Constellation, le dépôt institutionnel de l'Université du Québec à Chicoutimi

Complete 1H and 13C NMR assignments of a series of pergalloylated tannins

Lavoie Serge, Ouellet Michaël, Fleury Pierre-Yves, Gauthier Charles, Legault Jean et Pichette André. (2016). Complete 1H and 13C NMR assignments of a series of pergalloylated tannins. Magnetic Resonance in Chemistry, 54, (2), p. 168-174.

[thumbnail of Lavoie_et_al_2016_MagneticResonanceChemistry_accepted.pdf]
PDF - Version acceptée
[thumbnail of Supporting information]
PDF (Supporting information) - Matériel supplémentaire

URL officielle:


Tannins are secondary metabolites widely distributed in the plant kingdom.1 A common feature of tannins is their phenolic units, which can be linked together to form highly diverse chemical structures.2 Because these compounds constitute an important fraction of the food and beverage ingested,3 they have been thoroughly studied for their biological effects.4-6 Recently, we have performed a phytochemical study on Cornus canadensis, an abundant flowering plant growing wild in North America and giving edible fruits.7 A preliminary bioactivity screening was performed and revealed that an extract from C. canadensis was active toward Herpes simplex virus type 1.8 Following bioassay-guided fractionations, hydrolyzable tannins were identified.9 One of these compounds, namely, 1,2,3,4,6-penta-O-galloyl-β-D-glucopyranose (PGG), has been the subject of several pharmaceutical studies as recently reviewed by Zhang.10 The biological and medicinal properties of PGG are diverse and include anticancer, antioxidant, antimutagenic, anti-inflammatory, anti-allergic, hypocholesterolemic, anticoagulation, antinephrolithiasis, anticonvulsion, antiviral, and antibacterial activities. Furthermore, a series of PGG analogs were synthesized and found to be an optimal scaffold to stimulate glucose transport in adipocytes.11 Some of these compounds were also prepared in our laboratory in order to assess their antiherpetic activities. Because these analogs were only partially characterized by NMR,11 we would like to report herein the complete 1H and 13C assignments of pergalloylated D-glucose (1), D-mannose (2), D-galactose (3), D-xylose (4), L-ribose (5), L-arabinose (6), L-rhamnose (7), and D-fucose (8) by using a combination of one-dimensional and two-dimensional NMR experiments.

Type de document:Article publié dans une revue avec comité d'évaluation
Pages:p. 168-174
Version évaluée par les pairs:Oui
Identifiant unique:10.1002/mrc.4328
Sujets:Sciences naturelles et génie > Sciences naturelles > Chimie
Département, module, service et unité de recherche:Départements et modules > Département des sciences fondamentales
Mots-clés:NMR, pergalloylatd tannins, gallic acid, glycosides
Déposé le:01 sept. 2021 18:44
Dernière modification:01 sept. 2021 18:44
Afficher les statistiques de telechargements

Éditer le document (administrateurs uniquement)

Creative Commons LicenseSauf indication contraire, les documents archivés dans Constellation sont rendus disponibles selon les termes de la licence Creative Commons "Paternité, pas d'utilisation commerciale, pas de modification" 2.5 Canada.

Bibliothèque Paul-Émile-Boulet, UQAC
555, boulevard de l'Université
Chicoutimi (Québec)  CANADA G7H 2B1
418 545-5011, poste 5630