Flavanols react preferentially with quinones through an electron transfer reaction, stimulating rather than preventing wine browning

Ma, Lingjun; Waterhouse, Andrew L.

doi:10.1016/j.aca.2018.07.013

Cited by 40 publications

(33 citation statements)

References 29 publications

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“…41 Additionally, some flavonols, such as quercetin, form quinones with geometrical structures different from those of ortho-quinones, which may hamper the induction of the Strecker degradation. 41 Finally, in the case of mDP, apart from the already higher antioxidant character or more condensed tannins, 48 it may be thought that steric hindrance could limit the efficiency of the quinones 41 to induce Strecker degradation. All this contrasts with the demonstrated ability of flavanols, phenolic acids, and nonpigmented tannins to form quinones, which would explain the positive correlations.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Role of Grape-Extractable Polyphenols in the Generation of Strecker Aldehydes and in the Instability of Polyfunctional Mercaptans during Model Wine Oxidation

Bueno-Aventín

Escudero

Fernández-Zurbano

et al. 2021

J. Agric. Food Chem.

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Polyphenolic fractions from Garnacha, Tempranillo, and Moristel grapes were reconstituted to form model wines of identical pH, ethanol, amino acid, metal, and varietal polyfunctional mercaptan (PFM) contents. Models were subjected to a forced oxidation procedure at 35 °C and to an equivalent treatment under strict anoxia. Polyphenolic profiles significantly determined oxygen consumption rates (5.6–13.6 mg L –1 day –1 ), Strecker aldehyde (SA) accumulation (ratios max/min around 2.5), and levels of PFMs remaining (ratio max/min between 1.93 and 4.53). By contrast, acetaldehyde accumulated in small amounts and homogeneously (11–15 mg L –1 ). Tempranillo samples, with highest delphinidin and prodelphinidins and smallest catechin, consume O 2 faster but accumulate less SA and retain smallest amounts of PFMs under anoxic conditions. Overall, SA accumulation may be related to polyphenols, producing stable quinones. The ability to protect PFMs as disulfides may be negatively related to the increase in tannin activity, while pigmented tannins could be related to 4-methyl-4-mercaptopentanone decrease.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Role of Grape-Extractable Polyphenols in the Generation of Strecker Aldehydes and in the Instability of Polyfunctional Mercaptans during Model Wine Oxidation

Bueno-Aventín

Escudero

Fernández-Zurbano

et al. 2021

J. Agric. Food Chem.

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“…When yeast was not existing, O 2 consumption was highly correlated with MP, free SO 2 and total SO 2 , which are in accordance with the previous observations in the chemical oxidation reactions. 1,19,23 However, no obvious correlation was observed between O 2 consumption and FLA, SPP, and LPP, suggesting the weak effects of Mox on polymeric phenols.…”

Section: Methodsmentioning

confidence: 98%

“…Therefore, quinone and acetaldehyde are the two primary oxidation products in wine. Due to the instability of quinones, , the formation of acetaldehyde is considered an important substance to measure in order to evaluate oxidation. , This is related to the fact that ethanol is the most abundant organic compound in wines, and its primary oxidation product is acetaldehyde.…”

Section: Introductionmentioning

confidence: 99%

Yeasts Induce Acetaldehyde Production in Wine Micro-oxygenation Treatments

Henschen

Nguyen

et al. 2020

J. Agric. Food Chem.

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Micro-oxygenation (Mox) is a common technique used to stabilize color and reduce harsh astringency in red wines. Here, we investigate the role of residual sugars, phenolics, SO 2 , and yeast on the oxidation of wine in three studies. In a Mox experiment, populations of yeasts emerged after the loss of SO 2 , and this was associated with sharp increases in oxygen consumption and acetaldehyde production. No acetaldehyde production was observed without the presence of yeast. In an oxygen saturation experiment, unfiltered wines, in particular those with residual sugar >3 g/L, consumed oxygen more quickly and produced more acetaldehyde than filtered wines. In a final experiment, the reincorporation of oxygen and glucose immediately after the completion of fermentation of an otherwise dry synthetic wine resulted in significant acetaldehyde production. These experiments highlighted the importance of yeast metabolism in determining a wine's response to Mox and suggested that the role of chemical oxidation to produce acetaldehyde during Mox may not be very important. It appears that control of microbial populations and residual sugar levels may be key to managing Mox treatments in winemaking, and production scale experiments should be conducted.

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“…Our results highlight that, regardless of the origin of acetaldehyde in wine, flavanols in white wine are helpful to quench this highly reactive carbonyl by affording more stable compounds. Therefore, on one hand the "catechol" B-ring of flavonoids can be oxidized by quinones through electron transfer reactions leading to flavanoid quinones, precursors of browning products, but on the other they can prevent the negative off-flavors deriving from acetaldehyde produced during oxidation [21].…”

Section: Analysis Of White Winesmentioning

confidence: 99%

How acetaldehyde reacts with low molecular weight phenolics in white and red wines

Cucciniello

Forino²,

Picariello³

et al. 2021

Eur Food Res Technol

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Acetaldehyde is a key compound in determining wine color evolution and sensory properties. Major wine metabolites reactive to acetaldehyde are phenolic compounds, mainly flavan-3-ols and anthocyanins. Many studies have been conducted with the purpose of investigating acetaldehyde reactivity in model solutions, but very poor are the reports of its fate in real wines. By means of LC-HRESIMS and UV/Vis HPLC, red and white wines exposed to an excess of acetaldehyde were analyzed with a specific focus on low molecular weight phenolics. The chemical behavior of acetaldehyde turned out to be different in white and red wines. In white wines, it mainly mediated the formation of vinyl-flavan-3-ol derivatives, while in red wines it led to the formation of ethylidene-bridged red pigments. These latter positively enhanced the color properties of red wines. Conversely, in white wines, the formation of compounds, such as xanthylium ions, causing the undesired browning effects were not detected.

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Flavanols react preferentially with quinones through an electron transfer reaction, stimulating rather than preventing wine browning

Cited by 40 publications

References 29 publications

Role of Grape-Extractable Polyphenols in the Generation of Strecker Aldehydes and in the Instability of Polyfunctional Mercaptans during Model Wine Oxidation

Role of Grape-Extractable Polyphenols in the Generation of Strecker Aldehydes and in the Instability of Polyfunctional Mercaptans during Model Wine Oxidation

Yeasts Induce Acetaldehyde Production in Wine Micro-oxygenation Treatments

How acetaldehyde reacts with low molecular weight phenolics in white and red wines

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