Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity

The structure of a new procyanidin tetramer, which we call a crown procyanidin tetramer, with an unprecedented macrocyclic structure has been characterized for the first time. Its comprehensive spectroscopic analysis revealed that it is a symmetric procyanidin tetramer composed of four (−)-epicatech...

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Autores principales: Zeng, Liming, Pons-Mercadé, Pere, Richard, Tristan, Krisa, Stéphanie, Teissèdre, Pierre-Louis, Jourdes, Michael
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6572218/
https://www.ncbi.nlm.nih.gov/pubmed/31109031
http://dx.doi.org/10.3390/molecules24101915
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author Zeng, Liming
Pons-Mercadé, Pere
Richard, Tristan
Krisa, Stéphanie
Teissèdre, Pierre-Louis
Jourdes, Michael
author_facet Zeng, Liming
Pons-Mercadé, Pere
Richard, Tristan
Krisa, Stéphanie
Teissèdre, Pierre-Louis
Jourdes, Michael
author_sort Zeng, Liming
collection PubMed
description The structure of a new procyanidin tetramer, which we call a crown procyanidin tetramer, with an unprecedented macrocyclic structure has been characterized for the first time. Its comprehensive spectroscopic analysis revealed that it is a symmetric procyanidin tetramer composed of four (−)-epicatechin sub-units linked alternatively via 4β→8 or 4β→6 B-type interflavanyl linkages to form the macrocyclic structure. This NMR-characterized carbon skeleton has never been reported before for procyanidins in grape or in wine, neither in the plant kingdom. Surprisingly, the crown procyanidin tetramer appeared to be specifically localized in grape skin, contrasting with the oligomeric and polymeric procyanidins present in seed, skin, and bunch stem. Moreover, this crown procyanidin tetramer showed promising protective effects against amyloid-β induced toxicity.
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spelling pubmed-65722182019-06-18 Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity Zeng, Liming Pons-Mercadé, Pere Richard, Tristan Krisa, Stéphanie Teissèdre, Pierre-Louis Jourdes, Michael Molecules Article The structure of a new procyanidin tetramer, which we call a crown procyanidin tetramer, with an unprecedented macrocyclic structure has been characterized for the first time. Its comprehensive spectroscopic analysis revealed that it is a symmetric procyanidin tetramer composed of four (−)-epicatechin sub-units linked alternatively via 4β→8 or 4β→6 B-type interflavanyl linkages to form the macrocyclic structure. This NMR-characterized carbon skeleton has never been reported before for procyanidins in grape or in wine, neither in the plant kingdom. Surprisingly, the crown procyanidin tetramer appeared to be specifically localized in grape skin, contrasting with the oligomeric and polymeric procyanidins present in seed, skin, and bunch stem. Moreover, this crown procyanidin tetramer showed promising protective effects against amyloid-β induced toxicity. MDPI 2019-05-18 /pmc/articles/PMC6572218/ /pubmed/31109031 http://dx.doi.org/10.3390/molecules24101915 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zeng, Liming
Pons-Mercadé, Pere
Richard, Tristan
Krisa, Stéphanie
Teissèdre, Pierre-Louis
Jourdes, Michael
Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity
title Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity
title_full Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity
title_fullStr Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity
title_full_unstemmed Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity
title_short Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity
title_sort crown procyanidin tetramer: a procyanidin with an unusual cyclic skeleton with a potent protective effect against amyloid-β-induced toxicity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6572218/
https://www.ncbi.nlm.nih.gov/pubmed/31109031
http://dx.doi.org/10.3390/molecules24101915
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