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β-Triketone–Monoterpene Hybrids from the Flowers of the Australian Tree Corymbia intermedia

Author:
Senadeera, Sarath P. D., Robertson, Luke P., Duffy, Sandra, Wang, Yun, Avery, Vicky M., Carroll, Anthony R.
Source:
Journal of natural products 2018 v.81 no.11 pp. 2455-2461
ISSN:
1520-6025
Subject:
Corymbia intermedia, Eucalyptus, Plasmodium falciparum, antiplasmodial properties, flowers, inhibitory concentration 50, moieties, monoterpenoids, nuclear magnetic resonance spectroscopy, trees
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.
Agid:
6225220