β-Triketone-Monoterpene Hybrids from the Flowers of the Australian Tree Corymbia intermedia
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Robertson, Luke P
Duffy, Sandra
Wang, Yun
Avery, Vicky M
Carroll, Anthony R
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Abstract
Four new β-triketone monoterpene hybrids, intermediones A–D (1–4), have been identified from the flowers of the Australian eucalypt tree Corymbia intermedia. Intermediones A–D are β-triketones that incorporate a pinene moiety attached via a benzyl group to a syncarpic acid. The structures of 1–4, including relative configurations, were elucidated from the analysis of 1D/2D NMR and MS data. The absolute configurations of intermediones A and B were determined by comparison of experimental and predicted ECD spectra. Intermedione D possesses a tetracyclic ring system that is related to that found in the meroterpenes, guadials B and C. Low to moderate antiplasmodial activity toward the chloroquine-sensitive (3D7) strain of Plasmodium falciparum, with IC50 values ranging from 9.9 to 20.8 μM, was observed for intermediones A, B, and D.
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Journal of Natural Products
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81
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11
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Chemical sciences
Other chemical sciences not elsewhere classified
Biological sciences
Biomedical and clinical sciences
Traditional, complementary and integrative medicine