Watsonianone A–C, anti-plasmodial β-triketones from the Australian tree, Corymbia watsoniana
Author(s)
Carroll, Anthony R
Avery, Vicky M
Duffy, Sandra
Forster, Paul I
Guymer, Gordon P
Year published
2013
Metadata
Show full item recordAbstract
Three new ߭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 ߭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 ...
View more >Three new ߭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 ߭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 占vs. Pf 3D7) demonstrating significant selectivity against the human cell line, HEK 293 (>400 ש. Stage specificity studies indicate that watsonianone B is predominantly active against young ring stages of P. falciparum.
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View more >Three new ߭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 ߭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 占vs. Pf 3D7) demonstrating significant selectivity against the human cell line, HEK 293 (>400 ש. Stage specificity studies indicate that watsonianone B is predominantly active against young ring stages of P. falciparum.
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Journal Title
Organic & Biomolecular Chemistry
Volume
11
Issue
3
Subject
Medicinal and biomolecular chemistry
Biologically active molecules
Organic chemistry