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…

OTA DEGRADATION BY BACTERIAL LACCASEST

Laccases from lactic acid bacteria (LAB) are described as multicopper oxidase enzymes with copper union sites. Among their applications, phenolic compounds’ oxidation and biogenic amines’ degradation, have been described. Besides, the role of LAB in the toxicity reduction of ochratoxin A (OTA) has been reported (Fuchs et al., 2008; Luz et al., 2018). Fungal laccases, but not bacterial laccases, have been screened for OTA and mycotoxins’ degradation (Loi et al., 2018). OTA is a mycotoxin produced by some fungal species, such as Penicillium and Aspergillus sp., which infect grape bunches used for winemaking.

Read More

THE IMPACT OF NON-SACCHAROMYCES YEASTS ON THE WHITE WINE QUALITY

Selected strains of non-Saccharomyces yeasts showed a positive effect on sensory characteristics and aromatic complexity of wine. A sequential microbial culture of non-Saccharomyces and S. cerevisiae species is usually inoculated due to poorer fermentability of non-Saccharomyces species. The aim of the study was to investigate the role of non-Saccharomyces yeasts in the production of white wines. We evaluated how individual combinations of sequential inoculations of non-Saccharomyces and S. cerevisiae species affect the aromatic compounds (volatile thiols and esters) and sensory characteristics of the wines.

Read More

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].

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

YEAST-PRODUCED VOLATILES IN GRAPE BASED SYSTEM MODEL ACTING AS ANTIFUNGAL BIOAGENTS AGAINST PHYTOPATHOGEN BOTRYTIS CINEREA

Botrytis cinerea Pers., the causal agent of grey mould disease, is responsible for substantial economic losses, as it causes reduction of grape and wine quality and quantity. Exploitation of antagonistic yeasts is a promising strategy for controlling grey mould incidence and limiting the usage of synthetic fungicides. In our previous studies, 119 different indigenous yeasts were screened for putative multidimensional modes of action against filamentous fungus B. cinerea [1]. The most promissing biocontrol yeast was Pichia guilliermondii ZIM624, which exhibited several anatagonistic traits (production of cell wall degrading enzymes, chitinase and β-1,3-glucanase; demonstration of in vitro inhibitory effect on B. cinerea mycelia radial growth; production of antifungal volatiles, assimilation of a broad diversity of carbon sources, contributing to its competitivnes in inhabiting grapes in nature).

Read More