Formation of hydroxyphenyl-pyranoanthocyanins in Grenache wines: Precursor levels and evolution during aging

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 12, 2007, Pages 4883-4888

  Rentzsch, Michael ^a   Schwarz, Michael ^b   Winterhalter, Peter ^a   Hermosín Gutiérrez, Isidro ^c  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b PhytoLab GmbH   (Germany)

^c UNIVERSITY OF CASTILLA LA MANCHA   (Spain)

Author keywords

Aging; Caffeic acid; Grenache, red wine color; Hydroxycinnamic acids; Pinotin A; Pyranoanthocyanin; Vitisin A

Indexed keywords

ANTHOCYANIN; PHENOL DERIVATIVE;

ARTICLE; COLOR; FOOD HANDLING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPAIN; SYNTHESIS; WINE;

ANTHOCYANINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLOR; FOOD HANDLING; PHENOLS; SPAIN; WINE;

EID: 34250719904     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0702491     Document Type: Article

References (31)

1. Boulton, R.; Singleton, V. L.; Bisson, L. F.; Kunkee, R. E. V. Viticulture for winemakers. In Principles and Practice of Winemaking, 1st ed.; Springer, Chapman and Hall: New York, 1996; p 19.
2. Jackson, R. S. Introduction. In Wine Science. Principles, Practice, Perception, 2nd ed.; Taylor, S. L., Ed.; Academic Press: San Diego, CA, 2000; p 7.
3. Morel-Salmi, C.; Souquet, J. M.; Bes, M.; Cheynier, V. Effect of flash release treatment on phenolic extraction and wine composition. J. Agric. Food Chem. 2006, 54, 4270-4276.
4. Cheynier, V.; Teissedre, P. L. 8. Tablas de Composición. 6. Polifenoles. In Enología: Fundamentos Científicos y Tecnológicos; Flanzy, C., Ed.; Mundi-Prensa: Madrid, Spain, 2000; p224.
5. Cilliers, J. J. L.; Singleton, V. L. Nonenzymic autoxidative reactions of caffeic acid in wine. Am. J. Enol. Vitic. 1990, 41 (1), 84-86.
6. Moutounet, M.; Escudier, J. L. Prétraitement des raisins par Flash-détente sous vide. Incidence sur la qualité des vins. Bull. O. I. V. 2000, 73, 5-19.
7. Marenghi, M. Ganimede: new fermentation technology. Vignevini 2002, 29 (11), 104-106.
8. Snedden, J. The next step forward in red wine static fermentation technology. Aust. Grapegrower Winemaker 2000, 442, 28.
9. 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.
10. 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 1996, 735-739.
11. Lu, Y.; Foo, Y.; Sun, Y. New pyranoanthocyanins from blackcurrant seeds. Tetrahedron Lett. 2002, 43, 7341-7344.
12. Schwarz, M.; Wabnitz, T. C.; Winterhalter, P. Pathway leading to the formation of anthocyanin-vinylphenol adducts and related pigments in red wines. J. Agric. Food Chem. 2003, 51, 3682-3687.
13. Chatonnet, P.; Dubourdieu, D.; Boidron, J.-N.; Lavigne, V. Synthesis of volatile phenols by Saccharomyces cerevisiae in wines. J. Sci. Food Agric. 1993, 62, 191-202.
14. Glories, Y. Recherches sur la matière colorante des vins rouges. Bull. Chim. 1979, 9, 2649-2652.
15. Miniati, E.; Damiani, P.; Mazza, G. Copigmentation and self-association of anthocyanins in food model systems. Ital. J. Food Sci. 1992, 4, 109-116.
16. Mazza, G.; Fukumoto, L.; Delaquis, P.; Girard, B.; Ewert, B. Anthocyanins, phenolics, and color of Cabernet Franc, Merlot, and Pinot Noir wines from British Columbia. J. Agric. Food Chem. 1999, 47, 4009-4017.
17. Ribereau-Gayon, P.; Stonestreet, E. Dosage des tanins du vin rouge et determination de leur structure. Chim. Anal. 1966, 48 (4), 188-192.
18. ème partie. Mesure, origin et interpretation. Connaiss. Vigne Vin 1984, 18, 253-271.
19. Levengood, J.; Boulton, R. The variation in the color due to copigmentation in young Cabernet Sauvignon wines. In Red Wine Color. Revealing the Mysteries; ACS Symposium Series 886; Waterhouse, A. L., Kennedy, J. A., Eds.; American Chemical Society: Washington, DC, 2004; p 35.
20. Hermosín Gutiérrez, I. Influence of ethanol content on the extent of copigmentation in a Cencibel young red wine. J. Agric. Food Chem. 2003, 51, 4079-4083.
21. Ayala, F.; Echávarri, J. F.; Negueruela, A. I. A new simplified method for measuring the color of wines. III. All wines and brandies. Am. J. Enol. Vitic. 1999, 50, 359-363.
22. Pérez-Caballero, V.; Ayala, F.; Echávarri, J. F.; Negueruela, A. I. Proposal for a new standard OIV method for determination of chromatic characteristics of wine. Am. J. Enol. Vitic. 2003, 54, 59-62.
23. Schwarz, M.; Hofmann, G.; Winterhalter, P. Investigations on anthocyanins in wines from Vitis vinifera cv. Pinotage: factors influencing the formation of pinotin A and its correlation with wine age. J. Agric. Food Chem. 2004, 52, 498-504.
24. Schwarz, M.; Picazo-Bacete, J. J.; Winterhalter, P.; Hermosín- Gutiérrez, I. Effect of copigments and grape cultivar on the color of red wines fermented after the addition of copigments. J. Agric. Food Chem. 2005, 53, 8372-8381.
25. Hermosín Gutiérrez, I.; García-Romero, E. Antocianos de variedades tintas cultivadas en La Mancha: Perfiles varietales característicos de la uva y de los vinos monovarietales, y evolución durante la maduración de la baya. Alimentaria 2004, 41, 127-139.
26. Schwarz, M.; Jerz, G.; Winterhalter, P. Isolation and structure of Pinotin A, a new anthocyanin derivative from Pinotage wine. Vitis 2003, 42, 105-106.
27. Schwarz, M.; Winterhalter, P. A novel synthetic route to substituted pyranoanthocyanins with unique colour properties. Tetrahedron Lett. 2003, 44, 7583-7587.
28. Bakker, J.; Bridle, P.; Honda, T.; Kuwano, H.; Saito, N.; Terahara, N.; Timberlake, C. F. Identification of an anthocyanin occurring in some red wines. Phytochemistry 1997, 44, 1375-1382.
29. Fulcrand, H.; Benabdeljalil, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 1998, 47, 1401-1407.
30. Vivar-Quintana, A. M.; Santos-Buelga, C.; Francia-Aricha, E.; Rivas-Gonzalo, J. C. Formation of anthocyanin-derived pigments in experimental red wines. Food Sci. Technol. Int. 1999, 5, 347-352.
31. Schwarz, M.; Quast, P.; von Baer, D.; Winterhalter, P. Vitisin A content in Chilean wines from Vitis vinifera cv. Cabernet Sauvignon and contribution to the color of aged red wines. J. Agric. Food Chem. 2003, 51, 6261-6267.