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…

OPTIMIZATION, VALIDATION AND APPLICATION OF THE EPR SPIN-TRAPPING TECHNIQUE TO THE DETECTION OF FREE RADICALS IN CHARDONNAY WINES

The aging potential of Burgundy chardonnay wines is considered as quality indicator. However, some of them exhibit higher oxidative sensitivity and premature oxidative aging symptoms, which are potentially induced by no-enzymatic oxidation such as Fenton-type reaction (Danilewicz, 2003). This chemical mechanism involves the action of transition metal, native phenolic compounds and oxygen which promote the generation of highly reactive oxygen species (ROS) such as hydroxyl radicals (OH) or 1-hydroxyethyl radicals (1-HER) from oxidation of ethanol. Such mechanism is involved in the radical oxidation occurring during bottle aging. According to Elias et al.,(2009a), the 1-HER is the most abundant radical in forced oxidation treated wines. Consequently, understanding its evolution kinetic in dry white wines is of great importance.

ACIDIC AND DEMALIC SACCHAROMYCES CEREVISIAE STRAINS FOR MANAGING PROBLEMS OF ACIDITY DURING THE ALCOHOLIC FERMENTATION

In a recent study several genes controlling the acidification properties of the wine yeast Saccharomyces cerevisiae have been identified by a QTL approach [1]. Many of these genes showed allelic variations that affect the metabolism of malic acid and the pH homeostasis during the alcoholic fermentation. Such alleles have been used for driving genetic selection of new S. cerevisiae starters that may conversely acidify or deacidify the wine by producing or consuming large amount of malic acid [2]. This particular feature drastically modulates the final pH of wine with difference of 0.5 units between the two groups.

VALORIZATION OF GRAPE WINE POMACE USING PULSED ELECTRIC FIELDS (PEF) AND SUPERCRITICAL CO₂ (SC CO₂) EXTRACTION

Wine grape pomace quantitatively and qualitatively represents the most important fraction of wine waste. Namely, this by-product makes ~ 20% of the total mass of vinified grapes, and it is characterized with high concentrations of polyphenolic antioxidants, as well as grape seed oil. Hence, valorization of wine pomace, as an alternative to traditionally employed disposal, has drown considerable interest in recent years. Earlier studies were mostly focused on the extraction of phenolics, while mechanisms enhancing the extraction of lipid fraction from grape pomace, as well as their impact on the grape seed oil quality are far less investigated.

WINE LEES AS A SOURCE OF NITROGEN FOR OENOCOCCUS OENI TO IMPROVE MALOLACTIC FERMENTATION PERFORMANCE

Malolactic fermentation (MLF) is a desired process in red and acidic white wines, after alcoholic fermentation (AF), carried out by the lactic acid bacterium (LAB) Oenococcus oeni. The advantages are an increase of pH, microbiological stabilization and organoleptic improvement of the final wine. However, the presence of stress factors such as ethanol, low pH, high total SO2, lack of nutrients and presence of inhibitors, could affect the successful completion of MLF [1]. Changes in amino acid composition and deficiencies in peptides after AF, showed that MLF can be delayed, signaling its importance for bacterial growth and L-malic acid degradation during MLF [2].

UNRAVELING THE CHEMICAL MECHANISM OF MND FORMATION IN RED WINE DURING BOTTLE AGING : IDENTIFICATION OF A NEW GLUCOSYLATED HYDROXYKETONE PRO-PRECURSOR

During bottle aging, the development of wine aroma through low and gradual oxygen exposure is often positive in red wines, but can be unfavorable in many cases, resulting in a rapid loss of fresh, fruity flavors. Prematurely aged wines are marked by intense prune and fig aromatic nuances that dominate the desirable bouquet achieved through aging (Pons et al., 2013). This aromatic defect, in part, is caused by the presence of 3-methyl-2,4-nonanedione (MND). MND content was shown to be lower in nonoxidized red wines and higher in oxidized red wines, which systematically exceeds the odor detection threshold (62 ng/L).