Chromolactol, an Oxygenated Diterpene from the Indo-Pacific Nudibranch Goniobranchus coi: Spectroscopic and Computational Studies*

Ariyanti S. Dewi; Gregory K. Pierens; Karen L. Cheney; Joanne T. Blanchfield; Mary J. Garson

doi:10.1071/CH18243

RESEARCH ARTICLE

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Chromolactol, an Oxygenated Diterpene from the Indo-Pacific Nudibranch Goniobranchus coi: Spectroscopic and Computational Studies*

Ariyanti S. Dewi ^A ^B , Gregory K. Pierens ^C , Karen L. Cheney ^D , Joanne T. Blanchfield ^A and Mary J. Garson ^A ^E

+ Author Affiliations

- Author Affiliations

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

^B Research Center for Marine and Fisheries Product Processing and Biotechnology, Ministry of Marine Affairs and Fisheries, Jakarta 10260, Indonesia.

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

^D School of Biological Sciences, The University of Queensland, Brisbane, Qld 4072, Australia.

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

Australian Journal of Chemistry 71(10) 798-803 https://doi.org/10.1071/CH18243
Submitted: 23 May 2018 Accepted: 1 July 2018 Published: 1 August 2018

Abstract

A rearranged spongian diterpene chromolactol was obtained from the mantle extract of the Indo-Pacific nudibranch Goniobranchus coi. The structure of chromolactol, either 1a or 1b, which was investigated by extensive NMR experiments and by data comparison as well as by molecular modelling studies and density functional calculations, has a different relative configuration of the 2,8-dioxabicyclo-[3.3.0]-octane ring compared with the co-metabolite norrisolide (2). A biosynthetic pathway leading to the preferred diastereomer of chromolactol (1a) is presented.

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