IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 The 1-hydroxyoctan-3-one, a molecule potentially involved in the fresh mushroom off-flavor in wines

The 1-hydroxyoctan-3-one, a molecule potentially involved in the fresh mushroom off-flavor in wines

Abstract

An organoleptic defect, called fresh mushrooms off-flavor (FMOff), appeared in wines and spirits since the 2000’s. Numerous researches demonstrated that octen-3-one, 3-octanol and octen-3-ol (C8 compounds) were involved in the mushroom off-flavor in wines. Nevertheless, these molecules alone do not explain the entire defect in wines and some odorous zones still remain without chemical identification.  Recently, Crustomyces subabruptus has been shown to be a fungus capable of systematically producing FMOff under oenological conditions. The aim of this work was (a) to identify new markers of FMOff using Crustomyces subabruptus as a laboratory model, (b) to synthesize potential candidates and (c) to correlate the levels of these compounds determined by GC-MS with sensory characterization of healthy and affected wines. In practice, Pinot noir musts were artificially contaminated by Crustomyces subabruptus in the laboratory and then fermented. The musts and corresponding wines were analyzed in an untargeted way by GC-MS. By comparison with MS spectra libraries, the 1-hydroxy-3-octanone was formally and systematically identified in these matrices. This molecule, which has never been identified in grapes nor in wine, was only referenced in the fruit of the papaya mountain after enzymatic hydrolysis of the glycosidic fractions of the fruit pulp. In order to develop a targeted analysis by GC-MS, we synthesized the 1-hydroxy-3-octanone according to a previously published procedure. Briefly, 3-hydroxypropionitrile was first silylated to protect hydroxyl function and then reacted with pentylmagnesium bromide according to the Grignard reaction. The last step involved the deprotection of the resulting alcohol to obtain the expected product. Finally, 30 wines from different vintages (those of 2017, 2018, 2019, and 2021) on which were sensorially detected FMOff were spiked with deuterated internal standards (1-octen-3-one-d2, 1-octen-3-ol-d2, 3-octanol-d4), extracted with a pentane-dichloromethane mixture (2/1, v/v), rectified at 40°C, and then analyzed by GC-MS. The analysis of these wines showed the systematic presence of 1-hydroxy-3-octanone in the 2017 wines with levels that seemed to correlate significantly (test of spearman= 0,81) with the sensory analysis scores, r²=0.65. Wines with high sensory analysis scores for FMOff have a higher level of 1-hydroxyoctan-3-one than those with lower scores. On the other hand, the wines did not systematically contained octen-3-one, 3-octanol or octen-3-ol after 4 years of ageing, suggesting that 1-hydroxy-3-octanone could be a more stable chemical marker than the other compounds in the oenological matrix. In conclusion, 1-hydroxyoctan-3-one is a new molecular candidate for tracking the FMOff. Its formal identification completes the overview of the molecules involved in this defect and opens the way to a better understanding of the appearance and evolution of fresh mushrooms off flavors in wines.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Delcros Léa1, Costis Arnaud2, Collas Sylvie1, Herve Marion1, Blondin Bruno2 and Roland Aurélie2

1MHCS, Comité Champagne, Epernay, ZI Pierre et Marie Curie – 51530 OIRY, France
2SPO, Univ Montpellier INRAE, Institut agro, Montpellier, France

Contact the author

Keywords

1-hydroxyoctan-3-one, Fresh mushroom off-flavor, Wine, Must, Volatiles compounds

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Spatial determination of areas in the Western Balkans region favorable for organic production

In problematic conditions for production of grapes and wine caused by the COVID-19 pandemic and the resulting occurrence of wine surpluses, producers are increasingly turning to the innovative viticulture and winemaking of products that are more appealing to the market and the consumers. On the other hand, consumption of the food safety or organic products, and therefore of organic grapes and wine, is increasingly common in the world, in particular in Europe. The Regional Rural Development Standing Working Group (SWG RRD), as a regional intergovernmental organization gathers actors in the viticulture and winemaking sector from states and territories of the Western Balkans (South-East Europe) in the Expert Working Group for Wine, with the aim of improving viticulture and winemaking in this region through joint activities. In accordance with the aforementioned, the SWG RRD is working on advancing organic production of grapes and wine, and on recognition of specificities of the terroir of wine-growing areas in Western Balkans. In addition, as part of the project “Facilitation of Exchange and Advice on Wine Regulations in Western Balkan Countries” helmed by the German Federal Ministry of Food and Agriculture, in addition to harmonization of relevant legislation with EU regulations, efforts are being invested towards recognition of organic wines. Within activities and project implemented by this organization, expert analyses and scientific research of the terroir of Western Balkans were carried out, and some of the results are presented in this paper.

Extreme canopy management for vineyard adaptation to climate change: is it a good idea?

Climate change constitutes an enormous challenge for humankind and for all human activities, viticulture not being an exception. Long-term strategic changes are probably needed the most, but growers also need to deal with short-term changes: summers that are getting progressively warmer, earlier harvest dates and higher pH in musts and wines. In the last 10-15 years, a relevant corpus of research is being developed worldwide in order to evaluate to which extent extreme canopy management operations, aimed at reducing leaf area and, thus, limiting the source to sink ratio, could be useful to delay ripening. Although extreme canopy management can result in relevant delays in harvest dates, longer term studies, as well as detailed analysis of their implications on carbohydrate reserves, bud fertility and future yield are desirable before these practices can be recommended.

What are the optimal ranges and thresholds for berry solar radiation for flavonoid biosynthesis?

In wine grape production, canopy management practices are applied to control the source-sink balance and improve the cluster microclimate to enhance berry composition. The aim of this study was to identify the optimal ranges of berry solar radiation exposure (exposure) for upregulation of flavonoid biosynthesis and thresholds for their degradation, to evaluate how canopy management practices such as leaf removal, shoot thinning, and a combination of both affect the grapevine (Vitis vinifera L. cv. Cabernet Sauvignon) yield components, berry composition, and flavonoid profile under context of climate change. First experiment assessed changes in the grape flavonoid content driven by four degrees of exposure. In the second experiment, individual grape berries subjected to different exposures were collected from two cultivars (Cabernet Sauvignon and Petit Verdot). The third experiment consisted of an experiment with three canopy management treatments (i) LR (removal of 5 to 6 basal leaves), (ii) ST (thinned to 24 shoots per vine), and (iii) LRST (a combination of LR and ST) and an untreated control (UNT). Berry composition, flavonoid content and profiles, and 3-isobutyl 2-methoxypyrazine were monitored during berry ripening. Although increasing canopy porosity through canopy management practices can be helpful for other purposes, this may not be the case of flavonoid compounds when a certain proportion of kaempferol was achieved. Our results revealed different sensitivities to degradation within the flavonoid groups, flavonols being the only monitored group that was upregulated by solar radiation. Within different canopy management practices, the main effects were due to the ST. Under environmental conditions given in this trial, ST and LRST hastened fruit maturity; however, a clear improvement of the flavonoid compounds (i.e., greater anthocyanin) was not observed at harvest. Methoxypyrazine berry content decreased with canopy management practices studied. Although some berry traits were improved (i.e. 2.5° Brix increase in berry total soluble solids) due to canopy management practices (ST), this resulted in a four-fold increase in labor operations cost, two-fold decrease in yield with a 10-fold increase in anthocyanin production cost per hectare that should be assessed together as the climate continues to get hot.

The use of rootstock as a lever in the face of climate change and dieback of vineyard

As viticulture faces challenges such as climate change or vineyard dieback, the choice of the variety and rootstock becomes more and more crucial. To study rootstock levers in the Bordeaux region, a parcel of Cabernet Sauvignon (CS) was planted with four rootstocks in 2014. Twenty repetitions of each of the following four rootstocks were set up: 101-14 MGt, Nemadex AB, 420A MGt and Gravesac. The number of bunches, yields and pruning weights of the vine shoots were measured individually on 240 vines from 2017 to 2021. Since 2020, nitrogen status assessed by assimilable nitrogen level, hydric status assessed by δ13C and berry maturity were measured on 80 samples taken from 20 repetitions of the four rootstocks. A lower yield was measured for CS grafted onto Nemadex AB due to the lower number of bunches and the lower weight of berries. The differences between the other three rootstocks are small, but CS grafted onto 420A MGt was the most productive. The CS grafted onto Nemadex AB had the lowest pruning weight while 101-14 MGt had the highest. In 2020, δ13C showed a more moderate water stress with 101-14 MGt and 420A MGt than with Nemadex AB. Surprisingly, the Gravesac was under more stress than the 101-14 MGt. The nitrogen status in the berries was better for Nemadex AB but this was perhaps due to the significantly lower weight of the berries.Rootstock 101-14 MGt attained the highest accumulation of sugars in the berries while 420A MGt allows to preserve higher acidity. The parcel is still young which may explain some of the results. These measures must therefore be continued over the next several years to fully assess the effects of these rootstocks on the development of the vines and the quality of the production under new climatic conditions.

How does aromatic composition of red wines, resulting from varieties adapted to climate change, modulate fruity aroma?

One of the major issues for the wine sector is the impact of climate change linked to the increasing temperatures which affects physicochemical parameters of the grape varieties planted in Bordeaux vineyard and consequently, the quality of wine. In some varietals, the attenuation of their fresh fruity character is accompanied by the accentuation of dried-fruit notes [1]. As a new adaptive strategy on climate change, some winegrowers have initiated changes in the Bordeaux blend of vine varieties [2]. This study intends to explore the fruitiness in wines produced from grape varieties adapted to the future climate of Bordeaux. 10 commercial single–varietal wines from 2018 vintage made from the main grape varieties in the Bordeaux region (Cabernet franc, Cabernet-Sauvignon and Merlot) as well as from indigenous grape varieties from the Mediterranean basin, such as Cyprus (Yiannoudin), France (Syrah), Greece (Agiorgitiko and Xinomavro), Portugal (Touriga Nacional) and Spain (Garnacha and Tempranillo), were selected among 19 samples using sensory descriptive analyses. Both sensory and instrumental analyses were coupled, to investigate their fruity aroma expression. For sensory analysis, samples were prepared from wine, using a semi preparative HPLC method which preserves wine aroma and isolates fruity characteristics in 25 specific fractions [3,4]. Fractions of interest with intense fruity aromas were sensorially selected for each wine by a trained panel and mixed with ethanol and microfiltered water to obtain fruity aromatic reconstitutions (FAR) [5]. A free sorting task was applied to categorize FAR according to their similarities or dissimilarities, and different clusters were highlighted. Instrumental analysis of the different FAR and wines demonstrated variations in their molecular composition. Results obtained from sensory and gas chromatography analysis enrich the knowledge of the fruity expression of red wines from “new” grape varieties opening up new perspectives in wine technology, including blending, thus providing new tools for producers.