Futunamine, a Pyrrole-Imidazole Alkaloid from the Sponge Stylissa aff. carteri Collected off the Futuna Islands.

The chemical investigation of the sponge Stylissa aff. carteri collected around Futuna Islands in the Pacific Ocean led to the isolation of three new dimeric pyrrole 2-aminoimidazole alkaloids (PIAs). Futunamine (1) features an unprecedented pyrrolo[1,2-c]imidazole core, while two other new dimeric PIAs were identified as analogues of palau'amine. Together with other known PIAs isolated from this species, they were shown to exhibit anti-inflammatory and neuroprotective activities.

[1]  S. Sunagawa,et al.  The Tara Pacific expedition—A pan-ecosystemic approach of the “-omics” complexity of coral reef holobionts across the Pacific Ocean , 2019, PLoS Biology.

[2]  F. Totzke,et al.  Bioactive pyrrole alkaloids isolated from the Red Sea: marine sponge Stylissa carteri , 2018, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[3]  T. Lindel.  Chemistry and Biology of the Pyrrole-Imidazole Alkaloids. , 2017, The Alkaloids. Chemistry and biology.

[4]  Wael E Houssen,et al.  Gracilins: Spongionella-derived promising compounds for Alzheimer disease , 2015, Neuropharmacology.

[5]  P. Baran,et al.  Asymmetric syntheses of sceptrin and massadine and evidence for biosynthetic enantiodivergence , 2014, Science.

[6]  G. Bringmann,et al.  SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. , 2013, Chirality.

[7]  T. Molinski,et al.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica. , 2012, Angewandte Chemie.

[8]  R. Jeffree,et al.  New Insight into Marine Alkaloid Metabolic Pathways: Revisiting Oroidin Biosynthesis , 2011, Chembiochem : a European journal of chemical biology.

[9]  D. Romo,et al.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids. , 2011, Natural product reports.

[10]  M. Köck,et al.  Study on the absolute configuration of (―)-palau'amine , 2010 .

[11]  J. Gallard,et al.  Unprecedented stylissazoles A-C from Stylissa carteri: another dimension for marine pyrrole-2-aminoimidazole metabolite diversity. , 2010, Angewandte Chemie.

[12]  M. Ilan,et al.  Structure of debromo-carteramine A, a novel bromopyrrole alkaloid from the Mediterranean sponge Axinella verrucosa , 2010 .

[13]  Y. Shang,et al.  Antioxidant effect of erythropoietin on 1-methyl-4-phenylpyridinium-induced neurotoxicity in PC12 cells. , 2007, European journal of pharmacology.

[14]  P. Baran,et al.  Total Synthesis of Dimeric Pyrrole−Imidazole Alkaloids: Sceptrin, Ageliferin, Nagelamide E, Oxysceptrin, Nakamuric Acid, and the Axinellamine Carbon Skeleton , 2007 .

[15]  S. Matsunaga,et al.  Carteramine A, an inhibitor of neutrophil chemotaxis, from the marine sponge Stylissa carteri. , 2007 .

[16]  M. Köck,et al.  Structural assignment of tetrabromostyloguanidine: does the relative configuration of the palau'amines need revision? , 2007, Angewandte Chemie.

[17]  J. Burton.  The MTT assay to evaluate chemosensitivity. , 2005, Methods in molecular medicine.

[18]  R. I. Fryer,et al.  Reinvestigation into the structure of oroidin, a bromopyrrole derivative from marine sponge , 1973 .