6 ナルボマイシンおよびピクロマイシンの生合成

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An addition of 0.5% of sodium acetate to a basal medium (Table 1) retarded both the production of the antibiotics (Narbomycin and Picromycin complex) and the growth of Streptomyces venezuelae MCRL 0376 in the first stage (0〜2 days) of the cultivation, but the antibiotics biosynthesis was increased after 3 days up to 200% compared with the control with effecting the growth. These effects were observed only in the medium combined glucose and glycerol. A crystalline compound (mp 125-126°, C_<20>H_<32>O_5) named narbonolide (5) was isolated by the extraction with ethyl acetate from the fermentation beers in a basal medium added with 0.5% of sodium acetate, and determined to be the aglycone of narbomycin (1). The maximum accumulation of narbonolide (5) was observed at 2 days after the cultivation. The antibiotics biosynthesis was also stimulated by the addition of citric, succinic, α-ketoglutaric, fumalic, malic, pyruvic, malonic, and/or acetoacetic acid as was observed by that of acetic acid. Biosynthesis experiments were carried out using deuterium labeled compounds. Deuterioacetic acid (CD_3COOH, 99% D) was incorporated into narbonolide-d_n(n=0〜13, 17.5% of the protons are substituted by deuteriums, Table 2) when added to the fermentation medium of S. venezuelae MCRL 0376. When narbonolide-2d(7,95%) was added to the washed mycelium of S. narbonensis ISP 5016, it was converted to narbomycin-2d(8,25% D), and the latter(40% D) was also converted to picromycin-2d(9,13% D) when added to the washed mycelium of a picromycin-producing strain Streptomyces sp. MCRL 0405.
天然有機化合物討論会の論文
1970-10-01

6 ナルボマイシンおよびピクロマイシンの生合成

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