How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers

Cretin, Blandine N.; Sallembien, Quentin; Sindt, Lauriane; Daugey, Nicolas; Buffeteau, Thierry; Waffo-Téguo, Pierre; Dubourdieu, Denis; Marchal, Axel

doi:10.1016/j.aca.2015.06.061

Cited by 31 publications

(26 citation statements)

References 26 publications

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“…Despite the non-negligible amounts found, more advanced analytical conditions required for the separation and quantification of its two enantiomers [53,107,119] may justify their non-detection by HPLC under common chromatographic conditions. One of the enantiomers, (+)-lyoniresinol, was also quantified in oak wood [53,92,107], in which it remains stable under toasting until 200 • C [107,117].…”

Section: Phenolic Compounds Found In Aged Wine Spiritsmentioning

confidence: 99%

Phenolic Composition and Related Properties of Aged Wine Spirits: Influence of Barrel Characteristics. A Review

Canas

2017

Beverages

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Abstract:The freshly distilled wine spirit has a high concentration of ethanol and many volatile compounds, but is devoid of phenolic compounds other than volatile phenols. Therefore, an ageing period in the wooden barrel is required to attain sensory fullness and high quality. During this process, several phenomena take place, namely the release of low molecular weight phenolic compounds and tannins from the wood into the wine spirit. Research conducted over the last decades shows that they play a decisive role on the physicochemical characteristics and relevant sensory properties of the beverage. Their contribution to the antioxidant activity has also been emphasized. Besides, some studies show the modulating effect of the ageing technology, involving different factors such as the barrel features (including the wood botanical species, those imparted by the cooperage technology, and the barrel size), the cellar conditions, and the operations performed, on the phenolic composition and related properties of the aged wine spirit. This review aims to summarize the main findings on this topic, taking into account two featured barrel characteristics-the botanical species of the wood and the toasting level.

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Section: Phenolic Compounds Found In Aged Wine Spiritsmentioning

confidence: 99%

Phenolic Composition and Related Properties of Aged Wine Spirits: Influence of Barrel Characteristics. A Review

Canas

2017

Beverages

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“…1 According to statistics, among the 81 chiral NMEs, single enantiomers were the great majority approved by FDA in recent years. For example, (8R,8′R,7′S)-lyoniresinol enantiomer is strongly bitter whereas (8R,8′R,7′S)-lyoniresinol is tasteless 3 ; the S-enantiomers of 4-mercapto-2-hexanone and 4acetylthio-2-hexanone have more fruity and pleasant notes than the R-enantiomers. For example, (8R,8′R,7′S)-lyoniresinol enantiomer is strongly bitter whereas (8R,8′R,7′S)-lyoniresinol is tasteless 3 ; the S-enantiomers of 4-mercapto-2-hexanone and 4acetylthio-2-hexanone have more fruity and pleasant notes than the R-enantiomers.…”

Section: Introductionmentioning

confidence: 99%

“…2 The properties of chiral molecules on chemical and physical are basically the same, while individual enantiomers differ in their biological activity, mechanism, and toxicity. For example, (8R,8′R,7′S)-lyoniresinol enantiomer is strongly bitter whereas (8R,8′R,7′S)-lyoniresinol is tasteless 3 ; the S-enantiomers of 4-mercapto-2-hexanone and 4acetylthio-2-hexanone have more fruity and pleasant notes than the R-enantiomers. 4 Thus, great emphasis has been put on the enantiomeric analysis for the drug safety.…”

Section: Introductionmentioning

confidence: 99%

Analysis of stereoisomers of chiral drug by mass spectrometry

2018

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Chiral molecules are of great importance in the life science since individual enantiomers may differ in biological activity, mechanism, and toxicity, making it necessary to explore efficient chiral analysis methods. Chromatography approaches are often used to differentiate enantiomers while mass spectrometry (MS) was thought to be blind in chiral analysis. With the development of MS technique, it began to play a more and more crucial part in chiral observation. In this review, we will give a detailed introduction of the analysis methods related to MS for chiral drugs, including its mechanism, applications, and future development.

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“…To our knowledge, the enantiomeric distribution of E2H3MB, as well as its organoleptic impact, had never been investigated in wine. Moreover, the detection threshold and descriptors of an organic compound having a sensory impact can differ according to stereoisomer (Lytra et al, 2012;Cretin et al, 2015). Thus, it was important to separate the two enantiomers of E2H3MB to obtain a precise assessment of their organoleptic impact on fruity aromas in red wine.…”

Section: Introductionmentioning

confidence: 99%

Ethyl 2-hydroxy-3-methylbutanoate enantiomers: quantitation and sensory evaluation in wine

Gammacurta¹,

Tempère²,

Marchand³

et al. 2018

OENO One

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Aim:To investigate chemical and sensory characteristics of ethyl 2-hydroxy-3-methylbutanoate in wines. Methods and results:Ethyl 2-hydroxy-3-methylbutanoate has been recently identified as a potential marker of lactic acid bacteria esterase activity. Enantiomers of this fruity ester were quantitated in 99 wines from various vintages and French regions using chiral gas chromatography (γ-cyclodextrin phase). Analyses revealed the predominant presence of the R enantiomer in red and white wines, with a maximum R/S enantiomeric ratio of 94/6 in a 1993 red wine. Results also highlighted greater levels of the ester in red than white wines, depending on grape origin. The detection thresholds of the Rand S-form were estimated at 4 µg/L and 1.5 µg/L in water and 51 mg/L and 21 mg/L in red wine, respectively. Moreover, ranking tests made with levels found in wines did not show significant sensory differences. Conclusion:The concentrations found in wines were considerably below the detection threshold, indicating no direct effect of these compounds on fruity aroma modulation. The absence of significant difference in sensory tests demonstrates that ethyl 2hydroxy-3-methylbutanoate does not contribute significantly to the fruity aroma of red wine.Significance and impact of the study: To our knowledge, no previous research had determined the enantiomeric distribution and the sensory characteristics of this compound in wine.

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How stereochemistry influences the taste of wine: Isolation, characterization and sensory evaluation of lyoniresinol stereoisomers

Cited by 31 publications

References 26 publications

Phenolic Composition and Related Properties of Aged Wine Spirits: Influence of Barrel Characteristics. A Review

Phenolic Composition and Related Properties of Aged Wine Spirits: Influence of Barrel Characteristics. A Review

Analysis of stereoisomers of chiral drug by mass spectrometry

Ethyl 2-hydroxy-3-methylbutanoate enantiomers: quantitation and sensory evaluation in wine

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