Reactivity of epicatechin in aqueous glycine and glucose Maillard reaction models: Quenching of C 2, C 3, and C 4 sugar fragments

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 10, 2005, Pages 4130-4135

  Totlani, Vandana M ^a   Peterson, Devin G ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Epicatechin; Inhibit; Maillard reaction; Nonenzymatic browning; Polyphenolic; Reactivity; Sugar fragments

Indexed keywords

CATECHIN; GLUCOSE; GLYCINE; WATER;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; GAS CHROMATOGRAPHY; GLYCATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; SOLUTION AND SOLUBILITY;

CATECHIN; CHROMATOGRAPHY, GAS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLUCOSE; GLYCINE; MAILLARD REACTION; MASS SPECTROMETRY; MODELS, CHEMICAL; SOLUTIONS; WATER;

EID: 20844446841     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf050044x     Document Type: Article

References (26)

1. Namiki, M. Chemistry of Maillard reaction: Recent studies on the browning reaction mechanism and the development of antioxidants and mutagens. Adv. Food Res. 1988, 32, 115-184.
2. Mauron, J. The Maillard reaction in foods: A critical review from nutritional standpoint. Prog. Food Nutr. Sci. 1981, 5, 5-35.
3. Hodge, J. E. Dehydrated foods: Chemistry of browning reactions in model systems. J. Agric. Food Chem. 1953, 1, 928-943.
4. Hofmann, T. Studies on the relationship between 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. 1998, 46, 3891-3895.
5. Ames, J. M. Applications of the Maillard reaction in the food industry. Food Chem. 1998, 62, 431-439.
6. van Boekel, M. A. J. S. Kinetic aspects of the Maillard reaction: A critical review. Nahrung/Food 2001, 45, 150-159.
7. Shibamoto, T.; Bernhard, R. A. Effect of time, temperature, and reactant ratio on pyrazine formation in model systems. J. Agric. Food Chem. 1976, 24, 847-851.
8. Renn, P. T.; Sathe, S. K. Effects of pH, temperature, and reactant molar ratio on L-leucine and D-glucose Maillard browning reaction in an aqueous system. J. Agric. Food Chem. 1997, 45, 3782-3787.
9. Ames, J. M. Control of the Maillard reaction in food systems. Trends Food Sci. Technol. 1990, 150-154.
10. Wang, Y. Effects of naturally occurring phenolic compounds on the formation of Maillard aromas. Ph.D. Dissertation, Rutgers State University, 2000.
11. Counet, C.; Ouwerx, C.; Rosoux, S.; Collin, S. Relationship between procyanidins and flavor contents of cocoa liquors from different origins. J. Agric. Food Chem. 2004, 52, 6243-6249.
12. Cros, E. Recherche d'un indice de fermentation du cacao. III. Evolution des flavan-3-ols de la feve. Cafe, Cacao, The 1989, 165-170.
13. Zak, D. K.; Keeney, P. G. Extraction and fractionation of cocoa proteins as applied to several varieties of cocoa beans. J. Agric. Food Chem. 1976, 24, 479-483.
14. Peterson, D. G.; Totlani, V. M. Influence of flavonoids on the thermal generation of aroma compounds. In Phenolics in Foods and Natural Health Products; Ho, C. T., Shahidi, F., Eds.; ACS Symposium Series; American Chemical Society: Washington, DC; in press.
15. Colahan-Sederstrom, P. M.; Peterson, D. G. Inhibition of key aroma compound generated during ultra-high temperature processing of bovine milk via epicatechin addition. J. Agric. Food Chem. 2005, 53, 398-402.
16. Yaylayan, V. A.; Keyhani, A. Origin of 2,3-pentanedione and 2,3-butanedione in D-glucose/L-alanine Maillard model systems. J. Agric. Food Chem. 1999, 47, 3280-3284.
17. 13C] glycine or proline. In Process Induced Chemical Changes in Food; Shahidi, F., Ho, C. T., Eds.; Plenum Press: New York, 1998; pp 237-244.
18. Amrani-Hemaimi, M.; Cerny, C.; Fay, L. B. Mechanisms of formation of alkylpyrazines in the Maillard reaction. J. Agric. Food Chem. 1995, 43, 2818-2822.
19. Cerny, C.; Davidek, T. Formation of aroma compounds from ribose and cysteine during the Maillard reaction. J. Agric. Food Chem. 2003, 51, 2714-2721.
20. Schieberle, P.; Fischer, R.; Hofmann, T. The carbohydrate modul labelling technique - A useful tool to clarify formation pathways of aroma compounds formed in Maillard-type reactions. In Flavour Research at the Dawn of the Twenty-first Century; Le Quéré, J. L., Etiévant, P. X., Eds.; Lavoisier: Paris, France, 2003; pp 447-452.
21. Hashimoto, F.; Nonaka, G.; Nishioka, I. Tannins and related-compounds.90. 8-c-ascorbyl (-)-epigallocatechin 3-o-gallate and novel dimeric flavan-3-ols, oolonghomobisflavan-a and olong-homobisflavan-b, from oolong tea. Chem. Pharm. Bull. 1989, 37, 3255-3263.
22. Fulcrand, H.; Es-Safi, N.; Cheynier, V.; Moutounet, M. Study of acetaldehyde induced polymerization of flavan-3-ols by liquid chromatography-ion spray mass spectrometry. J. Chromatogr. 1996, 752, 85-91.
23. Es-Safi, N.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Competition between (+)-catechin and (-)-epicatechin in acetaldehyde-induced polymerization of flavanols. J. Agric. Food Chem. 1999, 47, 2088-2095.
24. Saucier, C.; Bourgeois, G.; Vitry, C.; Roux, M.; Glories, Y. Characterization of (+)-catechin-acetaldehyde polymers: A model for colloidal state of wine polyphenols. J. Agric. Food Chem. 1997, 45, 1045-1049.
25. Namiki, M.; Hayashi, T. Developments of novel free radicals during the amino-carbonyl reactions of sugars with amino acid. J. Agric. Food Chem. 1975, 23, 487-491.
26. Hayashi, T.; Namiki, M. On the mechanism of free radical formation during browning reactions of sugars with amino compounds. Agric. Biol. Chem. 1981, 45, 933-939.