Determination of the Importance of In-Mouth Release of Volatile Phenol Glycoconjugates to the Flavor of Smoke-Tainted Wines

Mayr, Christine; Parker, M. Rockwell; Baldock, Gayle A.; Black, Cory A.; Pardon, Kevin H.; Williamson, Patricia; Herderich, Markus; Francis, Leigh

doi:10.1021/jf405327s

Cited by 91 publications

(130 citation statements)

References 15 publications

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“…, Mayr et al . ). This observation was quite surprising, as the hydrolysis must occur quickly to accumulate a detectable concentration of the released aglycone during the short period immediately following tasting.…”

Section: Monoterpenes In Grapes and Winementioning

confidence: 97%

“…Experiments when glycosides were incubated with saliva showed that hydrolysis was variable across individuals, inhibited by low pH, ethanol, glucose and chlorhexidine mouthwash (Mayr et al . ). The hydrolysis also varied for different substrates, with glucosides more readily hydrolysed than disaccharide glycosides such as primeveroside or gentiobioside.…”

Section: Monoterpenes In Grapes and Winementioning

confidence: 97%

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Terpenoids and their role in wine flavour: recent advances

Black

Parker

Siebert

et al. 2015

Australian Journal of Grape and Wine Research

122

111

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The terpenoids are a major class of natural products with a range of functions in plants. In the grape, monoterpenes, sesquiterpenes and C13‐norisoprenoids are present either in a free volatile form, or bound to sugars and rendered non‐volatile. Of the many terpenoids in grapes, only a relatively small number makes an important contribution to wine aroma. This review summarises new developments in understanding terpenoids, including the monoterpenes linalool, cis‐rose oxide, 1,8‐cineole and wine lactone; the sesquiterpene rotundone; and the C13‐norisoprenoids β‐damascenone, β‐ionone, 1,1,6‐trimethyl‐1,2‐dihydronaphthalene and (E)‐1‐(2,3,6‐trimethylphenyl)buta‐1,3‐diene. Their origin, formation and behaviour during winemaking and ageing, and viticultural influences on their concentration, will be discussed, as well as their role in different wine styles.

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Section: Monoterpenes In Grapes and Winementioning

confidence: 97%

Section: Monoterpenes In Grapes and Winementioning

confidence: 97%

Terpenoids and their role in wine flavour: recent advances

Black

Parker

Siebert

et al. 2015

Australian Journal of Grape and Wine Research

122

111

View full text Add to dashboard Cite

show abstract

“…Further sensory investigation established the importance of nonvolatile glycoconjugates of phenols relative to volatile phenols on the in‐mouth flavour characteristics of smoke‐affected wines (Mayr et al. ). A PLS regression analysis of sensory and compositional data from wines made in 2007 and 2009 following significant smoke exposure of vineyards because of bushfires showed that the aroma attributes bandaid and smoky burnt, and the palate attributes bandaid, burnt/charred, and ashy aftertaste were associated strongly with most of the volatile phenols and their glycosides, while the burning aftertaste’ attribute was strongly associated with the alcohol concentration of the wines, and was not related to the smoke‐related attributes (Mayr et al.…”

Section: Smoke Exposure Of Grapes and Vines Berry Composition And Wmentioning

confidence: 99%

Review of smoke taint in wine: smoke-derived volatile phenols and their glycosidic metabolites in grapes and vines as biomarkers for smoke exposure and their role in the sensory perception of smoke taint

Krstic

Johnson

Herderich

2015

Australian Journal of Grape and Wine Research

115

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In recent years, the exposure of vineyards and grapes to smoke from bushfires and controlled burn events has in some instances resulted in wines described as smoke tainted. Such wines are characterised by undesirable sensory characters described as smoky, burnt, ash, smoky bacon, medicinal and ashtray. This review summarises the knowledge about the composition of smoke from forest and grass fires, describes relationships between smoke exposure of vineyards and smoke taint in wine, and outlines strategies for managing and reducing the risk to producing smoke‐affected wines. The sensitivity of grapes and vines at different phenological stages to the uptake of contaminants from smoke, especially smoke‐derived volatile phenols, is outlined, and the pathways for entry and metabolic transformation of volatile phenols are discussed. The potential for translocation of phenolic contaminants within the grapevine and the differences in uptake of smoke contaminants of different grape cultivars are also discussed, along with preliminary work on dose/response relationships regarding concentration and duration of exposure and subsequent expression of smoke taint in wine. The chemical basis of smoke taint in wine is described, and the relationship between volatile phenols from combustion of wood/lignin and their glycosides, and sensory panel ratings of smoke attributes in affected wines is discussed. This includes a summary of sensory reconstitution studies and measurement of flavour compounds released from nonvolatile glycosides in mouth and during in vitro model experiments, which corroborate the sensory contribution of glycosylated phenolic substances and their role as flavour precursors. Finally, the review also discusses analytical methods used to quantify free volatile phenolic substances and their associated glycosides, biomarkers for identifying smoke exposure of grapes, and strategies for assessing the risk of quality loss post‐smoke exposure. Case studies are presented that outline the influence of harvesting and winemaking practices on the expression of smoke taint, and that describe oenological approaches to ameliorate smoke taint in wine.

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“…These nonvolatile glycosides could be stored in grapes [26] and hydrolyzed by acid or enzymes during fermentation or storage, subsequently releasing the volatile compounds into wine [27] (Chapter 23.1). These glycosides can also be released in-mouth due to oral microflora (and therefore perceived retronasally) [17,28], and the phenomenon of glycosylation of exogenous volatiles by grape berries and release during fermentation and storage (or enzymatically) has since been extended to studies involving the deliberate application of oak extracts to grapevines in the vineyard [29][30][31]. …”

Section: Fermentation -Release From Grape-derived Glycosidesmentioning

confidence: 99%