WAC 2022 banner
IVES 9 IVES Conference Series 9 WAC 9 WAC 2022 9 4 - WAC - Oral presentations 9 Identification and biological properties of new resveratrol derivatives formed in red wine

Identification and biological properties of new resveratrol derivatives formed in red wine

Abstract

Resveratrol is a well-known wine constituent with a wide range of activities. In wines, resveratrol can be oxidized to form various derivatives including oligomers [1]. In this study, resveratrol derivative transformation in hydroalcoholic solution was investigated by oxidative coupling using metals. De novo resveratrol derivatives were synthetized and analysed by NMR and MS experiments including new molecules. The presence of these compounds was sought in red wines using an ultra-high-performance liquid chromatography tandem mass spectrometry (UHPLC MS/MS). This work confirmed the presence of these compounds in red wines in content comparable to that of resveratrol. Finally, biological properties of these compounds were evaluated in breast cancer and macrophage cell models.

DOI:

Publication date: June 14, 2022

Issue: WAC 2022

Type: Article

Authors

Tristan Richard, Ayoub Jaa, Anne Gutiérrez Sainz,  Josep Valls Fonayet,Stéphanie Krisa, M. Begoña Ruiz-Larrea, José Ignacio Ruiz-Sanz, Tristan Richard

Presenting author

Tristan Richard – Université de Bordeaux, Œnologie EA 4577, USC 1366 INRA, INP, ISVV, 210 chemin de Leysotte, 33882 Villenave d’Ornon, France

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. UMR 1366, Univ. Bordeaux, INRAE, Bordeaux INP, Bordeaux Science Agro, UMR OENO, ISVV, 210 chemin de Leysotte, 33882 Villenave d’Ornon, FranceINRAE, UR Œnologie, EA 4577, USC 1366, ISVV, 210 Chemin de Leysotte, F 33882 Villenave d’Ornon, France.1Université de Bordeaux, Œnologie EA 4577, USC 1366 INRA, INP, ISVV, F-33140 Villenave d’Ornon, France

Contact the author

Keywords

resveratrol, oxidative coupling, wine, biological activities

Tags

IVES Conference Series | WAC 2022

Citation

Related articles…

Effect of one-year cover crop and arbuscular mycorrhiza inocululation in the microbial soil community of a vineyard

The microbial composition of the soil is an important factor to consider in viticulture, since its influence on the “terroir” and on the organoleptic properties of the wine have been demonstrated. Different agronomic techniques have the potential to modify the composition and functionality of the soil microbial community. Maintaining green covers is known to increase soil microbial diversity. The direct application of inoculum of beneficial microorganisms to the soil has also been used to increase their abundance. However, the environmental conditions of each site seem to have a determining weight in the result of these practices. In this study, we compared the effect on the microbial community of a cover crop with legumes in autumn and the inoculation of grapevines with commercial inoculum bases on Rhizophagus irregularis and Funeliformis mosseae in the previous spring. The study has been carried out in a vineyard in Binissalem, Mallorca, Spain. After applying the treatments, we will analyze the soil microbial communities using the data obtained from Illumina amplification of soil DNA from the 16S and ITS regions to analyze bacteria and fungi community, respectively. In addition, we will record the physicochemical characteristics of the soil at each sampling point. The result showed that agronomic management, in the short term, has less influence than soil characteristics on the composition of the soil microbiome. With these results, we can conclude that in a vineyard, agricultural techniques should focus on improving the characteristics of the soil to improve the biodiversity of the soil microbiota.

Protected Designation of Origin (D.P.O.) Valdepeñas: classification and map of soils

The objective of the work described here is the elaboration of a map of the different types of vineyard soils that to guide the famers in the choice of the most productive vine rootstocks and varieties. 90 vineyard soils profiles were analysed in the entire territory of the Origen Denominations of Valdepeñas. The sampling was carried out in 2018 (June to October) by making a sampling grid, followed by photointerpretation and control in the field. The studied soils can be grouped into 9 different soil types (according to FAO 2006 classification): Leptosols, Regosols, Fluvisols, Gleysols, Cambisols, Calcisols, Luvisols and Anthrosols. A map showing the soil distribution with different type of soils has been made with the ArcGIS program. Regarding to the choice of rootstock, Calcisoles are soils with a high active limestone content, so the rootstocks used in these soils must be resistant to this parameter; Luvisols are deep soils with high clay content, so they will support vigorous rootstocks. Because the cartographic units are composed of two or more subgroups, with are associated in variable proportions, 9 different soil associations have been established; Unit 1: Leptosols, Cambisols and Luvisols (80%, 15% and 5% respectively); Unit 2: Cambisols with Regosols and Luvisols (40%, 30% and 30% respectively); Unit 3: Cambisols and Gleysols with Regosols (40%, 40% and 20% respectively); Unit 4: Regosols with Cambisols, Leptosols and Calcisols (40%, 30%, 15% and 15% respectively); Unit 5: Cambisols, Leptosols, Calcisols and Regosols (25% each of them); Unit 6: Luvisols with Cambisol and Calcisols (80%, 10% and 10% respectively); Unit 7: Luvisols and Calcisols with Cambisols (40%, 40% and 20% respectively); Unit 8: Calcisols with, Cambisols and Luvisols (80%, 10% and 10% respectively); Unit 9: Anthrosols. These study allow to elaborate the first map of vineyard soils of this Protected Designation of Origin in Castilla-La Mancha.

Effect of fertigation strategies to adapt PGI Côtes de Gascogne production to hot vintage

The development of fertigation could be a possible solution to adapt PGI Côtes de Gascogne (south-western France) wine production to climate change. The goal would be to limit the negative effects of water stress on yield performance expectation (around 15 tons per hectare) and to make the use of fertilizers more efficient. This study aimed to compare the effects of three strategies of water and minerals supply on grapes and wines qualities. Two fertigation practices were compared to a rainfed control which is the current standard of the local grape growing production. The fertilizers (nitrogen and potassium) were (i) fully brought by irrigation pipe during the season, (ii) partially brought by irrigation pipe and partially on the soil or (iii) fully brought on the soil at the beginning of the season for the non-irrigated control (local standard). The trial was run on cv. Colombard trained on spur pruned with vertical shoot positioning system on a sandy-silty-clay soil over the 2020 vintage which was particularly hot for the region. Moderate to strong water deficit appeared during the growing period of the berries and held on after veraison. Irrigation strategies allowed for maintaining grapevine without water deficit and being significantly different from the control water status. Grapevine with fully or partial fertigation strategies produced 25% more yield mainly due to the increase of the bunch weight. Also, the fully fertigation showed the best ratio between yield and maturity and brought 30% less of fertilizers (both nitrogen and potassium) than the two other strategies. Finally, the analysis of aromatic compounds in Colombard wines, varietal thiols family, showed the same level of concentrations for the 3 treatments, confirming that the yield performance did not impact the aromatic potential in this trial.

What are the optimal ranges and thresholds for berry solar radiation for flavonoid biosynthesis?

In wine grape production, canopy management practices are applied to control the source-sink balance and improve the cluster microclimate to enhance berry composition. The aim of this study was to identify the optimal ranges of berry solar radiation exposure (exposure) for upregulation of flavonoid biosynthesis and thresholds for their degradation, to evaluate how canopy management practices such as leaf removal, shoot thinning, and a combination of both affect the grapevine (Vitis vinifera L. cv. Cabernet Sauvignon) yield components, berry composition, and flavonoid profile under context of climate change. First experiment assessed changes in the grape flavonoid content driven by four degrees of exposure. In the second experiment, individual grape berries subjected to different exposures were collected from two cultivars (Cabernet Sauvignon and Petit Verdot). The third experiment consisted of an experiment with three canopy management treatments (i) LR (removal of 5 to 6 basal leaves), (ii) ST (thinned to 24 shoots per vine), and (iii) LRST (a combination of LR and ST) and an untreated control (UNT). Berry composition, flavonoid content and profiles, and 3-isobutyl 2-methoxypyrazine were monitored during berry ripening. Although increasing canopy porosity through canopy management practices can be helpful for other purposes, this may not be the case of flavonoid compounds when a certain proportion of kaempferol was achieved. Our results revealed different sensitivities to degradation within the flavonoid groups, flavonols being the only monitored group that was upregulated by solar radiation. Within different canopy management practices, the main effects were due to the ST. Under environmental conditions given in this trial, ST and LRST hastened fruit maturity; however, a clear improvement of the flavonoid compounds (i.e., greater anthocyanin) was not observed at harvest. Methoxypyrazine berry content decreased with canopy management practices studied. Although some berry traits were improved (i.e. 2.5° Brix increase in berry total soluble solids) due to canopy management practices (ST), this resulted in a four-fold increase in labor operations cost, two-fold decrease in yield with a 10-fold increase in anthocyanin production cost per hectare that should be assessed together as the climate continues to get hot.

The potential of multispectral/hyperspectral technologies for early detection of “flavescence dorée” in a Portuguese vineyard

“Flavescence dorée” (FD) is a grapevine quarantine disease associated with phytoplasmas and transmitted to healthy plants by insect vectors, mainly Scaphoideus titanus. Infected plants usually develop symptoms of stunted growth, unripe cane wood, leaf rolling, leaf yellowing or reddening, and shrivelled berries. Since plants can remain symptomless up to four years, they may act as reservoirs of FD contributing to the spread of the disease. So far, conventional management strategies rely mainly on the insecticide treatments, uprooting of infected plants and use of phytoplasma-free propagation material. However, these strategies are costly and could have undesirable environmental impacts. Thus, the development of sustainable and noninvasive approaches for early detection of FD and its management are of great importance to reduce disease spread and select the best cultural practices and treatments. The present study aimed to evaluate if multispectral/hyperspectral technologies can be used to detect FD before the appearance of the first symptoms and if infected grapevines display a spectral imaging fingerprint. To that end, physiological parameters (leaf area, chlorophyll content and photosynthetic rate) were collected in concomitance to the measurements of plant reflectance (using both a portable apparatus and a remote sensing drone). Measurements were performed in two leaves of 8 healthy and 8 FD-infected grapevines, at four timepoints: before the development of disease symptoms (21st June); and after symptoms appearance (ii) at veraison (2nd August); at post-veraison (11th September); and at harvest (25th September). At all timepoints, FD infected plants revealed a significant decrease in the studied physiological parameters, with a positive correlation with drone imaging data and portable apparatus analyses. Moreover, spectra of either drone imaging and portable apparatus showed clear differences between healthy and FD-infected grapevines, validating multispectral/ hyperspectral technology as a potential tool for the early detection of FD or other grapevine-associated diseases.