Maillard reaction: formation, advantage, disadvantage and control. A review Maillard reaction: formation, advantage, …
Article Sidebar
Main Article Content
Abstract
The Maillard reaction (MR) is often known as the amino-carbonyl reaction, nonenzymatic browning, or protein glycation reaction. The non-enzymatic browning reaction is influenced by several factors like period, quantity of H2O, temperature, involved reactants, pH, and metal ions in food. During the production, processing, and storage of food, the MR is a crucial chemical process. While Maillard reaction products (MRPs) can enhance food quality during processing, some unfavorable reactions can also result in undesirable food effects. There are two sides to MRPs. The positive side is that these products have several advantages such as improvement in color, odor, flavor, and antioxidant ability. On the other hand, the negative side represents decreasing food quality and the nutritional value of some foods, as well as some health-related problems. The review involves several strategies by which MR could be controlled or prevented. These strategies were divided into two parts, the first is non-enzymatic which is done by adding functional ingredients that work to modify reducing sugars and amino groups and/or trapping of α-dicarbonyl compounds. The second is enzymatic, by using enzymes for example, fructosamine kinase, fructosamine oxidase, and lactose oxidase.
Article Details
References
Abdoh A., Al-Omari M., Badwan A., Jaber A. Amlodipine besylate-excipients interaction in the solid dosage form. Pharmaceutical Development and Technology, 2004, 9(1): 15-24. https://doi.org/10.1081/PDT-120027414.
Ajandouz E., Tchiakpe L., Dalle F., Benajiba A., Puigserver A. Effects of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. Journal of Food Science, 2001, 66(7): 926-931. https://doi.org/10.1111/j.1365-621.2001.tb08213.x
Alabbas K., Salih O., Al-Abbasy O. Isolation, purification, and characterization of pecan nut lipase and studying its affinity towards pomegranate extracts and 1,4- diacetoxybenzene. Iraqi Journal of Science, 2022, 63(3): 908-922. https://doi.org/10.24996/ijs.2022.63.3.1
ALjahdali N., Carbonero F. Impact of Maillard reaction products on nutrition and health: current knowledge and need to understand their fate in the human digestive system. Critical Reviews in Food Science and Nutrition, 2019, 59(3): 474-487. https://doi.org/10.1080/10408398.2017.1378865
Al-Saadi J., Easa A., Deeth H. Effect of lactose on cross-linking of milk proteins during heat treatments. International Journal of Dairy Technology, 2013, 66(1): 1-6. https://doi.org/10.1111/j.1471-0307.2012.00878.x
Ames J. Control of the Maillard reactions in food systems. Trends in Food Science & Technology, 1990, 1(7): 150-154. https://doi.org/10.1016/0924-2244(90)90113-D
Bankar S., Bule M., Singhal R., Ananthanarayan L. Glucose oxidase − an overview. Biotechnology Advances, 2009, 27(4): 489-501. https://doi.org/10.1016/j.biotechadv.2009.04.003
Barrett N., Grandison A., Lewis M. Contribution of the lactoperoxidase system to the keeping quality of pasteurized milk. Journal of Dairy Research, 1999, 66(1): 73-80. https://doi.org/10.1017/s0022029998003252
Baynes J. Maillard hypothesis on aging: time to focus on DNA. Annals of the New York Academy of Sciences, 2002, 959(1): 360-367. https://doi.org/10.1111/j.1749-6632.2002.tb02107.x
Bertrand E., Machado-Maturana E., Chevarin C., Portanguen S., Mercier F., Tournayre P., Abouelkaram S., Guillard A., Kondjoyan A. Berdagué J. Heat-induced volatiles and odour-active compounds in a model cheese. International Dairy Journal, 2011, 21(10): 806-814. https://doi.org/10.1016/j.idairyj.2011.04.007
Bertrand E., Meyer X., Machado-Maturana E., Berdagué J., Kondjoyan A. Modelling the Maillard reaction during the cooking of a model cheese. Food Chemistry, 2015, 184(10): 229-237. https://doi.org/10.1016/j.foodchem.2015.03.097
Brown Jr.W., Brown W.H., Foote C. Aromatics II: Reactions of Benzene and its Derivatives. In: Organic Chemistry. 3rd Edition (W.H. Brown, C. Foote Eds.). Harcourt College Publishers. 2002, рр. 802-836, Print ISBN: 978-0-0303-3574-7, ISBN-10: 0030334977
Cadwallader K., Singh T. Flavours and Off-Flavors in Milk and Dairy Products. In: Advanced Dairy Chemistry (P. McSweeney, P. Fox Eds.). Advanced Dairy Chemistry. Springer. 2009, рр. 631-690, Print ISBN: 978-0-387-84864-8, Online ISBN: 978-0-387-84865-5 https://doi.org/10.1007/978-0-387-84865-5_14
Cao J., Yan H., Liu L. Optimized preparation and antioxidant activity of glucose-lysine Maillard reaction products. LWT, 2022, 161(5): 113343. https://doi.org/10.1016/j.lwt.2022.113343
Carvalho D., Goncalves L., Guido L.F. Overall Antioxidant Properties of Malt and How They Are Influenced by the Individual Constituents of Barley and the Malting Process. Comprehensive Reviews in Food Science and Food Safety, 2016, 15(5): 927-943. https://doi.org/10.1111/1541-4337.12218
Castro, Luis F., Abigail D. Affonso, and Renata M. Lehman. Impact of specialty malts on wort and beer characteristics. Fermentation, 2021, 7(3): 137. https://doi.org/10.3390/fermentation7030137
Cha J., Debnath T. Lee K. Analysis of α-dicarbonyl compounds and volatiles formed in Maillard reaction model systems. Scientific Reports, 2019, 9(2019): 5325. https://doi.org/10.1038/s41598-019-41824-8
Chen H., Cerami A. Mechanism of inhibition of advanced glycosylation by aminoguanidine in vitro. Journal of Carbohydrate Chemistry, 1993, 12(6): 731-742. https://doi.org/10.1080/07328309308019003
Chevalier F., Chobert J., Genot C., Haertlé T. Scavenging of free radicals, antimicrobial, and cytotoxic activities of the Maillard reaction products of α-lactoglobulin glycated with several sugars. Journal of Agricultural and Food Chemistry, 2001, 49(10): 5031-5038. https://doi.org/10.1021/jf010549x.
Chevalier F., Chobert J., Popineau Y., Nicolas M., Haertlé T. Improvement of functional properties of β-lactoglobulin glycated through the Maillard reaction is related to the nature of the sugar. International Dairy Journal, 2001, 11(3): 145-152. https://doi.org/10.1016/S0958-6946(01)00040-1
Choi R., O'Malley C., Fairbanks B. A proposed method for the determination of the color of dry products of milk. Journal Dairy Science, 1949, 32: 580-586. https://doi.org/10.3168/jds.S0022-0302(49)92084-6
Coghe S., D’Hollander H., Verachtert H., Delvaux F. Impact of dark specialty malts on extract composition and wort fermentation. Journal in Brewing Science, 2005, 11151-11160. https://doi.org/10.1002/j.2050-0416.2005.tb00648.x
Colahan-Sederstrom P., Peterson D., Inhibition of key aroma compounds generated during ultrahigh-temperature processing of bovine milk via epicatechin addition. Journal of Agricultural and Food Chemistry, 2005, 53(2): 398-402. https://doi.org/10.1021/jf0487248
Cui H., Yu J., Shuqin X., Emmanuel D., Qingrong H., Xiaoming Z. Improved controlled flavor formation during heat-treatment with a stable Maillard reaction intermediate derived from xylose-phenylalanine. Food Chemistry, 2019, 271(15): 47-53. https://doi.org/10.1016/j.foodchem.2018.07.161
De Oliveira F., Coimbra J., de Oliveira E., Zuñiga A. Rojas E. Food protein-polysaccharide conjugates obtained via the Maillard reaction: A review. Critical Reviews in Food Science and Nutrition, 2016, 56(7): 1108-1125. https://doi.org/10.1080/10408398.2012.755669
Delgado-Andrade C., Seiquer I., García M., Galdó G., Navarro M. Increased intake of Maillard reaction products reduces phosphorous digestibility in male adolescents. Nutrition, 2011, 27(1): 86-91. https://doi.org/10.1016/j.nut.2009.10.009
Delgado-Andrade C., Seiquer I., Navarro M. Effects of consumption of Maillard reaction products on magnesium digestibility and tissue distribution in rats. Food Science and Technology International, 2007, 13(2): 109-115. https://doi.org/10.1177/1082013207078524
Deppe V., Bongaerts J., O’Connell T., Maurer K., Meinhardt F. Enzymatic deglycation of Amadori products in bacteria: mechanisms, occurrence and physiological functions. Applied Microbiology and Biotechnology, 2011, 90(2): 399-406. https://doi.org/10.1007/s00253-010-3083-4
Edelman R., Assaraf Y., Levitzky I., Shahar T., Livney Y. Hyaluronic acid-serum albumin conjugate-based nanoparticles for targeted cancer therapy. Oncotarget, 2017, 8(15): 24337-24353. https://doi.org/10.18632/oncotarget.15363
Es-Safi N., Le Guerneve C., Cheynier V., Moutounet M. New phenolic compounds obtained by the evolution of (+)-catechin and glyoxylic acid in hydroalcoholic medium. Tetrahedron Lett, 2000, 41(12): 1917−1921.
https://doi.org/10.1016/S0040-4039(00)00043-5.
Ford J., Hurrell R., Finot P. Storage of milk powders under adverse conditions: 2. Influence on the content of water-soluble vitamins. British Journal of Nutrition, 1983, 49(3): 355-364. https://doi.org/10.1079/BJN19830044
Friedman M. Food browning and its prevention: an overview. Journal of Agricultural and Food Chemistry, 1996, 44(3): 631-653. https://doi.org/10.1021/jf950394r
Fu Y, Zhang Y, Soladoye OP, Aluko RE. Maillard reaction products derived from food protein-derived peptides: Insights into flavor and bioactivity. Critical Reviews in Food Science and Nutrition, 2020, 60(20): 3429-3442. https://doi.org/10.1080/10408398.2019.1691500
García M., Seiquer I., Delgado-Andrade C., Galdó G., Navarro M.P. Intake of Maillard reaction products reduce iron bioavailability in male adolescents. Molecular Nutrition & Food Research, 2009, 53 (12): 1551-1560. https://doi.org/10.1002/mnfr.200800330
Gijs L., Perpète P., Timmermans A., Guyot-Declerck C., Delincé P., Collin S. Assessment of added glutathione in yeast propagations, wort fermentations, and beer storage. Journal of the American Society of Brewing Chemists, 2004, 62(3): 97-102. https://doi.org/10.1094/ASBCJ-62-0097
Gilani G., Xiao C., Cockell K. Impact of antinutritional factors in food proteins on the digestibility of proteins and the bioavailability of amino acids and on protein quality. British Journal of Nutrition, 2012, 108(2): S315-S332. https://doi.org/10.1017/S0007114512002371
Goulding D., Fox P., O’Mahony J. Milk Proteins: An Overview. In: Milk Proteins. Third Edition (M. Boland, H. Singh Eds.). Academic Press, Elsevier Inc. 2020, рр. 21-98, ISBN: 978-0-12-815251-5 https://doi.org/10.1016/B978-0-12-815251-5.00002-5
Guerra P., Yaylayan V. Interaction of flavanols with amino acids: postoxidative reactivity of the B-ring of catechin with glycine. Journal of Agricultural and Food Chemistry, 2014, 62(17): 3831−3836. https://doi.org/10.1021/jf5005989
HabinshutiI., Chen X., Yu J., Mukeshimana O., Duhoranimana E., Karangwa E., Zhang X. Antimicrobial, antioxidant and sensory properties of Maillard reaction products (MRPS) derived from sunflower, soybean, and corn meal hydrolysates. LWT, 2019, 101(3): 694-702. https://doi.org/10.1016/j.lwt.2018.11.083
Hafsa J., Smach M., Mrid R., Sobeh M., Majdoub H., Yasri A. Functional properties of chitosan derivatives obtained through Maillard reaction: A novel promising food preservative. Food Chemistry, 2021, 349(1): 129072. https://doi.org/10.1016/j.foodchem.2021.129072
Halpin R., Duffy L., Cregenzán-Alberti O., Lyng J., Noci F. The effect of non-thermal processing technologies on microbial inactivation: An investigation into sub-lethal injury of Escherichia coli and Pseudomonas fluorescence. Food Control, 2014, 41(7): 106-115. https://doi.org/10.1016/j.foodcont.2014.01.011
Hartauer K., Guillory J. A comparison of diffuse reflectance FT-IR spectroscopy and DSC in the characterization of a drugexcipient interaction. Drug Development and Industrial Pharmacy, 1991, 17(4): 617-630. https://doi.org/10.3109/03639049109044268
Hartog J., Voors A., Schalkwijk C., Scheijen J., Smilde T., Damman K., Bakker S., Smit A., van Veldhuisen D. Clinical and prognostic value of advanced glycation end-products in chronic heart failure. European Heart Journal, 2007, 28(23): 2879-2885. https://doi.org/10.1093/eurheartj/ehm486
Hellwig M., Henle T. Baking, ageing, diabetes: a short history of the Maillard reaction. Angewandte Chemie International Edition, 2014, 53(39): 10316-10329. https://doi.org/10.1002/anie.201308808.
Henning C., Smuda M., Girndt M., Ulrich C., Glomb M. Molecular basis of maillard amide-advanced glycation end product (AGE) formation in vivo. Journal of Biological Chemistry, 2011, 286(52): 44350-44356. https://doi.org/10.1074/jbc.M111.282442
Hirsch J., Petrakova E., Feather M. The reaction of some dicarbonyl sugars with aminoguanidine. Carbohydrate Research, 1992, 232(1): 125-130. https://doi.org/10.1016/S0008-6215(00)90999-6
Hodge J. Chemistry of browning reactions in model systems. Journal of Agricultural and Food Chemistry, 1953, 1(15): 928-943. https://doi.org/10.1021/jf60015a004.
Ilchmann A., Burgdorf S., Scheurer S., Waibler Z., Nagai R., Wellner A., Yamamoto Y., Yamamoto H., Henle T., Kurts C., Kalinke U., Vieths S., Toda M. Glycation of a food allergen by the Maillard reaction enhances its T-cell immunogenicity: role of macrophage scavenger receptor class A type I and II. Journal of Allergy and Clinical Immunology, 2010, 125(1): 175-183. https://doi.org/10.1016/j.jaci.2009.08.013
Jansson T., Clausen M., Sundekilde. U., Eggers N., Nyegaard S., Larsen L., Ray C., Sundgren A., Andersen H. Bertram H. Lactose-hydrolyzed milk is more prone to chemical changes during storage than conventional ultra-high-temperature (UHT) milk Journal of Agricultural and Food Chemistry, 2014, 62(31): 7886-7896. https://doi.org/10.1021/jf501671z
Jansson T., Jensen H., Sundekilde U., Clausen M., Eggers N., Larsen L., Ray C., Andersen H. Bertram H. Chemical and proteolysis-derived changes during long-term storage of lactose-hydrolyzed ultrahigh-temperature (UHT) milk. Journal of Agricultural and Food Chemistry, 2014, 62(46): 11270-11278. https://doi.org/10.1021/jf504104q.
Jarunglumlert T., Nakagawa K., Adachi S. Influence of aggregate structure of casein on the encapsulation efficiency of β-carotene entrapped via hydrophobic interaction. Food Structure, 2015, 5(7): 42-50. https://doi.org/10.1016/j.foostr.2015.05.001
Jongberg S., Gislason N., Lund M., Skibsted L., Waterhouse A. Thiol-quinone adduct formation in myofibrillar proteins detected by LC-MS. Journal of Agricultural and Food Chemistry, 2011, 59(13): 6900-6905. https://doi.org/10.1021/jf200965s.
Joubran Y., Moscovici A., Lesmes U. Antioxidant activity of bovine alpha lactalbumin Maillard products and evaluation of their in vitro gastro-duodenal digestive proteolysis. Food & Function, 2015, 6(4): 1229-1240. https://doi.org/10.1039/C4FO01165A
Karagül-Yüceer Y., Drake M., Cadwallader K. Aroma-active components of nonfat dry milk. Journal of Agricultural and Food Chemistry, 2001, 49(60): 2948-2953. https://doi.org/10.1021/jf0009854
Kathuria D., Hamid A., Gautam S., Thakur A. Maillard reaction in different food products: Effect on product quality, human health and mitigation strategies. Food Control, 2023,153(11): 109911. https://doi.org/10.1016/j.foodcont.2023.109911
Khan M., Liu H., Wang J., Sun B. Inhibitory effect of phenolic compounds and plant extracts on the formation of advance glycation end products: a comprehensive review. Food Research International, 2020, 130(4): 108933. https://doi.org/10.1016/j.foodres.2019.108933
Kumar P., Banker G. Maillard Reaction and Drug Stability. In: Maillard Reactions in Chemistry, Food and Health (T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O'Brien, J.W. Baynes Eds.). Woodhead Publishing Limited. 1998, рр. 20-27, ISBN: 978-1-85573-792-1 https://doi.org/10.1533/9781845698393.1.20
Lakkis J., Villota R. Comparative performance of chemically and enzymatically modified whey proteins. Food Chemistry, 1992a, 43(2): 93-105. https://doi.org/10.1016/0308-8146(92)90221-M
Le T., Bhandari B., Holland J., Deeth H. Maillard reaction and protein cross-linking in relation to the solubility of milk powders. Journal of Agricultural and Food Chemistry, 2011, 59(23): 12473-12479. https://doi.org/10.1021/jf203460z
Ledesma-Osuna A., Amos-Clamont G., Vazquez-Moreno L. Characterisation of bovine serum albumin glycated with glucose, galactose and lactose. Acta Biochimica Polonica, 2008, 55(3): 491-497. https://doi.org/10.18388/abp.2008_3054
Lee Y., Tang T., Phuah E., Alitheen N., Tan C., Lai O. New functionalities of Maillard reaction products as emulsifiers and encapsulating agents, and the processing parameters: a brief review. Journal of the Science of Food and Agriculture, 2017, 97(5): 1379-1385. https://doi.org/10.1002/jsfa.8124
Li Y., Jongberg S. Andersen M., Davies M., Lund M. Quinone-induced protein modifications: kinetic preference for reaction of 1,2-benzoquinones with thiol groups in proteins. Free Radical Biology and Medicine, 2016, 97(8): 148-157. https://doi.org/10.1016/j.freeradbiomed.2016.05.019
Lin Z., Zheng J. Occurrence, characteristics, and applications of fructosyl amine oxidases (amadoriases). Applied Microbiology and Biotechnology, 2010, 86(6): 1613-1619. https://doi.org/10.1007/s00253-010-2523-5
Liscomb C., Bies D., Hansen R. Specialty malt contributions to wort and beer. Master Brewers Association of the Americas. Technical Quarterly, 2015, 52(4): 181-190. http://dx.doi.org/10.1094/TQ-52-4-1115-01
Liu L., Li X., Zhu Y., Bora A., ZhaoY., Du L., Li D., Bi W. Effect of microencapsulation with Maillard reaction products of whey proteins and isomaltoligosaccharide on the survival of Lactobacillus rhamnosus. LWT, 2016, 73(11): 37-43. https://doi.org/10.1016/j.lwt.2016.05.030
Liu S., Sun H., Ma G., Zhang T., Wang L., Pei H., Li X. Gao L. Insights into flavor and key influencing factors of Maillard reaction products: a recent update. Frontiers in Nutrition, 2022b, 9(9): 973677. https://doi.org/10.3389/fnut.2022.973677
Liu X., Xia B., Hu L., Ni Z., Thakur K., Wei Z. Maillard conjugates and their potential in food and nutritional industries: A review. Food Frontiers, 2020, 1(4): 382-397. https://doi.org/10.1002/fft2.43
Lovdahl M., Hurley T., Tobias B., Priebe S. Synthesis and characterization of pregabalin lactose conjugate degradation products. Journal of Pharmaceutical and Biomedical Analysis, 2002, 28(5): 917-924. https://doi.org/10.1016/S0731-7085(01)00710-5
Manch G., Shepherd C., Mccann H. Intraneuronal advanced glycation endproducts in presenilin-1 Alzheimer disease. NeuroReport, 2002, 13(5): 601-604. https://doi.org/10.1097/00001756-200204160-00013
Marko D., Habermeyer M., Kemény M., Weyand U., Niederberger E., Frank O., Hofmann T. Maillard reaction products modulating the growth of human tumor cells in vitro. Chemical Research in Toxicology, 2003, 16(1): 48-55. https://doi.org/10.1021/tx025531a
Meydani B., Vahedifar A., Askari G., Madadlou A. Influence of the Maillard reaction on the properties of cold-set whey protein and maltodextrin binary gels. International Dairy Journal, 2019, 90(3): 79-87. https://doi.org/10.1016/j.idairyj.2018.11.009
Mittelmaier S., Pischetsrieder M. Multistep ultrahigh performance liquid chromatography/tandem mass spectrometry analysis for untargeted quantification of glycating activity and identification of most relevant glycation products. Analytical Chemistry, 2011, 83(24): 9660-9668. https://doi.org/10.1021/ac2025706
Moreno F., Molina E., Olano A., López-Fandiño R. High- pressure effects on Maillard reaction between glucose and lysine. Journal of Agricultural and Food Chemistry, 2003, 51(2): 394-400. https://doi.org/10.1021/jf025731s
Muhoza B., Xia S., Cai J., Zhang X., Su J., Li L. Time effect on coenzyme Q10 loading and stability of micelles based on glycosylated casein via Maillard reaction. Food Hydrocolloids, 2017, 72(11): 271-280. https://doi.org/10.1016/j.foodhyd.2017.05.046
Mukherjee K., Hutkins R. Isolation of galactosefermenting thermophilic cultures and their use in the manufacture of low browning mozarella cheese. Journal of Dairy Science, 1994, 77(10): 2839-2849. https://doi.org/10.3168/jds.S0022-0302(94)77223-4
Murata M. Browning and pigmentation in food through the Maillard reaction. Glycoconjugate Journal, 2021, 38(3): 283-292. https://doi.org/10.1007/s10719-020-09943-x
Naranjo G., Malec L., Vigo M. Reducing sugars effect on available lysine loss of casein by moderate heat treatment. Food Chemistry, 1998, 62(3): 309-313. https://doi.org/10.1016/S0308-8146(97)00176-3
Newton A., Fairbanks A., Golding M., Andrewes P., Gerrard J. The role of the Maillard reaction in the formation of flavour compounds in dairy products–not only a deleterious reaction but also a rich source of flavour compounds. Food & Function, 2012, 3(12): 1231-1241. https://doi.org/10.1039/C2FO30089C
Nooshkam M., Varidi M. and Verma D. Functional and biological properties of maillard conjugates and their potential application in medical and food: a review. Food Research International, 2020, 131(5): 109003. https://doi.org/10.1016/j.foodres.2020.109003
Nooshkam M., Varidi M. Bashash M. The Maillard reaction products as food-born antioxidant and antibrowning agents in model and real food systems. Food Chemistry, 2019, 275(1): 644-660. https://doi.org/10.1016/j.foodchem.2018.09.083
Oliver C., Melton L., Stanley R. Creating proteins with novel functionality via the Maillard reaction: A review. Crit. Rev. Food Sci. Nutr, 2006, 46(4): 337-350. https://doi.org/10.1080/10408690590957250
Patil D., Patil C. Modification of pharmacological activity of nebivolol due to Maillard reaction. Pharm. Dev. Technol, 2013, 18(4): 844–851. https://doi.org/10.3109/10837450.2011.591802
Peng P., Song H., Zhang T., Addy M., Zhang Y., Cheng Y., Hatzenbeller R., Zhu X., Liu S., Liu Y. Concentrated high intensity electric field (chief) system for non-thermal pasteurization of liquid foods: Modeling and simulation of fluid mechanics, electric analysis, and heat transfer. Computers & Chemical Engineering, 2017, 97(2): 183-193. https://doi.org/10.1016/j.compchemeng.2016.11.044
Perez-Locas C., Yaylayan V. The Maillard reaction and food quality deterioration in book: Chemical Deterioration and Physical Instability of Food and Beverages. 2010, pp. 70-94 https://doi.org/10.1533/9781845699260.1.70.
Pierpoint W. o-Quinones formed in plant extracts. Their reactions with amino acids and peptides. Biochemical Journal, 1969, 112(5): 609-616. https://doi.org/10.1042/bj1120609.
Purlis E. Browning development in bakery products – A review. Journal of Food Engineering, 2010, 99(3): 239-249. https://doi.org/10.1016/j.jfoodeng.2010.03.008
Qin X., Yuan D., Wang Q., Hu Z., Wu Y., Cai J., Huang Q., Li S., Liu G. Maillard-reacted whey protein isolates enhance thermal stability of anthocyanins over a wide pH range. J Journal of Agricultural and Food Chemistry, 2018, 66(36): 9556-9564. https://doi.org/10.1021/acs.jafc.8b03125
Rada-Mendoza M., Villamiel M., Ramírez A., Usuriaga Y., Montilla A. Quality indicators in lactose hydrolyzed milks and soy beverages from Colombia. Journal of Food Science and Technology, 2022, 59(2): 646-654. https://doi.org/10.1007/s13197-021-05055-y
Rifai L., Saleh F. A review on acrylamide in food: Occurrence, toxicity, and mitigation strategies. International Journal of Toxicology, 2020, 39(2): 93-102. https://doi.org/10.1177/1091581820902405
Schmutzler S., Knappe D., Marx A., Hoffmann R. Solid-phase synthesis of D-fructose-derived Heyns peptides utilizing Nα-Fmoc-Lysin[Nε-(2-deoxy-D-glucos-2-yl),Nε-Boc]-OH as building block. Amino Acids, 2021, 53(6): 881-891. https://doi.org/10.1007/s00726-021-02989-7
Seiquer I., Diaz-Alguacil J., Delgado-Andrade C., Lopez-Frias M., Hoyos A., Galdo G., Navarro M. Diets rich in Maillard reaction products affect protein digestibility in adolescent males aged 11-14 y. The American Journal of Clinical Nutrition, 2006, 83(5): 1082-1088. https://doi.org/10.1093/ajcn/83.5.1082
Shahidi F. Antioxidants in food and food antioxidants. Molecular Nutrition & Food Research (Food/ Nahrung), 2000, 44(3): 158-163. https://doi.org/10.1002/1521-3803(20000501)44:3<158::AID-FOOD158>3.0.CO;2-L
Shao X., Chen H., Zhu Y., Sedighi R., Ho C., Sang S. Essential structural requirements and additive effects for flavonoids to scavenge methylglyoxal. Journal of Agricultural and Food Chemistry, 2014, 62 (14): 3202-3210. https://doi.org/10.1021/jf500204s
Singleton V., Salgues M., Zaya J., Trousdale E. Caftaric acid dissapearance and conversion to products of enzymic oxidation in grape must and wine. American Journal of Enology and Viticulture, 1985, 36(1): 50-56. https://doi.org/10.5344/ajev.1985.36.1.50
Stitt A. Advanced glycation: an important pathological event in diabetic and age related ocular disease. British Journal of Ophthalmology, 2001, 85(6): 746-753. http://doi.org/10.1136/bjo.85.6.746
Sun W., Zhao M., Cui C., Zhao Q., Yang B. Effect of Maillard reaction products derived from the hydrolysate of mechanically deboned chicken residue on the antioxidant, textural and sensory properties of Cantonese sausages. Meat Science, 2010, 86(2): 276-282. https://doi.org/10.1016/j.meatsci.2010.04.014
Tagliamonte S., Dario Troise A., Ferracane R., Vitaglione P. The Maillard reaction end product Nε-carboxymethyllysine is metabolized in humans and the urinary levels of the microbial etabolites are associated with individual diet. Food & Function, 2023, 14(4): 2074-2081. https://doi.org/10.1039/D2FO03480H
Taherzadeh M., Gustafsson L., Niklasson C., Liden G. Conversion of furfural in aerobic and anaerobic batch fermentation of glucose by Saccharomyces cerevisiae. Journal of Bioscience and Bioengineering, 1999, 87(2): 169-174. https://doi.org/10.1016/S1389-1723(99)89007-0
Tanaka M., Kimiagar M., Lee T., Chichester C. Effect of Maillard Browning Reaction on Nutritional Quality of Protein. In: Protein Crosslinking. Advances in Experimental Medicine and Biology, Volume 86 (Friedman, M. Ed.). Springer. 1977, pp. 321-341. Print ISBN: 978-1-4757-9115-0, Online ISBN: 978-1-4757-9113-6 https://doi.org/10.1007/978-1-4757-9113-6_22
Törős G., Peles F., Elramady H., Prokisch J. To What Extent Can Maillard Reaction Products Influence the Probiotic and Harmful Bacteria? Egyptian Journal of Soil Science, 2023, 63(2): 177-185. https://doi.org/10.21608/EJSS.2023.189687.1569
Troise A., Dathan N., Fiore A., Roviello D., Di Fiore A., Caira S., Cuollo M., De Simone G., Fogliano V., Monti S. Faox enzymes inhibited Maillard reaction development during storage both in protein glucose model system and low lactose UHT milk. Amino Acids, 2014, 46(2): 279-288. https://doi.org/10.1007/s00726-013-1497-x
Troise A. Fiore A., Colantuono A., Kokkinidou S., Peterson D., Fogliano V. Effect of olive mill wastewater phenolcompounds on reactive carbonyl species and Maillard reaction endproducts in ultrahigh-temperature-treated milk. Journal of Agricultural and Food Chemistry, 2014, 62(41): 10092-10100. https://doi.org/10.1021/jf503329d
Uribarri J., Woodruff S., Goodman S., Cai W., Chen X., Pyzik R., Yong A., Striker G., Vlassara H. Advanced glycation end products in foods and a practical guide to their reduction in the diet Journal of the Academy of Nutrition and Dietetics, 2010, 110(6): 911-916. https://doi.org/10.1016/j.jada.2010.03.018
Viegas O., Novo P., Pinto E., Pinho O., Ferreira O. Effect of charcoal types and grilling conditions on formation of heterocyclic aromatic amines (HAs) and polycyclic aromatic hydrocarbons (PAHs) in grilled muscle foods. Food and Chemical Toxicology, 2012, 50(6):2128-34. https://doi.org/10.1016/j.fct.2012.03.051
Wang H., Qian H., YaoW. Melanoidins produced by the Maillard reaction: structure and biological activity. Food Chemistry, 2011, 128 (3): 573-584. https://doi.org/10.1016/j.foodchem.2011.03.075
Wang T., Xue J., Hu Q., Zhou M., Chang C., Luo Y. Synthetic surfactant- and cross-linker-free preparation of highly stable lipid-polymer hybrid nanoparticles as potential oral delivery vehicles. Scientific Reports, 2017, 7(1): 2750. https://doi.org/10.1038/s41598-017-02867-x.
Wang Z., Jiang Y., Liu N., Ren L., Zhu Y., An Y., Chen D. Advanced glycation end-product N-carboxymethyl-Lysine accelerates progression of atherosclerotic calcification in diabetes. Atherosclerosis, 2012, 221(2): 387-396. https://doi.org/10.1016/j.atherosclerosis.2012.01.019
Wu C., Huang S., Lin J., Yen G. Inhibition of advanced glycation end product formation by foodstuffs. Food & Function, 2011, 2(5): 224-234. https://doi.org/10.1039/C1FO10026B.
Wu Q., Yang Ch., Zhang R. Editorial: Inhibition strategies on the formation of Maillard reaction products in food. Frontiers in Nutrition, 2023, 10:1162097. https://doi.org/10.3389/fnut.2023.1162097.
Wu Y., Wang X. Binding, stability, and antioxidant activity of curcumin with self-assembled casein–dextran conjugate micelles. International Journal of Food Properties, 2017, 20(12): 3295-3307. https://doi.org/10.1080/10942912.2017.1286505.
Xiang J., Liu F., Wang B., Chen L., Liu W. Tan S. A literature review on Maillard reaction based on milk proteins and carbohydrates in food and pharmaceutical products: advantages, disadvantages, and avoidance strategies. Foods, 2021, 10(9), 1998. https://doi.org/10.3390/foods10091998.
Xu Y., Li H., Liang J., Ma J., Yang J., Zhao X. High-throughput quantification of eighteen heterocyclic aromatic amines in roasted and pan-fried meat on the basis of high-performance liquid chromatography-quadrupole-orbitrap high resolution mass spectrometry. Food Chemistry 2021, 361:11. https://doi.org/10.1016/j.foodchem.2021.130147.
Yeboah F., Alli I., Yaylayan V. Reactivities of D-glucose and D-fructose during glycation of bovine serum albumin. Journal of Agricultural and Food Chemistry, 1999, 47(8): 3164-3172. https://doi.org/10.1021/jf981289v.
Yoshimura Y., Iijima T., Watanabe T., Nakazawa H. Antioxidative effect of Maillard reaction products using glucose-glycine model system. Journal of Agricultural and Food Chemistry, 1997, 45(10): 4106-4109. https://doi.org/10.1021/jf9609845.
Yu M., He S., Tang M., Zhang Z., Zhu Y., Sun H. Antioxidant activity and sensory characteristics of Maillard reaction products derived from different peptide fractions of soybean meal hydrolysate. Food Chemistry, 2018, 243 (15): 249-257. https://doi.org/10.1016/j.foodchem.2017.09.139
Zeng J., Davies M. Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. Chemical Research in Toxicology, 2006, 19(12): 1668-1676. https://doi.org/10.1021/tx0602158.
Zhang D., Ji W., Peng Y., Ji H., Gao J. Evaluation of flavor improvement in antarctic krill defluoridated hydrolysate by maillard reaction using sensory analysis, E-nose, and GC-MS. Journal of Aquatic Food Product Technology, 2020, 29(3): 279-292. https://doi.org/10.1080/10498850.2020.1723764.
Zhang J., Mei. Z., Huang X., Ding Y., Liang Y., Mei Y. Inhibition of Maillard reaction in production of low-molecular- weight chitosan by enzymatic hydrolysis. Carbohydrate Polymers, 2020, 236(15): 116059-116066. https://doi.org/10.1016/j.carbpol.2020.116059.
Zhong C., Tan S., Langrish T. Redness generation via Maillard reactions of whey protein isolate (WPI) and ascorbic acid (vitamin C) in spray-dried powders. Journal of Food Engineering, 2019, 244(3): 11-20. https://doi.org/10.1016/j.jfoodeng.2018.09.020.
Ajandouz E., Tchiakpe L., Dalle F., Benajiba A., Puigserver A. Effects of pH on caramelization and Maillard reaction kinetics in fructose-lysine model systems. Journal of Food Science, 2001, 66(7): 926-931. https://doi.org/10.1111/j.1365-621.2001.tb08213.x
Alabbas K., Salih O., Al-Abbasy O. Isolation, purification, and characterization of pecan nut lipase and studying its affinity towards pomegranate extracts and 1,4- diacetoxybenzene. Iraqi Journal of Science, 2022, 63(3): 908-922. https://doi.org/10.24996/ijs.2022.63.3.1
ALjahdali N., Carbonero F. Impact of Maillard reaction products on nutrition and health: current knowledge and need to understand their fate in the human digestive system. Critical Reviews in Food Science and Nutrition, 2019, 59(3): 474-487. https://doi.org/10.1080/10408398.2017.1378865
Al-Saadi J., Easa A., Deeth H. Effect of lactose on cross-linking of milk proteins during heat treatments. International Journal of Dairy Technology, 2013, 66(1): 1-6. https://doi.org/10.1111/j.1471-0307.2012.00878.x
Ames J. Control of the Maillard reactions in food systems. Trends in Food Science & Technology, 1990, 1(7): 150-154. https://doi.org/10.1016/0924-2244(90)90113-D
Bankar S., Bule M., Singhal R., Ananthanarayan L. Glucose oxidase − an overview. Biotechnology Advances, 2009, 27(4): 489-501. https://doi.org/10.1016/j.biotechadv.2009.04.003
Barrett N., Grandison A., Lewis M. Contribution of the lactoperoxidase system to the keeping quality of pasteurized milk. Journal of Dairy Research, 1999, 66(1): 73-80. https://doi.org/10.1017/s0022029998003252
Baynes J. Maillard hypothesis on aging: time to focus on DNA. Annals of the New York Academy of Sciences, 2002, 959(1): 360-367. https://doi.org/10.1111/j.1749-6632.2002.tb02107.x
Bertrand E., Machado-Maturana E., Chevarin C., Portanguen S., Mercier F., Tournayre P., Abouelkaram S., Guillard A., Kondjoyan A. Berdagué J. Heat-induced volatiles and odour-active compounds in a model cheese. International Dairy Journal, 2011, 21(10): 806-814. https://doi.org/10.1016/j.idairyj.2011.04.007
Bertrand E., Meyer X., Machado-Maturana E., Berdagué J., Kondjoyan A. Modelling the Maillard reaction during the cooking of a model cheese. Food Chemistry, 2015, 184(10): 229-237. https://doi.org/10.1016/j.foodchem.2015.03.097
Brown Jr.W., Brown W.H., Foote C. Aromatics II: Reactions of Benzene and its Derivatives. In: Organic Chemistry. 3rd Edition (W.H. Brown, C. Foote Eds.). Harcourt College Publishers. 2002, рр. 802-836, Print ISBN: 978-0-0303-3574-7, ISBN-10: 0030334977
Cadwallader K., Singh T. Flavours and Off-Flavors in Milk and Dairy Products. In: Advanced Dairy Chemistry (P. McSweeney, P. Fox Eds.). Advanced Dairy Chemistry. Springer. 2009, рр. 631-690, Print ISBN: 978-0-387-84864-8, Online ISBN: 978-0-387-84865-5 https://doi.org/10.1007/978-0-387-84865-5_14
Cao J., Yan H., Liu L. Optimized preparation and antioxidant activity of glucose-lysine Maillard reaction products. LWT, 2022, 161(5): 113343. https://doi.org/10.1016/j.lwt.2022.113343
Carvalho D., Goncalves L., Guido L.F. Overall Antioxidant Properties of Malt and How They Are Influenced by the Individual Constituents of Barley and the Malting Process. Comprehensive Reviews in Food Science and Food Safety, 2016, 15(5): 927-943. https://doi.org/10.1111/1541-4337.12218
Castro, Luis F., Abigail D. Affonso, and Renata M. Lehman. Impact of specialty malts on wort and beer characteristics. Fermentation, 2021, 7(3): 137. https://doi.org/10.3390/fermentation7030137
Cha J., Debnath T. Lee K. Analysis of α-dicarbonyl compounds and volatiles formed in Maillard reaction model systems. Scientific Reports, 2019, 9(2019): 5325. https://doi.org/10.1038/s41598-019-41824-8
Chen H., Cerami A. Mechanism of inhibition of advanced glycosylation by aminoguanidine in vitro. Journal of Carbohydrate Chemistry, 1993, 12(6): 731-742. https://doi.org/10.1080/07328309308019003
Chevalier F., Chobert J., Genot C., Haertlé T. Scavenging of free radicals, antimicrobial, and cytotoxic activities of the Maillard reaction products of α-lactoglobulin glycated with several sugars. Journal of Agricultural and Food Chemistry, 2001, 49(10): 5031-5038. https://doi.org/10.1021/jf010549x.
Chevalier F., Chobert J., Popineau Y., Nicolas M., Haertlé T. Improvement of functional properties of β-lactoglobulin glycated through the Maillard reaction is related to the nature of the sugar. International Dairy Journal, 2001, 11(3): 145-152. https://doi.org/10.1016/S0958-6946(01)00040-1
Choi R., O'Malley C., Fairbanks B. A proposed method for the determination of the color of dry products of milk. Journal Dairy Science, 1949, 32: 580-586. https://doi.org/10.3168/jds.S0022-0302(49)92084-6
Coghe S., D’Hollander H., Verachtert H., Delvaux F. Impact of dark specialty malts on extract composition and wort fermentation. Journal in Brewing Science, 2005, 11151-11160. https://doi.org/10.1002/j.2050-0416.2005.tb00648.x
Colahan-Sederstrom P., Peterson D., Inhibition of key aroma compounds generated during ultrahigh-temperature processing of bovine milk via epicatechin addition. Journal of Agricultural and Food Chemistry, 2005, 53(2): 398-402. https://doi.org/10.1021/jf0487248
Cui H., Yu J., Shuqin X., Emmanuel D., Qingrong H., Xiaoming Z. Improved controlled flavor formation during heat-treatment with a stable Maillard reaction intermediate derived from xylose-phenylalanine. Food Chemistry, 2019, 271(15): 47-53. https://doi.org/10.1016/j.foodchem.2018.07.161
De Oliveira F., Coimbra J., de Oliveira E., Zuñiga A. Rojas E. Food protein-polysaccharide conjugates obtained via the Maillard reaction: A review. Critical Reviews in Food Science and Nutrition, 2016, 56(7): 1108-1125. https://doi.org/10.1080/10408398.2012.755669
Delgado-Andrade C., Seiquer I., García M., Galdó G., Navarro M. Increased intake of Maillard reaction products reduces phosphorous digestibility in male adolescents. Nutrition, 2011, 27(1): 86-91. https://doi.org/10.1016/j.nut.2009.10.009
Delgado-Andrade C., Seiquer I., Navarro M. Effects of consumption of Maillard reaction products on magnesium digestibility and tissue distribution in rats. Food Science and Technology International, 2007, 13(2): 109-115. https://doi.org/10.1177/1082013207078524
Deppe V., Bongaerts J., O’Connell T., Maurer K., Meinhardt F. Enzymatic deglycation of Amadori products in bacteria: mechanisms, occurrence and physiological functions. Applied Microbiology and Biotechnology, 2011, 90(2): 399-406. https://doi.org/10.1007/s00253-010-3083-4
Edelman R., Assaraf Y., Levitzky I., Shahar T., Livney Y. Hyaluronic acid-serum albumin conjugate-based nanoparticles for targeted cancer therapy. Oncotarget, 2017, 8(15): 24337-24353. https://doi.org/10.18632/oncotarget.15363
Es-Safi N., Le Guerneve C., Cheynier V., Moutounet M. New phenolic compounds obtained by the evolution of (+)-catechin and glyoxylic acid in hydroalcoholic medium. Tetrahedron Lett, 2000, 41(12): 1917−1921.
https://doi.org/10.1016/S0040-4039(00)00043-5.
Ford J., Hurrell R., Finot P. Storage of milk powders under adverse conditions: 2. Influence on the content of water-soluble vitamins. British Journal of Nutrition, 1983, 49(3): 355-364. https://doi.org/10.1079/BJN19830044
Friedman M. Food browning and its prevention: an overview. Journal of Agricultural and Food Chemistry, 1996, 44(3): 631-653. https://doi.org/10.1021/jf950394r
Fu Y, Zhang Y, Soladoye OP, Aluko RE. Maillard reaction products derived from food protein-derived peptides: Insights into flavor and bioactivity. Critical Reviews in Food Science and Nutrition, 2020, 60(20): 3429-3442. https://doi.org/10.1080/10408398.2019.1691500
García M., Seiquer I., Delgado-Andrade C., Galdó G., Navarro M.P. Intake of Maillard reaction products reduce iron bioavailability in male adolescents. Molecular Nutrition & Food Research, 2009, 53 (12): 1551-1560. https://doi.org/10.1002/mnfr.200800330
Gijs L., Perpète P., Timmermans A., Guyot-Declerck C., Delincé P., Collin S. Assessment of added glutathione in yeast propagations, wort fermentations, and beer storage. Journal of the American Society of Brewing Chemists, 2004, 62(3): 97-102. https://doi.org/10.1094/ASBCJ-62-0097
Gilani G., Xiao C., Cockell K. Impact of antinutritional factors in food proteins on the digestibility of proteins and the bioavailability of amino acids and on protein quality. British Journal of Nutrition, 2012, 108(2): S315-S332. https://doi.org/10.1017/S0007114512002371
Goulding D., Fox P., O’Mahony J. Milk Proteins: An Overview. In: Milk Proteins. Third Edition (M. Boland, H. Singh Eds.). Academic Press, Elsevier Inc. 2020, рр. 21-98, ISBN: 978-0-12-815251-5 https://doi.org/10.1016/B978-0-12-815251-5.00002-5
Guerra P., Yaylayan V. Interaction of flavanols with amino acids: postoxidative reactivity of the B-ring of catechin with glycine. Journal of Agricultural and Food Chemistry, 2014, 62(17): 3831−3836. https://doi.org/10.1021/jf5005989
HabinshutiI., Chen X., Yu J., Mukeshimana O., Duhoranimana E., Karangwa E., Zhang X. Antimicrobial, antioxidant and sensory properties of Maillard reaction products (MRPS) derived from sunflower, soybean, and corn meal hydrolysates. LWT, 2019, 101(3): 694-702. https://doi.org/10.1016/j.lwt.2018.11.083
Hafsa J., Smach M., Mrid R., Sobeh M., Majdoub H., Yasri A. Functional properties of chitosan derivatives obtained through Maillard reaction: A novel promising food preservative. Food Chemistry, 2021, 349(1): 129072. https://doi.org/10.1016/j.foodchem.2021.129072
Halpin R., Duffy L., Cregenzán-Alberti O., Lyng J., Noci F. The effect of non-thermal processing technologies on microbial inactivation: An investigation into sub-lethal injury of Escherichia coli and Pseudomonas fluorescence. Food Control, 2014, 41(7): 106-115. https://doi.org/10.1016/j.foodcont.2014.01.011
Hartauer K., Guillory J. A comparison of diffuse reflectance FT-IR spectroscopy and DSC in the characterization of a drugexcipient interaction. Drug Development and Industrial Pharmacy, 1991, 17(4): 617-630. https://doi.org/10.3109/03639049109044268
Hartog J., Voors A., Schalkwijk C., Scheijen J., Smilde T., Damman K., Bakker S., Smit A., van Veldhuisen D. Clinical and prognostic value of advanced glycation end-products in chronic heart failure. European Heart Journal, 2007, 28(23): 2879-2885. https://doi.org/10.1093/eurheartj/ehm486
Hellwig M., Henle T. Baking, ageing, diabetes: a short history of the Maillard reaction. Angewandte Chemie International Edition, 2014, 53(39): 10316-10329. https://doi.org/10.1002/anie.201308808.
Henning C., Smuda M., Girndt M., Ulrich C., Glomb M. Molecular basis of maillard amide-advanced glycation end product (AGE) formation in vivo. Journal of Biological Chemistry, 2011, 286(52): 44350-44356. https://doi.org/10.1074/jbc.M111.282442
Hirsch J., Petrakova E., Feather M. The reaction of some dicarbonyl sugars with aminoguanidine. Carbohydrate Research, 1992, 232(1): 125-130. https://doi.org/10.1016/S0008-6215(00)90999-6
Hodge J. Chemistry of browning reactions in model systems. Journal of Agricultural and Food Chemistry, 1953, 1(15): 928-943. https://doi.org/10.1021/jf60015a004.
Ilchmann A., Burgdorf S., Scheurer S., Waibler Z., Nagai R., Wellner A., Yamamoto Y., Yamamoto H., Henle T., Kurts C., Kalinke U., Vieths S., Toda M. Glycation of a food allergen by the Maillard reaction enhances its T-cell immunogenicity: role of macrophage scavenger receptor class A type I and II. Journal of Allergy and Clinical Immunology, 2010, 125(1): 175-183. https://doi.org/10.1016/j.jaci.2009.08.013
Jansson T., Clausen M., Sundekilde. U., Eggers N., Nyegaard S., Larsen L., Ray C., Sundgren A., Andersen H. Bertram H. Lactose-hydrolyzed milk is more prone to chemical changes during storage than conventional ultra-high-temperature (UHT) milk Journal of Agricultural and Food Chemistry, 2014, 62(31): 7886-7896. https://doi.org/10.1021/jf501671z
Jansson T., Jensen H., Sundekilde U., Clausen M., Eggers N., Larsen L., Ray C., Andersen H. Bertram H. Chemical and proteolysis-derived changes during long-term storage of lactose-hydrolyzed ultrahigh-temperature (UHT) milk. Journal of Agricultural and Food Chemistry, 2014, 62(46): 11270-11278. https://doi.org/10.1021/jf504104q.
Jarunglumlert T., Nakagawa K., Adachi S. Influence of aggregate structure of casein on the encapsulation efficiency of β-carotene entrapped via hydrophobic interaction. Food Structure, 2015, 5(7): 42-50. https://doi.org/10.1016/j.foostr.2015.05.001
Jongberg S., Gislason N., Lund M., Skibsted L., Waterhouse A. Thiol-quinone adduct formation in myofibrillar proteins detected by LC-MS. Journal of Agricultural and Food Chemistry, 2011, 59(13): 6900-6905. https://doi.org/10.1021/jf200965s.
Joubran Y., Moscovici A., Lesmes U. Antioxidant activity of bovine alpha lactalbumin Maillard products and evaluation of their in vitro gastro-duodenal digestive proteolysis. Food & Function, 2015, 6(4): 1229-1240. https://doi.org/10.1039/C4FO01165A
Karagül-Yüceer Y., Drake M., Cadwallader K. Aroma-active components of nonfat dry milk. Journal of Agricultural and Food Chemistry, 2001, 49(60): 2948-2953. https://doi.org/10.1021/jf0009854
Kathuria D., Hamid A., Gautam S., Thakur A. Maillard reaction in different food products: Effect on product quality, human health and mitigation strategies. Food Control, 2023,153(11): 109911. https://doi.org/10.1016/j.foodcont.2023.109911
Khan M., Liu H., Wang J., Sun B. Inhibitory effect of phenolic compounds and plant extracts on the formation of advance glycation end products: a comprehensive review. Food Research International, 2020, 130(4): 108933. https://doi.org/10.1016/j.foodres.2019.108933
Kumar P., Banker G. Maillard Reaction and Drug Stability. In: Maillard Reactions in Chemistry, Food and Health (T.P. Labuza, G.A. Reineccius, V.M. Monnier, J. O'Brien, J.W. Baynes Eds.). Woodhead Publishing Limited. 1998, рр. 20-27, ISBN: 978-1-85573-792-1 https://doi.org/10.1533/9781845698393.1.20
Lakkis J., Villota R. Comparative performance of chemically and enzymatically modified whey proteins. Food Chemistry, 1992a, 43(2): 93-105. https://doi.org/10.1016/0308-8146(92)90221-M
Le T., Bhandari B., Holland J., Deeth H. Maillard reaction and protein cross-linking in relation to the solubility of milk powders. Journal of Agricultural and Food Chemistry, 2011, 59(23): 12473-12479. https://doi.org/10.1021/jf203460z
Ledesma-Osuna A., Amos-Clamont G., Vazquez-Moreno L. Characterisation of bovine serum albumin glycated with glucose, galactose and lactose. Acta Biochimica Polonica, 2008, 55(3): 491-497. https://doi.org/10.18388/abp.2008_3054
Lee Y., Tang T., Phuah E., Alitheen N., Tan C., Lai O. New functionalities of Maillard reaction products as emulsifiers and encapsulating agents, and the processing parameters: a brief review. Journal of the Science of Food and Agriculture, 2017, 97(5): 1379-1385. https://doi.org/10.1002/jsfa.8124
Li Y., Jongberg S. Andersen M., Davies M., Lund M. Quinone-induced protein modifications: kinetic preference for reaction of 1,2-benzoquinones with thiol groups in proteins. Free Radical Biology and Medicine, 2016, 97(8): 148-157. https://doi.org/10.1016/j.freeradbiomed.2016.05.019
Lin Z., Zheng J. Occurrence, characteristics, and applications of fructosyl amine oxidases (amadoriases). Applied Microbiology and Biotechnology, 2010, 86(6): 1613-1619. https://doi.org/10.1007/s00253-010-2523-5
Liscomb C., Bies D., Hansen R. Specialty malt contributions to wort and beer. Master Brewers Association of the Americas. Technical Quarterly, 2015, 52(4): 181-190. http://dx.doi.org/10.1094/TQ-52-4-1115-01
Liu L., Li X., Zhu Y., Bora A., ZhaoY., Du L., Li D., Bi W. Effect of microencapsulation with Maillard reaction products of whey proteins and isomaltoligosaccharide on the survival of Lactobacillus rhamnosus. LWT, 2016, 73(11): 37-43. https://doi.org/10.1016/j.lwt.2016.05.030
Liu S., Sun H., Ma G., Zhang T., Wang L., Pei H., Li X. Gao L. Insights into flavor and key influencing factors of Maillard reaction products: a recent update. Frontiers in Nutrition, 2022b, 9(9): 973677. https://doi.org/10.3389/fnut.2022.973677
Liu X., Xia B., Hu L., Ni Z., Thakur K., Wei Z. Maillard conjugates and their potential in food and nutritional industries: A review. Food Frontiers, 2020, 1(4): 382-397. https://doi.org/10.1002/fft2.43
Lovdahl M., Hurley T., Tobias B., Priebe S. Synthesis and characterization of pregabalin lactose conjugate degradation products. Journal of Pharmaceutical and Biomedical Analysis, 2002, 28(5): 917-924. https://doi.org/10.1016/S0731-7085(01)00710-5
Manch G., Shepherd C., Mccann H. Intraneuronal advanced glycation endproducts in presenilin-1 Alzheimer disease. NeuroReport, 2002, 13(5): 601-604. https://doi.org/10.1097/00001756-200204160-00013
Marko D., Habermeyer M., Kemény M., Weyand U., Niederberger E., Frank O., Hofmann T. Maillard reaction products modulating the growth of human tumor cells in vitro. Chemical Research in Toxicology, 2003, 16(1): 48-55. https://doi.org/10.1021/tx025531a
Meydani B., Vahedifar A., Askari G., Madadlou A. Influence of the Maillard reaction on the properties of cold-set whey protein and maltodextrin binary gels. International Dairy Journal, 2019, 90(3): 79-87. https://doi.org/10.1016/j.idairyj.2018.11.009
Mittelmaier S., Pischetsrieder M. Multistep ultrahigh performance liquid chromatography/tandem mass spectrometry analysis for untargeted quantification of glycating activity and identification of most relevant glycation products. Analytical Chemistry, 2011, 83(24): 9660-9668. https://doi.org/10.1021/ac2025706
Moreno F., Molina E., Olano A., López-Fandiño R. High- pressure effects on Maillard reaction between glucose and lysine. Journal of Agricultural and Food Chemistry, 2003, 51(2): 394-400. https://doi.org/10.1021/jf025731s
Muhoza B., Xia S., Cai J., Zhang X., Su J., Li L. Time effect on coenzyme Q10 loading and stability of micelles based on glycosylated casein via Maillard reaction. Food Hydrocolloids, 2017, 72(11): 271-280. https://doi.org/10.1016/j.foodhyd.2017.05.046
Mukherjee K., Hutkins R. Isolation of galactosefermenting thermophilic cultures and their use in the manufacture of low browning mozarella cheese. Journal of Dairy Science, 1994, 77(10): 2839-2849. https://doi.org/10.3168/jds.S0022-0302(94)77223-4
Murata M. Browning and pigmentation in food through the Maillard reaction. Glycoconjugate Journal, 2021, 38(3): 283-292. https://doi.org/10.1007/s10719-020-09943-x
Naranjo G., Malec L., Vigo M. Reducing sugars effect on available lysine loss of casein by moderate heat treatment. Food Chemistry, 1998, 62(3): 309-313. https://doi.org/10.1016/S0308-8146(97)00176-3
Newton A., Fairbanks A., Golding M., Andrewes P., Gerrard J. The role of the Maillard reaction in the formation of flavour compounds in dairy products–not only a deleterious reaction but also a rich source of flavour compounds. Food & Function, 2012, 3(12): 1231-1241. https://doi.org/10.1039/C2FO30089C
Nooshkam M., Varidi M. and Verma D. Functional and biological properties of maillard conjugates and their potential application in medical and food: a review. Food Research International, 2020, 131(5): 109003. https://doi.org/10.1016/j.foodres.2020.109003
Nooshkam M., Varidi M. Bashash M. The Maillard reaction products as food-born antioxidant and antibrowning agents in model and real food systems. Food Chemistry, 2019, 275(1): 644-660. https://doi.org/10.1016/j.foodchem.2018.09.083
Oliver C., Melton L., Stanley R. Creating proteins with novel functionality via the Maillard reaction: A review. Crit. Rev. Food Sci. Nutr, 2006, 46(4): 337-350. https://doi.org/10.1080/10408690590957250
Patil D., Patil C. Modification of pharmacological activity of nebivolol due to Maillard reaction. Pharm. Dev. Technol, 2013, 18(4): 844–851. https://doi.org/10.3109/10837450.2011.591802
Peng P., Song H., Zhang T., Addy M., Zhang Y., Cheng Y., Hatzenbeller R., Zhu X., Liu S., Liu Y. Concentrated high intensity electric field (chief) system for non-thermal pasteurization of liquid foods: Modeling and simulation of fluid mechanics, electric analysis, and heat transfer. Computers & Chemical Engineering, 2017, 97(2): 183-193. https://doi.org/10.1016/j.compchemeng.2016.11.044
Perez-Locas C., Yaylayan V. The Maillard reaction and food quality deterioration in book: Chemical Deterioration and Physical Instability of Food and Beverages. 2010, pp. 70-94 https://doi.org/10.1533/9781845699260.1.70.
Pierpoint W. o-Quinones formed in plant extracts. Their reactions with amino acids and peptides. Biochemical Journal, 1969, 112(5): 609-616. https://doi.org/10.1042/bj1120609.
Purlis E. Browning development in bakery products – A review. Journal of Food Engineering, 2010, 99(3): 239-249. https://doi.org/10.1016/j.jfoodeng.2010.03.008
Qin X., Yuan D., Wang Q., Hu Z., Wu Y., Cai J., Huang Q., Li S., Liu G. Maillard-reacted whey protein isolates enhance thermal stability of anthocyanins over a wide pH range. J Journal of Agricultural and Food Chemistry, 2018, 66(36): 9556-9564. https://doi.org/10.1021/acs.jafc.8b03125
Rada-Mendoza M., Villamiel M., Ramírez A., Usuriaga Y., Montilla A. Quality indicators in lactose hydrolyzed milks and soy beverages from Colombia. Journal of Food Science and Technology, 2022, 59(2): 646-654. https://doi.org/10.1007/s13197-021-05055-y
Rifai L., Saleh F. A review on acrylamide in food: Occurrence, toxicity, and mitigation strategies. International Journal of Toxicology, 2020, 39(2): 93-102. https://doi.org/10.1177/1091581820902405
Schmutzler S., Knappe D., Marx A., Hoffmann R. Solid-phase synthesis of D-fructose-derived Heyns peptides utilizing Nα-Fmoc-Lysin[Nε-(2-deoxy-D-glucos-2-yl),Nε-Boc]-OH as building block. Amino Acids, 2021, 53(6): 881-891. https://doi.org/10.1007/s00726-021-02989-7
Seiquer I., Diaz-Alguacil J., Delgado-Andrade C., Lopez-Frias M., Hoyos A., Galdo G., Navarro M. Diets rich in Maillard reaction products affect protein digestibility in adolescent males aged 11-14 y. The American Journal of Clinical Nutrition, 2006, 83(5): 1082-1088. https://doi.org/10.1093/ajcn/83.5.1082
Shahidi F. Antioxidants in food and food antioxidants. Molecular Nutrition & Food Research (Food/ Nahrung), 2000, 44(3): 158-163. https://doi.org/10.1002/1521-3803(20000501)44:3<158::AID-FOOD158>3.0.CO;2-L
Shao X., Chen H., Zhu Y., Sedighi R., Ho C., Sang S. Essential structural requirements and additive effects for flavonoids to scavenge methylglyoxal. Journal of Agricultural and Food Chemistry, 2014, 62 (14): 3202-3210. https://doi.org/10.1021/jf500204s
Singleton V., Salgues M., Zaya J., Trousdale E. Caftaric acid dissapearance and conversion to products of enzymic oxidation in grape must and wine. American Journal of Enology and Viticulture, 1985, 36(1): 50-56. https://doi.org/10.5344/ajev.1985.36.1.50
Stitt A. Advanced glycation: an important pathological event in diabetic and age related ocular disease. British Journal of Ophthalmology, 2001, 85(6): 746-753. http://doi.org/10.1136/bjo.85.6.746
Sun W., Zhao M., Cui C., Zhao Q., Yang B. Effect of Maillard reaction products derived from the hydrolysate of mechanically deboned chicken residue on the antioxidant, textural and sensory properties of Cantonese sausages. Meat Science, 2010, 86(2): 276-282. https://doi.org/10.1016/j.meatsci.2010.04.014
Tagliamonte S., Dario Troise A., Ferracane R., Vitaglione P. The Maillard reaction end product Nε-carboxymethyllysine is metabolized in humans and the urinary levels of the microbial etabolites are associated with individual diet. Food & Function, 2023, 14(4): 2074-2081. https://doi.org/10.1039/D2FO03480H
Taherzadeh M., Gustafsson L., Niklasson C., Liden G. Conversion of furfural in aerobic and anaerobic batch fermentation of glucose by Saccharomyces cerevisiae. Journal of Bioscience and Bioengineering, 1999, 87(2): 169-174. https://doi.org/10.1016/S1389-1723(99)89007-0
Tanaka M., Kimiagar M., Lee T., Chichester C. Effect of Maillard Browning Reaction on Nutritional Quality of Protein. In: Protein Crosslinking. Advances in Experimental Medicine and Biology, Volume 86 (Friedman, M. Ed.). Springer. 1977, pp. 321-341. Print ISBN: 978-1-4757-9115-0, Online ISBN: 978-1-4757-9113-6 https://doi.org/10.1007/978-1-4757-9113-6_22
Törős G., Peles F., Elramady H., Prokisch J. To What Extent Can Maillard Reaction Products Influence the Probiotic and Harmful Bacteria? Egyptian Journal of Soil Science, 2023, 63(2): 177-185. https://doi.org/10.21608/EJSS.2023.189687.1569
Troise A., Dathan N., Fiore A., Roviello D., Di Fiore A., Caira S., Cuollo M., De Simone G., Fogliano V., Monti S. Faox enzymes inhibited Maillard reaction development during storage both in protein glucose model system and low lactose UHT milk. Amino Acids, 2014, 46(2): 279-288. https://doi.org/10.1007/s00726-013-1497-x
Troise A. Fiore A., Colantuono A., Kokkinidou S., Peterson D., Fogliano V. Effect of olive mill wastewater phenolcompounds on reactive carbonyl species and Maillard reaction endproducts in ultrahigh-temperature-treated milk. Journal of Agricultural and Food Chemistry, 2014, 62(41): 10092-10100. https://doi.org/10.1021/jf503329d
Uribarri J., Woodruff S., Goodman S., Cai W., Chen X., Pyzik R., Yong A., Striker G., Vlassara H. Advanced glycation end products in foods and a practical guide to their reduction in the diet Journal of the Academy of Nutrition and Dietetics, 2010, 110(6): 911-916. https://doi.org/10.1016/j.jada.2010.03.018
Viegas O., Novo P., Pinto E., Pinho O., Ferreira O. Effect of charcoal types and grilling conditions on formation of heterocyclic aromatic amines (HAs) and polycyclic aromatic hydrocarbons (PAHs) in grilled muscle foods. Food and Chemical Toxicology, 2012, 50(6):2128-34. https://doi.org/10.1016/j.fct.2012.03.051
Wang H., Qian H., YaoW. Melanoidins produced by the Maillard reaction: structure and biological activity. Food Chemistry, 2011, 128 (3): 573-584. https://doi.org/10.1016/j.foodchem.2011.03.075
Wang T., Xue J., Hu Q., Zhou M., Chang C., Luo Y. Synthetic surfactant- and cross-linker-free preparation of highly stable lipid-polymer hybrid nanoparticles as potential oral delivery vehicles. Scientific Reports, 2017, 7(1): 2750. https://doi.org/10.1038/s41598-017-02867-x.
Wang Z., Jiang Y., Liu N., Ren L., Zhu Y., An Y., Chen D. Advanced glycation end-product N-carboxymethyl-Lysine accelerates progression of atherosclerotic calcification in diabetes. Atherosclerosis, 2012, 221(2): 387-396. https://doi.org/10.1016/j.atherosclerosis.2012.01.019
Wu C., Huang S., Lin J., Yen G. Inhibition of advanced glycation end product formation by foodstuffs. Food & Function, 2011, 2(5): 224-234. https://doi.org/10.1039/C1FO10026B.
Wu Q., Yang Ch., Zhang R. Editorial: Inhibition strategies on the formation of Maillard reaction products in food. Frontiers in Nutrition, 2023, 10:1162097. https://doi.org/10.3389/fnut.2023.1162097.
Wu Y., Wang X. Binding, stability, and antioxidant activity of curcumin with self-assembled casein–dextran conjugate micelles. International Journal of Food Properties, 2017, 20(12): 3295-3307. https://doi.org/10.1080/10942912.2017.1286505.
Xiang J., Liu F., Wang B., Chen L., Liu W. Tan S. A literature review on Maillard reaction based on milk proteins and carbohydrates in food and pharmaceutical products: advantages, disadvantages, and avoidance strategies. Foods, 2021, 10(9), 1998. https://doi.org/10.3390/foods10091998.
Xu Y., Li H., Liang J., Ma J., Yang J., Zhao X. High-throughput quantification of eighteen heterocyclic aromatic amines in roasted and pan-fried meat on the basis of high-performance liquid chromatography-quadrupole-orbitrap high resolution mass spectrometry. Food Chemistry 2021, 361:11. https://doi.org/10.1016/j.foodchem.2021.130147.
Yeboah F., Alli I., Yaylayan V. Reactivities of D-glucose and D-fructose during glycation of bovine serum albumin. Journal of Agricultural and Food Chemistry, 1999, 47(8): 3164-3172. https://doi.org/10.1021/jf981289v.
Yoshimura Y., Iijima T., Watanabe T., Nakazawa H. Antioxidative effect of Maillard reaction products using glucose-glycine model system. Journal of Agricultural and Food Chemistry, 1997, 45(10): 4106-4109. https://doi.org/10.1021/jf9609845.
Yu M., He S., Tang M., Zhang Z., Zhu Y., Sun H. Antioxidant activity and sensory characteristics of Maillard reaction products derived from different peptide fractions of soybean meal hydrolysate. Food Chemistry, 2018, 243 (15): 249-257. https://doi.org/10.1016/j.foodchem.2017.09.139
Zeng J., Davies M. Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. Chemical Research in Toxicology, 2006, 19(12): 1668-1676. https://doi.org/10.1021/tx0602158.
Zhang D., Ji W., Peng Y., Ji H., Gao J. Evaluation of flavor improvement in antarctic krill defluoridated hydrolysate by maillard reaction using sensory analysis, E-nose, and GC-MS. Journal of Aquatic Food Product Technology, 2020, 29(3): 279-292. https://doi.org/10.1080/10498850.2020.1723764.
Zhang J., Mei. Z., Huang X., Ding Y., Liang Y., Mei Y. Inhibition of Maillard reaction in production of low-molecular- weight chitosan by enzymatic hydrolysis. Carbohydrate Polymers, 2020, 236(15): 116059-116066. https://doi.org/10.1016/j.carbpol.2020.116059.
Zhong C., Tan S., Langrish T. Redness generation via Maillard reactions of whey protein isolate (WPI) and ascorbic acid (vitamin C) in spray-dried powders. Journal of Food Engineering, 2019, 244(3): 11-20. https://doi.org/10.1016/j.jfoodeng.2018.09.020.
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
Open access articles are distributed under the terms and conditions of the Creative Commons Attribution-Share Alike 4.0 International License (CC BY-SA 4.0) license:
https://creativecommons.org/licenses/by-sa/4.0
If you have any questions about the permitted uses of a specific article, please contact us.
Permissions Department of the Academic Publishing House of the UFT Plovdiv
Plovdiv 4002, 26 Maritsa Blvd., Bulgaria
E-mail: editor.in.chief@ijfsab.com
Tel.: +359 (32) 603-802
Fax: +359 32/ 644 102
How to Cite
AL-ABBASY, Omar Y. et al.
Maillard reaction: formation, advantage, disadvantage and control. A review.
Food Science and Applied Biotechnology, [S.l.], v. 7, n. 1, p. 145-161, mar. 2024.
ISSN 2603-3380.
Available at: <https://www.ijfsab.com/index.php/fsab/article/view/333>. Date accessed: 14 oct. 2024.
doi: https://doi.org/10.30721/fsab2024.v7.i1.333.