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…

Mapping and tracking canopy size with VitiCanopy

Understanding vineyard variability to target management strategies, apply inputs efficiently and deliver consistent grape quality to the winery is essential. However, despite inherent vineyard variability, the majority are managed as if they are uniform. VitiCanopy is a simple, grower-friendly tool for precision/digital viticulture that allows users to collect and interpret objective spatial information about vineyard performance. After four years of field and market research, an upgraded VitiCanopy has been created to achieve a more streamlined, technology-assisted vine monitoring tool that provides users with a set of superior new features, which could significantly improve the way users monitor their grapevines. These new features include:
• New user interface
• User authentication
• Batch analysis of multiple images
• Ease the learning curve through enhanced help features
• Reporting via the creation of colour maps that will allow users to assess the spatial differences in canopies within a vineyard.
Use-case examples are presented to demonstrate the quantification and mapping of vineyard variability through objective canopy measurements, ground-truthing of remotely sensed measurements, monitoring of crop conditions, implementation of disease and water management decisions as well as creating a history of each site to forecast quality. This intelligent tool allows users to manage grapevines and make informed management choices to achieve the desired production targets and remain profitable.

Effect of regulated deficit irrigation regime on amino acids content of Monastrell (Vitis vinifera L.) grapes

Irrigation is an important practice to influence vine quality, especially in Mediterranean regions, characterized by hot summers and severe droughts during the growing season. This study focused on deficit irrigation regime influence on amino acids composition of Monastrell grapevines under semiarid conditions (Albacete, Southeastern of Spain). In 2019, two treatments were applied: non-irrigation (NI) and regulated deficit irrigation (RDI), watered at 30% of the estimated crop evapotranspiration from fruit set to onset of veraison. Grape amino acids content was analyzed by HPLC. Berries from non-irrigated vines showed higher concentration of several amino acids, such as tryptophan (73%), arginine (70%), lysine (36%), isoleucine (27%), and leucine (21%), compared to RDI grapes. Arginine is, together with ammonium ion, the principal nitrogen source for yeasts during the alcoholic fermentation; while isoleucine, tryptophan, and leucine are precursors of fermentative volatile compounds, key compounds for wine quality. Moreover, NI treatment increased in a 14% the total amino acids content in grapes compared to RDI treatment. The reported effects might be because yield was 70% higher in RDI vines than in the NI ones and, therefore, the sink demand was increased in the irrigated vines. In addition, NI vines suffered more severe water stress and it is known that the amino acids synthesis and accumulation can be influenced by the plant response to stress. According to the results, the irrigation regime showed effect on amino acids concentration in Monastrell grapes under semiarid conditions. Grapes from non-irrigated vines showed a higher content of several amino acids relevant to the fermentative process and to the wine aroma compounds formation. It is demonstrated that the final content of nitrogen-related components in grapes is influenced by the irrigation regime. The convenience of the irrigation strategy to suggest will depend on the desired wine style and the target yield levels.

A spatial explicit inventory of EU wine protected designation of origin to support decision making in a changing climate

Winemaking areas recognized as protected designations of origin (PDOs) shape important economic, environmental and cultural values that are tied to closely defined geographic locations. To preserve wine products and wine-growing practices adopted in different PDOs these areas are strictly regulated by legal specifications. However, quality viticulture is increasingly under pressure from climate change, which is altering the local conditions of many winegrowing areas. Therefore, maintaining traditional wine products will require the adoption of tailored adaptation strategies, including possible changes in the legal regulation of protected wines. To this end, it is necessary to have a comprehensive knowledge on PDOs including their extension, products and allowed practices. While there have been efforts to build databases that summarize the characteristics for individual wine PDO areas and to quantify the related effects of climate change, much information is still included only in the official documentation of the EU geographical indication register and has never been collected in a comprehensive manner. With this study we aim at filling this gap by building a spatial inventory of European wine PDOs that supports decision making in viticulture in the context of climate change. To map and characterize European wine PDOs, we analysed their legal documents and extracted relevant information useful for climate change adaptation. The output consists of a comprehensive geographical dataset that identifies the boundaries of all 1200 European wine PDOs at unprecedented spatial resolution and includes a set of legally binding regulations, such as authorized vine varieties, maximum yields and planting density. The inventory will allow researchers to analyse the impacts of climate change on European wine PDOs and support decision makers in developing tailored adaptation strategies. This includes, among others, the evaluation of new vineyard site selection, the expansion of cultivated varieties or the authorization of irrigation in vineyards.

Different soil types and relief influence the quality of Merlot grapes in a relatively small area in the Vipava Valley (Slovenia) in relation to the vine water status

Besides location and microclimatic conditions, soil plays an important role in the quality of grapes and wine. Soil properties influence…

Climate projections over France wine-growing region and its potential impact on phenology

Climate change represents a major challenge for the French wine industry. Climatic conditions in French vineyards have already changed and will continue to evolve. One of the notable effects on grapevine is the advancing growing season. The aim of this study is to characterise the evolution of agroclimatic indicators (Huglin index, number of hot days, mean temperature, cumulative rainfall and number of rainy days during the growing season) at French wine-growing regions scale between 1980 and 2019 using gridded data (8 km resolution, SAFRAN) and for the middle of the 21th century (2046-2065) with 21 GCMs statistically debiased and downscaled at 8 km. A set of three phenological models were used to simulate the budburst (BRIN, Smoothed-Utah), flowering, veraison and theoretical maturity (GFV and GSR) stages for two grape varieties (Chardonnay and Cabernet-Sauvignon) over the whole period studied. All the French wine-growing regions show an increase in both temperatures during the growing season and Huglin index. This increase is accompanied by an advance in the simulated flowering (+3 to +9 days), veraison (+6 to +13 days) and theoretical maturity (+6 to +16 days) stages, which are more noticeable in the north-eastern part of France. The climate projections unanimously show, for all the GCMs considered, a clear increase in the Huglin index (+662 to 771 °C.days compared to the 1980-1999 period) and in the number of hot days (+5.6 to 22.6 days) in all the wine regions studied. Regarding rainfall, the expected evolution remains very uncertain due to the heterogeneity of the climates simulated by the 21 models. Only 4 regions out of 21 have a significant decrease in the number of rainy days during the growing season. The two budburst models show a strong divergence in the evolution of this stage with an average difference of 18 days between the two models on all grapevine regions. The theoretical maturity is the most impacted stage with a potential advance between 40 and 23 days according to wine-growing regions.