A new antibiotic, phthoramycin (1; C_<40>H_<68>O_<12>) which exhibits antimicrobial activities against fungi such as the plant pathogen Phytophthora parasitica was isolated from the cultured broth of a strain of Streptomyces sp. The structure and biosynthetic origin of 1 were elucidated by the 2-D NMR spectral experiments of pentaacetylphthoramycin (2) in combination with biosynthetic means using [1-^<13>C]- and [1,2-^<13>C_2]acetate and [1-^<13>C]propionate. From the results of ^<13>C-NMR analysis of labeled compounds (2), it was revealed that the antibiotic contained nine intact acetate and six propionate units as shown in Fig. 2. The biosynthesis of okilactomycin (3), produced by a strain of Streptomyces sp., was also investigated by the feeding experiments of [1-^<13>C]- and [2-^<13>C]acetate, [1-^<13>C]propionate, [U-^<13>C_6]glucose, and L-[Me-^<13>C]methionine. The incorporation of seven intact acetate and four propionate units, a glycerol moiety from glucose, and a methyl group of methionine were observed by the ^<13>C-NMR analysis. The biosynthetic pathway may be unique as shown in Fig. 4 in light of the methyl of methionine incorporated into a methyl group of the antibiotic produced by an actinomycete.
