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RESEARCH ARTICLE
Contents Vol 73(3)

A Sesquiterpene Isonitrile with a New Tricyclic Skeleton from the Indo-Pacific Nudibranch Phyllidiella pustulosa: Spectroscopic and Computational Studies

Desmond C.-M. Sim A , Natasha L. Hungerford A , Elizabeth H. Krenske A , Gregory K. Pierens B , Katherine T. Andrews C , Tina S. Skinner-Adams C and Mary J. Garson A D
+ Author Affiliations
- Author Affiliations

A School of Chemistry and Molecular Biosciences, The University of Queensland, St Lucia, Qld 4072, Australia.

B Centre for Advanced Imaging, The University of Queensland, St Lucia, Qld 4072, Australia.

C Griffith Institute for Drug Discovery, Griffith University, Nathan, Qld 4111, Australia.

D Corresponding author. Email: m.garson@uq.edu.au

Australian Journal of Chemistry 73(3) 129-136 https://doi.org/10.1071/CH19227
Submitted: 22 May 2019  Accepted: 1 July 2019   Published: 7 August 2019

Abstract

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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