Novel polyketide metabolites from Streptomyces rimosus mutant strain R1059

Three novel polyketide metabolites were isolated from laboratory-scale fermentation of the Streptomyces rimosus mutant strain R1059. Structural elucidation of the compounds was based on NMR experiments. The compounds were characterized as naphthalene derivatives: (rel)-4 beta,8-dihydroxy-3 alpha-hydroxymethyl-4 alpha-methyl-1,2,3,4-tetrahydronaphthalene-1-one (1), 4 xi,8-dihydroxy-3-hydroxymethyl-4 xi-methyl-1,4-dihydronaphthalene-1-one (2) and (rel)-4 beta,8-dihydroxy-3 alpha-O-[alpha-glucopyranosyl]hydroxymethyl-4 alpha-methyl-1,2,3,4-tetrahydronaphthalene-1-one (3). The compounds isolated appear to be derived via a shorter polyketide backbone than oxytetracycline (4), the normal end-product made by the parent of this strain. Compound 3 was the glucoside of 1 and must be formed as a post-PKS reaction by the activation of a glycosyl transferase, which has not been reported in this species before.