Ethylidene-bridged flavan-3-ols in red wine and correlation with wine age

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 15, 2007, Pages 6292-6299

  Drinkine, Jessica ^a   Lopes, Paulo ^a   Kennedy, James A ^b   Teissedre, Pierre Louis ^a   Saucier, Cedric ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

Aging; EDP; Flavan 3 ol, ethylidene bridge; Phloroglucinolysis; Red wine; Tannin

Indexed keywords

VITACEAE;

EID: 34547733599     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf070038w     Document Type: Article

References (43)

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. Phytochemistry 1994, 56, 781-784.
8. Haslam, E. In vino veritas: Oligomeric procyanidins and the ageing of red wines. Phytochemistry 1980, 19, 2577-2582.
9. Jurd, L. Review of polyphenols 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.; 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.
12. Romano, P.; Suzzi, G.; Turbanti, L.; Polsinelli, M. Acetaldehyde production in Saccharomyces cerevisiae wine yeasts. Microbiol. Lett. 1994, 118, 213-218.
13. Drinkine, J.; Saucier, C.; Glories, Y. (+)-Catechin-aldehyde condensations: Competition between acetaldehyde and glyoxylic acid. J. Agric. Food Chem. 2005, 53, 7552-7558.
14. 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.
15. Saucier, C.; Guerra, C.; Laguerre, M.; Glories, Y. (+)-catechin- acetaldehyde condensation products in relation with wine-ageing. Phytochemistry 1997, 46, 229-234.
16. Drinkine, J.; Lopes, P.; Kennedy, J. A.; Teissedre, P.-L.; Saucier, C. Analysis of ethylidene-bridged flavan-3-ols in wine. J. Agric. Food Chem. 2007, 55, 1109-1116.
17. Peyrot des Gachons, C.; Kennedy, J. A. Direct method for determining seed and skin proanthocyanidin extraction into red wine. J. Agric. Food Chem. 2003, 51, 5877-5881.
18. Glories, Y. La couleur des vins rouges. II. Mesure, origine et interprétation. Conn. Vigne Vin 1984, 18, 253-271.
19. Ribéreau-Gayon, P.; Glories, Y.; Maujean, A.; Dubourdieu, D. Les composés phénoliques. In Traité d'oenologie. Tome 2. Chimie du vin Stabilisation et Traitements; Dunod: Paris, France, 1998a; pp 163-237.
20. Ribéreau-Gayon, P.; Stonestreet, E. Dosage des tanins du vin rouge et détermination de leur structure. Chim. Anal. 1966, 48, 188-196.
21. Ribéreau-Gayon, P.; Stonestreet, E. Determination of anthocyanins in red wine. Bull. Soc. Chim. 1965, 9, 2649-2652.
22. Glories, Y. La matière colorante du vin rouge. Thèse d'Etat, Université de Bordeaux 2, Bordeaux, France, 1978.
23. Ribéreau-Gayon, J. Dissolution d'oxygène dans les vins. In Contribution à l'étude des Oxydations et Réductions dans les vins. Application à l'étude du Vieillissement et des Casses; Delmas: Bordeaux, France, 1933; pp 35.
24. Lopes, P.; Saucier, C.; Teissedre, P.-L.; Glories, Y. Impact of storage position on oxygen ingress through different closures into wine bottles. J. Agric. Food Chem. 2006, 54, 6471-6746.
25. Picinelli, A.; Bakker, J. P. B. Model wine solutions: Effect of sulphur dioxide on colour and composition during ageing. Vitis 1994, 33, 31-35.
26. Flanzy, C. Tables de composition. In Oenologie: Fondements Scientifiques et Technologiques; Tec et Doc Lavoisier: Paris, 1998; pp 315-336.
27. Rivas-Gonzalo, J.; Bravo-Haro, S.; Santos-Buelga, C. Detection of compounds formed through the reaction of malvidin 3-monoglucoside and catechin in the presence of acetaldehyde. J. Agric. Food Chem. 1996, 43, 1444-1449.
28. Francia-Aricha, E. M.; Guerra, M. T.; Rivas-Gonzalo, J. C.; Santos-Buelga, C. New anthocyanin pigments formed after condensation with flavanols. J. Agric. Food Chem. 1997, 45, 2262-2266.
29. Escribano-Bailon, T.; Alvarez-Garcia, M.; Rivas-Gonzalo, J.; Heredia, F. J.; Santos-Buelga, C. Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-0-glucoside and (+)-catechin. J. Agric. Food Chem. 2001, 49, 1213-1217.
30. Timberlake, C. F.; Bridle, P. The effect of processing and other factors on the colour characteristics of some red wines. Vitis 1976, 15, 37-49.
31. Dallas, C.; Ricardo-Da-Silva, M. J.; Laureano, O. Products formed in model wine solutions involving anthocyanins, procyanidin B2, and acetaldehyde. J. Agric. Food Chem. 1996, 44, 2402-2407.
32. Bakker, J.; Picinelli, A.; Bridle, P. Model Wine solutions: Colour and composition changes during ageing. Vitis 1993, 32, 111-118.
33. Morata, A.; Calderon, F.; Gonzalez, M. C.; Gomez-Cordoves, M. C.; Suarez, J. A. Formation of the highly stable pyranoanthocyanins (vitisins A and B) in red wines by the addition of pyruvic acid and acetaldehyde. Food Chem. 2007, 100, 1144-1152.
34. Ribéreau-Gayon, P.; Pontallier, P.; Glories, Y. Some interpretations of colour changes in young red wines during their conservation. J. Sci. Food Agric. 1983, 34, 505-516.
35. Es-Safi, N.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system. J. Agric. Food Chem. 1999, 47, 2096-2102.
36. Bakker, J.; Timberlake, C. F. Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines. J. Agric. Food Chem. 1997, 45, 35-43.
37. Vivar-Quintana, A. M.; Santos-Buelga, C.; Rivas-Gonzalo, J. C. Anthocyanin-derived pigments and colour of red wines. Anal. Chim. Acta 2002, 458, 147-155.
38. Mateus, N.; Carvalho, E.; Carvalho, R. F. A.; Melo, A.; Gonzales-Paramas, M. A.; Santos-Buelga, C.; De Freitas, A. P. V. Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol occuring in aging red wines. J. Agric. Food Chem. 2003, 51, 277-282.
39. Mateus, N.; Oliveira, J.; Santos-Buelga, C.; Silva, A. M. S.; De Freitas, A. P. V. NMR structure characterization of a new vinylpyranoanthocyanin- catechin pigment (a portisin). Tetrahedron Lett. 2004, 45, 3455-3457.
40. He, J.; Santos Buelga, C.; Mateus, N.; De Freitas, A. P. V. Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques. J. Chromatogr. A 2006, 1134, 215-225.
41. Somers, T. C. The polymeric nature of wine pigments. Phytochemistry 1971, 10, 2175-2186.
42. Cheynier, V.; Fulcrand, H.; Brossaud, F.; Asselin, C.; Moutounet, M. 10. Phenolic composition as related to red wine flavor. In Chemistry of Wine Flavor, Waterhouse, A. L., Ebeler, S. E., Eds.; American Chemical Society: Washington, DC, 1999; p 256.
43. 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. 1997b, 45, 1045-1049.