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…

EFFECT OF DIFFERENT VITICULTURAL AND ENOLOGICAL PRACTICES ON THE PHENOLIC COMPOSITION OF RED WINES

Global climate change is exerting a notable influence on viticulture sector and grape composition. The increase in temperature and the changes in rainfall pattern are causing a gap between phenolic and technological grape maturities [1]. As a result, the composition of grapes at harvest time and, consequently, that of wines are being affected, especially with regards to phenolic composition. Hence, wine quality is decreasing due to changes in the organoleptic properties, such as color and astringency, making necessary to implement new adaptive technologies in wineries to modulate these properties in order to improve wine quality.

EFFECT OF DIFFERENT TEMPERATURE AND WATER-LOSS DEHYDRATION CONDITIONS ON THE PATTERN OF FREE AND GLYCOSYLATED VOLATILE METABOLITES OF ITALIAN RED GRAPES

Post-harvest grape berries dehydration/withering are worldwide applied to produce high-quality sweet and dry wines (e.i., Vin Santo, Tokaji, Amarone della Valpolicella). Temperature and water loss impact grape metabolism [1] and are key variables in modulating the production of grape compounds of oenological interest, such as Volatile Organic Compounds (VOCs), secondary metabolites responsible for the aroma of the final wine.
The aim of this research was to assess the impact of post-harvest dehydration on free and glycosylated VOCs of two Italian red wine grapes, namely Nebbiolo and Aleatico, dehydrated in tunnel under controlled condition (varied temperature and weight-loss, at constant humidity and air flow). From these grapes Sforzato di Valtellina Passito DOCG and Elba Aleatico Passito DOCG, respectively.

NEW METHOD FOR THE QUANTIFICATION OF CONDENSED TANNINS AND OTHER WINE PHENOLIC COMPOUNDS USING THE AUTOMATED BIOSYSTEMS SPICA ANALIZER

Wine phenolic compounds are important secondary metabolites in enology due to their antioxidant and nutraceutical properties, and their role in the development of color, taste, and protection of wine from oxidation and spoilage. Tannins are valuable phenolic compounds that contribute significantly to these wine properties, especially in mouthfeel characteristics; however, tannin determination remains a significant challenge, with manual and time-consuming methods or complex methodologies. The purpose of this study is to propose a novel method for quantifying condensed tannins in finished wine products.

TARTARIC STABILIZATION MAY AFFECT THE COLOR AND POLYPHENOLIC COMPOSITION OF TANNAT RED WINES FROM URUGUAY

Tartrate precipitation affects the properties of wines, due to the formation of crystals that cause turbidity, even after being bottled. The forced tartaric stabilization is carried out frequently for young wines, through various physicochemical procedures. The traditional treatment for tartaric stabilization is refrigeration, but it can have a negative effect on wine’s sensory properties, and particularly on the color of red wines. The aim of this study was to evaluate the effect of different tartaric stabilization options on the color and phenolic composition of Tannat red wines from Uruguay.

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.