Remarkable Biomimetic Chemoselective Aerobic Oxidation of Flavano‐Ellagitannins Found in Oak‐Aged Wine

Petit, Emilie; Lefeuvre, Dorothée; Jacquet, Rémi; Pouységu, Laurent; Deffieux, Denis; Quideau, Stéphane

doi:10.1002/anie.201305839

Cited by 19 publications

(11 citation statements)

References 42 publications

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“…In the last years, the formation of flavano-ellagitannins ( 9 – 12 ) and the β-1- O -ethylvescalagin ( 13 ) in red wines aged in oak barrels has been reported [6,24,25,26,27] (Figure 1). Moreover, the acutissimin A is the precursor of mongolicain A ( 14 ) [28] (Figure 1), which was isolated for the first time inside Quercus mongolica in 1988 [29]. These C -glucosidic ellagitannins and flavano-ellagitannin hybrids exhibit important biological properties such as antioxidant, antitumoral, anti-inflammatory, antibacterial, and antiviral [6,30].…”

Section: Introductionmentioning

confidence: 99%

Ellagitannins and Flavano-Ellagitannins: Red Wines Tendency in Different Areas, Barrel Origin and Ageing Time in Barrel and Bottle

et al. 2019

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During maturation and ageing in oak barrels polyphenolic compounds from oak wood, and particularly C-glucosidic ellagitannins, can be released from wood to the wine. These ellagitannins can be involved in oxidation reactions, affecting the wine’s organoleptic properties such as astringency. In this study C-glucosidic ellagitannins and flavano-ellagitannins, acutissimins A and B and epiacutissimins A and B, as well as mongolicain A, which is the result compound of acutissimin A oxidation, were identified and quantified. The quantification was carried out by HPLC-UV-MS in 185 commercial samples from different cultivar areas (Bordeaux and Rioja), different barrel oak wood (French oak barrels and American oak barrels) and different ageing periods. The results show differences between the two zones in terms of compound concentrations. Moreover, the ageing process in bottle for Bordeaux wines are unlike Rioja wines behavior in bottle.

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Section: Introductionmentioning

confidence: 99%

Ellagitannins and Flavano-Ellagitannins: Red Wines Tendency in Different Areas, Barrel Origin and Ageing Time in Barrel and Bottle

et al. 2019

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“…It is known that the flavano-ellagitannins compounds can be transformed by an oxidative reaction resulting in the mongolicains-like [37] molecules that were not quantified during this study. These evolution compounds may have an important content in th World Congress of Vine and Wine red wine as well as an impact on its sensory perception.…”

Section: Discussionmentioning

confidence: 99%

C-glucosidic ellagitannin concentrations variability during the years in Syrah wines from Languedoc vineyard

et al. 2016

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Abstract. C-Glucosidic ellagitannins, which are the main polyphenolic compounds in oak heartwood, are extracted by wine during aging in oak barrels. The C-glucosidic ellagitannins were extracted and purified (> 95% pure) from Quercus robur heartwood and the hemisynthesis of acutissimins A and B, as well as that of epiacutissimins A and B were performed in an acidic organic solution to identified and quantified their concentration ranges by HPLC-UV-MS in 17 Syrah wine samples from the same cultivar area, Languedoc, same quality wood of French oak barrel, same time of oak barrel ageing (12 months) and different ageing period (years from 1999 to 2011). Unlike our first hypothesis, the linear relationship of a reduction in the total content of ellagitannins with the time spent in bottles is not visible.

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“…Accordingly, it is unsurprising that biomimetic approaches are extensively used in the total synthesis of natural products, including various functionalization or cross‐coupling reactions of phenolic/polyphenolic compounds …”

Section: Biological Significance Of Rons Scavenging‐related Antioxidamentioning

confidence: 99%

The mechanism(s) of action of antioxidants: From scavenging reactive oxygen/nitrogen species to redox signaling and the generation of bioactive secondary metabolites

Hunyadi

2019

Medicinal Research Reviews

142

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Small molecule, dietary antioxidants exert a remarkably broad range of bioactivities, and many of these can be explained by the influence of antioxidants on the redox homeostasis. Such compounds help to modulate the levels of harmful reactive oxygen/nitrogen species, and therefore participate in the regulation of various redox signaling pathways. However, upon ingestion, antioxidants usually undergo extensive metabolism that can generate a wide range of bioactive metabolites. This makes it difficult, but otherwise a need, to identify the ones responsible for the different activities of antioxidants. By better understanding their ways of action, the use of antioxidants in therapy can be improved. This review provides a summary on the role of the in vivo metabolic changes and the oxidized metabolites on the mechanisms behind the bioactivity of antioxidants. A special attention is given to metabolites described as products of biomimetic oxidative chemical reactions, which can be considered as models of free radical scavenging. During such reactions a wide variety of metabolites are formed, and they can exert completely different specific bioactivities as compared to their parent antioxidants. This implies that exploring the free radical scavenging‐related metabolite fingerprint of each antioxidant molecule, collectively defined here as the scavengome, will lead to a deeper understanding of the bioactivity of these compounds. Furthermore, this paper aims to be a working tool for systematic studies on oxidized metabolic fingerprints of antioxidants, which will certainly reveal an often‐neglected segment of chemical space that is a treasury of bioactive compounds.

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Remarkable Biomimetic Chemoselective Aerobic Oxidation of Flavano‐Ellagitannins Found in Oak‐Aged Wine

Cited by 19 publications

References 42 publications

Ellagitannins and Flavano-Ellagitannins: Red Wines Tendency in Different Areas, Barrel Origin and Ageing Time in Barrel and Bottle

Ellagitannins and Flavano-Ellagitannins: Red Wines Tendency in Different Areas, Barrel Origin and Ageing Time in Barrel and Bottle

C-glucosidic ellagitannin concentrations variability during the years in Syrah wines from Languedoc vineyard

The mechanism(s) of action of antioxidants: From scavenging reactive oxygen/nitrogen species to redox signaling and the generation of bioactive secondary metabolites

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