1932

Abstract

We review the extraction into wine and evolution of major phenolic classes of sensory relevance. We present a historical background to highlight that previously established aspects of phenolic extraction and retention into red wine are still subjects of much research. We argue that management of the maceration length is one of the most determining factors in defining the proportion and chemical fate of phenolic compounds in wine. The extraction of anthocyanins, flavonols, flavan-3-ols, and oligomeric and polymeric proanthocyanidins (PAs) is discussed in the context of their individual extraction patterns but also with regard to their interaction with other wine components. The same approach is followed to present the sensory implications of phenolic and phenolic-derived compounds in wine. Overall, we conclude that the chemical diversity of phenolic compounds in grapes is further enhanced as soon as vacuolar and pulp components are released upon crushing, adding a variety of new sensory dimensions to the already present chemical diversity. Polymeric pigments formed by the covalent reaction of anthocyanin and PAs are good candidates to explain some of the observed sensory changes in the color, taste, and mouthfeel attributes of red wines during maceration and aging.

Loading

Article metrics loading...

/content/journals/10.1146/annurev-food-030713-092438
2014-02-28
2024-04-13
Loading full text...

Full text loading...

/deliver/fulltext/food/5/1/annurev-food-030713-092438.html?itemId=/content/journals/10.1146/annurev-food-030713-092438&mimeType=html&fmt=ahah

Literature Cited

  1. Adams DO. 2006. Phenolics and ripening in grape berries. Am. J. Enol. Vitic. 57:249–56 [Google Scholar]
  2. Adams DO, Harbertson JF, Picciotto EA. 2004. Fractionation of red wine polymeric pigments by protein precipitation and bisulfite bleaching. Red Wine Colour: Revealing the Mysteries AL Waterhouse, JA Kennedy 275–88 Washington, DC: Am. Chem. Soc314 [Google Scholar]
  3. Adams DO, Scholz RC. 2008. Tannins – the problem of extraction. Proc. 13th Aust. Wine Ind. Tech. Conf. Aust. Soc. Vitic. Oenology, Adelaide, Aust.160–64 [Google Scholar]
  4. Alcalde-Eón C, Escribano-Bailón MT, Santos-Buelga C, Rivas-Gonzalo JC. 2006. Changes in the detailed pigment composition of red wine during maturity and ageing. A comprehensive study. Anal. Chim. Acta 513:305–18 [Google Scholar]
  5. Alcalde-Eón C, Escribano-Bailon MT, Santos-Buelga C, Rivas-Gonzalo JC. 2007. Identification of dimeric anthocyanins and new oligomeric pigments in red wine by means of HPLC-DAD-ESI/MSn. J. Mass Spectrom. 42:735–48 [Google Scholar]
  6. Amrani-Joutei K, Glories Y, Mercier M. 1994. Localization of tannins in grape berry skins. Vitis 33:133–38 [Google Scholar]
  7. Andersen OM, Jordheim M. 2006. The anthocyanins. Flavonoids: Chemistry, Biochemistry and Applications M Andersen, KR Markham 452–71 Boca Raton, FL: CRC Press1256 [Google Scholar]
  8. Aron PM, Kennedy JA. 2007. Compositional investigation of phenolic polymers isolated from Vitis vinifera L. cv. Pinot noir during fermentation. J. Agric. Food Chem. 55:5670–80 [Google Scholar]
  9. Asenstorfer RE, Iland PG, Tate ME, Jones GP. 2003. Charge equilibria and pKa of malvidin-3-glucoside by electrophoresis. Anal. Biochem. 318:291–99 [Google Scholar]
  10. Bajec MR, Pickering G. 2008. Astringency: mechanisms and perception. Crit. Rev. Food Sci. Nutr. 48:858–75 [Google Scholar]
  11. Bakker J, Timberlake CF. 1997. Isolation, identification, and characterization of new color-stable anthocyanins occurring in some red wines. J. Agric. Food Chem. 45:35–43 [Google Scholar]
  12. Baldi A, Romani A, Mulinacci N, Vincieri FF, Casetta B. et al. 1995. HPLC/MS application to anthocyanins of Vitis vinifera L. J. Agric. Food Chem. 48:2104–9 [Google Scholar]
  13. Bate-Smith E. 1973. Haemanalysis: The concept of relative astringency. Phytochemistry 12:907–12 [Google Scholar]
  14. Baxter NJ, Lilley TH, Haslam E, Williamson MP. 1997. Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemisty 36:5566–77 [Google Scholar]
  15. Bennick A. 2002. Interaction of plant polyphenol with salivary proteins. Crit. Rev. Oral Biol. Med. 13:184–96 [Google Scholar]
  16. Berg HW, Akiyoshi M. 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 [Google Scholar]
  17. Berg HW, Akiyoshi M. 1958. Further studies of the factors affecting the extraction of color and tannin from red grapes. Food Res. 23:511–17 [Google Scholar]
  18. Bindon KA, Bacic A, Kennedy JA. 2012. Tissue-specific and developmental modification of grape cell walls influences the adsorption of proanthocyanidins. J. Agric. Food Chem. 60:9249–60 [Google Scholar]
  19. Bindon KA, Kennedy JA. 2011. Ripening-induced changes in grape skin proanthocyanidins modify their interaction with cell walls. J. Agric. Food Chem. 59:2696–707 [Google Scholar]
  20. Bindon KA, Smith PA, Holt H, Kennedy JA. 2010a. Interaction between grape-derived proanthocyanidins and cell wall material. 2. Implications for vinification. J. Agric. Food Chem. 58:10736–46 [Google Scholar]
  21. Bindon KA, Smith PA, Kennedy JA. 2010b. Interaction between grape derived proanthocyanidins and cell wall material. 1. Effect on proanthocyanidin composition and molecular mass. J. Agric. Food Chem. 58:2520–28 [Google Scholar]
  22. Boulton RB. 2001. The copigmentation of anthocyanins and its role in the color of red wine: A critical review. Am. J. Enol. Vitic. 52:67–87 [Google Scholar]
  23. Boulton RB, Singleton VL, Bisson LF, Kunkee RE. 1996. Principles and Practices of Winemaking New York: Chapman & Hall604
  24. Breslin PA, Gilmore M, Beauchamp GK, Green BG. 1993. Psychological evidence that astringency is a tactile sensation. Chem. Senses 18:273–84 [Google Scholar]
  25. Burns J, Gardner PT, Matthews D, Duthie GG, Lean ME, Crozier A. 2001. Extraction of phenolics and changes in antioxidant activity of red wines during vinification. J. Agric. Food Chem. 49:5797–808 [Google Scholar]
  26. Busse-Valverde N, Bautista-Ortín AB, Gómez-Plaza E, Fernández-Fernández JI, Gil-Muñoz R. 2012. Influence of skin maceration time on the proanthocyanidin content of red wines. Eur. Food Res. Technol. 235:1117–23 [Google Scholar]
  27. Cai Y, Gaffney SH, Lilley TH, Haslam E. 1989. Carbohydrate-polyphenol complexation. Chemistry and Significance of Condensed Tannins RW Hemingway, JJ Karchesy, SJ Braham 307–22 New York: Plenum553 [Google Scholar]
  28. Canals R, Llaudy MC, Valls J, Canals JM, Zamora F. 2005. 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. 53:4019–25 [Google Scholar]
  29. Casassa LF, Beaver CW, Mireles MS, Harbertson JF. 2013a. Effect of extended maceration and ethanol concentration on the extraction and evolution of phenolics, color components and sensory attributes of Merlot wines. Aust. J. Grape Wine Res. 19:25–39 [Google Scholar]
  30. Casassa LF, Larsen RC, Beaver CW, Mireles MS, Keller M. et al. 2013b. Impact of extended maceration and regulated deficit irrigation (RDI) in Cabernet Sauvignon wines: characterization of proanthocyanidin distribution, anthocyanin extraction, and chromatic properties. J. Agric. Food Chem. 61:6446–57 [Google Scholar]
  31. Castellarin SD, Di Gaspero G, Marconi R, Nonis A, Peterlunger E. et al. 2006. Colour variation in red grapevines (Vitis Vinifera L.): Genomic organisation, expression of flavonoid 3′-hydroxylase, flavonoid 3′,5′-hydroxylase genes and related metabolite profiling of red cyanidin/blue delphinidin-based anthocyanins in berry skin. BMC Genomics 7:1–17 [Google Scholar]
  32. Castillo-Muñoz N, Gómez-Alonso S, García-Romero E, Gómez MV, Velders AH, Hermosín-Gutiérrez I. 2009. Flavonol 3-O-glycosides series of Vitis vinifera cv. Petit verdot red wine grapes. J. Agric. Food Chem. 57:209–19 [Google Scholar]
  33. Castillo-Muñoz N, Gómez-Alonso S, García-Romero E, Hermosín-Gutiérrez I. 2007. Flavonol profiles of Vitis Vinifera L. red grapes and their single-cultivar wines. J. Agric. Food Chem. 55:992–1002 [Google Scholar]
  34. Cerpa-Calderón FK, Kennedy JA. 2008. Berry integrity and extraction of skin and seed proanthocyanidins during red wine fermentation. J. Agric. Food Chem. 56:9006–14 [Google Scholar]
  35. Charlton AJ, Baxter NJ, Lilley TH, Haslam E, McDonald CJ, Williamson MP. 1996. Tannin interactions with a full-length human salivary proline-rich protein display a stronger affinity than with single proline-rich repeats. FEBS Lett. 382:289–92 [Google Scholar]
  36. Charlton AJ, Baxter NJ, Lokmankhan M, Moir AJG, Haslam E. et al. 2002. Polyphenol/peptide binding and precipitation. J. Agric. Food Chem. 50:1593–601 [Google Scholar]
  37. Cheynier V. 2006. Flavonoids in wine. Flavonoids: Chemistry, Biochemistry, and Applications M Andersen, KR Markham 443–70 Boca Raton, FL: CRC Press1256 [Google Scholar]
  38. Cheynier V, Dueñas-Paton M, Salas E, Maury C, Souquet JM. et al. 2006. Structure and properties of wine pigments and tannins. Am. J. Enol. Vitic. 57:298–305 [Google Scholar]
  39. Cheynier V, Prieur C, Guyot S, Rigaud J, Moutounet M. 1997. The structures of tannins in grapes and wines and their interactions with proteins. Wine: Nutritional and Therapeutic Benefits TR Watkins 81–93 Washington, DC: ACS Symp. Ser296 [Google Scholar]
  40. Cheynier V, Rigaud J. 1986. HPLC separation and characterization of flavonols in the skins of Vitis vinifera var. Cinsault. Am. J. Enol. Vitic. 37:248–52 [Google Scholar]
  41. Chira K, Schmauch G, Saucier C, Fabre S, Teissedre P-L. 2009. Grape variety effect on proanthocyanidin composition and sensory perception of skin and seed tannin extracts from Bordeaux wine grapes (Cabernet Sauvignon and Merlot) for two consecutive vintages (2006 and 2007). J. Agric. Food Chem. 57:545–53 [Google Scholar]
  42. Cortell JM, Halbleib M, Gallaguer AV, Righetti TL, Kennedy JA. 2007. Influence of vine vigor on grape (Vitis vinifera L. cv. Pinot noir) anthocyanins. 2. Anthocyanins and pigmented polymers in wine. J. Agric. Food Chem. 55:6585–95 [Google Scholar]
  43. Cortell JM, Kennedy JA. 2006. Effect of shading on accumulation of flavonoid compounds in (Vitis vinifera L.) Pinot noir and extraction in a model system. J. Agric. Food Chem. 54:8510–20 [Google Scholar]
  44. Czochanska Z, Foo LY, Newman RH, Porter LJ. 1980. Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight. J. Chem. Soc. Perkin Trans. 1:2278–86 [Google Scholar]
  45. Danilewicz JC. 2003. Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: central role of iron and copper. Am. J. Enol. Vitic. 54:73–85 [Google Scholar]
  46. Danilewicz JC, Seccombe JT, Whelan J. 2008. Mechanism of interaction of polyphenols, oxygen, and sulfur dioxide in model wine and wine. Am. J. Enol. Vitic. 59:128–36 [Google Scholar]
  47. De Freitas VA, Carvalho E, Mateus N. 2003. Study of carbohydrate influence on protein-tannin aggregation by nephelometry. Food Chem. 81:503–9 [Google Scholar]
  48. De Freitas VA, Mateus N. 2001. Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 49:940–45 [Google Scholar]
  49. De Freitas VA, Mateus N. 2010. Formation of pyranoanthocyanins in red wines: a new and diverse class of anthocyanin derivatives. Anal. Bioanal. Chem. 401:1463–73 [Google Scholar]
  50. del Llaudy MC, Canals R, Canals JM, Zamora F. 2008. Influence of ripening stage and maceration length on the contribution of grape skins, seeds, and stems to phenolic composition and astringency in wine-simulated macerations. Eur. Food Res. Technol. 226:337–44 [Google Scholar]
  51. Delcambre A, Saucier C. 2012. Identification of new flavan-3-ol monoglycosides by UHPLC-ESI-Q-TOF in grapes and wine. J. Mass Spectrom. 47:727–36 [Google Scholar]
  52. Demiglio P, Pickering GJ. 2008. The influence of ethanol and pH on the taste and mouthfeel sensations elicited by red wine. J. Food Agric. Environ. 6:143–50 [Google Scholar]
  53. Downey MO, Harvey J, Robinson S. 2003. Analysis of tannins in seeds and skins of Shiraz grapes throughout berry development. Aust. J. Grape Wine Res. 9:15–27 [Google Scholar]
  54. Downey MO, Rochfort S. 2008. Simultaneous separation by reverse phase high-performance liquid chromatography and mass spectral identification of anthocyanins and flavonols in Shiraz grape skin. J. Chromatogr. A 1201:43–47 [Google Scholar]
  55. Dueñas M, Fulcrand H, Cheynier V. 2006. Formation of anthocyanin–flavanol adducts in model solutions. Anal. Chim. Acta 563:15–25 [Google Scholar]
  56. Elias RJ, Laurie VF, Ebeler SE, Wong JW, Waterhouse AL. 2008. Analysis of selected carbonyl oxidation products in wine by liquid chromatography with diode array detection. Anal. Chim. Acta 626:104–10 [Google Scholar]
  57. Escribano-Bailón MT, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C. 1995. Proanthocyanidins in skins from different grape varieties. Z. Lebensm. Unters. Forsch. 200:221–24 [Google Scholar]
  58. Es-Safi NE, Cheynier V, Moutounet M. 2000a. Study of the reactions between (+)-catechin and furfural derivatives in the presence or absence of anthocyanins and their implication in food color change. J. Agric. Food Chem. 48:5946–54 [Google Scholar]
  59. Es-Safi NE, Fulcrand H, Cheynier V, Moutounet M. 1999. Studies on the acetaldehyde-induced condensation of (−)-epicatechin and malvidin 3-O-glucoside in a model solution system. J. Agric. Food Chem. 47:2096–102 [Google Scholar]
  60. Es-Safi NE, Le Guernevé C, Fulcrand H, Cheynier V, Moutounet M. 2000b. Xanthylium salts formation involved in wine colour changes. Int. J. Food Sci. Technol. 35:63–74 [Google Scholar]
  61. Flamini R, Traldi P. 2010. Mass Spectrometry in Grape and Wine Chemistry Hoboken, NJ: Wiley348
  62. 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 47:1401–7 [Google Scholar]
  63. Fulcrand H, Cheynier V, Oszmianski J, Moutounet M. 1997. An oxidized tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-ol condensation. Phytochemistry 46:223–27 [Google Scholar]
  64. Gambuti A, Capuano R, Lecce L, Fragasso MG, Moio L. 2009. Extraction of phenolic compounds from ‘Aglianico’ and ‘Uva di Troia’ grape skins and seeds in model solutions: Influence of ethanol and maceration time. Vitis 4:193–200 [Google Scholar]
  65. Gawel R. 1998. Red wine astringency: A review. Aust. J. Grape Wine Res. 4:74–95 [Google Scholar]
  66. Gil M, Kontoudakis N, González E, Esteruelas M, Fort F. et al. 2012. Influence of grape maturity and maceration length on color, polyphenolic composition, and polysaccharide content of Cabernet Sauvignon and Tempranillo wines. J. Agric. Food Chem. 60:7988–8001 [Google Scholar]
  67. Gil-Muñoz R, Gómez-Plaza E, Martínez A, López-Roca JM. 1999. Evolution of phenolic compounds during wine fermentation and post-fermentation: influence of grape temperature. J. Food Comp. Anal. 12:259–72 [Google Scholar]
  68. Glories Y, Saucier C. 2000. Tannin evolution from grape to wine. Effects on wine taste. The ASEV 50th Anniv. Annu. Meet. J Ratz 353–55 Davis, CA: Am. Soc. Enol. Vitic. [Google Scholar]
  69. Gómez-Míguez M, Heredia FJ. 2004. Effect of the maceration technique on the relationships between anthocyanin composition and objective color of Syrah wines. J. Agric. Food Chem. 52:5117–23 [Google Scholar]
  70. Gómez-Plaza E, Romero-Cascales I, Fernández-Fernández JI, López-Roca JM. 2005. The maceration process during winemaking extraction of anthocyanins from grape skins into wine. Eur. Food Res. Tech. 221:163–67 [Google Scholar]
  71. González-Manzano S, Rivas-Gonzalo JC, Santos-Buelga C. 2004. Extraction of flavan-3-ols from grape seed and skin into wine using simulated maceration. Anal. Chim. Acta 513:283–89 [Google Scholar]
  72. González-Manzano S, Santos-Buelga C, Pérez-Alonso JJ, Rivas-Gonzalo JC, Escribano-Bailón MT. 2006. Characterization of the mean degree of polymerization of proanthocyanidins in red wines using liquid chromatography-mass spectrometry (LC-MS). J. Agric. Food Chem. 54:4326–32 [Google Scholar]
  73. González-Neves G, Gil G, Favre G, Ferrer M. 2012. Influence of grape composition and winemaking on the anthocyanin composition of red wines of Tannat. Int. J. Food Sci. Tech. 47:1–10 [Google Scholar]
  74. Guerrero RF, Liazid A, Palma M, Puertas B, González-Barrio R. et al. 2009. Phenolic characterization of red grapes autochthonous to Andalusia. Food Chem. 112:949–55 [Google Scholar]
  75. Hanlin RL, Hrmova M, Harbertson JF, Downey MO. 2010. Review: condensed tannin and grape cell wall interactions and their impact on tannin extractability into wine. Aust. J. Grape Wine Res. 16:173–88 [Google Scholar]
  76. Hanlin RL, Kelm MA, Wilkinson KL, Downey MO. 2011. Detailed characterization of proanthocyanidins in skin, seeds and wine of Shiraz and Cabernet Sauvignon wine grapes (Vitis vinifera). J. Agric. Food Chem. 59:13265–76 [Google Scholar]
  77. Harbertson JF, Kennedy JA, Adams DO. 2002. Tannin in skins and seeds of Cabernet Sauvignon, Syrah, and Pinot noir berries during ripening. Am. J. Enol. Vitic. 53:54–59 [Google Scholar]
  78. Harbertson JF, Mireles M, Harwood E, Weller KM, Ross CF. 2009. Chemical and sensory effects of saignée, water addition and extended maceration on high Brix must. Am. J. Enol. Vitic. 60:450–60 [Google Scholar]
  79. Harbertson JF, Spayd S. 2006. Measuring phenolics in the winery. Am. J. Enol. Vitic. 57:280–88 [Google Scholar]
  80. Haslam E. 1982. Proanthocyanidins. The Flavonoids: Advances in Research JB Harborne, TJ Mabry 417–47 London: Chapman & Hall744 [Google Scholar]
  81. Haslam E. 1998. Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action Cambridge, UK: Cambridge Univ. Press438
  82. Hayasaka Y, Kennedy JA. 2003. Mass spectrometric evidence for the formation of pigmented polymers in red wine. Aust. J. Grape Wine Res. 9:210–20 [Google Scholar]
  83. He F, He JJ, Pan QH, Duan CQ. 2010. Mass-spectrometry evidence confirming the presence of pelargonidin-3-O-glucoside in the berry skins of Cabernet Sauvignon and Pinot noir (Vitis vinifera L.). Aust. J. Grape Wine Res. 16:464–68 [Google Scholar]
  84. He F, Liang NN, Mu L, Pan QH, Wang J. et al. 2012. Anthocyanins and their variation in red wines II. Anthocyanin derived pigments and their color evolution. Molecules 17:1483–519 [Google Scholar]
  85. Hermosín-Gutiérrez I. 2003. Influence of ethanol content on the extent of copigmentation in a Cencibel young red wine. J. Agric. Food Chem. 51:4079–83 [Google Scholar]
  86. Hernández-Jiménez A, Kennedy JA, Bautista-Ortín AB, Gómez-Plaza E. 2012. Effect of ethanol on grape seed proanthocyanidin extraction. Am. J. Enol. Vitic. 63:57–61 [Google Scholar]
  87. Hilgard EW. 1887. The extraction of color and tannin during red-wine fermentations. Univ. Calif. Agric. Exp. Stn. Bull.77
  88. Hufnagel JC, Hofmann T. 2008a. Orosensory directed identification of astringent mouthfeel and bitter-tasting compounds in red wine. J. Agric. Food Chem. 56:1376–86 [Google Scholar]
  89. Hufnagel JC, Hofmann T. 2008b. Quantitative reconstruction of the nonvolatile sensometabolome of a red wine. J. Agric. Food Chem. 56:9190–99 [Google Scholar]
  90. Ishikawa T, Noble AC. 1995. Temporal perception of astringency and sweetness in red wine. Food Qual. Pref. 6:27–33 [Google Scholar]
  91. Jeffery DW, Parker M, Smith PA. 2008. Flavonol composition of Australian red and white wines determined by high-performance liquid chromatography. Aust. J. Grape Wine Res. 14:153–61 [Google Scholar]
  92. Jöbstl E, O'Connell J, Fairclough JPA, Williamson MP. 2004. Molecular model for astringency produced by polyphenol/protein interactions. Biomacromolecules 5:942–49 [Google Scholar]
  93. Jurd L. 1969. Review of polyphenol condensation reactions and their possible occurrence in the aging of wines. Am. J. Enol. Vitic. 20:191–95 [Google Scholar]
  94. Kallithraka S, Bakker J, Clifford MN. 1997a. Evaluation of bitterness and astringency of (+)-catechin and (−)-epicatechin in red wine and in model solution. J. Sens. Stud. 12:25–37 [Google Scholar]
  95. Kallithraka S, Bakker J, Clifford MN. 1997b. Effect of pH on astringency in model solutions and wines. J. Agric. Food Chem. 45:2211–16 [Google Scholar]
  96. Kallithraka S, Bakker J, Clifford MN, Vallis L. 2001. Correlations between saliva protein composition and some T-I parameters of astringency. Food Qual. Pref. 12:145–52 [Google Scholar]
  97. Kantz K, Singleton VL. 1991. Isolation and determination of polymeric polyphenols in wines using Sephadex LH-20. Am. J. Enol. Vitic. 42:309–16 [Google Scholar]
  98. Kelebek H, Canbas A, Selli A, Saucier C, Jourdes M, Glories Y. 2006. Influence of different maceration times on the anthocyanin composition of wines made from Vitis vinifera L., cvs. Bogazkere and Okuzgozu. J. Food Eng. 77:1012–17 [Google Scholar]
  99. Kennedy JA, Jones GP. 2001. Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. J. Agric. Food Chem. 49:1740–46 [Google Scholar]
  100. Kong JM, Chia LS, Goh NK, Chia TF, Brouillard R. 2003. Analysis and biological activities of anthocyanins. Phytochemistry 64:923–33 [Google Scholar]
  101. Koyama K, Goto-Yamamoto N, Hashizume K. 2007. Influence of maceration temperature in red wine vinification on extraction of phenolics from berry skins and seeds of grape (Vitis vinifera). Biosci. Biotechnol. Biochem. 71:958–65 [Google Scholar]
  102. Laurie VF, Waterhouse AL. 2006a. Glyceraldehyde bridging between flavanols and malvidin-3-glucoside in model solutions. J. Agric. Food Chem. 54:9105–11 [Google Scholar]
  103. Laurie VF, Waterhouse AL. 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. 54:4668–73 [Google Scholar]
  104. Le Bourvellec C, Bouchet B, Renard CM. 2005. Noncovalent interaction between procyanidins and apple cell wall material. Part III. Study on model polysaccharides. Biochim. Biophys. Acta 1725:10–18 [Google Scholar]
  105. Le Bourvellec C, Guyot S, Renard CM. 2004. Noncovalent interaction between procyanidins and apple cell wall material. Part I. Effect of some environmental parameters. Biochim. Biophys. Acta 1672:192–202 [Google Scholar]
  106. Le Bourvellec C, Renard CM. 2012. Interactions between polyphenols and macromolecules: quantification methods and mechanisms. Crit. Rev. Food Sci. Nutr. 52:213–48 [Google Scholar]
  107. Lee J, Kennedy JA, Devlin C, Redhead M, Rennaker C. 2008. Effect of early seed removal during fermentation on proanthocyanidin extraction in red wine: A commercial production example. Food Chem. 107:1270–73 [Google Scholar]
  108. Lesschaeve I, Noble AC. 2005. Polyphenols: factors influencing their sensory properties and their effects on food and beverage preferences. Am. J. Clin. Nutr. 81:330S–35 [Google Scholar]
  109. 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. J. Agric. Food Chem. 55:2698–704 [Google Scholar]
  110. Macheix JJ, Fleuriet A, Billot J. 1990. Fruit Phenolics Boca Raton, FL: CRC Press378
  111. Manfra M, De Nisco M, Bolognese A, Nuzzo V, Sofo A. et al. 2011. Anthocyanin composition and extractability in berry skin and wine of Vitis vinifera L. cv. Aglianico. J. Sci. Food Agric. 91:2749–55 [Google Scholar]
  112. Mateus N, Silva AMS, Vercauteren J, De Freitas V. 2001. Occurrence of anthocyanin-derived pigments in red wines. J. Agric. Food Chem. 49:4836–40 [Google Scholar]
  113. Mazauric JP, Salmon JM. 2005. Interactions between yeast lees and wine polyphenols during simulation of wine aging: I. Analysis of remnant polyphenolic compounds in the resulting wines. J. Agric. Food Chem. 53:5647–53 [Google Scholar]
  114. McManus JP, Davis KG, Lilley TH, Haslam E. 1981. The association of proteins with polyphenols. JCS Chem. Commun. 1981:309–11 [Google Scholar]
  115. McRae JM, Kennedy JA. 2011. Wine and grape tannin interactions with salivary proteins and their impact on astringency: a review of current research. Molecules 16:2348–64 [Google Scholar]
  116. McRae JM, Schulkin A, Kassara E, Holt EH, Smith PA. 2013. Sensory properties of wine tannin fractions: implications for in-mouth sensory properties. J. Agric. Food Chem. 61:719–27 [Google Scholar]
  117. Medina K, Boido E, Dellacassa E, Carrau F. 2005. Yeast interactions with anthocyanins during red wine fermentation. Am. J. Enol. Vitic. 56:104–9 [Google Scholar]
  118. Mehansho H, Butler LG, Carlson DM. 1987. Dietary tannins and salivary proline-rich proteins: Interactions, induction and defense mechanisms. Annu. Rev. Nutr. 7:423–40 [Google Scholar]
  119. Meyer J, Hernández R. 1970. Seed tannin extraction in Cabernet Sauvignon. Am. J. Enol. Vitic. 21:184–88 [Google Scholar]
  120. Mizuno H, Hirano K, Okamoto G. 2006. Effect of anthocyanin composition in grape skin on anthocyanic vacuolar inclusion development and skin coloration. Vitis 45:173–77 [Google Scholar]
  121. Monagas M, Bartolomé B, Gómez-Cordovés C. 2005. Updated knowledge about the presence of phenolic compounds in wine. Crit. Rev. Food Sci. Nutr. 45:85–118 [Google Scholar]
  122. Monagas M, Gómez-Cordovés C, Bartolomé B. 2007. Evaluation of different Saccharomyces cerevisiae strains for red winemaking. Influence on the anthocyanin, pyranoanthocyanin and non-anthocyanin phenolic content and colour characteristics of wines. Food Chem. 104:814–23 [Google Scholar]
  123. Monagas M, Gómez-Cordovés C, Bartolomé B, Laureano O, Ricardo da Silva JM. 2003. Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. cv. Graciano, Tempranillo, and Cabernet Sauvignon. J. Agric. Food Chem. 51:6475–81 [Google Scholar]
  124. Morata A, Gómez-Cordovés C, Colomo B, Suárez JA. 2003. Pyruvic acid and acetaldehyde production by different strains of Saccharomyces cerevisiae: relationship with Vitisin A and B formation in red wines. J. Agric. Food Chem. 51:7402–9 [Google Scholar]
  125. Morel-Salmi C, Souquet J-M, Bes M, Cheynier V. 2006. Effect of flash release treatment on phenolic extraction and wine composition. J. Agric. Food Chem. 54:4270–76 [Google Scholar]
  126. Moskowitz AH, Hrazdina G. 1981. Vacuolar contents of fruit subepidermal cells from Vitis species. Plant Physiol. 68:686–92 [Google Scholar]
  127. Nagel CW, Wulf L. 1979. Changes in the anthocyanins, flavonoids, and hydroxycinnamic acid esters during fermentation and aging of Merlot and Cabernet Sauvignon. Am. J. Enol. Vitic. 30:111–16 [Google Scholar]
  128. Niketic-Aleksic G, Hrazdina G. 1972. Quantitative analysis of the anthocyanin content in grape juices and wines. Lebensm. Wiss. Technol. 5:163–65 [Google Scholar]
  129. Noble AC. 1994. Bitterness in wine. Physiol. Behav. 56:1251–55 [Google Scholar]
  130. Oberholster A, Francis IL, Iland PG, Waters EJ. 2009. Mouthfeel of white wines made with and without pomace contact and added anthocyanins. Aust. J. Grape Wine Res. 15:59–69 [Google Scholar]
  131. Oliveira J, De Freitas V, Mateus N. 2009. A novel synthetic pathway to Vitisin B compounds. Tetrahedron Lett. 50:3933–35 [Google Scholar]
  132. Ough CS, Amerine MA. 1960. Experiments with controlled fermentations. IV. Red wines. Am. J. Enol. Vitic. 11:5–14 [Google Scholar]
  133. Ough CS, Amerine MA. 1961a. Studies on controlled fermentation. V. Effects on color, composition and quality of red wine. Am. J. Enol. Vitic. 12:9–19 [Google Scholar]
  134. Ough CS, Amerine MA. 1961b. Studies with controlled fermentation. VI. Effects of temperature and handling on rates, composition, and quality of wines. Am. J. Enol. Vitic. 12:117–28 [Google Scholar]
  135. Ozmianski J, Romeyer FM, Sapis JC, Macheix JJ. 1986. Grape seed phenolics: Extraction as affected by some conditions occurring during wine processing. Am. J. Enol. Vitic. 37:7–12 [Google Scholar]
  136. Peleg H, Gacon K, Schlich P, Noble AC. 1999. Bitterness and astringency of flavan-3-ol monomers, dimers and trimers. J. Sci. Food Agric. 1128:1123–28 [Google Scholar]
  137. Pérez-Magariño S, González-San José ML. 2004. 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. 52:1181–89 [Google Scholar]
  138. Peynaud É. 1984. Knowing and Making Wine Transl. A Spenser New York: Wiley-Intersci416 (In French)
  139. Peyrot des Gachons C, Kennedy JA. 2003. Direct method for determining seed and skin proanthocyanidin extraction into red wine. J. Agric. Food Chem. 51:5877–81 [Google Scholar]
  140. Pianet I, André Y, Ducasse MA, Tarascou I, Lartigue JC. et al. 2008. Modeling procyanidin self-association processes and understanding their micellar organization: a study by diffusion NMR and molecular mechanics. Langmuir 24:11027–35 [Google Scholar]
  141. Pinelo M, Laurie VF, Waterhouse AL. 2006. A simple method to separate red wine nonpolymeric and polymeric phenols by solid-phase extraction. J. Agric. Food Chem. 54:2839–44 [Google Scholar]
  142. Pissara J, Mateus N, Rivas-Gonzalo JC, De Freitas V. 2003. Reaction between malvidin 3-glucoside and (+)-catechin in model solutions containing different aldehydes. J. Food Sci. 68:476–81 [Google Scholar]
  143. Plumb GW, de Pascual-Teresa S, Santos-Buelga C, Cheynier V, Williamson G. 1998. Antioxidant properties of catechins and proanthocyanidins: effect of polymerisation, galloylation and glycosylation. Free Radic. Res. 29:351–58 [Google Scholar]
  144. Poncet-Legrand C, Gautier C, Cheynier V, Imberty A. 2007. Interactions between flavan-3-ols and poly (L-proline) studied by isothermal titration calorimetry: Effect of the tannin structure. J. Agric. Food Chem. 55:9235–40 [Google Scholar]
  145. Price SF, Breen PJ, Valladao M, Watson BT. 1995. Cluster sun exposure and quercetin in Pinot noir grapes and wine. Am. J. Enol. Vitic. 46:187–94 [Google Scholar]
  146. Prieur C, Rigaud J, Cheynier V, Moutounet M. 1994. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36:781–84 [Google Scholar]
  147. Puertas B, Guerrero RF, Jurado MS, Jimenez MJ, Cantos-Villar E. 2008. Evaluation of alternative winemaking processes for red wine color enhancement. Food Sci. Technol. Int. 14:21–28 [Google Scholar]
  148. Remy S, Fulcrand H, Labarbe B, Cheynier V, Moutounet M. 2000. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions. J. Sci. Food Agric. 80:745–51 [Google Scholar]
  149. Renard CM, Baron A, Guyot S, Drilleau JF. 2001. Interactions between apple cell walls and native apple polyphenols: quantification and some consequences. Int. J. Biol. Macromol. 29:115–25 [Google Scholar]
  150. Rentzsch M, Schwarz M, Winterhalter P. 2007. Pyranoanthocyanins: an overview on structures, occurrence, and pathways of formation. Trends Food Sci. Tech. 18:526–34 [Google Scholar]
  151. Ribéreau-Gayon P, Dubourdieu D, Donèche B, Lonvaud A. 1998. Traité d' Oenologie. 1. Microbiologie du Vin Vinifications. Paris: Ed. Dunod661
  152. Ricardo da Silva JM, Cheynier V, Souquet JM, Moutounet M, Cabanis JC, Bourzeix M. 1991. Interaction of grape seed procyanidins with various proteins in relation to wine fining. J. Sci. Food Agric. 57:111–25 [Google Scholar]
  153. Rivas-Gonzalo JC, Bravo-Haro S, Santos-Buelga C. 1995. Detection of compounds formed through the reaction of malvidin 3-monoglucoside and catechin in the presence of acetaldehyde. J. Agric. Food Chem. 43:1444–49 [Google Scholar]
  154. Robichaud JL, Noble AC. 1990. Astringency and bitterness of selected phenolics in wine. J. Sci. Food Agric. 53:343–53 [Google Scholar]
  155. Romero-Cascales I, Fernández-Fernández JI, López-Roca JM, Gómez-Plaza E. 2005. The maceration process during winemaking extraction of anthocyanins from grape skins into wine. Eur. Food Res. Technol. 221:163–67 [Google Scholar]
  156. Rossi JA, Singleton VL. 1966. Flavor effects and adsorptive properties of purified fractions of grape-seed phenols. Am. J. Enol. Vitic. 17:240–46 [Google Scholar]
  157. Rudnitskaya A, Nieuwoudt HE, Muller N, Legin A, du Toit M, Bauer FF. 2010. Instrumental measurement of bitter taste in red wine using an electronic tongue. Anal. Bioanal. Chem. 397:3051–60 [Google Scholar]
  158. Sáenz-Navajas MP, Ferreira V, Dizy M, Fernández-Zurbano P. 2010. Characterization of taste-active fractions in red wine combining HPLC fractionation, sensory analysis and ultra-performance liquid chromatography coupled with mass spectrometry detection. Anal. Chim. Acta 673:151–59 [Google Scholar]
  159. Salas E, Dueñas M, Schwarz M, Winterhalter P, Cheynier V, Fulcrand H. 2005. Characterization of pigments from different high speed countercurrent chromatography wine fractions. J. Agric. Food Chem. 53:4536–46 [Google Scholar]
  160. Salas E, Fulcrand H, Meudec E, Cheynier V. 2003. Reactions of anthocyanins and tannins in model solutions. J. Agric. Food Chem. 51:7951–61 [Google Scholar]
  161. Schwarz M, Quast P, von Baer D, Winterhalter P. 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. 51:6261–67 [Google Scholar]
  162. Scollary GR, Pásti G, Kállay M, Blackman J, Clark AC. 2012. Astringency response of red wines: potential role of molecular assembly. Trends Food Sci. Tech. 27:25–36 [Google Scholar]
  163. Scudamore-Smith PD, Hooper RL, McLaren ED. 1990. Color and phenolic changes of Cabernet Sauvignon wine made by simultaneous yeast/bacteria fermentation and extended pomace contact. Am. J. Enol. Vitic. 41:57–67 [Google Scholar]
  164. Singleton VL. 1992. Tannins and the qualities of wines. Plant Polyphenols: Synthesis, Properties, Significance RW Hemingway 859–80 New York: Plenum1077 [Google Scholar]
  165. Singleton VL, Draper DE. 1964. The transfer of polyphenolic compounds from grape seeds into wines. Am. J. Enol. Vitic. 15:34–40 [Google Scholar]
  166. Singleton VL, Noble AC. 1976. Wine flavor and phenolic substances. Phenolic, Sulfur and Nitrogen Compounds in Food Flavors G Charalambous, I Katz, pp. 47–70. ACS Symp. Ser. 26 Washington, DC: Am. Chem. Soc215 [Google Scholar]
  167. Singleton VL, Trousdale EK. 1992. Anthocyanin-tannin interactions explaining differences in polymeric phenols between white and red wines. Am. J. Enol. Vitic. 43:63–70 [Google Scholar]
  168. Sipiora MJ, Gutiérrez-Granda MJ. 1998. Effects of pre-véraison irrigation cut off and skin contact time on the composition, color and phenolic content of young Cabernet Sauvignon wines in Spain. Am. J. Enol. Vitic. 53:268–74 [Google Scholar]
  169. Somers TC. 1971. The polymeric nature of wine pigments. Phytochemistry 10:2175–86 [Google Scholar]
  170. Somers TC, Evans ME. 1977. Spectral evaluation of young red wines: Anthocyanin equilibria, total phenols, free and molecular SO2 and chemical age. J. Sci. Food Agric. 28:279–87 [Google Scholar]
  171. Somers TC, Evans ME. 1979. Grape pigment phenomena: interpretation of major colour losses during vinification. J. Sci. Food Agric. 30:623–33 [Google Scholar]
  172. Souquet JM, Cheynier V, Brossaud F, Moutounet M. 1996. Polymeric proanthocyanidins from grape skins. Phytochemisty 43:509–12 [Google Scholar]
  173. Spranger I, Clímaco MC, Sun B, Eiriz N, Fortunato C. et al. 2004. Differentiation of red winemaking technologies by phenolic and volatile composition. Anal. Chim. Acta 513:151–61 [Google Scholar]
  174. Su CT, Singleton VL. 1969. Identification of three flavan-3-ols from grapes. Phytochemisty 8:1553–58 [Google Scholar]
  175. Sun BS, de Sá MC, Leandro C, Caldeira I, Duarte FL, Spranger I. 2013. Reactivity of polymeric proanthocyanidins toward salivary proteins. J. Agric. Food Chem. 61:939–46 [Google Scholar]
  176. Sun BS, Pinto T, Leandro MC, Ricardo da Silva JM, Spranger MI. 1999. Transfer of catechins and proanthocyanidins from solid parts of the grape cluster into wine. Am. J. Enol. Vitic. 50:179–84 [Google Scholar]
  177. Thorngate JH, Noble AC. 1995. Sensory evaluation of bitterness and astringency of 3R(−)-epicatechin and 3S(+)-catechin. J. Sci. Food Agric. 67:531–35 [Google Scholar]
  178. Timberlake CF, Bridle P. 1976. Interactions between anthocyanins, phenolic compounds, and acetaldehyde and their significance in red wines. Am. J. Enol. Vitic. 27:97–105 [Google Scholar]
  179. Valentová H, Skrováková S, Panovská Z, Pokorny J. 2002. Time intensity studies of astringent taste. Food Chem. 78:29–37 [Google Scholar]
  180. Vasserot Y, Caillet S, Maujean A. 1997. Study of anthocyanin adsorption by yeast lees. Effect of some physico-chemical parameters. Am. J. Enol. Vitic. 48:433–37 [Google Scholar]
  181. Vidal S, Francis L, Guyot S, Marnet N, Kwiatkowski M. et al. 2003. The mouth-feel properties of grape and apple proanthocyanins in a wine-like medium. J. Sci. Food Agric. 83:564–73 [Google Scholar]
  182. Vidal S, Francis L, Noble AC, Kwiatkowski M, Cheynier V, Waters EJ. 2004a. Taste and mouth-feel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal. Chim. Acta 513:57–65 [Google Scholar]
  183. Vidal S, Meudec E, Cheynier V, Skouroumounis G, Hayasaka Y. 2004b. Mass spectrometric evidence for the existence of oligomeric anthocyanins in grape skins. J. Agric. Food Chem. 52:7144–51 [Google Scholar]
  184. Vrhovsek U, Vanzo A, Nemanic J. 2002. Effect of red wine maceration techniques on oligomeric and polymeric proanthocyanidins in wine, cv. Blaufrankisch. Vitis 41:47–51 [Google Scholar]
  185. Wang H, Race EJ, Shrikhande AJ. 2003. Anthocyanin transformation in Cabernet Sauvignon wine during aging. J. Agric. Food Chem. 51:7989–94 [Google Scholar]
  186. Waterhouse AL. 2002. Wine phenolics. Ann. N.Y. Acad. Sci. 957:21–36 [Google Scholar]
  187. Waterhouse AL, Laurie VF. 2006. Oxidation of wine phenolics: a critical evaluation and hypotheses. Am. J. Enol. Vitic. 57:306–13 [Google Scholar]
  188. Weber F, Greve K, Durner D, Fischer U, Winterhalter P. 2013. Sensory and chemical characterization of phenolic polymers from red wine obtained by gel permeation chromatography. Am. J. Enol. Vitic. 64:15–25 [Google Scholar]
  189. Wollmann N, Hofmann T. 2013. Compositional and sensory characterization of red wine polymers. J. Agric. Food Chem. 61:2045–61 [Google Scholar]
  190. Wu X, Beecher GR, Holden JM, Haytowitz DB, Gebhardt SE, Prior RL. 2006. Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J. Agric. Food Chem. 54:4069–75 [Google Scholar]
  191. Yaminishi T. 1990. Bitter compounds in tea. Bitterness in Foods and Beverages RL Rouseff 159–67 Amsterdam: Elsevier356 [Google Scholar]
  192. Yokotsuka K, Sato M, Ueno N, Singleton VL. 2000. Colour and sensory characteristics of Merlot red wines caused by prolonged pomace contact. J. Wine Res. 11:7–18 [Google Scholar]
  193. Zhu M, Phillipson D, Greengrass PM, Bowery NE, Cai Y. 1997. Plant polyphenols: Biologically active compounds or nonselective binders to protein?. Phytochemistry 44:441–47 [Google Scholar]
  194. Zimman A, Joslin WS, Lyon ML, Meier J, Waterhouse AL. 2002. Maceration variables affecting phenolic composition in commercial-scale cabernet sauvignon winemaking trials. Am. J. Enol. Vitic. 53:93–98 [Google Scholar]
/content/journals/10.1146/annurev-food-030713-092438
Loading
/content/journals/10.1146/annurev-food-030713-092438
Loading

Data & Media loading...

  • Article Type: Review Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error