Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge <i>Narrabeena nigra</i>
Maria Miguel-Gordo,
Sandra Gegunde,
Kevin Calabro,
Laurence K. Jennings,
Amparo Alfonso,
Grégory Genta-Jouve,
Jean Vacelet,
Luis M. Botana,
Olivier P. Thomas
Affiliations
Maria Miguel-Gordo
Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
Sandra Gegunde
Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain
Kevin Calabro
Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
Laurence K. Jennings
Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
Amparo Alfonso
Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain
Grégory Genta-Jouve
Laboratoire de Chimie-Toxicologie Analytique et Cellulaire (C-TAC) UMR CNRS 8038 CiTCoM Université Paris-Descartes, 4, avenue de l’Observatoire, 75006 Paris, France
Jean Vacelet
Aix Marseille Université, CNRS, IRD, IMBE UMR 7263, Avignon Université, Institut Méditerranéen de Biodiversité et d’Ecologie marine et continentale, Station Marine d’Endoume, Chemin de la Batterie des Lions, 13007 Marseille, France
Luis M. Botana
Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain
Olivier P. Thomas
Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
So far, the Futuna Islands located in the Central Indo-Pacific Ocean have not been inventoried for their diversity in marine sponges and associated chemical diversity. As part of the Tara Pacific expedition, the first chemical investigation of the sponge Narrabeena nigra collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives 1−7 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 9−18. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. In silico metabolite anticipation using the online tool MetWork revealed the presence of a key and minor biosynthetic intermediates. These 18 compounds showed almost no cytotoxic effect up to 10 µM on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage.
