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: 09/02/2024

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…

WINE CONSUMER TRADE-OFF BETWEEN ORGANOLEPTIC CHARACTERISTICS AND SUSTAINABLE CLAIMS. AN EXPERIMENT ON RED WINES FROM BORDEAUX REGION

In economics, the perception of wine quality is not limited to sensorial characteristics: an indication of the region of production significantly affects the perception of quality and consumers’ WTP ([1]; [2]). However, [3] or more recently [4] show that even if a wine has an organic label, the taste of wine remains the predominant criterion in consumer preferences. The contribution of our experiment is to evaluate the impact of responsible attributes (organic label, Non Added Sulfites, HVE certification) on the appreciation of several red wines on the market. More than 280 consumers participated to the present study and they perform 25 tastings divided into 5 different sessions. 20 different red wines from Bordeaux Area are tasted.

UNEXPECTED PRODUCTION OF DMS POTENTIAL DURING ALCOOLIC FERMENTATION FROM MODEL CHAMPAGNE-LIKE MUSTS

The overall quality of aged wines is in part due to the development of complex aromas over a long period (1.) The apparition of this aromatic complexity depends on multiple chemical reactions that include the liberation of odorous compounds from non-odorous precursors. One example of this phenomenon is found in dimethyl sulphide (DMS) which, with its characteristic odor truffle, is a known contributor to the bouquet of premium aged wine bouquet (1). DMS supposedly accumulates during the ten first years of ageing thanks to the hydrolysis of its precursor dimethylsulfoniopropionate (DMSp.) DMSp is a possible secondary by-product from the degradation of S-methylmethionine (SMM), an amino acid iden- tified in grapes (2), which can be metabolized by yeast during alcoholic fermentation.

WHAT’S FUTURE FOR SANTORINI’S VITICULTURE IN THE CONTEXT OF CLIMATE CHANGE

The own-rooted vineyard of Santorini is a unique case of vineyard worldwide that is been cultivated for thousands of years. On the island’s volcanic soil, the vines are still cultivated with traditional techniques, which are adapted to the specific and extreme weather conditions that prevail on it. While climate change is a reality in the Mediterranean region, will Santorini vineyard endure its impact? The study of the traditional training systems, techniques and vine density, as well as the application of sustainable solutions (cover crops and use of kaolin etc.) revealed sustainable methods for the adaptation of the local viticulture to new climatic phenomena that tend to be more and more frequent in the region due to climate change.

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.

YEAST LEES OBTAINED AFTER STARMERELLA BACILLARIS FERMENTATION AS A SOURCE OF POTENTIAL COMPOUNDS TO IMPROVE SUSTAINABILITY IN WINE- MAKING

The yeast residue left over after wine-making, known as wine yeast lees, is a source of various compounds that are of interest for wine and food industry. In winemaking, yeast-derived glycocompounds and proteins represent an example of circular economy approach since they have been proven to reduce the need for bentonite and animal-based fining agents. This leads to a reduced environmental impact in the stabilization and fining processes in winemaking. (de Iseppi et al., 2020, 2021).