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