Bromotryptamine and Bromotyramine Derivatives from the Tropical Southwestern Pacific Sponge <i>Narrabeena nigra</i>

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 <i>Narrabeena nigra</i> collected...

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Bibliographic Details
Main Authors: Maria Miguel-Gordo, Sandra Gegunde, Kevin Calabro, Laurence K. Jennings, Amparo Alfonso, Grégory Genta-Jouve, Jean Vacelet, Luis M. Botana, Olivier P. Thomas
Format: Article
Language:English
Published: MDPI AG 2019-05-01
Series:Marine Drugs
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Online Access:https://www.mdpi.com/1660-3397/17/6/319
Description
Summary: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 <i>Narrabeena nigra</i> collected around the Futuna Islands yielded 18 brominated alkaloids: seven new bromotryptamine derivatives <b>1</b>&#8722;<b>7</b> and one new bromotyramine derivative <b>8</b> together with 10 known metabolites of both families <b>9</b>&#8722;<b>18</b>. Their structures were deduced from extensive analyses of nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS) data. <i>In silico</i> 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 &#181;M on human neuroblastoma SH-SY5Y and microglia BV2 cells, and some of them exhibited an interesting neuroprotective activity by reducing oxidative damage.
ISSN:1660-3397