On the chemistry, toxicology and genetics of the cyanobacterial toxins, microcystin, nodularin, saxitoxin and cylindrospermopsin

Mar Drugs. 2010 May 10;8(5):1650-80. doi: 10.3390/md8051650.

Abstract

The cyanobacteria or "blue-green algae", as they are commonly termed, comprise a diverse group of oxygenic photosynthetic bacteria that inhabit a wide range of aquatic and terrestrial environments, and display incredible morphological diversity. Many aquatic, bloom-forming species of cyanobacteria are capable of producing biologically active secondary metabolites, which are highly toxic to humans and other animals. From a toxicological viewpoint, the cyanotoxins span four major classes: the neurotoxins, hepatotoxins, cytotoxins, and dermatoxins (irritant toxins). However, structurally they are quite diverse. Over the past decade, the biosynthesis pathways of the four major cyanotoxins: microcystin, nodularin, saxitoxin and cylindrospermopsin, have been genetically and biochemically elucidated. This review provides an overview of these biosynthesis pathways and additionally summarizes the chemistry and toxicology of these remarkable secondary metabolites.

Keywords: alkaloid; cyanotoxin; non-ribosomal peptide; polyketide; toxicology.

Publication types

  • Review

MeSH terms

  • Alkaloids
  • Animals
  • Bacterial Toxins / biosynthesis
  • Bacterial Toxins / chemistry
  • Bacterial Toxins / genetics*
  • Bacterial Toxins / isolation & purification
  • Bacterial Toxins / toxicity*
  • Cyanobacteria / genetics
  • Cyanobacteria / metabolism*
  • Cyanobacteria Toxins
  • Genes, Bacterial
  • Marine Toxins / biosynthesis
  • Marine Toxins / chemistry
  • Marine Toxins / genetics*
  • Marine Toxins / isolation & purification
  • Marine Toxins / toxicity*
  • Microcystins / biosynthesis
  • Microcystins / chemistry
  • Microcystins / genetics*
  • Microcystins / isolation & purification
  • Microcystins / toxicity*
  • Peptides, Cyclic / biosynthesis
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / genetics
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / toxicity
  • Saxitoxin / biosynthesis
  • Saxitoxin / chemistry
  • Saxitoxin / genetics
  • Saxitoxin / isolation & purification
  • Saxitoxin / toxicity
  • Uracil / analogs & derivatives
  • Uracil / biosynthesis
  • Uracil / chemistry
  • Uracil / isolation & purification
  • Uracil / toxicity

Substances

  • Alkaloids
  • Bacterial Toxins
  • Cyanobacteria Toxins
  • Marine Toxins
  • Microcystins
  • Peptides, Cyclic
  • nodularin
  • cylindrospermopsin
  • Saxitoxin
  • Uracil
  • microcystin