Bioactive acylphloroglucinols from Hypericum densiflorum.
Three acylphloroglucinol derivatives have been isolated from the hexane and acetone extracts of the aerial parts of Hypericum densiflorum Pursch. The compounds were characterized by NMR spectroscopy and mass spectrometry and identified as 4-geranyloxy-2,6-dihydroxybenzophenone (1), 4-geranyloxy-1-(2-methylpropanoyl)- phloroglucinol (2) and 4-geranyloxy-1-(2-methylbutanoyl)-phloroglucinol (3). Compounds 1-3 were evaluated for in vitro cell proliferation inhibitory activity against human breast (MCF-7), lung (NCI H460), CNS (SF-268), stomach (AGS) and colon (HCT-116) tumor cell lines; antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA); inhibition of cyclooxygenase (COX-1 and -2) enzymes; and antioxidant activity in the lipid peroxidation (LPO) assay. All three compounds showed moderate to strong antitumor, antibacterial, antioxidant and inhibition of COX-2 activities. Also, this is the first reported occurrence of compound 3 in the Hypericum genus.
Department of Chemistry, Susquehanna University, Selinsgrove, PA 17870, USA. henry@susqu.edu
Geneive E
GE
Henry
Matthew S
MS
Campbell
Ashlee A
AA
Zelinsky
Yunbao
Y
Liu
Camile S
CS
Bowen-Forbes
Liya
L
Li
Muraleedharan G
MG
Nair
David C
DC
Rowley
Navindra P
NP
Seeram
D000900:Anti-Bacterial Agents / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology; D000975:Antioxidants / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D016861:Cyclooxygenase Inhibitors / Q000494:pharmacology; D006801:Humans; D020902:Hypericum / Q000737:chemistry*; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology*
C546529:4-geranyloxy-1-(2-methylbutanoyl)phloroglucinol; C546528:4-geranyloxy-1-(2-methylpropanoyl)phloroglucinol; C546527:4-geranyloxy-2,6-dihydroxybenzophenone; D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D000975:Antioxidants; D016861:Cyclooxygenase Inhibitors; D010696:Phloroglucinol