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

Bueno-Aventín, Elena; Escudero, Ana; Fernández-Zurbano, Purificación; Ferreira, Vicente

doi:10.1021/acs.jafc.1c05880

Cited by 7 publications

(9 citation statements)

References 53 publications

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“…Polyphenols and especially flavanols are readily oxidisable compounds that modulate the presence of desirable (4-methyl-4-mercaptopentanone (4MMP), 3-mercaptohexanol (3MH) or 3-mercaptohexyl acetate (MHA)) and undesirable (hydrogen sulphide (H 2 S)) nucleophilic volatile polyfunctional mercaptans (PFMs). 17 During the wine exposure to oxygen, reactive chemical species in the form of quinones are formed and are therefore available to react with nucleophilic compounds. 18 Phenolic oxidation processes are thus involved in removing these sulfur-containing nucleophilic species.…”

Section: Introductionmentioning

confidence: 99%

White wine phenolics: current methods of analysis

et al. 2022

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White wine phenolic analyses are less common in the literature than analyses of red wine phenolics. Analytical techniques for white wine phenolic analyses using spectrophotometric, chromatographic, spectroscopic, and electrochemical methods are reported. The interest of research in this area combined with the advances in technology aimed at the winemaking industry are promoting the establishment of novel approaches for identifying, quantifying, and classifying phenolic compounds in white wine. This review article provides an overview of the current research into white wine phenolics through a critical discussion of the analytical methods employed. © 2022 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

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Section: Introductionmentioning

confidence: 99%

White wine phenolics: current methods of analysis

et al. 2022

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“…The lower accumulation rates found in white and rosé wines were not expected according to the hypotheses formulated in previous works [ 5 , 23 ]. Whites and rosés have zero or negligible amounts of anthocyanin [ 24 ], which are the molecules suggested as the main consumers of aldehydes [ 5 , 25 ] or sacrificial antioxidants [ 23 ]. However, a lower number of phenolic compounds in general could explain a lower amount of Strecker aldehyde precursor quinones.…”

Section: Resultsmentioning

confidence: 45%

“…Higher O 2 consumption rates, related to higher amounts of delphinidin [ 28 ], Ref. [ 23 ] could be associated with quinones more likely to give the Strecker reaction. Delgado et al demonstrated under extreme conditions (1 h, 180 °C) that polyphenols with hydroxyl groups in the ortho position (as delphinidin) favored the formation of phenylacetaldehyde [ 4 ].…”

Section: Resultsmentioning

confidence: 99%

“…Delgado et al demonstrated under extreme conditions (1 h, 180 °C) that polyphenols with hydroxyl groups in the ortho position (as delphinidin) favored the formation of phenylacetaldehyde [ 4 ]. However, reconstituted wines, which rapidly consumed oxygen due to their high levels of highly antioxidant anthocyanins (dephinidin), produced small amounts of Strecker aldehydes [ 23 ]. The explanation was that these phenols act as oxygen consumers, but not as precursors of the quinones prone to the Strecker reaction, since they are unstable quinones.…”

Section: Resultsmentioning

confidence: 99%

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Factors That Affect the Accumulation of Strecker Aldehydes in Standardized Wines: The Importance of pH in Oxidation

2022

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Strecker aldehydes (SA) can be formed in wine from the degradation of Strecker and, to a lesser degree, via the oxidation of higher alcohols. The objective of this article is to assess the magnitude of the differences introduced by wine compositional factors other than amino acids and Fe, in the accumulation of SA during oxidation. Eight red, two rosé and two white wines were oxidized. The accumulation of SA was analyzed. Whites and rosés presented negative accumulations for isobutyraldehyde, and in general, these wines accumulated smaller concentrations of the other SA than red wines. Only methional and phenylacetaldehyde were accumulated in all of the wines during oxidation. 2-methylbutanal and 3-methylbutanal were accumulated in 9 out of the 12 wines, whereas isobutyraldehyde was accumulated only in 5 out of the 12. 2-methylbutanal was, on average, the least accumulated aldehyde. Methional was the aldehyde formed most homogenously. Most of the observed differences can be attributed to three factors: the pH, oxidation time and native levels of Strecker aldehydes. The influence of pH was particularly intense in the cases of phenylacetaldehyde and methional. An independent test using synthetic wines with Strecker amino acids and 4-methylcatechol with different pHs (4.2, 3.5 and 2.8) was carried out in order to verify the higher pH value, the greater accumulation in SA after oxidation process. The results strongly suggest the important role played by pH in the accumulation of SA in wine oxidation.

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“…In recent papers in which a set of red wines [12] and synthetic wines containing polyphenols from grapes [13] were subject to a forced oxidation procedure [14], the amount of acetaldehyde accumulated was very small, far less than expected. Expectations were based on the common belief that, once SO 2 is depleted, most of the H 2 O 2 formed in the second reduction of O 2 , suffers a catalytic decomposition to form the hydroxyl radical known as Fenton reaction.…”

Section: Introductionmentioning

confidence: 91%

An Index for Wine Acetaldehyde Reactive Potential (ARP) and Some Derived Remarks about the Accumulation of Acetaldehyde during Wine Oxidation

Marrufo-Curtido

Ferreira

Escudero

2022

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The amount of acetaldehyde accumulated during wine oxidation was very small, far less than expected. The existence of polyphenols specifically reactive to acetaldehyde was postuled. In order to assess the acetaldehyde reactive potential (ARP) of wines, different reactive conditions have been studied: acetaldehyde concentration, temperature and pH. The evaluation/validation of developed ARP assay was made with 12 wines. Results have shown that high temperatures cannot be used to estimate wine ARP. In fact, at 70 °C acetaldehyde reacts strictly proportionally to wine total polyphenols. A reproducible index by letting wine at pH 2 react with 35 mgL−1 of acetaldehyde for 7 days was obtained and applied to 12 wines. Rosés did not consume any, whites consumed 8% and reds between 18 and 38% of their total acetaldehyde content. After pH correction, whites ARP can be similar to low ARP reds. Basic kinetic considerations derived from the measurement of ARP were applied to interpret observed acetaldehyde accumulation and consumption during the forced oxidation of the 12 wines. It is concluded that wine ARPs cannot explain the huge fraction of acetaldehyde presumably consumed by wine and the fraction of H2O2 produced during oxidation and not consumed by SO2 has to oxidize majorly wine components other than ethanol.

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

Cited by 7 publications

References 53 publications

White wine phenolics: current methods of analysis

White wine phenolics: current methods of analysis

Factors That Affect the Accumulation of Strecker Aldehydes in Standardized Wines: The Importance of pH in Oxidation

An Index for Wine Acetaldehyde Reactive Potential (ARP) and Some Derived Remarks about the Accumulation of Acetaldehyde during Wine Oxidation

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