubitemid 47522799)
2. S. Arena, G. Renzone, G. Novi, A. Paffetti, G. Bernardini, and A. Santucci Modern proteomic methodologies for the characterization of lactosylation protein targets in milk Proteomics 10 19 2010 3414 3434
3. E. Babiker, A. Hiroyuki, N. Matsudomi, H. Iwata, T. Ogawa, and N. Bando Effect of polysaccharide conjugation or transglutaminase treatment on the allergenicity and functional properties of soy protein Journal of Agriculture and Food Chemistry 46 2 1998 866 871 (Pubitemid 128488082)
4. J.W. Baynes The role of AGEs in aging: Causation or correlation Experimental Gerontology 36 9 2001 1527 1537 (Pubitemid 32771329)
5. F. Chevalier, J.-M. Chobert, Y. Popineau, M.G. Nicolas, and T. Haertlé Improvement of functional properties of β-lactoglobulin glycated through the Maillard reaction is related to the nature of the sugar International Dairy Journal 11 3 2001 145 152 (Pubitemid 32682566)
6. J.-M. Chobert, J.-C. Gaudin, M. Dalgalarrondo, and T. Haertlé Impact of Maillard type glycation on properties of β-lactoglobulin Biotechnology Advances 24 6 2006 629 632 (Pubitemid 44499001)
7. M. Corzo-Martínez, R. Lebrón-Aguilar, M. Villamiel, J.E. Quintanilla-López, and F.J. Moreno Application of liquid chromatography-tandem mass spectrometry for the characterization of galactosylated and tagatosylated beta-lactoglobulin peptides derived from in vitro gastrointestinal digestion Journal of Chromatography A 1216 43 2009 7205 7212
8. T. Cucu, B. De Meulenaer, B. Kerkaert, I. Vandenberghe, and B. Devreese MALDI-based identification of whey protein derived tryptic marker peptides that resist protein glycation Food Research International 47 1 2012 23 30
9. J. De Block, M. Merchiers, L. Mortier, A. Braekman, W. Ooghe, and R. van Renterghem Monitoring nutritional quality of milk powders: Capillary electrophoresis of the whey protein fraction compared with other methods International Dairy Journal 13 2 2003 83 94
10. S. Dong, A. Panya, M. Zeng, B. Chen, D.J. McClements, and E.A. Decker Characteristics and antioxidant activity of hydrolyzed β-lactoglobulin- glucose Maillard reaction products Food Research International 46 1 2012 55 61
11. F. Fenaille, F. Morgan, V. Parisod, J.C. Tabet, and P.A. Guy Solid-state glycation of β-lactoglobulin monitored by electrospray ionisation mass spectrometry and gel electrophoresis techniques Rapid Communications in Mass Spectrometry 17 13 2003 1483 1492 (Pubitemid 36791157)
12. F. Fenaille, F. Morgan, V. Parisod, J.C. Tabet, and P.A. Guy Solid-state glycation of β-lactoglobulin by lactose and galactose: Localization of the modified amino acids using mass spectrometric techniques Journal of Mass Spectrometry 39 1 2004 16 28 (Pubitemid 38208527)
13. V. Fogliano, S.M. Monti, A. Visconti, G. Randazzo, A.M. Facchiano, and G. Colonna Identification of a β-lactoglobulin lactosylation site Biochimica et Biophysica Acta 1388 2 1998 295 304
14. A. Frolov, and R. Hoffmann Analysis of amadori peptides enriched by boronic acid affinity chromatography Annals of the New York Academy of Sciences 1126 1 2008 253 256 (Pubitemid 351589322)
15. A. Frolov, P. Hoffmann, and R. Hoffmann Fragmentation behavior of glycated peptides derived from d-glucose, d-fructose and d-ribose in tandem mass spectrometry Journal of Mass Spectrometry 41 11 2006 1459 1469 (Pubitemid 44875656)
16. I. Gaucher, D. Mollé, V. Gagnaire, and F. Gaucheron Effects of storage temperature on physico-chemical characteristics of semi-skimmed UHT milk Food Hydrocolloids 22 1 2008 130 143 (Pubitemid 47002061)
17. F. Guyomarc'h, F. Warin, D.D. Muir, and J. Leaver Lactosylation of milk proteins during the manufacture and storage of skim milk powders International Dairy Journal 10 12 2000 863 872 (Pubitemid 32247651)
18. J.E. Hodge Chemistry of browning reactions in models systems Journal of Agriculture and Food Chemistry 1 15 1953 928 943
19. S. Horvat, and A. Jakas Peptide and amino acid glycation: New insights into the Maillard reaction Journal of Peptide Science 10 3 2004 119 137 (Pubitemid 38477090)
20. I. Jerić, C. Versluis, S. Horvat, and A.J. Heck Tracing glycoprotein structures: electrospray ionization tandem mass spectrometric analysis of sugar-peptide adducts Journal of Mass Spectrometry 37 8 2002 803 811 (Pubitemid 35012519)
21. Z. Jiang, and A. Brodkorb Structure and antioxidant activity of Maillard reaction products from α-lactalbumin and β-lactoglobulin with ribose in an aqueous model system Food Chemistry 133 3 2012 960 968
22. H. Jing, Y. Melissa, P.Y.Y. Wong, and D.D. Kitts Comparison of physicochemical and antioxidant properties of egg-white proteins and fructose and inulin Maillard reaction products Food and Bioprocess Technology 4 8 2011 1489 1496
23. T. Katsumata, H. Nakakuki, C. Tokunaga, N. Fujii, M. Egi, and T.H. Phan Effect of Maillard reacted peptides on human salt taste and the amiloride-insensitive salt taste receptor (TRPV1t) Chemical Senses 33 7 2008 665 680
24. X.H. Lan, P. Liu, S.Q. Xia, C.S. Jia, D. Mukunzi, and X.M. Zhang Temperature effect on the non-volatile compounds of Maillard reaction products derived from xylose-soybean peptide system: Further insights into thermal degradation and cross-linking Food Chemistry 120 4 2010 967 972
25. A. Lapolla, D. Fedele, R. Reitano, N.C. Arico, R. Seraglia, and P. Traldi Enzymatic digestion and mass spectrometry in the study of advanced glycation end products/peptides Journal of the American Society for Mass Spectrometry 15 4 2004 496 509 (Pubitemid 38407135)
26. J. Leonil, D. Molle, J. Fauquant, J.L. Maubois, R.J. Pearce, and S. Bouhallab Characterization by ionization mass spectrometry of lactosyl β-lactoglobulin conjugates formed during heat treatment of milk and whey and identification of one lactose-binding site Journal of Dairy Science 80 10 1997 2270 2281 (Pubitemid 127446920)
27. W. Lertittikul, S. Benjakul, and M. Tanaka Characteristics and antioxidative activity of Maillard reaction products from a porcine plasma protein-glucose model system as influenced by pH Food Chemistry 100 2 2007 669 677 (Pubitemid 43928367)
28. P. Liu, M. Huang, S. Song, K. Hayat, X. Zhang, and S. Xia Sensory characteristics and antioxidant activities of Maillard reaction products from Soy protein hydrolysates with different molecular weight distribution Food and Bioprocess Technology 5 5 2012 1775 1789
29. C.Y. Lu, Z.G. Hao, R. Payne, and C.-T. Ho Effects of water content on volatile generation and peptide degradation in the Maillard reaction of glycine, diglycine, and triglycine Journal of Agriculture and Food Chemistry 53 16 2005 6443 6447 (Pubitemid 41169398)
30. A. Medrano, C. Abirached, L. Panizzolo, P. Moyna, and M.C. Añón The effect of glycation on foam and structural properties of β-lactoglobulin Food Chemistry 113 1 2009 127 133
31. J. Meltretter, S. Seeber, A. Humeny, C.M. Becker, and M. Pischetsrieder Site-specific formation of Maillard, oxidation, and condensation products from whey proteins during reaction with lactose Journal of Agriculture and Food Chemistry 55 15 2007 6096 6103 (Pubitemid 47235664)
32. C. Mennella, M. Visciano, A. Napolitano, M.D. Del Castillo, and V. Fogliano Glycation of lysine-containing dipeptides Journal of Peptide Science 12 4 2006 291 296
33. J.K. Moon, and T. Shibamoto Formation of carcinogenic 4(5)-methylimidazole in Maillard reaction systems Journal of Agriculture and Food Chemistry 59 2 2011 615 618
34. F.J. Moreno, J.E. Quintanilla-López, R. Lebrón-Aguilar, A. Olano, and M.L. Sanz Mass spectrometric characterization of glycated β-lactoglobulin peptides derived from galacto-oligosaccharides surviving the in vitro gastrointestinal digestion Journal of the American Society for Mass Spectrometry 19 7 2008 927 937
35. F. Morgan, S. Bouhallab, D. Molle, G. Henry, J.L. Maubois, and J. Leonil Lactolation of β-lactoglobulin monitored by electrospray ionisation mass spectrometry International Dairy Journal 8 2 1998 95 98 (Pubitemid 28434027)
36. S. Nakamura, and A. Kato Multi-functional biopolymer prepared by covalent attachment of galactomannan to egg-white proteins through naturally occurring Maillard reaction Nahrung 44 3 2000 201 206
37. M. Ogasawara, T. Katsumata, and M. Egi Taste properties of Maillard-reaction products prepared from 1000 to 5000 Da peptide Food Chemistry 99 3 2006 600 604
38. Y.-C. Oh, C.-K. Shu, and C.-T. Ho Some volatile compounds formed from thermal interaction of glucose with glycine, diglycine, triglycine, and tetraglycine Journal of Agriculture and Food Chemistry 39 9 1991 1553 1554
39. G.A. Pallante, and C.J. Cassady Effects of peptide chain length on the gas-phase proton transfer properties of doubly-protonated ions from bradykinin and its N-terminal fragment peptides International Journal of Mass Spectrometry 219 1 2002 115 131
40. R. Sithole, M.R. McDaniel, and L.M. Goddik Rate of Maillard browning in sweet whey powder Journal of Dairy Science 88 5 2005 1636 1645 (Pubitemid 41431213)
41. Y. Song, E.E. Babiker, M. Usui, A. Saito, and A. Kato Emulsifying properties and bactericidal action of chitosan-lysozyme conjugates Food Research International 35 5 2002 459 466 (Pubitemid 34414346)
42. Y. Sun, S. Hayakawa, S. Puangmanee, and K. Izumori Chemical properties and antioxidative activity of glycated α-lactalbumin with a rare sugar, d-allose, by Maillard reaction Food Chemistry 95 3 2006 509 517 (Pubitemid 41400229)
43. W. Sun, M. Zhao, C. Cui, Q. Zhao, and B. Yang Effect of Maillard reaction products derived from the hydrolysate of mechanically deboned chicken residue on the antioxidant, textural and sensory properties of Cantonese sausages Meat Science 86 2 2010 276 282
44. J.E. Syka, J.J. Coon, M.J. Schroeder, J. Shabanowitz, and D.F. Hunt Peptide and protein sequence analysis by electron transfer dissociation mass spectrometry Proceedings of the National Academy of Sciences of the United States of America 101 26 2004 9528 9533 (Pubitemid 38869270)
45. F. Van Lancker, A. Adams, and N. De Kimpe Formation of pyrazines in Maillard model systems of lysine-containing dipeptides Journal of Agriculture and Food Chemistry 58 4 2010 2470 2478
46. T.J. Wooster, and M.A. Augustin β-Lactoglobulin-dextran Maillard conjugates: Their effect on interfacial thickness and emulsion stability Journal of Colloid and Interface Science 303 2 2006 564 572 (Pubitemid 44547955)
47. V. Yaylayan, and P. Sporns Novel mechanisms for the decomposition of 1-(amino acid)-1-deoxy-d-fructoses (Amadori compounds): A mass spectrometric approach Food Chemistry 26 4 1987 283 305
48. V. Yaylayan, and P. Sporns Diagnostic ion series for the identification of Amadori rearrangement products by MS techniques based on electron-impact ionization Journal of Agriculture and Food Chemistry 37 4 1989 978 981
49. Y.G. Zhang, M.J. Chien, and C.-T. Ho Comparison of the volatile compounds obtained from thermal degradation of cysteine and glutathione in water Journal of Agriculture and Food Chemistry 36 5 1988 992 996
50. Q. Zhang, A. Frolov, N. Tang, R. Hoffmann, T. van de Goor, and T.O. Metz Application of electron transfer dissociation mass spectrometry in analyses of non-enzymatically glycated peptides Rapid Communications in Mass Spectrometry 21 5 2007 661 666 (Pubitemid 46340309)
51. Y.G. Zhang, and C.-T. Ho Volatile compounds formed from thermal interaction of 2,4-decadienal with cysteine and glutathione Journal of Agriculture and Food Chemistry 37 4 1989 1016 1020
52. Y.G. Zhang, and C.-T. Ho Comparison of the volatile compounds formed from the thermal reaction of glucose with cysteine and glutathione Journal of Agriculture and Food Chemistry 39 4 1991 760 763
53. Y.G. Zhang, and C.T. Ho Formation of meatlike aroma compounds from thermal reaction of inosine 5′-monophosphate with cysteine and glutathione Journal of Agriculture and Food Chemistry 39 6 1991 1145 1148
54. Q. Zhang, N. Tang, J.W. Brock, H.M. Mottaz, J.M. Ames, and J.W. Baynes Enrichment and analysis of nonenzymatically glycated peptides: boronate affinity chromatography coupled with electron-transfer dissociation mass spectrometry Journal of Proteome Research 6 6 2007 2323 2330 (Pubitemid 46985120)
55. R.A. Zubarev, D.M. Horn, E.K. Fridriksson, N.L. Kelleher, N.A. Kruger, and M.A. Lewis Electron capture dissociation for structural characterization of multiply charged protein cations Analytical Chemistry 72 3 2000 563 573 (Pubitemid 33595293)
56. R.A. Zubarev, N.L. Kelleher, and F.W. McLafferty Electron capture dissociation of multiply charged protein cations. A nonergodic process Journal of the American Chemical Society 120 13 1998 3265 3266