Grape and wine phenolics: Observations and recent findings

Ciencia e Investigacion Agraria

Volumn 35, Issue 2, 2008, Pages 77-90

  Kennedy, James A ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

Anthocyanins; Proanthocyanidins; Red wine; Tannins; Vitis vinifera

Indexed keywords

VITACEAE; VITIS VINIFERA;

EID: 65249122372     PISSN: 03045609     EISSN: 07181620     Source Type: Journal    
DOI: 10.4067/S0718-16202008000200001     Document Type: Review

References (106)

1. Arnold, R.A., A.C. Noble, and V.L. Singleton. 1980.Bitterness and astringency of phenolic fractions in wine. J. Agric. Food Chem. 28:675-678.
2. Aron, P.M., and J.A. Kennedy. 2007. Compositional investigation of phenolic polymers isolated from Vitis vinifera L. cv. Pinot noir during fermentation. J. Agric. Food Chem. 55:5670-5680.
3. Aubert, S., and C. Poux. 1969. Extraction des composés phénoliques du raison II. Taux de passage dans les vins. Ann. Technol. Agric. 18:111-127.
4. Bakker, J., and C.F. Timberlake. 1997. Isolation, identification, and characterization of new color stable anthocyanins occurring in some red wines. J. Agric. Food Chem. 45:35-43.
5. Benabdeljalil, C., V. Cheynier, H. Fulcrand, A. Hakiki, M. Mosaddak, and M. Moutounet. 2000. Evidence of new pigments resulting from reaction between anthocyanins and yeast metabolites. Sciences des Aliments 20:203-220.
6. Berg, H.W., and M. Akiyoshi. 1956. The effect of contact time of juice with pomace on the color and tannin content of red wines. Am. J. Enol. Vitic. 7:84-90.
7. Bergqvist, J., N. Dokoozlian, and N. Ebisuda. 2001. Sunlight exposure and temperature effects on berry growth and composition of Cabernet Sauvignon and Grenache in the central San Joaquin Valley of California. Am. J. Enol. Vitic. 52:1-7.
8. Bogs, J., M.O. Downey, J.S. Harvey, A.R. Ashton, G.J. Tanner, and S.P. Robinson. 2005. Proanthocyanidin synthesis and expression of genes encoding leucoanthocyanidin reductase and anthocyanidin reductase in developing grape berries and grapevine leaves. Plant Physiol. 139:652-663.
9. Bogs, J., F.W. Jaffé, A.M. Takos, A.R. Walker, and S.P. Robinson. 2007. The grapevine transcription factor VvMYBPA1 regulates proanthocyanidin synthesis during fruit development. Plant Physiol. 143:1347-1361.
10. Boss, P.K., C. Davies, and S.P. Robinson. 1996. Analysis of the expression of anthocyanin pathway genes in developing Vitis vinifera L. cv. Shiraz grape berries and the implications for pathway regulation. Plant Physiol. 111:1059- 1066.
11. Boselli, E., R.B. Boulton, J.H. Thorngate, and N.G. Frega. 2004. Chemical and sensory characterization of DOC red wines from Marxhe (Italy) related to vintage and grape cultivars. J. Agric. Food Chem. 52:3843-3854.
12. Cheynier, V., H. Fulcrand, F. Brossaud, C. Asselin, and M. Moutounet. 1998. Phenolic composition as related to red wine flavor. Pages 125-141. In: Chemistry of Wine Flavor. A.L. Waterhouse and S.E. Ebeler (eds.). Oxford University Publishing, NY. USA.
13. Cortell, J.M., M. Halbleib, A.V. Gallagher, T. Righetti, and J.A. Kennedy. 2005. Influence of vine vigor on grape (Vitis vinifera L. cv. Pinot noir) and wine proanthocyanidins. J. Agric. Food Chem. 53:5798-5808.
14. Cortell, J.M., and J.A. Kennedy. 2006. Effect of shading on accumulation of flavonoid compounds in Vitis vinifera L. Pinot noir fruit and extraction in a model system. J. Agric. Food Chem. 54:8510-8520.
15. Cortell, J.M., M. Halbleib, A.V. Gallagher, T. Righetti, and J.A. Kennedy. 2007a. Influence of vine vigor on grape (Vitis vinifera L. cv. Pinot noir) anthocyanins. 1. anthocyanin concentration and composition in fruit. J. Agric. Food Chem. 55:6575-6584.
16. Cortell, J.M., M. Halbleib, A.V. Gallagher, T. Righetti, and J.A. Kennedy. 2007b. Influence of vine vigor on grape (Vitis vinifera L. Cv. Pinot noir) anthocyanins. 2. anthocyanins and pigmented polymers in wine. J. Agric. Food Chem. 55:6585-6595.
17. Cozzolino, D., R.G. Dambergs, L. Janik, W.U. Cynkar, and M. Gishen. 2006. Analysis of grapes and wine by near infrared spectroscopy. J. Near Infrared Spectr. 14:279-289.
18. De Frietas, V.A.P., Y. Glories, and A. Monique. 2000. Developmental changes of procyanidins in grapes of red Vitis vinifera varieties and their composition in respective wines. Am. J. Enol. Vitic. 51:397-403.
19. De Freitas, V., E. Carvalho, and N. Mateus. 2003. Study of carbohydrate influence on proteintannin aggregation by nephelometry. Food Chemistry 81:503-509.
20. Del Carmen-Llaudy, M.R., S. Canals, J.M. González-Manzano, C. Canals, C. Santos-Bulega, and F. Zamora. 2006. Influence of micro-oxygenation treatment before oak aging on phenolic compounds composition, astringency, and color of red wine. J. Agric. Food Chem. 54:4246-4252.
21. Dixon, R.A., D.Y. Xie, and S.B. Sharma. 2005. Proanthocyanidins - a final frontier in flavonoid research? New Phytol. 165:9-28.
22. Dokoozlian, N.K., and W.M. Kliewer. 1996. Influence of light on grape berry growth and composition varies during fruit development. J. Am. Soc. Hort. Sci. 121:869-874.
23. Downey, M.O., J.S. Harvey, and S.P. Robinson. 2003. Analysis of tannins in seeds and skins of Shiraz grapes throughout berry development. Aust. J. Grape Wine Res. 9:15-27.
24. Downey, M.O., J.S. Harvey, and S.P. Robinson. 2004. The effect of bunch shading on berry development and flavonoid accumulation in Shiraz grapes. Aust. J. Grape Wine Res. 10:55-73.
25. Drinkine, J., P. Lopes, J.A. Kennedy, P.-L. Teissedre, and C. Saucier. 2007a. Analysis of ethylidene-bridged flavan-3-ols in wine. J. Agric. Food Chem. 55:1109-1116.
26. Drinkine, J., P. Lopes, J.A. Kennedy, P.-L. Teissedre, and C. Saucier. 2007b. Ethylidene-bridged tannins in red wine and correlation with wine age. J. Agric. Food Chem. 55:6292-6299.
27. Eglinton, J., M. Griesser, P. Henschke, M. Kwiatkowski, M. Parker, and M. Herderich. 2004. Yeast mediated formation of pigmented polymers in red wine. Pages 125-142. In:Red Wine Color: Revealing the Mysteries. A.L. Waterhouse, J. Kennedy (eds.). ACS Symposium series 886, American Chemical Society. Washington, DC, USA.
28. Es-Safi, N., H. Fulcrand, V. Cheynier, and M. Moutounet. 1999. Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system. J. Agric. Food Chem. 47:2096-2102.
29. Fernández, K., J.A. Kennedy, and E. Agosin. 2007. Characterization of grape and wine proanthocyanidins of Vitis vinifera cv. Carmenere. J. Agric. Food Chem. 55:3675-3680.
30. Fernández, K., and E. Agosin. 2007. Quantitative analysis of red wine tannins using fourier-transform mid-infrared spectrometry. J. Agric. Food Chem. 55:7294-7300.
31. Fischer, U., R.B. Boulton, and A.C. Noble. 1994. Physiological factors contributing to the variability of sensory assessments: relationship between salivary flow rate and temporal perception of gustatory stimuli. Food Qual. Pref. 5: 55-64.
32. Fischer, U., and A.C. Noble. 1994. The effect of ethanol, catechin concentration and pH on sourness and bitterness of wine. Am. J. Enol. Vitic 45:6-10.
33. Fulcrand, H., C. Benabdeljalil, J. Rigaud, V. Cheynier, V., and M. Moutounet. 1998. A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 47:1401-1407.
34. Gao, Y., and G.A. Cahoon. 1994. Cluster shading effects on fruit quality, fruit skin color, and anthocyanin content and composition in Reliance (Vitis hybrid). Vitis 33:205-209.
35. Gawel, R. 1998. Red wine astringency: a review. Aust. J. Grape Wine Res. 4:74-95.
36. Gawel, R., A. Oberholster, and I.L. Francis. 2000. A mouth-feel wheel: Terminology for communicating the mouth-feel characteristics of red wine. Aust. J. Grape Wine Res. 6:203-207.
37. Gawel, R., P.G. Iland, and I.L. Francis. 2001.Characterizing the astringency of red wine: a case study. Food Qual. Pref. 12:83-94.
38. Haslam, E. 1980. In vino veritas: oligomeric procyanidins and the ageing of red wines. Phytochemistry 19:2577-2582.
39. Haslam, E. 1998. Taste, bitterness and astringency. Pages 178-225. In: E. Haslam (ed.). Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action. Cambridge: Cambridge University Press. UK.
40. He, J., C. Santos Buelga, N. Mateus, and V.A.P. de Freitas. 2006. Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques. J. Chromatogr. A 1134:215-225.
41. Hayasaka, Y., and J.A. Kennedy. 2003. Mass spectrometric evidence for the formation of pigmented polymers in red wine. Aust. J. Grape Wine Res. 9:210-220.
42. Ishikawa, T., and A.C. Noble. 1995. Temporal perception of astringency and sweetness in red wine. Food Qual. Pref. 6:27-33.
43. Jurd, L. 1967a. Anthocyanidins and related compounds-XI. Catechin-flavylium salt condensation reactions. Tetrahedron 23:1057-1064.
44. Jurd, L. 1967b. Catechin-flavylium salt condesation reactions. Tetrahedron 23:1057-1064.
45. Jurd, L. 1969. Review of polyphenol condensation reactions and their possible occurrence in the aging of wines. Am. J. Enol. Vitic. 20:191-195.
46. Kallithraka, S., J. Bakker, and M.N. Clifford. 1997. Evaluation of bitterness and astringency of (+)- catechin and (-)-epicatechin in red wine and in model solution. J. Sensory Stud. 12:25-37.
47. Kennedy, J.A., M.A. Matthews, and A.L. Waterhouse. 2000. Changes in grape seed polyphenols during ripening. Phytochemistry 55:77-85.
48. Kennedy, J.A., Y. Hayasaka, S. Vidal, E.J. Waters, and G.P. Jones. 2001. Composition of grape skin proanthocyanidins at different stages of berry development. J Agric. Food Chem. 49:5348-5355.
49. Kennedy, J.A., M.A. Matthews, and A.L. Waterhouse. 2002. Effect of maturity and vine water status on grape skin and wine flavonoids. Am. J. Enol. Vitic. 53:268-274.
50. Kennedy, J.A. 2002. Understanding berry development. Practical Winery and Vineyard July/August. p. 14-23.
51. Kliewer, W.M., and R.E. Torres. 1972. Effect of controlled day and night temperatures on grape coloration. Am. J. Enol. Vitic. 23:71-77.
52. Kliewer, W.M. 1977. Influence of temperature, solar radiation and nitrogen on coloration and composition of Emperor grapes. Am. J. Enol. Vitic. 28:96-103.
53. Kovac, V., E. Alonso, M. Bourzeix, and E. Revilla. 1992. Effect of several enological practices on the content of catechins and proanthocyanidins of red wines. J. Agric. Food Chem. 40:1953- 1957.
54. Laurie, V.F., and A.L. Waterhouse. 2006a. Glyceraldehyde bridging between flavanols and malvidin-3-glucoside in model solutions. J. Agric. Food Chem. 54:9105-9111.
55. Laurie, V.F., and A.L. Waterhouse. 2006b. Oxidation of glycerol in the presence of hydrogen peroxide and iron in model solutions and wine. Potential effects on wine color. J. Agric. Food Chem. 54:4668-4673.
56. Lesschaeve, I., and A.C. Noble. 2005. Polyphenols: factors influencing their sensory properties and their effects on food and beverage preferences. Am. J. Clin. Nutr. 81:330s-335s.
57. Mateus, N., S. Marques, A.C. Gonçalves, J.M. Machado, and V. de Freitas. 2001. Proanthocyanidin composition of red Vitis vinifera varieties from the Duoro valley during ripening: Influence of cultivation altitude. Am. J. Enol. Vitic. 52:115-121.
58. Mateus, N., E. Carvalho, R.F.A. Carvalho, A. Melo, M.A. Gonzales-Paramas, C. Santos-Buelga, and V. A.P. de Freitas. 2003. Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol occurring in aging red wines. J. Agric. Food Chem. 51:277-282.
59. Mateus, N., J. Oliveira, C. Santos-Buelga, A.M.S. Silva, and V.A.P. de Freitas. 2004.NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment (a portisin). Tetrahedron Lett. 45:3455-3457.
60. Mayen, M., J. Merida, and M. Medina. 1994. Free anthocyanins and polymeric pigments during the fermentation and post-fermentation standing of musts from Cabernet Sauvignon and Tempranillo grapes. Am J. Enol. Vitic. 45:161-166.
61. Mercurio, M.D., R.G. Dambergs, M.J. Herderich, and P.A. Smith. 2007. High throughput analysis of red wine and grape phenolics - adaptation and validation of methyl cellulose precipitable tannin assay and modified Somers color assay to a rapid 96 well plate format. J. Agric. Food Chem. 55:4651-4657.
62. Nagel, C.W., and L.W. Wulf. 1979. Changes in the anthocyanins, flavonoids and hydroxycinnamic acid esters during fermentation and aging of Merlot and Cabernet Sauvignon. Am. J. Enol. Vitic. 30:111-116.
63. Noble, A.C. 1994. Bitterness in wine. Physiol. Behav. 6:1251-1255.
64. Ojeda, H., C. Andary, E. Kraeva, A. Carbonneau, and A. Deloire. 2002. Influence of pre- and postveraison water deficit on synthesis and concentration of skin phenolic compounds during berry growth of Vitis vinifera cv. Shiraz. Am. J. Enol. Vitic. 53:261-267.
65. Ough, C.S., and M.A. Amerine. 1961. Studies on controlled fermentation V. Effects on color, composition and quality of red wine. Am. J. Enol. Vitic. 12:9-19.
66. Pastor del Rio, J., and J.A. Kennedy. 2006.Development of proanthocyanidins in Vitis vinifera L. cv. Pinot noir grapes and extraction into wine. Am. J. Enol. Vitic. 57:125-131.
67. Peleg, H., K.K. Bodine, and A.C. Noble. 1998. The influence of acid on astringency of alum and phenolic compounds. Chem. Senses 23:371-378.
68. Pena-Neira, A., A. Caceres, C. Pastenes. 2007. Low molecular weight phenolic and anthocyanin composition of grape skins from cv. Syrah (Vitis vinifera L.) in the Maipo Valley (Chile): Effect of clusters thinning and vineyard yield. Food Sci. Technol. Int. 13:153-158.
69. Peyrot des Gachons, C., and J.A. Kennedy. 2003. Direct method for determining seed and skin proanthocyanidin extraction in red wine. J. Agric. Food Chem. 51:5877-5881.
70. Price, S.F., P.J. Breen, M. Valladao, and B.T. Watson. 1995. Cluster exposure and quercetin in Pinot noir grapes and wine. Am. J. Enol. Vitic. 46:187-194.
71. Remy, S., H. Fulcrand, B. Labarbe, V. Cheynier, and M. Moutounet. 2000. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions. J. Sci. Food Agric. 80:745-751.
72. Ribéreau-Gayon, P. 1959. Recherches sur les anthocyannes des végétaux. Application au genre Vitis. Librairie General de l'Enseignement. Paris, France.
73. Ribéreau-Gayon, P. 1963. Les acides-phénols de Vitis vinifera. Compt. Rend. 256:4108-4111.
74. Ribéreau-Gayon, P. 1964. Les composés phénoliques du raisin et du vin. II. Les flavonosides et les anthocyanosides. Ann. Physiol. Vég. 6:211-242.
75. Ribéreau-Gayon, P. 1965. Identification d'esters des acides des acides cinnamiques et l'acide tartrique dans les limbes et les baies de Vitis vinifera. Compt. Rend. 260:341-343.
76. Ribéreau-Gayon, P. 1968. Les Composés Phénololiques des Végétaux. Dunod, Paris, France. p. 264.
77. Ribéreau-Gayon, P., P. Sudraud, J.C. Milhé, and A. Canbas. 1970. Reserches technologiques sur les composes phenoliques des vin rouges II. Les factors de dissolution des composes phénoliques. Conn. Vigne Vin 4:133-144.
78. Ribéreau-Gayon, P., and J.C. Milhé. 1970. Reserches technologiques sur les composes phenoliques des vin rouges I. Influence des differentes parties de la grappe. Conn. Vigne Vin 4:63-74.
79. Ribéreau-Gayon, P. 1972. Évolution des composés phénoliques au cours de la maturation du raisin. II. Discussion des résultats obtenus en 1969, 1970, et 1971. Conn. Vigne Vin 6:161-175.
80. Ribéreau-Gayon, P., P. Pontallier, and Y. Glories. 1983. Some interpretations of colour changes in young red wines during their conservation. J. Sci. Food Agric. 34:505-516.
81. Riou, V., A. Vernhet, T. Doco, and M. Moutounet. 2001. Aggregation of grape seed tannins in model wine-effect of wine polysaccharides. Food Hydrocolloids 16:17-23.
82. Robichaud, J.L., and A.C. Noble. 1990. Astringency and bitterness of selected phenolics in wine. J. Sci. Food Agric. 53:343-353.
83. Romeyer, F.M., J.J. Macheix, J.P. Goiffon, C.C. Reminiac, and J.C. Sapis. 1983. The browning capacity of grapes. 3. Changes and importance of hydroxycinnamic acid-tartaric acid esters during development and maturation of the fruit. J. Agric. Food Chem. 31:346-349.
84. Salas, E., C. Le Guernevé, H. Fulcrand, C. Poncet-Legrand, and V. Cheynier. 2004. Structure determination and color properties of a newly synthesized direct-linked flavanol-anthocyanin dimer. Tetrahedron Lett. 45: 8725-8729.
85. Saucier, C., C. Guerra, M. Laguerre, and Y. Glories. 1997a. (+)-catechin-acetaldehyde condensation products in relation with wine-ageing. Phytochemistry 46:229-234.
86. Saucier, C., G. Bourgeois, C. Vitry, D. Roux, and Y. Glories. 1997b. Characterization of (+)-catechin-acetaldehyde polymers: a model for colloidal state of wine polyphenols. J. Agric. Food Chem. 45:1045-1049.
87. Schwarz, M., P. Quast, D. von Baer, and P. Winterhalter. 2003. 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. 51:6261-6267.
88. Scudamore-Smith, P.D., R.L. Hooper, and E.D. McLaran. 1990. Color and phenolic changes of Cabernet Sauvignon wine made by simultaneous yeast/bacterial fermentation and extended pomace contact. Am. J. Enol. Vitic. 41:57-67.
89. Singleton, V.L., and T.E. Kramling. 1976. Browning of white wines and an accelerated test for browning capacity. Am. J. Enol. Vitic. 27:157-160.
90. Smart, R.E., S.M. Smith, and R.V. Winchester. 1988. Light quality and quantity effects on fruit ripening for Cabernet Sauvignon. Am. J. Enol. Vitic. 39:250-258.
91. Smith, A.K., H. June, and A.C. Noble. 1996. Effects of viscosity on the bitterness and astringency of grape seed tannin. Food Qual. Pref. 7:161-166.
92. Somers, T.C. 1971. The polymeric nature of wine pigments. Phytochemistry 10:2175-2186.
93. Spayd, S.E., J.M. Tarara, D.L. Mee, and J.C. Ferguson. 2002. Separation of sunlight and temperature effects on the composition of Vitis vinifera cv. Merlot berries. Am. J. Enol. Vitic. 53:171-182.
94. Timberlake, C.F., and P. Bridle. 1976. Interactions between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. Am. J. Enol. Vitic. 27:97-105.
95. Trillat, A. 1908a. L'aldehyde acétique dans le vin, son origine et ses effets. Ann. De l'Institut Pasteur 22:704-719.
96. Trillat, A. 1908b. L'aldehyde acétique dans le vin, son origine et ses effets. Ann. De l'Institut Pasteur 22:753-762.
97. Trillat, A. 1908c. L'aldehyde acétique dans le vin, son origine et ses effets. Ann. De l'Institut Pasteur 22:876-895.
98. Vidal, S., P. Courcoux, L. Francis, M. Kwiatkowski, R. Gawel, P. Williams, E. Waters, and V. Cheynier. 2004a. Use of an experimental design approach for evaluation of key wine components on mouth-feel perception. Food Qual. Pref. 15:209-217.
99. Vidal, S., P. Courcoux, L. Francis, P. Williams, M. Kwiatkowski, R. Gawel, V. Cheynier, and E. Waters. 2004b. The mouth-feel properties of polysaccharides and anthocyanins in a wine like medium. Food Chem. 85:519-525.
100. Vidal, S., L. Francis, S. Guyot, N. Marnet, M. Kwiatkowski, R. Gawel, V. Cheynier, and E. J. Waters. 2003. The mouth-feel properties of grape and apple proanthocyanidins in a wine-like medium. J. Sci. Food Agric. 83:564-573.
101. Vivar-Quintana, A.M., C. Santos-Buelga, and J.C. Rivas-Gonzalo. 2002. Anthocyanin-derived pigments and colour of red wines. Anal. Chim. Acta 458:147-155.
102. Waterhouse, A.L., and V.F. Laurie. 2006. Oxidation of wine phenolics: A critical evaluation and hypothesis. Am. J. Enol. Vitic. 57:306-313.
103. Wildenradt, H.L., and V.L. Singleton. 1974. The production of aldehydes as a result of oxidation of polyphenolic compounds and its relation to wine aging. Am. J. Enol. Vitic. 25:119-126.
104. Winkel-Shirley, B. 2001. It takes a Garden. How work on diverse plant species has contributed to an understanding of flavonoid metabolism. Plant Physiol. 127:1399-1404.
105. Xie, D.Y., S.B. Sharma, N.L. Paiva, D. Ferreira and R.A. Dixon. 2003. Role of anthocyanidin reductase, encoded by BANYULS in plant flavonoid biosynthesis. Science 299:396-399.
106. Zimman, A., W.S. Joslin, M.L. Lyon, J. Meier, and A.L. Waterhouse. 2002. Maceration variables affecting phenolic composition in commercial-scale Cabernet Sauvignon winemaking trials. Am. J. Enol. Vitic. 53:93-98.