112(P67) 藍藻Microcystis aeruginosaより得られた生物活性物質(ポスター発表の部)

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In the continuous studies of protease inhibitors of microalgae, we have found that the cyanobacterium Microcystis aeruginosa is a new and rich source of unique biologically active compounds. Here we report the isolation and structure elucidation of novel biologically active peptides of M. aeruginosa. The 80% methanol extract of lyophilized alga (M. aeruginosa NIES-299) was subjected to solvent partition, ODS column chromatography followed by ODS HPLC to obtain microginin-type peptides 1-4. Their structures were determined by FABMS and 2D NMR spectra. The absolute stereochemistries of usual and N-Me amino acids were determined to be all L-form by the HPLC analysis of the Marfey derivatives. The absolute stereochemistry of their β-amino acids was deduced by a combination of spectral and chemical studies. Microginin-type peptides 8-10 were also isolated from the cyanobacterium M. aeruginosa (NIES-90, 478). 1-4 and 10 inhibited leucine aminopeptidase, and 10 also inhibited angiotensin-converting enzyme. The 80% methanol extract of lyophilized alga (M. aeruginosa NIES-88, 90, 478) was subjected to solvent partition, ODS column chromatography followed by ODS HPLC to obtain micropeptin-type peptides 13-21. Their structures were determined by FABMS and 2D NMR spectra. The absolute stereochemistries of usual and N-Me amino acids were determined to be all L-form by the HPLC analysis of the Marfey derivatives or the chiral GC analysis of N-trifluoroacetyl isopopyl ester derivatives. The absolute stereochemistries of the glyceric acid 3-O-sulfate (disulfate) in 13-15 were determined to be all D-form by chrial GC analysis of O-heptafluorobutyryl isopropyl ester derivatives. The absolute stereochemistries of Ahp were deduced as follows. PCC oxidation of 13-15 followed by hydrolysis with HCl afforded Glu, which was proved to be L-form from the HPLC analysis of the Marfey derivatives. The reduction of 16-21 with NaBH_4 followed by hydrolysis with HCl afforded pentahomoserine and Pro, which were proved to be L-form from the HPLC analysis of the Marfey derivatives. The relative stereochemistries of Ahp of 13 and 16 were decided as Fig. 1 and 2 by NOESY correlations. Therefore, the stereochemistries of Ahp were decided to be (3S, 6R)-3-amino-6-hydroxy-2-piperidone. 13-15 inhibited plasmin, and 16, 18-21 inhibited chymotrypsin. The 80% methanol extract of lyophilized alga (M. aeruginosa NIES-88) was subjected to solvent partition, ODS column chromatography followed by ODS HPLC to obtain kawaguchipeptin A (22) and B (23). Their structures were determined by FABMS and 2D NMR spectra. The absolute stereochemistries of usual amino acids were determined to be all L-form besides Leu in 22 by the HPLC analysis of the Marfey derivatives or the chiral GC analysis of N-trifluoroacetyl isopopyl ester derivatives. 22 and 23 inhibited the growth of the gram positive bacterium Staphylococcus aureus.
天然有機化合物討論会の論文
1997-07-20

112(P67) 藍藻Microcystis aeruginosaより得られた生物活性物質(ポスター発表の部)

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