title: Biosynthesis of anthracyclinones: isolation of a new early cyclization product aklaviketone.
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.
authors.affiliation: Akademie der Wissenschaften der DDR, Zentralinstitut für Mikrobiologie und experimentelle Therapie, Jena, GDR.
authors.forename: K
authors.initials: K
authors.lastname: Eckardt
authors.forename: G
authors.initials: G
authors.lastname: Schumann
authors.forename: D
authors.initials: D
authors.lastname: Tresselt
authors.forename: W
authors.initials: W
authors.lastname: Ihn
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis*; D009279:Naphthacenes / Q000096:biosynthesis / Q000302:isolation & purification*; D013302:Streptomyces / Q000378:metabolism
chemical_list: D000903:Antibiotics, Antineoplastic; D009279:Naphthacenes; C056802:aklaviketone; C027832:aklavinone