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…

Soil, vine, climate change – what is observed – what is expected

To evaluate the current and future impact of climate change on Viticulture requires an integrated view on a complex interacting system within the soil-plant-atmospheric continuum under continuous change. Aside of the globally observed increase in temperature in basically all viticulture regions for at least four decades, we observe several clear trends at the regional level in the ratio of precipitation to potential evapotranspiration. Additionally the recently published 6th assessment report of the IPCC (The physical science basis) shows case-dependent further expected shifts in climate patterns which will have substantial impacts on the way we will conduct viticulture in the decades to come.
Looking beyond climate developments, we observe rising temperatures in the upper soil layers which will have an impact on the distribution of microbial populations, the decay rate of organic matter or the storage capacity for carbon, thus affecting the emission of greenhouse gases (GHGs) and the viscosity of water in the soil-plant pathway, altering the transport of water. If the upper soil layers dry out faster due to less rainfall and/or increased evapotranspiration driven by higher temperatures, the spectral reflection properties of bare soil change and the transport of latent heat into the fruiting zone is increased putting a higher temperature load on the fruit. Interactions between micro-organisms in the rhizosphere and the grapevine root system are poorly understood but respond to environmental factors (such as increased soil temperatures) and the plant material (rootstock for instance), respectively the cultivation system (for example bio-organic versus conventional). This adds to an extremely complex system to manage in terms of increased resilience, adaptation to and even mitigation of climate change. Nevertheless, taken as a whole, effects on the individual expressions of wines with a given origin, seem highly likely to become more apparent.

Amino nitrogen content in grapes: the impact of crop limitation

As an essential element for grapevine development and yield, nitrogen is also involved in the winemaking process and largely affects wine composition. Grape must amino nitrogen deficiency affects the alcoholic fermentation kinetics and alters the development of wine aroma precursors. It is therefore essential to control and optimize nitrogen use efficiency by the plant to guarantee suitable grape nitrogen composition at harvest. Understanding the impact of environmental conditions and cultural practices on the plant nitrogen metabolism would allow us to better orientate our technical choices with the objective of quality and sustainability (less inputs, higher efficiency). This trial focuses on the impact of crop limitation – that is a common practice in European viticulture – on nitrogen distribution in the plant and particularly on grape nitrogen composition. A wide gradient of crop load was set up in a homogeneous plot of Chasselas (Vitis vinifera) in the experimental vineyard of Agroscope, Switzerland. Dry weight and nitrogen dynamics were monitored in the roots, trunk, canopy and grapes, during two consecutive years, using a 15N-labeling method. Grape amino nitrogen content was assessed in both years, at veraison and at harvest. The close relationship between fruits and roots in the maintenance of plant nitrogen balance was highlighted. Interestingly, grape nitrogen concentration remained unchanged regardless of crop load to the detriment of the growth and nitrogen content of the roots. Meanwhile, the size and the nitrogen concentration of the canopy were not affected. Leaf gas exchange rates were reduced in response to lower yield conditions, reducing carbon and nitrogen assimilation and increasing intrinsic water use efficiency. The must amino nitrogen profiles could be discriminated as a function of crop load. These findings demonstrate the impact of plant balance on grape nitrogen composition and contribute to the improvement of predictive models and sustainable cultural practices in perennial crops.

Use of a new, miniaturized, low-cost spectral sensor to estimate and map the vineyard water status from a mobile 

Optimizing the use of water and improving irrigation strategies has become increasingly important in most winegrowing countries due to the consequences of climate change, which are leading to more frequent droughts, heat waves, or alteration of precipitation patterns. Optimized irrigation scheduling can only be based on a reliable knowledge of the vineyard water status.

In this context, this work aims at the development of a novel methodology, using a contactless, miniaturized, low-cost NIR spectral tool to monitor (on-the-go) the vineyard water status variability. On-the-go spectral measurements were acquired in the vineyard using a NIR micro spectrometer, operating in the 900–1900 nm spectral range, from a ground vehicle moving at 3 km/h. Spectral measurements were collected on the northeast side of the canopy across four different dates (July 8th, 14th, 21st and August 12th) during 2021 season in a commercial vineyard (3 ha). Grapevines of Vitis vinifera L. Graciano planted on a VSP trellis were monitored at solar noon using stem water potential (Ψs) as reference indicators of plant water status. In total, 108 measurements of Ψs were taken (27 vines per date).

Calibration and prediction models were performed using Partial Least Squares (PLS) regression. The best prediction models for grapevine water status yielded a determination coefficient of cross-validation (r2cv) of 0.67 and a root mean square error of cross-validation (RMSEcv) of 0.131 MPa. This predictive model was employed to map the spatial variability of the vineyard water status and provided useful, practical information towards the implementation of appropriate irrigation strategies. The outcomes presented in this work show the great potential of this low-cost methodology to assess the vineyard stem water potential and its spatial variability in a commercial vineyard.

Anthocyanin profile is differentially affected by high temperature, elevated CO2 and water deficit in Tempranillo (Vitis vinifera L.) clones

Anthocyanin potential of grape berries is an important quality factor in wine production. Anthocyanin concentration and profile differ among varieties but it also depends on the environmental conditions, which are expected to be greatly modified by climate change in the future. These modifications may significantly modify the biochemical composition of berries at harvest, and thus wine typicity. Among the diverse approaches proposed to reduce the potential negative effects that climate change may have on grape quality, genetic diversity among clones can represent a source of potential candidates to select better adapted plant material for future climatic conditions. The effects of individual and combined factors associated to climate change (increase of temperature, rise of air CO2 concentration and water deficit) on the anthocyanin profile of different clones of Tempranillo that differ in the length of their reproductive cycle were studied. The aim was to highlight those clones more adapted to maintain specific Tempranillo typicity in the future. Fruit-bearing cuttings were grown in controlled conditions under two temperatures (ambient temperature versus ambient temperature + 4ºC), two CO2 levels (400 ppm versus 700 ppm) and two water regimes (well-watered versus water deficit), both in combination or independently, in order to simulate future climate change scenarios. Elevated temperature increased anthocyanin acylation, whereas elevated CO2 and water deficit favoured the accumulation of malvidin derivatives, as well as the acylation and tri-hydroxylation level of anthocyanins. Although the changes in anthocyanin profile observed followed a common pattern among clones, such impact of environmental conditions was especially noticeable in one of the most widely distributed Tempranillo clones, the accession RJ43.

Water deficit differentially impacts the performances and the accumulation of grape metabolites of new varieties tolerant to fungi

The use of resistant varieties is a long-term but promising solution to reduce chemical input in viticulture. Several important breeding programs in Europe and abroad are now releasing a range of new hybrids performing well regarding fungi susceptibility and producing good quality wines. Unfortunately, insufficient attention is paid by the breeders to the adaptation of these varieties to climatic changes, notably to the increased climatic demand and water deficit (WD). Thus, prior to the adoption of such varieties by the wine industry in Mediterranean regions, there is a need to consider their suitability to WD. This study aimed to characterize the different drought-strategies adopted by 6 new resistant varieties selected by INRAE in comparison to Syrah. To allow the assessment of long-term impacts of WD, field-grown vines were exposed to contrasted WD from 2018 to 2021 under a semi-arid Mediterranean climate. A gradient of WD was applied in the field and controlled through plant measurements at the single plant level. Grape development was non-destructively monitored to determine the arrest of berry phloem unloading. The impacts of WD on berry composition, including water, primary metabolites (sugars, organic acids), secondary metabolites (anthocyanins, thiols precursors) and main cations contents, were assessed at this specific stage. Results showed different varietal responses during the year and inter-annual acclimation in terms of plant water use efficiency, biomass accumulation, as well as yield components and berry composition. WD differentially reduced the accumulation of primary metabolites at plant and berry levels, but it little changed their concentrations in the fruits at the ripe stage. Moreover, WD differentially impacted the accumulation of secondary metabolites and major cations between the varieties. In the talk, we’ll present the main results regarding the WD impacts on fruit metabolites and enlarge the reflection about the practical assessment of the grapevine acclimation to WD.