 IVES 9 IVES Conference Series 9 Alternative fate of varietal thiols in wine: identification, formation, and enantiomeric distribution of novel 1,3-oxathianes

Alternative fate of varietal thiols in wine: identification, formation, and enantiomeric distribution of novel 1,3-oxathianes

Abstract

AIM: This study aimed to explore an alternative fate of varietal thiols by identifying and characterising cis-2-methyl-4-propyl-1,3-oxathiane (cis-2-MPO) and cis-2,4,4,6-tetramethyl-1,3-oxathiane (cis-TTMO) in wine. Elucidating these new pathways could aid in explaining the loss of varietal thiols and would further our understanding of the stereochemical relationships between oxathianes and varietal thiols.

METHODS: GC-MS was used to identify cis-2-MPO,1 and a stable isotope dilution assay (SIDA) was developed to quantify its enantiomers after separation with a chiral β-cyclodextrin GC column.2 Varietal thiols and their enantiomers were analysed by SIDA with HPLC-MS/MS to determine their relationship with cis-2-MPO. Production of cis-2-MPO and its correlation with 3-SH, 3-SHA, and acetaldehyde was studied by profiling the evolution of these volatiles during alcoholic fermentation (AF) of Sauvignon blanc (SB) juice fermented with J7, VIN13, and their co-inoculum.3

RESULTS: cis-2-MPO, derived from 3-SH and acetaldehyde, was identified and then measured at up to 460 ng/L (equivalent to 385 ng/L of 3-SH) in a set of wines. Analysis of (2R,4S)-2-MPO and (2S,4R)-2-MPO, arising from thiol enantiomers (3S)-3-SH and (3R)-3-SH, showed respective concentrations of up to 250 and 303 ng/L. The enantiomeric ratio of (2R,4S)-/(2S,4R)-2-MPO was 43:57 whereas that of (3S)-/(3R)-3-SH in the same wines was 51:49.2 Strong correlations were revealed for both 3-SH and cis-2-MPO and their related enantiomeric pairs.The AF study showed cis-2-MPO was produced from an early stage of AF and reached a peak of 847 ng/L (VIN13 ferment) before gradually declining to 50-65 ng/L. Its evolution profile was identical to that of acetaldehyde and 3-SHA, with moderate to strong correlations found for the analytes.Additionally, cis-TTMO, derived from 4-MSPOH and acetaldehyde, was identified in wine as a single enantiomer at concentrations of up to 28 ng/L (equivalent to 23 ng/L of 4-MSPOH). An aroma detection threshold of 14.9 µg/L was determined for cis-TTMO, and this new volatile was described as ‘citrus’, ‘green’, ‘sweet/caramel’, and ‘mango’, shifting toward ‘onion/sweaty’ and ‘sulfurous’ at higher concentrations.2

CONCLUSIONS

The knowledge gained helps rationalise the fate of varietal thiols via the production of oxathianes in wine, and reveals the stereochemical links between these related compounds. A chemical formation pathway to oxathianes was verified and may also apply to other thiols bearing the 1,3-sulfanylalkanol substitution through the reaction with acetaldehyde.

DOI:

Publication date: September 13, 2021

Issue: Macrowine 2021

Type: Article

Authors

Xingchen Wang

Department of Wine Science and Waite Research Institute, The University of Adelaide (UA), PMB 1, Glen Osmond, SA 5064, Australia,Liang, CHEN, Université de Bordeaux, Unité de Recherche Œnologie, EA 4577, USC 1366 INRAE, Institut des Sciences de la Vigne et du Vin, 33882, Villenave d’Ornon cedex, France Dimitra L., CAPONE, Department of Wine Science and Waite Research Institute, Australian Research Council Training Centre for Innovative Wine Production, UA, PMB 1, Glen Osmond, SA 5064, Australia Aurélie, ROLAND, SPO, Univ Montpellier, INRAE, Institut Agro, Montpellier, France David W., JEFFERY, Department of Wine Science and Waite Research Institute, Australian Research Council Training Centre for Innovative Wine Production, UA, PMB 1, Glen Osmond, SA 5064, Australia

Contact the author

Keywords

3-sulfanylhexan-1-ol, 4-methyl-4-sulfanylpentan-2-ol, acetaldehyde, chiral stationary phase, odour detection threshold, sauvignon blanc, stable isotope dilution assay, gas chromatography–mass spectrometry

Citation

Anthocyanins, flavonols and hydroxycinnamates of eight vitis vinifera cultivars from the balearic islands

In 2008 the anthocyanin, flavonol and hydroxycinnamate (HCT) contents of the skins of five coloured berry cultivars (‘Escursac’, ‘Esperó de Gall’, ‘Galmeter’, ‘Valent negre’ and ‘Vinater negre’), of two white cultivars (‘Argamussa’ and ‘Prensal blanc’) and of one weakly rose cultivar (‘Giró ros’), native from Balearic Islands, were characterized.

Eléments importants d’une méthodologie de caractérisation des facteurs naturels du terroir, en relation avec la réponse de la vigne à travers le vin

The French viticultural appellation areas are the result of an empirical, historical and evolutionary selection which, generally, has consecrated a match between natural factors, grape varieties and viti-vinicultural practices. The notion of terroir is the main basis of the Appellation d’Origine Contrôlée in viticulture. It is based on the one hand on privileged natural factors and on the other hand on the know-how of the winegrowers; the whole allowing the production of a wine endowed with an authenticity and a sensory typicity. Wine-growing practices evolve according to progress in viticulture and oenology, while the natural factors of the terroir are much more stable, with the exception of the vintage. They therefore represent a fundamental pillar of the identity of an appellation vineyard.

Combination of NIR multispectral information acquired from a ground moving vehicle with AI methods to assess the vine water status in a Tempranillo (Vitis vinifera L.) commercial vineyard

Increasing water scarcity and unpredictable rainfall patterns necessitate efficient water management in grape production. This study proposes a novel approach for monitoring grapevine water status in a commercial vertically-shoot-positioned Vitis vinifera L. Tempranillo vineyard using non-invasive spectroscopy with a battery of different AI methods to assess vineyard water status, that could drive precise irrigation. A contactless, miniature NIR spectrometer (900-1900 nm) mounted on a moving vehicle (3 Km/h) was employed to collect spectral data from the vines’ northeast side along six dates in season 2021.

Petiole phosphorus concentration is controlled by the rootstock genetic background in grapevine: is this a key for understanding rootstock conferred vigour?

Grapevine, Vitis vinifera, requires grafting on Phylloxera tolerant rootstocks of American origin in most viticultural areas of the world. The most commonly used species in rootstock creation are V. berlandieri, V. riparia and V. rupestris. Rootstocks not only provide tolerance to Phylloxera but assure the supply of water and mineral nutrients to the scion. The objective of this work was to determine to what extent rootstocks of different parentages alter the mineral composition of petioles of grapevine.

La viticoltura veneta in un contesto di città e industria diffusa: per una lettura integrale del paesaggio della collina pedemontana veronese orientale

l Veneto, come è noto, rappresenta una delle estensioni di superfici a vigneto più importanti in Italia e nell’Europa stessa. Il paesaggio viticolo fino ad oggi è stato ampiamente letto nelle sue componenti