Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata
Author(s)
White, Andrew M
Pierens, Gregory K
Skinner-Adams, Tina
Andrews, Katherine T
Bernhardt, Paul V
Krenske, Elizabeth H
Mollo, Ernesto
Garson, Mary J
Year published
2015
Metadata
Show full item recordAbstract
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.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.
View less >
View less >
Journal Title
Journal of Natural Products
Volume
78
Issue
6
Subject
Chemical sciences
Biological sciences
Other biological sciences not elsewhere classified
Biomedical and clinical sciences
Traditional, complementary and integrative medicine