Preventive Nutrition and Food Science

The Korean Society of Food Science and Nutrition (한국식품영양과학회)
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The Effect of pH on the Antioxidative Activity of Melanoidins Formed from Glucose and Fructose with L and D-Asparagine in the Maillard Reaction

  • Kim, Ji-Sang (Department of Food and Nutrition, Kyung Hee University) ;
  • Lee, Young-Soon (Department of Food and Nutrition, Kyung Hee University)
  • Published : 2008.09.30
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Abstract

In this study, the effect of pH on the antioxidative activities of melanoidins formed as a result of the reaction between sugars, glucose (Glc) or fructose (Fru), and amino acids, L-asparagine (L-Asn) and D-asparagine (D-Asn) are examined. For this purpose, antioxidative activities were evaluated on the basis of reducing power, including ferric reducing/antioxidant power (FRAP) and free radical scavenging activity includes 1,1-diphenyl-2-picryl- hydrazil (DPPH) and 2,2'-azinobis(3-ethylbenothiazoline-6-sulfonic acid) diammonium salt (ABTS) and ferrous ion chelating activity. Ethylene diamine tetraacetate (EDTA) and trolox, a water-soluble analog of tocopherol, were used as reference antioxidant compounds. The antioxidative activities of the melanoidins at a pH of 7.0 were greater than those with a pHs of 4.0 and pH 10.0. Especially, it was found that the melanoidins formed from D-isomers are more effective antioxidants in different in vitro assays. The reducing power and chelating activity of the melanoidins formed from the Fru systems were higher than those of the melanoidins formed from the Glc systems. However, the ABTS radical scavenging activity of the melanoidins formed from the Glc systems were higher than those of the melanoidins formed from the Fru systems. In particular, the DPPH radical scavenging activity and the FRAP of the melanoidins showed different antioxidative activities according to pH level.

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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. Lingnert H, Eriksson CE. 1981. Antioxidatvie effects of Maillard reaction products. In Maillard reaction in food-chemical, physiological and technological aspects. Ericksson CE, eds. Oxford, Pergamon Press. p 453
  3. Delgado-Andrade C, Morales FJ. 2005. Unraveling the contribution of melanoidins to the antioxidant activity of coffee brews. J Agric Food Chem 53: 1403-1407 https://doi.org/10.1021/jf048500p
  4. Gomyo T, Horikoshi M. 1976. On the interaction of melanoidin with metallic ions. Agr Biol Chem 40: 33-40 https://doi.org/10.1271/bbb1961.40.33
  5. Migo VP, del Rosario EJ, Matsumura M. 1997. Flocculation of melanoidins induced by inorganic ions. J Ferment Bioeng 83: 287-291 https://doi.org/10.1016/S0922-338X(97)80994-4
  6. 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
  7. Patzold R, Nieto-Rodriguez A, Bruckner H. 2003. Chiral gas chromatographic analysis of amino acids in fortified wines. Chromatogr Suppl 57: S207-S212 https://doi.org/10.1007/BF02491718
  8. Patzold R, Brückner H. 2006. 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 Tech 223: 347-354 https://doi.org/10.1007/s00217-005-0211-y
  9. Oyaizu M. 1986. Antioxidant activity of browning products of glucosamine fractionated by organic solvent and thin-layer chromatography. J Food Sci Tech 35: 771-775
  10. 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
  11. 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
  12. 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
  13. 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
  14. Chung YC, Chang CT, Chao WW, Lin CF, Chou ST. 2002. Antioxidative activity and safety of the 50% ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1. J Agric Food Chem 50: 2454-2458 https://doi.org/10.1021/jf011369q
  15. Duh PD. 1998. Antioxidant activity of burdock (Arctium lappa Linne): its scavenging effect on free radical and active oxygen. J Am Oil Chem Soc 75: 455-461 https://doi.org/10.1007/s11746-998-0248-8
  16. 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
  17. Xing R, Liu S, Guo Z, Yu H, Li C, Ji X, Feng J, Li P. 2006. The antioxidant activity of glucosamine hydrochloride in vitro. Bioorg Med Chem 14: 1706-1709 https://doi.org/10.1016/j.bmc.2005.10.018
  18. 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
  19. 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
  20. 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
  21. Wijewickreme AN, Krejpcio Z, Kitts DD. 1999. Hydroxyl scavenging activity of glucose, fructose and ribose-lysine model Maillard products. J Food Sci 64: 457-461 https://doi.org/10.1111/j.1365-2621.1999.tb15062.x
  22. 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
  23. Haber F, Weiss J. 1934. The catalytic decomposition of hydrogen peroxide by iron salts. Proc R Soc London Ser A 147: 332-351
  24. Miller DD. 1996. Mineral. In Food chemistry. Fennema OR, ed. Marcel Dekker, New York. p 618-649
  25. Halliwell B, Gutteridge JMC. 1984. Oxygen toxicology, oxygen radicals, transition metals and disease. Biochem J 219: 1-14 https://doi.org/10.1042/bj2190001
  26. Chandrika M, Liyana P, Fereidoon S. 2007. Antioxidant and free radical scavenging activities of whole wheat and milling fractions. Food Chem 101: 1151-1157 https://doi.org/10.1016/j.foodchem.2006.03.016
  27. Miller J. 1979. Effect on growth and hemoglobin regeneration in anemic rats of interactions between glucose and minerals during heating. Nutr Rep Int 19: 679-688
  28. Ozcelik B, Lee JH, Min DB. 2003 Effect of light, oxygen, and pH on the absorbance of 2,2-diphenyl-1-picrylhydrazyl. J Food Sci 68: 487-490 https://doi.org/10.1111/j.1365-2621.2003.tb05699.x
  29. 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
  30. Del Castillo MD, Ferrigno A, Acampa I, Borrelli RC, Olano A, Martínez-Rodríguez A. 2006. In vitro release of angiotensinconverting enzyme inhibitors, peroxyl-radical scavengers and antibacterial compounds by enzymatic hydrolysis of glycated gluten. J Cereal Sci 45: 327-334 https://doi.org/10.1016/j.jcs.2006.09.005
  31. Delgado-Andrade C, Rufian-Henares JA, Morales FJ. 2005. Assessing the antioxidant activity of melanoidins from coffee brews by different antioxidant methods. J Agric Food Chem 53: 7832-7836 https://doi.org/10.1021/jf0512353
  32. Bersuder P, Hole M. 2003. Antioxidants from a heated histidine-glucose model system. In Melanoidins in food and health. Office for Official Publications of the European Communities, Luxemburg. Chapter 4, p 158-166
  33. Huang D, Ou B, Prior RL. 2005. The chemistry behind antioxidant capacity assays. J Agric Food Chem 53: 1841-1856 https://doi.org/10.1021/jf030723c
  34. Benzie IFF, Szeto YT. 1999. Total antioxidant capacity of teas by ferric reducing/antioxidant power assay. J Agric Food Chem 47: 633-636 https://doi.org/10.1021/jf9807768

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