Abstract
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)-4β,8-dihydroxy-3α-hydroxymethyl-4α-methyl-1,2,3,4-tetrahydronaphthalene-1-one (1), 4ξ,8-dihydroxy-3-hydroxymethyl-4ξ-methyl-1,4-dihydronaphthalene-1-one (2) and (rel)-4β,8-dihydroxy-3α-O-[α-glucopyranosyl]hydroxymethyl-4α-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.
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Deseo, M., Hunter, I. & Waterman, P. Novel Polyketide Metabolites from Streptomyces rimosus Mutant Strain R1059. J Antibiot 58, 822–827 (2005). https://doi.org/10.1038/ja.2005.110
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DOI: https://doi.org/10.1038/ja.2005.110