Significance and Transformation of 3-Alkyl-2-Methoxypyrazines Through Grapes to Wine: Olfactory Properties, Metabolism, Biochemical Regulation, and the HP–MP Cycle

Zhao, Xiaoling; Ju, Young‐Tae; Wei, Xiaofeng; Dong, Shuang; Sun, Xiangyu; Fang, Yulin

doi:10.3390/molecules24244598

Cited by 18 publications

(13 citation statements)

References 97 publications

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“…The detected levels of the individual MPs were below the accepted values for aroma thresholds except for IBMP in the Rosé wine. The observed value was greater than the 1 ng/L perception threshold typically associated with a white wine, but lower than the 10 ng/L values associated with a red wine [23,24]. The increased value is most likely associated with the early harvest of this grape for involvement in the trial.…”

Section: Wine Analysismentioning

confidence: 63%

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Detection of Sub-Aroma Threshold Concentrations of Wine Methoxypyrazines by Multidimensional GCMS

et al. 2021

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Complex matrices, such as wine, provide a challenge in the quantification of compounds. There exists a high likelihood of co-elution in these matrices, thereby artificially increasing the observed concentration. This can often lead to confusing data where compounds are above aroma detection thresholds, but are not detected by olfactory analysis. Additionally, the lack of sensitivity in assays can lead to the non-detection of sub-aroma threshold concentrations and contrasting data when olfactory analysis detects these aromas. To eliminate these pitfalls and gain a better understanding of the role that methoxypyrazines impart green character to wine, a quantitative method using headspace solid-phase microextraction coupled to heart-cutting multidimensional gas chromatography mass spectrometry was developed. The method can quantitate the three common methoxypyrazines found in wine at the picogram per liter level while resolving co-eluting compounds. The proposed method was validated using model wine and wine solutions and was ultimately used for the comparative analysis of white, rosé, and red wines.

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Section: Wine Analysismentioning

confidence: 63%

“…There are several factors that can alter the MPs concentration in wine. Conditions that promote a decrease in the MPs concentration are: grape ripeness, ripening temperature, bunch exposure, and viticultural practices, to name just a few [24][25][26].…”

Section: Wine Analysismentioning

confidence: 99%

Detection of Sub-Aroma Threshold Concentrations of Wine Methoxypyrazines by Multidimensional GCMS

et al. 2021

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“…Warmer temperatures, particularly at night, can decrease IBMP more rapidly along with malic acid [9]. Degradation is likely due, at least in part, to the O-demethylation enzymatic pathway(s) [3]; however, MP degradation in general is not well understood [23]. The final concentration of MPs in grapes is the result of a balance between the biological formation and degradation of MPs throughout the maturation process in berries.…”

Section: Accumulation and Degradation Of Mpsmentioning

confidence: 99%

“…MPs are generally associated with vegetative tissues and immature fruit [1]. When present, they contribute to the vegetal (e.g., bell pepper, peas, leafy), earthy, nutty, and/or moldy aroma of a wine [3]. MPs are key aromatic compounds in some grape cultivars, including Sauvignon blanc [4,5], Cabernet Sauvignon [6], Cabernet franc [7], Merlot [8], and Carménère [9], where low levels contribute to the varietal character of these wines.…”

Section: Introductionmentioning

confidence: 99%

Prevalence and Management of Alkyl-Methoxypyrazines in a Changing Climate: Viticultural and Oenological Considerations

et al. 2021

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Alkyl-methoxypyrazines are an important class of odor-active molecules that contribute green, ‘unripe’ characters to wine and are considered undesirable in most wine styles. They are naturally occurring grape metabolites in many cultivars, but can also be derived from some Coccinellidae species when these ‘ladybugs’ are inadvertently introduced into the must during harvesting operations. The projected impacts of climate change are discussed, and we conclude that these include an altered alkyl-methoxypyrazine composition in grapes and wines in many wine regions. Thus, a careful consideration of how to manage them in both the vineyard and winery is important and timely. This review brings together the relevant literatures on viticultural and oenological interventions aimed at mitigating alkyl-methoxypyrazine loads, and makes recommendations on their management with an aim to maintaining wine quality under a changing and challenging climate.

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“…Methoxypyrazines (MPs) such as 2-methoxy-3-isobutylpyrazine (IBMP) and 2-isopropyl-3-methoxypyrazine (IPMP) are volatile, grape-derived aroma compounds that give herbaceous characters to the wine [37]. Methoxypyrazines are formed by the catabolism of secondary amino acids, such as valine, glutamate, and methionine present in the grape [38].…”

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confidence: 99%

Effect of Agronomic Techniques on Aroma Composition of White Grapevines: A Review

et al. 2021

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Climate change with rising temperatures and the unpredictability of rainy events during ripening leads to tough challenges for the winemakers in preserving the quality of white grape varieties. Grape quality is a complex concept that mainly refers to berry chemical composition, including secondary metabolites such as aroma compounds that in white berries play a key role in the identity of the wine. Terpenes, thiols, C13-norisoprenoids, methoxypyrazines, and nonterpenic alcohols are the most important aroma compounds in white grapes and several of them can be found as free volatiles or bound as glycoconjugate molecules. Agronomic practices in vineyards, such as biostimulant application, irrigation, defoliation, training systems, foliar fertilization, and bunch thinning, can have a positive effect on their concentration. This review aims to highlight the aromatic characteristics of the most utilized white grape cultivars and focus on agronomic techniques in the vineyard to enhance, implement, and intensify their aromatic characteristics. The purpose of this review paper is therefore to investigate the state of the art regarding the exaltation of aroma in white grapes in the scientific literature through sustainable agronomic techniques, but further future investigations are considered necessary given the uncertainty concerning some mechanisms of biosynthesis and their correlation with such agronomic practices.

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Significance and Transformation of 3-Alkyl-2-Methoxypyrazines Through Grapes to Wine: Olfactory Properties, Metabolism, Biochemical Regulation, and the HP–MP Cycle

Cited by 18 publications

References 97 publications

Detection of Sub-Aroma Threshold Concentrations of Wine Methoxypyrazines by Multidimensional GCMS

Detection of Sub-Aroma Threshold Concentrations of Wine Methoxypyrazines by Multidimensional GCMS

Prevalence and Management of Alkyl-Methoxypyrazines in a Changing Climate: Viticultural and Oenological Considerations

Effect of Agronomic Techniques on Aroma Composition of White Grapevines: A Review

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