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…

Identification of caffeic acid as a major component of Moscatel wine protein sediment

Proteins play a significant role in the colloidal stability and clarity of white wines [1]. However, under conditions of high temperatures during storage or transportation, the proteins themselves can self-aggregate into light-dispersing particles causing the so-called protein haze [2]. Formation of these unattractive precipitates in bottled wine is a common defect of commercial wines, making them unacceptable for sale [3]. Previous studies identified the presence of phenolic compounds in the natural precipitate of white wine [4], contributing to the hypothesis that these compounds could be involved in the mechanism of protein haze formation.

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.

Anthocyanin accumulation and extractability during the maturation of the grapes of three varieties

Anthocyanin accumulation and extractability were studied in Tannat, Cabernet Sauvignon and Merlot grapes produced in the south of Uruguay in two consecutive seasons. Typical cultivation situations employed in the region for each variety were considered. A follow-up was carried out, considering 60 plants per vineyard, and the harvest was determined according to the technological indices of maturity. Samples of grapes were taken in duplicate in each vineyard periodically along grape maturation. The basic composition, polyphenolic potential and anthocyanin extractability were determined. Also, half of grapes were frozen and later peeled; skin extractions over 24 hs with a solution of 12% ethanol and pH 3.2 were carried out. The anthocyanin contents of the extracts obtained were determined by HPLC-DAD. The levels of anthocyanins reached the highest values before technological maturity. Anthocyanin extractability had a decrease during grape maturation.

Phenolic profiles of minor red grape cultivars autochthonous from the Spanish region of La Mancha

The phenolic profiles of little known red grape cultivars, namely Garnacho, Moribel and Tinto Fragoso, which are autochthonous from the Spanish region of La Mancha (ca. 600,000 ha of vineyards) have been studied over the consecutive seasons of years 2013 and 2014. The study was separately performed over the skins, the pulp and the seeds, and comprised the following phenolic types: anthocyanins, flavonols, hydroxycinnamic acid derivatives (HCADs), total proanthocyanidins (PAs) and their structural features. The selected grape cultivars belong to the Vine Germplasm Bank created in this region in order to preserve the great diversity of genotypes grown in La Mancha.

Effects of a new vacuum evaporation method on chemical and sensory properties of must and wine

A new process for vacuum evaporation was developed where evaporation takes place near the inner surface of a vortex produced by a rotor submerged in the liquid. Contrary to the state of the art the Vortex rotor process does not need a vacuum vessel but the rotating liquid creates a geometrically stable low pressure void surrounded by a vortex stabilized by the equilibrium between centrifugal forces and the pressure difference. First tests with water and sugar solutions at concentrations similar to grape must were conducted to verify the theoretical predictions, test the performance under different conditions and study the effect of various process parameters (Rösti et al 2015).