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…

Mobile device to induce heat-stress on grapevine berries

Studying heat stress response of grapevine berries in the field often relies on weather conditions during the growing season. We constructed a mobile heating device, able to induce controlled heat stress on grapes in vineyards. The heater consisted of six 150 W infrared lamps mounted in a profile frame. Heating power of the lamps could be controlled individually by a control unit consisting of a single board computer and six temperature sensors to reach a pre-set temperature. The heat energy applied to individual berries within a cluster decreases by the squared distance to the heat source, enabling the establishment of temperature profiles within individual clusters. These profiles can be measured by infrared thermography once a steady state has been reached. Radiant flux density received by a berry depending on the distance was calculated based on a view factor and measured lamp surface temperature and resulted to 665 Wm-2 at 7cm. Infrared thermography of the fruit surface was in good agreement with measurements conducted with a thermocouple inserted at epidermis level. In combination with infrared thermography, the presented device offers possibilities for a wide range of applications like phenotyping for heat tolerance in the field to proceed in the understanding of the complex response of plants to heat stress. Sunburn necrosis symptoms were artificially induced with the aid of the device for cv. Bacchus and cv. Sylvaner in the 2020 and 2021 growing season. Threshold temperatures for sunburn induction (LT5030min) were derived from temperature data of single berries and visual sunburn assessment, applying logistic regression. A comparison of threshold temperatures for the occurrence of sunburn necrosis confirmed the higher susceptibility of cv. Bacchus. The lower susceptibility of cv. Sylvaner did not seem to be related to its phenolic composition, rendering a thermoprotective role of berry phenolic compounds unlikely.

Characterization of variety-specific changes in bulk stomatal conductance in response to changes in atmospheric demand and drought stress

In wine growing regions around the world, climate change has the potential to affect vine transpiration and overall vineyard water use due to related changes in atmospheric demand and soil water deficits. Grapevines control their transpiration in response to a changing environment by regulating conductance of water through the soil-plant-atmosphere continuum. Most vineyard water use models currently estimate vine transpiration by applying generic crop coefficients to estimates of reference evapotranspiration, but this does not account for changes in vine conductance associated with water stress, nor differences thought to exist between varieties. The response of bulk stomatal conductance to daily weather variability and seasonal drought stress was studied on Cabernet-Sauvignon, Merlot, Tempranillo, Ugni blanc, and Semillon vines in a non-irrigated vineyard in Bordeaux France. Whole vine sap flow, temperature and humidity in the vine canopy, and net radiation absorbed by the vine canopy were measured on 15-minute intervals from early July through mid-September 2020, together with periodic measurement of leaf area, canopy porosity, and predawn leaf water potential. From this data, bulk stomatal conductance was calculated on 15-minute intervals, and multiple regression analysis was performed to identify key variables and their relative effect on conductance. Attention was focused on addressing multicollinearity and time-dependency in the explanatory variables and developing regression models that were readily interpretable. Variability of vapor pressure deficit over the day, and predawn water potential over the season explained much of the variability in conductance, with relative differences in response coefficients observed across the five varieties. By characterizing this conductance response, the dynamics of vine transpiration can be better parameterized in vineyard water use modeling of current and future climate scenarios.

Better understand the soil wet bulb formation with subsurface or aerial drip irrigation in viticulture

The gradual change in rainfall patterns experienced in the south of France vineyards, especially around the Mediterranean sea, means that the vines are increasingly subject to summer drought. The winegrowers developped the use of irrigation techniques to ensure the maintenance of competitive yields in the production of wines under Protected Geographical Indication label. In practice, drip irrigation pipes can be installed above the ground or buried into the soil as well as at different distances from the vine row. The objective of this study was to examine the profiles of the wet bulbs of the soil obtained from two drip irrigation systems : aerial drip located under the vine row and subsurface drip placed in the middle of the inter-row. This experiment took place over two consecutive seasons (2020-2021) on a 3.4 ha Viognier plot in the Mediterranean region (PGI Oc, France) on sandy clay soil. The annual rainfalls were less than 400 mm. Soil water content probes were installed at different depths (20 – 40 – 60 – 80 cm) and at different lateralities from the vine row (30 – 60 – 90 – 120 cm) to control the formation of the soil wet bulb during irrigation. The mapping and the analysis of the data allowed a better understanding and differentiation of the water percolation when irrigating with subsurface or aerial drip. For the same amount of water and without differences of vine water status, it is shown that in a subsurface drip irrigation situation, the size of the wet bulb formed is larger than in aerial drip irrigation system.

Projected changes in vine phenology of two varieties with different thermal requirements cultivated in La Mancha DO (Spain) under climate change scenarios

The aim of this work was to analyze the phenology variability of Tempranillo and Chardonnay cultivars, related to the climatic characteristics in La Mancha Designation of Origin, and their potential changes under climate change scenarios. Phenological dates referred to budbreak, flowering, veraison and harvest were analyzed for the period 2000-2019. The weather conditions at daily time scale, recorded during the same period, were also evaluated. The thermal requirements to reach each of these phenological stages were calculated and expressed as the GDD accumulated from DOY=60. Changes in phenology were projected by 2050 and 2070 taking into account those values and the projected temperatures and precipitation, simulated under two Representative Concentration Pathway (RCP) scenarios –RCP4.5 and RCP8.5– using an ensemble of models. The average phenological dates during the period under study were, April 16th ± 6.6 days and April 5th ± 6.0 days for budbreak, May 31st ± 6.0 days and May 27th ± 5.3 days for flowering, July 26th ± 5.6 days and July 25th ± 5.8 days for veraison, and Ago 23rd ± 10.8 days and Ago 17th ± 9.0 days for harvest, respectively, for Tempranillo and Chardonnay. The projected changes in temperature imply an average change in the maximum growing season (April-August) temperatures of 1.2 and 1.9°C by 2050, and 1.6 and 2.6°C by 2070, under the RCP4.5 and RCP8.5 scenarios, respectively. A reduction in precipitation is predicted, which vary between 15% for 2050 under RCP4.5 scenario and up to 30% by 2070 under RCP8.5. The advance of the phenological dates for 2050, could be of 6, 7, 7, and 8 days for Tempranillo and 4, 6, 6 and 9 days for Chardonnay, respectively for budbreak, flowering, veraison and harvest under the RCP4.5 scenario. Under the RCP8.5 emission scenario, the advance could be up to 30% higher.

Phenolic composition of Tempranillo Blanco grapes changes after foliar application of urea

Our research aimed to determine the effect and efficiency of foliar application of urea on the phenolic composition of Tempranillo Blanco grapes. The field experiment was carried out in 2019 and 2020 seasons and the plot was located in D.O.Ca Rioja (North of Spain). The vineyard was Vitis vinifera L. Tempranillo Blanco and grafted on Richter-110 rootstock. The treatments were control (C), whose plants were sprayed with water and three doses of urea: plants were sprayed with urea 3 kg N/ha (U3), 6 kg N/ha (U6) and 9 kg N/ha (U9). The applications were performed in two phenological stages, pre-veraison (Pre) and veraison (Ver). Also, each of the treatments was repeated one week later. Control and treatments were performed in triplicate and arranged in a randomised block design. Grapes were harvested at optimum ripening stage. High-performance liquid chromatography was used to analyse the phenolic composition of the grapes. Finally, the results obtained from the analytical determinations – flavonols, flavanols and non-flavonoid (hydroxybenzoic acids, hydroxycinnamic acids and stilbenes) – were studied statistically by analysis of variance. The results showed that, in 2019, U6-Pre and U9-Pre treatments increased the hydroxybenzoic acid content in grapes, and also all foliar treatments applied at Pre enhanced the stilbene concentration. Moreover, U3-Ver was the only treatment that rose flavonol and stilbene contents in the Tempranillo Blanco grapes. In 2020, all treatments applied at Pre enhanced the flavonol concentration in grapes. Furthermore, U3-Pre and U9-Pre treatments increased stilbene content in grapes. Nevertheless, the hydroxybenzoic acid content was improved by U6-Ver and U9-Ver and besides, hydroxycinnamic acid concentration in grapes was increased by all treatments applied at Ver. In conclusion, the lower and highest dose of urea (U3 and U9), applied at pre-veraison, were the best treatments to improve the Tempranillo Blanco grape phenolic composition.