terclim by ICS banner
IVES 9 IVES Conference Series 9 IDENTIFICATION OF NEW RESVERATROL DERIVATIVES FORMED IN RED WINE AND THEIR BIOLOGICAL PROPERTIES

IDENTIFICATION OF NEW RESVERATROL DERIVATIVES FORMED IN RED WINE AND THEIR BIOLOGICAL PROPERTIES

Abstract

Stilbenes are natural bioactive polyphenols produced by grapevine. Recently, we have reviewed the natural presence of these compounds in wines [1]. This study showed that the resveratrol and its glycoside, the piceid, are the most abundant stilbenes in wines. Resveratrol is a well-known stilbene with a wide range of biological activities. Due to its specific structure, resveratrol can be oxidized in wines to form various derivatives including oligomers [2]. In this study, we investigate the resveratrol and piceid transformation in wines.

First, the transformations of resveratrol and piceid by oxidative coupling in presence of metals and by photo-oxidation under light exposure were investigated in model solutions. Structural elucidation of oxidative products was obtained by NMR. Secondly, the formation in wines of these compounds was monitored by liquid chromatography coupled with accurate mass spectrometry. The main results will be presented and discussed. Finally, the biological properties of these compounds were evaluated on cell line models. The results will be presented and compared with those obtained with resveratrol.

 

1. Benbouguerra N., Hornedo-Ortega R., Garcia F., El Khawand T., Saucier C., Richard T., Trends in Food Science & Technology, 112, 362-381, 2021
2. El Khawand, T.; Valls Fonayet, J.; Da Costa, G.; Hornedo-Ortega, R.; Jourdes, M.; Franc, C.; Revel, G.; Decendit, A.; Krisa, S.; Richard, T., Food Research International 132, 109068, 2020

DOI:

Publication date: February 9, 2024

Issue: OENO Macrowine 2023

Type: Poster

Authors

Ayoub Jaa1,2, Anthony Pébarthé-Courrouilh¹, Josep Valls Fonayet¹, Toni El Khawand¹, Stéphanie Krisa¹, Grégory Da Costa¹, Anto-nio Palos Pinto¹, Marie-Laure Iglésias¹, M. Begoña Ruiz-Larrea², José Ignacio Ruiz-Sanz², Stéphanie Cluzet¹, Tristan Richard¹

1. Univ. Bordeaux, Bordeaux Sciences Agro, Bordeaux INP, INRAE, OENO, UMR 1366, ISVV, F-33140 Villenave d’Ornon, France
2. Free Radicals and Oxidative Stress (FROS) research group of the Department of Physiology, Medicine and Nursing School, University of the Basque Country UPV/EHU, 48940-Leioa, Bizkaia, Spain

Contact the author*

Keywords

Stilbene, resveratrol, oxidative coupling, isomerisation

Tags

IVES Conference Series | oeno macrowine 2023 | oeno-macrowine

Citation

Related articles…

VOLATILE AND GLYCOSYLATED MARKERS OF SMOKE IMPACT: EVOLUTION IN BOTTLED WINE

Smoke impact in wines is caused by a wide range of volatile phenols found in wildfire smoke. These compounds are absorbed and accumulate in berries, where they may also become glycosylated. Both volatile and glycosylated forms eventually end up in wine where they can cause off-flavors. The impact on wine aroma is mainly attributed to volatile phenols, while in-mouth hydrolysis of glycosylated forms may be responsible for long-lasting “ashy” aftertastes (1).

THE EFFECT OF COPPER ON THE PRODUCTION OF VARIETAL THIOLS DURING THE ALCOHOLIC FERMENTATION OF COLOMBARD AND GROS MANSENG GRAPE JUICES

Nowadays, the rapid growth of vineyards with organic practices and the use of copper as the only fun-gicide against downy mildew raises again the question of the effect of copper on varietal thiols in wine, especially 3-sulfanylhexan-1-ol (3SH) and its acetate (3SHA). A few decades ago, several works indicated that the use of copper in the vineyard had a negative effect on the content of varietal thiols in Sauvignon blanc wines [1, 2]. However, these studies only considered the concentration of the reduced form (RSH) of varietal thiols, without quantifying the oxidised ones. For this purpose, we proposed to monitor both reduced and oxidised forms of varietal thiols in wine under copper stress during alcoholic fermentation to have a more complete picture of the biological and chemical mechanisms.

DEVELOPMENT OF DISTILLATION SENSORS FOR SPIRIT BEVERAGES PRODUCTION MONITORING BASED ON IMPEDANCE SPECTROSCOPY MEASUREMENT AND PARTIAL LEAST SQUARES REGRESSION (PLS-R)

During spirit beverages production, the distillate is divided in three parts: the head, the heart, and the tail. Acetaldehyde and ethanol are two key markers which allow the correct separation of distillate. Being toxic, the elimination of the head part, which contains high concentration of acetaldehyde, is crucial to guarantee the consumer’s health and security. Plus, the tail should be separated from the heart based on ethanol concentration.

EFFECT OF DIFFERENT TEMPERATURE AND WATER-LOSS DEHYDRATION CONDITIONS ON THE PATTERN OF FREE AND GLYCOSYLATED VOLATILE METABOLITES OF ITALIAN RED GRAPES

Post-harvest grape berries dehydration/withering are worldwide applied to produce high-quality sweet and dry wines (e.i., Vin Santo, Tokaji, Amarone della Valpolicella). Temperature and water loss impact grape metabolism [1] and are key variables in modulating the production of grape compounds of oenological interest, such as Volatile Organic Compounds (VOCs), secondary metabolites responsible for the aroma of the final wine.
The aim of this research was to assess the impact of post-harvest dehydration on free and glycosylated VOCs of two Italian red wine grapes, namely Nebbiolo and Aleatico, dehydrated in tunnel under controlled condition (varied temperature and weight-loss, at constant humidity and air flow). From these grapes Sforzato di Valtellina Passito DOCG and Elba Aleatico Passito DOCG, respectively.

CHANGES IN METABOLIC FLUXES UNDER LOW PH GROWTH CONDITIONS: CAN THE SLOWDOWN OF CITRATE CONSUMPTION IMPROVE OENOCOCCUS OENI ACID-TOLERANCE?

Oenococcus oeni is the main Lactic Acid Bacteria responsible for malolactic fermentation, converting malic acid into lactic acid and carbon dioxide in wines. Following the alcoholic fermentation, this second fermentation ensures a deacidification and remains essential for the release of aromatic notes and the improvement of microbial stability in many wines. Nevertheless, wine is a harsh environment for microbial growth, especially because of its low pH (between 2.9 and 3.6 depending on the type of wine) and nutrient deficiency. In order to maintain homeostasis and ensure viability, O. oeni possesses different cellular mechanisms including organic acid metabolisms which represent also the major pathway to synthetize energy in wine.