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…

Some applications come from a method to concentrate proteins

All techniques usually used to assay proteins was not reliable in vegetable extract due to interferences with the components included in extracts like polyphenols, tanins, pectines, aromatics compounds. Absorbance at 280nm, Kjeldhal assay, Biuret and Lowry methods, Acid Bicinchonique technique and Bradford assay give the results depending on the composition of extract, on the presence or not of detergent and on the raw material (Marchal, 1995). Another difficulty in these extracts for the quantification of proteins comes from the large amount of water included in vegetable and the low concentration of proteins. Thus in red wines, proteins are usually not taken into account due to their low concentration (typically below 10 mgL-1) and to the presence of anthocyanis and polyphenols.

Evaluation of Polarized Projective Mapping as a possible tool for attributing South African Chenin blanc dry wine styles

Multiple Factor Analysis (MFA) According to the Chenin blanc Association of South Africa, there are three recognized dry wine styles, Fresh and Fruity (FF), Rich and Ripe Unwooded (RRU), and Rich and Ripe Wooded (RRW), classically attributed with the help of sensory evaluation. One of the “rapid methods” has drawn our attention for the purpose of simplifying and making style attribution for large sample sets, evaluated during different sessions, more robust. Polarized Projective Mapping (PPM) is a hybrid of Projective Mapping (PM) and Polarised Sensory Positioning (PSP). It is a reference-based method in which poles
(references) are used for the evaluation of similarities and dissimilarities between samples.

Analysis of peptide fraction from white wines

Among nitrogen compounds included in white wines, the peptide fraction is certainly the least studied, however this fraction is quantitatively the most important (Feuillat, 1974). Existing studies concern the fraction below 1 kDa and only for white and sparkling wines (Bartolomé et al, 1997, Desportes et al 2000). In this report, we have developed methods to isolate peptides from reference white wines. Then, we have applied this methodology with bitter wine to answer a research question: is there a relation between peptides and the bitterness of white wine as for some cheese for example (Furtado, 1984)?

Attractiveness and sweetness of red wines: Synergies between American oak barrels and mannoproteins

In partnership with a Bordeaux property wanting to improve the quality of its second wine, the effects of two factors, American oak barrels and mannoproteins were studied. Their impact on the attractiveness and sweetness of wines were characterized during two successive vintages (2012 and 2013). Vinification took place with a homogeneous batch of Cabernet Sauvignon. The wine was then divided up into various groups of five barrels of French and American oak, new or reused. Analyses of volatile and non-volatile wood compounds were undertaken at four months and eight months of wood ageing, by LC-MS and GC-MS.

Analysis of the oenological potentials of different oak forests in Hungary

Like France, Hungary has many oak forests used for making barrels since many years. But if the differences between the woods of the North, the East and the South-West forests of France are well known, this is probably not the case of Hungarian forests. However taking into account the essential differences of climates and soils, differences must be significant and the general name “Hungarian oak” must not have any real meaning. We have studied precisely (determination of concentrations of volatile and non-volatile wood compounds, anatomical criteria, measurement of antioxidant capacity) of oaks collected from northeastern Hungary and others collected from the Danube valley in the northwest of the country.