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Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks
Andrew M White1, Gregory K Pierens1, Louise C Forster1
1School of Chemistry and Molecular Biosciences, ‡School of Biological Sciences, and §Centre of Advanced Imaging, The University of Queensland , Brisbane, QLD 4072, Australia.
Abstract:
Three new norditerpenes (1, 6, and 7) and four diterpenes (2-5) with extensively rearranged carbon skeletons have been characterized from Australian nudibranchs. The relative configuration of the cyclopropyl-containing verrielactone (1) from Goniobranchus verrieri was suggested by spectroscopic analysis at 500 MHz informed by a combination of molecular modeling and DFT calculations. The nudibranchs G. splendidus and G. cf. splendidus provided 2-7, for which the structures and stereochemistry were deduced by 2D NMR studies at either 500 or 700 MHz. Each of the seven terpenoids exhibited a carbon skeleton modified from one of the tetrahydroaplysulphurin, spongionellin, or gracilane series of terpenes. A biosynthetic pathway to terpenes 1-7 from spongialactone is proposed.
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