OENO IVAS 2019 banner
IVES 9 IVES Conference Series 9 OENO IVAS 9 OENO IVAS 2019 9 Chemical and Biochemical reactions, including grape and wines microorganisms impact 9 When organic chemistry contributes to the understanding of metabolism mechanisms

When organic chemistry contributes to the understanding of metabolism mechanisms

Abstract

Many compounds of interest in wine are difficult to analyze since they are present in very small quantities or they are unstable. The need for reliable data led scientists to develop complex method in order to overcome the analytical difficulties and provide accurate quantitative data for grape or wine characterization.

For 10 years, we developed several chemical strategies to obtain analytical standards either as labelled analogues or as diastereomers to develop SIDA and DIDA analytical methods, respectively. These quantification methods afforded accurate and reliable results by suppressing analytical bias due to sample preparation. Several examples will be presented from deuterated analogues: varietal thiols [1], thiol precursors [2], Ochratoxin A [3], and diastereoisomers: Ochratoxin A [4] and hydroxycinnamic acids [5].

Another interesting application based on synthetic compounds lies in their possible exploitation as tracers. Indeed, the scale-up and optimization of chemical syntheses from μg to mg levels provided us with substantial amounts of molecules that could be used in metabolism studies. For example, we recently used labelled thiol precursors as tracers in Sauvignon Blanc musts for metabolism studies. Degradation of such tracers was monitored to highlight several key interconversion mechanisms and bring new elements in varietal thiol biogenesis knowledge [6]. In these applications, the choice of the labelling position (for Ochratoxin A for instance) or multilabelling possibilies (for thiol precursors) offer future opportunity to investigate detoxification process or to obtain insight in the metabolism of aroma precursors, respectively.

References

1. a) A. Roland, R. Schneider, A. Razungles and F. Cavelier, Varietal thiols in wine: Discovery, Synthesis and Applications, Chem. Rev. 2011, 111, 7355. b) R. Schneider, Y. Kotseridis, J.-L. Ray, C. Augier and R.Baumes, Quantitative determination of sulfur-containing wine odorants at sub parts per billion levels.
2. Development and application of a stable isotope dilution assay, J. Agri. Food Chem., 2003, 51, 3243. 2. H.Bonnaffoux, A.Roland, E.Rémond, S.Delpech, R.Schneider, F.Cavelier, First identification and quantification of S-3- (hexan-1-ol)-γ-glutamyl-cysteine in grape must as a potential thiol precursor, using UPLC-MS/MS analysis and stable iso-tope dilution assay, Food Chem., 2017, 237, 877.
3. A.Bouisseau, A.Roland, R.Schneider and F.Cavelier, First Synthesis of a Stable Isotope of Ochratoxin A Metabolite for a Reliable Detoxification Monitoring, Org. Lett., 2013, 15, 3888.
4. A.Roland, P.Bros, A.Bouisseau, F.Cavelier and R.Schneider, Analysis of Ochratoxin A in musts and wines by LCMS/MS: Comparison of Stable Isotope Dilution Assay and Diastereomeric Dilution Assay Methods, Anal. Chim. Acta, 2014, 818, 39.
5. F. Cavelier, A. Roland, A. Bouisseau, J. Martinez, R. Schneider. Method for the esterification of polar molecules, WO 2015 011230
6. H. Bonnaffoux, S. Delpech, E. Rémond, R. Schneider, A. Roland, F. Cavelier, Revisiting the evaluation strategy of varietal thiol biogenesis, Food Chem., 2018, 268, 126.

DOI:

Publication date: June 19, 2020

Issue: OENO IVAS 2019

Type: Article

Authors

Florine Cavelier Hugo Bonnaffoux, Anaïs Bouisseau, Stéphane Delpech, Aurélie Roland, Rémi Schneider

Université de Montpellier (France)

Contact the author

Keywords

organic chemistry, analytical chemistry, internal standards, aroma

Tags

IVES Conference Series | OENO IVAS 2019

Citation

Related articles…

Assessment of climate change impacts on water needs and growing cycle on grapevine in three DOs of NE Spain

This study assessed the suitability of grapevine growing in three DOs (Empordà, Pla de Bages and Penedès) of Catalonia (NE Spain) over the 21st century. For this purpose, an estimation of water needs and agroclimatic and phenological indicators was made. Climate change impacts were estimated at 1 km pixel resolution using temperature and precipitation projections from several general circulation models (GCM) and two climate change scenarios: RCP 4.5 (stabilization scenario) and RCP 8.5 (worst-case scenario). Potential crop evapotranspiration (following FAO procedure) and a daily water balance considering soil water holding capacity were used to estimate actual evapotranspiration of vines and, finally, water needs. Dynamics would be similar in the three DOs studied although the magnitude of impact differs. Water needs would be 2 and 3 times greater (ranging from 0 to more than 1500 m3/ha) than current water needs at both climate change scenarios. Moreover, blooming date would advance from 3 to 6 weeks, harvest date from 1 to 2.5 months, resulting in growing cycles from 10 to 80 days shorter. It should also be noted that frost risk would decrease from 6 to 76%, the number of days with temperatures above 30ºC during ripening would rise from 48 to 500% and tropical nights (minimum temperature >20ºC) at ripening would increase from 28 to 150%, depending on the scenario and the DOs. The impacts of climate change in the three DOs could result in significant limitations for grapevine cultivation and wine production if adaptive strategies are not applied. This result could serve as a basis for the design of specific and particular adaptation strategies to improve and maintain vineyards in the DOs studied and could be extrapolated to similar DOs and regions.

Influence of agronomic practices in soil water content in mid-mountain vineyards

In the context of LIFE project MIDMACC (LIFE18 CCA/ES/001099), several pilots have been installed in vineyards in mid mountain areas of Catalonia (NE Spain) to test well stablished agronomic practices to increase the adaptation of Mediterranean mid mountain to climate change. Soil water content (SWC) at three different depths (15, 30 and 45cm) was measured in continuum from August 2020. One pilot (WC) included a well-established green cover (GC), a new GC (NC) and a conventional soil management (CM, tilling+herbicides). NC presented an intermediate state between WC and CM, responding similarly to CM in autumn but quickly reaching similar SWC to WC, then following the same evolution till next spring, with CM presenting lower values along autumn and winter. Then vegetation activation decreased SWC in all plots, (much slower in CM, lacking GC). Sensibility to spring rains is again intermediate for NC, which joins SWC evolution of CM by the end of spring till next autumn. It is expected that NC will resemble WC more and more as its GC develops. In the pilot combining vine training (VSP vs Gobelet) and hillside management (slope vs terrace), no clear pattern could be related with these conditions. However, both terraces seem to be more sensitive to spring rains. A third pilot included new vineyards (7 and 1 year old). In the new vineyard (N), higher canopy development, a spontaneous green cover and row straw resulted in a slower SWC dynamic, not so sensitive to rains but conserving more soil water in spring and most of summer, even with presumably a higher water extraction by vines. In the newest vineyard (VN) the deepest sensor is still sensitive to rain events all over the year and SWC is always highest at this depth, revealing small water capture by vines.

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.

The impact of leaf canopy management on eco-physiology, wood chemical properties and microbial communities in root, trunk and cordon of Riesling grapevines (Vitis vinifera L.)

In the last decades, climate change required already adaptation of vineyard management. Increase in temperature and unexpected weather events cause changes in all phenological stages requiring new management tools. For example, defoliation can be a useful tool to reduce the sugar content in the berries creating differences in the wine profiles. In a ten-year field experiment using Riesling (Vitis vinifera L, planted 1986, Geisenheim, Germany), various mechanical defoliation strategies and different intensities were trialed until 2016 before the vineyard was uprooted. Wood was sampled from the plant compartments root, trunk, cordon and shoot for analyses of physicochemical properties (e.g. lignin and element content, pH, diameter), nonstructural carbohydrates and the microbial communities. The aim of the study was to investigate the influence of reduced canopy leaf area on the sink-source allocation into different compartments and potential changes of the fungal and prokaryotic wood-inhabiting community using a metabarcoding approach. Severe summer pruning (SSP) of the canopy and mechanical defoliation (MDC) above the bunch zone decreased the leaf area by 50% compared to control (C). SSP reduced the photosynthetic capacity, which resulted in an altered source-sink allocation and carbohydrate storage. With lower leaf area, less carbohydrates are allocated. This for example resulted in a decreased trunk diameter. Further, it affected the composition of the grapevine wood microbiota. SSP and MDC management changed significantly the prokaryotic community composition in wood of the root samples, but had no effect in other compartments. In general, this study found strong compartment and less management effects of the microbial community composition and associated physicochemical properties. The highest microbial diversities were identified in the wood of the trunk, and several species were recorded the first time in grapevine.

Mechanisms involved in the heating of the environment by the aerodynamic action of a wind machine to protect a vineyard against spring frost

One of the main consequences of global warming is the rise of the mean temperature. Thus, the heat summation by the plants begins sooner in the early spring, and by cumulating growing degree-days, phenological development tends to happen earlier. However, spring frost is still a recurrent phenomenon causing serious damages to buds and therefore, threatening the harvests of the winegrowers. The wind machine is a solution to protect fruit crops against spring frost that is increasingly used. It is composed of a 10-m mast with a blowing fan at its peak. By tapping into the strength of the nocturnal thermal inversion, it sweeps the crop by propelling warm air above to the ground. Thus, stratification is momentarily suppressed. Furthermore, the continuous action of the machine, alone or in synergy, or the addition of a heater allow the bud to be bathed in a warmer environment. Also, the punctual action of the tower’s warm gust reaches the bud directly at each rotation period. All these actions allow the bud to continuously warm up, but with different intensities and over a different period. Although there is evidence of the effectiveness of the wind machines, the thermal transfers involved in those mechanisms raise questions about their true nature. Field measurements based on ultrasonic anemometers and fast responding thermocouples complemented by laboratory measurements on a reduced scale model allow to characterize both the airflow produced by the wind machine and the local temperature in its vicinity. Those experiments were realized in the vineyard of Quincy, in the framework of the SICTAG project. In the future paper, we will detail the aeraulic characterization of the wind machine and the thermal effects resulting from it and we will focus on how the wind machine warms up the local atmosphere and enables to reduce the freezing risk.