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…

OENOLOGICAL STRATEGIES FOR THE REMOVAL OF PINKING IN WHITE WINE

The pinking of in white wine is the turning of color from yellow to salmon hue. White wines obtained from certain grape varieties (e.g. Chardonnay, Sauvignon blanc, Riesling, Trebbiano di Lugana) showed to be susceptible to pinking [1] that has been evaluated by an assay providing the addition of hydrogen peroxide. Even if its appearance does not seem to affect the sensory properties [2], strategies are necessary for its removal. Nowadays, the treatment with polyvinylpolipirroline (PVPP) was reported to significantly decrease the pink color [3].

SENSORY EVALUATION OF WINE AROMA: SHOULD COLOR-DRIVEN DESCRIPTORS BE USED?

The vocabulary used to describe wine aroma is commonly organized according to color, raising the question of whether they reflect the reality of olfactory perception. Previous studies have assumed this convention of color-aroma matching, and have investigated color’s influence on the perception of aroma only in dyed white wine or in red wine from particular places of origin. Here 48 white and red varietal wines from around the world were evaluated in black glasses then in clear glasses by a panel of wine experts, who gave intensity ratings for aroma attributes commonly used by wine professionals. In black glasses, aromas conventionally associated with white wine were perceived in the red wines, and vice versa.

IMPACT OF THE WINES’ QUALITY ON THE WINE DISTILLATES’ ORGANOLEPTIC PROFILE

Brandy de Jerez (BJ) is a spirit drink made exclusively from spirits and wine distillates and is characterized by the use of casks for aging that previously contained Sherries. The quality and sensory complexity of BJ depend on the raw materials and some factors: grape variety, conditions during processing the wine and its distillation, as well as the aging in the cask. Therefore, the original compounds of the grapes from which it comes are of great interest (1 y 2) being in most cases the Airén variety. Their relationship with the quality of the musts and the wines obtained from them has been studied (3) and varies each year of harvest depending on the weather conditions (4).

INFLUENCE OF CHITOSAN, ABSCISIC ACID AND BENZOTHIADIAZOLE TREATMENTS ON SAVVATIANO (VITIS VINIFERA L.) WINES VOLATILE COMPOSITION PROFILE

In the last decades the use of bioestimulants in viticulture have been promoted as alternative to conven- tional pesticides. Moreover, as bioestimulants promote the biosynthesis of secondary metabolites in grape berries, several studies had investigated their influence on the accumulation of phenolic com- pounds (Monteiro et al., 2022). However, few studies, so far, are focused on the accumulation of the vo- latile compounds and their impact on the produced wines (Giménez-Bañón et al., 2022; Gomez- Plaza et al., 2012; Ruiz Garcia et al., 2014).
This study was conducted in a single vineyard of white autochthonous grapevine variety Savvatia- no (Vitis vinifera L.) in Muses Valley (Askri, Viotia, Greece). Chitosan (CHT), Abscisic Acid (ABA) and Benzothiadiazole (BTH) were applied.

EFFECTS OF LEAF REMOVAL AT DIFFERENT BUNCHES PHENOLOGICAL STAGES ON FREE AND GLYCOCONJUGATE AROMAS OF SKINS AND PULPS OF TWO ITALIAN RED GRAPES

Canopy-management practices are applied in viticulture to improve berries composition and quality, having a great impact on primary and secondary grape metabolism. Among these techniques, cluster zone leaf removal (defoliation) is widely used to manage air circulation, temperature and light radiation of grape bunches and close environment. Since volatiles are quantitatively and qualitatively influenced by the degree of fruit ripeness, the level of solar exposure, and the thermal environment in which grapes ripen, leaf removal has been shown to affect volatile composition of grape berries [1].