Extraction, evolution, and sensory impact of phenolic compounds during red wine maceration

Annual Review of Food Science and Technology

Volumn 5, Issue 1, 2014, Pages 83-109

  Casassa, L Federico ^a,b   Harbertson, James F ^b  

^a INSTITUTO NACIONAL DE TECNOLOGÍA AGROPECUARIA INTA   (Argentina)

^b WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

Anthocyanins; Color; Mouthfeel; Polymeric pigments; Proanthocyanidins; Red wine production

Indexed keywords

CHEMICAL DIVERSITY; HISTORICAL BACKGROUND; INDIVIDUAL EXTRACTIONS; MACERATION LENGTHS; MOUTHFEEL; PHENOLIC COMPOUNDS; PROANTHOCYANIDINS; RED WINE;

BREWERIES; CHEMICAL COMPOUNDS; COLOR; EXTRACTION; POLYMERS; WINE;

ANTHOCYANINS;

ANTHOCYANIN; FLAVAN 3 OL; FLAVONOID; FLAVONOL DERIVATIVE; POLYMER; PROANTHOCYANIDIN;

CELL WALL; CHEMISTRY; COLOR; FERMENTATION; FLAVAN-3-OL; FOOD HANDLING; FRUIT; HUMAN; ISOLATION AND PURIFICATION; METHODOLOGY; REVIEW; SENSATION; TASTE; VITIS; WINE;

ANTHOCYANINS; CELL WALL; COLOR; FERMENTATION; FLAVONOIDS; FLAVONOLS; FOOD HANDLING; FRUIT; HUMANS; POLYMERS; PROANTHOCYANIDINS; SENSATION; TASTE; VITIS; WINE;

EID: 84897716066     PISSN: 19411413     EISSN: 19411421     Source Type: Journal    
DOI: 10.1146/annurev-food-030713-092438     Document Type: Article

References (387)

1. Adams DO. 2006. Phenolics and ripening in grape berries. Am. J. Enol. Vitic. 57:249-56
2. Adams DO, Harbertson JF, Picciotto EA. 2004. Fractionation of red wine polymeric pigments by protein precipitation and bisulfite bleaching. In Red Wine Colour: Revealing the Mysteries, ed. AL Waterhouse, JA Kennedy, pp. 275-88. Washington, DC: Am. Chem. Soc. 314 p.p.
3. Adams DO, Scholz RC. 2008. Tannins-The problem of extraction. In Proc. 13th Aust. Wine Ind. Tech. Conf., Aust. Soc. Vitic. Oenology, Adelaide, Aust., pp. 160-64
4. Alcalde-Éon C, Escribano-Bail ón 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
5. Alcalde-Éon 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
6. Amrani-Joutei K, Glories Y, Mercier M. 1994. Localization of tannins in grape berry skins. Vitis 33:133-38
7. Andersen OM, Jordheim M. 2006. The anthocyanins. In Flavonoids: Chemistry, Biochemistry and Applications, ed. M Andersen, KR Markham, pp. 452-71. Boca Raton, FL: CRC Press. 1256 p.p.
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
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
10. Bajec MR, Pickering G. 2008. Astringency: Mechanisms and perception. Crit. Rev. Food Sci. Nutr. 48:858-75
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
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
13. Bate-Smith E. 1973. Haemanalysis: The concept of relative astringency. Phytochemistry 12:907-12
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
15. Bennick A. 2002. Interaction of plant polyphenol with salivary proteins. Crit. Rev. Oral Biol. Med. 13:184-96
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
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
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
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
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
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
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
23. Boulton RB, Singleton VL, Bisson LF, Kunkee RE. 1996. Principles and Practices of Winemaking. New York: Chapman & Hall. 604 p.p.
24. Breslin PA, GilmoreM, Beauchamp GK, Green BG. 1993. Psychological evidence that astringency is a tactile sensation. Chem. Senses 18:273-84
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
26. Busse-Valverde N, Bautista-Ort́in AB, Gómez-Plaza E, Ferńandez-Ferńandez JI, Gil-Mu ? noz R. 2012. Influence of skin maceration time on the proanthocyanidin content of red wines. Eur. Food Res. Technol. 235:1117-23
27. Cai Y, Gaffney SH, Lilley TH, Haslam E. 1989. Carbohydrate-polyphenol complexation. In Chemistry and Significance of Condensed Tannins, ed. RW Hemingway, JJ Karchesy, SJ Braham, pp. 307-22. New York: Plenum. 553 p.p.
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
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
30. Casassa LF, Larsen RC, Beaver CW, Mireles MS, KellerM, 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
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
32. Castillo-Münoz N, Gómez-Alonso S, Garćia-Romero E, Gómez MV, Velders AH, Hermośin-Gutiérrez I. 2009. Flavonol 3-O-glycosides series of Vitis vinifera cv. Petit verdot red wine grapes. J. Agric. Food Chem. 57:209-19
33. Castillo-Münoz N, Gómez-Alonso S, Garćia-Romero E, Hermośin-Gutiérrez I. 2007. Flavonol profiles of Vitis Vinifera L. red grapes and their single-cultivar wines. J. Agric. Food Chem. 55:992-1002
34. Cerpa-Calder ón FK, Kennedy JA. 2008. Berry integrity and extraction of skin and seed proanthocyanidins during red wine fermentation. J. Agric. Food Chem. 56:9006-14
35. Charlton AJ, Baxter NJ, LilleyTH, 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
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
37. Cheynier V. 2006. Flavonoids in wine. In Flavonoids: Chemistry, Biochemistry, and Applications, ed.MAndersen, KR Markham, pp. 443-70. Boca Raton, FL: CRC Press. 1256 p.p.
38. Cheynier V, Dué nas-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
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. In Wine: Nutritional and Therapeutic Benefits, ed. TR Watkins, pp. 81-93. Washington, DC: ACS Symp. Ser. 296 p.p.
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
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 Bordeauxwine grapes (Cabernet Sauvignon and Merlot) for two consecutive vintages (2006 and 2007). J. Agric. Food Chem. 57:545-53
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
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
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
45. Danilewicz JC. 2003. Review of reactionmechanisms of oxygen and proposed intermediate reduction products in wine: Central role of iron and copper. Am. J. Enol. Vitic. 54:73-85
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
47. De Freitas VA, Carvalho E, Mateus N. 2003. Study of carbohydrate influence on protein-Tannin aggregation by nephelometry. Food Chem. 81:503-9
48. De Freitas VA, Mateus N. 2001. Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 49:940-45
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
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 winesimulated macerations. Eur. Food Res. Technol. 226:337-44
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
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
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
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
55. Dué nas M, Fulcrand H, Cheynier V. 2006. Formation of anthocyanin-flavanol adducts in model solutions. Anal. Chim. Acta 563:15-25
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
57. Escribano-Bail ón MT, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C. 1995. Proanthocyanidins in skins from different grape varieties. Z. Lebensm. Unters. Forsch. 200:221-24
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
59. Es-Safi NE, FulcrandH, CheynierV, 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. 47:2096-2102
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
61. Flamini R, Traldi P. 2010. Mass Spectrometry in Grape and Wine Chemistry. Hoboken, NJ: Wiley. 348 pp
62. ulcrand 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
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
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
65. Gawel R. 1998. Red wine astringency: A review. Aust. J. Grape Wine Res. 4:74-95
66. Gil M, Kontoudakis N, Gonźalez 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
67. Gil-Mu ? noz R, Gómez-Plaza E, Mart́inez A, Ĺ opez-Roca JM. 1999. Evolution of phenolic compounds during wine fermentation and post-fermentation: Influence of grape temperature. J. Food Comp. Anal. 12:259-72
68. Glories Y, Saucier C. 2000. Tannin evolution from grape to wine. Effects on wine taste. In The ASEV 50th Anniv. Annu. Meet., ed. J Ratz, pp. 353-55. Davis, CA: Am. Soc. Enol. Vitic
69. Gómez-ḾiguezM, 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
70. Ǵomez-Plaza E, Romero-Cascales I, Ferńandez- Ferńandez JI, Ĺ opez-Roca JM. 2005. Themaceration process during winemaking extraction of anthocyanins from grape skins into wine. Eur. Food Res. Tech. 221:163-67
71. Gonźalez-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
72. Gonzalez-Manzano S, Santos-Buelga C, Pérez-Alonso JJ, Rivas-Gonzalo JC, Escribano-Bail ón 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
73. Gonźalez-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
74. Guerrero RF, Liazid A, PalmaM, Puertas B, Gonźalez-Barrio R, et al. 2009. Phenolic characterization of red grapes autochthonous to Andalusia. Food Chem. 112:949-55
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
76. Hanlin RL, KelmMA, 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
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
78. Harbertson JF, Mireles M, Harwood E, Weller KM, Ross CF. 2009. Chemical and sensory effects of saigńee, water addition and extended maceration on high Brix must. Am. J. Enol. Vitic. 60:450-60
79. Harbertson JF, Spayd S. 2006. Measuring phenolics in the winery. Am. J. Enol. Vitic. 57:280-88
80. Haslam E. 1982. Proanthocyanidins. In The Flavonoids: Advances in Research, ed. JB Harborne, TJ Mabry, pp. 417-47. London: Chapman & Hall. 744 p.p.
81. Haslam E. 1998. Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action. Cambridge, UK: Cambridge Univ. Press. 438 p.p.
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
83. He F, He JJ, PanQH, 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
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
85. Hermośin-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
86. Herńandez-Jiḿenez A, Kennedy JA, Bautista-Ort́in AB, Gómez-Plaza E. 2012. Effect of ethanol on grape seed proanthocyanidin extraction. Am. J. Enol. Vitic. 63:57-61
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 astringentmouthfeel and bitter-Tasting compounds in red wine. J. Agric. Food Chem. 56:1376-86
89. Hufnagel JC, Hofmann T. 2008b. Quantitative reconstruction of the nonvolatile sensometabolome of a red wine. J. Agric. Food Chem. 56:9190-99
90. Ishikawa T, Noble AC. 1995. Temporal perception of astringency and sweetness in red wine. Food Qual. Pref. 6:27-33
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
92. J öbstl E, O'Connell J, Fairclough JPA, Williamson MP. 2004. Molecular model for astringency produced by polyphenol/protein interactions. Biomacromolecules 5:942-49
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
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
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
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
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
98. Kelebek H, Canbas A, Selli A, Saucier C, JourdesM, 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
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
100. Kong JM, Chia LS, Goh NK, Chia TF, Brouillard R. 2003. Analysis and biological activities of anthocyanins. Phytochemistry 64:923-33
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
102. Laurie VF, Waterhouse AL. 2006a. Glyceraldehyde bridging between flavanols and malvidin-3-glucoside in model solutions. J. Agric. Food Chem. 54:9105-11
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
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
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
106. Le Bourvellec C, Renard CM. 2012. Interactions between polyphenols and macromolecules: Quantification methods and mechanisms. Crit. Rev. Food Sci. Nutr. 52:213-48
107. Lee J, Kennedy JA, Devlin C, RedheadM, RennakerC. 2008. Effect of early seed removal during fermentation on proanthocyanidin extraction in red wine: A commercial production example. Food Chem. 107:1270-73
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
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
110. Macheix JJ, Fleuriet A, Billot J. 1990. Fruit Phenolics. Boca Raton, FL: CRC Press. 378 p.p.
111. Manfra M, DeNiscoM, BologneseA, 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
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
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
114. McManus JP, Davis KG, Lilley TH, Haslam E. 1981. The association of proteins with polyphenols. JCS Chem. Commun. 1981:309-11
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
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
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
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
119. Meyer J, Herńandez R. 1970. Seed tannin extraction in Cabernet Sauvignon. Am. J. Enol. Vitic. 21:184-88
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
121. Monagas M, Bartoloḿe B, Gómez-Cordovés C. 2005. Updated knowledge about the presence of phenolic compounds in wine. Crit. Rev. Food Sci. Nutr. 45:85-118
122. Monagas M, Gómez-Cordovés C, Bartoloḿe 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
123. Monagas M, Gómez-Cordovés C, Bartoloḿe 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
124. Morata A, Gómez-Cordovés C, Colomo B, Súarez 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
125. Morel-SalmiC, 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
126. Moskowitz AH, Hrazdina G. 1981. Vacuolar contents of fruit subepidermal cells from Vitis species. Plant Physiol. 68:686-92
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
128. Niketic-Aleksic G, Hrazdina G. 1972. Quantitative analysis of the anthocyanin content in grape juices and wines. Lebensm. Wiss. Technol. 5:163-65
129. Noble AC. 1994. Bitterness in wine. Physiol. Behav. 56:1251-55
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
131. Oliveira J, De Freitas V, Mateus N. 2009. A novel synthetic pathway to Vitisin B compounds. Tetrahedron Lett. 50:3933-35
132. Ough CS, Amerine MA. 1960. Experiments with controlled fermentations. IV. Red wines. Am. J. Enol. Vitic. 11:5-14
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
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
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
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
137. Pérez-Magaríno S. Gonźalez-San José M.L. 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
138. Peynaud É . 1984. Knowing and Making Wine. Transl. A Spenser. New York: Wiley-Intersci. 416 pp. (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
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
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
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
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
144. Poncet-Legrand C, Gautier C, Cheynier V, Imberty A. 2007. Interactions between flavan-3-ols and poly (Lproline) studied by isothermal titration calorimetry: Effect of the tannin structure. J. Agric. Food Chem. 55:9235-40
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
146. Prieur C, Rigaud J, Cheynier V, Moutounet M. 1994. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36:781-84
147. Puertas B, Guerrero RF, JuradoMS, JimenezMJ, Cantos-Villar E. 2008. Evaluation of alternative winemaking processes for red wine color enhancement. Food Sci. Technol. Int. 14:21-28
148. Remy S, FulcrandH, 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
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
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
151. Ribéreau-Gayon P, Dubourdieu D, Donèche B, Lonvaud A. 1998. Traité d'Oenologie. 1. Microbiologie du Vin Vinifications. Paris: Ed. Dunod. 661 p.p.
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
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
154. Robichaud JL, Noble AC. 1990. Astringency and bitterness of selected phenolics in wine. J. Sci. Food Agric. 53:343-53
155. Romero-Cascales I, Ferńandez-Ferńandez JI, Ĺ opez-Roca JM, Gómez-Plaza E. 2005. Themaceration process duringwinemaking extraction of anthocyanins from grape skins intowine. Eur. Food Res. Technol. 221:163-67
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
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
158. Śaenz-NavajasMP, Ferreira V, Dizy M, Ferńandez-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
159. Salas E, Dué nasM, 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
160. Salas E, FulcrandH, Meudec E, Cheynier V. 2003. Reactions of anthocyanins and tannins in model solutions. J. Agric. Food Chem. 51:7951-61
161. SchwarzM, 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
162. Scollary GR, Ṕasti G, Ḱallay M, Blackman J, Clark AC. 2012. Astringency response of red wines: Potential role of molecular assembly. Trends Food Sci. Tech. 27:25-36
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
164. Singleton VL. 1992. Tannins and the qualities of wines. In Plant Polyphenols: Synthesis, Properties, Significance, ed. RWHemingway, pp. 859-80. New York: Plenum. 1077 p.p.
165. Singleton VL, Draper DE. 1964. The transfer of polyphenolic compounds from grape seeds into wines. Am. J. Enol. Vitic. 15:34-40
166. Singleton VL, Noble AC. 1976. Wine flavor and phenolic substances. In Phenolic, Sulfur and Nitrogen Compounds in Food Flavors, ed. G Charalambous, I Katz, pp. 47-70. ACS Symp. Ser. 26. Washington, DC: Am. Chem. Soc. 215 p.p.
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
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
169. Somers TC. 1971. The polymeric nature of wine pigments. Phytochemistry 10:2175-86
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
171. Somers TC, Evans ME. 1979. Grape pigment phenomena: Interpretation of major colour losses during vinification. J. Sci. Food Agric. 30:623-33
172. Souquet JM, Cheynier V, Brossaud F, Moutounet M. 1996. Polymeric proanthocyanidins from grape skins. Phytochemisty 43:509-12
173. Spranger I, Cĺimaco 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
174. Su CT, Singleton VL. 1969. Identification of three flavan-3-ols from grapes. Phytochemisty 8:1553-58
175. Sun BS, de Śa MC, Leandro C, Caldeira I, Duarte FL, Spranger I. 2013. Reactivity of polymeric proanthocyanidins toward salivary proteins. J. Agric. Food Chem. 61:939-46
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
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
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
179. Valentov́a H, Skrov́akov́a S, Panovsḱa Z, Pokorny J. 2002. Time intensity studies of astringent taste. Food Chem. 78:29-37
180. Vasserot Y, Caillet S, Maujean A. 1997. Study of anthocyanin adsorption by yeast lees. Effect of some physicochemical parameters. Am. J. Enol. Vitic. 48:433-37
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
182. Vidal S, Francis L, NobleAC, Kwiatkowski M, Cheynier V, Waters EJ. 2004a.Taste andmouth-feel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal. Chim. Acta 513:57-65
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
184. Vrhovsek U, Vanzo A, Nemanic J. 2002. Effect of redwinemaceration techniques on oligomeric and polymeric proanthocyanidins in wine, cv. Blaufrankisch. Vitis 41:47-51
185. Wang H, Race EJ, Shrikhande AJ. 2003. Anthocyanin transformation in Cabernet Sauvignon wine during aging. J. Agric. Food Chem. 51:7989-94
186. Waterhouse AL. 2002. Wine phenolics. Ann. N.Y. Acad. Sci. 957:21-36
187. Waterhouse AL, Laurie VF. 2006. Oxidation of wine phenolics: A critical evaluation and hypotheses. Am. J. Enol. Vitic. 57:306-13
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
189. Wollmann N, Hofmann T. 2013. Compositional and sensory characterization of red wine polymers. J. Agric. Food Chem. 61:2045-61
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
191. Yaminishi T. 1990. Bitter compounds in tea. In Bitterness in Foods and Beverages, ed. RL Rouseff, pp. 159-67. Amsterdam: Elsevier. 356 p.p.
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
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
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
195. Adams DO, Harbertson JF, Picciotto EA. 2004. Fractionation of red wine polymeric pigments by protein precipitation and bisulfite bleaching. In Red Wine Colour: Revealing the Mysteries, ed. AL Waterhouse, JA Kennedy, pp. 275-88. Washington, DC: Am. Chem. Soc. 314 p.p.
196. Adams DO, Scholz RC. 2008. Tannins-The problem of extraction. In Proc. 13th Aust. Wine Ind. Tech. Conf., Aust. Soc. Vitic. Oenology, Adelaide, Aust., pp. 160-64
197. Alcalde-Éon C, Escribano-Bail ón 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
198. Alcalde-Éon 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
199. Amrani-Joutei K, Glories Y, Mercier M. 1994. Localization of tannins in grape berry skins. Vitis 33:133-38
200. Andersen OM, Jordheim M. 2006. The anthocyanins. In Flavonoids: Chemistry, Biochemistry and Applications, ed. M Andersen, KR Markham, pp. 452-71. Boca Raton, FL: CRC Press. 1256 p.p.
201. 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
202. Asenstorfer RE, Iland PG, Tate ME, Jones GP. 2003. Charge equilibria and pKa of malvidin-3-glucoside by electrophoresis. Anal. Biochem. 318:291-99
203. Bajec MR, Pickering G. 2008. Astringency: Mechanisms and perception. Crit. Rev. Food Sci. Nutr. 48:858-75
204. 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
205. 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
206. Bate-Smith E. 1973. Haemanalysis: The concept of relative astringency. Phytochemistry 12:907-12
207. 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
208. Bennick A. 2002. Interaction of plant polyphenol with salivary proteins. Crit. Rev. Oral Biol. Med. 13:184-96
209. 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
210. 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
211. 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
212. 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
213. 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
214. 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
215. 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
216. Boulton RB, Singleton VL, Bisson LF, Kunkee RE. 1996. Principles and Practices of Winemaking. New York: Chapman & Hall. 604 p.p.
217. Breslin PA, GilmoreM, Beauchamp GK, Green BG. 1993. Psychological evidence that astringency is a tactile sensation. Chem. Senses 18:273-84
218. 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
219. Busse-Valverde N, Bautista-Ort́in AB, Gómez-Plaza E, Ferńandez-Ferńandez JI, Gil-Mu ? noz R. 2012. Influence of skin maceration time on the proanthocyanidin content of red wines. Eur. Food Res. Technol. 235:1117-23
220. Cai Y, Gaffney SH, Lilley TH, Haslam E. 1989. Carbohydrate-polyphenol complexation. In Chemistry and Significance of Condensed Tannins, ed. RW Hemingway, JJ Karchesy, SJ Braham, pp. 307-22. New York: Plenum. 553 p.p.
221. 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
222. 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
223. Casassa LF, Larsen RC, Beaver CW, Mireles MS, KellerM, 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
224. 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
225. Castillo-Münoz N, Gómez-Alonso S, Garćia-Romero E, Gómez MV, Velders AH, Hermośin-Gutiérrez I. 2009. Flavonol 3-O-glycosides series of Vitis vinifera cv. Petit verdot red wine grapes. J. Agric. Food Chem. 57:209-19
226. Castillo-Münoz N, Gómez-Alonso S, Garćia-Romero E, Hermośin-Gutiérrez I. 2007. Flavonol profiles of Vitis Vinifera L. red grapes and their single-cultivar wines. J. Agric. Food Chem. 55:992-1002
227. Cerpa-Calder ón FK, Kennedy JA. 2008. Berry integrity and extraction of skin and seed proanthocyanidins during red wine fermentation. J. Agric. Food Chem. 56:9006-14
228. Charlton AJ, Baxter NJ, LilleyTH, 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
229. 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
230. Cheynier V. 2006. Flavonoids in wine. In Flavonoids: Chemistry, Biochemistry, and Applications, ed.MAndersen, KR Markham, pp. 443-70. Boca Raton, FL: CRC Press. 1256 p.p.
231. Cheynier V, Dué nas-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
232. Cheynier V, Prieur C, Guyot S, Rigaud J, Moutounet M. 1997. The structures of tannins in grapes and wines and their interactions with proteins. In Wine: Nutritional and Therapeutic Benefits, ed. TR Watkins, pp. 81-93. Washington, DC: ACS Symp. Ser. 296 p.p.
233. 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
234. 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 Bordeauxwine grapes (Cabernet Sauvignon and Merlot) for two consecutive vintages (2006 and 2007). J. Agric. Food Chem. 57:545-53
235. 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
236. 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
237. 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
238. Danilewicz JC. 2003. Review of reactionmechanisms of oxygen and proposed intermediate reduction products in wine: Central role of iron and copper. Am. J. Enol. Vitic. 54:73-85
239. 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
240. De Freitas VA, Carvalho E, Mateus N. 2003. Study of carbohydrate influence on protein-Tannin aggregation by nephelometry. Food Chem. 81:503-9
241. De Freitas VA, Mateus N. 2001. Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 49:940-45
242. 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
243. 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 winesimulated macerations. Eur. Food Res. Technol. 226:337-44
244. 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
245. 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
246. 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
247. 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
248. Dué nas M, Fulcrand H, Cheynier V. 2006. Formation of anthocyanin-flavanol adducts in model solutions. Anal. Chim. Acta 563:15-25
249. 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
250. Escribano-Bail ón MT, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C. 1995. Proanthocyanidins in skins from different grape varieties. Z. Lebensm. Unters. Forsch. 200:221-24
251. 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
252. Es-Safi NE, FulcrandH, CheynierV, 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. 47:2096-2102
253. 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
254. Flamini R, Traldi P. 2010. Mass Spectrometry in Grape and Wine Chemistry. Hoboken, NJ: Wiley. 348 pp
255. ulcrand 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
256. 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
257. 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
258. Gawel R. 1998. Red wine astringency: A review. Aust. J. Grape Wine Res. 4:74-95
259. Gil M, Kontoudakis N, Gonźalez 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
260. Gil-Mu ? noz R, Gómez-Plaza E, Mart́inez A, Ĺ opez-Roca JM. 1999. Evolution of phenolic compounds during wine fermentation and post-fermentation: Influence of grape temperature. J. Food Comp. Anal. 12:259-72
261. Glories Y, Saucier C. 2000. Tannin evolution from grape to wine. Effects on wine taste. In The ASEV 50th Anniv. Annu. Meet., ed. J Ratz, pp. 353-55. Davis, CA: Am. Soc. Enol. Vitic
262. Gómez-ḾiguezM, 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
263. Ǵomez-Plaza E, Romero-Cascales I, Ferńandez- Ferńandez JI, Ĺ opez-Roca JM. 2005. Themaceration process during winemaking extraction of anthocyanins from grape skins into wine. Eur. Food Res. Tech. 221:163-67
264. Gonźalez-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
265. Gonzalez-Manzano S, Santos-Buelga C, Pérez-Alonso JJ, Rivas-Gonzalo JC, Escribano-Bail ón 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
266. Gonźalez-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
267. Guerrero RF, Liazid A, PalmaM, Puertas B, Gonźalez-Barrio R, et al. 2009. Phenolic characterization of red grapes autochthonous to Andalusia. Food Chem. 112:949-55
268. 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
269. Hanlin RL, KelmMA, 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
270. 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
271. Harbertson JF, Mireles M, Harwood E, Weller KM, Ross CF. 2009. Chemical and sensory effects of saigńee, water addition and extended maceration on high Brix must. Am. J. Enol. Vitic. 60:450-60
272. Harbertson JF, Spayd S. 2006. Measuring phenolics in the winery. Am. J. Enol. Vitic. 57:280-88
273. Haslam E. 1982. Proanthocyanidins. In The Flavonoids: Advances in Research, ed. JB Harborne, TJ Mabry, pp. 417-47. London: Chapman & Hall. 744 p.p.
274. Haslam E. 1998. Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action. Cambridge, UK: Cambridge Univ. Press. 438 p.p.
275. 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
276. He F, He JJ, PanQH, 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
277. 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
278. Hermośin-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
279. Herńandez-Jiḿenez A, Kennedy JA, Bautista-Ort́in AB, Gómez-Plaza E. 2012. Effect of ethanol on grape seed proanthocyanidin extraction. Am. J. Enol. Vitic. 63:57-61
280. Hilgard EW. 1887. The extraction of color and tannin during red-wine fermentations. Univ. Calif. Agric. Exp. Stn. Bull. 77
281. Hufnagel JC, Hofmann T. 2008a.Orosensory directed identification of astringentmouthfeel and bitter-Tasting compounds in red wine. J. Agric. Food Chem. 56:1376-86
282. Hufnagel JC, Hofmann T. 2008b. Quantitative reconstruction of the nonvolatile sensometabolome of a red wine. J. Agric. Food Chem. 56:9190-99
283. Ishikawa T, Noble AC. 1995. Temporal perception of astringency and sweetness in red wine. Food Qual. Pref. 6:27-33
284. 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
285. J öbstl E, O'Connell J, Fairclough JPA, Williamson MP. 2004. Molecular model for astringency produced by polyphenol/protein interactions. Biomacromolecules 5:942-49
286. Jurd L. 1969. Review of polyphenol condensation reactions and their possible occurrence in the aging of wines. Am. J. Enol. Vitic. 20:191-95
287. 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
288. Kallithraka S, Bakker J, Clifford MN. 1997b. Effect of pH on astringency in model solutions and wines. J. Agric. Food Chem. 45:2211-16
289. 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
290. Kantz K, Singleton VL. 1991. Isolation and determination of polymeric polyphenols in wines using Sephadex LH-20. Am. J. Enol. Vitic. 42:309-16
291. Kelebek H, Canbas A, Selli A, Saucier C, JourdesM, 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
292. 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
293. Kong JM, Chia LS, Goh NK, Chia TF, Brouillard R. 2003. Analysis and biological activities of anthocyanins. Phytochemistry 64:923-33
294. 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
295. Laurie VF, Waterhouse AL. 2006a. Glyceraldehyde bridging between flavanols and malvidin-3-glucoside in model solutions. J. Agric. Food Chem. 54:9105-11
296. 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
297. 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
298. 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
299. Le Bourvellec C, Renard CM. 2012. Interactions between polyphenols and macromolecules: Quantification methods and mechanisms. Crit. Rev. Food Sci. Nutr. 52:213-48
300. Lee J, Kennedy JA, Devlin C, RedheadM, RennakerC. 2008. Effect of early seed removal during fermentation on proanthocyanidin extraction in red wine: A commercial production example. Food Chem. 107:1270-73
301. 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
302. 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
303. Macheix JJ, Fleuriet A, Billot J. 1990. Fruit Phenolics. Boca Raton, FL: CRC Press. 378 p.p.
304. Manfra M, DeNiscoM, BologneseA, 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
305. 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
306. 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
307. McManus JP, Davis KG, Lilley TH, Haslam E. 1981. The association of proteins with polyphenols. JCS Chem. Commun. 1981:309-11
308. 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
309. 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
310. Medina K, Boido E, Dellacassa E, Carrau F. 2005. Yeast interactions with anthocyanins during red wine fermentation. Am. J. Enol. Vitic. 56:104-9
311. 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
312. Meyer J, Herńandez R. 1970. Seed tannin extraction in Cabernet Sauvignon. Am. J. Enol. Vitic. 21:184-88
313. 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
314. Monagas M, Bartoloḿe B, Gómez-Cordovés C. 2005. Updated knowledge about the presence of phenolic compounds in wine. Crit. Rev. Food Sci. Nutr. 45:85-118
315. Monagas M, Gómez-Cordovés C, Bartoloḿe 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
316. Monagas M, Gómez-Cordovés C, Bartoloḿe 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
317. Morata A, Gómez-Cordovés C, Colomo B, Súarez 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
318. Morel-SalmiC, 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
319. Moskowitz AH, Hrazdina G. 1981. Vacuolar contents of fruit subepidermal cells from Vitis species. Plant Physiol. 68:686-92
320. 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
321. Niketic-Aleksic G, Hrazdina G. 1972. Quantitative analysis of the anthocyanin content in grape juices and wines. Lebensm. Wiss. Technol. 5:163-65
322. Noble AC. 1994. Bitterness in wine. Physiol. Behav. 56:1251-55
323. 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
324. Oliveira J, De Freitas V, Mateus N. 2009. A novel synthetic pathway to Vitisin B compounds. Tetrahedron Lett. 50:3933-35
325. Ough CS, Amerine MA. 1960. Experiments with controlled fermentations. IV. Red wines. Am. J. Enol. Vitic. 11:5-14
326. 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
327. 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
328. 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
329. 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
330. Pérez-Magaríno S. Gonźalez-San José M.L. 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
331. Peynaud É . 1984. Knowing and Making Wine. Transl. A Spenser. New York: Wiley-Intersci. 416 pp. (In French
332. 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
333. 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
334. 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
335. 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
336. 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
337. Poncet-Legrand C, Gautier C, Cheynier V, Imberty A. 2007. Interactions between flavan-3-ols and poly (Lproline) studied by isothermal titration calorimetry: Effect of the tannin structure. J. Agric. Food Chem. 55:9235-40
338. 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
339. Prieur C, Rigaud J, Cheynier V, Moutounet M. 1994. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36:781-84
340. Puertas B, Guerrero RF, JuradoMS, JimenezMJ, Cantos-Villar E. 2008. Evaluation of alternative winemaking processes for red wine color enhancement. Food Sci. Technol. Int. 14:21-28
341. Remy S, FulcrandH, 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
342. 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
343. Rentzsch M, Schwarz M, Winterhalter P. 2007. Pyranoanthocyanins: An overview on structures, occurrence, and pathways of formation. Trends Food Sci. Tech. 18:526-34
344. Ribéreau-Gayon P, Dubourdieu D, Donèche B, Lonvaud A. 1998. Traité d'Oenologie. 1. Microbiologie du Vin Vinifications. Paris: Ed. Dunod. 661 p.p.
345. 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
346. 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
347. Robichaud JL, Noble AC. 1990. Astringency and bitterness of selected phenolics in wine. J. Sci. Food Agric. 53:343-53
348. Romero-Cascales I, Ferńandez-Ferńandez JI, Ĺ opez-Roca JM, Gómez-Plaza E. 2005. Themaceration process duringwinemaking extraction of anthocyanins from grape skins intowine. Eur. Food Res. Technol. 221:163-67
349. Rossi JA, Singleton VL. 1966. Flavor effects and adsorptive properties of purified fractions of grape-seed phenols. Am. J. Enol. Vitic. 17:240-46
350. 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
351. Śaenz-NavajasMP, Ferreira V, Dizy M, Ferńandez-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
352. Salas E, Dué nasM, 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
353. Salas E, FulcrandH, Meudec E, Cheynier V. 2003. Reactions of anthocyanins and tannins in model solutions. J. Agric. Food Chem. 51:7951-61
354. SchwarzM, 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
355. Scollary GR, Ṕasti G, Ḱallay M, Blackman J, Clark AC. 2012. Astringency response of red wines: Potential role of molecular assembly. Trends Food Sci. Tech. 27:25-36
356. Scudamore-Smith PD, Hooper RL, McLaren ED. 1990. Color and phenolic changes of Cabernet Sauvignon wine made by simultaneous yeast/bacteria
357. Singleton VL. 1992. Tannins and the qualities of wines. In Plant Polyphenols: Synthesis, Properties, Significance, ed. RWHemingway, pp. 859-80. New York: Plenum. 1077 p.p.
358. Singleton VL, Draper DE. 1964. The transfer of polyphenolic compounds from grape seeds into wines. Am. J. Enol. Vitic. 15:34-40
359. Singleton VL, Noble AC. 1976. Wine flavor and phenolic substances. In Phenolic, Sulfur and Nitrogen Compounds in Food Flavors, ed. G Charalambous, I Katz, pp. 47-70. ACS Symp. Ser. 26. Washington, DC: Am. Chem. Soc. 215 p.p.
360. 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
361. 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
362. Somers TC. 1971. The polymeric nature of wine pigments. Phytochemistry 10:2175-86
363. 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
364. Somers TC, Evans ME. 1979. Grape pigment phenomena: Interpretation of major colour losses during vinification. J. Sci. Food Agric. 30:623-33
365. Souquet JM, Cheynier V, Brossaud F, Moutounet M. 1996. Polymeric proanthocyanidins from grape skins. Phytochemisty 43:509-12
366. Spranger I, Cĺimaco 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
367. Su CT, Singleton VL. 1969. Identification of three flavan-3-ols from grapes. Phytochemisty 8:1553-58
368. Sun BS, de Śa MC, Leandro C, Caldeira I, Duarte FL, Spranger I. 2013. Reactivity of polymeric proanthocyanidins toward salivary proteins. J. Agric. Food Chem. 61:939-46
369. 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
370. Thorngate JH, Noble AC. 1995. Sensory evaluation of bitterness and astringency of 3R-epicatechin and 3S(+)-catechin. J. Sci. Food Agric. 67:531-35
371. 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
372. Valentov́a H, Skrov́akov́a S, Panovsḱa Z, Pokorny J. 2002. Time intensity studies of astringent taste. Food Chem. 78:29-37
373. Vasserot Y, Caillet S, Maujean A. 1997. Study of anthocyanin adsorption by yeast lees. Effect of some physicochemical parameters. Am. J. Enol. Vitic. 48:433-37
374. 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
375. Vidal S, Francis L, NobleAC, Kwiatkowski M, Cheynier V, Waters EJ. 2004a.Taste andmouth-feel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal. Chim. Acta 513:57-65
376. 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
377. Vrhovsek U, Vanzo A, Nemanic J. 2002. Effect of redwinemaceration techniques on oligomeric and polymeric proanthocyanidins in wine, cv. Blaufrankisch. Vitis 41:47-51
378. Wang H, Race EJ, Shrikhande AJ. 2003. Anthocyanin transformation in Cabernet Sauvignon wine during aging. J. Agric. Food Chem. 51:7989-94
379. Waterhouse AL. 2002. Wine phenolics. Ann. N.Y. Acad. Sci. 957:21-36
380. Waterhouse AL, Laurie VF. 2006. Oxidation of wine phenolics: A critical evaluation and hypotheses. Am. J. Enol. Vitic. 57:306-13
381. 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
382. Wollmann N, Hofmann T. 2013. Compositional and sensory characterization of red wine polymers. J. Agric. Food Chem. 61:2045-61
383. 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
384. Yaminishi T. 1990. Bitter compounds in tea. In Bitterness in Foods and Beverages, ed. RL Rouseff, pp. 159-67. Amsterdam: Elsevier. 356 p.p.
385. 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
386. 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
387. 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