Novel polyketide metabolites from Streptomyces rimosus mutant strain R1059

J Antibiot (Tokyo). 2005 Dec;58(12):822-7. doi: 10.1038/ja.2005.110.

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)-4beta,8-dihydroxy-3alpha-hydroxymethyl-4alpha-methyl-1,2,3,4-tetrahydronaphthalene1-one (1), 4xi8-dihydroxy-3-hydroxymethyl-4xi-methyl-1,4-dihydronaphthalene-1-one (2) and (rel)-4beta,8-dihydroxy-3alpha-O-[alpha-glucopyranosyl]hydroxymethyl-4alpha-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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / biosynthesis*
  • Chromatography, Gel
  • Culture Media
  • Fermentation
  • Glucosides / biosynthesis*
  • Magnetic Resonance Spectroscopy
  • Naphthols / metabolism*
  • Spectrometry, Mass, Electrospray Ionization
  • Streptomyces / genetics*
  • Streptomyces / metabolism*

Substances

  • 4,8-dihydroxy-3-O-(glucopyranosyl)hydroxymethyl-4-methyl-1,2,3,4-tetrahydronaphthalene-1-one
  • 4,8-dihydroxy-3-hydroxymethyl-4-methyl-1,2,3,4-tetrahydronaphthalene-1-one
  • 4,8-dihydroxy-3-hydroxymethyl-4-methyl-1,4-dihydronaphthalene-1-one
  • Anti-Bacterial Agents
  • Culture Media
  • Glucosides
  • Naphthols