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…

EXPLORING RED WINE TYPICITY OF CORBIÈRES: EVALUATION OF THE DEGREE OF IMPACT OF VINIFICATION PROCESS ON THE CHEMICAL COMPOSITION AND ORGANOLEPTIC PROPERTIES OF WINES FROM DIFFERENT TERROIR

It is important nowadays for wine producers to create a product that is an expression of their terroir, a concept including the interaction between a place (topography, climate, soil), the people (tradition, winemaking and viticultural practices) and the resulting product (grape varieties, wines) [1]. Nonetheless, wine’s typicity linked to those terroirs must be easily recognizable by consumers thanks to distinctive sensory characters and composition [2]. Among the compounds of interest, aromatic compounds and polyphenols play an important role in the quality of red wines, by impacting on the odour, color and astringency. To explore the influence of terroir factors, including climate, soil and human practices, on the chemical and sensory profile of wines, red wines from five terroirs of the Corbières appellation were subjected to a general study approach.

Influence of agrophotovoltaic on vine and must in a cool climate

The current energy crisis means that interest in agrophotovoltaics has increased significantly. The reason behind this is that the system aims to combine agricultural production with energy production. During the three-year period from 2020 to 2022, the effects of photovoltaic panels on the vine, the yield and the quality of the must were studied in Walenstadt in northern Switzerland, an area with a cool, humid climate. 65 Pinot noir vines were planted in the 160m2 study area. Because of the large edge effects, only 3 repetitions with 4 vines each could be created. A significantly lower leaf infestation by Plasmopara viticola was observed among the panels in each of the three years.

UNTARGETED METABOLOMICS ANALYSES TO IDENTIFY A NEW SWEET COMPOUND RELEASED DURING POST-FERMENTATION MACERATION OF WINE

The gustatory balance of dry wines is centered on three flavors, sourness, bitterness and sweetness. Even if certain compounds were already identified as contributing to sweetness, some taste modifications remain largely unexplained1,2. Some empirical observations combined with sensory analyzes have shown that an increase of wine sweetness occurs during post-fermentation maceration³. This step is a key stage of red winemaking during which the juice is left in contact with the marc, that contains the solid parts of the grape (seeds, skins and sometimes stems). This work aimed to identify a new taste-active compound that contributes to this gain of sweetness.

HOW DO ROOTSTOCKS AFFECT CABERNET SAUVIGNON AROMATIC EXPRESSION?

Grape quality potential for wine production is strongly influenced by environmental parameters such as climate and agronomic factors such as rootstock. Several studies underline the effect of rootstock on vegetative growth of the scions [1] and on berry composition [2, 3] with an impact on wine quality. Rootstocks are promising agronomic tools for climate change adaptation and in most grape-growing regions the potential diversity of rootstocks is not fully used and only a few genotypes are planted. Little is known about the effect of rootstock genetic variability on the aromatic composition in wines; thus further investigations are needed.

IDENTIFICATION AND LEVELS OF PHENOLIC COMPOUNDS (TANINS, ANTHO-CYANS) IN RED VARIETAL WINES (PROKUPAC AND BLACK TAMJANIKA) FROM SERBIA

The phenolic compounds of red wines represent a source of numerous benefits for human health, which is why they are a constant subject of scientific research. Winemaking in Serbia has a growing economic significance, with particularly autochthonous varieties included [1]. This research identifies and quantifies phenolic compounds of Serbian red varietal wines of Prokupac and Black Tamjanika varieties. Quantification of the level of phenolics has been conducted, including molecular tannins [(+)-catechin, (-)-epicatechin, procyanidin dimers B1, B2, B3, B4], molecular anthocyanins, and the mean degree of polymerization of tannins by HPLC by UV detection, total antioxidant capacity via spectrophotometric methods and chromatic characteristics via CIELAB.