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…

Analysis of off flavours in grapes infected with the fungal bunch rot pathogens, Aspergillus, Botrytis and Pencillium

Fungal bunch rots of grapes cause major losses to grape yield worldwide, yet the impact these moulds have on grape and wine quality is not well characterised. We sought to investigate the formation of unwanted volatile compounds of fungal origin in both synthetic grape juice culture media and in inoculated grape berries. Botrytis cinerea, Aspergillus niger, Aspergillus carbonarius, or Pencillium expansum were grown in synthetic grape juice medium and the culture homogenates analysed 4 and 7 days post inoculation. HS-SPME-GC-MS analysis of the culture homogenates 4 days post inoculation demonstrated that each of the fungi examined produced varying quantities of the mushroom or fungus-like aroma compounds, 1-Octen-3-ol, 1-Octen-3-one and 3-Octanone with A. carbonarius producing up to ten times the amounts of all three metabolites per mg of dry mycelium.

Development and validation of a standardized oxidation assay for the accurate measurement of the ability of different wines to form “de novo” oxidation-related aldehydes

From the standpoint of wine aroma oxidation there are two effects observed: aroma degradation of oxygen sensitive compounds (polyfunctional mercaptans) and the appearance of new substances with high aromatic power (acetaldehyde, methional, phenylacetaldehyde, sotolon, alkenals, isobutanal and 2, 3-metylbutanals) (1-5). According to our experience, Strecker aldehydes are compounds with highest sensory relevance in the oxidative degradation of many wines (5-7).

Quantification of red wine phenolics using ultraviolet-visible, near and mid-infrared spectroscopy combined with chemometrics

The use of multivariate statistics to correlate chemical data to spectral information seems as a valid alternative for the quantification of red wine phenolics. The advantages of these techniques include simplicity and cost effectiveness together with the limited time of analysis required. Although many
publications on this subject are nowadays available in the literature most of them only reported feasibility
studies. In this study 400 samples from thirteen fermentations including five different cultivars plus 150
wine samples from a varying number of vintages were submitted to spectrophotometric and chromatographic phenolic analysis.

Assessing the effect of oak derived aromas on mouthfeel perception in Chardonnay wine

Mouthfeel is an important quality parameter for Chardonnay wines, particularly those aged in oak. While research on mouthfeel has traditionally focused on the impact of non-aromatic compounds, the role of aroma compounds has largely been over looked. However, in wine as well as other food interactions between retronasal aroma and mouthfeel have been noted. The goal of this research was to investigate the impact of wine aroma on the perception of mouthfeel. Because of the importance of oak aging in the development of Chardonnay mouthfeel, the impact of oak aromas on perceived mouthfeel was explored. Aroma compounds associated with oak (ethyl palmitate, eugenol, furfural, isoeugenol, syringaldehyde, vanillin and whiskey lactone) were added to two different Chardonnay wines; one with no oak influence and one fermented in neutral oak. Low and high concentrations of the compounds were added based on concentrations typically found in barrel aged Chardonnay wine.

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.