(+)-Catechin−Aldehyde Condensations:  Competition between Acetaldehyde and Glyoxylic Acid

Drinkine, Jessica; Glories, Yves; Saucier, Cédric

doi:10.1021/jf0504723

Cited by 48 publications

(52 citation statements)

References 21 publications

(48 reference statements)

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“…7). The formation of acetaldehyde from ethanol and glyoxylic acid from tartaric acid due to oxidation can lead to the polymerisation of catechin molecules (Drinkine et al, 2005). A small decrease in the total tannin concentration and a small increase in colour hue in the treated wines were observed (results not shown).…”

Section: Figurementioning

confidence: 93%

The Effect of Micro-oxygenation on the Phenolic Composition, Quality and Aerobic Wine-Spoilage Microorganisms of Different South African Red Wines

Toit

Lisjak

Marais

et al. 2017

SAJEV

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The effect of micro-oxygenation treatments on the composition of different South African red wines was evaluated. In some wines, micro-oxygenation led to an increase in colour density, with a corresponding change in colour, due to the formation of polymeric pigments. This increase also led to the red colour becoming more resistant to the bleaching effect of SO2. Micro-oxygenation also seemed to be more effective in increasing the colour densities of younger red wines than the older ones, although total red pigments were found to be highest in an older red wine that had received micro-oxygenation. Differences in the gelatine index were also observed over time. The micro-oxygenated and barrel-matured wines also had lower concentrations of catechin and the procyanidin B1, and showed a corresponding increase in polymeric pigment and polymeric phenols. Micro-oxygenation led to higher acetic acid bacteria counts, although no increase in volatile acidity was observed in these wines. A tasting panel preferred younger red wines that had undergone micro-oxygenation. In an older red wine prolonged micro-oxygenation led to the wine becoming over-aged, with an increase in the barnyard/medicinal character, which corresponded with an increase in Brettanomyces counts. Micro-oxygenation can be used to increase the quality of young red wines, but further research is needed in this area.

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Section: Figurementioning

confidence: 93%

The Effect of Micro-oxygenation on the Phenolic Composition, Quality and Aerobic Wine-Spoilage Microorganisms of Different South African Red Wines

Toit

Lisjak

Marais

et al. 2017

SAJEV

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“…This leads to C6-C6, C6-C8 or C8-C8 interactions between two (+)-catechin molecules, with the latter forming at the highest concentrations and the C6-C6 forming at very low concentrations, probably due to steric hindrance. Drinkine et al (2005) investigated the effect of adding glyoxylic acid and acetaldehyde to (+)-catechin. They found that glyoxylic acid alone led to a three times faster disappearance of (+)-catechin than acetaldehyde alone (t1/2= 2.3+/-0.2 h for glyoxylic acid and t1/2= 6.7+/-0.2 h for acetaldehyde).…”

Section: Effect Of Oxygen On White Wine Colourmentioning

confidence: 99%

“…When mixed together, ethyl-bridged dimers appeared and disappeared sooner than carboxymethine-bridged dimers. Polymerisation proceeded further, up to tetramer units, with polymers containing both ethyl and carboxymethine-bridges (Saucier et al, 1997;Drinkine et al, 2005). These reactions were, however, executed in the absence of metal catalysts, which would have induced the formation of xanthylium salts.…”

Section: Effect Of Oxygen On White Wine Colourmentioning

confidence: 99%

“…HPLC analysis revealed that vanillic, syringic, coutaric acids, and especially flavan-3-ol derivatives, were significantly reduced by the yeast addition. Yeast prevents the degradation of (-)-epicatechin and (+)-catechin, exhibiting a stronger inhibition of the degradation of the latter com- The formation of dimers from glyoxylic acid and acetaldehyde (Drinkine et al, 2005). pound. This explains the prevention of brown colouration of sherry with flor yeast.…”

Section: Effect Of Oxygen On White Wine Colourmentioning

confidence: 99%

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Oxygen in Must and Wine: A review

Toit

Marais

Pretorius

et al. 2017

SAJEV

107

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The atmosphere consists of approximately 21% oxygen (O2). It plays a crucial role in many metabolic and chemical reactions on earth, thus it is of little surprise that it plays a very important role in the winemaking process. Wine can never be completely protected from it. The general use of sulphur dioxide as an anti-oxidant dates back to the early 18th century and the protection of wine from unwanted oxidative spoilage has been recognised . Oxygen can influence the composition and quality of wine drastically, either positively or negatively, and this will be the focus of this review. This review will also focus on the basic steps involved in oxidation, substrates for oxidation in wine and the evolution of wine constituents during the wine production process when in contact with different concentrations of O2. Basic reactions of oxygen in wineOxidation is the process where electron transfer takes place between reductive and oxidative partners. In wine, O 2 is predominantly responsible for this, with it being reduced to certain intermediates and eventually to hydrogen peroxide and then water. Molecular O2 exists as a diradical and is thus in a triplet ground state. This limits the reactivity of O2 and it cannot form bonds by accepting electron pairs. However, the addition of a single electron, originating from reduced transitional metal ions, can overcome this limitation. This leads to an unpaired electron in the resulting negatively-charged superoxide radical, with a second electron transfer resulting in a peroxide anion (Miller et al., 1990;Danilewicz, 2003). This phenomenon results in O2 being involved in various reactions in wine. Substrates for oxidation in winePhenolic molecules originating from grapes can basically be divided into the non-flavonoids and the flavonoids. The nonflavonoids, which are hydroxybenzoic and hydroxycinnamic derivatives, originate from the grape juice, and are normally the principal phenolic molecules in white wines at concentrations ranging from 50-250 mg/L, depending on the cultivar, winemaking techniques, etc. Examples of non-flavonoids are the tartaric esters of caffeic acid, p-coutaric acid and furanic acids. These molecules have been shown to be the main phenolic molecules in white wine that did not receive prolonged periods of skin contact, because they occur at higher concentrations in the grape juice (Margalit, 1997;Monagas et al., 2005).The second main group of grape-derived phenolics is the flavonoids. This group of molecules basically consists of two phenolic rings attached to a pyran ring. The flavanoids have a more complex structure than the non-flavonoids. In a young wine they are normally in a more unpolymerised state, but as wine matures they undergo different polymerisation reactions in which O 2 plays an important role. The most important flavonoids in wine are the anthocyanins, flavanols and flavonols. Anthocyanins occur mainly in the skins of red grape cultivars and are responsible for the colour of red wine. In young red wines their concentrations can range fr...

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“…The greater risk of cancer in the UADT associated with drinking strong alcoholic beverages highlights the importance of the local effect of ethanol, but the local effect of high levels of acetaldehyde in such beverages may also play a role in carcinogenesis in the UADT (Linderborg et al, 2007). On the other hand, alcoholic beverages contain various congeners, including phenolic compounds, which may affect the local acetaldehyde levels through condensation reactions with acetaldehyde (Drinkine et al, 2005;Es-Safi et al, 2002).…”

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confidence: 99%

Salivary Acetaldehyde Concentration According to Alcoholic Beverage Consumed and Aldehyde Dehydrogenase‐2 Genotype

Yokoyama

Tsutsumi

Imazeki

et al. 2008

Alcoholism Clin & Exp Res

115

127

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(+)-Catechin−Aldehyde Condensations: Competition between Acetaldehyde and Glyoxylic Acid

Cited by 48 publications

References 21 publications

The Effect of Micro-oxygenation on the Phenolic Composition, Quality and Aerobic Wine-Spoilage Microorganisms of Different South African Red Wines

The Effect of Micro-oxygenation on the Phenolic Composition, Quality and Aerobic Wine-Spoilage Microorganisms of Different South African Red Wines

Oxygen in Must and Wine: A review

Salivary Acetaldehyde Concentration According to Alcoholic Beverage Consumed and Aldehyde Dehydrogenase‐2 Genotype

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