Polyisoprenylated benzoylphloroglucinol derivatives from Hypericum sampsonii

Bioassay-directed fractionation using multidrug-resistant (MDR) Staphylococcus aureus resulted in the isolation of four new polyprenylated benzophloroglucinol derivatives, sampsoniones N-Q (1-4), and four known compounds, 7-epiclusianone (5) and sampsoniones B, L, and R, from the roots of Hypericum sampsonii. The structures of these compounds were established by analysis of spectroscopic data, and the structures of 4 and 5 were determined by single-crystal X-ray diffraction crystallography. In the bioassay, 7-epiclusianone (5) showed promising activity with a minimum inhibitory concentration (MIC) of 7.3 microM against the NorA overexpressing MDR S. aureus strain SA-1199B; the positive control antibiotic norfloxacin showed activity at MIC 100 microM.