Abstract
The ability to transform biologically exogenous daunomycinone, 13-dihydrodaunomycinone, aklavinone, 7-deoxyaklavinone, ε-rhodomycinone, ε-isorhodomycinone and ε-pyrromycinone was studied in submerged cultures of the following strains: wildStreptomyces coeruleorubidus JA 10092 (W1) and its improved variants 39–146 and 84–17 (type P1) producing glycosides of daunomycinone and of 13-dihydro-daunomycinone, together with ε-rhodomycinone, 13-dihydrodaunomycinone and 7-deoxy-13-dihydro-daunomycinone; in five mutant types ofS. coeruleorubidus (A, B, C, D, E) blocked in the biosynthesis of glycosides and differing in the production of free anthracyclinones; in the wildStreptomyces galilaeus JA 3043 (W2) and its improved variant G-167 (P2) producing glycosides of ε-pyrromycinone and of aklavinone together with 7-deoxy and bisanhydro derivatives of both aglycones; in two mutant typesS. galilaeus (F and G) blocked in biosynthesis of glycosides and differing in the occurrence of anthracyclinones. The following bioconversions were observed: daunomycinone → 13-dihydrodaunomycinone and 7-deoxy-13-di-hydrodaunomycinone (all strains); 13-dihydrodaunomycinone → 7-deoxy-13-dihydrodaunomycinone (all strains); daunomyeinone or 13-dihydrodaunomycinone → glycosides of daunomyeinone and of 13-dihydrodaunomycinone, identical with metabolites W1 and P1 (type A), or only a single glycoside of daunomyeinone (type E); aklavinone → ε-rhodomycinone (types A and B); aklavinone → 7-deoxyaklavinone and bisan-hydroaklavinone (type C); ε-rhodomycinone → ζ-rhodomycinone (types C, E); ε-rhodomycinone → glycosides of ε-rhodomycinone (types W2, P2); ε-isorhodomycinone → glycosides of ε-isorhodomycinone (types W2, P2); ε-pyrromycinone → a glycoside of ε-pyrromycinone (types W1, P1). 7-Deoxyaklavinone remained intact in all tests. Exogenous daunomyeinone suppressed the biosynthesis of its own glycosidea in W1 and P1; it simultaneously increased the production of ε-rhodomyeinone in P1.
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ε-Rhodomycinone, 13-dihydrodaunomycinone and 7-deoxy-13-dihydrodaunomycinone were also found in other strains producing glycosides of daunomycinone (Kernet al. 1977; Komiyamaet al. 1977). Sugar components of glycosides isolated fromS. coeruleorubidus ME 130-A 4 were identified by Takahashiet al. (1977).
The author wish to thank Dr. W. Koch (Central Institute for Microbiology and Experimental Therapy, Jena, GDR) for the sample of ε-isorhodomycinone and Dr. P. Sedmera and Dr. J. Vokoun (Institute of Microbiology, Czechoslovak Academy of Sciences, Prague) for the measurement of NMR and mass spectra confirming the identity of the isolated anthracyclinones with the standards.
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Blumauerová, M., Královcová, E., Matějů, J. et al. Biotransformations of anthracyclinones inStreptomyces coeruleorubidus andStreptomyces galilaeus . Folia Microbiol 24, 117–127 (1979). https://doi.org/10.1007/BF02927295
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DOI: https://doi.org/10.1007/BF02927295