Abstract
The importance of Maillard reaction products is correlated with two main problems concerning the production and the commercialisation of foods and beverages: the loss of nutritional properties caused by Maillard reaction under drastic conditions and/or the possible risk caused by the presence of one or more Maillard reaction products in foods. The ‘Maillard reaction’ is a complex group of cascade reactions; parallel reaction chains may also cross themselves with interesting and perhaps unpredictable results. The final products are brownish polymers named melanoidins with notable molecular weights and variegated composition and structures. These polymers could not be obtained without the active role of several intermediates including 5-hydroxymethylfurfural, diacetyl, pyruvaldehyde, furosine. In particular, furosine has been studied thoroughly in the last 40 years because of its correlation with heat treatments and thermal effects on proteins. This chapter is dedicated to furosine and related analytical methods concerning food matrices.
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Abbreviations
- CZE:
-
Capillary zone electrophoresis
- HMF:
-
5-Hydroxymethylfurfural
- MRP:
-
Maillard reaction product
- RP-HPLC:
-
Reverse-phase high-performance liquid chromatography
- SPE:
-
Solid phase extraction
References
Arena S, Renzone G, D’Ambrosio C, Salzano AM, Scaloni A (2017) Dairy products and the Maillard reaction: a promising future for extensive food characterization by integrated proteomics studies. Food Chem 219:477–489. https://doi.org/10.1016/j.foodchem.2016.09.165
Belitz HD, Grosch W, Schieberle P (2009) Food chemistry, 4th edn. Springer, Berlin
Boitz LI, Mayer HK (2015) Evaluation of furosine, lactulose and acid-soluble β-lactoglobulin as time temperature integrators for whipping cream samples at retail in Austria. Int Dairy J 50:24–31. https://doi.org/10.1016/j.idairyj.2015.06.002
Bogdanov S, Martin P (2002) Honey authenticity. Mitt Lebensm Hyg 93(3):232–254
Bogdanov S, Martin P, Lüllmann C, Borneck R, Flamini C, Morlot M, Heretier J, Vorwohl G, Russmann H, Persano-Oddo L, Saba-tini AG, Marcazzan GL, Marioleas P, Tsigouri K, Kerkvliet J, Ortiz A, Ivanov T (1997) Harmonised methods of the European Honey Commission, Apidologie (extra issue), 1–59
Bornhorst ER, Tang J, Sablani SS, Barbosa-Cánovas GV (2017) Development of model food systems for thermal pasteurization applications based on Maillard reaction products. LWT-Food Sci Technol 75:417–424. https://doi.org/10.1016/j.lwt.2016.09.020
Cappelli P, Vannucchi V (1990) Chimica degli alimenti. Conservazione e trasformazione. Zanichelli, Bologna
Castro-Puyana M, Crego AL, Marina ML, García-Ruiz C (2007) CE methods for the determination of non-protein amino acids in foods. Electrophoresis 28(22):4031–4045. https://doi.org/10.1002/elps.200700169
Chhabra GS, Liu C, Su M, Venkatachalam M, Roux KH, Sathe SK (2017) Effects of the Maillard reaction on the immunoreactivity of amandin in food matrices. J Food Sci 82(10):2495–2503. https://doi.org/10.1111/1750-3841.13839
Coles R, Kirwan MJ (2011) Food and beverage packaging technology, 2nd edn. John Wiley & Sons, Chichester
Corradini D, Cannarsa G, Corradini C, Nicoletti I, Pizzoferrato L, Vivanti V (1996) Analysis of ε-N-2-furoylmethyl-L-lysine (furosine) in dried milk by capillary electrophoresis with controlled electroosmotic flow using N, N, N′, N′-tetramethyl-1, 3-butanediamine in the running electrolyte solution. Electrophoresis 17(1):120–124. https://doi.org/10.1002/elps.1150170120
Corzo-Martínez M, Corzo N, Villamiel M, del Castillo MD (2012) Browning reactions. In: Simpson BK (ed) Food biochemistry and food processing, 2nd edn, pp 56–83. https://doi.org/10.1002/9781118308035.ch4
da Silva PM, Gauche C, Gonzaga LV, Costa ACO, Fett R (2016) Honey: chemical composition, stability and authenticity. Food Chem 196:309–323. https://doi.org/10.1016/j.foodchem.2015.09.051
Delgado-Andrade C, Rufiàn-Henares J, Morales F (2005) Fast method to determine furosine in breakfast cereals by capillary zone electrophoresis. Eur Food Res Technol 221(5):707–711. https://doi.org/10.1007/s00217-005-0030-1
Delgado-Andrade C, Rufiàn-Henares J, Morales FJ (2009) Colour and fluorescence measurement as unspecific markers for the Maillard reaction. In: Proceedings of the COST-927 Action Training School “Assessing the generation and bioactivity of neo-formed compounds in thermally treated foods”, Granada, Spain, 9–13 March 2009. Available http://www.if.csic.es/proyectos/cost927/TS-COST927-GRANADA-Tuesday.pdf. Accessed 08 Nov 2017
Dills WL (1993) Protein fructosylation: fructose and the Maillard reaction. Am J Clin Nutr 58(5):779S–787S
Erbersdobler HF, Hupe A (1991) Determination of the lysine damage and calculation of lysine bio-availability in several processed foods. Z Ernährungswissenschaft 30(1):46–49
Erbersdobler HF, Dehn-Müller B, Nangpal A, Reuter H (1987) Determination of furosine in heated milk as a measure of heated intensity during processing. Dairy Res 54(1):147–151. https://doi.org/10.1017/S0022029900025255
Feather MS, Mossine V, Hirsch J (1995) The use of aminoguanidine to trap and measure decarbonyl intermediates produced during the Maillard reaction. In: Lee TC, Kim HJ (eds) Chemical Markers for Processed and Stored Foods, ACS Symposium Series 631, Chicago, pp. 24–31. https://doi.org/10.1021/bk-1996-0631.ch003
Finot PA, Deutsch R, Bujard E (1981) The extent of the Maillard reaction during the processing of milk. Progr Food Nutr Sci 5:345–355
Fiorino M, Parisi S (2016) Undesired chemical alterations and process-related causes. The role of thermal control and the management of thermal machines. In: Micali M, Fiorino M, Parisi S (eds) The chemistry of thermal food processing procedures, pp 41–54. Springer International Publishing, Cham
Friedman M (1996) Food Browning and Its Prevention:Â An Overview. Journal of Agricultural and Food Chemistry 44(3):631–653
Fu MX, Wells-Knecht KJ, Blackledge JA, Lyons TJ, Thorpe SR, Baynes JW (1994) Glycation, glycoxidation, and cross-linking of collagen by glucose: kinetics, mechanisms, and inhibition of late stages of the Maillard reaction. Diabetes 43(5):676–683. https://doi.org/10.2337/diab.43.5.676
Gartaula G, Adhikari BM (2014) Challenges and prospects of food science and technology education: Nepal’s perspective. Food Sci Nutr 2(6):623–627. https://doi.org/10.1002/fsn3.173
Ghiron AF, Quack B, Mahinney TP, Feather MS (1988) Studies on the role of 3-deoxy-d-erythro-glucosulose (3-glucosone)in nonenzymatic browning. Evidence for involvement in a Strecker degradation. J Agric Food Chem 36(4):677–680. https://doi.org/10.1021/jf00082a002
Giannetti V (2013) Furosine as a pasta quality marker. Tecnica Molitoria 12:1076–1088
Giannetti V, Mariani MB, Mannino P (2013) Furosine as a pasta quality marker: evaluation by an innovative and fast chromatographic approach. J Food Science 78(7):C994–C999. https://doi.org/10.1111/1750-3841.12163
Guerra-Hernández E, Corzo N, Garcia-Villanova B (1999) Maillard reaction evaluation by furosine determination during infant cereal processing. J Cereal Sci 29(2):171–176. https://doi.org/10.1006/jcrs.1998.0226
Henle T, Schwarzenbolz U, Walter AW, Klosterrneyer H (1998) Protein-bound Maillard compounds in foods: analytical and technological aspects. In: O’ Brien J, Nursten HE, Crabbe MJC, Ames JM (eds) The Maillard reaction in foods and medicine, Special Publication No 223. The Royas Society of Chemistry, London
Hodge JE (1953) Chemistry of browning reactions in model systems. J Agric Food Chem 1(15):928–943. https://doi.org/10.1021/jf60015a004
Huber B, Ledl F (1990) Formation of 1-amino-1,4- dideoxy-2,3-hexodiulose and 2-aminoacetylfurans in the Maillard reaction. Carbohydr Res 204:215–220. https://doi.org/10.1016/0008-6215(90)84037-u
Huyghues-Despointes A, Yaylayan VA (1996) Retroaldol and redox reactions of Amadori compounds: mechanistic studies with various labeled D-[13C] glucose. J Agric Food Chem 44(3):672–681. https://doi.org/10.1021/jf9502921
Kearney J (2010) Food consumption trends and drivers. Philos Trans R Soc Lond B Biol Sci 365(1554):2793–2807. https://doi.org/10.1098/rstb.2010.0149
Maillard LC (1912) Action des acidesamines sur les sucres: formation des melanoidines par voie methodique. Compt Rend Acad Sci (Paris) 154:66–68
Mania I, Barone C, Pellerito A, Laganà P, Parisi S (2017) Trasparenza e Valorizzazione delle Produzioni Alimentari. ’etichettatura e la Tracciabilità di Filiera come Strumenti di Tutela delle Produzioni Alimentari. Ind Aliment 56(581):18–22
Marcus N (2016) The Maillard Reaction: Radicals and Flavor. Group presentation (date: 22th march 2016), Department of Chemistry, University of Illinois. http://www.scs.illinois.edu/denmark/wp-content/uploads/2016/03/Marcus.pdf. Accessed 02th November 2017
Markowicz Bastos D, Monaro E, Siguemoto E, Séfora M (2012) Maillard reaction products in processed food: pros and cons. In: Valdez B (ed) Food industrial processes—methods and equipment. InTech, Rijeka. https://doi.org/10.5772/31925. Available https://www.intechopen.com/books/food-industrial-processes-methods-and-equipment/maillard-reaction-products-in-processed-food-pros-and-cons. Accessed 07 Nov 2017
Martins SIFS, Jongen WMF, van Boekel MAJS (2001) A review of Maillard reaction in food and implications to kinetic modelling. Trends Food Sci Technol 11(9–10):364–373. https://doi.org/10.1016/s0924-2244(01)00022-x
Mathlouthi M (1994) Food packaging and preservation. Springer Science & Business Media, Dordrecht
McWeeny DJ, Knowels ME, Hearne JF (1974) The chemistry of non-enzymic browning and its control by sulphites. J Sci Food Agric 25(6):735–746. https://doi.org/10.1002/jsfa.2740250616
Morales FJ (2008) Hydroxymethylfurfural (HMF) and related com-pounds. In: Stadler RH and Lineback DR (eds) Process-induced food toxicants: occurrence, formation, mitigation, and health risks. Wiley, Hoboken. https://doi.org/10.1002/9780470430101.ch2e
Morales V, Sanz ML, Martín-Álvarez PJ, Corzo N (2009) Combined use of HMF and furosine to assess fresh honey quality. J Sci Food Agric 89(8):1332–1338. https://doi.org/10.1002/jsfa.3590
Parisi S (2017) Antimicrobials in foods today and the role of chitosan—current hopes and new perspectives. Glob Drugs Therap 2(2):1–2. https://doi.org/10.15761/GDT.1000114
Pastoriza S, Rufián-Henares JÁ, García-Villanova B, Guerra-Hernández E (2016) Evolution of the Maillard reaction in glutamine or arginine-dextrinomaltose model systems. Foods 5(4):86. https://doi.org/10.3390/foods5040086
Perra F, Porcu M, Sanjust MT, Spanedda L (2002) Determinazione della furosina in prodotti lattiero-caseari ovini. Riv Sci Aliment 31(2):165–178
Resmini P, Pellegrino L, Cattaneo S (2003) Furosine and other heat-treatment indicators for detecting fraud in milk and milk products. Ital J Food Sci 15(4):473–484
Rufián-Henares JA, Delgado-Andrade C, Morales FJ (2009) Assessing the Maillard reaction development during the toasting process of common flours employed by the cereal products industry. Food Chem 114, 1:93–99. https://doi.org/10.1016/j.foodchem.2008.09.021
Sharma RK, Parisi S (2017) Aflatoxins in Indian food products. In: Sharma RK, Parisi S (eds) Toxins and contaminants in Indian food products. Springer International Publishing AG, Cham. https://doi.org/10.1007/978-3-319-48049-7_2
Schmidt A, Boitz LI, Mayer HK (2016) A new UHPLC method for the quantitation of furosine as heat load indicator in commercial liquid milk. J Food Compos Anal 56:104–109. https://doi.org/10.1016/j.jfca.2016.12.014
Soria AC, Villamiel M (2012) Non‐enzymatic browning in cookies, crackers and breakfast cereals. In: Simpson BK (ed) Food biochemistry and food processing, 2nd edn, pp 584–593. https://doi.org/10.1002/9781118308035.ch30
Sun DW (ed) (2016) Handbook of frozen food processing and packaging. CRC Press, Boca Raton. https://doi.org/10.1201/9781420027402
Tirelli A, Pellegrino L (1995) Determination of furosine in dairy products by capillary zone electrophoresis: a comparison with the HPLC method. Ital J Food Sci 7(4):379–385
Tornuk F, Karaman S, Ozturk I, Toker OS, Tastemur B, Sagdic O, Dogan M, Kayacier A (2013) Quality characterization of artisanal and retail Turkish blossom honeys: determination of physico-chemical, microbiological, bioactive properties and aroma profile. Ind Crop Prod 46:124–131. https://doi.org/10.1016/j.indcrop.2012.12.042
Tressl R, Nittka C, Kersten E (1995) Formation of Isoleucine-specific Maillard Products from [1-13C]-d-glucose and [1-13C]-d-fructose. J Agric Food Chem 43(5):1163–1169. https://doi.org/10.1021/jf00053a009
Van Boekel MAJS (1998) Effect of heating on Maillard reactions in milk. Food Chem 62(4):403–414. https://doi.org/10.1016/S0308-8146(98)00075-2
Van Boekel MAJS, Brands C (1998) Heating of sugarcasein solutions: isomerization and Maillard reactions. In: O’Brien J, Nursten HE, Crabbe MJC, Ames JM (eds) The Maillard reaction in foods and medicine. Royal Society of Chemistry, Cambridge, pp 154–158
Velásquez Cifuentes NF (2013) Evaluación de diferentes tiempos de calentamiento de la miel de abeja (Apis mellifera) para retardar su cristalización y determinar los niveles de HMF (Hidroximetil Furfural), en la asociación de apicultores del sur occidente de Guatemala. Dissertation, Universidad de San Carlos de Guatemala
Vhangani LN, Van Wyk J (2016) Antioxidant activity of Maillard reaction products (MRPs) in a lipid-rich model system. Food Chem 208:301–308. https://doi.org/10.1016/j.foodchem.2016.03.100
Wilkinson C, Dijksterhuis GB, Minekus M (2000) From food structure to texture. Trends Food Sci Technol 11(12):442–450. https://doi.org/10.1016/s0924-2244(01)00033-4
Yada RY, Bryksa B, Nip WK (2012) An introduction to food biochemistry. In: Simpson BK (ed) Food biochemistry and food processing, 2nd edn, pp 1–25. https://doi.org/10.1002/9781118308035.ch1
Zaccheo A, Palmaccio E, Venable M, Locarnini-Sciaroni I, Parisi S (2017) The complex relationships between humans, food, water, and hygiene. In: Zaccheo A, Palmaccio E, Venable M, Locarnini-Sciaroni I, Parisi S (eds) Food hygiene and applied food microbiology in an anthropological cross cultural perspective. Springer International Publishing, Cham. https://doi.org/10.1007/978-3-319-44975-3_1
Zardetto S, Dalla Rosa M, Di Fresco S (2003) Effects of different heat treatment on the furosine content in fresh filata pasta. Food Res Int 36(9–10):877–883. https://doi.org/10.1016/S0963-9969(03)00096-6
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Singla, R.K., Dubey, A.K., Ameen, S.M., Montalto, S., Parisi, S. (2018). Analytical Methods for the Determination of Furosine in Food Products. In: Analytical Methods for the Assessment of Maillard Reactions in Foods. SpringerBriefs in Molecular Science(). Springer, Cham. https://doi.org/10.1007/978-3-319-76923-3_3
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