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Molecules. 2019 May 18;24(10). pii: E1915. doi: 10.3390/molecules24101915.

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

Author information

1
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. liming.zeng@changins.ch.
2
INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. liming.zeng@changins.ch.
3
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pepome@gmail.com.
4
INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pepome@gmail.com.
5
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. tristan.richard@u-bordeaux.fr.
6
INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. tristan.richard@u-bordeaux.fr.
7
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. Stephanie.Krisa@u-bordeaux.fr.
8
INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. Stephanie.Krisa@u-bordeaux.fr.
9
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pierre-louis.teissedre@u-bordeaux.fr.
10
INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pierre-louis.teissedre@u-bordeaux.fr.
11
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. michael.jourdes@u-bordeaux.fr.
12
INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. michael.jourdes@u-bordeaux.fr.

Abstract

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.

KEYWORDS:

condensed tannin; crown procyanidin; grape; procyanidin; red wine

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