Mechanistic Study of Aldopentoses in the Maillard Reaction

REFERENCES

• Acquistucci , R. 2000 . Influence of Maillard reaction on protein modification and colour development in pasta. Comparison of different drying conditions . Lebensm.-Wiss. u.-Technol. , 33 : 48 – 52 . doi:10.1006/fstl.1999.0606
   Web of Science ®Google Scholar
• Al-Hakkak , J. and Kavale , S. 2002 . Improvement of emulsification properties of sodium caseinate by conjugating to pectin through the Maillard reaction . Int. Congr. Ser. , 1245 : 491 – 499 . doi:10.1016/S0531-5131(02)00887-7
   Google Scholar
• Ames , J. M. 1998 . Applications of the Maillard reaction in the food industry . Food Chem. , 62 ( 4 ) : 431 – 439 . doi:10.1016/S0308-8146(98)00078-8
   Web of Science ®Google Scholar
• Boland, M. J., Hill, J. P., Higgs, K. C., Haggarty, N. W., and Campanella, M. E. P. 2000. Process for controlling Maillard-type glycation of whey proteins and products with enhanced functional properties. WO Patent WO0018249 http://v3.espacenet.com/textdoc?DB=EPODOC&IDX=WO0018249&F=0
   Google Scholar
• Brands , C. M. J. , Alink , G. M. , van Boekel , M. A. J. S. and Jongen , W. M. F. 2000 . Mutagenicity of heated sugar-casein systems: effect of the Maillard reaction . J. Agric. Food Chem. , 48 : 2271 – 2275 . doi:10.1021/jf9907586
   PubMed Web of Science ®Google Scholar
• Brands , C. M. J. and van Boekel , M. A. J. S. 2002 . Kinetic modeling of reactions in heated monosaccharide-casein systems . J. Agric. Food Chem. , 50 : 6725 – 6739 . doi:10.1021/jf011164h
   PubMed Web of Science ®Google Scholar
• Bunn , H. F. and Higgins , P. J. 1981 . Reaction of monosaccharides with proteins: Possible evolutionary significance . Science , 213 : 222 – 224 . doi:10.1126/science.12192669
   PubMed Web of Science ®Google Scholar
• Chevalier , F. , Chobert , J.-M. , Mollé , D. and Haertlé , T. 2001a . Maillard glycation of β-lactoglobulin with several sugars: Comparative study of the properties of the obtained polymers and of the substituted sites . Lait. , 81 : 651 – 666 . doi: 10.1051/lait:2001155
   Google Scholar
• Chevalier , F. , Chobert , J.-M. , Genot , C. and Haertlé , T. 2001b . Scavenging of free radicals, antimicrobial, and cytotoxic activities of the Maillard reaction products of β-lactoglobulin glycated with several sugars . J. Agric. Food Chem. , 49 : 5031 – 5038 . doi:10.1021/jf010549x
   PubMed Web of Science ®Google Scholar
• Chevalier , F. , Chobert , J.-M. , Popineau , Y. , Nicolas , M. G. and Haertlé , T. 2001c . Improvement of functional properties of β-lactoglobulin glycated through the Maillard reaction is related to the nature of the sugar . Int. Dairy J. , 11 : 145 – 152 . doi:10.1016/S0958-6946(01)00040-1
   Web of Science ®Google Scholar
• Church , F. C. , Swaisgood , H. E. , Porter , D. H. and Catignani , G. L. 1983 . Spectrophotometric assay using o-phthaldialdehyde for determination of proteolysis in milk and isolated milk proteins . J. Dairy Sci. , 66 : 1219 – 1227 .
   Web of Science ®Google Scholar
• del Castillo , M. D. , Ferrigno , A. , Acampa , I. , Borrelli , R. C. , Olano , A. , Martínez-Rodríguez , A. and Fogliano , V. 2007 . In vitro release of angiotensin-converting enzyme inhibitors, peroxyl-radical scavengers and antibacterial compounds by enzymatic hydrolysis of glycated gluten . J. Cereal Sci. , 45 : 327 – 334 . doi:10.1016/j.jcs.2006.09.005
   Web of Science ®Google Scholar
• De Roos, K., and Wolswinkel, K. 2005. Maillard reaction compounds of cysteine and a sugar having meatlike flavour. WO Patent 2005019165 http://v3.espacenet.com/textdoc?DB=EPODOC&IDX=WO2005019165&F=0
   Google Scholar
• Desclaux , G. , Malik , T. I , Winkel , C. , Pyle , D. L. and Mottram , D. S. 2006 . Modelling the formation of Maillard reaction intermediates for the generation of flavour . Dev. Food Sci. , 43 : 367 – 370 . doi:10.1016/S0167-4501(06)80087-7
   Google Scholar
• Dubois , M. , Gilles , K. A. , Hamilton , J. K. , Rebers , P. A. and Smith , F. 1956 . Colorimetric method for determination of sugars and related substances . Anal. Chem. , 28 : 350 – 356 . doi:10.1021/ac60111a017
   Web of Science ®Google Scholar
• Einarsson , H. 1987 . The effect of time, temperature, pH and reactants on the formation of antibacterial compounds in the Maillard reaction . Lebensm.-Wiss. u.-Technol. , 20 : 51 – 55 .
   Google Scholar
• Friedman , M. 1996 . Food browning and its prevention: An overview . J. Agric. Food Chem. , 44 ( 3 ) : 631 – 653 . doi:10.1021/jf950394r
   Web of Science ®Google Scholar
• García-Baños , J. L. , del Castillo , M. D. , Sanz , M. L. , Olano , A. and Corzo , N. 2005 . Maillard reaction during storage of powder enteral formulas . Food Chem. , 89 : 555 – 560 . doi:10.1016/j.foodchem.2004.03.008
   Google Scholar
• Guérard , F. , Dufossé , L. , De La Broise , D. and Binet , A. 2001 . Enzymatic hydrolysis of proteins from yellowfin tuna (Thunnus albacares) wastes using Alcalase . J. Mol. Catal. B: Enzym. , 11 ( 4 ) : 1051 – 1059 . doi:10.1016/S1381-1177(00)00031-X
   Google Scholar
• Guérard , F. and Sumaya-Martinez , M. T. 2003 . Antioxidant effects of protein hydrolysates in the reaction with glucose . J. Am. Oil Chem. Soc. , 80 ( 5 ) : 467 – 470 . doi:10.1007/s11746-003-0721-1
   Web of Science ®Google Scholar
• Handa , A. and Kuroda , N. 1999 . Functional improvements in dried egg white through the Maillard reaction . J. Agric. Food Chem. , 47 : 1845 – 1850 . doi:10.1021/jf9811018
   PubMed Web of Science ®Google Scholar
• Hayward , L. D. and Angyal , S. J. 1977 . A symmetry rule for the circular dichroism of reducing sugars, and the proportion of carbonyl forms in aqueous solutions thereof . Carbohydr. Res. , 53 : 13 – 20 . doi:10.1016/S0008-6215(00)85450-6
   Google Scholar
• Jayathilakan , K. , Sharma , G. K. , Radhakrishna , K. and Bawa , A. S. 2007 . Antioxidant potential of synthetic and natural antioxidants and its effect on warmed-over-flavour in different species of meat . Food Chem. , 105 : 908 – 916 . doi:10.1016/j.foodchem.2007.04.068
   Web of Science ®Google Scholar
• Jiménez-Castaño , L. , Villamiel , M. , Martín-Álvarez , P. J. , Olano , A. and López-Fandiño , R. 2005 . Effect of the dry-heating conditions on the glycosylation of β-lactoglobulin with dextran through the Maillard reaction . Food Hydrocoll. , 19 : 831 – 837 . doi:10.1016/j.foodhyd.2004.10.033
   Web of Science ®Google Scholar
• Jing , H. and Kitts , D. D. 2000 . Comparison of the antioxidative and cytotoxic properties of glucose-lysine and fructose-lysine Maillard reaction products . Food Res. Int. , 33 : 509 – 516 .
   Web of Science ®Google Scholar
• Jing , H. and Kitts , D. D. 2002 . Chemical and biochemical properties of casein-sugar Maillard reaction products . Food Chem. Toxicol. , 40 : 1007 – 1015 . doi:10.1016/S0278-6915(02)00070-4
   PubMed Web of Science ®Google Scholar
• Jing , H. and Kitts , D. D. 2004 . Antioxidant activity of sugar-lysine Maillard reaction products in cell free and cell culture systems . Arch. Biochem. Biophys. , 429 : 154 – 163 . doi:10.1016/j.abb.2004.06.019
   PubMed Web of Science ®Google Scholar
• Junfeng , F. , Yanyan , Z. , Szesze , T. , Fengjuan , L. , Manyu , Z. , Saito , M. , Tatsumi , E. and Lite , L. 2006 . Improving functional properties of soy protein hydrolysate by conjugation with curdlan . J. Food Sci. , 71 ( 5 ) : C285 – C291 . doi:10.1111/j.1750-3841.2006.00035.x
   Google Scholar
• Kanatt , S. R. , Chander , R. and Sharma , A. 2008 . Chitosan glucose complex—A novel food preservative . Food Chem. , 106 : 521 – 528 . doi:10.1016/j.foodchem. 2007.06.036
   Web of Science ®Google Scholar
• Kato , Y. , Aoki , T. , Kato , N. , Nakamura , R. and Matsuda , T. 1995 . Modification of ovalbumin with glucose 6-phosphate by amino-carbonyl reaction. Improvement of protein heat stability and emulsifying activity . J. Agric. Food Chem. , 43 : 301 – 305 . doi:10.1021/jf00050a007
   Web of Science ®Google Scholar
• Lee , G.-D. and Kwon , J.-H. 1998 . The use of response surface methodology to optimize the Maillard reaction to produce melanoidins with high antioxidative and antimutagenic activities . Int. J. Food Sci. Technol. , 33 : 375 – 383 . doi:10.1046/j.1365-2621.1998.00164.x
   Web of Science ®Google Scholar
• Nakamura , S. , Ogawa , M. , Nakai , S. , Kato , A. and Kitts , D. D. 1998 . Antioxidant activity of a Maillard-type phosvitin-galactomannan conjugate with emulsifying properties and heat stability . J. Agric. Food Chem. , 46 : 3958 – 3963 . doi:10.1021/jf980292b
   Web of Science ®Google Scholar
• Rufián-Henares , J. A. and Morales , F. J. 2007 . Functional properties of melanoidins: In vitro antioxidant, antimicrobial and antihypertensive activities . Food Res. Int. , 40 : 995 – 1002 . doi:10.1016/j.foodres.2007.05.002
   Web of Science ®Google Scholar
• Shirou, H. 1986. Production of steamed Chinese noodle. JP Patent 61012259 http://v3.espacenet.com/textdoc?DB=EPODOC&IDX=JP61012259&F=0
   Google Scholar
• Sumaya-Martinez , M. T. , Thomas , S. , Linard , B. , Binet , A. and Guérard , F. 2005 . Effect of Maillard reaction conditions on browning and antiradical activity of sugar-tuna stomach hydrolysate model system . Food Res. Int. , 38 : 1045 – 1050 . doi:10.1016/j.foodres.2005.03.015
   Web of Science ®Google Scholar
• Sun , Y. , Hayakawa , S. and Izumori , K. 2004 . Modification of ovalbumin with a rare ketohexose through the Maillard reaction: Effect on protein structure and gel properties . J. Agric. Food Chem. , 52 : 1293 – 1299 . doi:10.1021/jf030428s
   PubMed Web of Science ®Google Scholar
• Sun , Y. , Hayakawa , S. , Chuamanochan , M. , Fujimoto , M. , Innun , A. and Izumori , K. 2006 . Antioxidant effects of Maillard reaction products obtained from ovalbumin and different D-aldohexoses . Biosci. Biotechnol. Biochem. , 70 ( 3 ) : 598 – 605 . doi:10.1271/bbb.70.598
   PubMed Web of Science ®Google Scholar
• Vagnarelli , P. , De Sario , A. , Cuzzoni , M. T. , Mazza , P. and De Carli , L. 1991 . Cytotoxicity and clastogenic activity of ribose-lysine browning model system . J. Agric. Food Chem. , 39 : 2237 – 2239 . doi:10.1021/jf00012a027
   Web of Science ®Google Scholar
• van Boekel , M. A. J. S. 2006 . Formation of flavour compounds in the Maillard reaction . Biotechnol. Adv. , 24 : 230 – 233 . doi:10.1016/j.biotechadv.2005.11.004
   PubMed Web of Science ®Google Scholar
• Wagner , K.-H. , Reichhold , S. , Koschutnig , K. , Chériot , S. and Billaud , C. 2007 . The potential antimutagenic and antioxidant effects of Maillard reaction products used as “natural antibrowning” agents . Mol. Nutr. Food Res. , 51 : 496 – 504 . doi:10.1002/mnfr.200600141
   PubMed Web of Science ®Google Scholar
• Yen , G.-C. and Tsai , L.-C. 1993 . Antimutagenicity of a partially fractionated Maillard reaction product . Food Chem. , 47 : 11 – 15 . doi:10.1016/0308-8146(93)90295-Q
   Web of Science ®Google Scholar