Biosynthesis of anthracyclinones: isolation of a new early cyclization product aklaviketone

J Antibiot (Tokyo). 1988 Jun;41(6):788-93. doi: 10.7164/antibiotics.41.788.

Abstract

Five metabolites were isolated from fermentations of a mutant strain S 383 of Streptomyces galilaeus. Components S 383-O and S 383-A were identified as known derivatives of anthraquinone and naphthacenequinone, respectively, previously isolated from cultures of other blocked mutants of S. galilaeus strains. Component S 383-X was identical with 7-deoxyaklavinone. Compound S 383-Y (aklaviketone) was found to be a new metabolite. Its chemical structure has been determined by physico-chemical methods including mass spectrometry and NMR spectral studies. The compound (7-dehydro-7-deoxy-7-oxoaklavinone) is most likely the first cyclization product along the metabolic chain possessing the tetracyclic carbon skeleton of anthracyclinones. A proposed pathway is discussed.

MeSH terms

  • Antibiotics, Antineoplastic / biosynthesis*
  • Naphthacenes / biosynthesis
  • Naphthacenes / isolation & purification*
  • Streptomyces / metabolism

Substances

  • Antibiotics, Antineoplastic
  • Naphthacenes
  • aklaviketone
  • aklavinone