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Characteristics and antioxidant activity of Maillard reaction products from fructose-glycine oligomer

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Abstract

The pH of Maillard reaction products (MRPs) derived from the Gly model system (Gly) decreased markedly as heating time increased. However the Digly model system (Digly) exhibited the highest increase in absorbance at 294 and 420 nm. Moreover, the loss of fructose and degree of sugar enolization in MRPs derived from the Trigly model system (Trigly) was the highest, whereas the glycine oligomer content in the Digly noticeably decreased as heating time increased. Furthermore, the gel permeation chromatograms (GPC) patterns of all MRP samples exhibited rising intensities as a function of the heating time, whereas the major peaks of each MRP sample were eluted at different retention times as glycine oligomer. Antioxidant activity of each MRP sample was investigated by Fe2+ and Cu2+ chelating activity, Trolox, ABTS, 1,1-diphenyl-2-picryl-hydrazil (DPPH) radical scavenging activity, and ferric reducing ability of plasma (FRAP) assay. MRPs derived from the glycine oligomer were found to be effective antioxidants in different antioxidant activity assays.

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References

  1. Hodge JE. Chemistry of browning reactions in model systems. J. Agr. Food Chem. 1: 928–934 (1953)

    Article  CAS  Google Scholar 

  2. Wijewickreme AN, Kitts DD, Durance TD. Reaction conditions influence the elementary composition and metal chelating affinity of nondialyzable model Maillard reaction products. J. Agr. Food Chem. 45: 4577–4583 (1997)

    Article  CAS  Google Scholar 

  3. Eichner K. Antioxidant effect of Maillard reaction intermediates. Prog. Food. Nutr. Sci. 5: 441–451 (1981)

    CAS  Google Scholar 

  4. Morales FJ, Jimenez-Perez S. Free radical scavenging capacity of Maillard reaction products as related to color and fluorescence. Food Chem. 72: 119–125 (2001)

    Article  CAS  Google Scholar 

  5. Bersuder P, Hole M, Smith G. Antioxidants from a heated histidine-glucose model system. Investigation of the copper (II) binding ability. J. Am. Oil Chem. Soc. 78: 1079–1082 (2001)

    Article  CAS  Google Scholar 

  6. Bevers HAJM, Wijntje R, De Haan AB. Analysis of fructose, glycine, and triglycine using HPLC UV-vis detection and evaporative light-scattering detection. Spectroscopy 21: 52–61 (2006)

    CAS  Google Scholar 

  7. Hartman R, Meisel H. Food-derived peptides with biological activity: From research to food applications. Curr. Opin. Biotech. 18: 163–169 (2007)

    Article  Google Scholar 

  8. Lu CY, Hao Z, Payne R, Ho CT. Effects of water content on volatile generation and peptide degradation in the Maillard reaction of glycine, diglycine, and triglycine. J. Agr. Food Chem. 53: 6443–6447 (2005)

    Article  CAS  Google Scholar 

  9. Oh YC, Shu CK, Ho CT. Some volatiles compounds formed from thermal interaction of glucose with glycine, diglycine, triglycine, and tetraglycine. J. Agr. Food Chem. 39: 1553–1554 (1991)

    Article  CAS  Google Scholar 

  10. Budavari S, O’Neil MJ, Smith A, Heckelman PE, Kinneary JF. The Merck Index. 12th ed. Merck & Co., Whitehouse Station, NJ, USA. pp. 1477–1478 (1996)

    Google Scholar 

  11. Ajandouz EH, Tchiakpe LS, Ore FD, Benajiba A, Puigserver A. Effects of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. J. Food Sci. 66: 926–931 (2001)

    Article  CAS  Google Scholar 

  12. Wang L, Xiong YL. Inhibition of lipid oxidation in cooked beef patties by hydrolyzed potato protein is related to its reducing and radical scavenging ability. J. Agr. Food Chem. 53: 9186–9192 (2005)

    Article  CAS  Google Scholar 

  13. Dinis TCP, Madeira VMC, Almerida LM. Action of phenolic derivatives (acetoaminophen, salycilate, and 5-aminosalycilate) as inhibitors of membrane lipid peroxidation and as peroxyl radical scavenges. Arch. Biochem. Biophys. 315: 161–169 (1994)

    Article  CAS  Google Scholar 

  14. Yen GC, Hsieh PP. Antioxidative activity and scavenging effects on xylose-lysine Maillard reaction products. J. Sci. Food Agr. 67: 415–420 (1995)

    Article  CAS  Google Scholar 

  15. Benzie IFF, Strain JJ. The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power the FRAP assay. Anal. Biochem. 239: 70–76 (1996)

    Article  CAS  Google Scholar 

  16. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Bio. Med. 26: 1231–1237 (1999)

    Article  CAS  Google Scholar 

  17. Benjakul S, Lertittikul W, Bauer F. Antioxidant activity of Maillard reaction products from a porcine plasma protein-sugar model system. Food Chem. 93: 189–196 (2005)

    Article  CAS  Google Scholar 

  18. Kim JS, Lee YS. Antioxidant activity of Maillard reaction products derived from aqueous glucose/glycine, diglycine, and triglycine model systems as a function of heating time. Food Chem. 116: 227–232 (2009)

    Article  CAS  Google Scholar 

  19. Kim JS, Lee YS. Study of Maillard reaction products derived from aqueous model systems with different peptide chain lengths. Food Chem. 116: 846–853 (2009)

    Article  CAS  Google Scholar 

  20. Ogura K, Nakayama M, Nakaoka K, Nishihata Y. Spectro-electrochemical and EQCM studies on the oxidation of glycilpeptides in alkaline medium. J. Electroanal. Chem. 482: 32–39 (2000)

    Article  CAS  Google Scholar 

  21. Huber C, Wachtershauser G. Peptides by activation of amino acids with CO on (Ni, Fe)S surfaces: Implications for the origin of life. Science 281: 670–671 (1998)

    Article  CAS  Google Scholar 

  22. Chuyen NV, Kurata T, Fujimaki M. Studies on the reaction of dipeptides with glyoxal. Agr. Biol. Chem. Tokyo 37: 327–334 (1973)

    Google Scholar 

  23. Reynols TM. Non-enzymatic browning. Sugar-amine interaction. p. 219. In: Carbohydrates and Their Roles. Shultz HW (ed). AVI Pub. Co., Westport, CT, USA (1969)

    Google Scholar 

  24. Buera MDP, Chirife J, Resnik SL, Lozano RD. Nonenzymatic browning in liquid model systems of high water activity: Kinetics of color changes due to reaction between glucose and glycine peptides. J. Food Sci. 52: 1059–1062 (1987)

    Article  Google Scholar 

  25. Maillard LC, Gautier MA. The reaction of amino acids with sugars: Mechanisms of melanoid formation. C. R. Seances Acad. Sci. III 154: 66–68 (1912)

    CAS  Google Scholar 

  26. Reynolds TM. Chemistry of nonenzymic browning II. Adv. Food Res. 14: 167–283 (1965)

    CAS  Google Scholar 

  27. Mauron J. The Maillard reaction in food: A critical review from the nutritional standpoint. Prog. Food. Nutr. Sci. 5: 5–35 (1981)

    CAS  Google Scholar 

  28. Shin DB, Hayase F, Kato H. Polymerization of proteins caused by reaction with sugars and the formation of 3-deoxyglucosone under physiological conditions. Agr. Biol. Chem. Tokyo 52: 1451–1458 (1988)

    CAS  Google Scholar 

  29. Burton HS, McWeeny DJ, Biltcliffe DO. Sulphur dioxide and ketose-amino reactions. Chem. Indust. 27: 693–695 (1963)

    Google Scholar 

  30. Reynolds TM. Chemistry of nonenzymic browning. III. Effect of bisulphite, phosphate, and malate on the reaction of glycine and glucose. Aust. J. Chem. 12: 265–274 (1959)

    Article  CAS  Google Scholar 

  31. Suárez G, Maturana J, Oronsky AL, Raventós-Suárez C. Fructose induced fluoresence generation of reductively methylated glycated bovine serum albumin: Evidence for nonenzymatic glycation of Amadori adducts. Biochim. Biophys. Acta 1075: 12–19 (1991)

    Google Scholar 

  32. Ivanov CP, Ivanov OC, Simeonova RA, Mirkova GD. A study of the interaction of glycine and its oligohomopeptides with formaldehyde and acetaldehyde under possible primitive earth conditions. Origins Life Evol. B 13: 97–108 (1983)

    Article  CAS  Google Scholar 

  33. Brands CMJ, Van Boekel MAJS. Reactions of monosaccharides during heating of sugar-casein systems: Building of a reaction network model. J. Agr. Food Chem. 49: 4667–4675 (2001)

    Article  CAS  Google Scholar 

  34. De Kok PMT, Rosing EAE. Reactivity of peptides in Maillard reaction. pp. 158–179. In: Thermally Generated Flavors: Maillard, Microwave, and Extrusion Processes. Parliment TH, Morello MJ, McGomn RJ (eds). American Chemical Society, Washington, DC, USA (1994)

    Google Scholar 

  35. Van Boekel MAJS. Kinetic modelling of sugar reactions in heated milk-like systems. Neth. Milk Dairy J. 50: 245–266 (1996)

    Google Scholar 

  36. Kim JS, Lee YS. Effect of reaction pH on enolization and racemization reactions of glucose and fructose on heating with amino acid enantiomers and formation of melanoidins as result of the Maillard reaction. Food Chem. 108: 582–592 (2008)

    Article  CAS  Google Scholar 

  37. Nagayama M, Takaoka O, Inomata K, Yamagata Y. Diketopiperazine-mediated peptide formation in aqueous solution. Origins Life Evol. B 20: 249–257 (1990)

    Article  CAS  Google Scholar 

  38. Imai E, Honda H, Hatori K, Brack A, Matsuno K. Elongation of oligopeptides in a simulated submarine hydrothermal system. Science 283: 831–833 (1990)

    Article  Google Scholar 

  39. Hofmann T. Studies on the relationship between Mw and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentrifugation and color dilution techniques. J. Agr. Food Chem. 46: 3891–3895 (1998)

    Article  CAS  Google Scholar 

  40. Delgado-Andrade C, Seiquer I, Navarro P. Bioavailability of iron from a heat treated glucose-lysine model food system: Assays in rats and in Caco-2 cells. J. Sci. Food Agr. 84: 1507–1513 (2004)

    Article  CAS  Google Scholar 

  41. Jing H, Kitts DD. Antioxidant activity of sugar-lysine Maillard reaction products in cell free and cell culture systems. Arch. Biochem. Biophys. 429: 154–163 (2004)

    Article  CAS  Google Scholar 

  42. Yoshimura Y, Ujima T, Watanabe T, Nakazawa H. Antioxidative effect of Maillard reaction products using glucose-glycine model system. J. Agr. Food Chem. 45: 4106–4109 (1997)

    Article  CAS  Google Scholar 

  43. Morales FJ, Fernandez-Fraguas C, Jiménez-Pérez S. Iron binding ability of melanoidins from food and model systems. Food Chem. 90: 821–827 (2005)

    Article  CAS  Google Scholar 

  44. O’Brien JO, Morrissey PA. Metal ion complexation by products of the Maillard reaction. Food Chem. 58: 17–27 (1997)

    Article  Google Scholar 

  45. Seifert ST, Krause RM, Gloe K, Henle T. Metal complexation by the peptide-bound maillard reaction products N(ɛ)-fructoselysine and N(ɛ)-carboxymethyllysine. J. Agr. Food Chem. 52: 2347–2350 (2004)

    Article  CAS  Google Scholar 

  46. Wijewickreme AN, Kitts DD. Metal chelating and antioxidant activity of model Maillard reaction products. Adv. Exp. Med. Biol. 36: 543–553 (1998)

    CAS  Google Scholar 

  47. Shon MY, Kim TH, Sung NJ. Antioxidants and free radical scavenging activity of Phellinus baumii extracts. Food Chem. 82: 593–597 (2003)

    Article  CAS  Google Scholar 

  48. Shih PW, Lai PL, Jen HWK. Antioxidant activities of aqueous extracts of selected plants. Food Chem. 99: 775–783 (2006)

    Article  Google Scholar 

  49. Chen HM, Muramoto K, Yamauchi F, Fujimoto K, Nokihara K. Antioxidant properties of histidine-containing peptides designed from peptide fragment found in the digests of a soybean protein. J. Agr. Food Chem. 46: 49–53 (1998)

    Article  CAS  Google Scholar 

  50. Zhou S, Decker EA. Ability of amino acids, dipeptides, polyamines, and sulfhydryls to quench hexanal, a saturated aldehydic lipid oxidation product. J. Agr. Food Chem. 47: 1932–1936 (1999)

    Article  CAS  Google Scholar 

  51. Yamaguchi N, Yokoo Y, Fujimaki M. Studies on antioxidative activities of amino compounds on fats and oils. Part II. Antioxidative activities of dipeptides and their synergistic effects on tocopherol. Nippon Shokuhin Kogyo Gakk. 22: 425–430 (1975)

    Google Scholar 

  52. Wu HC, Chen HM, Shiau CY. Free amino acids and peptides as related to antioxidant properties in protein hydrolysates of mackerel (Scomber austriasicus). Food Res. Int. 36: 949–957 (2003)

    Article  CAS  Google Scholar 

  53. Rufián-Henares JA, Morales FJ. Functional properties of melanoidins: In vitro antioxidant, antimicrobial, and antihypertensive activities. Food Res. Int. 40: 995–1002 (2007)

    Article  Google Scholar 

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Kim, JS., Lee, YS. Characteristics and antioxidant activity of Maillard reaction products from fructose-glycine oligomer. Food Sci Biotechnol 19, 929–940 (2010). https://doi.org/10.1007/s10068-010-0131-x

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