Macrowine 2021
IVES 9 IVES Conference Series 9 Petrolomics-derived data interpretation to study acetaldehyde-epicatechin condensation reactions

Petrolomics-derived data interpretation to study acetaldehyde-epicatechin condensation reactions

Abstract

During red wine ageing or conservation, color and taste change and astringency tends to reduce. These changes result from reactions of flavan-3-ols and/or anthocyanins among which condensation reactions with acetaldehyde are particularly important. The full characterization of these reactions has not been fully achieved because of difficulties in extracting and separating the newly formed compounds directly from wine. Model solutions mimicking food products constitute a simplified medium for their exploration, allowing the detection of the newly formed compounds, their isolation, and their structure elucidation. In this work, the reactions of (-)-epicatechin in the presence of acetaldehyde were studied in model solution systems at wine pH by UPLC-LTQ-Orbitrap-high resolution mass spectrometry. High resolution mass spectrometry provides exact mass measurements thus leading to elemental composition assignment of molecules which is an essential step for identification of new-formed compounds. By applying petrolomics-derived data interpretation strategies such as the untargeted Van Krevelen diagrams and Kendricks mass defect plots, described earlier in black tea thearubigins (1), more than 40 compounds were found including the homogeneous bridged derivatives and the well-known vinyl and ethanol adducts (2,3). Other compounds from polymer series such as the hexamer and heptamer epicatechin bridged derivatives and several xanthylium salts were identified for the first time. Consequently, in this work, a structural model for acetaldehyde-mediated reaction cascades involving formation of ethanol adducts, vinyl adducts, ethyl brides, loss of water molecules to form xanthylium salts…was developed.

References 1. Kuhnert et al. Arch. Biochem. Biophys., 2010, 501, 37–51 2. Fulcrand et al. J. Chromatogr- A. 1996, 752, 85-91 3. Es Safi et al. J. Agric. Food Chem. 1999, 47, 2088-2095

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Article

Authors

Anna Vallverdu-Queralt*, Emmanuelle Meudec, Nicolas Sommerer, Rosa Maria Lamuela Ravento, Veronique Cheynier

*INRA

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Effect of ageing with Specific Inactivated Dry Yeasts on the volatile composition of Sauvignon Blanc and Carménère wines

Úbeda-Aguilera, C a, b, Peña-Neira, A.b Del Barrio-Galán, R.b, c a Biomedical Sciences Institute, Science Faculty, Universidad Autónoma de Chile, Chile. b Department of Agro-Industry and Enology, Faculty of Agronomical Sciences, University of Chile, Post Office Box 1004, Santa Rosa 11315, La Pintana, Santiago, Chile c Lallemand Inc. Chile y Compañía Limitada, Rosario Norte 407, piso 6, Las Condes, Santiago, Chile The wine is a complex matrix made up of several compounds which can interact among themselves throughout the wine ageing process, thereby modifying their sensorial characteristics. It is well known that during ageing of wines on lees, polysaccharides (mainly mannoproteins) can be released and can interact with the aromatic fraction modifying its volatility.

The challenge of quality in sulphur dioxide free wines: natural polyphenol alternatives

Sulphur dioxide (SO2) seems indispensable in winemaking because of its properties. However, a current increasing concern about its allergies effects in food product has addressed the international research efforts on its replacement. This supposes a sufficient knowledge of its properties and conditions of use. Several studies compared SO2 properties against new alternatives that are supposed to overcome SO2 disadvantages. Firstly, the state of art on SO2 wine replacements is revised, and secondly, the last promising results using natural enriched polyphenol extracts are shown.

Use of computational modelling for selecting adsorbents for improved fining of wine

The occurrence of faults and taints in wine, such as those caused by microbial spoilage or various taints, have resulted in significant financial losses to wine producers. The wine industry commits significant financial resources towards fining and taint removal processes each year. Fining involves the addition of one or more adsorptive substrates to juice or wine to bind certain components, thus reducing their concentration [1]. However, these processes are often not selective and can also remove desirable flavour and aroma compounds.

The commercial yeast strain as a significant source of variance for tyrosol and hydroxytyrosol in white wine

Tyrosol (TYR) and hydroxytyrosol (HYT) are bioactive phenols present in olive oil and wine, basic elements of the Mediterranean diet. TYR is reported in the literature for its interesting antioxidant, cardioprotective and anti-inflammatory properties. In wine, its concentration can reach values as high as about 40 mg/L
[Pour Nikfardjam et al. 2007] but, more frequently, this phenol – derived from yeast metabolism of tyrosine during fermentation – is present at lower levels, generally higher in red wines compared to whites. HYT was measured for the first time by Di Tommaso et al. [1998] in Italian wines – with maximum values of 4.20 mg/L and 1.92 mg/L for red and white wines, respectively – while definitely lower concentrations have been found later in Greek samples.

Effect of concentration and competition between different fungicide residues on the adsorption efficiency of activated vegetal fibres for treatment of wine

Vineyards are strongly exposed to fungal diseases, attacks from insects and competition with weeds. Most treatments used on grape vines contain synthetic active substances, which may be transferred to the wine. Such pesticides have a negative image because many active substances are potential health hazards. A specific oenological treatment allowing the reduction of pesticide residues in wine based on activated vegetable fibres (AVF) is under examination by the International Organisation for Vine and Wine. This technique works efficiently and alters the wine only little (Lempereur et al. 2014).