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Published on: March 20, 2012
Polymethoxy-1-alkenes from Aphanizomenon ovalisporum inhibit vertebrate development in the zebrafish (Danio rerio)
Asha Jaja-Chimedza1, Miroslav Gantar2, Patrick D L Gibbs3
1Marine Science Program, Department of Chemistry and Biochemistry, 354 Marine Science Building, Florida International University, 3000 NE 151st Street, North Miami, FL 33181, USA.
Abstract:
Cyanobacteria are recognized producers of a wide array of toxic or otherwise bioactive secondary metabolites. The present study utilized the zebrafish (Danio rerio) embryo as an aquatic animal model of vertebrate development to identify, purify and characterize lipophilic inhibitors of development (i.e., developmental toxins) from an isolate of the freshwater cyanobacterial species, Aphanizomenon ovalisporum.Bioassay-guided fractionation led to the purification, and subsequent chemical characterization, of an apparent homologous series of isotactic polymethoxy-1-alkenes (1-6), including three congeners (4-6) previously identified from the strain, and two variants previously identified from other species (2 and 3), as well as one apparently novel member of the series (1). Five of the PMAs in the series (1-5) were purified in sufficient quantity for comparative toxicological characterization, and toxicity in the zebrafish embryo model was found to generally correlate with relative chain length and/or methoxylation. Moreover, exposure of embryos to a combination of variants indicates an apparent synergistic interaction between the congeners. Although PMAs have been identified previously in cyanobacteria, this is the first report of their apparent toxicity. These results, along with the previously reported presence of the PMAs from several cyanobacterial species, suggest a possibly widespread distribution of the PMAs as toxic secondary metabolites and warrants further chemical and toxicological investigation.
Insights
Researchers identified polymethoxy-1-alkenes (PMAs) from Aphanizomenon ovalisporum, demonstrating their toxicity to zebrafish embryos. This study highlights PMAs as potentially widespread developmental toxins in cyanobacteria.
Area of Science:
- Environmental toxicology
- Natural product chemistry
- Marine biology
Background:
- Cyanobacteria produce diverse bioactive secondary metabolites, including potential toxins.
- The zebrafish embryo model is valuable for assessing vertebrate developmental toxicity.
Purpose of the Study:
- To identify and characterize lipophilic developmental toxins from Aphanizomenon ovalisporum.
- To evaluate the toxicity of isolated compounds using the zebrafish embryo model.
Main Methods:
- Bioassay-guided fractionation was used to isolate compounds.
- Chemical characterization identified a series of polymethoxy-1-alkenes (PMAs).
- Zebrafish embryo assays assessed the developmental toxicity of purified PMAs.
Main Results:
- A homologous series of isotactic polymethoxy-1-alkenes (PMAs) was purified and characterized.
- Five PMAs (1-5) exhibited toxicity in zebrafish embryos, correlating with chain length and methoxylation.
- Synergistic toxicity was observed when embryos were exposed to a combination of PMA variants.
Conclusions:
- This study reports the apparent toxicity of PMAs for the first time.
- PMAs are suggested to be widespread toxic secondary metabolites in cyanobacteria.
- Further chemical and toxicological investigations of PMAs are warranted.
