Accumulation and extractability of grape skin tannins and anthocyanins at different advanced physiological stages

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 19, 2006, Pages 7331-7338

  Fournand, David ^a   Vicens, Anysia ^a   Sidhoum, Louise ^a   Souquet, Jean Marc ^a   Moutounet, Michel ^a   Cheynier, Veronique ^a  

^a SPO   (France)

Author keywords

Anthocyanins; Biosynthesis; Extractability; Extraction yield; Grape skin; HPLC; Proanthocyanidins; Pulp sugar content; Ripening; Tannins

Indexed keywords

ANTHOCYANIN; CARBOHYDRATE; PROANTHOCYANIDIN; TANNIN DERIVATIVE;

ARTICLE; CHEMISTRY; FRUIT; GRAPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; KINETICS; PHYSIOLOGY;

ANTHOCYANINS; CARBOHYDRATES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FRUIT; KINETICS; PROANTHOCYANIDINS; TANNINS; VITIS;

VITIS SP.;

EID: 33749673122     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061467h     Document Type: Article

References (56)

1. Souquet, J.-M.; Cheynier, V.; Brossaud, F.; Moutounet, M. Polymeric proanthocyanidins from grape skins. Phytochemistry 1996, 43, 509-512.
2. Downey, M. O.; Harvey, J. S.; Robinson, S. P. Analysis of tannins in seeds and skins of Shiraz grapes throughout berry development. Aust. J. Grape Wine Res. 2003, 9, 15-27.
3. Kennedy, J. A.; Hayasaka, Y.; Vidal, S.; Waters, E. J.; Jones, G. P. Composition of grape skin proanthocyanidins at different stages of berry development. J. Agric. Food Chem. 2001, 49, 5348-5355.
4. Kennedy, J. A.; Matthews, M. A.; Waterhouse, A. L. Effect of maturity and vine water status on grape skin and wine flavonoids. Am. J. Enol. Vitic. 2002, 53, 268-274.
5. Jeong, S. T.; Goto-Yamamoto, N.; Hashizume, K.; Esaka, M. Expression of the flavonoid 3′-hydroxylase and flavonoid 3′,5′-hydroxylase genes and flavonoid composition in grape (Vitis vinifera). Plant Sci. 2006, 170, 61-69.
6. Gonzales-San José, M. L.; Barron, L. J. R.; Diez, C. Evolution of anthocyanins during maturation of tempranillo grape variety (Vitis vinifera) using polynomial regression models. J. Sci. Food Agric. 1990, 51, 337-343.
7. Garcia-Beneytez, E.; Cabello, F.; Revilla, E. Analysis of grape and wine anthocyanins by HPLC-MS. J. Agric. Food Chem. 2003, 51, 5622-5629.
8. Nunez, V.; Monagas, M.; Gomez-Cordoves, M. C.; Bartolomé, B. Vitis vinifera L. cv. Graciano grapes characterized by its anthocyanin profile. Postharvest Biol. Technol. 2004, 31, 69-79.
9. Gonzalez-Neves, G.; Barreiro, L.; Gil, G.; Franco, J.; Ferrer, M.; Moutounet, M.; Carbonneau, A. Anthocyanic composition of Tannat grapes from the south region of Uruguay. Anal. Chim. Acta 2004, 513, 197-202.
10. Roggero, J. P.; Coen, S.; Ragonnet, B. High performance liquid chromatography survey on changes in pigment content in ripening grapes of Syrah. An approach to anthocyanin metabolism. Am. J. Enol. Vitic. 1986, 37, 77-83.
11. Yokotsuka, K.; Nagao, A.; Nakazawa, K.; Sato, M. Changes in anthocyanins in berry skins of Merlot and Cabernet Sauvignon grapes grown in two soils modified with limestone or oyster shell versus a native soil over two years. Am. J. Enol. Vitic. 1999, 50, 1-12.
12. Roggero, J. P.; Larice, J. L.; Rocheville Divorne, C.; Archier, P.; Coen, S. Composition anthocyanique des cépages. I : Essai de classification par analyse en composantes principales et par analyse factorielle discriminante. Rev. Fr. Oenol. 1988, 112, 41-48.
13. Larice, J.-L.; Archier, P.; Rocheville-Divorne, C.; Coen, S.; Roggero, J.-P. Composition anthocyanique des cépages. II- Essai de classification sur trois ans par analyse en composantes principales et étude des variations annuelles de cépages de même provenance. Rev. Fr. Oenol. 1989, 121, 7-12.
14. de Villiers, A.; Vanhoenacker, G.; Majek, P.; Sandra, P. Determination of anthocyanins in wine by direct injection liquid chromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis. J. Chromatogr., A 2004, 1054, 195-204.
15. Vidal, S.; Cartalade, D.; Souquet, J.-M.; Fulcrand, H.; Cheynier, V. Changes in proanthocyanidin chain length in winelike model solutions. J. Agric. Food Chem. 2002, 50, 2261-2266.
16. Escribano-Bailon, T.; Alvarez-Garcia, M.; Rivas-Gonzalo, J. C.; Heredia, F. J.; Santos-Buelga, C. Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin. J. Agric. Food Chem. 2001, 49, 1213-1217.
17. Malien-Aubert, C.; Dangles, O.; Amiot, M.-J. Influence of procyanidins in the color stability of oenin solutions. J. Agric. Food Chem. 2002, 50, 3299-3305.
18. Malien-Aubert, C.; Dangles, O.; Amiot, M.-J. Color stability of commercial anthocyanin-based extracts in relation to the phenolic composition. Protective effects by intra- and intermolecular copigmentation. J. Agric. Food Chem. 2001, 49, 170-176.
19. Wang, H.; Race, E. J.; Shrikhande, A. J. Anthocyanin transformation in Cabernet Sauvignon wine during aging. J. Agric. Food Chem. 2003, 51, 7989-7994.
20. Berké, B.; de Freitas, V. A. P. Influence of procyanidin structures on their ability to complex with oenin. Food Chem. 2005, 90, 453-460.
21. Esteban, M. A.; Villanueva, M. J.; Lissarrague, J. R. Effect of irrigation on changes in the anthocyanin composition of the skin of cv Tempranillo (Vitis vinifera L) grape berries during ripening. J. Sci. Food Agric. 2001, 81, 409-420.
22. Downey, M. O.; Harvey, J. S.; Robinson, S. P. The effect of bunch shading on berry development and flavonoid accumulation in Shiraz grapes. Aus. J. Grape Wine Res. 2004, 10, 55-73.
23. Ryan, J.-M.; Revilla, E. Anthocyanin composition of Cabernet Sauvignon and Tempranillo grapes at different stages of ripening. J. Agric. Food Chem. 2003, 51, 3372-3378.
24. Cadot, Y.; Minana Castello, M. T.; Chevalier, M. Flavan-3-ol compositional changes in grape berries (Vitis vinifera L. cv Cabernet Franc) before veraison, using two complementary analytical approaches, HPLC reversed phase and histochemistry. Anal. Chim. Acta 2006, 563, 65-75.
25. Ribéreau-Gayon, P.; Glories, Y. Structure of condensed phenolic compounds in vinifera grapes and wine. Influence of ripening and infection by Botrytis cinerea on phenolic content. C. R. Colloq. 1980, 228-234.
26. Harbertson, J. F.; Kennedy, J. A.; Adams, D. O. Tannin in skins and seeds of Cabernet Sauvignon, Syrah, and Pinot noir berries during ripening. Am. J. Enol. Vitic. 2002, 53, 54-59.
27. de Freitas, V. A. P.; Glories, Y.; Monique, A. Developmental changes of proanthocyanidins in grapes of red Vitis vinifera varieties and their composition in respective wines. Am. J. Enol. Vitic. 2000, 51, 397-403.
28. Munoz, O.; Sepulveda, M.; Schwartz, M. Effects of enzymatic treatment on anthocyanic pigments from grape skins from chilean wine. Food Chem. 2004, 87, 487-490.
29. Fernandez-Zurbano, P.; Ferreira, V.; Pena, C.; Escudero, A.; Cacho, J. Effects of maceration time and pectolytic enzymes added during maceration on the phenolic composition of must. Food Sci. Tecknol. Int. 1999, 5, 319-325.
30. Gonzales-Manzano, S.; Rivas-Gonzalo, J. C.; Santos-Buelga, C. Extraction of flavan-3-ols from grape seed and skin into wine using simulated maceration. Anal. Chim. Acta 2004, 513, 283-289.
31. Gomez-Miguez, M.; Heredia, F. J. Effect of the maceration technique on the relationships between anthocyanin composition and objective color of Syrah wines. J. Agric. Food Chem. 2004, 52, 5117-5123.
32. Canals, R.; Llaudy, M. C.; Valls, J.; Canals, J. M.; Zamora, F. Influence of ethanol concentration on the extraction of color and phenolic compounds from the skin and seeds of Tempranillo grapes at different stages of ripening. J. Agric. Food Chem. 2005, 53, 4019-4025.
33. Pérez-Magarino, S.; Gonzalez-San José, M. L. Evolution of flavanols, anthocyanins, and their derivatives during the aging of red wines elaborated from grapes harvested at different stages of ripening. J. Agric. Food Chem. 2004, 52, 1181-1189.
34. Kennedy, J. A.; Jones, G. P. Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J. Agric. Food Chem. 2001, 49, 1740-1746.
35. Souquet, J.-M.; Mazauric, J.-P.; Meudec, E.; Preys, S.; Morel-Salmi, C.; Cheynier, V. Comparison on different methods of depolymerization to the characterization and quantification of proanthocyanidins in grape seed, grape skin and wine. Proceedings of XXII International Conference on Polyphenols, Polyphenols Communications 2004, A. Hoikkala, O. Soidinsalo, K. Wähälä, Eds. Helsinki, Finland, 2004; pp 693-694.
36. Singleton, V. L.; Rossi, J. A. Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents. Am. J. Enol. Vitic. 1965, 16, 144-158.
37. Delcour, J. A.; Janssens. de Varebeke, D. A new colourimetric assay for flavonoids in pilsner beers. J. Inst. Brew. 1985, 91, 37-40.
38. Wulf, L.; Nagel, C. High-pressure liquid chromatographic separation of anthocyanins of Vitis vinifera. Am. J. Enol. Vitic. 1978, 29, 42-49.
39. Carando, S.; Teissedre, P. L.; Cabanis, J. C. HPLC coupled with fluorescence detection for the determination of procyanidins in white wines. Chromatographia 1999, 50, 253-254.
40. Cortell, J.; Halbleib, M.; Gallagher, A. V.; Righetti, T. L.; Kennedy, J. A. Influence of vine vigor on grape (Vitis vinifera L. cv; Pinot Noir) and wine proanthocyanidins. J. Agric. Food Chem. 2005, 53, 5798-5808.
41. Vidal, S.; Meudec, E.; Cheynier, V.; Skouroumounis, G.; Hayasaka, Y. Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. J. Agric. Food Chem. 2004, 52, 7144-7151.
42. Boss, P. K.; Davies, C.; Robinson, S. P. Analysis of the expression of anthocyanin pathway genes in developing Vitis vinifera L. cv Shiraz grape berries and the implications for pathways regulation. Plant Physiol. 1996, 111, 1059-1066.
43. Spayd, S. E.; Tarara, J. M.; Mee, D. L.; Ferguson, J. C. Separation of sunlight and temperature effects on the composition of Vitis vinifera cv. Merlot berries. Am. J. Enol. Vitic. 2002, 53, 171-182.
44. 2 on the formation of pyranoanthocyanins during red wine fermentation with two species of Saccharomyces. Int. J. Food Microbiol. 2006, 106, 123-129.
45. Bogs, J.; Downey, M. O.; Harvey, J. S.; Ashton, A. R.; Tanner, G. J.; Robinson, S. P. Proanthocyanidin synthesis and expression of genes encoding leucoanthocyanidin reductase and anthocyanidin reductase in developing grape berries and grapevine leaves. Plant Physiol. 2005, 139, 652-663.
46. Ojeda, H.; Andary, C.; Kraeva, E.; Carbonneau, A.; Deloire, A. Influence of pre- and postvéraison water deficit on synthesis and concentration of skin phenolic compounds during berry growth of Vitis vinifera cv. Shiraz. Am. J. Enol. Vitic. 2002, 53, 261-267.
47. Boulton, R. B. Methods for the assessment of copigmentation in red wines. Presented at the 47th Annual Meeting of the American Society for Enology and Viticulture, Reno, NV, 1996.
48. Gomez-Cordovés, C.; Monagas, M.; Nunez, V.; Bartolomé, B. Importancia del perfil antocianico en diferentes variedades de Vitis vinifera L. Presented at the 7th Viticulture and Enology Latin-American Congress, Montevideo, Uruguay, 2001.
49. Vidal, S.; Leigh, F.; Guyot, S.; Marnet, N.; Kwiatkowski, M.; Gawel, R.; Cheynier, V.; Waters, E. J. The mouth-feel properties of grape and apple proanthocyanidins in a wine-like medium. J. Sci. Food Agric. 2003, 83, 564-573.
50. Amrani-Joutei, K.; Glories, Y.; Mercier, M. Localisation des tanins dans la pellicule de baie de raisin. Vitis 1994, 33, 133-138.
51. Le Bourvellec, C.; Guyot, S.; Renard, C. Non-covalent interaction between procyanidins and apple cell wall material. Part I. Effect of some environmental parameters. Biochim. Biophys. Acta 2004, 1672, 192-202.
52. Le Bourvellec, C.; Renard, C. Non-covalent interaction between procyanidins and apple cell wall material. Part II: Quantification and impact of cell wall drying. Biochim. Biophys. Acta 2005, 1725, 1-9.
53. Le Bourvellec, C.; Bouchet, B.; Renard, C. Non-covalent interaction between procyanidins and apple cell wall material. Part III: Study on model polysaccharides. Biochim. Biophys. Acta 2005, 1725, 10-18.
54. Riou, V.; Vernhet, A.; Doco, T.; Moutounet, M. Aggregation of grape seed tannins in model wine - effect of wine polysaccharides. Food Hydrocolloids 2002, 16, 17-23.
55. Taira, S.; Ono, M.; Matsumoto, N. Reduction of persimmon astringency by complex formation between pectin and tannins. Postharvest Biol. Technol. 1997, 12, 265-271.
56. Vidal, S.; Courcoux, P.; Francis, L.; Kwiatkowski, M.; Gawel, R.; Williams, P.; Waters, E.; Cheynier, V. Use of an experimental design approach for evaluation of key wine components on mouth-feel perception. Food Qual. Prefer. 2004, 15, 209-217.