OENO IVAS 2019 banner
IVES 9 IVES Conference Series 9 OENO IVAS 9 OENO IVAS 2019 9 Analytical developments from grape to wine, spirits : omics, chemometrics approaches… 9 Molecular characterization of wines nucleophilic potential by ultra-performance liquid chromatography high resolution mass spectrometry

Molecular characterization of wines nucleophilic potential by ultra-performance liquid chromatography high resolution mass spectrometry


The knowledge about the molecular fraction associated to white wines oxidative stability is still poorly understood. However, the role of S- N- congaing compounds, like glutathione (GSH) and other peptides, as a source of reductant in many oxidation reactions protecting against heavy metals toxicity, or lipids and polyphenols oxidation as ROS-scavenger is today very well established. GSH is also reported being an important antioxidant, reacting as nucleophile substance that conjugates straightforwardly with reactive electrophiles resulting in foods and beverages chemical oxidative stability. It has been shown that, GSH efficiency against wines sensory oxidative stability is related to wines antioxidant metabolome consisting of N- and S- containing compounds like amino acids, aromatic compounds and peptides. These compounds present a strong nucleophilic character and their reactivity with wines electrophiles such as oxidized polyphenols, suggests the formation of stable adducts presenting lower oxidative potential. We consider that the knowledge behind the chemical composition of wines antioxidant metabolome is a key factor to estimate wines aging potential. 

In that respect, the present study introduces an original determination of the pool of nucleophilic compounds that can react with quinones in wine acidic conditions. One step derivatization of nucleophiles has been realized in wines with no pH adjustment by using 4‑methyl‑1,2‑benzoquinone (Q) as a nucleophilic probe. LC‑MS‑QToF analysis of 92 white followed by Multivariate analysis (PLS‑DA) and Wilcoxon test allowed to isolate up to 141 putative nucleophilic compounds. Only 20 of these compounds were detected without derivatization, showing an increase in detection level by quinone trapping, especially for thiols. Moreover, annotation using online database (Oligonet, Metlin and KEGG) as well as elementary formula determined by isotopic profile and MS² analysis allowed to show an important proportion of amino acids and peptides and to identify 4 compounds (GSH, Cys, homocysteine and Pro). The majority of the putative peptides can contain amino acids that are known to have antioxidant properties (Val, Leu, Ile, Pro, Trp, Cys and Met). 


These results show that derivatization of wines using Q allows to enhance thiol detection levels and to determine a pool of untargeted nucleophilic compounds that can be part of wines antioxidant metabolome


Publication date: June 19, 2020

Issue: OENO IVAS 2019

Type: Article


Remy Romanet, Florian Bahut, Maria Nikolantonaki, Regis Gougeon

Univ. Bourgogne Franche-Comté, AgroSup Dijon, PAM UMR A 02.102, Institut Universitaire de la Vigne et du Vin, Jules Guyot, 21000 Dijon, France

Contact the author


LC-QToF-MS, Nucleophilic compounds, Untargeted analysis, White wines oxidative stability 


IVES Conference Series | OENO IVAS 2019


Related articles…

Impact of some agronomic practices on grape skins anthocyanin content

Wine colour is the first quality characteristic to be assessed, especially regarding red wines. Anthocyanins are very well known to be the main responsible compounds for red wine colour. Red cultivars can synthesize and accumulate anthocyanins in berry skin to express their colour. However, anthocyanin accumulation is often influenced by a series of factors, such as genetic regulation, phytohormones, environmental conditions and viticultural management.

A geologic numeric mapping, with geophysic transects, of Marsannay’s vineyard (Burgundy, France)

Marsannay est l’appellation la plus septentrionale de la Côte de Nuits, à la limite Sud de Dijon. Elle regroupe trois villages, Chenôve, Marsannay-la-Côte et Couchey, et constitue l’appellation la plus vaste de la Côte de Nuits avec 315 hectares en A.O.C. Elle possède uniquement des niveaux d’appellations régionales et communales depuis 1987.

Facteurs physiques et biologiques affectant la production viticole et vinicole de la région avec dénomination d’origine “Condado de Huelva” (SW d’Espagne)

Les facteurs physiques et biologiques du milieu naturel affectant la production viticole de la R.D.O. “Condado de Huelva” et quelques relations les concernant sont étudiés dans les systèmes de la production vinicole ; le bon fonctionnement du Vignoble ayant besoin par ailleurs, du concours d’autres facteurs (Reynier, 1989 ; Paneque et al., 1996, a,b).

Soil electrical resistivity, a new and revealing technique for precision viticulture

High resolution spatial information of soil electrical resistivity (ER) was gathered to assess the spatial variability patterns of vegetative growth of two commercial vineyards (Vitis vinifera L. cv.

The albarizas and the viticultural zoning of Jerez­-Xérès-Sherry and Manzanilla-Sanlúcar de Barrameda registered apellations of origin (Cadiz, Spain)

Le terme ”Albariza” (du latin “albus“, blanc) déterminait à l’origine un type particulier du terrain calcaire, mais à présent il sert aussi à définir les sols et la bibliographie géologique actuelle le cite également pour de roches sédimentaires originaires du Neogene Betic.