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 13C CP/MAS NMR AND EPR SPECTROSCOPIC TECHNIQUES TO CHARACTERIZE MACROMOLECULAR CHANGES IN OAK WOOD(QUERCUS PETRAEA) DURING TOASTING

For coopers, toasting process is considered a crucial step in barrel production during which oak wood (Q. petraea) develops several aromatic nuances released to the wine during its maturation. Toasting consists of applying different degrees of heat to a barrel for a specific period. As the temperature increases, thermal degradation of oak wood structure produces a huge range of chemical compounds. Many studies have identified the main key aroma volatile compounds (whisky-lactone, furfural, eugenol, guaiacol, vanillin). However, detailed information on how the chemical structure of oak wood degrades with increasing toasting level is still lacking.

SENSORY PROPERTIES IMPORTANT TO AUSTRALIAN FINE WINE CONSUMER SEGMENT PERCEPTION OF CHARDONNAY WINE COMPLEXITY AND PREFERENCE

Wine complexity is considered a multidimensional yet equivocal sensory percept. This project uncovered sensory attributes Australian Chardonnay wine consumers associate with Chardonnay wine complexity
and correlations between expert and consumer perceived wine complexity and preference. A
wine consumer test examined 6 Australian Chardonnay wines of three complexity levels designated low (LC1&2), medium (MC1&2), and high (HC1&2) by an expert panel (n = 8) using a benchtop sensory task. Consumers (n = 81) rated their perceived liking using a 9-point hedonic scale; wine complexity with a 5-point scale anchored “low”, “low-medium”, “medium”, “medium-high”, and “high” and lastly, profiled the wines using Rate-All-That-Apply (RATA). Psychographic segmentation with the Fine Wine Instrument
(FWI) generated three segments; Wine Enthusiasts (WE n=29), Aspirants (ASP n=40) and No- Frills (NF n=12).

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.

Rootstock mediated responses of grapevine (Vitis vinifera L.) metabolism and physiology to combined water deficit and salinity stress in Syrah grafts

Water deficit and salinity are increasingly affecting the viticulture and wine industry. These two stresses are intimately related; understanding the physiological and metabolic responses of grapevines to water deficit, salinity and combined stress is critical for developing strategies to mitigate the nega- tive impacts of these stresses on wine grape production. These strategies can include selecting more tolerant grapevine cultivars and graft combinations, improving irrigation management, and using soil amendments to reduce the effects of salinity. For this purpose, understanding the response of grape- vine metabolism to altered water balance and salinity is of pivotal importance.

SENSORY IMPROVEMENT OF DEALCOHOLISED WINES

Interest and willing-ness to buy alcohol-free wines by customers is increasing for several years [1]. Due to the rising relevance of dealcoholised wines it is the objective of this study to contribute to a better understanding of the flavor variation among dealcoholised wines and to explore enological measures, how to improve final quality.
First a range of commercial, alcoholfree white wines were analysed by the holistic sensory method projective mapping, including a question for hedonic acceptance. Based on the combination of a non-target-HS-SPME-GC/MS analysis with sensory analysis we obtained a clustering of the wines into three groups.