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 malolactic fermentation in barrels or stainless steel tanks on wine composition. Influence of the barrel toasting

Ellagitannin, anthocyanin and woody volatile composition of Cabernet Sauvignon wines aged in oak barrels for 12 months was evaluated. Depending on the container where malolactic fermentation (MLF) was carried out, two wine modalities were investigated: wines with MLF carried out in stainless steel tanks and barrel-fermented wines. Three toasting methods (medium toast, MT; medium toast with watering, MTAA; noisette) were considered for ageing of each wine modality. Sensory analyses (triangle and rating tests) were also performed. Two-way ANOVA of the raw experimental data revealed that the toasting method and the container where MLF took place, as well as the interaction between both factors, have a significant influence (p < 0.05) on ellagitannin, anthocyanin and woody volatile profiles of Cabernet Sauvignon wines.

Pesticide removal in wine with a physical treatment by molecular sieving

All along the winemaking process, conditioning and aging, wine is susceptible to be contaminated by different molecules. Contaminations can have various origins, related to wine microorganisms or as a result of an exogenous contamination. The aforementioned contamination of the wine can be caused by the migration of molecules from the materials in contact with the wine or by a contamination from exogenous molecules present in the air. Regardless of the source of the contamination, mainly two types of consequences can be observed.

Innovations in the use of bentonite in enology: interactions with grape and wine proteins, colloids, polyphenols and aroma compounds.

The use of bentonite in oenology rounds around the limpidity and the stability that determine consumer acceptability. As a matter of fact, the haze formation in wine reduces its commercial value and makes it unacceptable for sale. Stabilization treatments are, therefore, essential to ensure a long-time limpidity and to forecast the formation of deposits in the bottle. Bentonite that is normally used in oenology for clarifying-fining purpose, shows a natural clay-based mineral structure allowing it to swell and to jelly in water and hence in must and wine.

Impact of glutathione and elemental sulphur juice addition on the volatile thiol production in South African Sauvignon blanc wine

Three compounds, 3-mercaptohexanol (3MH), 3-mercaptohexyl-acetate (3MHA) and 4-mercapto-4-methylpentan-2-one (4MMP), also known as varietal thiols, have been identified to contribute positively to wine aroma and are responsible for the distinct gooseberry, grapefruit, guava and box tree character found in Sauvignon blanc wines. Certain volatile thiol compounds though, can cause off-aromas of onion, garlic, rubber and rotten egg, this group of molecules is known as reductive sulphur compounds (RSC). This study looks into how the addition of sulphur-compounds to Sauvignon blanc juice contributes to the varietal thiol (3MH and 3MHA) concentration and reductive sulphur compound concentration in South African Sauvignon blanc wine.

Fractionation of copper and iron in wine: Assessment of potential macromolecule and sulfur binding agents

Copper and iron are known to substantially impact wine stability through oxidative, reductive or colloidal phenomena. However, the binding of metal ions to different wine components under wine conditions, and the impact of this binding on the ability of the metal ions to induce spoilage processes, is not well understood. This study surveyed a range of red and white wines for an understanding of the variability of broad metal categories within the wines. The techniques utilized included an electrochemical constant current stripping potentiometry technique (ccSP), and solid phase extraction (SPE) fractionation of wine with subsequent analysis of the metal content of each fraction by inductively coupled plasma – optical emission spectroscopy (ICP-OES).