Antibacterial acylphloroglucinols from Hypericum olympicum

Shiu, Winnie K. P., Rahman, M. Mukhlesur, Curry, Jonathan, Stapleton, Paul, Zloh, Mire, Malkinson, John P. and Gibbons, Simon (2012) Antibacterial acylphloroglucinols from Hypericum olympicum. Journal of Natural Products, 75 (3). pp. 336-343. ISSN 0163-3864

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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.

Item Type: Article
Uncontrolled Keywords: analytical chemistry,molecular medicine,pharmacology,pharmaceutical science,drug discovery,complementary and alternative medicine,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602
Faculty \ School: Faculty of Science > School of Pharmacy
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Depositing User: LivePure Connector
Date Deposited: 15 Jul 2020 23:38
Last Modified: 22 Oct 2022 06:29
DOI: 10.1021/np2003319

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