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Issue 3, 2013
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Watsonianone A–C, anti-plasmodial β-triketones from the Australian tree, Corymbia watsoniana

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Abstract

Three new β-triketones, watsonianones A–C, and the known compound corymbone B were isolated from the flowers of the Australian eucalypt Corymbia watsoniana. Watsonianone A is the first naturally occurring methylene bridged bis-tetramethylcyclohexatrione, watsonianone B is only the fourth fused bisfurano β-triketone and watsonianone C is the first 4,4a,9,9a-tetrahydro-2H-xanthene-1,3,5,7(6H,8H)-tetraone to be reported in the literature. MS and NMR analysis established the structures of the new compounds. All three new compounds showed anti-plasmodial activity against chloroquine resistant (Dd2) and sensitive strains (3D7) of the parasite, Plasmodium falciparum, responsible for malarial infections. Watsonianone B was the most potent inhibitor (IC50 0.289 μM vs. Pf 3D7) demonstrating significant selectivity against the human cell line, HEK 293 (>400 ×). Stage specificity studies indicate that watsonianone B is predominantly active against young ring stages of P. falciparum.

Graphical abstract: Watsonianone A–C, anti-plasmodial β-triketones from the Australian tree, Corymbia watsoniana

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Publication details

The article was received on 02 Oct 2012, accepted on 22 Nov 2012 and first published on 22 Nov 2012


Article type: Paper
DOI: 10.1039/C2OB26931G
Org. Biomol. Chem., 2013,11, 453-458

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    Watsonianone A–C, anti-plasmodial β-triketones from the Australian tree, Corymbia watsoniana

    A. R. Carroll, V. M. Avery, S. Duffy, P. I. Forster and G. P. Guymer, Org. Biomol. Chem., 2013, 11, 453
    DOI: 10.1039/C2OB26931G

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