New Anthocyanin Pigments Formed after Condensation with Flavanols

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 6, 1997, Pages 2262-2266

  Francia Aricha, E M ^a   Guerra, M T ^a   Rivas Gonzalo, J C ^a   Santos Buelga, C ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Acetaldehyde; Anthocyanin derived pigments; Flavan 3 ols; LC MS; Malvidin 3 monoglucoside; Procyanidins

Indexed keywords

EID: 0001241455     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9609587     Document Type: Article

References (26)

1. Bakker, J.; Picinelli, A.; Bridle, P. Model wine solutions: Colour and composition changes during ageing. Vitis 1993, 32, 111-118.
2. Baranowski, E. S.; Nagel, C. W. Kinetics of malvidin-3-glucoside condensation in wine model systems. J. Food Sci. 1983, 48, 419-421.
3. Brouillard, R.; Wigand, M. C.; Cheminat, A. Loss of colour, a prerequisite to plant pigmentation by flavonoids. Phytochemistry 1990, 29, 3457-3460.
4. Cameira-dos-Santos, P. J.; Brillouet, J. M.; Cheynier, V.; Moutounet, M. Detection and partial characterisation of new anthocyanin-derived pigments in wine. J. Sci. Food Agric. 1996, 70, 204-208.
5. Dallas, C.; Ricardo-da-Silva, J. M.; Laureano, O. Products formed in model wine solutions involving anthocyanins, procyanidin B2, and acetaldehyde. J. Agric. Food Chem. 1996a, 44, 2402-2407.
6. Dallas, C.; Ricardo-da-Silva, J. M.; Laureano, O. Interactions of oligomeric procyanidins in model wine solutions containing malvidin-3-glucoside and acetaldehyde. J. Sci. Food Agric. 1996b, 70, 493-500.
7. Dangles, O.; Wigand, M. C.; Brouillard, R. Polyphenols in plant pigmentation: The copigmentation case. Bull. Liaison -Groupe Polyphénols 1992, 16, 209-216.
8. Escribano-Bailón, T.; Dangles, O.; Brouillard, R. Coupling reactions between flavylium ions and catechin. Phytochemistry 1996, 41, 1583-1592.
9. Escribano-Bailón, T.; Gutiérrez-Fernández, Y.; Rivas-Gonzalo, J. C.; Santos-Buelga, C. Characterization of procyanidins of Vitis vinifera variety Tinta del País grape seeds. J. Agric. Food Chem. 1992, 40, 1794-1799.
10. Es-Safi, N.; Fulcrand, H.; Cheynier, V.; Moutounet, M.; Hmamouchi, M.; Essassi, E. M. Kinetic studies of acetaldehyde-induced condensation of flavan-3-ols and malvidin-3-monoglucoside in model solution systems. In Polyphenols Communications; Vercauteren, J., Chèze, C., Dumon, M. C., Weber, J. F., Eds.; Groupe Polyphénols: Bordeaux, France, 1996; Vol. 2, pp 279-280.
11. Figueiredo, P.; Elhabiri, M.; Toki, K.; Saito, N.; Dangles, O.; Brouillard, R. New aspects of anthocyanin complexation. Intramolecular copigmentation as a means for colour loss? Phytochemistry 1996, 41, 301-308.
12. Fulcrand, H.; Cameira-dos-Santos, P. J.; Sarni-Manchado, P.; Cheynier, V.; Favre-Bonvin, J. Structure of new anthocyanin-derived wine pigments. J. Chem. Soc., Perkin Trans. 1, 1996a, 735-739.
13. Fulcrand, H.; Cameira-dos-Santos, P. J.; Sarni-Manchado, P.; Cheynier, V.; Moutounet, M. New anthocyanin-derived wine pigments. In Polyphenols Communications; Vercauteren, J., Chèze, C., Dumon, M. C., Weber, J. F., Eds.; Groupe Polyphénols: Bordeaux, France, 1996b; Vol. 2, pp 259-260.
14. García-Viguera, C.; Bridle, P.; Bakker, J. The effect of pH on the formation of coloured compounds in model solutions containing anthocyanins, catechin and acetaldehyde. Vitis 1994, 33, 37-40.
15. Guerra, M. T.; González-Huerta, D. C.; Santos-Buelga, C.; Rivas-Gonzalo, J. C. Influencia del sulfitado sobre la evolución de la materia colorante del vino. Jorn. Vitic. Enol. Proc., 17th, 1995, 779-788.
16. Jurd, L. Anthocyanins and related compounds. XI. Catechin flavylium salt condensation reactions. Tetrahedron 1967, 23, 1057-1064.
17. Jurd, L.; Somers, T. C. The formation of xanthylium salts from proanthocyanidins. Phytochemistry 1970, 9, 419-427.
18. Liao, H.; Cai, Y.; Haslam, E. Polyphenols interactions. Anthocyanins: Copigmentation and colour changes in red wines. J. Sci. Food Agric. 1992, 59, 299-305.
19. Mistry, T. V.; Cai, Y.; Lilley, T. H.; Haslam, E. Polyphenol interactions. Part 5. Anthocyanin copigmentation. J. Chem. Soc., Perkin Trans. 2 1991, 1287-1296.
20. Rivas-Gonzalo, J. C.; 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. 1995, 43, 1444-1449.
21. Roggero, J. P.; Archier, P.; Coens, S.; Rocheville-Divorne, C. Etude par HPLC de la réaction glucoside de malvidineacetaldéhyde-composé phénolique. Connaiss. Vigne Vin. 1987, 21, 163-168.
22. Santos-Buelga, C.; Bravo-Haro, S.; Rivas-Gonzalo, J. C. Interactions between catechin and malvidin 3-monoglucoside in model soluctions. Z. Lebensm. Unters. Forsch. 1995, 201, 269-274.
23. Santos-Buelga, C.; Francia-Aricha, E. M.; Rivas-Gonzalo, J. C. Role of flavan-3-ol structure on direct condensation with anthocyanins. In Polyphenols Communications; Vercauteren, J., Chèze, C., Dumon, M. C., Weber, J. F., Eds.; Groupe Polyphénols: Bordeaux, France, 1996; Vol. 1, pp 9-10.
24. Sarni-Manchado, P.; Fulcrand, H.; Souquet, J. M.; Cheynier, V.; Moutounet, M. Stability and color of unreported wine anthocyanin-derived pigments. J. Food Sci. 1996, 61, 938-941.
25. Saucier, C.; Bourgeois, G.; Vitry, C.; Roux, D.; Glories, Y. Caractérisation des produits de la polymérisation (+)-catechine-éthanal en milieu hydroalcoolique acide proche du vin. In Polyphenols Communications; Vercauteren, J., Chèze, C., Dumon, M. C., Weber, J. F., Eds.; Groupe Polyphénols: Bordeaux, France, 1996; Vol. 2, pp 261-262.
26. Timberlake, F. C.; Bridle, P. Interactions between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. Am. J. Enol. Vitic. 1976, 27, 97-105.