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Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks

Journal of Natural Products, ISSN: 1520-6025, Vol: 79, Issue: 3, Page: 477-483
2016
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Article Description

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.

Bibliographic Details

Andrew M. White; Louise C. Forster; Mary J. Garson; Anne E. Winters; Karen L. Cheney; Gregory K. Pierens

American Chemical Society (ACS)

Chemistry; Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Medicine

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