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Antiplasmodial β-Triketone-Flavanone Hybrids from the Flowers of the Australian Tree Corymbia torelliana.
Journal of Natural Products 2018 July 28
The methanol extract of the flowers of the Australian eucalypt tree Corymbia torelliana yielded six new β-triketone-flavanone hybrids, torellianones A-F (1-6), the tetrahydroxycyclohexane torellianol A (7), and known β-triketones (4 S)-ficifolidione (8) and (4 R)-ficifolidione (9), and β-triketone-flavanones kunzeanone A (10) and kunzeanone B (11). Torellianones A and B, C and D, and E and F were each isolated as inseparable diastereomeric mixtures. Exchange correlations observed in a ROESY spectrum indicated that 5 and 6 also interconverted between stable conformers. The structures of 1-7 were elucidated from the analysis of 1D/2D NMR and MS data. Relative configurations of torellianones C-F and torrellianol A were determined from analysis of ROESY data. Compounds 1-10 were tested for antiplasmodial activity against a drug-sensitive (3D7) strain of Plasmodium falciparum, with 3-6 and 8-10 showing limited antiplasmodial activity, with IC50 values ranging from 3.2 to 16.6 μM.
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