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Toxins 2014, 6(12), 3568-3581; doi:10.3390/toxins6123568

Indole Alkaloids from Fischerella Inhibit Vertebrate Development in the Zebrafish (Danio rerio) Embryo Model

1
Department of Chemistry and Biochemistry, Florida International University, 3000 NE 151st Street, North Miami, FL 33181, USA
2
Department of Biological Sciences, Florida International University, 11200 SW 8th Street, Miami, FL 33199, USA
3
Division of Marine Biology and Fisheries, Rosenstiel School of Marine and Atmospheric Sciences, University of Miami, 4600 Rickenbacker Causeway, Miami, FL 33146, USA
*
Author to whom correspondence should be addressed.
Received: 18 September 2014 / Revised: 25 November 2014 / Accepted: 16 December 2014 / Published: 22 December 2014
(This article belongs to the Section Marine and Freshwater Toxins)
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Abstract

Cyanobacteria are recognized producers of toxic or otherwise bioactive metabolite associated, in particular, with so-called “harmful algal blooms” (HABs) and eutrophication of freshwater systems. In the present study, two apparently teratogenic indole alkaloids from a freshwater strain of the widespread cyanobacterial genus, Fischerella (Stigonemataceae), were isolated by bioassay-guided fractionation, specifically using the zebrafish (Danio rerio) embryo, as a model of vertebrate development. The two alkaloids include the previously known 12-epi-hapalindole H isonitrile (1), and a new nitrile-containing variant, 12-epi-ambiguine B nitrile (2). Although both compounds were toxic to developing embryos, the former compound was shown to be relatively more potent, and to correlate best with the observed embryo toxicity. Related indole alkaloids from Fischerella, and other genera in the Stigonemataceae, have been widely reported as antimicrobial compounds, specifically in association with apparent allelopathy. However, this is the first report of their vertebrate toxicity, and the observed teratogenicity of these alkaloids supports a possible contribution to the toxicity of this widespread cyanobacterial family, particularly in relation to freshwater HABs and eutrophication. View Full-Text
Keywords: Fischerella; Stigonemataceae; cyanobacteria; hapalindoles; ambiguines; indole alkaloids; zebrafish embryo; teratogenicity; vertebrate toxicity; harmful algal blooms Fischerella; Stigonemataceae; cyanobacteria; hapalindoles; ambiguines; indole alkaloids; zebrafish embryo; teratogenicity; vertebrate toxicity; harmful algal blooms
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Walton, K.; Gantar, M.; Gibbs, P.D.L.; Schmale, M.C.; Berry, J.P. Indole Alkaloids from Fischerella Inhibit Vertebrate Development in the Zebrafish (Danio rerio) Embryo Model. Toxins 2014, 6, 3568-3581.

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