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…

CHARACTERIZATION AND ANTIBACTERIAL ACTIVITY OF A POLYPHENOLIC EXTRACT OBTAINED BY GREEN SUPERCRITICAL CO₂ EXTRACTION FROM RED GRAPE POMACE

Upgrading wine industry solid wastes is considered as one of the main strategies to support the circular economy. Red grape pomaces constitute a rich source of polyphenols, which have been shown to possess antioxidant properties and to provide benefits for human and animal health. The objective of this work was to obtain and characterise polyphenolic extracts from red grape pomaces via green supercritical CO₂ extraction using ethanol as a co-solvent, and to evaluate their antibacterial activity against susceptible and multidrug-resistant Escherichia coli strains of animal intestinal origin.

Read More

VOLATILE COMPOUNDS AND SENSORY PROFILE OF NEBBIOLO RED WINES TREATED WITH WOOD FORMATS ALTERNATIVE TO BARRELS

In winemaking, the use of wood products alternative to barrels, has become a useful tool for the achievement of numerous oenological objectives, including the fast release of desirable volatile and polyphenolic compounds, colour stabilization, and important economic advantages if compared to the traditional barrel production. Among a huge array of variables, the wood format, the vinification protocol, especially the moment of the infusion of the woods and the exposed surface area of the alternative woods are of relevant significance, since they may influence the speed and intensity of the aroma transfer from the wood to the wine defining different sensory profiles.

Read More

OPTIMIZATION, VALIDATION AND APPLICATION OF THE EPR SPIN-TRAPPING TECHNIQUE TO THE DETECTION OF FREE RADICALS IN CHARDONNAY WINES

The aging potential of Burgundy chardonnay wines is considered as quality indicator. However, some of them exhibit higher oxidative sensitivity and premature oxidative aging symptoms, which are potentially induced by no-enzymatic oxidation such as Fenton-type reaction (Danilewicz, 2003). This chemical mechanism involves the action of transition metal, native phenolic compounds and oxygen which promote the generation of highly reactive oxygen species (ROS) such as hydroxyl radicals (OH) or 1-hydroxyethyl radicals (1-HER) from oxidation of ethanol. Such mechanism is involved in the radical oxidation occurring during bottle aging. According to Elias et al.,(2009a), the 1-HER is the most abundant radical in forced oxidation treated wines. Consequently, understanding its evolution kinetic in dry white wines is of great importance.

Read More

ESTIMATING THE INITIAL OXYGEN RELEASE (IOR) OF CORK CLOSURES

Many factors influence aging of bottled wine, oxygen transfer through the closure is included. The maximum uptake of wine before oxidation begins varies from 60 mg.L-¹ to 180 mg.L-1 for white and red wines respectively [1].
The process of bottling may lead to considerable amounts of oxygen. The actual contribution of the transfer through the closure system becomes relevant at the bottle storage, but the amounts are small compared to prepacking operations [2] and to the total oxygen attained during filling.

Read More

MODELLING THE AGEING POTENTIAL OF SYRAH RED WINES BY ACCELERATED AGEING TESTS: INFLUENCE OF ANTIOXIDANT ASSAYS AND PHENOLIC COMPOSITION

Red wine ageing is an important step in the red wine evolution and impacts its chemical and sensory characteristics through many chemicals and physico-chemical reactions. The kinetics of these evolutions depend on the wine studied and influence the wine ageing potential. Generally, high quality red wines require a longer period of bottle ageing before consumption¹. The ageing potential is an impor-tant parameter for wine quality and is related to the capacity of a wine to undergo oxidation over time². Phenolic compounds which are ones of the main substrates for oxidation can then potentially modulate ageing potential³.

Read More