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

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White, Andrew M
Pierens, Gregory K
Skinner-Adams, Tina
Andrews, Katherine T
Bernhardt, Paul V
Krenske, Elizabeth H
Mollo, Ernesto
Garson, Mary J
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2015
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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.

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Journal of Natural Products

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78

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6

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Chemical sciences

Biological sciences

Other biological sciences not elsewhere classified

Biomedical and clinical sciences

Traditional, complementary and integrative medicine

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