Abstract
The occurrence of tannins and anthocyanins from grapes and wines is well documented. Various chemical reactions involving anthocyanins and/or flavanols have been demonstrated to occur during red wine aging. Current knowledge regarding the reaction mechanisms involved in some of these processes and the structures of the resulting products is reviewed. Their effects on wine organoleptic quality are also discussed.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Teissedre P-L (2008) Oxygen and phenolic compounds: from the barrel to the chips (Oxygène et composés phénoliques: De la barrique aux copeaux). Biofutur 294:40–43
Bamforth CW (1999) Beer haze. J Am Soc Brew Chem 57:81–90
Carando S, Teissedre P-L, Pascual-Martinez L, Cabanis J-C (1999) Levels of flavan-3-ols in French wines. J Agric Food Chem 47:4161–4166
Landrault N, Poucheret P, Ravel P, Gasc F, Cros G, Teissedre P-L (2001) Antioxidant capacities and phenolics levels of French wines from different varieties and vintages. J Agric Food Chem 49:3341–3348
Chira K, Suh J-H, Saucier C, Teissedre P-L (2008) Grape phenolics (Les polyphénols du raisin). Phytotherapie 6:75–82
Burns J, Mullen W, Landrault N, Teissedre P-L, Lean MEJ, Crozier A (2002) Variations in the profile and content of anthocyanins in wines made from Cabernet Sauvignon and hybrid grapes. J Agric Food Chem 50:4096–4102
Teissedre PL, Chervin C (2011) Grapes, chapter 9. In: Terry LA (ed) Health-promoting properties of fruits and vegetables. CABI, Wallingford, Oxfordshire; Cambridge, MA, pp 154–170
Bourzeix M, Weyland E, Heredia N (1986) Etudes des catechines et des procyanidols de la grappe de raisin, du vin et d’autres dérivés de la vigne. Bull OIV 59:1171–1254
Ribéreau-Gayon P (1959) Recherches sur les anthocyannes des végétaux. Application au genre Vitis. Librairie Generale de l’Enseignement, Paris, France
Ribéreau-Gayon P (1964) Les composés phénoliques du raisin et du vin.II. Les flavonosides et les anthocyanosides. Ann Physiol Vég 6:211–242
Waterhouse AL, Teissedre P-L (1997) Levels of phenolics in California varietal wines. ACS Symposium Series 661:12–23
Chira K, Lorrain B, Ky I, Teissedre P-L (2011) Tannin composition of cabernet-sauvignon and merlot grapes from the bordeaux area for different vintages (2006 to 2009) and comparison to tannin profile of five 2009 vintage mediterranean grapes varieties. Molecules 16:1519–1532
Ritchey JG, Waterhouse AL (1999) A standard red wine: monomeric phenolic analysis of commercial Cabernet Sauvignon wines. Am J Enol Vitic 50:91–100
Robichaud JL, Noble AC (1990) Astringency and bitterness of selected phenolics in wine. J Sci Food Agric 53:343–353
Bravo L (1998) Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutr Rev 56:317–333
Bombardelli E, Morazzoni P (1995) Vitis vinifera L. Fitoterapia 66:291–317
Ricardo da Silva JM, Rigaud J, Cheynier V, Cheminat A, Moutounet M (1991) Procyanidin dimers and trimers from grape seeds. Phytochemistry 30:1259–1264
Brouillard R (1982) Chemical structure of anthocyanins. In: Markakis P (ed) Anthocyanins as food colors. Academic, New York
Francis FJ (1989) Food colorants: anthocyanins. Crit Rev Food Sci Nutr 28:273–314
Holt E, Francis IL, Field J, Hererich PG, Iland PG (2008) Relationships between wine phenolic composition and wine sensory properties for Cabernet Sauvignon (Vitis vinifera L.). Aust J Grape Wine Res 14:162–176
Ristic R, Downey MO, Iland PG, Bindon K, Francis IL, Herderich M, Robinson SP (2007) Exclusion of sunlight from Shiraz grapes alters wine colour, tannin and sensory properties. Aust J Grape Wine Res 13:53–65
Cheynier V, Dueñas-Paton M, Salas E, Maury C, Souquet JM, Sarni-Manchado P, Fulcrand H (2006) Structure and properties of wine pigments and tannins. Am J Enol Vitic 57:298–305
Gambuti A, Strollo D, Erbaggio A, Lecce L, Moio L (2007) Effect of winemaking practices on color indexes and selected bioactive phenolics of Aglianico wine. J Food Sci 72:S623–S627
Haslam E (1998) Taste, bitterness and astringency. In: Haslam E (ed) Practical polyphenolics: from structure to molecular recognition and physiological action. Cambridge University Press, Cambridge
Gawel R (1998) Red wine astringency: a review. Aust J Grape Wine Res 4:74–95
Noble AC (1994) Bitterness in wine. Physiol Behav 6:1251–1255
Kallithraka S, Bakker J, Clifford MN (1997) Evaluation of bitterness and astringency of (+)-catechin and (−)-epicatechin in red wine and in model solution. J Sens Stud 12:25–37
Arnold RA, Noble AC, Singleton VL (1980) Bitterness and astringency of phenolic fractions in wine. J Agric Food Chem 28:675–678
Fontoin H, Saucier C, Teissedre P-L, Glories Y (2008) Effect of pH, ethanol and acidity on astringency and bitterness of grape seed tannin oligomers in model wine solution. Food Qual Pref 19:286–291
Ishikawa T, Noble AC (1995) Temporal perception of astringency and sweetness in red wine. Food Qual Pref 6:27–33
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 57:545–553
Chira K, Pacella N, Jourdes M, Teissedre P-L (2011) Chemical and sensory evaluation of Bordeaux wines (Cabernet-Sauvignon and Merlot) and correlation with wine age. Food Chem 126:1971–1977
Lorrain B, Chira K, Teissedre P-L (2011) Phenolic composition of Merlot and Cabernet-Sauvignon grapes from Bordeaux vineyard for the 2009-vintage: comparison to 2006, 2007 and 2008 vintages. Food Chem 126:1991–1999
Fernández K, Kennedy JA, Agosin A (2007) Characterization of grape and wine proanthocyanidins of Vitis vinifera cv. Carmenere. J Agric Food Chem 55:3675–3680
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–335s
Vidal S, Courcoux P, Francis L, Kwiatkowski M, Gawel R, Williams P, Waters EJ, Cheynier V (2004) Use of an experimental design approach for evaluation of key wine components on mouth-feel perception. Food Qual Pref 15(209):217
Vidal S, Francis L, Guyot S, Marnet N, Kwiatkowski M, Gawel R, Cheynier V, Waters EJ (2003) The mouth-feel properties of grape and apple proanthocyanidins in a winelike medium. J Sci Food Agric 83:564–573
Gawel R, Oberholster A, Francis IL (2000) A mouth-feel wheel: terminology for communicating the mouth-feel characteristics of red wine. Aust J GrapeWine Res 6:203–207
Gawel R, Iland PG, Francis IL (2001) Characterizing the astringency of red wine: a case study. Food Qual Pref 12:83–94
Cheynier V, Fulcrand H, Brossaud F, Asselin C, Moutounet M (1998) Phenolic composition as related to red wine flavor. In: Waterhouse AL, Ebeler SE (eds) Chemistry of wine flavor. Oxford University Publishing, New York
Fischer U, Noble AC (1994) The effect of ethanol, catechin concentration and pH on sourness and bitterness of wine. Am J Enol Vitic 45:6–10
Peleg H, Bodine KK, Noble AC (1998) The influence of acid on astringency of alum and phenolic compounds. Chem Senses 23:371–378
Smith AK, June H, Noble AC (1996) Effects of viscosity on the bitterness and astringency of grape seed tannin. Food Qual Pref 7:161–166
Boselli E, Boulton RB, Thorngate JH, Frega NG (2004) Chemical and sensory characterization of DOC red wines from Marche (Italy) related to vintage and grape cultivars. J Agric Food Chem 52:3843–3854
Vidal S, Courcoux P, Francis L, Williams P, Kwiatkowski M, Gawel R, Cheynier V, Waters EJ (2004) The mouth-feel properties of polysaccharides and anthocyanins in a wine like medium. Food Chem 85:519–525
Riou V, Vernhet A, Doco T, Moutounet M (2001) Aggregation of grape seed tannins in model wine-effect of wine polysaccharides. Food Hydrocolloids 16:17–23
De Freitas V, Carvalho E, Mateus N (2003) Study of carbohydrate influence on protein tannin aggregation by nephelometry. Food Chem 81:503–509
Saucier C, Guerra C, Laguerre M, Glories Y (1997) (+)-catechin-acetaldehyde condensation products in relation with wine-ageing. Phytochemistry 46:229–234
Saucier C, Bourgeois G, Vitry C, Roux D, Glories Y (1997) Characterization of (+)-catechin-acetaldehyde polymers: a model for colloidal state of wine polyphenols. J Agric Food Chem 45:1045–1049
Vidal S, Leigh F, Noble AC, Kwiatkowski M, Cheynier V, Waters EJ (2004) Taste and mouth-feel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal Chim Acta 513:57–65
Villamor RR, Harbertson JF, Ross CF (2009) Influence of tannin concentration, storage temperature, and time on chemical and sensory properties of Cabernet Sauvignon and Merlot wines. Am J Enol Vitic 60:442–449
Gawel R, Leigh F, Waters EJ (2007) Statistical correlations between the in-mouth textural characteristics and the chemical composition of shiraz wines. J Agric Food Chem 55:2683–2687
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
Waterhouse AL (2002) Wine phenolics. Ann N Y Acad Sci 957:21–36
Drinkine J, Lopes P, Kennedy JA, Teissedre P-L, Saucier C (2007) Analysis of ethylidene-bridged flavan-3-ols in wine. J Agric Food Chem 55:1109–1116
Drinkine J, Lopes P, Kennedy JA, Teissedre P-L, Saucier C (2007) Ethylidene-bridged flavan-3-ols in red wine and correlation with wine age. J Agric Food Chem 55:6292–6299
Picinelli A, Bakker JPB (1994) Model wine solutions: effect of sulphur dioxide on colour and composition during aging. Vitis 33:31–35
Guerra C (1997) Recherches sur les interactions anthocyanes-flavanols: application à l’interprétation chimique de la couleur des vins rouges. Université de Bordeaux II, Bordeaux, France
Saucier C, Guerra C, Pianet I, Laguerre M, Glories Y (1997) (+)-Catechin acetaldehyde condensation products in relation to wine-ageing. Phytochemistry 46:229–234
Es-Safi NE, Fulcrand H, Cheynier V, Moutounet M (1999) Competition between (+)-catechin and (−)-epicatechin in acetaldehyde-induced polymerization of flavanols. J Agric Food Chem 47:2088–2095
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 47:2096–2102
Francia-Aricha EM, Guerra MT, Rivas-Gonzalo JC, Santos-Buelga C (1997) New anthocyanin pigments formed after condensation with flavanols. J Agric Food Chem 45:2262–2266
Waterhouse AL, Laurie VF (2006) Oxidation of wine phenolics: a critical evaluation and hypotheses. Am J Enol Vitic 57:306–313
Singleton VL (1987) Oxygen with phenols and related reactions in musts, wines, and model systems: observations and practical implications. Am J Enol Vitic 38:69–77
Cutzach I, Chatonnet P, Dubourdieu D (2000) Influence of storage conditions on the formation of some volatile compounds in white fortified wines (vins doux naturels) during the aging process. J Agric Food Chem 48:2340–2345
Escudero A, Asensio E, Cacho J, Ferreira V (2002) Sensory and chemical changes of young white wines stored under oxygen. An assessment of the role played by aldehydes and some other important odorants. Food Chem 77:325–331
Rivas-Gonzalo J, Bravo-Haro S, Santos-Buelga C (1996) Detection of compounds formed through the reaction of malvidin 3-mono-glucoside and catechin in the presence of acetaldehyde. J Agric Food Chem 43:1444–1449
Escribano-Bailon T, Alvarez-Garcia M, Rivas-Gonzalo J, Heredia FJ, Santos-Buelga C (2001) Color and stability of pigments derived from the acetaldehyde-mediated condensation between malvidin 3-O-glucoside and (+)-catechin. J Agric Food Chem 49:1213–1217
Timberlake CF, Bridle P (1976) The effect of processing and other factors on the colour characteristics of some red wines. Vitis 15:37–49
Dallas C, Ricardo Da-Silva MJ, Laureano O (1996) Products formed in model wine solutions involving anthocyanins, procyanidin B2, and acetaldehyde. J Agric Food Chem 44:2402–2407
Bakker J, Picinelli A, Bridle P (1993) Model wine solutions: colour and composition changes during ageing. Vitis 32:111–118
Morata A, Calderon F, Gonzalez MC, Gomez-Cordoves MC, Suarez JA (2007) Formation of the highly stable pyranoanthocyanins (vitisins A and B) in red wines by the addition of pyruvic acid and acetaldehyde. Food Chem 100:1144–1152
Ribéreau-Gayon P, Pontallier P, Glories Y (1983) Some interpretations of colour changes in young red wines during their conservation. J Sci Food Agric 34:505–516
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
Vivar-Quintana AM, Santos-Buelga C, Rivas-Gonzalo JC (2002) Anthocyanin-derived pigments and colour of red wines. Anal Chim Acta 458:147–155
Mateus N, Carvalho E, Carvalho RFA, Melo A, Gonzales-Paramas MA, Santos-Buelga C, De Freitas APV (2003) Isolation and structural characterization of new acylated anthocyanin-vinyl-flavanol occurring in aging red wines. J Agric Food Chem 51:277–282
Mateus N, Oliveira J, Santos-Buelga C, Silva AMS, De Freitas APV (2004) NMR structure characterization of a new vinylpyranoanthocyanin-catechin pigment (a portisin). Tetrahedron Lett 45:3455–3457
He J, Santos Buelga C, Mateus N, De Freitas APV (2006) Isolation and quantification of oligomeric pyranoanthocyanin-flavanol pigments from red wines by combination of column chromatographic techniques. J Chromatogr A 1134:215–225
Andersen OM (2002) Anthocyanins. In: Encyclopedia of life sciences. MacMillan Publishers Ltd., London, p. 597–605
Devia B, Llabres G, Wouters J, Dupont L, Escribano-Bailon MT, de Pasccual-Teresa S, Angenot L, Tits M (2002) New 3-deoxyanthocyanidins from leaves of Arrabidaea chica. Phytochem Anal 13: 114–120
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this entry
Cite this entry
Teissedre, PL., Jourdes, M. (2013). Tannins and Anthocyanins of Wine: Phytochemistry and Organoleptic Properties. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_73
Download citation
DOI: https://doi.org/10.1007/978-3-642-22144-6_73
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-22143-9
Online ISBN: 978-3-642-22144-6
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics