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. 2019 May 30;17(6):319.
doi: 10.3390/md17060319.

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

Maria Miguel-Gordo  1 , Sandra Gegunde  2 , Kevin Calabro  3 , Laurence K Jennings  4 , Amparo Alfonso  5 , Grégory Genta-Jouve  6   7 , Jean Vacelet  8 , Luis M Botana  9 , Olivier P Thomas  10
Affiliations

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

Maria Miguel-Gordo et al. Mar Drugs. .

Abstract

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.

Keywords: Bromotryptamine; Bromotyramine; Futuna; Narrabeena; Porifera; aromatic alkaloids; coral reefs; neuroprotective agents.

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Conflict of interest statement

The authors declare no conflict of interest. The funders had no role in the design of the study; in the collection, analyses, or interpretation of data; in the writing of the manuscript, or in the decision to publish the results.

Figures

Figure 1
Figure 1
Chemical structures of seven new bromotryptamine and one new bromotyramine derivatives isolated from the sponge Narrabeena nigra.
Figure 2
Figure 2
Comparison between the calculated and experimental electronic circular dichroism (ECD) spectra of both enantiomers of 4.
Figure 3
Figure 3
Key correlation spectroscopy COSY (bold) and heteronuclear multiple bond correlation HMBC (arrows from H to C) for narrabeenamine B (5).
Figure 4
Figure 4
Comparison of the calculated and experimental ECD spectra of the two epimers of 5 at C-2.
Figure 5
Figure 5
Effect of brominated alkaloids on oxidative damage in neuroblastoma SH-SY5Y cell line. Cells were treated with compounds (0.001, 0.01, 0.1, 1, and 10 µM) in the presence of tert-butylhydroperoxide (TBHP) at 65 μM for 6 h. Cell viability was determined using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Data are represented in percentage of cell control, being the result of mean absorbance ± SEM of three independent experiments performed in triplicate. TBHP-treated cells were compared with cells treated with compounds plus TBHP by ANOVA followed by post hoc Dunnett’s test. *p < 0.05 or TBHP-treated cells versus untreated cells ###p < 0.001.
Figure 6
Figure 6
Effects of brominated alkaloids on nitric oxide (NO) release in BV2 microglia cell line. Cells were treated with 5, 7, 9, 10, 11, 12, 13, 15, and 18 at 0.1 and 1 μM for 1 h before the stimulation with lipopolysaccharide (LPS) at 500 ng/mL for 24 hours. NO release was determined using Griess reagent. Data are represented in percentage of cells treated with LPS, being the result of mean fluorescence intensity ± SEM of three independent experiments done in duplicate. LPS-treated cells were compared with cells treated with compounds plus LPS by ANOVA followed by post hoc Dunnett’s test. *p < 0.05 or LPS-treated cells versus untreated cells ###p < 0.001.
Scheme 1
Scheme 1
Biosynthetic hypothesis for the formation of the bromotryptophan alkaloids isolated from the sponge N. nigra.
Figure 7
Figure 7
In silico metabolization network of the bromotryptamine derivatives present in the fraction of the sponge N. nigra. In green are the isolated compounds and in orange, the anticipated structures of minor analogues proposed by the webserver MetWork v0.3.5, Paris [49].
See this image and copyright information in PMC

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