terclim by ICS banner
IVES 9 IVES Conference Series 9 UNRAVELING THE CHEMICAL MECHANISM OF MND FORMATION IN RED WINE DURING BOTTLE AGING : IDENTIFICATION OF A NEW GLUCOSYLATED HYDROXYKETONE PRO-PRECURSOR

UNRAVELING THE CHEMICAL MECHANISM OF MND FORMATION IN RED WINE DURING BOTTLE AGING : IDENTIFICATION OF A NEW GLUCOSYLATED HYDROXYKETONE PRO-PRECURSOR

Abstract

During bottle aging, the development of wine aroma through low and gradual oxygen exposure is often positive in red wines, but can be unfavorable in many cases, resulting in a rapid loss of fresh, fruity flavors. Prematurely aged wines are marked by intense prune and fig aromatic nuances that dominate the desirable bouquet achieved through aging (Pons et al., 2013). This aromatic defect, in part, is caused by the presence of 3-methyl-2,4-nonanedione (MND). MND content was shown to be lower in nonoxidized red wines and higher in oxidized red wines, which systematically exceeds the odor detection threshold (62 ng/L). Concentrations up to 340 ng/L were evidenced in the most oxidized red wines as well as MND content up scaling was observed whatever the oxidation level. Very recently, we identified two new hydroxyketones (2-hydroxy-3-methylnonan-4-one) associated with MND distribution in aged red wines. We demonstrated that in red wine, their oxidation can produce MND (Peterson et al., 2020). To date, the origin of these precursors were not studied. During preliminary experiments, the presence in wine of a glycosylated form of this hydroxyketone was suggested by hydrolysis experiments. Based on the literature, we hypothesized the presence of a corresponding glucosylated precursor and developed a strategy for its organic multi-step synthesis. First, the MND hydroxylated precursor of MND was synthesized by aldolization (Crévisy et al., 2001). Then, based on literature, we optimized strategies for the O- glycosidation step. For this, the tetrabenzylated glucose was activated by imidation reaction (Chatterjee et al., 2018). Several deprotection methods for the glucoside moiety were then experimented. Finally, the use of palladium on carbon for the hydrogenolytic debenzylation lead to the target compound. A multi-step purification process (LC, HPLC) was carried out to reach sufficient purity. Glycosylated standard was characterized by Nuclear Magnetic Resonance (NMR) and by High Resolution Mass Spectrometry (HRMS) and then used to develop an LC-MS/MS for its identification in grapes and wines. The first analytical results lead to look deeper into the search for glucosylated compounds in various oenolo-gical samples (grapes, musts, red wines), affected or not by the nuances of “dried fruits”.

 

1. Peterson, A.; Cholet, C.; Geny, L.; Darriet, P.; Landais, Y.; Pons, A. Identification and analysis of new α- and β-hydroxy ketones related to the formation of 3-methyl-2,4-nonanedione in Musts and red wines. Food Chem. 2020, 305, 12548.
2. Pons, A.; Lavigne, V.; Darriet, P.; Dubourdieu, D. Role of 3-methyl-2,4-nonanedione in the flavor of aged red wines. J. Agric. Food Chem. 2013, 61 (30), 7373–7380.
3. Crévisy, C.; Wietrich, M.; Le Boulaire, V.; Uma, R.; Grée, R. From allylic alcohols to aldols via a novel, tandem isomerization–condensation catalyzed by Fe(CO)5. Tetrahedron Lett. 2001, 42 (3), 395–398.
4. Chatterjee, S.; Moon, S.; Hentschel, F.; Gilmore, K.; Seeberger, PH. An Empirical Understanding of the Glycosylation Reaction. J Am Chem Soc. 2018, 140 (38), 11942-11953.

DOI:

Publication date: February 9, 2024

Issue: OENO Macrowine 2023

Type: Poster

Authors

D. Lamliji1,2,3, C. Thibon2,3, S. Shinkaruk1,2,3, A. Pons2,3,4
1. Univ. Bordeaux, CNRS, Bordeaux INP, ISM, UMR 5255, F-33400 Talence, France.
2. Univ. Bordeaux, Bordeaux INP, INRAE, OENO, UMR 1366, ISVV, F-33140 Villenave d’Ornon, France.
3. Bordeaux Sciences Agro, Bordeaux INP, INRAE, OENO, UMR 1366, ISVV, F-33170 Gradignan, France.
4. Seguin Moreau France, Z.I. Merpins, BP 94, 16103 Cognac, France.

Contact the author*

Keywords

cooked fruit aroma, 3-methyl-2,4-nonanedione, glucosylated precursors, identification

Tags

IVES Conference Series | oeno macrowine 2023 | oeno-macrowine

Citation

Related articles…

HOW DO ROOTSTOCKS AFFECT CABERNET SAUVIGNON AROMATIC EXPRESSION?

Grape quality potential for wine production is strongly influenced by environmental parameters such as climate and agronomic factors such as rootstock. Several studies underline the effect of rootstock on vegetative growth of the scions [1] and on berry composition [2, 3] with an impact on wine quality. Rootstocks are promising agronomic tools for climate change adaptation and in most grape-growing regions the potential diversity of rootstocks is not fully used and only a few genotypes are planted. Little is known about the effect of rootstock genetic variability on the aromatic composition in wines; thus further investigations are needed.

THE ROLE OF CELL WALL POLYSACCHARIDES IN THE EXTRACTION OF ANTHOCYANINS AND TANNINS: RESULTS, PERSPECTIVES OF A MORE POSITIVE CONTRIBUTION

The composition of grape berry cell walls was studied on two grape varieties, two years and two maturation levels at the same time as the extraction of anthocyanins and tannins. The chemical composition of skins, seeds, and pulps, focused on polyphenols and polysaccharides, was compared to the chemical composition in polyphenols after extraction from the skins in model solutions or after wine making of the berries. Polyphenols were mainly characterized by UPLC-MS and HPLC-SEC. Polysaccharides were characterized by analysis of the neutral sugar compositions, and also by the CoMPP (comprehensive micropolymer profiling) analysis, a new method which targets the functional groups of cell wall polysaccharides.

YEAST DERIVATIVE PRODUCTS: CHARACTERIZATION AND IMPACT ON RIBOFLAVIN RELEASE DURING THE ALCOHOLIC FERMENTATION

Light-struck taste (LST) is a wine fault that can occur in white and sparkling wines when exposed to light. This defect is mainly associated to the formation of methanethiol and dimethyl disulfide due to light-induced reactions involving riboflavin (RF) and methionine [1]. The presence of RF in wine is mainly due to the metabolism of yeast [2] which fermenting activity can be favoured by using yeast derivative products (YDPs) as nutrients. Nonetheless, a previous study showed the addition of YDPs before the alcoholic fermentation (AF) led to higher concentrations of RF in wines [3]. Due to the widespread use of YDPs in the winemaking process, this study aimed to understand the possible relation between the content of RF in wine and the YDP adopted as nutrient for AF.

INFLUENCE OF THE NITROGEN / LIPIDS RATIO OF MUSTS ON THE REVELATION OF AROMATIC COMPOUNDS IN SAUVIGNON BLANC WINE

Production of volatile compounds by yeast is known to be modulated by must nitrogen. Nevertheless, various parameter of must quality have an impact on yeast fermentation. In this study we propose to evaluate the impact of nitrogen / lipids balance on a Sauvignon Blanc grape juice (Val de Loire).
Must was prepared from the same grapes at pilot scale. Three modalities were carried out: direct pressing, direct pressing with a pre-fermentation cold stabulation and pellicular maceration before pressing.

FLOW CYTOMETRY, A POWERFUL AND SUSTAINABLE METHOD WITH MULTIPLE APPLICATIONS IN ENOLOGY

Flow cytometry (FCM) is a powerful technique allowing the detection, characterization and quantification of microbial populations in different fields of application (medical environment, food industry, enology, etc.). Depending on the fluorescent markers and specific probes used, FCM provides information on the physiological state of the cell and allows the quantification of a microorganism of interest within a mixed population. For 15 years, the enological sector has shown growing interest in this technique, which is now used to determine the populations present (of interest or spoilage) and the physiological state of microorganisms at the different stages of winemaking.