Impact of Time, Oxygen and Different Anthocyanin to Tannin Ratios on the Precipitate and Extract Composition Using Liquid Chromatography-High Resolution Mass Spectrometry

  • G. Garrido-Bañuelos Department of Viticulture and Oenology, Stellenbosch University, Private Bag X1, Matieland 7062
  • A. Buica Department of Viticulture and Oenology, Stellenbosch University, Private Bag X1, Matieland 7062 http://orcid.org/0000-0003-4775-8399
  • A. de Villiers Department of Chemistry and Polymer Science, Stellenbosch University, Private Bag X1, Matieland 7062
  • W.J. du Toit Department of Viticulture and Oenology, Stellenbosch University, Private Bag X1, Matieland 7062

Abstract

Wine colour and phenolic stability over time are influenced by the amount and nature of phenolics in young wines. The ratio between different phenolic compounds can also be determinant in the colour and phenolic development of red wines. Three different anthocyanin to tannin ratios extracted in a wine-like system were saturated with oxygen several times during sample storage. A LC-HRMS method was used to evaluate the impact of a forced oxidation and of the different extracts on the wine-like composition and on the precipitate formed over time. The extract composition was found to be the most determinant factor for the precipitate formed. Time was also found to be a relevant factor according to the precipitate composition.

Downloads

Download data is not yet available.

Author Biography

A. Buica, Department of Viticulture and Oenology, Stellenbosch University, Private Bag X1, Matieland 7062

Researcher in Oenology

Depatrment of Viticulture and Oenology

References

Alberts, P., Stander, M.A., et al., 2012. Advanced ultra high pressure liquid chromatography – tandem mass spectrometric methods for the screening of red wine anthocyanins and derived pigments J. Chromatogr. A 1235, 92–102.

Arapitsas, P., Scholz, M., et al., 2012. A Metabolomic Approach to the Study of Wine Micro- Oxygenation PLoS One 7, 5, 1–11.

Arapitsas, P., Speri, G., et al., 2014. The influence of storage on the “‘chemical age’” of red wines Metabolomics 10, 816–832.

Arapitsas, P., Corte, A. Della, et al., 2016. Studying the effect of storage conditions on the metabolite content of red wine using HILIC LC-MS based metabolomics Food Chem. 197, 1331–1340.

Arnold, R.A. & Noble, A.C., 1978. Bitterness and astringency of grape seed phenolics in a model wine solution. Am. J. Enol. Vitic. 29, 3, 11–13.

Atanasova, V., Fulcrand, H., et al., 2002. Effect of oxygenation on polyphenol changes occurring in the course of wine-making Anal. Chim. Acta 458, 1, 15–27.

Bertrand, A. & Barbe, J.C., 2002. Formation of γ-gluconolactone in a wine-like model system J. Sci. Food Agric. 82, 13, 1571–1573.

Bimpilas, A., Tsimogiannis, D., et al., 2015. Evolution of phenolic compounds and metal content of wine during alcoholic fermentation and storage Food Chem. 178, 164–171.

Bindon, K.A., Smith, P.A., et al., 2010. Interaction between Grape-Derived Proanthocyanidins and Cell Wall Material . 1 . Effect on Proanthocyanidin Composition and Molecular Mass J. Agric. Food Chem. 58, 2520–2528.

Canals, R., Llaudy, C., et al., 2008. Influence of the elimination and addition of seeds on the colour , phenolic composition and astringency of red wine Am. J. Enol. Vitic. 226, 1183–1190.

Carrascón, V., Vallverdú-Queralt, A., et al., 2018. The kinetics of oxygen and SO2 consumption by red wines. What do they tell about oxidation mechanisms and about changes in wine composition? Food Chem. 241, 206–214.

Castellari, M., Matricardi, L., et al., 2000. Level of single bioactive phenolics in red wine as a function of the oxygen supplied during storage. Food Chem. 69, 61–67.

Cerpa-Calderón, F.K. & Kennedy, J.A., 2008. Berry integrity and extraction of skin and seed proanthocyanidins during red wine fermentation J. Agric. Food Chem. 56, 19, 9006–9014.

Dallas, C., Ricardo-da-Silva, J.M., et al., 1996. Interactions of Oligomeric Procyanidins in Model Wine Solutions Containing Malvidin-3-Glucoside and Acetaldehyde J. Sci. Food Agric. 70, 4, 493–500.

Danilewicz, J.C., 2007. Interaction of sulfur dioxide, polyphenols, and oxygen in a wine-model system: Central role of iron and copper Am. J. Enol. Vitic. 58, 1, 53–60.

Es-Safi, N.E., Fulcrand, H., et al., 1999. Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3-O-glucoside in a model solution system J. Agric. Food Chem. 47, 5, 2096–2102.

Fulcrand, H., Cameira dos Santos, P.-J., et al., 1996. Structure of new anthocyanin-derived wine pigments. J. Chem. Soc. 69, 60.

Garrido-Bañuelos, G., 2018. Factors influencing the colour and phenolic composition of Shiraz wine during winemaking. Stellenbosch University March.

González-Manzano, S., Rivas-Gonzalo, J.C., et al., 2004. Extraction of flavan-3-ols from grape seed and skin into wine using simulated maceration Anal. Chim. Acta 513, 283–289.

Guaita, M., Petrozziello, M., et al., 2017. Influence of early seeds removal on the physicochemical, polyphenolic, aromatic and sensory characteristics of red wines from Gaglioppo cv. Eur. Food Res. Technol. 243, 1311–1322.

He, F., Liang, N., et al., 2012. Anthocyanins and Their Variation in Red Wines I. Monomeric Anthocyanins and Their Color Expression Molecules 17, 1571–1601.

Hernández-Jiménez, A., Kennedy, J.A., et al., 2012. Effect of Ethanol on Grape Seed Proanthocyanidin Extraction Am. J. Enol. Vitic. 63, 57–61.

Jorgensen, E., Marin, A., et al., 2004. Analysis of the oxidative degradtion of proanthocyanidins under basic conditions J. Agric. Food Chem. 52, 2292–2296.

Lee, J., Kennedy, J.A., et al., 2008. Effect of early seed removal during fermentation on proanthocyanidin extraction in red wine : A commercial production example Food Chem. 107, 1270–1273.

Lucci, P., Saurina, J., et al., 2017. Trends in LC-MS and LC-HRMS analysis and characterization of polyphenols in food TrAC - Trends Anal. Chem. 88, 1–24.

Mattivi, F., Vrhovsek, U., et al., 2009. Differences in the amount and structure of extractable skin and seed tannins amongst red grape varieties Aust. J. Grape Wine Res. 15, 27–35.

McRae, J.M., Day, M.P., et al., 2015. Effect of early oxygen exposure on red wine colour and tannins Tetrahedron 71, 20, 3131–3137.

Meyer, B.J. & Hernandez, R., 1970. Seed Tannin Extraction in Cabernet Sauvignon. Am. J. Enol. Vitic. 21, 184–188.

Monagas, M., Bartolomé, B., et al., 2005. Updated knowledge about the presence of phenolic compounds in wine. Crit. Rev. Food Sci. Nutr. 45, 85–118.

Monagas, M., Gómez-Cordovés, C., et al., 2006. Evolution of the phenolic content of red wines from Vitis vinifera L . during ageing in bottle Food Chem. 95, 405–412.

Pascual, O., González-Royo, E., et al., 2016. Influence of Grape Seeds and Stems on Wine Composition and Astringency J. Agric. Food Chem. 64, 34, 6555–6566.

Peleg, H., Gacon, K., et al., 1999. Bitterness and astringency of flavan-3-ol monomers, dimers and trimers. J. Sci. Food Agric. 79, 8, 1123–1128.

Pérez-Magariño, S. & González-SanJosé, 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, 5, 1181–1189.

Peyrot Des Gachons, C. & Kennedy, J.A., 2003. Direct Method for Determining Seed and Skin Proanthocyanidin Extraction into Red Wine J. Sci. Food Agric. 51, 5877–5881.

Picariello, L., Gambuti, A., et al., 2017. Evolution of pigments, tannins and acetaldehyde during forced oxidation of red wine: Effect of tannins addition LWT - Food Sci. Technol. 77, 370–375.

Poncet-Legrand, C., Doco, T., et al., 2007. Inhibition of grape seed tannin aggregation by wine mannoproteins: Effect of polysaccharide molecular weight Am. J. Enol. Vitic. 58, 1, 87–91.

Prakash, S., Iturmendi, N., et al., 2016. Quantitative analysis of Bordeaux red wine precipitates by solid-state NMR : Role of tartrates and polyphenols Food Chem. 199, 229–237.

Quaglieri, C., Jourdes, M., et al., 2017. Updated knowledge about pyranoanthocyanins: Impact of oxygen on their contents, and contribution in the winemaking process to overall wine color Trends Food Sci. Technol. 67, July, 139–149.

Raposo, R., Ruiz-Moreno, M.J., et al., 2016. Effect of hydroxytyrosol on quality of sulfur dioxide-free red wine Food Chem. 192, 25–33.

Ribéreau-Gayon, P., Glories, Y., et al., 2006. Handbook of Enology. Volume 2. The chemistry of wine. Stabilization and treatments. John Wiley & Sons, LTD.

De Rosso, M., Panighel, A., et al., 2015. Characterization of non-anthocyanic flavonoids in some hybrid red grape extracts potentially interesting for industrial uses Molecules 20, 10, 18095–18106.

Sacchi, K.L., Bisson, L.F., et al., 2005. A review of the effect of winemaking techniques on phenolic extraction in red wines Am. J. Enol. Vitic. 56, 3, 197–206.

Saucier, C., Bourgeois, G., et al., 1997. Characterization of (+)-Catechin−Acetaldehyde Polymers: A Model for Colloidal State of Wine Polyphenols J. Agric. Food Chem. 45, 4, 1045–1049.

Singleton, V.L. & Trousdale, E.K., 1992. Anthocyanin-Tannin Interactions Explaining differences in polymeric phenols between white and red wines. Am. J. Enol. Vitic. 43, 63–70.

Smith, P.A., McRae, J.M., et al., 2015. Impact of winemaking practices on the concentration and composition of tannins in red wine Aust. J. Grape Wine Res. 21, 601–614.

Sparrow, A.M., Dambergs, R.G., et al., 2015. Interaction of Grape Skin , Seed , and Pulp Tissues on Tannin and Anthocyanin Extraction in Pinot noir Wines Am. J. Enol. Vitic. 1–27.

Springer, L.F., Chen, L.A., et al., 2016. Relationship of Soluble Grape-Derived Proteins to Condensed Tannin Extractability during Red Wine Fermentation J. Agric. Food Chem. 64, 43, 8191–8199.

Timberlake, C.F. & Bridle, P., 1977. Anthocyanins : Colour Augmentation with Catechin and Acetaldehyde. J. Sci. Food Agric. 28, 539–544.

Du Toit, W.J., Marais, J., et al., 2006. Oxygen in must and wine: A review South African J. Enol. Vitic. 27, 1, 76–94.

Vallverdú-Queralt, A., Meudec, E., et al., 2017. The Hidden Face of Wine Polyphenol Polymerization Highlighted by High-Resolution Mass Spectrometry ChemistryOpen 6, 3, 336–339.

Waters, E.J., Peng, Z., et al., 1994. Solid-State13C NMR Investigation into Insoluble Deposits Adhering to the Inner Glass of Surface Bottled Red Wine J. Agric. Food Chem. 42, 8, 1761–1766.

Watrelot, A.A., Schulz, D.L., et al., 2017. Wine polysaccharides influence tannin-protein interactions Food Hydrocoll. 63, 571–579.

Worley, B. & Powers, R., 2016. PCA as a practical indicator of OPLS-DA model reliability HHS Public Access 4, 2, 97–103.

Yacco, R.S., Watrelot, A.A., et al., 2016. Red Wine Tannin Structure−Activity Relationships during Fermentation and Maceration J. Agric. Food Chem. 64, 860–869.

Zeng, L., Teissèdre, P.L., et al., 2016. Structures of polymeric pigments in red wine and their derived quantification markers revealed by high-resolution quadrupole time-of-flight mass spectrometry Rapid Commun. Mass Spectrom. 30, 1, 81–88.

Published
2018-12-14
Section
Articles

Most read articles by the same author(s)