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…

Apoplastic pH influences Vitis vinifera Barbera recovery responses to short and prolonged drought 

Alteration of sap pH is one of the first chemical changes that occurs within the xylem vessels of plants exposed to drought. Xylem sap acidification accompanied by the accumulation of soluble sugars has been recently documented in several species (Sharp and Davis, 2009; Secchi and Zwieniecki, 2016). Here, Vitis vinifera plants of the anysohydric cultivar Barbera were exposed to either short (no irrigation; SD) or to prolonged drought (continual reduction of 10% water; PD). When comparable severe stress was reached, the potted grapes were re-watered. SD was characterized by fast (2–3 days) stomatal closure and high abscisic acid (ABA) accumulation in xylem sap (>400 μg L−1) and in leaf. In PD plants, the rise in ABA levels was considerably diminished.

Eléments importants d’une méthodologie de caractérisation des facteurs naturels du terroir, en relation avec la réponse de la vigne à travers le vin

The French viticultural appellation areas are the result of an empirical, historical and evolutionary selection which, generally, has consecrated a match between natural factors, grape varieties and viti-vinicultural practices. The notion of terroir is the main basis of the Appellation d’Origine Contrôlée in viticulture. It is based on the one hand on privileged natural factors and on the other hand on the know-how of the winegrowers; the whole allowing the production of a wine endowed with an authenticity and a sensory typicity. Wine-growing practices evolve according to progress in viticulture and oenology, while the natural factors of the terroir are much more stable, with the exception of the vintage. They therefore represent a fundamental pillar of the identity of an appellation vineyard.

New disease-resistant grapevine varieties response to drought under a semi-arid climate

In many regions, climate change leads to an increase in air temperature combined with a reduction of rainfall, intensifying climatic demand and water deficits (WD) (Cardell et al. 2019), which in turn may negatively impact grapevine development, yield and grape composition (Santos et al. 2020). In addition, climate change may also increase disease pressure, leading to further yield and quality losses, besides increasing costs due to increased vineyard spraying (Santos et al. 2020) and reducing viticulture acceptability by consumers (Guichard et al. 2017). Adopting new resistant varieties appears as a promising long-term solution to better manage vine protection, but unfortunately little is known regarding their behavior in front of WD.

Study of the evolution of tannins during wine aging by mass spectrometry monitoring of oxidation markers released after chemical depolymerization

Among the many compounds in wine, condensed tannins play an important role in the organoleptic properties of the products; they are partly responsible for astringency, bitterness and also contribute to the color. This research work aims to study the oxidation state of these bio-heteropolymers which is an important lock in the analysis of processed products in order to better control their quality. Indeed, their identification remains at present a challenge because of the large heterogeneity of their degrees of polymerization (DP) based on 4 monomers (epicatechin, catechin, epigallocatechin, epicatechin-3-O-gallate) thus multiplying the number of oxidation products.

Bioprospecting of native Metschnikowia pulcherrima strains for biocontrol and aroma enhancement in the wine production chain

Metschnikowia pulcherrima is a well-studied non-conventional oenological yeast due to its positive contributions to winemaking as a bioprotective agent and as an aroma-enhancing starter in sequential fermentations with Saccharomyces cerevisiae (Binati et al., 2023; Canonico et al., 2023).