title: Antibacterial acylphloroglucinols from Hypericum olympicum.
abstract: New antibacterial acylphloroglucinols (1-5) were isolated and characterized from the aerial parts of the plant Hypericum olympicum L. cf. uniflorum. The structures of these compounds were confirmed by extensive 1D- and 2D-NMR experiments to be 4,6-dihydroxy-2-O-(3″,7″-dimethyl-2″,6″-octadienyl)-1-(2'-methylbutanoyl)benzene (1), 4,6-dihydroxy-2-O-(7″-hydroxy-3″,7″-dimethyl-2″,5″-octadienyl)-1-(2'-methylbutanoyl)benzene (2), 4,6-dihydroxy-2-O-(6″-hydroxy-3″,7″-dimethyl-2″,7″-octadienyl)-1-(2'-methylbutanoyl)benzene (3), 4,6-dihydroxy-2-O-(6″-hydroperoxy-3″,7″-dimethyl-2″,7″-octadienyl)-1-(2'-methylbutanoyl)benzene (4), and 4,6-dihydroxy-2-O-(6″,7″-epoxy-3″,7″-dimethyloct-2″-enyl)-1-(2'-methylbutanoyl)benzene (5). These new natural products have been given the trivial names olympicins A-E (1-5). All compounds were evaluated against a panel of methicillin-resistant Staph. aureus and multidrug-resistant strains of Staph. aureus. Compound 1 exhibited minimum inhibitory concentrations (MICs) of 0.5-1 mg/L against the tested Staph. aureus strains. Compounds 2 to 5 were also shown to be active, with MICs ranging from 64 to 128 mg/L. Compound 1 was synthesized using a simple four-step method that can be readily utilized to give a number of structural analogues of 1.
authors: Department of Pharmaceutical and Biological Chemistry, The School of Pharmacy, University of London, 29-39 Brunswick Square, London WC1N 1AX, UK.
authors: Winnie K P
authors: WK
authors: Shiu
authors: M Mukhlesur
authors: MM
authors: Rahman
authors: Jonathan
authors: J
authors: Curry
authors: Paul
authors: P
authors: Stapleton
authors: Mire
authors: M
authors: Zloh
authors: John P
authors: JP
authors: Malkinson
authors: Simon
authors: S
authors: Gibbons
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D020902:Hypericum / Q000737:chemistry*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; C571760:olympicin A; D010696:Phloroglucinol