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RESEARCH ARTICLE
Contents Vol 73(10)

Arenaran Sesquiterpenes from the Nudibranch Chromodoris strigata and its Dietary Sponge Acanthodendrilla sp. 2510: Spectroscopic and Computational Studies

Patrick T. Narbutas A , Jack K. Clegg https://orcid.org/0000-0002-7140-5596 A , Gregory K. Pierens B , Karen L. Cheney C D , Anna M. Ganderton A and Mary J. Garson https://orcid.org/0000-0001-8670-1075 A E
+ 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 School of Biological Sciences, The University of Queensland, St Lucia, Qld 4072, Australia.

D Queensland Brain Institute, The University of Queensland, St Lucia, Qld 4072, Australia.

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

Australian Journal of Chemistry 73(10) 948-955 https://doi.org/10.1071/CH19540
Submitted: 22 October 2019  Accepted: 28 November 2019   Published: 9 April 2020

Abstract

Oxygenated sesquiterpenes were isolated from the sponge Acanthodendrilla sp. 2510 and identified as caparrapi oxide (1) and the bioactive oxocene sesquiterpene, arenaran A (2). An extract of the nudibranch Chromodoris strigata, found feeding on the sponge, also contained 2. Also characterized from the sponge extract were three compounds 3–5 derived from the oxocene skeleton of arenaran A that possessed hydroperoxy functionality. The structure and stereochemistry of each compound was identified using 1D and 2D NMR spectroscopic and mass spectrometry techniques, in combination with X-ray crystallography and molecular modelling/computational studies. Isolation of the hydroperoxy products provided insight into the reactivity of the oxocene skeleton.


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