Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata

Andrew M. White, Gregory K. Pierens, Tina Skinner-Adams, Katherine T. Andrews, Paul V. Bernhardt, Elizabeth H. Krenske, Ernesto Mollo, Mary J. Garson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1422-1427
Number of pages6
JournalJournal of Natural Products
Volume78
Issue number6
DOIs
Publication statusPublished - 26 Jun 2015
Externally publishedYes

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