title: Structure elucidation of anti-methicillin resistant Staphylococcus aureus (MRSA) flavonoids from balsam poplar buds.
abstract: There is nowadays an urgent need for developing novel generations of antibiotic agents due to the increased resistance of pathogenic bacteria. As a rich reservoir of structurally diverse compounds, plant species hold promise in this regard. Within this framework, we isolated a unique series of antibacterial flavonoids, named balsacones N-U, featuring multiple cinnamyl chains on the flavan skeleton. The structures of these compounds, isolated as racemates, were determined using extensive 1D and 2D NMR analysis in tandem with HRMS. Balsacones N-U along with previously isolated balsacones A-M were evaluated for their antibacterial activity against clinical isolates of methicillin resistant Staphylococcus aureus (MRSA). Several of the tested balsacones were potent anti-MRSA agents showing MIC values in the low micromolar range. Structure-activity relationships study highlighted some important parameters involved in the antibacterial activity of balsacones such as the presence of cinnamyl and cinnamoyl chains at the C-3 and C-8 positions of the flavan skeleton, respectively. These results suggest that balsacones could represent a potential novel class of naturally occurring anti-MRSA agents.
authors.affiliation: Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.
authors.forename: François
authors.initials: F
authors.lastname: Simard
authors.affiliation: Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada; INRS-Institut Armand-Frappier, Université du Québec, 531 boul. des Prairies, Laval (Québec) H7V 1B7, Canada.
authors.forename: Charles
authors.initials: C
authors.lastname: Gauthier
authors.affiliation: Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.
authors.forename: Jean
authors.initials: J
authors.lastname: Legault
authors.affiliation: Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.
authors.forename: Serge
authors.initials: S
authors.lastname: Lavoie
authors.affiliation: Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada.
authors.forename: Vakhtang
authors.initials: V
authors.lastname: Mshvildadze
authors.affiliation: Laboratoire LASEVE, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555, boul. de l'Université, Chicoutimi (Québec) G7H 2B1, Canada. Electronic address: andre_pichette@uqac.ca.
authors.forename: André
authors.initials: A
authors.lastname: Pichette
mesh_terms: D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D002934:Cinnamates / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005419:Flavonoids / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005839:Gentamicins / Q000494:pharmacology; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects* / Q000302:isolation & purification; D008958:Models, Molecular; D032107:Populus / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D002934:Cinnamates; D005419:Flavonoids; D005839:Gentamicins
keywords: Anti-MRSA; Antibacterial activity; Balsacones; Dihydrochalcones; Flavonoids; Structure–activity relationships