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…

Elicitors used as a tool to increase stilbenes in grapes and wines

The economic importance of grapevine as a crop plant makes Vitis vinífera a good model system to study the improvement of the nutraceutical properties of food products (Vezulli et al. 2007). Stilbenes in general, and trans-resveratrol in particular, have been reported to be responsible for various beneficial effects. Resveratrol´s biological properties include antibacteria and antifungal effects, as well as cardioprotective, neuroprotective and anticâncer actions (Guerrero et al. 2010 ). Stilbenes can be induced by biotic and abiotic elicitors since they are phytoalexins (Bavaresco et al. 2001).

Intelligent article to control the internal pressure in continue in bottles

An intelligent packaging might, among others, provide information and allow monitoring of the quality of the packed product or its surrounding environment. A recent project on micro-flow wine bottles closed with aluminium screw cap and tightness liner, highlighted the importance of monitoring the internal overpressure continuously, in real-time and at least for 72 hours, since the internal pressure on the tightness liner and the micro-flow are related. Real-time and continuous measurements are not the standard methods of measurement of the overpressure, yet. The most used equipment for the determination of the pressure in wine bottle is the aphrometer, a destructive device that supplies a single value of pressure.

Light-struck taste in white wine: enological approach for its prevention

Light-struck taste is a defect prevalent in white wines bottled in clear glass light-exposed for a considerable amount of time leading to a loss of color and appearance of sulfur-like odors. The reaction involves riboflavin (RF), a highly photosensitive compound that undergoes to intermolecular photoreduction by the uptake of two electron equivalents from an external donor, the methionine. The reaction includes different steps forming methional which is extremely unstable and decomposes to methane thiol and acrolein. The reaction of two molecules of methane thiol yields dimethyl disulfide. Methane thiol is highly volatile, has a low perception threshold (2 to 10 µg/L in wine) and confers aroma-like rotten eggs or cabbage.

Merging fast sensory profiling with non-targeted GC-MS analysis for multifactorial experimental wine making

Wine aroma is influenced by several viticultural and oenological factors. In this study we used experimental wine making in a full factorial design to determine the impact of grapevine age, must turbidity, and yeast strain on the aroma of Vitis vinifera L. cv. Riesling wines. A recently developed, non-targeted SPME-GC-MS fingerprinting approach for wine volatiles was used. This approach includes the segmentation and mathematical transformation of chromatograms in combination with Parallel Factor Analysis (PARAFAC) and subsequent deconvolution of important chromatogram segments.

Influence of preflowering basal leaf removal on aromatic composition of cv. Tempranillo wine from semiarid climate (Extremadura Western Spain)

Abstract In this work the effects of early leaf removal performed manually at preflowering phenological stage, on the volatile composition of Tempranillo (Vitis vinifera L.) wines were studied. From 2009-2011 vintages 34 wine volatile compounds were identified and quantified by gas chromatography-mass spectrometry (GC-MS) where early leaf removal only modified 25 of them. The total C6 compounds, acetates and volatiles acids (with exception of isobutyric acid) were affected by defoliation, whereas alcohols and esters showed a minor effect. Furthermore the vintage effect also was shown.