P-44 新属の海洋細菌が生産する新規抗癌抗生物質Pelagiomicin類(ポスター発表の部)

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There are few studies of products from marine microorganisms compared with terrestrial ones. In the course of our screening for new biologically active compounds from marine bacteria, we found new anticancer antibiotics, pelagiomicins A, B and C, produced by a new marine bacterium. Pelagiomicins were unstable in water and alcohols. The producing organism was classified as a new genus and was named Pelagiobacter variabilis. From the cultured broth of the strain, fine red needles (1; 10mg), reddish-orange needles (pelagiomicin A;2; 10mg) and two minor compounds, B (3) and C(4), were obtained by preparative HPLC. The compound 1 was identified to be griseoluteic acid which was previously reported as the chromophore of antibiotic griseolutein A and B produced by a terrestrial actinomycete. The NMR data of 2 indicated the molecule was an ester of 1 and 3-hydroxyvaline(3-HV) or 3-amino-2-hydroxyisovaleric acid. To determine the structure and stereochemistry, D- and L-3-HV were synthesized. The 1H-NMR spectrum of 3-HV was completely superimposed with that of the amino acid isolated from the hydrolysate of 2. The amino acid contained in 2 was identified as L-3-hydroxyvaline by pre-labeled HPLC analysis with a chiral reagent, FLEC, and the structure of 2 was determined including the absolute configuration. The samples obtained of 3 and 4 contained impurities, which were too unstable and too small in quantity to purify further. However, the spectral data of 3 and 4 allowed us to presume that the structures to be valyl- and glycylgriseoluteic acids, respectively. To confirm the structures of 3 and 4, the acids were synthesized from 4-methoxy-3-nitrobenzoic acid. Compounds 3 and 4 were identified as valyl- and glycylgriseoluteic acids, respectively, by HPLC and NMR analyses of mixed samples of natural and synthetic products. Pelagiomicin A is active against gram positive and negative bacteria, and against tumor cells in vitro and in vivo.
天然有機化合物討論会の論文
1995-09-01

P-44 新属の海洋細菌が生産する新規抗癌抗生物質Pelagiomicin類(ポスター発表の部)

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