IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Optimisation de la fertilisation du Cot sur le Causse de l’Appellation d’Origine Contrôlée Cahors

The Appellation d’Origine Contrôlée area of ​​Cahors (Lot) covers an area of ​​21,700 ha, spread over 45 municipalities, of which only 4,300 are planted with vines. The main grape variety of this AOC is the Cot noir which represents 70% of the grape varieties, thus giving their typicality to the wines of this region; but despite this importance, to our knowledge, its physiology has remained relatively unstudied.

Read More

Assessing bunch architecture for grapevine yield forecasting by image analysis

It is fundamental for wineries to know the potential yield of their vineyards as soon as possible for future planning of winery logistics. As such, non-invasive image-based methods are being investigated for early yield prediction. Many of these techniques have limitations that make it difficult to implement for practical use commercially. The aim of this study was to assess whether yield can be estimated using images taken in-field with a smartphone at different phenological stages. The accuracy of the method for predicting bunch weight at different phenological stages was assessed for seven different varieties.

Read More

Oxidability of wines made from Spanish minority grape varieties

The phenolic profile of a wine plays an essential role in its oxidative capacity and in both white and red wines it defines its shelf life[1]. The study of minority varieties to produce wines with peculiar characteristics necessarily includes the phenolic and oxidative characterization of the wines produced. This paper presents the study of wines made from 24 minority and majority white and red grape varieties, focusing on phenolic characteristics (total phenols, slightly polymerized phenols, highly polymerized phenols, anthocyanins…), color, as well as parameters related to the oxidability of the wines and their capacity to consume oxygen [2].

Read More

Hplc-ms analysis of carotenoids as potential precursors for 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) in riesling grapes

In recent years, an undesirable premature “aged” character has been noticed in a growing number of young Riesling wines, associated with extreme weather conditions leading to increased radiation intensity and/ or sun exposure of grapes.

Read More

Weather classification over the Western Cape (February, 1996 – 2000) and viticultural implications in the Stellenbosch wine district

Une étude préliminaire des situations météorologiques journalières a été réalisée pour l’Afrique du Sud et pour les mois de février (période de maturation des raisins dans la Province occidentale du Cap), à l’image de la classification synoptique réalisée aux latitudes tempérées en France (Jones & Davis, 2000), afin d’étudier les relations entre le climat et la viticulture à des latitudes plus basses.

Read More