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…

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.

ASSESSING THE ROLE OF 27 KNOWN BITTER COMPOUNDS IN COMMERCIAL WHITE WINES COMBINING LC-MS QUANTIFICATION AND SENSORY ANALYSIS

The balance between the different flavours of a wine largely determines its perception and appreciation by the consumers. In white wines, sweetness and sourness are usually the two poles balancing the taste properties. The bitter flavour, on the other hand, is frequently associated with a loss of equilibrium and all white wines (dry and sweet, young and aged) are affected.
Several bitter compounds are already well-described in wines.

NEW PLANT BIOPOLYMERS FOR THE COLLOIDAL STABILITY OF THE COLORING MATTER OF RED WINES

The color as well as the “clarity” of red wines are ones of the qualities required by the consumers. Red wines must have colloidal stability from its bottling to its consumption. The supplementation of red wines with additives, and especially Acacia senegal gum, contributes to its organoleptic properties such as the colloidal stabilization of the coloring matter. In a global perspective of limitation of additives in the field of enology, one of the objectives is notably (i) to reduce the use of additives in wines, by their number and/or their quantity, and (ii) to favor the use of natural additives while preserving the organoleptic and sensory qualities of wines.

Influence of agrophotovoltaic on vine and must in a cool climate

The current energy crisis means that interest in agrophotovoltaics has increased significantly. The reason behind this is that the system aims to combine agricultural production with energy production. During the three-year period from 2020 to 2022, the effects of photovoltaic panels on the vine, the yield and the quality of the must were studied in Walenstadt in northern Switzerland, an area with a cool, humid climate. 65 Pinot noir vines were planted in the 160m2 study area. Because of the large edge effects, only 3 repetitions with 4 vines each could be created. A significantly lower leaf infestation by Plasmopara viticola was observed among the panels in each of the three years.

THE FLAVANOL PROFILE OF SKIN, SEED, WINES, AND POMACE ARE CHARACTERISTIC OF EACH TYPOLOGY AND CONTRIBUTES TO UNDERSTAND THE FLAVAN- 3-OLS EXTRACTION DURING RED WINEMAKING

Wine flavanols are extracted from grape skin and seeds along red winemaking. Potentially, eight flavan-3-ol subunits may be present as monomers or as tannins constituents, being these catechin, epicathechin, gallocatechin, epigallocatechin end the gallates of the mentioned units. In this work the flavanol profiles of grape skins and seeds before (grapes) and after (pomace) red winemaking were studied together with the one in the corresponding wines. The trials were made over two vintages in Vitis vinifera cv. Tannat, Syrah and Marselan from Uruguay.