(+)-Catechin-aldehyde condensations: Competition between acetaldehyde and glyoxylic acid

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 19, 2005, Pages 7552-7558

  Drinkine, Jessica ^a   Glories, Yves ^a   Saucier, Cédric ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Acetaldehyde; Condensation; Flavanols; Glyoxylic acid; LC ESI MS; LC UV; Phenolic compounds

Indexed keywords

EID: 26244434334     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0504723     Document Type: Article

References (25)

1. Santos-Buelga, C.; Scalbert, A. Proanthocyanidins and tannin-like compounds-nature, occurrence, dietary intake and effects on nutrition and health. J. Sci. Food Agric. 2000, 80, 1094-1117.
2. Llaudy, M.; Canals, R.; Canals, J. M.; Rozéz, N.; Arola, L.; Zamora, F. New method for evaluating astringency in red wine. J. Agric. Food Chem. 2004, 52, 742-746.
3. Saucier, C.; Bourgeois, G.; Vitry, C.; Roux, D.; Glories, Y. Characterization of (+)-catechin-acetaldehyde polymers: a model for colloidal state of wine polyphenols. J. Agric. Food Chem. 1997, 45, 1045-1049.
4. Vidal, S.; Cartalade, D.; Souquet, J.-M.; Fulcrand, H.; Cheynier, V. Changes in procyanidin chain length in winelike model solutions. J. Agric. Food Chem. 2002, 50, 2261-2266.
5. Boulton, R. The copigmentation of anthocyanins and its role in the color of red wine: a critical review. Am. J. Enol. Vitic. 2001, 52, 67-82.
6. Liao, H.; Cai, Y.; Haslam, E. Polyphenol interactions. Anthocyanins: co-pigmentation and colour changes in red wines. J. Sci. Food Agric. 1992, 59, 299-305.
7. Prieur, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. Oligomeric and polymeric procyanidins from grape seeds. Photochemistry 1994, 36, 781-784.
8. Haslam, E. In vino veritas: oligomeric procyanidins and the aging of red wines. Phytochemistry 1980, 19, 2577-2582.
9. Jurd, L. Review of polyphenol condensation reactions and their possible occurrence in the aging of wines. Tetrahedron 1969, 25, 2367-2380.
10. Timberlake, C. F.; Bridle, P. Anthocyanins: color augmentation with catechin and acetaldehyde. J. Sci. Food Agric. 1977, 26, 539-544.
11. Es-Safi, N.; Cheynier, V.; Moutounet, M. Implication of phenolic compounds in food organoleptic properties. J. Food Compos. Anal. 2003, 16, 535-553.
12. Es-Safi, N.; Le Guenervé, C.; Cheynier, V.; Moutounet, M. New phenolic compounds obtained by evolution of (+)-catechin and glyoxylic acid in hydroalcoholic medium. Tetrahedron Lett. 2000, 41, 1917-1921.
13. 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.
14. Fulcrand, H.; Cheynier, V.; Oszmianski, J.; Moutounet, M. An oxidized tartaric residue as a new bridge potentially competing with acetaldehyde in flavan-3-ol condensation. Phytochemistry 1997, 46, 233-227.
15. Saucier, C.; Guerra, C.; Laguerre, M.; Glories, Y. (+)-catechin- acetaldehyde condensation products in relation with wine-ageing. Phytochemistry 1997, 46, 229-234.
16. Romano, P.; Suzzi, G.; Turbanti, L.; Polsinelli, M. Acetaldehyde production in Saccharomyces cerevisiae wine yeasts. Microbiol. Lett. 1994, 118, 213-218.
17. Singleton, V. L.; Kramling, T. E. Browning of white wines and an accelerated test for browning capacity. Am. J. Enol. Vitic. 1976, 27, 157-160.
18. Baraud, J. Etude des dérivés naturels de l'acide tartrique. Ann. Chim. 1954, 9, 535-604.
19. Clark, C. A.; Scollary, G. R. Influence of light exposure, ethanol and copper(II) on the formation of a precursor for xanthylium cations from tartaric acid. Aust. J. Grape Wine Res. 2003, 9, 64-71.
20. Clark, C. A.; Prenzler, D. P.; Scollary, G. R. The role of copper-(II) in the bridging reactions of (+)-catechin and glyoxylic acid in a model white wine. J. Agric. Food Chem. 2003, 51, 6204-6210.
21. Es-Safi, N.; Le Guenervé, C.; Cheynier, V.; Moutounet, M. 2D NMR analysis for unambiguous structural elucidation of phenolic compounds formed through reaction between (+)-catechin and glyoxylic acid. Magn. Reson. Chem. 2002, 40, 693-704.
22. Glories, Y. Evolution des composés phénoliques au cours du vieillissement du vin. Ann. Nutr. Aliment. 1978, 32, 1163-1169.
23. Jurd, L.; Somers, T. C. The formation of xanthylium salts from proanthocyanidins. Phytochemistry 1970, 9, 419-427.
24. MacGraw, W. G. Reactions at the A-ring of proanthocyanidins. In Chemistry and Significance of Condensed Tannins; Hemingway, R. W., Karchesy, J. J., Eds.; Plenum Press: New York, 1989; pp 227-248.
25. Sham, Y. Y.; Joans, J. A. Temperature dependent near UV molar absorptivities of several small aldehydes in aqueous solution. Spectrochim. Acta 1995, 51A, 247-251.