Balsacones D-I, dihydrocinnamoyl flavans from Populus balsamifera buds.
A phytochemical investigation of an ethanolic extract from Populus balsamifera L. buds resulted in the isolation and characterization of twelve new flavan derivatives consisting of six pairs of enantiomers. Structures of (+) and (-)-balsacones D-I were elucidated based on spectroscopic data (1D and 2D NMR, MS) and their absolute configurations were established using X-ray single crystal diffraction analysis and ECD computational calculations. Antibacterial activity and cytotoxicity of all purified enantiomers were evaluated in vitro against Staphylococcus aureus and human skin fibroblast cells, respectively.
Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Département des sciences fondamentales, Université du Québec à Chicoutimi, Québec G7H 2B1, Canada.
François
F
Simard
Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Département des sciences fondamentales, Université du Québec à Chicoutimi, Québec G7H 2B1, Canada.
Jean
J
Legault
Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Département des sciences fondamentales, Université du Québec à Chicoutimi, Québec G7H 2B1, Canada.
Serge
S
Lavoie
Laboratoire d'Analyse et de Séparation des Essences Végétales (LASEVE), Département des sciences fondamentales, Université du Québec à Chicoutimi, Québec G7H 2B1, Canada. Electronic address: andre_pichette@uqac.ca.
André
A
Pichette
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D001578:Benzopyrans / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology* / Q000633:toxicity; D005347:Fibroblasts / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D018520:Plant Shoots / Q000737:chemistry*; D032107:Populus / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D001578:Benzopyrans
Antibacterial activity; Balsacone; Bud; Chiral separation; Circular dichroism; Computational calculations; Dihydrochalcone; Flavan; Populus balsamifera L.; Salicaceae; Staphylococcus aureus