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…

Impact of sulfur compounds to the antioxidant stability of white wines

The chemical mechanisms involved in oxidation/reduction potential of wine during winemaking and aging are affecting its color, aroma and taste. Chemical oxidation is one of the major causes of development of off-flavors during ageing1. Thus, the chemical changes in wine during storage should be controlled to ensure the sensory quality of the product and avoid consumer rejection that will compromise the economic value of the product. The 1-hydroxyethyl radical has been recognized as the key radical intermediate in the oxidative reactions in wine2. Based on the kinetic study of POBN-1-hydroxyethyl spin adduct formation in wines initiated via the Fenton reaction, a novel tool was recently developed in our laboratory to quantify the resistance of wines against oxidation3.

The effect of cropload on the volatile aroma characteristics of ‘Beihong’ and ‘Beimei’ red wine

Beihong and Beimei were bred as winemaking cultivars released by Institute of Botany, the Chinese Academy of Sciences in 2008. The cultivars are selected from the population of ‘Muscat Hamburg’ (Vitis vinifera) ×V. amurensis. They are extended to most provinces in North of China because they have strong resistance to cold and disease and need not be buried in soil in winter. To better understand the effect of cropload on volatile compounds during wine-making, we surveyed volatiles composition and content of different cropload level in 3-years-old ‘Beihong’ and ‘Beimei’ vines which planted in east foot of Helan mountain of Ningxia (EHN).

Extraction of polyphenols from grape marc by supercritical fluid extraction (SFE) and evaluation of their ‘bioavailability’ as dietary supplements

In the winemaking process, several compounds that remain in the grape skins and seeds after the fermentation stage are bioactive-compounds (substances with potential beneficial effects on health) that can be extracted in order to recovery valuable substances with a high commercial value for the cosmetic, food (nutraceuticals) and pharmaceutical industries. The skins contain significant amounts of bioactive substances such as tannins (16-27%) and other polyphenolic compounds (2-6.5%) in particular, catechins, anthocyanins, proanthocyanins, quercetin , ellagic acid and resveratrol.

Study of the volatil profile of minority white varieties

The genetic material preservation is a priority issue in winemaking research. The recovery of minority grape varieties can control the genetic erosion, contributing also to preserve wine typical characteristics. In D.O.Ca. Rioja (Spain) the number of grown white varieties has been very limited, representing Viura the 91% of the cultivated white grape area in 2005, while the others, Garnacha Blanca and Malvasía riojana, hardly were grown. For this reason, a recovery and characterization study of plant material was carried out in this region. In 2008, the results obtained allowed the authorization of three minority white varieties: Tempranillo Blanco, Maturana Blanca and Turruntés.

Impact of drought stress on concentration and composition of wine proteins in Riesling

Protein haze in white wines is a major technological and economic problem of the wine industry. Field tests were carried out in steep slope vineyards planted with Riesling grapes over 3 dry growing seasons to study the effect of drought stress on the concentration of proteins in the resulting wines. Plots suffering from drought stress were compared with surrounding drip irrigated plots. Riesling grapes were processed into wines by conventional procedures. Protein amounts of the isolated wine colloids of the stressed samples were always higher than those of the watered samples(mean watered 13.8 ± 0.44, mean stressed 17.4 ± 0.40 g 100 g-1). As a consequence, higher bentonite doses were needed to achieve protein haze stability of the drought stressed treatments.