S-Cysteinylated and S-glutathionylated thiol precursors in grapes. A review

Peña-Gallego, Almudena; Orte, Purificación Hernández; Cacho, Juan

doi:10.1016/j.foodchem.2011.07.079

Cited by 68 publications

(60 citation statements)

References 46 publications

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“…Much research interest has focused more recently on a group of sulfur-containing compounds referred to as the polyfunctional thiols, which impart pleasant fruity aromas to a range of varieties, including Scheurebe, Sauvignon blanc, Gewürztraminer, Riesling, Colombard, Petit Manseng, Semillon, Cabernet Sauvignon, and Merlot (Darriet et al 1995, Guth 1997b, Tominaga et al 1998, 2000a, Murat et al 2001, Peña-Gallego et al 2012. Polyfunctional thiols are thought to be important to the varietal characteristics of wine aroma and are noted for low odor thresholds, with 4MMP, 3MH, and 3MHA detectable in wine at concentrations of ng/L (Tominaga et al 1998, 2000a, Francis and Newton 2005, Swiegers et al 2005a, Dubourdieu and Tominaga 2009).…”

Section: Volatile Sulfur Compoundsmentioning

confidence: 99%

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Robinson

Boss

Solomon

et al. 2013

Am. J. Enol. Vitic.

250

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Abstract:Wine is an ancient beverage and has been prized throughout time for its unique and pleasing flavor. Wine flavor arises from a mixture of hundreds of chemical components interacting with our sense organs, producing a neural response that is processed in the brain and resulting in a psychophysical percept that we readily describe as "wine." The chemical components of wine are derived from multiple sources; during fermentation grape flavor components are extracted into the wine and new compounds are formed by numerous chemical and biochemical processes. In this review we discuss the various classes of chemical compounds in grapes and wines and the chemical and biochemical processes that influence their formation and concentrations. The overall aim is to highlight the current state of knowledge in the area of grape and wine aroma chemistry.

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Section: Volatile Sulfur Compoundsmentioning

confidence: 99%

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Robinson

Boss

Solomon

et al. 2013

Am. J. Enol. Vitic.

250

View full text Add to dashboard Cite

show abstract

“…[16] Thiol conjugates were investigated in a range of studies in the ensuing years to examine aspects such as their prevalence and localisation in grape berries, and transformation during fermentation. [17] In 2009, we identified the GSH conjugate of 4MSP (Fig. 1), which was hypothesised to be present based on knowledge of GSH detoxification pathways (i.e.…”

Section: Identification Of Varietal Thiol Precursors In Grapesmentioning

confidence: 99%

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Jeffery¹

2016

Aust. J. Chem.

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Wine is an amazingly complex natural product that requires dedicated scientists to resolve many of its mysteries. Traditional synthetic organic chemistry and modern analytical techniques are powerful tools at the disposal of wine chemists who tackle the complexities of wine in order to improve scientific understanding and provide practical solutions to industry. Part of this quest for knowledge relates to maintaining or improving wine quality, which underpins consumer acceptance and links to the competitiveness of wineries in a global market. Wine aroma is an important aspect of wine quality and garners much attention from researchers. Grape-derived aroma compounds are one area of particular importance owing to their distinctiveness and ability to impart 'varietal aromas' to wines. Varietal thiols imparting tropical and citrus notes that are characteristic of wines such as Sauvignon Blanc have emerged, along with their grape-derived precursors, as an area of interest over the past two decades. These compounds have also caught our attention and we have made some important contributions to this field, including identifying new precursors, developing novel analytical methods, and conducting studies that provide unique insights into the biochemical transformations occurring in grape berries and juice, and during fermentation.

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“…Quite frequently, they exist mostly in the grape (Vitis vinifera) berry as nonvolatile, odorless, "bound" forms that can be released by chemical and enzymatic reactions occurring during the winemaking and wine aging processes, thus enhancing wine's varietal expression (Styger et al, 2011). Two classical examples are the glycoside precursors of the monoterpenols (Strauss et al, 1986) and the cysteinylated or glutathionylated precursors of the volatile thiols (Tominaga et al, 1998;Peña-Gallego et al, 2012). Noticeable exceptions are the MPs, which are found in grape berries exclusively as free, volatile molecules.…”

mentioning

confidence: 99%

Genetic Analysis of the Biosynthesis of 2-Methoxy-3-Isobutylpyrazine, a Major Grape-Derived Aroma Compound Impacting Wine Quality

et al. 2013

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Methoxypyrazines (MPs) are strongly odorant volatile molecules with vegetable-like fragrances that are widespread in plants. Some grapevine (Vitis vinifera) varieties accumulate significant amounts of MPs, including 2-methoxy-3-isobutylpyrazine (IBMP), which is the major MP in grape berries. MPs are of particular importance in white Sauvignon Blanc wines. The typicality of these wines relies on a fine balance between the pea pod, capsicum character of MPs and the passion fruit/grapefruit character due to volatile thiols. Although MPs play a crucial role in Sauvignon varietal aromas, excessive concentrations of these powerful odorants alter wine quality and reduce consumer acceptance, particularly in red wines. The last step of IBMP biosynthesis has been proposed to involve the methoxylation of the nonvolatile precursor 2-hydroxy-3-isobutylpyrazine to give rise to the highly volatile IBMP. In this work, we have used a quantitative trait loci approach to investigate the genetic bases of IBMP biosynthesis. This has led to the identification of two previously uncharacterized S-adenosyl-methionine-dependent O-methyltransferase genes, termed VvOMT3 and VvOMT4. Functional characterization of these two O-methyltransferases showed that the VvOMT3 protein was highly specific and efficient for 2-hydroxy-3-isobutylpyrazine methylation. Based on its differential expression in high- and low-MP-producing grapevine varieties, we propose that VvOMT3 is a key gene for IBMP biosynthesis in grapevine.

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S-Cysteinylated and S-glutathionylated thiol precursors in grapes. A review

Cited by 68 publications

References 46 publications

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts

Spotlight on Varietal Thiols and Precursors in Grapes and Wines

Genetic Analysis of the Biosynthesis of 2-Methoxy-3-Isobutylpyrazine, a Major Grape-Derived Aroma Compound Impacting Wine Quality

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