2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype

Koch, Alfredo; Doyle, Carolyn; Matthews, Mark A.; Williams, Larry E.; Ebeler, Susan E.

doi:10.1016/j.phytochem.2010.09.006

Cited by 62 publications

(43 citation statements)

References 23 publications

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“…IBMP is known to be abundant in Car and CS (Roujou de Boubée et al, 2002;Belancic and Agosin, 2007), whereas PN and PV berries produce very low amounts of IBMP (Koch et al, 2010). A detailed comparison between all alleles is presented in Supplemental Table S1.…”

Section: Expression Of Recombinant Vvomt Proteins In Escherichia Colimentioning

confidence: 99%

“…cv Cabernet Franc, Cabernet Sauvignon [CS], Sauvignon Blanc, Merlot, and Carménère [Car]; Bayonove et al, 1975;Lacey et al, 1991;Roujou de Boubée et al, 2002;Belancic and Agosin, 2007), whereas they are rarely detected in other cultivars, such as cv Pinot Noir (PN), Chardonnay, or Petit Verdot (PV). This finding indicates a strong genotype dependency of MP biosynthesis (Koch et al, 2010). MPs are accumulated in berries until bunch closure or véraison, and then their level declines after véraison (Hashizume and Samuta, 1999;Ryona et al, 2008).…”

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confidence: 99%

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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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Section: Expression Of Recombinant Vvomt Proteins In Escherichia Colimentioning

confidence: 99%

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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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“…They have been used as biomarkers for identification of hybrid species of grapes (Panighel, Vedova, de Rosso, Gardiman, & Flamini, 2010) and to monitor biosynthetic pathways between grapevines and grapes (Koch, Doyle, Matthews, Williams, & Ebeler, 2010). The latter paper reported the lowest concentration of all compounds from January 2010 to May 2011 with just 2 pg/g of 2-methoxy-3-isobutylpyrazine detected in Semillon wine (Koch et al, 2010). Pyrazines were not the focus of the research for cheese or peppers (Rodríguez-Burruezo et al, 2010;Xiao et al, 2010) but SPME allowed them to be quantified despite their low concentrations.…”

Section: Pyrazinesmentioning

confidence: 99%

Recent analyses using solid phase microextraction in industries related to food made into or from liquids

Heaven

Nash

2012

Food Control

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“…In addition, wines certified for vintage may contain up to 15% of wine from the preceding or subsequent years (Liquor Products Act, 1989). This additional variability can certainly contribute to the observed variance in MP concentrations, particularly considering that the grapevine synthesis of MPs is highly dependent on genotype (Koch et al, 2010), and because of climatic variations between vintages Falcăo et al, 2007).…”

Section: Variations In 3-alkyl-2-methoxypyrazine Content Of South Afrmentioning

confidence: 99%

Quantitative Survey of 3-alkyl-2-methoxypyrazines and First Confirmation of 3-ethyl-2-methoxypyrazine in South African Sauvignon blanc Wines

Alberts

Kidd

Stander

et al. 2016

SAJEV

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3-Alkyl-2-methoxypyrazines are important aroma components in Sauvignon blanc wine, contributing to the typical vegetative character associated with the cultivar. The analysis of methoxypyrazines is highly challenging and, as a result, limited quantitative data are available for South African Sauvignon blanc wines. In this study, liquid chromatography-tandem mass spectrometry was applied for the sensitive quantification of the three principal methoxypyrazines in 881 South African Sauvignon blanc wines. The total wine methoxypyrazine concentration exceeded the combined recognition threshold for the vegetative aroma in more than 60% of the samples, demonstrating the involvement of these compounds in the typical aroma of the cultivar. The analytical method was adapted to allow the accurate quantitation and spectral confirmation of 3-ethyl-2-methoxypyrazine in Sauvignon blanc wines for the first time. Concentrations ranged between 1.1 and 4.9 ng/L. Statistically significant relationships between wine methoxypyrazine concentrations and parameters related to the maturity of the grapes and to the climate, as well as geographical origin and vintage, were found.

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2-Methoxy-3-isobutylpyrazine in grape berries and its dependence on genotype

Cited by 62 publications

References 23 publications

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

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

Recent analyses using solid phase microextraction in industries related to food made into or from liquids

Quantitative Survey of 3-alkyl-2-methoxypyrazines and First Confirmation of 3-ethyl-2-methoxypyrazine in South African Sauvignon blanc Wines

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