Abstract
To obtain basic information about the extent of the early Maillard reaction in commercially available cheese varieties of varying degrees of maturity, Amadori products (APs) formed between reducing sugars and the ε-amino group of lysine (ε-APs) or the α-amino of selected amino acids (α-APs) were analyzed. APs were determined as the corresponding N-(2-furoylmethyl) amino acids (FMAAs) after acid hydrolysis using RP–HPLC with UV-detection as well as mass spectroscopy. Identification of the FMAAs resulting from the α-APs of lysine, valine, leucine, and isoleucine was achieved for the first time for cheese samples. The content of furosine, which is a hallmark for ε-APs, ranged from to 3–75 mg/100 g protein corresponding to 24–591 μmol ε-AP/100 g protein. ε-AP levels declined during ripening in all investigated cheeses, depending on the cheese type and stage of maturation. The mean content of four α-APs ranged from 138 to 681 μmol/100 g protein. Lowest concentrations were found in long-term ripened cheese samples, indicating a putative degradation of α-APs and ε-APs during advanced stages of maturation. The ratio of α-APs to ε-APs might be a useful indicator of cheese ripening.
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Abbreviations
- APs:
-
Amadori products
- FMAA:
-
N-(2-furoylmethyl)amino acid
- OPA-assay:
-
o-Phthaldialdehyde assay
- TCA-N:
-
Non-protein nitrogen/trichloro acetic acid soluble nitrogen
- WS-N:
-
Water soluble nitrogen
- DNA-assay:
-
Dinitrosalicylic acid assay
- AGEs:
-
Advanced glycation endproducts
- DM:
-
Dry matter
- PCC:
-
Pearson correlation coefficients
References
McSweeney PLH, Sousa MJ (2000) Biochemical pathways for the production of flavour compounds in cheeses during ripening: a review. Lait 80:293–324
Marilley MG, Casey L (2004) Flavours of cheese products: metabolic pathways, analytical tools and identification of producing strains. Int J Food Microbiol 90:139–159
Bley ME, Johnson ME, Olson NF (1985) Factors affecting nonenzymatic browning of process cheese. J Dairy Sci 68:555–561
Finot PA, Mauron J (1972) Le blocage de la lysine par la reaction de Maillard II. Proprietes chimiques des derives N-(desoxy-1-d-fructosyl-1) et N-(desoxy-1-d-lactulosyl-1) de la lysine. Helv Chim Acta 55:1153–1164
Henle T (2005) Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in foods. Amino Acids 29:313–322
Ledl F, Schleicher E (1990) Die Maillard-Reaktion in Lebensmitteln und im menschlichen Körper—neue Ergebnisse zu Chemie, Biochemie und Medizin. Angew Chem 102:597–626
Mottram DS (2002) Acrylamide is formed in the Maillard reaction. Nature 419:448
Van Boekel MAJS (1998) Effect of heating on Maillard reactions in milk. Food Chem 62:403–414
Takeuchi M, Yamagishi S (2004) TAGE (toxic AGEs) hypothesis in various chronic diseases. Med Hypotheses 63:449–452
Finot PA, Deutsch R, Bujard E (1981) The extent of the Maillard reaction during the processing of milk. Prog Food Nutr Sci 5:345–355
Perra E, Porcu M, Sanjust MT, Spanedda L (2002) Determination of furosine in sheep dairy products. Rivista di Scienza dell’Alimentazione 31:165–178
Barbagallo RN, Lupo M, Tomaselli F (1998) Furosine as thermal damage marker in mozzarella-cheese from Sicily. Industrie Alimentari 37:614–617
Villamiel M, Arias M, Corzo N, Olano A (2000) Survey of furosine content of cheeses marketed in spain. J Food Prot 63:974–975
Ficcadenti A, Perra F, Porcu M, Spanedda L (2005) Determination of furosine in ovine milk and cheese products. Rivista di Scienza dell’ Álimentazione 34:61–69
Corzo N, Villamiel M, Arias M, Jiménez-Pérez S, Morales FJ (2000) The Maillard reaction during the ripening of Manchego cheese. Food Chem 71:255–258
Krause R, Knoll K, Henle T (2003) Studies on the formation of furosine and pyridosine during acid hydrolysis of different Amadori products of lysine. Eur Food Res Technol 216:277–283
Penndorf I, Biedermann D, Maurer SV, Henle T (2007) Studies on N-terminal glycation of peptides in hypoallergenic infant formulas: quantification of α-N-(2-furoylmethyl) amino acids. J Agric Food Chem 55:723–727
del Castillo MD, Villamiel M, Olano A, Corzo N (2000) Use of 2-Furoylmethyl derivatives of GABA and arginine as indicators of the initial steps of Maillard reaction in orange juice. J Agric Food Chem 46:4217–4220
Sanz ML, del Castillo MD, Corzo N, Olano A (2001) Formation of Amadori compounds in dehydrated fruits. J Agric Food Chem 49:5228–5231
Sanz ML, del Castillo MD, Corzo N, Olano A (2000) Presence of 2-furoylmethyl derivatives in hydrolysates of processed tomato products. J Agric Food Chem 48:468–471
Sanz ML, del Castillo MD, Corzo N, Olano A (2003) 2-Furoylmethyl amino acids and hydroxymethylfurfural as indicators of honey quality. J Agric Food Chem 51:4278–4283
Miller GL (1959) Use of dinitrosalicylic acid reagent for determination of reducing sugar. Anal Chem 31:426–428
Resmini P, Pellegrino L, Batelli G (1990) Accurate quantification of furosine in milk and dairy products by a direct HPLC method. Ital J Food Sci 3:173–183
Rohm H, Tschager E, Jaros D (1996) Determination of proteolysis in Swiss cheese: comparison of the Kjeldahl method and a spectrophotometric OPA Assay. Lebensm Wiss Technol 29:191–194
Henle T, Walter H, Krause I, Klostermeyer H (1991) Efficient determination of individual Maillard compounds in heat-treated milk products by amino acid analysis. Int Dairy J 1:125–135
Resmini P, Pellegrino L (1991) Analysis of food heat damage by direct HPLC of furosine. Int Chromatogr Lab 6:7–11
Tirelli A (1998) Improved method for the determination of furosine in food by capillary electrophoresis. J Food Prot 61:1400–1404
Tokuşoğlu Ö, Akalin AS, Unal K (2006) Rapid high performance liquid chromatographic detection of furosine (ε-N-2-furoylmethyl-l-lysine) in yoghurt and cheese marketed in turkey. J Food Qual 29:38–46
Schwietzke U, Schwarzenbolz U, Henle T (2009) Influence of cheese type and maturation time on the early Maillard reaction in cheese. Czech J Food Sci 27:140–142
Belitz HD, Grosch, W, Schieberle P (2001) Lehrbuch der Lebensmittelchemie, 5th edn. Springer, Berlin
Henle T, Zehetner G, Klostermeyer H (1995) Fast and sensitive determination of furosine. Z Lebensm Unters Forsch 200:235–237
Villamiel M, Arias M, Corzo N, Olano A (1999) Use of different thermal indices to assess the quality of pasteurized milks. Z Lebensm Unters Forsch 208:169–171
Saint Gelais D, Doyon G, Rolland JR, Goulet J (1991) Sugar and organic acid concentrations during ripening of Cheddar cheese-like products. Milchwissenschaft 46:288–291
Acknowledgments
We like to thank Mrs. Karla Schlosser for performing the amino acid analysis and Dr. Uwe Schwarzenbolz for his help during the LC–ESI–TOF–MS measurements.
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Schwietzke, U., Malinowski, J., Zerge, K. et al. Quantification of Amadori products in cheese. Eur Food Res Technol 233, 243–251 (2011). https://doi.org/10.1007/s00217-011-1509-6
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DOI: https://doi.org/10.1007/s00217-011-1509-6