Journal
AUSTRALIAN JOURNAL OF CHEMISTRY
Volume 73, Issue 2-3, Pages 129-136Publisher
CSIRO PUBLISHING
DOI: 10.1071/CH19227
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Funding
- University of Queensland (School of Chemistry and Molecular Biosciences)
- Australian Pacific Science Foundation
- Australian Research Council [DP150103131, 180103047]
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The sesquiterpene isonitrile, 9-isocyanoneoallopupukeanane 1, has been obtained from the Indo-Pacific nudibranch Phyllidiella pustulosa. The structure of 1, which was investigated by extensive NMR experiments, molecular modelling studies, and density functional calculations, has a different arrangement of the tricyclic ring system compared with other isonitrile metabolites isolated from nudibranchs or sponges. The viability of a biosynthetic pathway leading to 1, proposed to involve a series of carbocation rearrangements, is explored in a computational study. Isonitrile 1 exhibited micromolar antimalarial activity when screened against Plasmodium falciparum infected erythrocytes.
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