Ethylidene-Bridged Flavan-3-ols in Red Wine and Correlation with Wine Age

Drinkine, Jessica; Lopes, Paulo; Kennedy, James A.; Teissèdre, Pierre-Louis; Saucier, Cédric

doi:10.1021/jf070038w

Cited by 77 publications

(67 citation statements)

References 33 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Probably, this type of reaction takes place during the storage and aging of flavonoid-rich foods and beverages. The products of the condensation of catechin and epicatechin with acetaldehyde were detected in wine samples (Saucier et al 1997;Drinkine et al 2007;Wollmann and Hofmann 2013). Taxifolin was also found in wines.…”

Section: Discussionmentioning

confidence: 93%

Antioxidant and iron-chelating properties of taxifolin and its condensation product with glyoxylic acid

Shubina

Shatalin

2017

J Food Sci Technol

View full text Add to dashboard Cite

The condensation of taxifolin with glyoxylic acid was examined, and the properties of the resulting product were compared with those of taxifolin. The structure of the product was determined by NMR spectroscopy. The ability of the polyphenols to scavenge reactive oxygen species (ROS) was estimated by luminoldependent chemiluminescence. The iron-chelating and iron-reducing activities were studied using absorption spectrophotometry. It was shown that the condensation leads to the formation of a dimer consisting of two taxifolin units linked through a carboxymethine bridge at the C-6 and C-8 positions of the A ring. The dimer exhibited a somewhat higher ROS scavenging activity than taxifolin. The iron-binding capacity of the compounds was proportional to the number of polyphenol units. The iron-reducing ability of the dimer was lower than that of taxifolin. Thus, the dimer possessed a higher antioxidant activity than the parent flavonoid. The data obtained may be useful for a better understanding of processes occurring in foods and beverages and in a search for new active compounds.

show abstract

Section: Discussionmentioning

confidence: 93%

Antioxidant and iron-chelating properties of taxifolin and its condensation product with glyoxylic acid

Shubina

Shatalin

2017

J Food Sci Technol

View full text Add to dashboard Cite

show abstract

“…This would indicate that polymerisation rates slowed or that competing tannin-removal reactions became significant compared to competing polymerisation reactions. The depolymerisation of ethanal-bridged tannins and the dehydration of an ethanol-flavan-3-ol adduct formed during ethanal-flavan-3-ol condensation, leading to p-vinylphenols and then to more complex compounds in which the ethanal bridges are rearranged, will contribute to lower concentrations of quantifiable tannins (Drinkine et al, 2007). Pigmented tannin concentrations continued to rise until day 341 in all three treatments (Fig.…”

Section: Methodsmentioning

confidence: 90%

The Effect of Half Plunging and No Plunging as Alternative Winemaking Techniques on Phenolic Extraction and Pigment Composition of Wine

Chittenden

Annand

King

et al. 2015

SAJEV

View full text Add to dashboard Cite

The extraction of phenolics (anthocyanins, total phenolics and tannins) and pigmented tannin evolution in Merlot red wines made using three different winemaking techniques were evaluated over one year. Traditional maceration (TM) (two plunges per day), half plunging (half) and no plunging (NP) methods were compared using triplicate 12 kg vinification. No pre-fermentation maceration occurred and a 15-day fermentation and post-fermentation period was used. The wines were analysed daily during the 15-day maceration period and regularly after pressing during the next 11 months. Phenolic, tannin and colour measurements were analysed using UV/Vis spectral readings processed using the AWRI WineCloud TM . At the end of the 15-day maceration, total phenolics, total pigment and free anthocyanins were significantly lower in concentration in the TM treatment compared with NP. The tannin concentration also was significantly lower from days 10 to 12. Pigmented tannin was consistently at higher concentrations in the TM treatment, although not significantly so, during maceration. The significant differences were maintained as the wine developed over the next 11 months; however, the NP trial wine displayed increased pigmented tannin development compared with the TM, being significantly higher in pigmented tannin from about day 90. Higher colour and phenolic extraction in the NP trial led to higher stable colour development in the resulting wines, with the winemaking having an important effect in modifying the pigment profile of the wines. General wine quality parameters did not differ significantly between the three treatments.

show abstract

“…They can: (1) combine or condense with acetaldehyde and other oxidation products, forming stable cycloaddition products (pyranoanthocyanidins); (2) participate in condensation reactions with other phenolic compounds or self-condense to give other more complex pigments; (3) produce polymeric anthocyanins from condensation reactions between anthocyanins and/or flavan-3-ols directly or mediated by aldehydes; and (4) disappear due to an oxidative mechanism involving direct reaction with peroxide and free radicals and/or through reactions with the oxidized components of the media to yield colorless or brown products (Fulcrand et al 2004, He et al 2012, Jackman et al 1987. SO 2 exhibited a protective effect against the decline in free native anthocyanins, and the data suggests a small enhancement in anthocyanin levels as a result of SO 2 treatment, perhaps by trapping acetaldehyde that had bound to anthocyanins (Drinkine et al 2007). After 20 days, a smaller effect was detected for total anthocyanins, and in both instances the decline was more pronounced after 20 days of treatment when SO 2 levels reached zero in MLL and MLH.…”

Section: Resultsmentioning

confidence: 99%