Abstract
Semisynthetic derivatives of daunomycinone with 7,9-isopropylacetal, 7-O-methyl, 7-O-(4-penten-2-yl), and 7-O-(2-hydroxyethyl) substituents were converted byStreptomyces peucetius var.caesius (an adriamycin-blocked mutant) into 7-deoxy-13-dihydrodaunomycinone, while daunomycinone was transformed into 13-dihydrodaunomycinone (predominantly) and 7-deoxy-13-dihydrodaunomycinone.S. coeruleorubidus mutants 24–74 (accumulating aclavinone derivatives instead of daunomycin and related compounds) and 96-85 (producing no anthracycline substances), andS. aureofaciens B-96 (a tetracycline-blocked mutant) transformed the above substrates into the corresponding 13-dihydro derivatives, with the exception of 7,9-isopropylacetal daunomycinone which remained intact. 7-O-Propyn-1-yl daunomycinone was not transformed by any of the strains used under the conditions.
This is a preview of subscription content, log in via an institution to check access.
References
Arcamone F.: Antitumor anthracyclines: Recent developments.Med. Res. Rev.4, 153–188 (1984).
Blumauerová M., Mraček M., Vondráčková J., Podojil M., Hošťálek Z., Vaněk Z.: Regulation of biosynthesis of secondary metabolites. IX. The biosynthetic activity of blocked mutants ofStreptomyces aureofaciens.Folia Microbiol.14, 215–225 (1969).
Blumauerová M., Stajner K., Pokorný V., Hošťálek Z., Vaněk Z.: Mutants ofStreptomyces coeruleorubidus impaired in the biosynthesis of daunomycinone glycosides and related metabolites.Folia Microbiol.23, 255–260 (1978).
Blumauerová M., Královcová E., Matějů, J., Hošťálek Z., Vaněk Z.: Genetic approach to the biosynthesis of anthracyclines, pp. 90–96 inGenetics of Industrial Microorganisms (O.K. Sebek, A.I. Laskin, Eds.). American Society for Microbiology, Washington (DC) 1979a.
Blumauerová M., Královcová E., Matějů J., Jizba J., Vaněk Z.: Biotransformations of anthracyclinones inStreptomyces coeruleorubidus andStreptomyces galilaeus.Folia Microbiol.24, 117–127 (1979b).
Grein A., Merli S., Spalla C.: Biosynthesis of anthracyclines inStreptomyces peucetius, pp. 263–266 inBiological, Biochemical and Biomedical Aspects of Actinomycetes (G. Szabó, S. Biró, M. Goodfellow, Eds.). Akadémiai Kiadó, Budapest 1985.
Jizba J., Sedmera P., Vokoun J., Blumauerová M., Vaněk Z.: Naphthacenequinone derivatives from a mutant strain ofStreptomyces coeruleorubidus.Coll. Czech. Chem. Commun.45, 764–771 (1980).
Jizba J., Sedmera P., Vokoun J., Blumauerová M., Vaněk Z.: Epimer of 7-deoxyaklavinone.Coll. Czech. Chem. Commun.46, 2129–2135 (1981).
Jizba J., Sedmera P., Vokoun J., Lipavská H., Podojil M., Vaněk Z.: Reaction of daunomycinone with diols.Coll. Czech. Chem. Commun.49, 653–665 (1984).
Karnetová J., Matějů J., Sedmera P., Vokoun J., Vaněk Z.: Microbial transformation of daunomycinone byStreptomyces aureofaciens B-96.J. Antib.29, 1199–1202 (1976).
Marek M., Valentová O., Demnerová K., Jizba J., Błumauerová M., Káš J.: Immobilized preparations for the transformation of daunomycinone.Biotechnol. Lett.3, 327–330 (1981).
Marshall V.P., Reisender E.A., Wiley P.F.: Bacterial metabolism of daunomycinone.J. Antib.29, 966–968 (1976).
Matějů J., Podojil M., Vaněk Z.: Reductive transformation of daunomycinone derivatives inStreptomyces coeruleorubidus. 3rd Symp. Socialist Countries on Biotechnology (Abstracts, B6-11), Bratislava (Czechoslovakia) 1983.
Oki T., Komiyama T., Tobe H., Inui T., Takeuchi T., Umezawa H.: Reductive cleavage of anthracycline glycosides by microsomal NADPH-cytochromec reductase.J. Antib.30, 613–615 (1977).
Oki T., Takatsuki Y., Tobe H., Yoshimota A., Takeuchi T., Umezawa H.: Microbial conversion of daunomycin, carminomycin I and feudomycin A to adriamycin.J. Antib.34, 1229–1231 (1981).
Přikrylová V., Sedmera P., Jizba J., Vokoun J., Lipavská H., Podojil M., Vaněk Z.: 7-O-Alkyl derivatives of daunomycinone.Coll. Czech. Chem. Commun.49, 313–319 (1984).
Přikrylová V., Sedmera P., Jizba J., Vokoun J., Lipavská H., Podojil M., Vaněk Z.: 7-O-Alkenyl and alkynyl derivatives of daunomycinone.Coll. Czech. Chem. Commun.50, 2625–2633 (1985).
Wiley P.F., Marshall V.P.: Microbial conversion of anthracycline antibiotics.J. Antib.28, 838–840 (1975).
Wu G.S., Gard A., Rosazza J.P.: Microbial transformations of natural antitumor agents. 13. Conversion of 13-blocked anthracyclinones.J. Antib.33, 705–710 (1980).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Přikrylova, V., Jizba, J., Blumauerova, M. et al. Microbial transformation of semisynthetic derivatives of daunomycinone modified in ring a. Folia Microbiol 34, 459–462 (1989). https://doi.org/10.1007/BF02820754
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02820754