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Chianese, Giuseppina; Silber, Johanna; Luciano, Paolo; Merten, Christian; Erpenbeck, Dirk; Topaloglu, Bülent; Kaiser, Marcel; Tasdemir, Deniz (2017): Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros. In: Journal of Natural Products, Vol. 80, No. 9: pp. 2566-2571
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Chemical investigation of the marine sponge Ircinia oros yielded four linear furanosesterterpenoids, including the known metabolites ircinin-1 (1) and ircinin-2 (2) and two new compounds, ircinialactam E (3) and ircinialactam F (4). Their chemical structures were elucidated by using a combination of [alpha](D), NMR, HRMS, and FT-IR spectroscopy. The absolute configuration of C-18 in compounds 1-3 was identified as R by electronic circular dichroism (ECD) spectroscopy coupled with time-dependent density functional theory calculations. Compounds 1-4 showed moderate leishmanicidal, trypanocidal, and antiplasmodial activities (IC50 values 28-130 mu M). This is the second report of rare glycinyl lactam derivatives 3 and 4 from the genus Ircinia.