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…

USE OF COLD LIQUID STABULATION AS AN OENOLOGICAL TECHNIQUE IN WHITE WINEMAKING: EFFECTS ON PHENOLIC, AROMATIC AND SENSORIAL COMPOSITION

The application of different winemaking techniques helps to modify the basic parameters, phenolic profile, and aroma components influencing the final wine quality. In particular, pre-fermentative processes aim to increase the extraction and preservation of grape native compounds. Among them, cold liquid stabulation (macération sur bourbes) consists in maintaining the grape juice on its lees, in suspended condition at low temperature (0-8 °C) for a variable time (generally from 7 to 21 days). The aim of this work is to apply the cold liquid stabulation on two Italian white grape varieties, Arneis and Cortese, to evaluate the impact on basic parameters, color, polyphenolic compounds (TPI), antioxidant power (DPPH), total polysaccharides, and free and glycosylated volatile compounds (GC-MS analysis) during and after the process.

EXPLORING RED WINE TYPICITY OF CORBIÈRES: EVALUATION OF THE DEGREE OF IMPACT OF VINIFICATION PROCESS ON THE CHEMICAL COMPOSITION AND ORGANOLEPTIC PROPERTIES OF WINES FROM DIFFERENT TERROIR

It is important nowadays for wine producers to create a product that is an expression of their terroir, a concept including the interaction between a place (topography, climate, soil), the people (tradition, winemaking and viticultural practices) and the resulting product (grape varieties, wines) [1]. Nonetheless, wine’s typicity linked to those terroirs must be easily recognizable by consumers thanks to distinctive sensory characters and composition [2]. Among the compounds of interest, aromatic compounds and polyphenols play an important role in the quality of red wines, by impacting on the odour, color and astringency. To explore the influence of terroir factors, including climate, soil and human practices, on the chemical and sensory profile of wines, red wines from five terroirs of the Corbières appellation were subjected to a general study approach.

EFFECT OF OXIDATION ON LOW MOLECULAR WEIGHT PHENOLIC FRACTION, SALIVARY PROTEINS PRECIPITATION AND ASTRINGENCY SUBQUALITIES OF RED WINES

Changes in the low molecular weight phenolic fraction, obtained by liquid-liquid microextraction technique, were studied after controlled oxidation of two typologies of Sangiovese wines (Brunello di Montalcino and Chianti Classico) belonging to two vintages (2017 and 2018). The fractions were characterized by LC-MS and quantified by HPLC. The most abundant extracted compounds were the phenolic acids. The effect of oxidation, vintage, and wine typology was stated by a three-ways ANOVA. Gallic and syringic acids significantly increased after oxidation while (–)-epicatechin decreased the most.

EVALUATION OF INDIGENOUS CANADIAN YEAST STRAINS AS WINE STARTER CULTURES ON PILOT SCALE FERMENTATIONS

The interactions between geographical and biotic factors, along with the winemaking process, influence the composition and sensorial characteristics of wine¹. In addition to the primary end products of alcoholic fermentation, many secondary metabolites contribute to wine flavor and aroma and their production depends predominantly on the yeast strain carrying out the fermentation. Commercially available strains of S. cerevisiae help improve the reproducibility and predictability of wine quality. However, most commercial wine strains available on the market have been isolated from Europe, are genetically similar, and may not be the ideal strain to reflect the terroir of Canadian vineyards².

EVALUATION OF INDIGENOUS SACCHAROMYCES CEREVISIAE ISOLATES FOR THEIR POTENTIAL USE AS FERMENTATION STARTERS IN ASSYRTIKO WINE

Assyrtiko is a rare ancient grape variety that constitutes one of the most popular in Greece. The objective of the current research was to evaluate indigenous Saccharomyces cerevisiae isolates as fermentation starters and also test the possible strain impact on volatile profile of Assyrtiko wine. 163 S. cerevisiae isolates, which were previously selected from spontaneous alcoholic fermentation, were identified at strain level by interdelta-PCR genomic fingerprinting. Yeasts strains were examined for their fermentative capacity in laboratory scale fermentation on pasteurized Assyrtiko grape must.