title: Anabaenolysins, novel cytolytic lipopeptides from benthic Anabaena cyanobacteria.
abstract: Two novel cyclic lipopeptides, anabaenolysin A and anabaenolysin B, were isolated from two benthic cyanobacterial strains of the genus Anabaena. This novel class of cyanobacterial lipopeptides has a general structure of a small peptide ring consisting of four amino acids from which two are proteinogenic and two unusual; glycine(1), glycine(2), 2-(3-amino-5-oxytetrahydrofuran-2-yl)-2-hydroxyacetic acid(3) and a long unsaturated C(18) β-amino acid(4) with a conjugated triene structure. They are distinguished by the presence of a conjugated dienic structure in the C18 β-amino acid present in anabaenolysin A but not in anabaenolysin B. Conjugated triene structure generates a typical UV spectrum for anabaenolysins for easy recognition. Anabaenolysin A constituted up to 400 ppm of the cyanobacterial dry weight. We found evidence of thirteen variants of anabaenolysins in one cyanobacterial strain. This suggests that the anabaenolysins are an important class of secondary metabolites in benthic Anabaena cyanobacteria. Both anabaenolysin A and B had cytolytic activity on a number of mammalian cell lines.
authors: Division of Microbiology, Department of Food and Environmental Sciences, University of Helsinki, Helsinki, Finland.
authors: Jouni
authors: J
authors: Jokela
authors: Linn
authors: L
authors: Oftedal
authors: Lars
authors: L
authors: Herfindal
authors: Perttu
authors: P
authors: Permi
authors: Matti
authors: M
authors: Wahlsten
authors: Stein Ove
authors: SO
authors: Døskeland
authors: Kaarina
authors: K
authors: Sivonen
mesh_terms: D017033:Anabaena / Q000737:chemistry*; D000818:Animals; D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D002478:Cells, Cultured; D006367:HeLa Cells; D022781:Hepatocytes / Q000187:drug effects; D006801:Humans; D055666:Lipopeptides / Q000737:chemistry* / Q000494:pharmacology*; D008297:Male; D008856:Microscopy, Fluorescence; D051381:Rats; D017208:Rats, Wistar
chemical_list: D055666:Lipopeptides