Biological Properties of Melanoidins: A Review

REFERENCES

• Martins , S. , Jongen , W. and Van Boekel , M. 2000 . A review of Maillard reaction in food and implication to kinetic modeling . Trends in Food Science and Technology , 11 : 364 – 373 .
   Web of Science ®Google Scholar
• Yaylayan , V.A. and Kaminsky , E. 1998 . Isolation and structural analysis of Maillard polymers: Caramel and melanoidin formation in glycine/glucose model system . Food Chemistry , 63 : 25 – 31 .
   Web of Science ®Google Scholar
• Morales , F.J. 2002 . Application of capillary zone electrophoresis to the study of food and food-model melanoidins . Food Chemistry , 76 : 363 – 369 .
   Web of Science ®Google Scholar
• Rufián-Henares , J.A. and Morales , F.J. 2008 . Antimicrobial activity of melanoidins against Escherichia coli is mediated by a membrane damage mechanism . Journal of Agricultural and Food Chemistry , 56 : 2357 – 2362 .
   PubMed Web of Science ®Google Scholar
• Bekedam , E.K. , Roos , E. , Schols , H.A. , Van Boekel , M.A.J.S. and Smit , G. 2008 . Low molecular weight melanoidins in coffee brew . Journal of Agricultural and Food Chemistry , 56 : 4060 – 4067 .
   PubMed Web of Science ®Google Scholar
• Silvan , J.M. , van , de Lagemaat , J. , Olano , A. and Del Castilo , M.D. 2006 . Analysis and biological properties of amino acid derivates formed by Maillard reaction in foods . Journal of Pharmaceutical and Biomedical Analysis , 41 : 1543 – 1551 .
   PubMed Web of Science ®Google Scholar
• Friedman , M. 1996 . Food browning and its prevention: An overview . Journal of Agricultural and Food Chemistry , 44 : 631 – 653 .
   Web of Science ®Google Scholar
• Nunes , F.M. and Coimbra , M.A. 2010 . Role of hydroxycinnamates in coffee melanoidin formation . Phytochemical Review , 9 : 171 – 185 .
   Web of Science ®Google Scholar
• Rufián-Henares , J.A. and de la Cueva , S.P. 2009 . Antimicrobial activity of coffee melanoidins. A study of their metal-chelating properties . Journal of Agricultural and Food Chemistry , 57 : 432 – 438 .
   PubMed Web of Science ®Google Scholar
• Fogliano , V. and Morales , F.J. 2001 . Estimation of dietary intake of melanoidins from coffee and bread . Food and Function , 2 : 117 – 123 .
   Web of Science ®Google Scholar
• Van Boekel , M.A.J.S. 2006 . Formation of flavour compounds in the Maillard reaction . Biotechnology Advances , 24 : 230 – 233 .
   PubMed Web of Science ®Google Scholar
• Ames , J. , Caemmerer , B. , Velisek , J. , Cejpek , K. , Obretenov , C. and Cioroi , M. 2000 . The nature of melanoidins and their investigation. Melanoidins in food and health . Melanoidins in food and health , 1 : 13 – 29 .
   Google Scholar
• Erbersdobler , H.F. and Somoza , V. 2007 . Forty years of furosine—Forty years of using Maillard reaction products as indicators of the nutritional quality of foods . Molecular Nutrition and Food Research , 51 : 423 – 430 .
   PubMed Web of Science ®Google Scholar
• Morales , F.J. , Somoza , V. and Fogliano , V. 2010 . “ Physiological relevance of dietary melanoidins ” . In Amino Acids DOI: 10.1007/s00726-010-0774-1.
   Google Scholar
• Nunes , F.M. and Coimbra , M.A. 2007 . Melanoidins from coffee infusions. Fractionation, chemical characterization, and effect of the degree of roast . Journal of Agricultural and Food Chemistry , 55 : 3967 – 3977 .
   PubMed Web of Science ®Google Scholar
• Bekedam , E.K. , Loots , M.J. , Schols , H.A. , Van Boekel , M.A.J.S. and Smit , G. 2008 . Roasting effects on formation mechanisms of coffee brew melanoidins . Journal of Agricultural and Food Chemistry , 56 : 7138 – 7145 .
   PubMed Web of Science ®Google Scholar
• Argirova , M.D. 2005 . Photosensitizer activity of model melanoidins . Journal of Agricultural and Food Chemistry , 53 : 1210 – 1214 .
   PubMed Web of Science ®Google Scholar
• Rufián-Henares , J.A. and Morales , F.J. 2007 . Effect of in vitro enzymatic digestion on antioxidant activity of coffee melanoidins and fractions . Journal of Agricultural and Food Chemistry , 55 : 10016 – 10021 .
   PubMed Web of Science ®Google Scholar
• Rivero , D. , Perez-Magarino , S. , Gonzalez-Sanjose , M.L. , Valls-Belles , V. , Codoner , P. and Muniz , P. 2005 . Inhibition of induced DNA oxidative damage by beers: Correlation with the content of polyphenols and melanoidins . Journal of Agricultural and Food Chemistry , 53 : 3637 – 3642 .
   PubMed Web of Science ®Google Scholar
• Kuntcheva , M.J. and Obretenov , T.D. 1996 . Isolation and characterization of melanoidins from beer . European Food Research and Technology , 202 : 238 – 243 .
   Google Scholar
• González-Mateo , S. , González-Sanjosé , M.L. and Muńiz , P. 2009 . Presence of Maillard products in Spanish muffins and evaluation of colour and antioxidant potential . Food and Chemical Toxicology , 47 : 2798 – 2805 .
   PubMed Web of Science ®Google Scholar
• Borrelli , R.C. and Fogliano , V. 2005 . Bread crust melanoidins as potential prebiotic ingredients . Molecular Nutrition and Food Research , 49 : 673 – 678 .
   PubMed Web of Science ®Google Scholar
• Borrelli , R.C. , Mennella , C. , Barba , F. , Russo , M. , Russo , G.L. , Krome , K. , Erbersdobler , H.F. , Faist , V. and Fogliano , V. 2003 . Characterization of coloured compounds obtained by enzymatic extraction of bakery products . Food and Chemical Toxicology , 41 : 1367 – 1374 .
   PubMed Web of Science ®Google Scholar
• Rizzi , G.P. 1997 . Chemical structure of coloured Maillard reactions products . Food Reviews International , 13 : 1 – 28 .
   Web of Science ®Google Scholar
• Ibarz , A. , Garvín , A. , Garza , S. and Pagán , J. 2009 . Toxic effect of melanoidins from glucose–asparagine on trypsin activity . Food and Chemical Toxicology , 47 : 2071 – 2075 .
   PubMed Web of Science ®Google Scholar
• Öste , R.E. , Dahlqvist , A. , Sjöström , H. , Norén , O. and Miller , R. 1986 . Effect of Maillard reaction products on protein digestion. In vitro studies . Journal of Agricultural and Food Chemistry , 34 : 355 – 358 .
   Web of Science ®Google Scholar
• Öste , R.E. and Sjödin , P. 1984 . Effect of Maillard reaction products on protein digestion. In vivo studies on rats . Journal of Nutrition , 144 : 2228 – 2234 .
   Google Scholar
• Rufián-Henares , J.A. and Morales , F.J. 2007 . Functional properties of melanoidins: In vitro antioxidant, antimicrobial and antihypertensive activities . Food research International , 40 : 995 – 1002 .
   Web of Science ®Google Scholar
• Rufian-Henares , J.A. and Morales , F.J. 2007 . Angiotensin-I converting enzyme inhibitory activity of coffee melanoidins . Journal of Agricultural and Food Chemistry , 55 : 1480 – 1485 .
   PubMed Web of Science ®Google Scholar
• Morales , F.J. , Fernandez-Fraguas , C. and Jimenez-Perez , S. 2005 . Iron-binding ability of melanoidins from food and model systems . Food Chemistry , 90 : 821 – 827 .
   Web of Science ®Google Scholar
• Lee , G.D. and Known , J.H. 1998 . The use of response surface methodology to optimize the Maillard reaction to produce melanoidins with high antioxidative and antimutagenenic activities . International Journal of Food Science and Technology , 33 : 375 – 383 .
   Web of Science ®Google Scholar
• Yen , G.C. , Tsai , L.C. and Lii , J.D. 1992 . Antimutagenic effect of Maillard browning products obtained from amino acids and sugars . Food and Chemical Toxicology , 30 : 127 – 132 .
   PubMed Web of Science ®Google Scholar
• Marko , D. , Habermeyer , M. , Kemény , M. , Weyand , U. , Niederberger , E. , Frank , O. and Hofmann , T. 2003 . Maillard reaction products modulating the growth of human tumor cells in vitro . Chemical Research in Toxicology , 16 : 48 – 55 .
   PubMed Web of Science ®Google Scholar
• Lobo , V. , Patil , A. , Phatak , A. and Chandra , N. 2010 . Free radicals, antioxidants and functional foods: Impact on human health . Pharmacological Review , 4 : 118 – 126 .
   PubMedGoogle Scholar
• Wagner , K.H. , Derkits , S. , Herr , M. , Schuh , S. and Elmadfa , I. 2002 . Antioxidative potential of melanoidins isolated from a roasted glucose-glycine model . Food Chemistry , 78 : 375 – 382 .
   Web of Science ®Google Scholar
• Valls-Bellés , V.; Torres, M.C.; Muñiz, P.; Boix, L.; González-Sanjose, M.L.; Codoñer-Franch, P. 2004 . The protective effects of melanoidins in adriamycin-induced oxidative stress in isolated rat hepatocytes . Journal of the Science and Food Agriculture , 84 : 1701 – 1707 .
   Web of Science ®Google Scholar
• Morales , F.J. and Babbel , M.B. 2002 . Melanoidins exert a weak antiradical activity in watery fluids . Journal of Agricultural and Food Chemistry , 50 : 4657 – 4661 .
   PubMed Web of Science ®Google Scholar
• Yoshimura , Y. , Iijima , T. , Watanabe , T. and Nakazawa , H. 1997 . Antioxidative effect of Maillard reaction products Rusing glucose-glycine model system . Journal of Agricultural and Food Chemistry , 45 : 4106 – 4109 .
   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 . Journal of Cereal Science , 45 : 327 – 334 .
   Web of Science ®Google Scholar
• Delgado-Andrade , C. , Rufián-Henares , J.A. and Morales , F.J. 2005 . Assessing the antioxidant activity of melanoidins from coffee brews by different antioxidant methods . Journal of Agricultural and Food Chemistry , 53 : 7832 – 7836 .
   PubMed Web of Science ®Google Scholar
• Martin , M.A. , Ramos , S. , Mateos , R. , Rufián-Henares , J.A. , Morales , F.J. , Bravo , L. and Goya , L. 2009 . Biscuit melanoidins of different molecular masses protect human HepG2 cells against oxidative stress . Journal of Agricultural and Food Chemistry , 57 : 7250 – 7258 .
   PubMed Web of Science ®Google Scholar
• Goya , L. , Delgado-Adnrade , C. , Rufián-Henares , J.A. , Bravo , L. and Morales , F.J. 2007 . Effect of coffee melanoidin on human hepatoma HepG2 cells. Protection against oxidative stress induced by tert-butylhydroperoxide . Molecular Nutrition and Food Research , 51 : 536 – 545 .
   PubMed Web of Science ®Google Scholar
• Borrelli , R.C. , Visconti , A. , Mennella , C. , Anese , M. and Fogliano , V. 2002 . Chemical characterization and antioxidant properties of coffee melanoidins . Journal of Agricultural and Food Chemistry , 50 : 6527 – 6533 .
   PubMed Web of Science ®Google Scholar
• Daglia , M. , Papetti , A. , Aceti , C. , Sordelli , B. , Gregotti , C. and Gazzani , G. 2008 . Isolation of high molecular weight components and contribution to the protective activity of coffee against lipid peroxidation in a rat liver microsome system . Journal of Agricultural and Food Chemistry , 56 : 11653 – 11660 .
   PubMed Web of Science ®Google Scholar
• Lerici , C.R. and Nicoli , M.C. 1996 . Chemical and physico-chemical properties affecting the quality and stability of bakery products . Advances in Food Science , 18 : 229 – 233 .
   Google Scholar
• Hansen , A.P. and Hemphill , P.L. 1984 . Utilization of heat to increase shelf life of blended acid whey and buttermilk powder for frozen desserts . Journal of Dairy Science , 67 : 54 – 56 .
   Google Scholar
• Bedinghaus , A.J. and Ockerman , H.W. 1995 . Antioxidative Maillard reaction products from reducing sugars and free amino acids in cooked ground pork patties . Journal of Food Science , 60 : 992 – 995 .
   Web of Science ®Google Scholar
• Rufián-Henares , J.A. and Morales , F.J. 2006 . A new application of a commercial microtiter plate-based assay for assessing the antimicrobial activity of Maillard reaction products . Food Research International , 39 : 33 – 39 .
   Web of Science ®Google Scholar
• Rufián-Henares , J.A. and Morales , F.J. 2008 . Microtiter plate-based assay for screening the specific antimicrobial activity of melanoidins . Food Chemistry , 111 : 1069 – 1074 .
   Web of Science ®Google Scholar
• Hiramoto , S. , Itoh , K. , Shizuuchi , S. , Kawachi , Y. , Morishita , Y. and Nagase , M. 2004 . Melanoidin, a food protein-derived advanced Maillard reaction product, suppresses Helicobacter pylori in vitro and in vivo . Helicobacter , 9 : 429 – 435 . Suzuki, Y.; Nobuta, Y.; Sudou, Y.; Nakamura, O.; Kagaya, I.; Goshima, H.; Kodama, Y.; Icatro, F.C.; Koizumi, W.; Saigenji, K.; Miura, S.; Sugiyama, T.; Kimura, N.
   PubMed Web of Science ®Google Scholar
• Trang , V.T. , Takeuchi , H. , Kudo , H. , Aoki , A. , Katsuno , S. and Shimamura , T. 2009 . Antimicrobial activity of aminoreductone against Helicobacter pylori . Journal of Agricultural and Food Chemistry , 57 : 11343 – 11348 . T.; Sugiura, T.; Ukeda, H.
   PubMed Web of Science ®Google Scholar
• Ames , J.M. , Wynne , A. , Hofmann , A. , Plos , S. and Gibson , G.R. 1999 . The effect of a model melanoidin mixture on faecal bacterial populations in vitro . British Journal of Nutrition , 82 : 489 – 495 .
   PubMed Web of Science ®Google Scholar
• Marko , D. , Kemény , M. , Bernady , E. , Habermeyer , M. , Weyand , U. and Meiers , S. 2002 . Studies on the inhibition of tumor cell growth and microtubule assembly by 3-hydroxy-4-[(E)-(2-furyl)methylidene]methyl-3- cyclopentene-1, 2-dione, an intensively coloured Maillard reaction product . Food and Chemical Toxicology , 40 : 9 – 18 . Frank, O.; Hofmann, T.
   PubMed Web of Science ®Google Scholar
• Kamei , H. , Koide , T. , Hashimoto , Y. , Kojima , T. , Umeda , T. and Hasegawa , M. 1997 . Tumor cell growth inhibiting effect of melanoidins extracted from miso and soy sauce . Cancer Biotherapy and Radiopharmaceuticals , 12 : 405 – 409 .
   PubMed Web of Science ®Google Scholar
• Langner , E. , Rzeski , W. , Kaczor , J. , Kandefer-Szerszeń , M. and Pierzynowski , S.G. 2009 . Tumor cell growth-inhibiting properties of water extract isolated from heated potato fibre (Potex) . Journal of Pre-Clinical and Clinical Research , 3 : 36 – 41 .
   Google Scholar
• Langner , E. , Nunes , F.M. , Pożarowski , P. , Kandefer-Szerszeń , M. , Pierzynowski , S.G. and Rzeski , W. 2011 . Antiproliferative activity of melanoidins isolated from heated potato fiber (Potex) in glioma cell culture model . Journal of Agricultural and Food Chemistry , 59 : 2708 – 2716 .
   PubMed Web of Science ®Google Scholar
• Wenzel , E. , Tasto , S. , Erbersdobler , H.F. and Faist , V. 2002 . Effect of heat treated proteins on selected parameters of the biotransformationsystem in the rat . Annals of Nutrition and Metabolism , 46 : 9 – 16 .
   PubMed Web of Science ®Google Scholar
• Lindenmeier , M. , Faist , V. and Hofmann , T. 2002 . Structural and functional characterization of pronyl-lysine, a novel protein modification in bread crust melanoidins showing in vitro antioxidative and phase I/II enzyme modulating activity . Journal of Agricultural and Food Chemistry , 50 : 6997 – 7006 .
   PubMed Web of Science ®Google Scholar
• Somoza , V. , Lindenmeier , M. , Wenzel , E. , Frank , O. , Erbersdobler , H.F. and Hofmann , T. 2003 . Activity-guided identification of a chemopreventive compound in coffee beverage using in vitro and in vivo techniques . Journal of Agricultural and Food Chemistry , 51 : 6861 – 6869 .
   PubMed Web of Science ®Google Scholar
• Boettler , U. , Sommerfeld , K. , Volz , N. , Pahlke , G. , Teller , N. and Somoza , V. Coffee constituents as modulators of Nrf2 nuclear translocation and ARE (EpRE)-dependent gene expression. Journal of Nutritional Biochemistry 2011 , 22, 426–440 . Lang, R.; Hofmann, T.; Marko, D.
   Google Scholar
• Cavin , C. , Marin-Kuan , M. , Langouët , S. , Bezençon , C. , Guignard , G. and Verguet , C. 2008 . Induction of Nrf2-mediated cellular defenses and alteration of phase I activities as mechanisms of chemoprotective effects of coffee in the liver . Food and Chemical Toxicology , 46 : 1239 – 1248 . Piguet, D.; Holzhäuser, D.; Cornaz, R.; Schilter, B.
   PubMed Web of Science ®Google Scholar
• Hofmann , T. , Bors , W. and Stettmaier , K. 1999 . Radical-assisted melanoidin formation during thermal processing of foods as well as under physiological conditions . Journal of Agricultural and Food Chemistry , 47 : 391 – 396 .
   PubMed Web of Science ®Google Scholar
• Summa , C. , McCourt , J. , Cämmerer , B. , Fiala , A. , Probst , M. and Kun , S. 2008 . Radical scavenging activity, antibacterial and mutagenic effects of cocoa bean Maillard reaction products with degree of roasting . Molecular Nutrition and Food Research , 52 : 342 – 351 . Anklam, E.; Wagner, K.H.
   PubMed Web of Science ®Google Scholar
• Obretenov , T.D. , Ivanova , S.D. , Kuntcheva , M.J. and Somov , G.T. 1993 . Melanoidin formation in cooked meat products . Journal of Agricultural and Food Chemistry , 41 : 653 – 656 .
   Web of Science ®Google Scholar
• Obretenov , T.D. , Kuntcheva , M.J. , Mantchev , S.C. and Valkova , G.D. 1991 . Isolation and characterization of melanoidins from malt and malt roots . Journal of Food Biochemistry , 15 : 279 – 294 .
   Web of Science ®Google Scholar
• Brudzynski , K. and Miotto , D. 2011 . Honey melanoidins: Analysis of the compositions of the high molecular weight melanoidins exhibiting radical-scavenging activity . Food Chemistry , 127 : 1023 – 1030 .
   PubMed Web of Science ®Google Scholar
• Calligaris , S. , Manzocco , L. , Anese , M. and Nicoli , M.C. 2004 . Effect of heat treatment on the antioxidant and pro-oxidant activity of milk . International Dairy Journal , 14 : 421 – 427 .
   Web of Science ®Google Scholar
• Ortega-Heras , M. and Gonzalez-Sanjosé , M.L. 2009 . Binding capacity of brown pigments present in special Spanish sweet wines . Food Science and Technology , 42 : 1729 – 1737 .
   Web of Science ®Google Scholar
• Falcone , P.M. and Giudici , P. 2008 . Molecular size and molecular size distribution affecting traditional balsamic vinegar aging . Journal of Agricultural and Food Chemistry , 56 : 7057 – 7066 .
   PubMed Web of Science ®Google Scholar
• Verzelloni , E. , Tagliazucchi , D. and Conte , A. 2010 . From balsamic to healthy: Traditional balsamic vinegar melanoidins inhibit lipid peroxidation during simulated gastric digestion of meat . Food and Chemical Toxicology , 48 : 2097 – 2102 .
   PubMed Web of Science ®Google Scholar
• Adams , A. , Borrelli , R.C. , Fogliano , V. and De Kimpe , N. 2005 . Thermal degradation studies of food melanoidins . Journal of Agricultural and Food Chemistry , 53 : 4136 – 4142 .
   PubMed Web of Science ®Google Scholar
• Ponnampalam , R. and Mondy , N.I. 2006 . Effect of baking and frying on nutritive value of potatoes nitrogenous constituents . Journal of Food Science , 48 : 1613 – 1616 .
   Web of Science ®Google Scholar
• Sakurai , H. , Hashiba , H. and Okuhara , A. 1981 . High molecular nitrogen compounds in soy sauce . Journal of Agricultural Chemical Society of Japan , 55 : 7 – 14 .
   Web of Science ®Google Scholar
• Wang , H. , Jenner , A.M. , Lee , J.C.Y. , Shui , G. , Tang , S.Y. , Whiteman , M. and Wenk , M.R. 2007 . The identification of antioxidants in dark soy sauce . Free Radical Research , 41 : 479 – 488 . Halliwell, B.
   PubMed Web of Science ®Google Scholar