Identification of 12 Hepatotoxins from a Homer Lake Bloom of the Cyanobacteria Microcystis aeruginosa, Microcystis viridis, and Microcystis wesenbergii: Nine New Microcystins

Michio Namikoshi, Kenneth L. Rinehart, Ryuichi Sakai, Richard R. Stotts, Andrew M. Dahlem, Val Richard Beasley, Wayne W. Carmichael, William R. Evans

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Abstract

Eleven minor components were isolated, together with microcystin-LR (LR, 1, Scheme I) as the principal toxin (ca. 90% of the toxic components), from Microcystis cyanobacteria (blue-green algae) collected from Homer Lake (Illinois) in the summer of 1988. The components were characterized by amino acid analysis and HRFABMS, FABMS/MS, 1H NMR, and UV spectroscopic methods as microcystins-RR (2) and -YR (3) (Scheme I) and nine new microcystins. The structures of seven new microcystins were assigned as [DMAdda5]microcystin-LR (4), [Dha7]microcystin-LR (5), microcystin-FR (6), microcystin-AR (7), microcystin-M(O)R (8), [Mser7]microcystin-LR (9), and microcystin-WR (12). Compound 4 is the first microcystin containing 9-O-demethyl-Adda, while phenylalanine, N-methylserine, and tryptophan are also new variations in amino add components of microcystins. Compound 11 was deduced to be a (C3H7O) monoester of the α-carboxyl on the Glu unit of LR (1). New microcystin 11 caused no apparent toxic effects in mice dosed ip at 1 mg/kg, while the others had LD50's of 90–800 µg/kg.

Original languageEnglish (US)
Pages (from-to)866-872
Number of pages7
JournalJournal of Organic Chemistry
Volume57
Issue number3
DOIs
Publication statusPublished - Jan 1 1992

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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