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Open AccessFeature PaperArticle

Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra

1
Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
2
Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain
3
Laboratoire de Chimie-Toxicologie Analytique et Cellulaire (C-TAC) UMR CNRS 8038 CiTCoM Université Paris-Descartes, 4, avenue de l’Observatoire, 75006 Paris, France
4
Muséum National d’Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes (UMR 7245), Sorbonne Universités, CNRS, 75005 Paris, France
5
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
*
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(6), 319; https://doi.org/10.3390/md17060319
Received: 28 April 2019 / Revised: 27 May 2019 / Accepted: 28 May 2019 / Published: 30 May 2019
(This article belongs to the Special Issue Advances in Marine Alkaloids)
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 17 and one new bromotyramine derivative 8 together with 10 known metabolites of both families 918. 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. View Full-Text
Keywords: Futuna; Porifera; Narrabeena; coral reefs; aromatic alkaloids; Bromotryptamine; Bromotyramine; neuroprotective agents Futuna; Porifera; Narrabeena; coral reefs; aromatic alkaloids; Bromotryptamine; Bromotyramine; neuroprotective agents
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Miguel-Gordo, M.; Gegunde, S.; Calabro, K.; Jennings, L.K.; Alfonso, A.; Genta-Jouve, G.; Vacelet, J.; Botana, L.M.; Thomas, O.P. Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge Narrabeena nigra. Mar. Drugs 2019, 17, 319.

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