Structural diversity in nudibranch chemistry: elucidation of norditerpenes with a dendrillane scaffold from the Australian nudibranch Goniobranchus coi

Louise C. Forster; Gregory K. Pierens; James J. De Voss; Mary J. Garson

doi:10.1071/CH24073

RESEARCH ARTICLE (Open Access)

Next Contents Vol 77(7)

Structural diversity in nudibranch chemistry: elucidation of norditerpenes with a dendrillane scaffold from the Australian nudibranch Goniobranchus coi

Louise C. Forster

^A ^B , Gregory K. Pierens

^C , James J. De Voss

^A and Mary J. Garson

^A ^*

+ Author Affiliations

- Author Affiliations

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

^B School of Environmental and Life Sciences, The University of Newcastle, Callaghan, NSW 2308, Australia.

^C Centre for Advanced Imaging, The University of Queensland, Brisbane, Qld 4072, Australia.

^* Correspondence to: m.garson@uq.edu.au

Handling Editor: Curt Wentrup

Australian Journal of Chemistry 77, CH24073 https://doi.org/10.1071/CH24073

Submitted: 27 May 2024 Accepted: 19 June 2024 Published online: 9 July 2024

© 2024 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

In addition to three known compounds (1–3), two new rearranged spongian diterpenes (4 and 5) with perhydroazulene and dioxabicyclooctane ring systems were isolated from the mantle and viscera of the Australian nudibranch Goniobranchus coi. The relative configuration of the major spiroepoxide 4 was explored by comparison with those of m-chloroperbenzoic acid oxidation products derived from dendrillolide A (1). Aldehydes 6 and 7 were identified as the ring-opened artefacts of the spiroepoxides 5 and 4 respectively, and yielded ketone 3 on storage. The relative configurations of lactols 8 and 9, isolated as an inseparable mixture of diastereomers, were deduced by molecular modelling and computational studies. Acetylation of the lactol mixture provided dendrillolide A (1), further confirming the structural assignments of 8 and 9. Dissection of animal tissue established that the norditerpenoid metabolites were present in both mantle and viscera tissues.

Keywords: dendrillolide, density functional calculations, epoxide, lactol, NMR spectroscopy, norditerpene, nudibranch, perhydroazulene, relative configuration.

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