2. Academic Validation
  3. Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros

Antiprotozoal Linear Furanosesterterpenoids from the Marine Sponge Ircinia oros

  • J Nat Prod. 2017 Sep 22;80(9):2566-2571. doi: 10.1021/acs.jnatprod.7b00543.
Giuseppina Chianese 1,  Johanna Silber 1,  Paolo Luciano 2,  Christian Merten 3,  Dirk Erpenbeck 4,  Bülent Topaloglu 5,  Marcel Kaiser 6 7,  Deniz Tasdemir 1
Affiliations

Affiliations

  • 1 GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel , Kiel 24106, Germany.
  • 2 Department of Pharmacy, University of Naples Federico II , Naples 80131, Italy.
  • 3 Lehrstuhl für Organische Chemie 2, Ruhr-Universität Bochum , Bochum 44801, Germany.
  • 4 Department of Earth and Environmental Sciences and GeoBio-Center, Ludwig-Maximilians-Universität München , 80333 München, Germany.
  • 5 Department of Marine Biology, Faculty of Fisheries, Istanbul University , Istanbul TR-34480, Turkey.
  • 6 Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute , Basel CH-4002, Switzerland.
  • 7 University of Basel , Basel CH-4003, Switzerland.
PMID: 28840725 DOI: 10.1021/acs.jnatprod.7b00543
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.

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