Tags

Type your tag names separated by a space and hit enter

Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity.
Molecules. 2019 May 18; 24(10)M

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.

Links

PMC Free PDF

Authors+Show Affiliations

Zeng L
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. liming.zeng@changins.ch. INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. liming.zeng@changins.ch.
Pons-Mercadé P
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pepome@gmail.com. INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pepome@gmail.com.
Richard T
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. tristan.richard@u-bordeaux.fr. INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. tristan.richard@u-bordeaux.fr.
Krisa S
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. Stephanie.Krisa@u-bordeaux.fr. INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. Stephanie.Krisa@u-bordeaux.fr.
Teissèdre PL
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pierre-louis.teissedre@u-bordeaux.fr. INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. pierre-louis.teissedre@u-bordeaux.fr.
Jourdes M
Univ. Bordeaux, ISVV, EA 4577, Œnologie, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. michael.jourdes@u-bordeaux.fr. INRA, ISVV, USC 1366 INRA, IPB, 210 Chemin de Leysotte, F-33140 Villenave d'Ornon, France. michael.jourdes@u-bordeaux.fr.

MeSH

Amyloid beta-PeptidesAnimalsBiflavonoidsCatechinChromatography, High Pressure LiquidMagnetic Resonance SpectroscopyMolecular ConformationMolecular StructurePlant ExtractsProanthocyanidinsProtective AgentsProtein MultimerizationVitis

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31109031

Citation

Zeng, Liming, et al. "Crown Procyanidin Tetramer: a Procyanidin With an Unusual Cyclic Skeleton With a Potent Protective Effect Against Amyloid-β-Induced Toxicity." Molecules (Basel, Switzerland), vol. 24, no. 10, 2019.
Zeng L, Pons-Mercadé P, Richard T, et al. Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity. Molecules. 2019;24(10).
Zeng, L., Pons-Mercadé, P., Richard, T., Krisa, S., Teissèdre, P. L., & Jourdes, M. (2019). Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity. Molecules (Basel, Switzerland), 24(10). https://doi.org/10.3390/molecules24101915
Zeng L, et al. Crown Procyanidin Tetramer: a Procyanidin With an Unusual Cyclic Skeleton With a Potent Protective Effect Against Amyloid-β-Induced Toxicity. Molecules. 2019 May 18;24(10) PubMed PMID: 31109031.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Crown Procyanidin Tetramer: A Procyanidin with an Unusual Cyclic Skeleton with a Potent Protective Effect against Amyloid-β-Induced Toxicity. AU - Zeng,Liming, AU - Pons-Mercadé,Pere, AU - Richard,Tristan, AU - Krisa,Stéphanie, AU - Teissèdre,Pierre-Louis, AU - Jourdes,Michael, Y1 - 2019/05/18/ PY - 2019/04/27/received PY - 2019/05/16/revised PY - 2019/05/17/accepted PY - 2019/5/22/entrez PY - 2019/5/22/pubmed PY - 2019/11/15/medline KW - condensed tannin KW - crown procyanidin KW - grape KW - procyanidin KW - red wine JF - Molecules (Basel, Switzerland) JO - Molecules VL - 24 IS - 10 N2 - 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/31109031/Crown_Procyanidin_Tetramer:_A_Procyanidin_with_an_Unusual_Cyclic_Skeleton_with_a_Potent_Protective_Effect_against_Amyloid_β_Induced_Toxicity_ DB - PRIME DP - Unbound Medicine ER -