Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros.

Chianese, Giuseppina, Silber, Johanna, Luciano, Paolo, Merten, Christian, Erpenbeck, Dirk, Topaloglu, Bülent, Kaiser, Marcel and Tasdemir, Deniz (2017) Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros. Journal of Natural Products, 80 (9). pp. 2566-2571. DOI 10.1021/acs.jnatprod.7b00543.

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Abstract

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 [α]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 μM). This is the second report of rare glycinyl lactam derivatives 3 and 4 from the genus Ircinia.

Document Type: Article
Research affiliation: OceanRep > GEOMAR > Applied R&D > GEOMAR-Biotech
Kiel University
OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MN Marine natural products chemistry
Refereed: Yes
Open Access Journal?: No
DOI etc.: 10.1021/acs.jnatprod.7b00543
ISSN: 0163-3864
Projects: RESOLV
Date Deposited: 07 Sep 2017 10:33
Last Modified: 01 Feb 2019 15:01
URI: http://oceanrep.geomar.de/id/eprint/39283

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