Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity.
Amyloid beta-Peptides
/ chemistry
Animals
Biflavonoids
/ chemistry
Catechin
/ chemistry
Chromatography, High Pressure Liquid
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Plant Extracts
/ chemistry
Proanthocyanidins
/ chemistry
Protective Agents
/ chemistry
Protein Multimerization
Vitis
/ chemistry
condensed tannin
crown procyanidin
grape
procyanidin
red wine
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
18 May 2019
18 May 2019
Historique:
received:
27
04
2019
revised:
16
05
2019
accepted:
17
05
2019
entrez:
22
5
2019
pubmed:
22
5
2019
medline:
15
11
2019
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 31109031
pii: molecules24101915
doi: 10.3390/molecules24101915
pmc: PMC6572218
pii:
doi:
Substances chimiques
Amyloid beta-Peptides
0
Biflavonoids
0
Plant Extracts
0
Proanthocyanidins
0
Protective Agents
0
procyanidin
4852-22-6
Catechin
8R1V1STN48
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Ministère de l'Education Nationale, de l'Enseignement Superieur et de la Recherche
ID : doctoral financial
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