47(P03) STUDIES ON PRODUCTION OF PEPTIDE COMPOUNDS BY CYANOBACTERIA (IV) : NODULARIA SPUMIGENA

Fujii Kiyonaga, Harada Ken-ichi, Suzuki Makoto, Adachi Kyoko, Sano Hiroshi, Noguchi Kazuyoshi, Hirayama Kazuo, Sivonen Kaarina

doi:10.24496/tennenyuki.38.0_277

Cyanobacteria produce toxic peptides such as microcystins and nodularins, which are known as the lethal hepatotoxins. Many research groups have isolated other types of peptides than these hepatotoxins from cyanobacteria. We have also continued to focus on these peptide compounds produced by toxic and non-toxic cyanobactera and the biosynthetic relationship between such peptides and toxic peptide compounds. In the present study we would like to report that two types of cyclic and linear peptides, nodulapeptins A (1), B (2) and spumigins A〜C (3〜6), were isolated together with nodularins from a toxic cayanobacterium, Nodularia spumigena AVl and a novel peptide compound, spumigin HKVV (7), was isolated from a non-toxic cyanobacterium, N. spumigena HKVV. Their structures were determinated by 2D-NMR techniques, MS/MS experiments and the advanced Marfey's method. The structures of nodulapeptins are similar to those of anabaenoeptins which were isolated from the toxic cyanobacteria, Anabaena sp. that co-produces microcystins. Recently, Murakami et al. reported the isolation and the structural determination of aeruginosins from Microcystis aeruginosa and the proposed structures for spumigins A〜C have a resemblance to those for these compounds. On the other hand, spumigin HKVV has a quite novel structure comprised of 2-azabicyclo[3.3.1]non-3-carboxylic acid, Ile, O-methlated glyceric acid sulfate, glucose and a cyclic guanidine moiety and its partial structure seems to be similar to those of spumigins A〜C. The production of nodulapeptins and anabaenopeptins are suggested to be characteristic for the toxic cyanobacteria, because they were not isolated from the non-toxic cyanobacterium.

47(P03) STUDIES ON PRODUCTION OF PEPTIDE COMPOUNDS BY CYANOBACTERIA (IV) : NODULARIA SPUMIGENA

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