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…

Characterization of commercial enological tannins and its effect on human saliva diffusion

Commercial oenological tannins (TECs) are widely used in the wine industry. TECs are rich in condensed tannins, hydrolyzable tannins or a mixture of both. Wine grapes are a important source of proanthocyanidins or condensed tannins while oak wood possess a high concentration of hydrolyzable tannins (Obreque-Slier et al., 2009). TECs contribute with the antioxidant capacity of wine, catalyze oxide-reduction reactions and participate in the removal of sulfur compounds and metals.

Non-invasive headspace sorptive extraction for monitoring volatile compounds production by saccharomyces and non-saccharomyces strains throughout alcoholic fermentation

Wine is a solution containing abundant volatile compounds which contribute to their aroma. Many of them are produced by yeast as metabolism by-products. Different yeast strains produce different volatile profiles. The possibility of studying the evolution of volatile compounds during fermentation, using sampling methods that not alter the volume of fermentation media, is of great interest. In spite of this, non-invasive methods to monitoring the evolution of volatile profile during fermentation have been seldom used. The goals of this work were to use by first time the headspace sorptive extraction (HSSE) as non-invasive method to monitor the evolution of volatile profiles throughout alcoholic fermentation and to study the changes on volatile profiles produced by Saccharomyces cerevisiae and Lachancea thermotolerans during fermentation of a must with high sugar content.

New biological tools to control and secure malolactic fermentation in high pH wines

Originally, the role of the malolactic fermentation (MLF) was simply to improve the microbial stability of wine via biological deacidification. However, there is an accumulation of evidence to support the fact that lactic acid bacteria (LAB) also contribute positively to the taste and aroma of wine. Many different LAB enter into grape juice and wine from the surface of grape berries, cluster stems, vine leaves, soil and winery equipment. Due to the highly selective environment of juices and wine, only a few types of LAB are able to grow.

Sensory definition of green aroma concept in red French wines. Evidence for the contribution of novel volatile markers

The aromatic complexity of a wine results from the perception of the association of volatile molecules and each aroma can be categorized into different families. The “green” aromas family in red wines has retained our attention by its close link with the fruity perception. In that study, the “green” olfactory concept of red wines was considered through a strategy combining both sensory analysis and hyphenated chromatographic techniques including HPLC and MDGC (Multidimensional Gas Chromatography). The aromatic space of this concept was specified by lexical generation through a free association task on 22 selected wines by a panel of wine experts. Then, 70 French red wines were scored on the basis of the intensity of their “green” and “fruity” attributes.

Impact of industrial-scale serial filtration on macromolecules in red wines

Filtration is a critical step in ensuring the clarity and microbial stability of wine prior to bottling. However the process of filtering potentially reduces red wine quality by removing some of the macromolecules that contribute to the texture of the wine. Commercial red wines, Cabernet Sauvignon (CAS) and Shiraz (SHZ), of two vintages and two grades (premium grade wines from the older vintage: CAS13 and SHZ13; and standard grade wines from a younger vintage: CAS14 and SHZ14) were filtered through industrial-scale commercial filtration units prior to bottling. Samples were taken before and after cross-flow filtration, lenticular filters, 0.65 µm and 0.45 µm pore size nylon membrane filters. The concentration and composition of macromolecules, including tannins and polysaccharides, were measured in all samples as well as particle size distribution and wine colour.