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.

Antifungal activity improved by coproduction of cyclodextrins and anabaenolysins in Cyanobacteria

“…chromatography (HPLC) to screen the methanol extracts from the strains, and detection was based on the characteristic UV spectrum of the anabaenolysins resulting from three conjugated double bonds in the hydroxyamino fatty acid (16). We then tested strains containing the characteristic UV spectra against bacteria (data not shown) and fungi to verify the activity of the cell extracts.…”

“…Anabaenolysins are lipopeptides produced by species of Anabaena isolated from the Baltic Sea (16). Our previous study found them to consist of two glycines, a 2-(3-amino-5-oxytetrahydrofuran-2-yl)-2-hydroxyacetic acid and a long (C16-C19) unsaturated α-hydroxy-β-amino carboxylic acid (16).…”

“…Our previous study found them to consist of two glycines, a 2-(3-amino-5-oxytetrahydrofuran-2-yl)-2-hydroxyacetic acid and a long (C16-C19) unsaturated α-hydroxy-β-amino carboxylic acid (16). Anabaena sp.…”

“…XPORK15F produces 10 variants of anabaenolysins, which differ in the length of the methylene units and the degree of unsaturation of the hydroxyamino fatty acid. Anabaenolysins may account for up to 0.1% of the dry weight of Anabaena strains (16). Anabaenolysins are able to permeabilize mammalian cells in a cholesterol-dependent manner and show more hemolytic potency than do the plant saponin digitonin and the bacterial cyclic peptide surfactin (17).…”

Accumulation and effects of cyanobacterial microcystins and anatoxin-a on benthic larvae of Chironomus spp. (Diptera: Chironomidae)

“…and benthic Anabaena species, in addition to ANTX may also produce other neurotoxins, like anatoxin-a(S) and cytotoxic oligopeptides (e.g. anabaenolysins; Jokela et al, 2012). Planktothrix spp., in addition to MCs may also produce other bioactive oligopeptides (e.g.…”