Formation of aroma compounds from ribose and cysteine during the Maillard reaction

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 9, 2003, Pages 2714-2721

  Cerny, Christoph ^a,b   Davidek, Tomas ^a  

^a NESTLÉ RESEARCH CENTER   (Switzerland)

^b Analysis and Perception Department   (Switzerland)

Author keywords

2 Furfurylthiol; 2 Mercapto 3 pentanone; 2 Methyl 3 furanthiol; 3 Mercapto 2 pentanone; 4 Hydroxy 5 methyl 3(2H) furanone; 13C5 ribose; Cysteine; Maillard reaction; Ribose; Solid phase microextraction; Stable isotope labeling

Indexed keywords

2 BUTANONE; 2 FURFURYLTHIOL; 2 METHYL 3 FURANTHIOL; 3 MERCAPTO 2 BUTANONE; 3 MERCAPTO 2 PENTANONE; 3 THIOPHENETHIOL; 4 HYDROXY 5 METHYL 3(2H) FURANONE; ALKANONE; CARBON; CYSTEINE; CYSTEINE DERIVATIVE; FURANONE DERIVATIVE; RIBOSE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG; VOLATILE AGENT;

AROMA; ARTICLE; ATOM; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; GLYCATION; HEATING; ISOMER; ISOTOPE LABELING; MASS SPECTROMETRY; PH MEASUREMENT; REACTION ANALYSIS; SOLID PHASE MICROEXTRACTION; SYNTHESIS;

CARBON ISOTOPES; CYSTEINE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MAILLARD REACTION; ODORS; RIBOSE; VOLATILIZATION;

EID: 0037462026     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf026123f     Document Type: Article

References (42)

1. Morton, I. D.; Akroyd, P.; May, C. G. Flavoring substances. U.S. Patent 2934437, 1960.
2. Gasser, U.; Grosch, W. Identification of volatile flavor compounds with high aroma values from cooked beef. Z. Lebensm. Unters. Forsch. 1988, 186, 489-494.
3. Evers, W. J.; Heinsohn, H. H., Jr.; Mayers, B. J.; Sanderson, A. Furans substituted at the three position with sulfur. In Phenolic, Sulfur and Nitrogen Compounds in Food Flavors; Charalambous, G., Katz, I., Eds.; American Chemical Society: Washington, DC, 1976; pp 184-193.
4. Gasser, U.; Grosch, W. Primary odorants of chicken broth. A comparative study with meat broths from cow and ox. Z. Lebensm. Unters. Forsch. 1990, 190, 3-8.
5. Gasser, U.; Grosch, W. Aroma extract dilution analysis of commercial meat flavorings. Z. Lebensm. Unters. Forsch. 1990, 190, 511-515.
6. Farmer, L. J.; Mottram, D. S. Recent studies on the formation of meat-like aroma compounds. In Flavour Science and Technology; Bessiere, Y., Thomas, A. F., Eds.; Wiley: Chichester, U.K., 1990; pp 113-116.
7. Farmer, L. J.; Mottram, D. S.; Whitfield, F. B. Volatile compounds produced in Maillard reactions involving cysteine, ribose and phospholipid. J. Sci. Food Agric. 1989, 49, 347-368.
8. Hofmann, T.; Schieberle, P. Evaluation of the key odorants in a thermally treated solution of ribose and cysteine by aroma extract dilution techniques. J. Agric. Food Chem. 1995, 43, 2187-2194.
9. Mulders, E. J. Volatile components from the nonenzymic browning reaction of the cysteine/cystine-ribose system. Z. Lebensm. Unters. Forsch. 1973, 152, 193-201.
10. Whitfield, F. B.; Mottram, D. S.; Brock, S.; Puckey, D. J.; Salter, L. J. Effect of phospholipid on the formation of volatile heterocyclic compounds in heated aqueous solutions of amino acids and ribose. J. Sci. Food Agric. 1988, 42, 261-272.
11. Guentert, M.; Bertram, H. J.; Hopp, R.; Silberzahn, W.; Sommer, H.; Werkhoff, P. Thermal generation of flavor compounds from thiamin and various amino acids. In Recent Developments in Flavor and Fragrance Chemistry; Hopp, R., Mori, K., Eds.; VCH: Weinheim, Germany, 1993; pp 215-240.
12. Misharina, T. A.; Golovnya, R. V. Sulfur-containing compounds in meat aroma model systems. Abh. Ak-ad. Wiss. DDR, Abt. Math., Naturwiss., Tech. 1988, 115-127.
13. Grosch, W.; Zeiler-Hilgart, G.; Cerny, C.; Guth, H. Studies on the formation of odorants contributing to meat flavors. In Progress in Flavor Precursors Studies; Schreier, P., Winterhalter, P., Eds.; Allured Publishing: Carol Stream, IL, 1993; pp 329-342.
14. Mottram, D. S.; Nobrega, I. C. C. Formation of sulfur aroma compounds in reaction mixtures containing cysteine and three different forms of ribose. J. Agric. Food Chem. 2002, 50, 4080-4086.
15. Hofmann, T. Characterization of intense odorants in carbohydrate/cysteine model reactions and elucidation of formation pathways. Ph.D Dissertation, Technical University Munich, 1995 (in German).
16. Mottram, D. S.; Madruga, M. S.; Whitfield, F. B. Some novel meatlike aroma compounds from the reactions of alkanediones with hydrogen sulfide and furanthiols. J. Agric. Food Chem. 1995, 43, 189-193.
17. Shibamoto, T. Formation of sulfur- and nitrogen-containing compounds from the reaction of furfural with hydrogen sulfide and ammonia. J. Agric. Food Chem. 1977, 25, 206-208.
18. Severin, T.; Seilmeier, W. Maillard reaction. II. Reaction of pentoses in the presence of amine acetates. Z. Lebensm. Unters. Forsch. 1967, 134, 230-232 (in German).
19. Van den Ouweland, G. A. M. Components contributing to beef flavor. Volatile compounds produced by the reaction of 4-hydroxy-5-methyl-3(2H)-furanone and its thio analog with hydrogen sulfide. J. Agric. Food Chem. 1975, 23, 501-505.
20. Whitfield, F.; Mottram, D. S. Heterocyclic volatiles formed by heating cysteine or hydrogen sulfide with 4-hydroxy-5-methyl-3(2H)-furanone at pH 6.5. J. Agric. Food Chem. 2001, 49, 816-822.
21. Whitfield, F. B.; Mottram, D. S. Investigation of the reaction between 4-hydroxy-5-methyl-3(2H)-furanone and cysteine or hydrogen sulfide at pH 4.5. J. Agric. Food Chem. 1999, 47, 1626-1634.
22. Schieberle, P. Quantitative analysis of aroma compounds in wheat and rye bread crusts using a stable isotope dilution assay. J. Agric. Food Chem. 1987, 35, 252-257.
23. Koehler, P. E.; Mason, M. E.; Newell, J. A. Formation of pyrazine compounds in sugar - amino acid model systems. J. Agric. Food Chem. 1969, 17, 393-396.
24. Hofmann, T.; Schieberle, P. Acetylformoin - an important progenitor of 4-hydroxy-2,5-dimethyl-3(2H)-furanone and 2-acetyltetrahydropyridine during thermal food processing. In Flavour 2000; Rothe, M., Ed.; Eigenverlag: Bergholz-Rehbrücke, Germany, 2001; pp 311-322.
25. Schieberle, P.; Bareth, A.; Fischer, R.; Hofmann, T. The carbohydrate modul labeling-technique - A useful tool to clarify formation pathways of key aroma and taste compounds formed in Maillard-type reactions. Book of Abstracts, 10th Weurman Flavour Research Symposium, Beaune, France, June 24-28; INRA: Dijon, France, 2002; Abstract 025.
26. 13C-labeling experiments. J. Agric. Food Chem. 2002, 50, 6027-6036.
27. Gry, J. Guidelines for Safety Evaluation of Thermal Process Flavourings; Council of Europe Publishing: Strasbourg, France, 1995.
28. Hofmann, T.; Schieberle, P. Quantitative model studies on the effectiveness of different precursor systems in the formation of the intense food odorants 2-furfurylthiol and 2-methyl-3-furanthiol. J. Agric. Food Chem. 1998, 46, 235-241.
29. Silwar, R.; Tressl, R. Gas chromatographic-mass spectrometric investigation of aroma compounds formed in the cysteine-methionine-furfural model system under roasting conditions. Z. Lebensm. Unters. Forsch. 1989, 189, 205-211.
30. Nobrega, I. C. C.; Mottram, D. S. The formation of meaty aroma compounds in cysteine model systems containing ribose 5-phosphate or ribose. In Frontiers of Flavour Science; Schieberle, P., Engel, K. H., Eds.; DFA: Garching, Germany, 2000; pp 487-491.
31. Mottram, D. S. Flavour formation in meat and meat products: a review. Food Chem. 1998, 62, 415-424.
32. Nedvidek, W.; Ledl, F.; Fischer, P. Detection of 5-hydroxymethyl-2-methyl-3(2H)-furanone and of α-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines. Z. Lebensm. Unters. Forsch. 1992, 194, 222-228.
33. De Kimpe, N.; Georgieva, A.; Boeykens, M.; Lazar, L. Synthesis of laurencione, a labile dihydro-3(2H)-furanone derivative from the red alga Laurencia spectabilis. J. Org. Chem. 1995, 60, 5262-5265.
34. De Kimpe, N.; Georgieva, A.; Boeykens, M.; Kozekov, I.; Aelterman, W. New formal syntheses of laurencione, a labile dihydrofuranone derivative from the red alga Laurencia spectabilis. Synthesis 1995, 1131-1134.
35. Bernart, M. W.; Gerwick, W. H.; Corcoran, E. E.; Lee, A. Y.; Clardy, J. Laurencione, a heterocycle from the red alga Laurencia spectabilis. Phytochemistry, 1992, 31, 1273-1276.
36. Glomb, M. A.; Pfahler, C.; Hiller, R. Reductones participate in redox-reactions during amine catalyzed sugar degradation. In The Maillard Reaction in Food Chemistry and Medical Science: Update for The Postgenomic Era; Horiuchi, S., Taniguchi, N., Hayase, F., Kurata, T., Osawa, T., Eds.; Elsevier Science: Amsterdam, The Netherlands, 2002; pp 201-202 (Japan Maillard Reaction Society: Kumamoto, Japan, 2001; Abstract F01-002).
37. Hollnagel, A.; Krol, L. W. Degradation of oligosaccharides in nonenzymatic browning by formation of α-dicarbonyl compounds via a "peeling off" mechanism. J. Agric. Food Chem. 2000, 48, 6219-6226.
38. Sakaguchi, M.; Shibamoto, T. Formation of heterocyclic compounds from the reaction of cysteamine and D-glucose, acetaldehyde, or glyoxal. J. Agric. Food Chem. 1978, 26, 1179-1183.
39. Shu, C.-K.; Hagedorn, M. L.; Mookherjee, B. D.; Ho, C.-T. pH effect on the volatile components in the thermal degradation of cysteine. J. Agric. Food Chem. 1985, 33, 442-446.
40. Hofmann, T.; Schieberle, P.; Grosch, W. Model studies on the oxidative stability of odor-active thiols occurring in food flavors. J. Agric. Food Chem. 1996, 44, 251-255.
41. Van Seeventer, P. B.; Weenen, H.; Winkel, C.; Kerler, J. Stability of thiols in an aqueous process flavoring. J. Agric. Food Chem. 2001, 49, 4292-4295.
42. Biemel, K. M.; Conrad, J.; Lederer, M. O. Unexpected carbonyl mobility in aminoketose: the key to major Maillard crosslinks. Angew. Chem., Int. Ed. Engl. 2002, 41, 801-804.