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

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• 作者：Andrew M. White ; Gregory K. Pierens ; Tina Skinner-Adams ; Katherine T. Andrews ; Paul V. Bernhardt ; Elizabeth H. Krenske ; Ernesto Mollo ; Mary J. Garson
• 刊名：Journal of Natural Products
• 出版年：2015
• 出版时间：June 26, 2015
• 年：2015
• 卷：78
• 期：6
• 页码：1422-1427
• 全文大小：316K
• ISSN：1520-6025

文摘

Five new isocyano/isothiocyanato sesquiterpenes (1鈥?b>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鈥?.30 渭M), while isothiocyanate 3 and formamide 6 had IC₅₀ values of >10 渭M.