4-Alkylidene-2-imino-5-[4-alkylidene-5-oxo-1,3-imidazol-2-inyl] azamethylidene-1,3-imidazolidine - A Novel Colored Substructure in Melanoidins Formed by Maillard Reactions of Bound Arginine with Glyoxal and Furan-2-carboxaldehyde

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 10, 1998, Pages 3896-3901

  Hofmann, Thomas ^a  

^a DEUTSCHE FORSCHUNGSANSTALT FÜR LEBENSMITTELCHEMIE   (Germany)

Author keywords

Arginine; Colored compounds; Cross link amino acid; Furan 2 carboxaldehyde; Glyoxal; Maillard reaction; Melanoidins

Indexed keywords

EID: 0001713288     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980396m     Document Type: Article

References (16)

1. Ames, J. M. The Maillard reaction. In Progress in Food Proteins - Biochemistry; Hudson, B. J. F., Ed.; Elsevier Applied Science: London, 1992; pp 99-153.
2. Aurich, H.; Hofmann, R.; Klöcking, R.; Mücke, D. Compounds with huminic acids characteristics in roast coffee extracts. Amino acid contents of coffee-huminic acids (in German). Z. Lebensm. Unters. Forsch. 1967, 135, 59-64.
3. Hirayama, T.; Yamada, N.; Nohara, M.; Jukui, S. The existence of the 1,2-dicarbonyl compounds glyoxal, methyl glyoxal and diacetyl in autoxidised edible oils. J. Sci. Food Agric. 1984, 35, 1357-1362.
4. Hofmann, T. Determination of the chemical structure of novel coloured compounds generated by Maillard-type reactions. In Proceedings of the 6th International Symposium on the Maillard Reaction; O'Brien, J., Nursten, H. E., Crabbe, M. J. C., Ames, J. M., Eds.; Royal Society of Chemistry: Cambridge, U.K., 1997a; in press.
5. Hofmann, T. Determination of the chemical structure of novel colored 1H-pyrrol-3(2H)-one derivatives formed by Maillard-type reactions. Helv. Chim. Acta 1997b, 80, 1843-1856.
6. Hofmann, T. Studies on the relationship between the molecular weight and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentrifugation and color dilution techniques. J. Agric. Food Chem. 1998a, 46, 3891-3895.
7. Hofmann, T. Studies on melanoidin-type colorants generated from the Maillard reaction of protein-bound lysine and furan-2-carboxaldehyde - chemical characterisation of a red coloured domaine. Z. Lebensm. Unters. Forsch. 1998b, 206, 251-258.
8. Kanjahn, D.; Jarms, U.; Maier, H. G. Hydroxymethylfurfural and furfural in coffee and related beverages. Dtsch. Lebensm. Rundsch, 1996, 92, 328-331.
9. Ledl, F.; Schleicher, E. The Maillard reaction in food and in the human body - new results in chemistry, biochemistry and medicine. Angew. Chem. 1992, 102, 597-626.
10. Nedvidek, W.; Ledl, F.; Fischer, P. Detection of 5-hydroxymethyl-2-methyl-3(2H)-furanone and of a-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines. Z. Lebensm. Unters. Forsch. 1992, 194, 222-228.
11. Nursten, H. E.; O'Reilly, R. Coloured compounds formed by the interaction of glycine and xylose. Food Chem. 1986, 20, 45-60.
12. Okitani, A.; Cho, R. K.; Kato, H. Polymerization of lysozyme and impairment of its amino acid residues caused by reaction of glucose. Agric. Biol. Chem. 1984, 48, 1801-1808.
13. Schieberle, P.; Grosch, W. Evaluation of the flavour of wheat and rye bread crusts by aroma extract dilution analysis. Z. Lebensm. Unters. Forsch. 1987, 185, 111-113.
14. Schwarzenbolz, U.; Henle, Th.; Haessner, R.; Klostermeyer, H. On the reaction of glyoxal with proteins. Z. Lebensm. Unters. Forsch. 1997, 205, 121-124.
15. Tressl, R.; Wondrak, G. T.; Krüger, R.-P.; Rewicki, D. New melanoidin-like Maillard polymers from 2-deoxypentoses. J. Agric. Food Chem. 1998a, 46, 104-110.
16. Tressl, R.; Wondrak, G. T.; Garbe, L.-A.; Rewicki, D.; Krüger, R.-P. Pentoses and hexoses as sources of new melanoidin-like Maillard polymers. J. Agric. Food Chem. 1998b, 46, 1765-1776.