Preventive Nutrition and Food Science

The Korean Society of Food Science and Nutrition (한국식품영양과학회)
권호 표지
DOI QR코드

DOI QR Code

Influence of the pH and Enantiomer on the Antioxidant Activity of Maillard Reaction Mixture Solution in the Model Systems

  • Kim, Ji-Sang (Department of Food and Nutritional Science, Kyungnam University)
  • Received : 2010.09.03
  • Accepted : 2010.11.22
  • Published : 2010.12.31
Download PDF
⟨ Previous Next ⟩

Abstract

This study was designed to investigate the influence of the pH and enantiomer on the antioxidant activity of Maillard reaction mixture solution in model systems. The loss of glucose in MRPs did not show different characteristics for the different amino acid enantiomers; however, the concentration of glucose decreased as the pH levels increased. The enolization of sugars was observed in all MRP samples according to increase of pH levels. In addition, D-amino acids were detected in L-amino acid systems and L-amino acids could also be observed in D-amino acid systems. Formation of the isomer was the highest in the Glc/L-Lys system. The browning development increased as pH levels increased; however, browning development did not show different characteristics based on the use of L- versus D-isomers of the same amino acid. The L- and D-isomers show different absorption values in the UV-Vis spectra, but the absorption patterns display a similar shape. The antioxidant activities of MRPs derived from the Glc/Gly, Glc/L-Asn and Glc/D-Asn systems at pH 7.0 were greater compared to those of pH 4.0 and pH 10.0. The antioxidant activities of MRPs derived from the Glc/L-Lys and Glc/D-Lys systems decreased as the pH increased. In addition, the results show that the MRPs derived from the D-isomers have similar antioxidant activities as those from L-isomer. Therefore, the MRPs have the different antioxidant activities on the basis of the pH level, but not on the basis of different amino acid enantiomers.

Keywords

References

  1. Wijewickreme AN, Kitts DD, Durance TD. 1997. Reaction conditions influence the elementary composition and metal chelating affinity of nondialyzable model Maillard reaction products. J Agric Food Chem 45: 4577-4583. https://doi.org/10.1021/jf970041n
  2. Baxter JH. 1995. Free amino acid stability in reducing sugar systems. J Food Sci 60: 405-407. https://doi.org/10.1111/j.1365-2621.1995.tb05682.x
  3. Ashoor SH, Zent JB. 1984. Maillard browning of common amino acids and sugars. J Food Sci 49: 1206-1207. https://doi.org/10.1111/j.1365-2621.1984.tb10432.x
  4. Naranjo GB, Malec LS, Vigo MS. 1998. Reducing sugars effect on available lysine loss of casein by moderate heat treatment. Food Chem 62: 309-313. https://doi.org/10.1016/S0308-8146(97)00176-3
  5. Tanaka M, Chiba N, Ishizaki S, Takai R, Taguchi T. 1994. Influence of water activity and Maillard reaction on the polymerization of myosin heavy chain in freeze-dried squid meat. Fisheries Sci 60: 607-611. https://doi.org/10.2331/fishsci.60.607
  6. Yoshimura Y, Ujima T, Watanabe T, Nakazawa H. 1997. Antioxidative effect of Maillard reaction products using glucose-glycine model system. J Agric Food Chem 45: 4106-4109. https://doi.org/10.1021/jf9609845
  7. Yen GC, Hsieh PP. 1995. Antioxidative activity and scavenging effects on xylose-lysine Maillard reaction products. J Sci Food Agr 67: 415-420. https://doi.org/10.1002/jsfa.2740670320
  8. Friedman M. 1999. Chemistry, nutrition, and microbiology of D-amino acids. J Agric Food Chem 47: 3457-3479. https://doi.org/10.1021/jf990080u
  9. Bruckner H, Justus J, Kirschbaum J. 2001. Saccharide induced racemization of amino acids in the course of the Maillard reaction. Amino Acids 21: 429-433. https://doi.org/10.1007/s007260170007
  10. Ledl F, Schleicher E. 1990. New aspects of the Maillard reaction in foods and in the human body. Angew Chem Int Ed 29: 565-594. https://doi.org/10.1002/anie.199005653
  11. Patzold R, Bruckner H. 2005. Mass spectrometric detection and formation of D-amino acids in processed plant saps, syrups, and fruit juice concentrates. J Agric Food Chem 53: 9722-9729. https://doi.org/10.1021/jf051433u
  12. Patzold R, Bruckner H. 2006a. Gas chromatographic detection of D-amino acids in natural and thermally treated bee honeys and studies on the mechanism of their formation as result of the Maillard reaction. Eur Food Res Technol 223: 347-354. https://doi.org/10.1007/s00217-005-0211-y
  13. Patzold R, Bruckner H. 2006b. Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and other cocoa products. Amino Acids 31: 63-72. https://doi.org/10.1007/s00726-006-0330-1
  14. Bada JL. 1972. Kinetics of racemization of amino acids as a function of pH. J Am Chem Soc 94: 1371-1373. https://doi.org/10.1021/ja00759a064
  15. Bailey JR, Ames JM, Monti SM. 1996. An analysis of the non-volatile reaction products of aqueous Maillard model system at pH 5, using reversed-phase HPLC with diode-array detection. J Sci Food Agr 72: 97-103. https://doi.org/10.1002/(SICI)1097-0010(199609)72:1<97::AID-JSFA626>3.0.CO;2-Q
  16. Marfey P. 1984. Determination of D-amino acids. II. Use of a bifunctional reagent, 1,5-difluoro-2,4-dinitrobenzene. Carlsberg Res Commun 49: 591-596. https://doi.org/10.1007/BF02908688
  17. Dinis TCP, Madeira VMC, Almerida LM. 1994. 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. https://doi.org/10.1006/abbi.1994.1485
  18. Benzie IFF, Strain JJ. 1996. The ferric reducing ability of plasma (FRAP) as a measure of antioxidant power the FRAP assay. Anal Biochem 239: 70-76. https://doi.org/10.1006/abio.1996.0292
  19. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radic Biol Med 26: 1231-1237. https://doi.org/10.1016/S0891-5849(98)00315-3
  20. Speck JCJ. 1958. The Lobry de Bruyn-Alberda van Ekenstein transformation. Adv Carbohydr Chem 13: 63-103.
  21. Ajandouz EH, Puigserver A. 1999. Nonenzymatic browning reaction of essential amino acids: Effect of pH on caramelization and Maillard reaction kinetics. J Agric Food Chem 47: 1786-1793. https://doi.org/10.1021/jf980928z
  22. Ajandouz EH, Tchiakpe LS, DalleOre F, Benajiba A, Puigserver A. 2001. Effect of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. J Food Sci 66: 926-931. https://doi.org/10.1111/j.1365-2621.2001.tb08213.x
  23. Benjakul S, Visessanguan W, Phongkanpai V, Tanaka M. 2005. Antioxidative activity of caramelisation products and their preventive effect on lipid oxidation in fish mince. Food Chem 90: 231-239. https://doi.org/10.1016/j.foodchem.2004.03.045
  24. Van Boekel MAJS. 1996. Kinetic modelling of sugar reactions in heated milk-like systems. Neth Milk Dairy J 50: 245-266.
  25. Friedman M. 1996. Food browning and its prevention: an overview. J Agric Food Chem 44: 631-653. https://doi.org/10.1021/jf950394r
  26. Patzold R, Bruckner H. 2004. Mechanistische aspekte und konsequenzen der bildung von D-aminosauren im laufe der Maillardreaktion. Lebensmittelchemie 58: 100.
  27. Casal S, Mendes E, Oliveira MBPP, Ferreira MA. 2005. Roast effects on coffee amino acid enantiomers. Food Chem 89: 333-340. https://doi.org/10.1016/j.foodchem.2004.02.039
  28. Kutz N, Patzold R, Bruckner H. 2004. Bestimmung von Aminosaureenantiomeren in Kakao und Kakaoprodukten. Lebensmittelchemie 58: 106-107.
  29. Morales FJ, Jimenez-Perez S. 2001. Free radical scavenging capacity of Maillard reaction products as related to colour and fluorescence. Food Chem 72: 119-125. https://doi.org/10.1016/S0308-8146(00)00239-9
  30. Hofmann T. 1998. Studies on the relationship between molecular weight and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentifugation and color dilution techniques. J Agric Food Chem 46: 3891-3895. https://doi.org/10.1021/jf980397e
  31. Brands C, Wedzicha B, Van Boekel MAJS. 2002. Quantification of melanoidin concentration in sugar-casein systems. J Agric Food Chem 50: 1178-1183. https://doi.org/10.1021/jf010789c
  32. Guimaraes C, Bento LSM, Mota M. 1996. A study of sugar colourants through ion exchange and salt regeneration. Int Sugar J 98: 584-587.
  33. Rafik M, Mas A, Elharfi A, Schue F. 1997. Decoloration de solutions sucrees par ultrafiltration sur une membrane a base de poly(organocyclophosphazene). Eur Polymer J 33: 679-690. https://doi.org/10.1016/S0014-3057(96)00232-7
  34. Delgado-Andrade C, Seiquer I, Navarro P. 2004. 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. https://doi.org/10.1002/jsfa.1839
  35. Jing H, Kitts DD. 2004. Antioxidant activity of sugarlysine Maillard reaction products in cell free and cell culture systems. Arch Biochem Biophys 429: 154-163. https://doi.org/10.1016/j.abb.2004.06.019
  36. O'Brien JO, Morrissey PA. 1997. Metal ion complexation by products of the Maillard reaction. Food Chem 58: 17-27. https://doi.org/10.1016/S0308-8146(96)00162-8
  37. Morales FJ, Fernandez-Fraguas C, Jimenez-Perez S. 2005. Iron binding ability of melanoidins from food and model systems. Food Chem 90: 821-827. https://doi.org/10.1016/j.foodchem.2004.05.030
  38. Delgado-Andrade C, Seiquer I, Nieto R, Navarro P. 2004. Effects of heated glucose-lysine and glucose-methionine model-systems on mineral solubility. Food Chem 87: 329-337. https://doi.org/10.1016/j.foodchem.2003.12.002
  39. Shon MY, Kim TH, Sung NJ. 2003. Antioxidants and free radical scavenging activity of Phellinus baumii extracts. Food Chem 82: 593-597. https://doi.org/10.1016/S0308-8146(03)00015-3
  40. Shih PW, Lai PL, Jen HWK. 2006. Antioxidant activities of aqueous extracts of selected plants. Food Chem 99: 775-783. https://doi.org/10.1016/j.foodchem.2005.07.058
  41. Benjakul S, Lertittikul W, Bauer F. 2005. Antioxidant activity of Maillard reaction products from a porcine plasma protein-sugar model system. Food Chem 93: 189-196. https://doi.org/10.1016/j.foodchem.2004.10.019
  42. Bersuder P, Hole M. 2003. Melanoidins in food and health. Office for Official Publications of the European Communities, Luxemburg. Chapter 4, p 158-166.
  43. Gao X, Bjork L, Trajkovski V, Uggla M. 2000. Evaluation of antioxidant activities of rosehip ethanol extracts in different test systems. J Sci Food Agr 80: 2021-2027. https://doi.org/10.1002/1097-0010(200011)80:14<2021::AID-JSFA745>3.0.CO;2-2
  44. Rufian-Henares JA, Morales FJ. 2007. Functional properties of melanoidins: In vitro antioxidant, antimicrobial and antihypertensive activities. Food Res Int 40: 995-1002. https://doi.org/10.1016/j.foodres.2007.05.002
  45. Hwang JY, Shue YS, Chang HM. 2001. Antioxidative activity of roasted and defatted peanut kernels. Food Res Int 34: 639-647. https://doi.org/10.1016/S0963-9969(01)00083-7
  46. Charurin P, Ames JM, Castiello MD. 2002. Antioxidant activity of coffee model systems. J Agric Food Chem 50: 3751-3756. https://doi.org/10.1021/jf011703i
  47. Eichner K. 1981. Antioxidant effect of Maillard reaction intermediates. Prog Food Nutr Sci 5: 441-451.
  48. Miller DD. 1996. Mineral. In Food Chemistry. Fennema OR, ed. Marcel Dekker, New York, USA. p 618-649.
  49. Prior RL, Wu X, Schaich K. 2005. Standardized method for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J Agric Food Chem 53: 4290-4302. https://doi.org/10.1021/jf0502698

Cited by

  1. Antioxidant and antibacterial activities of modified crab shell bioactive peptides by Maillard reaction vol.21, pp.1, 2018, https://doi.org/10.1080/10942912.2018.1561463