Alizarin glucosyl transferase activity was found in five mutant strains of Streptomyces aureofaciens. The activity bears no direct relationship to the final products of tetracycline biosynthesis.

• MeSH
• Anthraquinones pharmacology   MeSH
• Glucosides metabolism   MeSH
• Glucosyltransferases isolation & purification   metabolism   MeSH
• Mutagenesis MeSH
• Streptomyces aureofaciens enzymology   genetics   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• alizarin MeSH Browser
• Anthraquinones MeSH
• Glucosides MeSH
• Glucosyltransferases MeSH

An asporogenous spontaneous mutant of Streptomyces aureofaciens named ASR1 was selected on streptomycin gradient plates. The mutant is very stable and differs in ultrastructure and morphology, it is prototrophic but it lost the ability to grow well on soybean extract medium and produces one-tenth tetracyclines of the parent. The ASR1 mutant has a 3-4-fold increased resistance to streptomycin and is cross-resistant to other aminoglycosides. Comparison of the protein profiles from both strains on SDS gels revealed a very low expression of a 29.5 kDa protein in the ASR1 mutant which is overexpressed in both vegetative cells and spores of the parental strain.

• MeSH
• Aminoglycosides MeSH
• Anti-Bacterial Agents pharmacology   MeSH
• Drug Resistance, Microbial genetics   MeSH
• Bacterial Proteins genetics   isolation & purification   MeSH
• Mutation MeSH
• Spores, Bacterial genetics   MeSH
• Streptomyces aureofaciens drug effects   genetics   ultrastructure   MeSH
• Tetracycline biosynthesis   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Aminoglycosides MeSH
• Anti-Bacterial Agents MeSH
• Bacterial Proteins MeSH
• Tetracycline MeSH

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 by Streptomyces 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), and S. 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.

• MeSH
• Naphthacenes metabolism   MeSH
• Streptomycetaceae metabolism   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• daunomycinone MeSH Browser
• Naphthacenes MeSH

Streptomyces aureofaciens glucosidizes 1,2,4-trihydroxy-9,10-anthraquinone (purpurin) added to the cultivation medium to yield the corresponding 2-beta-D-glucoside. The identity of the glucoside was demonstrated by comparing its physico-chemical properties with data of an authentic sample prepared synthetically. A further chemical glucosidation of the acetylated 2-beta-D-glucoside gives rise to 2-(hepta-O-acetyl-beta-gentiobiosyl)-4-(tetra-O-acetyl-beta-D-gluc opyranosyl) purpurin. All the derivatives are immunoactive.

• MeSH
• Anthraquinones * MeSH
• Chemical Phenomena MeSH
• Chemistry MeSH
• Fermentation MeSH
• Glucosides biosynthesis   MeSH
• Mass Spectrometry MeSH
• Lectins immunology   metabolism   MeSH
• Magnetic Resonance Spectroscopy MeSH
• Spectrophotometry, Infrared MeSH
• Streptomyces aureofaciens metabolism   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthraquinones * MeSH
• Glucosides MeSH
• Lectins MeSH
• purpurin anthraquinone MeSH Browser

A new metabolite denoted as verotetrone was isolated from the mycelium of the mutant strain Streptomyces aureofaciens NMG-2. Interpretations of physical data concerning verotetrone and its triacetate and, the determination of its degradation product indicate that verotetrone belongs to pretetramide-type metabolites. Verotetrone exhibits neither antibacterial nor antifungal activity. In vitro it inhibits the synthesis of nucleic acids as well as proteins in Ehrlich ascites carcinoma cells. Both verotetrone and its triacetate interfere in vivo with the metabolism of tumour and lymphoid cells, exhibiting antitumour or immunosuppressive activity. This activity, which is more intense with verotetrone than with its triacetate, is detectable in a dose which is already toxic in some animals.

• MeSH
• Anthracyclines * MeSH
• Bacteria drug effects   MeSH
• Candida drug effects   MeSH
• Carcinoma, Ehrlich Tumor metabolism   MeSH
• Leukemia, Experimental drug therapy   immunology   MeSH
• Neoplasms, Experimental MeSH
• Mice, Inbred Strains MeSH
• Mutation MeSH
• Mice MeSH
• Naphthacenes analysis   isolation & purification   pharmacology   MeSH
• Nucleic Acids biosynthesis   MeSH
• Antibiotics, Antineoplastic * MeSH
• Streptomyces aureofaciens metabolism   MeSH
• Transplantation Immunology MeSH
• Animals MeSH
• Check Tag
• Mice MeSH
• Female MeSH
• Animals MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthracyclines * MeSH
• Naphthacenes MeSH
• Nucleic Acids MeSH
• Antibiotics, Antineoplastic * MeSH
• verotetrone MeSH Browser

Differential centrifugation, precipitation with ammonium sulphate and chromatography on DEAE-cellulose led to a twenty-fold purification of glucosyltransferase from Streptomyces aureofaciens B 96. The Michaelis constants for glucosyluridyl diphosphate (UDP-glucose) was 10.8 microM for 1,2-dihydroxy-9,10-anthraquinone (alizarin) 110 microM; the maximum rate of glucosylation reaction was 5.32 mumol per s per mg protein. The pH optimum was at 7.1; the flat temperature optimum was at 30 degrees C. Using some hydroxy derivatives of 9,10-anthraquinone it was found that the production of glucosides from aglycones with alpha-hydroxyl groups was about 1/8 of the values obtained with beta-hydroxyl substrates. In both types of aglycones the presence of another hydroxyl group led to a higher glucoside production.

• MeSH
• Anthraquinones MeSH
• Glucosides MeSH
• Glucosyltransferases isolation & purification   metabolism   MeSH
• Hydrogen-Ion Concentration MeSH
• Streptomyces aureofaciens enzymology   MeSH
• Temperature MeSH
• Uridine Diphosphate Glucose MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthraquinones MeSH
• Glucosides MeSH
• Glucosyltransferases MeSH
• Uridine Diphosphate Glucose MeSH

Mutants of Streptomyces coeruleorubidus, blocked in the biosynthesis of anthracycline antibiotics of the daunomycine complex, were isolated from the production strains after treatment with UV light, gamma-radiation, nitrous acid, and after natural selection; according to their different biosynthetic activity the mutants were divided into five phenotypic groups. Mutants of two of these groups produced compounds that had not yet been described in Streptomyces coeruleorubidus (aklavinone, 7-deoxyaklavinone, zeta-rhodomycinone and glycosides of epsilon-rhodomycinone). The mutants differed from the parent strains and also mutually in morphological characteristics but no direct correlation between these changes and the biosynthetic activity could be observed in most cases.

• MeSH
• Anthraquinones biosynthesis   MeSH
• Daunorubicin biosynthesis   MeSH
• Glycosides biosynthesis   MeSH
• Mutation MeSH
• Streptomyces cytology   genetics   metabolism   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthraquinones MeSH
• Daunorubicin MeSH
• Glycosides MeSH

Streptomyces aureofaciens B 96 grown on a synthetic medium glucosylated exogenous 1,2-dihydroxy-9,10-anthraquinone (alizarin). The glucosylation was inhibited by 2,4-dinitrophenol added to the cultivation medium. A cell-free preparation was obtained from the mycelium isolated after 16 h of growth and was found to catalyze the transfer of glucose from glucosyluridyl diphosphate to 1,2-dihydroxy-9,10-anthraquinone, giving rise to 1-hydroxy-2-(beta-D-glucopyranosyloxy)-9,10-anthraquinone.

• MeSH
• Anthraquinones metabolism   MeSH
• Bacterial Proteins biosynthesis   MeSH
• Cell-Free System MeSH
• Dinitrophenols pharmacology   MeSH
• Glucosides biosynthesis   MeSH
• Glucosyltransferases isolation & purification   metabolism   MeSH
• Sucrose metabolism   MeSH
• Streptomyces aureofaciens enzymology   MeSH
• Streptomycin pharmacology   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthraquinones MeSH
• Bacterial Proteins MeSH
• Dinitrophenols MeSH
• Glucosides MeSH
• Glucosyltransferases MeSH
• Sucrose MeSH
• Streptomycin MeSH

Mutants of Streptomyces atroolivaceus blocked in the biosynthesis of mithramycin were isolated both by natural selection and after treatment with mutagenic factors (UV and gamma rays, nitrous acid). Both physical factors were more effective than nitrous acid. The selection was complicated by a high instability of isolates, out of which 20-80% (depending on their origin) reversed spontaneously to the parent type. The primary screening (selection of morphological variants and determination of their activity using the method of agar blocks) made it possible to detect only potentially non-productive strains; however, the final selection had to be performed always under submerged conditions. Fifty-four stable non-productive mutants were divided, according to results of the chromatographic analysis, in five groups differing in production of six biologically inactive metabolites (compounds A-H). The mutants did not accumulate chromomycinone, chromocyclomycin and chromocyclin. On mixed cultivation none of the pairs of mutants was capable of cosynthesis of mithramycin or new compounds differing from standard metabolites. Possible causes of the above results are discussed.

• MeSH
• Nitrous Acid MeSH
• Plicamycin biosynthesis   MeSH
• Mutation * MeSH
• Mutagens MeSH
• Cobalt Radioisotopes MeSH
• Streptomyces metabolism   MeSH
• Ultraviolet Rays MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Nitrous Acid MeSH
• Plicamycin MeSH
• Mutagens MeSH
• Cobalt Radioisotopes MeSH

• MeSH
• Anthraquinones metabolism   MeSH
• Time Factors MeSH
• Chromatography, Thin Layer MeSH
• Fermentation MeSH
• Glucosides biosynthesis   MeSH
• Glycosides biosynthesis   MeSH
• Hydrogen-Ion Concentration MeSH
• Monosaccharides metabolism   MeSH
• Mutation MeSH
• Oligosaccharides metabolism   MeSH
• Buffers MeSH
• Sucrose metabolism   MeSH
• Spectrophotometry MeSH
• Streptomyces aureofaciens metabolism   MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anthraquinones MeSH
• Glucosides MeSH
• Glycosides MeSH
• Monosaccharides MeSH
• Oligosaccharides MeSH
• Buffers MeSH
• Sucrose MeSH