OENO IVAS 2019 banner
IVES 9 IVES Conference Series 9 OENO IVAS 9 OENO IVAS 2019 9 Analysis and composition of grapes, wines, wine spirits 9 Identification of cis-2-methyl-4-propyl-1,3-oxathiane as a new volatile sulfur compound (VSC) in wine

Identification of cis-2-methyl-4-propyl-1,3-oxathiane as a new volatile sulfur compound (VSC) in wine

Abstract

Despite their trace concentrations, volatile sulfur compounds (VSCs) are an important category of flavour-active compounds that significantly contribute to desirable or undesirable aromas of many foods and beverages. In wines, VSCs in the form of polyfunctional thiols, notably 3-sulfanylhexan-1-ol (3-SH), 3-sulfanylhexyl acetate (3-SHA), and 4-sulfanyl-4-methyl-pentan-2-one (4-MSP), possess extremely low olfactory thresholds (≈ ng/L) and pleasant “tropical aroma” notes. They have received much attention with respect to their sensory contributions, quantitative occurrences, biogenesis, and thiol management through viticulture and winemaking. However, the fate of these potent volatiles are still not fully understood.

In this work [1], the fate of 3-SH in wine was probed based on the potential sensory and chemistry interactions between 3-SH and acetaldehyde, which led to the identification of cis-2-methyl-4-propyl- 1,3-oxathiane (cis-1) in wine for the first time. Subsequently, a stable isotope dilution assay (SIDA) using headspace–solid-phase microextraction with gas chromatography and mass spectrometry (HS–SPME GC– MS) was developed. A range of parameters was optimised, a deuterated internal standard was synthesised, and the method was fully validated and applied to the quantitation of cis-1 in wines. The aroma detection threshold of 1 was also determined.

The existence of cis-1 in Sauvignon blanc wines from a laboratory-scale fermentation trial was revealed by mass spectral comparison to an authentic standard, linear retention indices of naturally present cis- 1 on two GC columns, and co-injection experiments. Challenges were faced when analysing commercial wine samples due to unknown co-eluting interferences in some wines. After employing d4-1 as the internal standard and evaluating additional capillary column phases, a sensitive SIDA HS–SPME GC–MS method was developed and applied to a survey of commercial wines. Interestingly, trans-1 was not detected whereas cis-1 ranged from undetectable to 460 ng/L, which highly correlated (r = 0.72) to the concentrations of 3-SH, determined in the same wines by HPLC–MS/MS after derivatisation. The aroma detection threshold of 1* in a neutral Australian white wine was found to be 7.1 μg/L. Although cis-1 concentrations in the studied wines were below the odour detection threshold of 1, our results suggest a potential link from cis-1 to the potent VSC 3-SH, and more research is required to gain a better understanding of the importance of cis-1 in wine, from both chemistry and sensory perspectives. The identification and method development work will be presented along with additional experiments involving cis-1 in wine.

references:

[1]. Chen, L., D.L. Capone, and D.W. Jeffery, Identification and Quantitative Analysis of 2-Methyl-4-propyl-1,3-oxathiane in Wine. Journal of Agricultural and Food Chemistry, 2018, 66 (41), 10808–10815.

* Using a commercial standard consisting of 85% cis-1 and 15% trans-1.

DOI:

Publication date: June 23, 2020

Issue: OENO IVAS 2019

Type: Article

Authors

Liang Chen, Dimitra Capone, David Jeffery

The ARC Training Centre for Innovative Wine Production, The University of Adelaide, PMB 1, Glen Osmond, South Australia 5064, Australia 

Contact the author

 

Keywords

wine aroma, tropical fruit, 3-sulfanylhexan-1-ol, stable isotope dilution assay

Tags

IVES Conference Series | OENO IVAS 2019

Citation

Related articles…

The interplay between grape ripening and weather anomalies – A modeling exercise

Current climate change is increasing inter- and intra-annual variability in atmospheric conditions leading to grapevine phenological shifts as well altered grape ripening and composition at ripeness. This study aims to (i) detect weather anomalies within a long-term time series, (ii) model grape ripening revealing altered traits in time to target specific ripeness thresholds for four Vitis vinifera cultivars, and (iii) establish empirical relationships between ripening and weather anomalies with forecasting purposes. The Day of the Year (DOY) to reach specific grape ripeness targets was determined from time series of sugar concentrations, total acidity and pH collected from a private company in the period 2009-2021 in North-Eastern Italy. Non-linear models for the DOY to reach the specified ripeness thresholds were assessed for model efficiency (EF) and error of prediction (RMSE) in four grapevine cultivars (Merlot, Cabernet Sauvignon, Glera and Garganega). For each vintage and cultivar, advances or delays in DOY to target specified ripeness thresholds were assessed with respect to the average ripening dynamics. Long-term meteorological series monitored at ground weather station by means of hourly air temperature and rainfall data were analyzed. Climate statistics were obtained and for each time period (month, bimester, quarter and year) weather anomalies were identified. A linear regression analysis was performed to assess a possible correlation that may exist between ripening and weather anomalies. For each cultivar, ripeness advances or delays expressed in number of days to target the specific ripening threshold were assessed in relation to registered weather anomalies and the specific reference time period in the vintage. Precipitation of the warmest month and spring quarter are key to understanding the effect of climate change on sugar ripeness. Minimum temperatures of May-June bimester and maximum temperatures of spring quarter best correlate with altered total acidity evolution and pH increment during the ripening process, respectively.

Under-vine management effects on grapevine production, soil properties and plant communities in South Australia

Under-vine (UV) management has traditionally consisted of synthetic herbicide use to limit competition between weeds and grapevines. With growing global interest towards non-synthetic chemical use, this study aimed to capture the effects of alternative UV management at two commercial Shiraz vineyards in South Australia, where the sole management variables were UV management since 2016. In adjacent treatment blocks, cultivation (CU) was compared to spontaneous vegetation (SV) in McLaren Vale (MV), and herbicide was compared to SV in Eden Valley (EV). Soil water infiltration rates were slower and grapevine stem water potential was lower in CU compared to SV in MV, with the latter having a plant community dominated by soursob (Oxalis pes-caprae) during winter; while in EV, there was little separation between the treatments. Yields were affected at both sites, with SV being higher in MV and HE being higher in EV. In MV, the only effect on grape must was a lower 13C:12C isotope ratio in CU, indicating greater grapevine water stress. In the grape must at EV, SV had higher total soluble solids, total phenolics, anthocyanins, and yeast available nitrogen; and lower pH and titratable acidity. Pruning weights were not affected by the treatments in MV, while they were higher in HE at EV. Assessments revealed that the differing soil types at the two sites were likely the main determinants of the opposing production outcomes associated with UV management. In the silty loam soil of MV, the higher yields in SV were likely due to more plant-available water, as a potential result of the continuous soil bio-pores formed by winter UV vegetation. Conversely, in the loamy sand soils of EV with a lower cation exchange capacity, the lower yields and pruning weights in SV suggest the UV vegetation competed significantly with the grapevines for available water and nutrients.

δ13C : A still underused indicator in precision viticulture  

The first demonstration of the interest of carbon isotope composition of sugars in grapevine, as an integrated indicator of vineyard water status, dates back to 2000 (Gaudillère et al., 1999; Van Leeuwen et al., 2001). Thanks to the isotopic discrimination of Carbon that takes place during plant photosynthesis, under hydric stress conditions, it is possible to accurately estimate the photosynthetic activity. Ever since, δ13C has been widely applied with success to zonation, terroir studies and vine physiology research, but is still not widely used by viticulturists. This is quite astonishing by considering the impact of global warming on viticulture and the need to improve water management, that would justify a widespread use of δ13C.
The lack of private laboratories proposing the analysis, the cost of the technology, as well as the long analytical delays, have been detrimental to its development. Some laboratories tried to overcome the analytical difficulties of isotopic analysis by using fourier transformed infrared spectroscopy, as a fast and cheap alternative to the official OIV method (IRMS). These claimed FTIR models have never been published or peer reviewed and cannot be considered robust. In this work, thanks to the recent acquisition of IRMS technology, new modern and robust applications of δ13C for viticulture are proposed. This includes the use of the analysis to make parcel separations at harvesting, the possibility to increase the precision of hydric stress cartography and the potential cost reduction when compared with Scholander pressure bomb analysis.

Modeling island and coastal vineyards potential in the context of climate change

Climate change impacts regional and local climates, which in turn affects the world’s wine regions. In the short term, these modifications rises issues about maintaining quality and style of wine, and in a longer term about the suitability of grape varieties and the sustainability of traditional wine regions. Thus, adaptation to climate change represents a major challenge for viticulture. In this context, island and coastal vineyards could become coveted areas due to their specific climatic conditions. In regions subject to warming, the proximity of the sea can moderate extremes temperatures, which could be an advantage for wine. However, coastal and island areas are particular prized spaces and subject to multiple pressures that make the establishment or extension of viticulture complex.
In this perspective, it seems relevant to assess the potentialities of coastal and island areas for viticulture. This contribution will present a spatial optimization model that tends to characterize most suitable agroclimatic patterns in historical or emerging vineyards according to different scenarios. Thanks to an in-depth bibliography a global inventory of coastal and insular vineyards on a worldwide scale has been realized. Relevant criteria have been identified to describe the specificities of these vineyards. They are used as input data in the optimization process, which will optimize some objectives and spatial aspects. According to a predefined scenario, the objectives are set in three main categories associated with climatic characteristics, vineyards characteristics and management strategies. At the end of this optimization process, a series of maps presents the different spatial configurations that maximize the scenario objectives.

Legacy of land-cover changes on soil erosion and microbiology in Burgundian vineyards

Soils in vineyards are recognized as complex agrosystems whose characteristics reflect complex interactions between natural factors (lithology, climate, slope, biodiversity) and human activities. To date, most of the unknown lies in an incomplete understanding of soil ecosystems, and specifically in the microbial biodiversity even though soil microbiota is involved in many key functions, such as nutrient cycling and carbon sequestration. Soil biological properties are indicative of soil quality. Therefore, understanding how soil communities are related to soil ecosystem functioning is becoming an essential issue for soil strategy conservation. Here, we propose to assess the importance of land-cover history on the present-day microbiological and physico-chemical properties. The studied area was selected in the Burgundian vineyards (Pernand-Vergelesses, Burgundy, France) where land occupation has been reconstructed over the last 40 years. Soil samples were collected in five areas reflecting various land cover history (forest, vineyards, shifting from forest to vineyards). For each area, physico-chemical parameters (pH, C, N, P, grain size) were measured and DNA was extracted to characterize the abundance and diversity of microbial communities. The obtained results show significant differences in the five areas suggesting that present-day microbial molecular biomass and bacterial taxonomic is partly inherited from past land occupation. Over longer period of time, such study of land-uses legacies may help to better assess ecosystem recovery and the impact of management practices for a better soil quality and vineyards sustainability.