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…

IN DEPTH CHARACTERIZATION OF OENOLOGICAL CHARACTERISTICS OF TWO LACHANCEA THERMOTOLERANS STARTER STRAINS

Non-Saccharomyces starter cultures became increasingly popular over the years because of their potential to produce more distinctive and unique wines. The major benefit of the use of Lachancea thermotolerans as a fermentation starter is its ability to produce relevant amounts of lactic acid and reduce alcoholic strength, making it valuable for mitigating negative impacts of climate change on grapes and wine quality. Besides, like any other non-Saccharomyces yeast, L. thermotolerans can significantly affect a whole range of other physico-chemical wine parameters.

Read More

PHOTO OXIDATION OF LUGANA WINES: INFLUENCE OF YEASTS AND RESIDUAL NITROGEN ON VSCS PROFILE

Lugana wines are made from Turbiana grapes. In recent times, many white and rosé wines are bottled and stored in flint glass bottles because of commercial appeal. However, this practice could worsen the aroma profile of the wine, especially as regards the development of volatile sulfur compounds (VSCs). This study aims to investigate the consequences of exposure to light in flint bottles on VSCs profile of Lugana wines fermented with two different yeasts and with different post-fermentation residual nitrogen.

Read More

S. CEREVISIAE AND O. ŒNI BIOFILMS FOR CONTINUOUS ALCOHOLIC AND MALOLACTIC FERMENTATIONS IN WINEMAKING

Biofilms are sessile microbial communities whose lifestyle confers specific properties. They can be defined as a structured community of bacterial cells enclosed in a self-produced polymeric matrix and adherent to a surface and considered as a method of immobilisation. Immobilised microorganisms offer many advantages for industrial processes in the production of alcoholic beverages and specially increasing cell densities for a better management of fermentation rates.

Read More

ANTIOXIDANT CAPACITY OF INACTIVATED NON-SACCHAROMYCES YEASTS

The importance of the non-Saccharomyces yeasts (NSY) in winemaking has been extensively reviewed in the past for their aromatic or bioprotective capacity while, recently their antioxidant/antiradical potential has emerged under winemaking conditions. In the literature the antioxidant potential of NSY was solely explored through their capacity to improve glutathione (GSH) content during alcoholic fermen- tation [1], while more and more studies pointed out the activity of the non-glutathione soluble fraction released by yeasts [2].

Read More

RED WINE AGING WITHOUT SO₂: WHAT IMPACT ON MICROBIAL COMMUNITY?

Nowadays, the use of food preservatives is controversial, SO2 being no exception. Microbial communities have been particularly studied during the prefermentary and fermentation stages in a context of without added SO2. However, microbial risks associated with SO2 reduction or absence, particularly during the wine aging process, have so far been little studied. The microbiological control of wine aging is a key issue for winemakers wishing to produce wines without added SO2. The aim of the present study is to evaluate the impact of different wine aging strategies according to the addition or not of SO2 on the microbiological population levels and diversity.

Read More