Discovery of Ircinianin Lactones B and C-Two New Cyclic Sesterterpenes from the Marine Sponge Ircinia wistarii

发现 Ircinianin 内酯 B 和 C-来自海洋海绵 Ircinia wistarii 的两个新环状二萜

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作者:Thomas Majer, Keshab Bhattarai, Jan Straetener, Justus Pohlmann, Patrick Cahill, Markus O Zimmermann, Marc P Hübner, Marcel Kaiser, Johan Svenson, Michael Schindler, Heike Brötz-Oesterhelt, Frank M Boeckler, Harald Gross1

Abstract

Two new ircinianin-type sesterterpenoids, ircinianin lactone B and ircinianin lactone C (7 and 8), together with five known entities from the ircinianin compound family (1, 3-6) were isolated from the marine sponge Ircinia wistarii. Ircinianin lactones B and C (7 and 8) represent new ircinianin terpenoids with a modified oxidation pattern. Despite their labile nature, the structures could be established using a combination of spectroscopic data, including HRESIMS and 1D/2D NMR techniques, as well as computational chemistry and quantum-mechanical calculations. In a broad screening approach for biological activity, the class-defining compound ircinianin (1) showed moderate antiprotozoal activity against Plasmodium falciparum (IC50 25.4 μM) and Leishmania donovani (IC50 16.6 μM).

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