Cytotoxic Spiroepoxide Lactone and Its Putative Biosynthetic Precursor from Goniobranchus Splendidus
Louise C Forster1, Gregory K Pierens1, Andrew M White1
1School of Chemistry and Molecular Biosciences, Centre for Advanced Imaging, School of Biological Sciences, and Institute for Molecular Bioscience, The University of Queensland, Brisbane, 4072 QLD, Australia.
Abstract:
Epoxygoniolide-1 (1), possessing spiroepoxide lactone, enal, and masked dialdehyde functionalities, has been characterized from the conspicuously patterned mollusc Goniobranchus splendidus. Its relative configuration was investigated by spectroscopic analyses, molecular modeling, and density functional theory calculations. The biosynthesis of 1 may involve rearrangement of a diterpene framework, providing a precursor to cometabolite gonioline (2), followed by C-C bond cleavage (via Grob or P450 mechanism). Moderate cytotoxicity to NCIH-460, SW60, or HepG2 cancer cells was observed for norditerpene 1.
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