Effect of ellagitannins, ellagic acid and volatile compounds from oak wood on the (+)-catechin, procyanidin B1 and malvidin-3-glucoside content of model wines

Australian Journal of Grape and Wine Research

Volumn 14, Issue 3, 2008, Pages 260-270

  Jordao A M ^a,b   Ricardo Da Silva, J M ^b   Laureano, O ^b   Mullen, W ^c   Crozier, A ^c  

^a POLYTECHNIC INSTITUTE OF VISEU   (Portugal)

^b INSTITUTO SUPERIOR DE AGRONOMIA   (Portugal)

^c UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

(+) catechin; Ellagic acid; Ellagitannins; Malvidin 3 glucoside; Model wine; Oak wood; Procyanidin B1; Volatile compounds

Indexed keywords

EID: 54249085905     PISSN: 13227130     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1755-0238.2008.00029.x     Document Type: Article

References (49)

1. Arapitsas, P., Antonopoulos, A., Stefanou, E., Dourtoglou, V. Dourtoglou, G. (2004) Artificial aging of wines using oak wood chips. Food Chemistry 86, 563 570.
2. Asen, S., Stewart, R.N. Norris, K.H. (1972) Co-pigmentation of anthocyanins in plant tissue and its effect on colour. Phytochemistry 11, 1139 1144.
3. Bakker, J. Timberlake, C.F. (1997) Isolation and identification, and characterization of new color-stable anthocyanins occuring in some red wines. Journal of Agricultural and Food Chemistry 45, 35 43.
4. Boulton, R. (2001) The copigmentation of anthocyanins and its role in the color of red wine: A critical review. American Journal of Enology and Viticulture 52, 67 87.
5. Chatonnet, P., Cutzach, I., Pons, M. Dubourdieu, D. (1999) Monitoring toasting intensity of barrels by chromatographic analysis of volatile compounds from toasted oak wood. Journal of Agricultural and Food Chemistry 47, 4310 4318.
6. Dallas, C., Ricardo-da-Silva, J.M. Laureano, O. (1996a) Interactions of oligomeric procyanidins in model wine solutions containing malvidin-3-glucoside and acetaldehyde. Journal of Science and Food Agriculture 70, 493 500.
7. Dallas, C., Ricardo-da-Silva, J.M. Laureano, O. (1996b) Products formed in model wine solutions involving anthocyanins, procyanidin B2, and acetaldehyde. Journal of Agricultural and Food Chemistry 44, 2402 2407.
8. Dallas, C., Hipólito-Reis, P., Ricardo-da-Silva, J.M. Laureano, O. (2003) Influence of acetaldehyde, pH and temperature on transformation of procyanidins in model wine solutions. American Journal of Enology and Viticulture 54, 119 124.
9. De Coninck, G., Jordão, A.M., Ricardo-da-Silva, J.M. Laureano, O. (2006) Evolution of phenolic composition and sensory properties in red wine aged in contact with Portuguese and French oak wood chips. Journal International des Sciences de l'Vigne et du Vin 40, 25 34.
10. De Simon, B.F., Sanz, M., Cadahia, E., Poveda, P. Broto, M. (2006) Chemical characterization of oak heart wood from Spanish forest of Quercus pyrenaica (Willd.). Ellagitannins, low molecular weight phenolic and volatile compounds. Journal of Agricultural and Food Chemistry 54, 8314 8321.
11. Dueñas, M., Fulcrand, H. Cheynier, V. (2006) Formation of anthocyanin-flavanol adducts in model solutions. Analytica Chimica Acta 563, 15 25.
12. Dufour, C. Bayonove, C.L. (1999) Interactions between wine polyphenols and aroma substances. An insight at the molecular level. Journal of Agricultural and Food Chemistry 47, 678 684.
13. Escalona, H., Birkmyre, L., Piggott, J.R. Paterson, A. (2002) Effect of maturation in small oak casks on the volatility of red aroma compounds. Analytica Chimica Acta 458, 45 54.
14. Es-Safi, N. Cheynier, V. (2004) Flavanols and anthocyanins as potent compounds in the formation of new pigments during storage and ageing of red wine. In : Red wine color: Revealing the mysteries. Eds. A.L. Waterhouse J.A. Kennedy (American Chemical Society : Washington, DC) pp. 143 159.
15. Freitas, V., Sousa, C., González-Paramás, A.M., Santos-Buelga, C. Mateus, N. (2004a) New pigments resulting from the reaction between malvidin-3-o-glucoside and catechin mediated by aldehydes from toasted oak. Proceedings of XXII International Conference on Polyphenols, Helsinki, Finland, Antti Hoikkala and Otto Soidinsalo edition (University of Helsinki : Helsinki) pp. 587 588.
16. Freitas, V., Sousa, C., González-Paramás, A.M., Santos-Buelga, C. Mateus, N. (2004b) Synthesis of a new catechin-pyrylium derived pigment. Tetrahedron Letters 45, 9349 9352.
17. Fulcrand, H., Benabdeljalil, C., Rigaud, J., Cheynier, V. Moutounet, M. (1998) A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 47, 1401 1407.
18. Guerra, C., Glories, Y. Vivas, N. (1996) Influence of ellagitannins on flavanols-anthocyans-acetaldehyde condensation réactions. Journal des Sciences et Technique de la Tonnellerie 2, 97 103.
19. Jordão, A.M., Ricardo-da-Silva, J.M. Laureano, O. (2005) Extraction and evolution of some ellagic tannins and ellagic acid of oak wood chips (Quercus pyrenaica) in model wine solutions: Effect of time, pH, temperature and alcoholic content. South African Journal of Enology and Viticulture 26, 83 89.
20. Jordão, A.M., Ricardo-da-Silva, J.M. Laureano, O. (2006) Role of oak wood extract, ellagic acid and oxygen on malvidin-3-glucoside, (+)-catechin and colour parameters evolution in model wine solutions. American Journal of Enology and Viticulture 57, 377 381.
21. Jordão, A.M., Ricardo-da-Silva, J.M. Laureano, O. (2007) Ellagitannins from Portuguese oak wood (Quercus pyrenaica Willd.) used in cooperage: Influence of geographical origin, coarseness of the grain and totasting level. Holzforschung 61, 155 160.
22. Lefeuvre, D., Jourdes, M., Quideau, S., Saucier, C. Glories, Y. (2004) Hemissyntheses of anthocyano-ellagitannins. Proceedings of XXII International Conference on Polyphenols, Helsinki, Finland, Antti Hoikkala and Otto Soidinsalo edition (University of Helsinki : Helsinki) pp. 657 658.
23. Lopes, P., Richard, T., Saucier, C., Teissedre, P.L., Monti, J.P. Glories, Y. (2007) Anthocyanone A: A quinone methide derivative resulting from malvidin-3-O-glucoside degradation. Journal of Agricultural and Food Chemistry 55, 2698 2704.
24. Masson, G., Moutounet, M. Puech, J.L. (1995) Ellagitannin content of oak wood as a function of species and of sampling position in the tree. American Journal of Enology and Viticulture 46, 262 268.
25. Mateus, N., Silva, A.M.S., Vercauteren, J. Freitas, V. (2001) Occurrence of anthocyanin-derived pigments in red wines. Journal of Agricultural and Food Chemistry 49, 4836 4840.
26. Mateus, N., Pascual-Teresa, S., Rivas-Gonzalo, J.C., Santos-Buelga, C. Freitas, V. (2002a) Structural diversity of anthocyanin-derived pigments in port wines. Food Chemistry 76, 335 342.
27. Mateus, N., Silva, A.M.S., Santos-Buelga, C., Rivas-Gonzalo, J.C. Freitas, V. (2002b) Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry. Journal of Agricultural and Food Chemistry 50, 2110 2116.
28. Mateus, N., Carvalho, E., Carvalho, A.R.F., Melo, A., González-Paramás, A.M., Santos-Buelga, C., Silva, A.M.S. Freitas, V. (2003) A new class of blue anthocyanin-derived pigments isolated from red wines. Journal of Agricultural and Food Chemistry 51, 1919 1923.
29. Moutounet, M., Rabier, P.H., Puech, J.L., Verette, E. Barillere, J.M. (1989) Analysis by HPLC of extractable substances in oak wood. Application to a Chardonnay wine. Sciences des Aliments 9, 35 51.
30. Nonier, M.F., Pianet, I., Laguerre, M., Vivas, N. De Gaulejac, N.V. (2006) Condensation products derived from flavan-3-ol oak wood aldehydes reaction-1. Structural investigation. Analytica Chimica Acta 563, 76 83.
31. Obradovic, D. (2006) Grape-derived tannins and their application. Australian and New Zealand Grapegrower and Winemaker 509a, 66 73.
32. Pissarra, J., Lourenço, S., González-Paramás, A.M., Mateus, N., Santos-Buelga, C., Silva, A.M.S. Freitas, V. (2005) Isolation and structural characterization of new anthocyanin-alkyl-catechin pigments. Food Chemistry 90, 81 87.
33. Pollnitz, A.P., Jones, G.P. Sefton, M.A. (1999) Determination of oak lactones in barrel-aged wines and in oak extracts by stable isotope dilution analysis. Journal of Chromatography A 857, 239 246.
34. Pontallier, P., Salagoity-Auguste, M.H. Ribéreau-Gayon, P. (1982) Intervention du bois de chêne dans l'évolution des vins rouges. Connaissance de la Vigne et du Vin 16, 45 61.
35. Prida, A. Puech, J.L. (2006) Influence of geographical origin and botanical species on the content of extractives in American, French, and East European oak woods. Journal of Agricultural and Food Chemistry 54, 8115 8126.
36. Quideau, S., Jourdes, M., Saucier, C., Glories, Y., Pardon, P. Baudry, C. (2003) DNA topoisomerase inhibitor acutissimin A and other flavano- ellagitannins in red wine. Angewandte Chemie International Edition 42, 6012 6014.
37. Quideau, S., Jourdes, M., Lefeuvre, D., Montaudon, D., Saucier, C., Glories, Y., Pardon, P. Pourquier, P. (2005) The chemistry of wine polyphenolic C-glycosidic ellagitannins trargeting human topoisomerase II. Chemistry a European Journal 11, 6503 6513.
38. Quinn, M.K. Singleton, V.L. (1985) Isolation and identification of ellagitannins from white oak and an estimation of their roles in wine. American Journal of Enology and Viticulture 36, 429 434.
39. Remy, S., Fulcrand, H., Labarbe, B., Cheynier, V. Moutounet, M. (2000) First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions. Journal of the Science of Food and Agriculture 80, 745 751.
40. Ribéreau-Gayon, P., Glories, Y., Maujean, A. Dubourdieu, D. (2006) Aging red wines in vat and barrel: Phenomena occurring during aging. In : Handbook of enology: The chemistry of wine stabilization and treatments, Vol. II. Eds. John Wiley & Sons, Ltd (John Wiley & Sons Ltd : Chichester, UK) pp. 387 428.
41. Roure, F. Anderson, G. (2006) Characteristics of oenotannins. Australian and New Zealand Grapegrower and Winemaker 510, 49 50.
42. Salas, E., Atanasova, V., Poncet-Legrand, C., Meudec, E., Mazauric, J.P. Cheynier, V. (2004) Demonstration of the occurrence of flavanol-anthocyanin adducts in wine and in model solutions. Analytica Chimica Acta 513, 325 332.
43. Saucier, C., Jourdes, M., Glories, Y. Quideau, S. (2006) Extraction, detection, and quantification of flavano-ellagitannins and ethylvescalagin in a Bourdeaux red wine aged in oak barrels. Journal of Agricultural and Food Chemistry 54, 7349 7354.
44. Sousa, C., Mateus, N., Perez-Alonso, J., Santos-Buelga, C. De Freitas, V. (2005) Preliminary study of oaklins, a new class of brick-red catechinpyrylium pigments from the reaction between catechin and wood aldehydes. Journal of Agricultural and Food Chemistry 53, 9249 9256.
45. Sousa, C., Mateus, N., Silva, A.M.S., González-Paramás, A.M., Santos-Buelga, C. De Freitas, V. (2007) Structural and chromatic characterization of a new malvidin 3-glucoside-vanillyl-catechin pigment. Food Chemistry 102, 1344 1351.
46. Viriot, C., Scalbert, A., Lapierre, C.L. Moutounet, M. (1993) Ellagitannins and lignins in aging of spirits in oak barrels. Journal of Agricultural and Food Chemistry 41, 1872 1879.
47. Viriot, C., Scalbert, A., Hervé Du Penhoat, C.L. Moutounet, M. (1994) Ellagitannins in woods of sessile oak and sweet chestnut dimerization and hydrolysis during wood ageing. Phytochemistry 36, 1253 1260.
48. Vivas, N. Glories, Y. (1993) Les phénomènes dóxydoreduction liés à l'élevage en barrique des vins rouges: Aspects technologiques. Revue Française d'Oenologie 33, 33 38.
49. Vivas, N. Glories, Y. (1996) Role of oak wood ellagitannins in the oxidation process of red wine during aging. American Journal of Enology and Viticulture 7, 103 107.