Antimalarial isocyano and isothiocyanato sesquiterpenes with tri- and bicyclic skeletons from the nudibranch Phyllidia ocellata

White, Andrew M., Pierens, Gregory K., Skinner-Adams, Tina, Andrews, Katherine T., Bernhardt, Paul V., Krenske, Elizabeth H., Mollo, Ernesto and Garson, Mary J. (2015) Antimalarial isocyano and isothiocyanato sesquiterpenes with tri- and bicyclic skeletons from the nudibranch Phyllidia ocellata. Journal of Natural Products, 78 6: 1422-1427. doi:10.1021/acs.jnatprod.5b00354


Author White, Andrew M.
Pierens, Gregory K.
Skinner-Adams, Tina
Andrews, Katherine T.
Bernhardt, Paul V.
Krenske, Elizabeth H.
Mollo, Ernesto
Garson, Mary J.
Title Antimalarial isocyano and isothiocyanato sesquiterpenes with tri- and bicyclic skeletons from the nudibranch Phyllidia ocellata
Formatted title
Antimalarial isocyano and isothiocyanato sesquiterpenes with tri- and bicyclic skeletons from the nudibranch Phyllidia ocellata
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 1520-6025
0163-3864
Publication date 2015-06-26
Sub-type Article (original research)
DOI 10.1021/acs.jnatprod.5b00354
Volume 78
Issue 6
Start page 1422
End page 1427
Total pages 6
Place of publication Washington, DC United States
Publisher American Chemical Society
Collection year 2016
Language eng
Formatted abstract
Five new isocyano/isothiocyanato sesquiterpenes (1–5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26–0.30 μM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 μM.
Keyword Phyllidia ocellata
Plasmodium falciparum
Metabolites
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
School of Chemistry and Molecular Biosciences
Centre for Advanced Imaging Publications
 
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