np5b00155_si_001.pdf (624.9 kB)

Antibacterial Balsacones J–M, Hydroxycinnamoylated Dihydrochalcones from Populus balsamifera Buds

Download (624.9 kB)
journal contribution
posted on 22.05.2015, 00:00 by François Simard, Charles Gauthier, Éric Chiasson, Serge Lavoie, Vakhtang Mshvildadze, Jean Legault, André Pichette
A phytochemical investigation of buds from the hardwood tree Populus balsamifera led to the isolation of six new cinnamoylated dihydrochalcones as pairs of racemates and one as a racemic mixture along with the known compound iryantherin-D (2), the absolute configuration of which was determined for the first time. The structures of balsacones J (1), K (3), L (4), and M (5) were elucidated on the basis of spectroscopic data (1D and 2D NMR, IR, and MS). Chiral HPLC separations were carried out, and the absolute configuration of the isolated enantiomers unambiguously established via X-ray diffraction analyses and electron circular dichroism spectroscopic data. Each of the purified enantiomers exhibited potent in vitro antibacterial activity against Staphylococcus aureus with IC50 values ranging from 0.61 to 6 μM.