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.
Xiao
Zhi Yong
ZY
School of Pharmacy, Fudan University, Shanghai 200032, People's Republic of China.
Mu
Qing
Q
Shiu
Winnie Ka Po
WK
Zeng
Yi Han
YH
Gibbons
Simon
S
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification; D016227:Benzoquinones / Q000737:chemistry / Q000302:isolation & purification; D018360:Crystallography, X-Ray; D024901:Drug Resistance, Multiple, Bacterial / Q000187:drug effects; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D020902:Hypericum / Q000737:chemistry*; D016106:Methicillin Resistance / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D009643:Norfloxacin / Q000494:pharmacology; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000235:genetics / Q000378:metabolism
C118110:7-epiclusianone; D000900:Anti-Bacterial Agents; D001577:Benzophenones; D016227:Benzoquinones; D004365:Drugs, Chinese Herbal; D010696:Phloroglucinol; D009643:Norfloxacin