Abstract
The Maillard reaction occurs widely in food and biological systems. This contribution reviews the relation between the Maillard reaction and food processing, particularly its contribution to flavor formation, antioxidative effects, desmutagenic activity and the improvement of protein functional properties. Proteins modified by glucose, and melanoidins are important components of foodstuffs while the reactions of amino acids or peptides with glucose or dicarbonyl compounds produce various kinds of flavor components. Melanoidins and Amadori rearrangement products play an important role in providing antioxidative effects, both in vitro and in vivo. Melanoidins also exhibit desmutagenic activity against carcinogenic compounds. Protein-polysaccharide conjugates, prepared by Maillard reaction at mild conditions, increase the emulsifying activity, as well as antioxidative and antimicrobial effects of the original proteins.
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References
Baynes, J.W.; Monnier, V.C. (Eds.) The Maillard Reaction in Aging, Diabetes, and Nutrition. Alan R. Liss. Inc.: New York, 1989.
Bedinghaus, A.J.; Ockerman, H.W. Antioxidative Maillard reaction products from reducing sugars and free amino acids in cooked ground pork patties. J. Food Sci. 1995, 60, 992–995.
Boelens, M.; van der Linde, L.M.; de Valois, P.J.; van Dort, H.M.; Takken, HJ. Organic sulfur compounds from fatty aldehydes, hydrogen sulfide, thiol and ammonia as flavor constituents. J. Agric. Food Chem. 1974, 22, 1071–1076.
Chan, R.I.M.; Stich, H.F.; Rosin, M.P.; Powrie, W.D. Antimutagenic activity of browning reaction products. Cancer Lett. 1979, 15, 27–33.
Chuyen, N.V.; Kurata, T.; Fujimaki, M. Studies on the reaction of dipeptides with glyoxal. Agric. Biol. Chem. 1973a, 37, 327–334.
Chuyen, N.V.; Kurata, T.; Fujimaki, M. On the reaction of dipeptides with dicarbonyl compounds. Agric. Biol. Chem. 1972, 36, 1257–1258.
Chuyen, N.V.; Kurata, T.; Fujimaki, M. Formation of N-[2(3-alkylpyrazin-2-on-1-yl)acyl] amino acids or peptides on heating tri- or terra peptides with glyoxal. Agric. Biol. Chem. 1973b, 37, 1613–1618.
Chuyen, N.V.; Kurata, T.; Fujimaki, M. Formation of N-carboxymethyl amino acid from the reaction of α-amino acid with glyoxal. Agric. Biol. Chem. 1973c, 37, 2209–2210.
Chuyen, N.V.; Utsunomiya, N.; Hidaka, A.; Kato, H. Antioxidative effect of Maillard reaction products in vivo. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology; Finot, P.A.; Aeschbacher, H.U.; Hurrel, R.F.; Liardon, R., Eds.; Birkhäuser Verlag: Basel, 1990; pp 285–290.
Chuyen, N.V.; Utsunomiya, N.; Kato, H. Nutritional and physiological effects of casein modified by glucose under various conditions on growing and adults rats. Agric. Biol. Chem. 1991, 55, 657–664.
Chuyen, N.V.; Ijichi, K.; Moteki, K. On the formation and scavenging of reactive oxygen species by amion-car-bonyl reaction products in model and food system. Nippon Nogeikagaku Kaishi 1996, 70, 20.
Einarson, H. The mode of action of antibacterial Maillard reaction products. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology; Finot, RA.; Aeschbacher, H.U.; Hurrel, R.F.; Liardon, R., Eds.; Birkhäuser Verlag: Basel, 1990; pp 215–220.
Eriksson, C. Maillard Reaction in Foods, Pregamon Press, Oxford, 1981.
Eiserich, J.R; Macku, C; Shibamoto, T. Volatile antioxidants formed from an L-cysteine/D-glucose Maillard model system. J. Agric. Food Chem. 1992, 40, 1982–1988.
Finot, P.A.; Aeschbacher, H.U.; Hurrel, R.F.; Liardon, R. (Eds.) 1990. The Maillard Reaction in Food Processing, Human Nutrition and Physiology, Birkhauser Verlag: Basel, 1990.
Finot, P.A. 1990. Metabolism and physiological effects of Maillard reaction products. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology; Finot, P.A.; Aeschbacher, H.U.; Hurrel, R.F.; Liardon, R., Eds.; Birkhäuser Verlag: Basel, 1990; pp 259–272.
Franzke, C; Iwainsky, H. Zur antioxydativen Wirksamkeit der Melanoidine. Dtsch. Lebensm. Rundsch. 1954, 50, 251–254
Friedman, M. Food browning and its prevention: an overview. J. Agric. Food Chem. 1996, 44, 631–653.
Fujimaki, M.; Chuyen, N.V.; Kurata, T. Studies on the decarboxylation of amino acids with glyoxal. Agric. Biol. Chem. 1971, 35, 2043–2049.
Fujimaki, M.; Namiki, M.; Kato, H. (Eds.) Amino-carbonyl Reactions in Food and Biological Systems. Kodansha, Ltd.: Tokyo, 1986.
Gomyo, T.; Horikoshi, M. On the interaction of melanoidin with metallic ions. Agric. Biol Chem. 1976, 40, 33–40.
Hayase, F.; Hirashima, S.; Okamoto, G.; Kato, H. Scavenging of active oxygens by melanoidins. Agric. Biol. Chem. 1989, 53, 3383–5.
Hiramoto, K.; Kato, T.; Kikugawa, K. Generation of DNA — breaking activity in the Maillard reaction of glucose-amino acid mixtures in a solid system. Mutat. Res. 1993, 285, 191–198.
Hirano, M.; Miura, M.; Gomyo, T. A tentative measurement of brown pigments in various processed foods. Biosci. Biotech. Biochem. 1996, 60, 877–879.
Ho, C.-T. Thermal generation of Maillard aromas. In The Maillard Reaction: Consequences for the Chemical and Life Sciences; Ikan, R., Ed.; John Wiley & Sons Ltd.: Chichester, England, 1996; pp 27–53.
Ho, C.-T.; Carlin, J.T. Formation and aroma characteristic of heterocyclic compounds in foods, In Flavor Chemistry: Trends and Developments; Teranishi, R.; Buttery, R. G.; Shahidi, F., Eds.; ACS Symp. Ser. 388, American Chemical Society: Washington D.C. 1989; pp 92–104.
Hodge, J.E. Chemistry of browning reactions in model system. J. Agric. Food Chem. 1953, 1, 928–943.
Homma, S.; Fujimaki, M. Growth response of rats fed a diet containing nondialyzable melanoidin. Prog. Food Nutr.Sci. 1983, 5, 209–216.
Hwang, H.I.; Hartman, T.G.; Rosen, R.T.; Lech, J.; Ho, C.-T. Formations of pyrazines from the Maillard reaction of glucose and lysine-α-amine-15N. J. Agric. Food Chem. 1994, 42, 1000–1004.
Hwang, H.I.; Hartman, T.G.; Ho, C-T. Relative reactivity of amino acids in pyrazine formation. J. Agric. Food Chem. 1995, 43, 179–184.
Ikan, R. (Ed.) The Maillard Reaction — Consequences for the Chemical and Life Sciences. John Wiley and Sons: Chichester, England, 1996.
Jagerstad, M.; Skog, K.; Grivas, S.; Olsson, K. Formation of heterocyclic amines using model systems. Mutat. Res. 1991, 259, 219–233.
Jackson, L.S.; Hargraves, W. A. Effects of time and temperature on the formation of MeIQx and DiMeIQx in a model system containing threonine, glucose and creatinine. J. Agric. Food Chem. 1995, 43, 1678–1694.
Kaminogawa, S.; Kumagai, Y.; Yamauchi, K.; Iwasaki, E.; Mukoyama, T.; Baba, M. Allergic skin reactivity and chemical properties of allergens in two grades of lactose. J. Food Sci. 1984, 49, 529–535.
Kato, H. Antioxidative activity of amino-carbonyl reaction products. Shokuhin Eiseigaku Zasshi. 1973, 14, 343–351.
Kato, S.; Yano, N.; Suzuki, I.; Ishi, T.; Kurata, T.; Fujimaki, M. Effect of L-cysteine on browning of egg albumin. Agric. Biol. Chem. 1974, 38, 2425–2430.
Kato, H.; Horie, T.; Fujimaki, M. Antioxidant activity of the browning oils prepared from D-glucose and L.-leucine. Nippon Eiyo Shokuryo Gakkaishi 1976, 29, 179–181.
Kato, H.; Kim, S.B.; Hayase, F.; Chuyen, N.V. Desmutagenicity of melanoidins against mutagenic pyrolysates. Agric. Biol. Chem. 1985, 49, 3093–3095.
Kato, H.; Lee, I.E.; Chuyen, N.V.; Kim, S.B.; Hayase, F. Inhibition of nitrosamine formation by nondialyzable melanoidins. Agric. Biol. Chem. 1987, 57, 1333–1338.
Kato, A.; Sasaki, Y; Furuta, R.; Kobayashi, K. Functional protein — polysaccharide conjugate prepared by controlled dry heating of ovalbumin — dextran mixture. Agric. Biol. Chem. 1990, 54, 107–112.
Kato, A.; Shimokawa, K.; Kobayashi, K. Improvement of the functional properties of insoluble gluten by pronase digestion followed by dextran conjugation. J. Agric. Food Chem. 1991, 39, 1053–1056.
Kato, A.; Mifuru, R.; Matsudomi, N; Kobayashi, K. Functional casein — polysaccharide conjugate prepared by controlled dry heating. Biosci. Biotechnol. Biochem. 1992, 56, 561–571.
Kato, A.; Minaki, K.; Kobayashi, K. Improvement of emulsifying properties of egg white proteins by the attachment of polysaccharide through Maillard reaction in dry state. J. Agric. Food Chem. 1993, 41, 540–543.
Kimiagar, M.; Lee, T. C; Chichester, C.O. Long term feeding effects of browned egg albumin to rats. J. Agric. Food Chem. 1980, 28, 150–155.
Kirigaya, N; Kato, H; Fujimaki, M. Studies on antioxidant activity of nonenzymic browning reaction products. Part I. Relations of color intensity and reductones with antioxidant activity of browning reaction products Agric. Biol. Chem. 1968, 32, 287–290.
Kirigaya, N.; Kato, H; Fujimaki, M. Studies on antioxidant activity of nonenzymic browning reaction products. Part II. Antioxidant activity of nondialyzable browning reaction products. Nippon Nogei Kagaku Zasshi. 1969, 43, 484–491.
Kurata, T; Kato, H. Formation of cooking flavor in foods. The Koryo 1981, 132, 11–26.
Labuza, T. P.; Reineccius, G. A.; Monnier, V. M.; O’Brien, J.; Baynes, J.W. (Eds.) Maillard Reactions in Chemistry, Food and Health. The Royal Society of Chemistry: Cambridge, U.K., 1994.
Lee, I.E.; Chuyen, N.V.; Hayase, F.; Kato, H. Absorption and distribution of 14C-melanoidins in rats and the desmutagenicity of absorbed melanoidins against Trp-P-1. Biosci. Biotechnol. Biochem. 1992, 56, 21–23.
Lee, I.E.; Chuyen, N.V.; Hayase, F.; Kato, H. Desmutagenicity of mlanoidins against various kinds of mutagens and activated mutagens. Biosci. Biotechnol. Biochem. 1994, 58, 21–23.
Lee, T.C.; Kim, H.J. (Eds.) Chemical Makers for Processed and Stored Foods. ACS Symp. Ser. 631, American Chemical Society: Washington D.C., 1996.
Lingnert, H.; Ericksson, C.E. Antioxidative Maillard reaction products I. Products from sugars and free amino acids. J. Food Process. Preserv. 1980a, 4, 161–172.
Lingnert, H.; Ericksson, C. E. Antioxidative Maillard reaction products II. Products from sugars and peptides or protein hydrolysates. J. Food Process. Preserv. 1980b, 4, 173–1981.
Lingnert, H. Antioxidative Maillard reaction products III. Application in cookies. J. Food Process. Preserv. 1980c, 4, 219–233.
Lingnert, H.; Lundgren, B. Antioxidative Maillard reaction products IV. Application in sausage. J. Food Process. Preserv. 1980d, 4, 235–246.
Mabrouk, A.F. Flavor of browning reaction products. In Food Taste Chemistry; Boudreau, J.C., Eds.; ACS Symp. Ser. 115, American Chemical Society: Washington D. C., 1979; pp 205–245.
Maillard, L.C. Action des acides amines sur les sucres: formation des melanoidins par voie methodologique. C. R. Acad. Sci. 1912, 154, 66–68.
Mauron, J. 1981. The Maillard reaction in food, a critical review from the nutritional stand-point. Prog. Food. Nutr. Sci. 1981, 5, 5–35.
Miura, M.; Gomyo, T. Effect of melanoidin on cholesterol in plasma, liver and feces in rats fed a high-cholesterol diet. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology; Finot, P.A.; Aeschbacher, H.U.; Hurrel, R.F.; Liardon, R., Eds.; Birkhauser Verlag: Basel, 1990; pp 291–296.
Nakamura, S.; Kato, A.; Kobayashi, K. New antimicrobial characteristics of lysozyme — dextran conjugate. J. Agric. Biol. Chem. 1991, 39, 647–650.
Nakamura, S.; Kato, A.; Kobayashi, K. Bifunctional lysozyme-galactomannan conjugate having excellent emulsifying properties and bactericidal effect. J. Agric. Food Chem. 1992a, 40, 753–739.
Nakamura, S.; Kato, A.; Kobayashi, K. Enhanced antioxidative effect of ovalbumin due to covalent binding of polysaccharides. J. Agric. Food Chem. 1992b, 40, 2033–2037.
Nakamura, S.; Kato, A.; Kobayashi, K. Role of positive charge of lysozyme in the excellent emulsifying properties of Maillard-type lysozyme-polysaccharide conjugates. J. Agric. Food Chem. 1994, 42, 2688–2691.
Oh, Y.C.; Shu, C.K.; Ho, C.-T. Some volatile compounds from thermal interaction of glucose with glycine, digly-cine, triglycine and tetraglycine. J. Agric. Food Chem. 1991, 39, 1553–1554.
Oh, Y.C.; Shu, C.K.; Ho, C.-T. Formation of novel 2(1H)-pyrazinones as peptide-specific Maillard reaction products. J. Agric. Food Chem. 1992, 40, 118–121.
Okamoto, G.; Hayase, F.; Kato, H. Scavenging of active oxygen species by glycated proteins. Biosci. Biotechnol. Biochem. 1992, 56, 928–931.
Okumura, J.; Yanai, T.; Yajima, I.; Hayashi, K. 1990. Volatile products formed from L-cysteine and dihydroxyace-tone thermally treated in different solvents. Agric. Biol. Chem. 1990, 54, 1631–1638.
Okumura, J. Volatile flavor products from Maillard reaction. Food Technol. (in Japanese) 1992, 30, 41–52.
Ohmura, H.; Tadan, N.; Shinohara, K.; Murakami, H. Formation of mutagens by the Maillard reaction. In The Maillard Reaction in Food and Nutrition; Waller, G. R.; Feather, M. S., Eds.; ACS Symp. Ser. 215, American Chemical Society: Washington D.C., 1983; pp 537–544.
Öste, R.E.; Brandon, D.L.; Bates, A.; Friedman, M. Antibody-binding to a Maillard-reacted protein. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology; Finot, RA.; Aeschbacher, H.U.; Hurrel, R.F.; Liardon, R., Eds.; Birkhauser Verlag: Basel, 1990; pp 303–308.
Rhee, C; Kim, D.H. Antioxidative activity of acetone extracts obtained from a camelization-type browning reaction. J. Food Sci. 1990, 40, 460–463.
Rizzi, G.R. Heat-induced flavor formation from peptides. In Thermal Generation of Aromas; Parliment, T.H.; McGorrin, R.J.; Ho, C.-T., Eds.; ACS Symp. Ser. 409; American Chemical Society: Washington D.C., 1989; pp 172–181.
Sakaguchi, M.; Shibamoto, T. Formation of heterocyclic compounds from the reaction of cysteamine and D-glu-cose, acetaldehyde, or glyoxal. J. Agric. Food Chem. 1978, 26, 1179–1183.
Shigematsu, H.; Shibata, S.; Kurata, T.; Kato, H.; Fujimaki, M. 5-Acetyl-2,3-dihydro-1H-pyrrolizines and 5,6,7,8-tetrahydroindilizin-8-ones, odor constituents formed on heating L-proline with D-glucose. J. Agric. Food Chem. 1975, 23, 233–237.
Shigematsu, H.; Shibata, S.; Kurata, T.; Kato, H.; Fujimaki, M. Thermal degradation products of several Amadori compounds. Agric. Biol. Chem. 1971, 41, 2377–2385.
Shu, C.K.; Lawrence, B.M. 1994. Presented at the 208th National Meeting of the American Chemical Society, Washington D.C.
Shu, Y.W.; Sahara, S.; Nakamura, S.; Kato, A. Effects of the length of polysaccharide chains on the functional properties of the Maillard-type lysozyme-polysaccharide conjugate. J. Agric. Food Chem. 1996, 44, 2544–2548.
Terasawa, N.; Murata, M.; Homma, S. Separation of model melanoidin into components with copper chelating sepharose 6B column chromatography and comparison of chelating activity. Agric. Biol. Chem. 1991, 55, 1507–1514.
Tressl, R.; Rewicki, D.; Helak, B.; Kampershröer, H.; Martin, N. Formation of 2,3-dihydro-1H-pyrrolizines as proline specific Maillard products. J. Agric. Food Chem. 1985a, 33, 919–923.
Tressl, R.; Rewicki, D.; Helak, B.; Kampershrser, H. Formation of pyrrolidines and piperidines on heating L-proline with reducing sugars. J. Agric. Food Chem. 1985b, 33, 924–928.
Tressl, R.; Helak, B.; Martin, N.; Rewicki, D. Formation of proline specific Maillard products. In Amino-carbonyl Reaction in Food and Bioloflcal Systems; Fujimaki, M.; Namiki, M.; Kato, H., Eds.; Elsevier-Kodansha: Tokyo, 1986; pp 235–244.
Utsunomiya, N.; Hayase, F.; Kato, H. Antioxidative activities of Maillard reaction products of D-glucose with ovalbumin hydrolyzed by proteases, and their synergistic effect with tocopherols. Nippon Eiyo Shokuryo Gakkaishi. 1983, 36, 461–465.
Vlassara, H.; Brownlee, M; Manogue, K.R.; Dinarells, C.A.; Pasagian, A. Cachectin / TNF and IL-1 induced by glucose-modified proteins: role in normal tissue remodeling. Sci. 1988, 240, 1546–1548.
Wakabayashi, K.; Takahashi, M.; Nagao, M.; Sato, S.; Kinae, N.; Tomita, I.; Sugimura, T. Quantification of mutagenic and carcinogenic heterocyclic amines in cooked foods. In Amino-carbonyl Reactions in Food and Biological Systems; Fujimaki, M; Namiki, M.; Kato, H., Eds.; Elsevier Kodansha, Tokyo, 1986.
Waller, G.W.; Feather, M.S. (Eds.) The Maillard in Food and Nutrition, ACS Symp. Ser. 215, American Chemical Society: Washington D.C., 1983.
Werkhoff, P.; Bruning, J.; Emberger, R.; Guntert, M.; Kopsel, M.; Kuhn, W.; Surburg, H. Isolation and characterization of volatile sulfur-containing meat flavor components in model systems. J. Agric. Food Chem. 1990, 35, 777–791.
Wells-Knecht, K.J.; Zyzak, D.V.; Litehfield, J.E.; Thorpe, S.R.; Baynes, J.W. Mechanisms of antioxidative glyco-sylation: Identification of glyoxal and arabinose as intermediates in the autooxidative modification of proteins by glucose. Biochem. 1995, 34, 3702–3709.
Yajima, M. Method of preservation and quality improvement of foodstuff. Japan Patent No. 1049789, 1979.
Yamaguchi, N.; Yokoo, Y; Koyama, Y. Studies on the browning reaction products on the stability of fats contained in biscuit and cookies. Nippon Shokuhin Kogyo Gakkaishi 1964, 11, 184–189.
Yamaguchi, N. Effect of 3-deoxy-xylosone and its browning reaction product on the stabilities of fat and oil. Nippon Shokuhin Kogyo Gakkaishi 1969, 16, 94–96.
Yamaguchi, N.; Fujimaki, M. Studies on browning reaction products from reducing sugars and amino acids. Antioxidative activity of purified melanoidins and their comparison with those of legal antioxidants. Nippon Shokuhin Kogyo Gakkaishi 1974, 21, 6–12.
Yamaguchi, N.; Koyama, Y; Fujimaki, M. Fractionation and antioxidative activity of browning reaction products between D-xylose and glycine. Prog. Food Nutr. Sci. 1981, 5, 429–439.
Yamaguchi, N. Antioxidative effect of decolorized melanoidin. New Food Industry (in Japanese) 1991, 33, 76–80.
Yen, G.C.; Tsai, L.C.; Lii, J.D. Antimutagenic effect of Maillard browning products obtained from amino acids and sugars. Food Chem. Toxicol. 1992, 30, 127–132.
Yen, G.C.; Lii, J.D. Influence of the reaction conditions on the antimutagenic effect of Maillard reaction products derived from xylose and lysine. J. Agric. Food Chem. 1992a, 40, 1034–1037.
Yen, G.C.; Lii, J.D. Antimutagenic effect of Maillard reaction products prepared from glucose and tryptophan. J. Food Prot. 1992b, 55, 615–619.
Yen, G.C.; Tsai, L.C. Antimutagenic of a partially fractionated Maillard reaction product. Food Chem. 1993, 47, 11–15.
Yen, G.C.; Hsieh, P.P. Possible mechanisms of antimutagenic effect of Maillard reaction products prepared from xylose and glycine. J. Agric. Food Chem. 1994, 42, 133–137.
Yen, G.C.; Hsieh, P.P. Antioxidative activity and scavenging effects on active oxygen of xylose — lysine Maillard reaction products. J. Sci. Food Agric. 1995, 67, 415–420.
Yu, T.H.; Ho, C.-T. 1995. Volatile compounds generated from thermal reaction of methionine and methionine sulfoxide with or without glucose. J. Agric. Food Chem. 1995, 43, 1641–1646.
Zhang, Y; Ho, C.-T. Comparison of the volatile compounds formed from the thermal reaction of glucose with cysteine and glutathione. J. Agric. Food Chem. 1991, 39, 760–763.
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Chuyen, N.V. (1998). Maillard Reaction and Food Processing. In: Shahidi, F., Ho, CT., van Chuyen, N. (eds) Process-Induced Chemical Changes in Food. Advances in Experimental Medicine and Biology, vol 434. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1925-0_18
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