Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks.

White, Andrew M., Pierens, Gregory K., Forster, Louise C., Winters, Anne E., Cheney, Karen L. and Garson, Mary J. (2015) Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks.. Journal of Natural Products, 79 3: 477-483. doi:10.1021/acs.jnatprod.5b00866


Author White, Andrew M.
Pierens, Gregory K.
Forster, Louise C.
Winters, Anne E.
Cheney, Karen L.
Garson, Mary J.
Title Rearranged Diterpenes and Norditerpenes from Three Australian Goniobranchus Mollusks.
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 1520-6025
0163-3864
Publication date 2015-12-23
Year available 2015
Sub-type Article (original research)
DOI 10.1021/acs.jnatprod.5b00866
Open Access Status Not yet assessed
Volume 79
Issue 3
Start page 477
End page 483
Total pages 7
Place of publication Washington, DC, United States
Publisher American Chemical Society
Collection year 2016
Language eng
Formatted 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.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status UQ

 
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Created: Fri, 15 Jan 2016, 11:43:06 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences