Macrowine 2021
IVES 9 IVES Conference Series 9 From precursor identification to the study of the distribution of 3-methyl-2,4-nonanedione in red wines and spirits

From precursor identification to the study of the distribution of 3-methyl-2,4-nonanedione in red wines and spirits

Abstract

Prematurely aged red wines are marked by intense prune and fig aromatic nuances that dominate the complex bouquet that can be achieved through bottle aging. This oxidation off-flavor is, in part, caused by the presence of 3-methyl-2,4-nonanedione (MND).1 It is interesting to note that similar aromas are also detected in aged spirits. Despite its strong sensory impact in red wines, the precursors of this diketone were not well described.

So, first investigations were performed in order to quantify this compound in young and aged spirits in order to explain these nuances. In addition, determination of MND precursors in red wines as well as the study of oxidation mechanisms on their evolutions will improve our ability to understand its formation pathway in alcoholic beverages.

The first step of this work aimed at identifying a precursor of MND in grapes and wines. Based on the MND distribution in grapes, in young and old wines we hypothesized that ketols might be precursors of this diketone. We describe the chemical synthesis of 2-hydroxy-3-methylnonan-4-one (syn- and anti-ketol) as well as their identification in wines. MND and ketols were quantified by SPME-GC-MS (CI, MeOH) using SIS and MS/MS mode, respectively, in more than 150 Merlot and Cabernet Sauvignon wines from California, Bordeaux, and Switzerland. Oxidation experiments conducted in model wine and red wine demonstrated that ketols are able to produce MND. Based on these data, their role as MND precursor will be discussed. In addition, we also report first results concerning the origin of ketols in grapes and wines.

We also extended our investigations to spirits were old samples can develop similar dried plum aromas. We also report for the first time the distribution of MND in many spirits including Cognac, Armagnac, Brandy, Bourbon, Grappa, Rhum, Whisky. Highest levels were found in grappa (> 10 000 ng/L), exceeding its detection thresholds (100 ng/L). Sensory analysis experiments revealed that this compound contributes to the aroma of spirits. Assay of ketols in these samples revealed that they can be precursors of MND in spirits.

This project has improved our understanding of the formation and evolution of MND in wines, enabling more accurate predictions of the oxidative behavior and aging potential of red wines. In addition, we describe its first identification as well as its sensory impact in spirits

DOI:

Publication date: September 14, 2021

Issue: Macrowine 2021

Type: Article

Authors

Alexandre PONS

Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France, Seguin Moreau Cooperage, ZI Merpins, 16103 Cognac, France. Ana PETERSON, Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France. Fannie THIBAUD, Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France. Jean Charles MATHURIN, E. Rémy Martin & C°, Z.I, 16100 Merpins, France. Yannick LANDAIS, Université Bordeaux, ISM, CNRS UMR 5255, Talence, France. Philippe DARRIET, Université Bordeaux, ISVV, EA 4577, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France. INRA, ISVV, USC 1366, Unité de Recherche Œnologie, F-33882 Villenave d’Ornon, France

Contact the author

Keywords

aging, red wines, oxidation, aroma, spirits, aroma precursor

Citation

Related articles…

Soil, vine, climate change – what is observed – what is expected

To evaluate the current and future impact of climate change on Viticulture requires an integrated view on a complex interacting system within the soil-plant-atmospheric continuum under continuous change. Aside of the globally observed increase in temperature in basically all viticulture regions for at least four decades, we observe several clear trends at the regional level in the ratio of precipitation to potential evapotranspiration. Additionally the recently published 6th assessment report of the IPCC (The physical science basis) shows case-dependent further expected shifts in climate patterns which will have substantial impacts on the way we will conduct viticulture in the decades to come.
Looking beyond climate developments, we observe rising temperatures in the upper soil layers which will have an impact on the distribution of microbial populations, the decay rate of organic matter or the storage capacity for carbon, thus affecting the emission of greenhouse gases (GHGs) and the viscosity of water in the soil-plant pathway, altering the transport of water. If the upper soil layers dry out faster due to less rainfall and/or increased evapotranspiration driven by higher temperatures, the spectral reflection properties of bare soil change and the transport of latent heat into the fruiting zone is increased putting a higher temperature load on the fruit. Interactions between micro-organisms in the rhizosphere and the grapevine root system are poorly understood but respond to environmental factors (such as increased soil temperatures) and the plant material (rootstock for instance), respectively the cultivation system (for example bio-organic versus conventional). This adds to an extremely complex system to manage in terms of increased resilience, adaptation to and even mitigation of climate change. Nevertheless, taken as a whole, effects on the individual expressions of wines with a given origin, seem highly likely to become more apparent.

Impact of geographical location on the phenolic profile of minority varieties grown in Spain. II: red grapevines

Because terroir and cultivar are drivers of wine quality, is essential to investigate theirs effects on polyphenolic profile before promoting the implantation of a red minority variety in a specific area. This work, included in MINORVIN project, focuses in the polyphenolic profile of 7 red grapevines minority varieties of Vitis vinifera L. (Morate, Sanguina, Santafe, Terriza Tinta Jeromo Tortozona Tinta) and Tempranillo) from six typical viticulture Spanish areas: Aragón (A1), Cataluña (A2), Castilla la Mancha (A3), Castilla –León (A4), Madrid (A5) and Navarra (A6) of 2020 season. Polyphenolic substances were extracted from grapes. 35 compounds were identified and quantified (mg subtance/kg fresh berry) by HPLC and grouped in anthocyanins (ANT) flavanols (FLAVA), flavonols (FLAVO), hydroxycinnamic (AH), benzoic (BA) acids and stilbenes (ST). Antioxidant activity (AA, mmol TE /g fresh berry) was determined by DPPH method. The results were submitted to a two-way ANOVA to investigate the influence of variety, area and their interaction for each polyphenolic family and cluster analysis was used to construct hierarchical dendrograms, searching the natural groupings among the samples. Sanguina (A3) had the most of total polyphenols while Tempranillo (A5) those of ANT. Sanguina (A2) and (A3) reached the highest values of FLAVO, FLAVA and AA. These two last samples had also the maximum of AA. The effect cultivar and area were significant for all polyphenolic families analyzed. A high variability due to variety (>50%) was observed in FLAVA and the maximum value of variability due to growing area was detected in AA (86.41%), ANT and FLAVO (51%); the interaction variety*zone was significant only for ANT, FLAVO, EST and AA. Finally, dendrograms presented five cluster: i) Sanguina (A2); ii) Sanguina (A3); iii) Tempranillo (A5); iv) Tempranillo (A3); Terriza (A3,A5), Morate (A5,A6); v) Santafé (A1,A6); Tortozona tinta (A1,A3,A6); Tinta Jeromo (A3,A4).

Modelling vine water stress during a critical period and potential yield reduction rate in European wine regions: a retrospective analysis

Most European vineyards are managed under rainfed conditions, where seasonal water deficit has become increasingly important. The flowering-veraison phenophase represents an important period for vine response to water stress, which is seldomly thoroughly evaluated. Therefore, we aim to quantify the flowering-veraison water stress levels using Crop Water Stress Indicator (CWSI) over 1986–2015 for important European wine regions, and to assess the respective potential Yield Lose Rate (YLR). Additionally, we also investigate whether an advanced flowering-veraison phase may help alleviating the water stress with improved yield. A process-based grapevine model STICS is employed, which has been extensively calibrated for flowering and veraison stages using observed data at 38 locations with 10 different grapevine varieties. Subsequently, the model is being implemented at the regional level, considering site-specific calibration results and gridded climate and soil datasets. The findings suggest wine regions with stronger flowering-veraison CWSI tend to have higher potential YLR. However, contrasting patterns are found between wine regions in France-Germany-Luxembourg and Italy-Portugal-Spain. The former tends to have slight-to-moderate drought conditions (CWSI<0.5) and a negligible-to-moderate YLR (<30%), whereas the latter possesses severe-to-extreme CWSI (>0.5) and substantial YLR (>40%). Wine regions prone to a high drought risk (CWSI>0.75) are also identified, which are concentrated in southern Mediterranean Europe. An advanced flowering-veraison phase may have benefited from cooler temperatures and a higher fraction of spring precipitation in wine regions of Italy-Portugal-Spain, resulting in alleviated CWSI and moderate reductions of YLR. For those of France-Germany-Luxembourg, this can have reduced flowering-veraison precipitation, but prevalent alleviations of YLR are also found, possibly because of shifted phase towards a cooler growing season with reduced evaporative demands. Overall, such a retrospective analysis might provide new insights towards better management of seasonal water deficit for conventionally vulnerable Mediterranean wine regions, but also for relatively cooler and wetter Central European regions.

Impact on leaf morphology of Vitis vinifera L. cvs Riesling and Cabernet Sauvignon under Free Air Carbon dioxide Enrichment (FACE)

Atmospheric carbon dioxide (CO2) concentration has continuously increased since pre-industrial times from 280 ppm in 1750, and is predicted to exceed 700 ppm by the end of 21st century. For most of C3 plant species elevated CO2 (eCO2) improve photosynthetic apparatus results in an increased plant biomass production. To investigate the effects of eCO2 on morphological leaf characteristics the two Vitis vinifera L. cultivars, Riesling and Cabernet Sauvignon, grown in the Geisenheim VineyardFACE (Free Air Carbon dioxide Enrichment) system were used. The FACE site is located at Geisenheim University (49° 59′ N, 7° 57′ E, 94 m above sea level), Germany and was implemented in 2014 comparing future atmospheric CO2-concentrations (eCO2, predicted for the mid-21st century) with current ambient CO2-conditions (aCO2). Experiments were conducted under rain-fed conditions for two consecutive years (2015 and 2016). Six leaves per repetition of the CO2 treatment were sampled in the field and immediately fixed in a FAA solution (ethanol, H2O, formaldehyde and glacial acetic acid). After 24 h leaf samples were transferred and stored in an ethanol solution. Subsequently, leaf tissue was dehydrated using ethanol series and embedded in paraffin. By using a rotary microtomesections of 5 µm were prepared and fixed on microscopic slides. Subsequent the samples were stained using consecutive staining and washing solutions. Afterwards pictures of the leaf cross-sections were taken using a light microscope and consecutive measurements were conducted with an open source image software. Differences found in leaf cross-sections of the two CO2 treatments were detected for the palisade parenchyma. Leaf thickness, upper and lower epidermis and spongy parenchyma remained less affected under eCO2 conditions. The observed results within grapevine leaf tissues can provide first insights to seasonal adaptation strategies of grapevines under future elevated CO2 concentrations.

Current climate change in the Oplenac wine-growing district (Serbia)

Serbian autochthonous vine varieties Smederevka (for white wines) and Prokupac (for rosé and red wines) are the primary representatives of typical characteristics of wines and terroir of numerous wine-growing areas in Serbia. In the past, these varieties were the leading vine varieties, however, as the result of globalization of winemaking and the trend of consumption of wines from widely prevalent vine varieties, they were replaced by introduced international varieties. Smederevka and Prokupac vine varieties are characterized by later time of grape ripening, and relative sensitivity to low temperatures. Climate conditions can be a restrictive factor for production of high-quality grapes and wine and for the spatial spreading of these varieties in hilly continental wine-growing areas.
This paper focuses on the spatial analysis of changes of main climate parameters, in particular, analysis of viticultural bioclimatic indices that were determined for the purposes of viticulture zoning of wine-growing areas in the period 1961-2010, and those same parameters determined for the current, that is, referential climate period (1988-2017). Results of the research, that is, analysis of climate changes indicate that the majority of examined climate parameters in the Oplenac wine-growing district improved from the perspective of Smederevka and Prokupac vine varieties. These studies of climate conditions indicate that changes of analyzed climate parameters, that is, bioclimatic indices will be favorable for cultivation of varieties with later grape ripening times and those more sensitive to low temperatures, such as the autochthonous vine varieties Smederevka and Prokupac, therefore, it is recommended to producers to more actively plant vineyards with these varieties in the territory of the Oplenac wine-growing district.