Structure and biosynthesis of toxins from blue-green algae (cyanobacteria)

Microcystis andNodularia species produce cyclic hepta- and pentapeptides, microcystins and nodularin, respectively, both containing the same unusual C₂₀ amino acid, abbreviated Adda. Biosynthesis of nodularin fromNodularia and especially of Adda employs a pathway similar to that employed byMicrocystis for producting microcystins. Nearly 30 new microcystins have been isolated in our laboratory from cyanobacteria species and their structures assigned, largely employing tandem FAB mass spectrometry (FABMS/CID/MS). Acyclic peptides, some of them presumed precursors of nodularin and microcystins, have now been isolated and characterized. The numerous analogs identified or synthesized allow the identification of important parameters in a structure-activity relationship study.