Biosynthesis of anthracycline antibiotics by Streptomyces galilaeus. I. Glycosidation of various anthracyclinones by an aclacinomycin-negative mutant and biosynthesis of aclacinomycins from aklavinone.

Oki, Taikan; Yoshimoto, Akihiro; Matsuzawa, Yasue; Takeuchi, Tomio; Umezawa, Hamao

doi:10.7164/antibiotics.33.1331

Cited by 48 publications

(14 citation statements)

References 15 publications

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“…Stepwise glycos ylation of aklavinone to aclacinomycins was described by Oki et al (1980). The model of glycosylation based on the mutants obtained by screening (Fig.…”

Section: Mutants Producing Aminoglycosidesmentioning

confidence: 99%

Isolation and characterization of aclacinomycin A-non-producing Streptomyces galilaeus (ATCC 31615) mutants

et al. 1994

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Twelve mutants of Streptomyces galilaeus (ATCC 31615) blocked in the production of aclacinomycin A, an anthracycline antibiotic with significant antitumour activity, accumulated intermediates of the biosynthesis of aclacinomycins and several anthracyclines with variant sugar moieties. Three of these aklavinone glycosides have not been described before. Mutant strains H028, H061 and H036 were blocked before the formation of aklavinone, a common intermediate for most anthracyclines. Strain H039 accumulated aklavinone and H026, H035, H038 and H054 had mutations that changed glycosylation of aklavinone. Characterization of the mutants and their products is described.

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“…Stepwise glycos ylation of aklavinone to aclacinomycins was described by Oki et al (1980). The model of glycosylation based on the mutants obtained by screening (Fig.…”

Section: Mutants Producing Aminoglycosidesmentioning

confidence: 99%

Isolation and characterization of aclacinomycin A-non-producing Streptomyces galilaeus (ATCC 31615) mutants

et al. 1994

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“…Compound 1 was previously reported to be a biosynthetic shunt product of block mutant strains of Streptomyces galilaeus as part of a study to understand the biosynthesis of aclacinomycins (Oki et al, 1980;Tobe et al, 1982). On the other note, 2 was reported as an isomer of Bisanhydro-δ-rhodomycinone and Bisanhydro-ε-rhodomycinone (Brockmann and Brockmann, 1963).…”

Section: Antibacterial Compounds From Streptomyces Griseorubens Straimentioning

confidence: 99%

Anthracycline Shunt Metabolites From Philippine Marine Sediment-Derived Streptomyces Destroy Cell Membrane Integrity of Multidrug-Resistant Staphylococcus aureus

et al. 2020

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The rise of antibiotic resistance (ABR) and the drying up of the pipeline for the development of new antibiotics demands an urgent search for new antibiotic leads. While the majority of clinically available antibiotics were discovered from terrestrial Streptomyces, related species from marine sediments as a source of antibiotics remain underexplored. Here, we utilized culture-dependent isolation of thirty-five marine sediment-derived actinobacterial isolates followed by a screening of their antibacterial activity against multidrug-resistant S. aureus ATCC BAA-44. Our results revealed that the crude extract of Streptomyces griseorubens strain DSD069 isolated from marine sediments collected in Romblon, Philippines displays the highest antibacterial activity, with 96.4% growth inhibition. The S. aureus ATCC BAA-44 cells treated with crude extract of Streptomyces griseorubens strain DSD069 showed cell membrane damage as demonstrated by (a) leakage and loss of vital cell constituents, including DNA and proteins, (b) irregular shrinkage of cells, and (c) increase membrane permeability. The antibiotic compounds were identified as Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone with MIC value of 6.25 µg/mL and 50.00 µg/mL, respectively. Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone are shunt metabolites in the biosynthesis of anticancer anthracycline derivatives namely doxorubicin, daunorubicin, and cinerubins. It is rare, however, that shunt metabolites are accumulated during fermentation of marine sediment-derived Streptomyces strain without genetic modification. Thus, our study provides evidence that natural bacterial strain can produce Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone as antibiotic leads to combat ABR.

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“…1 ) Thus, 320 mg of a-citromycinone was glycosylated with a total of 32 liters of conversion culture. The glycosylated products were extracted from the myc.elial cake with a total of 10 liters of acetone.…”

mentioning

confidence: 99%

New Anthracycline Antibiotic CG12 Obtained by Microbial Glycosidation ofα-Citromycinone

Johdo¹,

Yoshimoto²,

Ishikura³

et al. 1986

Agricultural and Biological Chemistry

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Biosynthesis of anthracycline antibiotics by Streptomyces galilaeus. I. Glycosidation of various anthracyclinones by an aclacinomycin-negative mutant and biosynthesis of aclacinomycins from aklavinone.

Cited by 48 publications

References 15 publications

Isolation and characterization of aclacinomycin A-non-producing Streptomyces galilaeus (ATCC 31615) mutants

Isolation and characterization of aclacinomycin A-non-producing Streptomyces galilaeus (ATCC 31615) mutants

Anthracycline Shunt Metabolites From Philippine Marine Sediment-Derived Streptomyces Destroy Cell Membrane Integrity of Multidrug-Resistant Staphylococcus aureus

New Anthracycline Antibiotic CG12 Obtained by Microbial Glycosidation ofα-Citromycinone

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