Conformational Interpretation of Vescalagin and Castalagin Physicochemical Properties

Vivas, N.; Laguerre, Michel S.; Boissel, Isabelle Pianet de; Gaulejac, Nathalie Vivas de; Nonier, Marie‐Françoise

doi:10.1021/jf030460m

Cited by 39 publications

(35 citation statements)

References 26 publications

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“…Tannases generally act on gallotannins. However, in the particular case of ellagitannins, the information is scarce and confuse (Vivas et al 2004), mainly due to their chemical complexity and diversity. Saavedra et al (2005) reported that the production of EA has not been explored due to its high production cost and the great amount of subproducts generated as result of ellagitannin biodegradation.…”

Section: Resultsmentioning

confidence: 99%

Ellagic Acid Production from Biodegradation of Creosote Bush Ellagitannins by Aspergillus niger in Solid State Culture

Aguilera-Carbó

Hernández

Augur

et al. 2008

Food Bioprocess Technol

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The ability of Aspergillus niger GH1 in converting creosote bush ellagitannins into ellagic acid (EA) was evaluated in solid state culture. Creosote bush leaves were used to extract the ellagitannins fraction, which was impregnated in polyurethane foam used as support of solid state culture. Ellagitannins content, EA accumulation, and the related enzymatic activities were evaluated. A. niger GH1 was able to completely degrade creosote bush ellagitannins with an EA yield of 23.1% at 36 h of culture. The ability to degrade creosote bush ellagitannins exhibited by A. niger GH1 was clearly associated to an ellagitannin-hydrolysing enzyme with a maximum activity of 43 U/l, while that ability was not associated to tannase activity that was detected in the culture extract. This study demonstrated the great ability of A. niger GH1 to hydrolyze ellagitannins and the potential of solid state culture to produce the antioxidant EA by degradation of creosote bush ellagitannins.

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Section: Resultsmentioning

confidence: 99%

Ellagic Acid Production from Biodegradation of Creosote Bush Ellagitannins by Aspergillus niger in Solid State Culture

Aguilera-Carbó

Hernández

Augur

et al. 2008

Food Bioprocess Technol

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“…However, despite the potential quantity of extractable ellagitannins in oak heartwood, the concentration in maturing spirits in cask is low . These results assume that ellagitannins in various reactions contribute to reduced concentration by chemical reactivity, such as oxidation . During spirit ageing, oxidation and hydrolysis/ethanolysis reactions participate in the transformation of polyphenols, such as ellagitannins.…”

Section: Discussionmentioning

confidence: 99%

Extraction of phenolics from new oak casks during spirit maturation: impact on spirit colour

et al. 2020

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The increase in colour and solubilisation of extract, polyphenols and ellagitannins were studied in wine spirit in new oak casks over a period of 23 years. Ellagitannins and oak colour were solubilised during the early years of maturation. After five years, the concentration of ellagitannins decreased markedly, while colour increased, although at a lower rate. Ellagitannins were oxidised into coloured polymers and hydrolysed into ellagic acid. The dry extract, containing polysaccharides, polyphenols and lignin, increased throughout maturation, growing quickly during the early years and slowly thereafter. In a model solution, ethanol exhibits a strong solvent effect. For higher concentrations (50% v/v and more), the extraction of colour was faster, and was typically dark yellow/brown with a red tone, attributable in part to the solubilisation of lignin and lignin by‐products. © 2020 The Institute of Brewing & Distilling

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“…In fact, 1 is reported to be more hydrophilic than 2 and with increased capacity to participate in hydrogen bonding due to the spatial organization of its OH at position C1 of the glycosidic chain. 24 In addition, the interaction can also comprise charge shielding effects and/or molecular rearrangements of the ligand/peptide complexes. Interestingly, ITC data is consistent with the ThT, WB and CD results by suggesting that the complexes formed between compound 1 and Aβ42 are more stable and energetically more favourable.…”

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confidence: 99%

Vescalagin and castalagin reduce the toxicity of amyloid-beta42 oligomers through the remodelling of its secondary structure

et al. 2020

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The isomers vescalagin and castalagin protect SH-SY5Y cells from Aβ42-mediated death. This is achieved better by vescalagin due to the spatial organization of its OH group at the C1 position of the glycosidic chain, improving its capacity to remodel the secondary structure of toxic Aβ42 oligomers.Alzheimer´s Disease (AD) is the most common cause of dementia, characterized by cognitive impairment and memory loss. 1 The most characteristic hallmarks of AD are the presence of intracellular neurofibrillary tangles (of hyperphosphorylated Tau protein) in the affected neurons, and the deposition of extracellular plaques of amyloid-β (Aβ) peptides in the hippocampus and entorhinal cortex. In the case of the amyloid deposits, they are usually composed of Aβ of different lengths, i.e. between 38 and 43 amino acids. Aβ is produced by neurons during the sequential proteolytic cleavage of amyloid precursor protein (APP). 2 Aβ (1-42) (Aβ42) is the less abundant species, however, it is the most amyloidogenic due to its higher propensity to self-assemble into supramolecular aggregates, which has been linked with the predominance of hydrophobic amino acid residues at its C-terminus. 3 Aβ42 can exist in several forms, e.g. monomers, oligomers or fibrils, however, its oligomeric species are reported to be the most cytotoxic 4 . They comprise different levels of association, such as dimers, trimers and higher hierarchical assemblies that lead to the formation of

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Conformational Interpretation of Vescalagin and Castalagin Physicochemical Properties

Cited by 39 publications

References 26 publications

Ellagic Acid Production from Biodegradation of Creosote Bush Ellagitannins by Aspergillus niger in Solid State Culture

Ellagic Acid Production from Biodegradation of Creosote Bush Ellagitannins by Aspergillus niger in Solid State Culture

Extraction of phenolics from new oak casks during spirit maturation: impact on spirit colour

Vescalagin and castalagin reduce the toxicity of amyloid-beta42 oligomers through the remodelling of its secondary structure

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