The Journal of Antibiotics

NEW ISOFLAVONES, INHIBITING CATECHOL-O-METHYLTRANSFERASE, PRODUCED BY STREPTOMYCES

HIDEO CHIMURA, TSUTOMU SAWA, YOSHIKI KUMADA, HIROSHI NAGANAWA, MEIKI M ...

1975 Volume 28 Issue 9 Pages 619-626
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.619

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In the screening of catechol-O-methyltransferase inhibitors in streptomyces culture filtrates, three new isoflavones were isolated. Their structures were shown to be 3', 5, 7-trihydroxy-4', 6-dimethoxyisoflavone (I), 3', 5, 7-trihydroxy-4', 8-dimethoxyisoflavone (II), 3', 8-dihydroxy-4', 6, 7-trimethoxyisoflavone (III). I and II inhibited both catechol-O-methyltransferase and dopa decarboxylase, and showed hypotensive action. III was a specific inhibitor of catechol-O-methyltransferase, and showed no hypotensive action.

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MUTATIONAL BIOSYNTHESIS OF A NEW ANTIBIOTIC, STREPTOMUTIN A, BY AN IDIOTROPH OF STREPTOMYCES GRISEUS

K. NAGAOKA, A. L. DEMAIN

1975 Volume 28 Issue 9 Pages 627-635
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.627

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Microoganisms producing antibiotics have been genetically converted by earlier workers to mutants which cannot produce antibiotic without supplementation with a moiety of the antibiotic. These antibiotics include neomycin, kanamycin, paromomycin, butirosin, sisomicin, ribostamycin and novobiocin. Success has not been reported for organisms producing guanidinocyclitol antibiotics such as streptomycin. We mutagenized conidia of the streptomycin-producing Streptomyces griseus strain 7-455F3 with nitrosoguanidine at pH 7.0. Non-producers of streptomycin were visually selected by the agar-plug technique using Bacillus subtilis. We successfully isolated mutant MIT-A5 which produces no streptomycin unless streptidine is added to the agar medium. The streptidine-dependent phenotype was confirmed in submerged culture in flasks. Attempts to produce new antibiotics by feeding aminocyclitols to mutant MIT-A5 failed. However a new antibiotic (streptomutin A) was produced by supplementation with the guanidinocyclitol, 2-deoxystreptidine. We propose the term "mutational biosynthesis" for the production of new metabolites by the use of mutants blocked in the biosynthetic pathway to the secondary metabolite. We further propose the term "idiotroph" to properly describe such mutants.

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A NEW ANTIBIOTIC, FUMARAMIDMYCIN

I. PRODUCTION, BIOLOGICAL PROPERTIES AND CHARACTERIZATION OF PRODUCER STRAIN

HIROMI B. MARUYAMA, YASUJI SUHARA, JUNKO SUZUKI-WATANABE, YOSHIFUMI MA ...

1975 Volume 28 Issue 9 Pages 636-647
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.636

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A new antibiotic, fumaramidmycin, has been isolated from a streptomycete NR-7GGl which was characterized and named Streptomyces kurssanovii. The strain produced the antibiotic only when grown on agar plates but not in the submerged culture broth, where the contact with the vegetative mycelia appears to cause the inactivation of the antibiotic. The antibiotic shows an antimicrobial activity against both Gram-positive and Gram-negative bacteria.

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A NEW ANTIBIOTIC, FUMARAMIDMYCIN

II. ISOLATION, STRUCTURE AND SYNTHESES

YASUJI SUHARA, HIROMI B. MARUYAMA, YOSHIAKI KOTOH, YUMIKO MIYASAKA, KA ...

1975 Volume 28 Issue 9 Pages 648-655
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.648

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A new antibiotic fumaramidmycin produced by Streptomyces kurssanovii NR-7GGl was isolated as colorless crystals. The structure was shown to be N-(phenylacetyl) fumaramide. Starting from fumaramic acid, fumaramidmycin has been synthesized in good yield, in which the key stage involves N-acylated imino ether formation followed by mild acid hydrolysis. Five analogues of fumaramidmycin have also been prepared.

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PLATOMYCINS A AND B

I TAXONOMY OF THE PRODUCING STRAIN AND PRODUCTION, ISOLATION AND BIOLOGICAL PROPERTIES OF PLATOMYCINS

SEIGO TAKASAWA, ISAO KAWAMOTO, ITARU TAKAHASHI, MASAHIRO KOHAKURA, RYO ...

1975 Volume 28 Issue 9 Pages 656-661
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.656

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Two new antibiotics. platomycins A and B. belonging to the phleomycin-bleomycin family, were isolated from the culture filtrate of Streptosporangium sp. MK-78. This strain has been identified as a new variety of Streptosporangium violaceochromogenes. Both platomycins A and B are active against a variety of Gram-positive and Gram-negative bacteria, and also inhibit solid Sarcoma 180 and EHRLICH ascites carcinoma.

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PLATOMYCINS A AND B

II. PHYSICOCHEMICAL PROPERTIES

SEIGO TAKASAWA, ISAO KAWAMOTO, SEIJI SATO, RYOSUKE YAHASHI, RYO OKACHI ...

1975 Volume 28 Issue 9 Pages 662-667
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.662

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Platomycins A and B, two new antibacterial and antitumor antibiotics were found to belong to the phleomycin-bleomycin family, being closely related to bleomycins B. The two ahtibiotics have been differentiated from all of the reported phleomycins and bleomycins.

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CHEMICAL-IONIZATION MASS SPECTROMETRY OF β-LACTAM ANTIBIOTICS

LESTER A. MITSCHER, H. D. HOLLIS SHOWALTER, KUNIKATSU SHIRAHATA

1975 Volume 28 Issue 9 Pages 668-675
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.668

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Chemical-ionization (CI) mass spectra are described for methyl esters of eight clinically significant penicillins and their breakdown products. These substances give spectra with very few fragment ions and contain easily discernible protonated molecule ions. The main cleavage reaction is postulated to involve a retro 2+2 DIELS-ALDER-type fragmentation of the β-lactam ring liberating one fragment (m/e=174) that is characteristic of the penicillin nucleus and a second fragment that is molecule specific, as it contains the elements of the side chain. The other fragment ions, though interesting, are of minor intensity. The free acids, on the other hand, fragment more extensively because of their relative instability and lack of volatility. These spectra resemble electron impact spectra more closely and, though they encode more structural information, are less reproducible from run to run. The ease with which the esters can be made and the relative simplicity of their CI mass spectra make this method significant for the identification and characterization of β-lactam antibiotics.

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ACTION OF BLEOMYCIN ON THE BACTERIOPHAGE T7 INFECTION

KAZUO SHISHIDO, ATSUKO WATARAI, SACHIO NAITO, TADAHIKO ANDO

1975 Volume 28 Issue 9 Pages 676-680
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.676

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A decrease in production of bacteriophage T7 was observed in bleomycin-treated Escherichia coli B cells. Bleomycin was found to shorten the eclipse in phage growth. A T7 early gene product, the T7-specific RNA polymerase which catalyzes the transcription of late gene appeared more rapidly in the bleomycin-treated cells than in the non-treated cells. The rate of phage adsorption increased to some extent in drug-treated cells. A possible mechanism to explain the mode of action of bleomycin is discussed.

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TRANSDUCTION OF DRUG RESISTANCE TO TETRACYCLINE, CHLORAMPHENICOL, MACROLIDES, LINCOMYCIN AND CLINDAMYCIN WITH PHAGES INDUCED FROM STREPTOCOCCUS PYOGENES

KIMIKO UBUKATA, MASATOSHI KONNO, RYOCHI FUJII

1975 Volume 28 Issue 9 Pages 681-688
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.681

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Strains of Streptococcus pyogenes isolated from pediatric patients with acute infections which were resistant to one or more of the antibiotics, tetracycline (TC), chloramphenicol (CP), macrolide antibiotics (erythromycin, kitasamycin, oleandomycin, josamycin), lincomycin (LCM) and clindamycin (CLM), were used for transduction of drug resistance. These drug-resistant strains were treated with mitomycin C to induce phages and transduction of drug resistance was attempted by means of phages so induced. It was found that transduction of resistance to the above antibiotics was possible. The transductants obtained on TC-containing selective agar plate were resistant to TC alone while those produced on CP- or erythromycin (EM)-containing selective agar plate were resistant to CP, macrolide antibiotics (Mac), LCM and CLM. From this finding, it was inferred that transduction of resistance to TC, CP, Mac, LCM and CLM via phages occurred in two different patterns, i. e., transfer of resistance to TC alone and that of resistance to CP, Mac, LCM and CLM. All of the transductants obtained were found to belong to group A. In T-typing, they were of the same T-12 type as the donor and recipient strains in a majority of cases though some were not typable.

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DEGRADATION OF PHOSPHOLIPID IN PSEUDOMONAS AERUGINOSA INDUCED BY POLYMYXIN B

TOMONOBU KUSANO, KAZUO IZAKI, HAJIME TAKAHASHI

1975 Volume 28 Issue 9 Pages 689-695
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.689

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Effects of polymyxin B on the synthesis and degradation of lipid, ribonucleic acid (RNA) and protein in Pseudomonas aeruginosa were investigated. It was found that polymyxin B caused a marked degradation of the lipid fraction which was prelabeled with (³H-2)-glycerol. Thin-layer chromatographic analysis indicated that the main degraded lipids were phosphatidylethanolamine and phosphatidylglycerol, which constituted 80%, and 15% of the total phospholipids of this organism, respectively. Polymyxin B also inhibited synthesis of RNA and protein in vivo. The severe inhibition of the uptake of labeled amino acids by polymyxin B indicated that the observed inhibition of RNA and protein synthesis possibly occurred at the level of substrate transports. The degradation of phospholipid might account for the defective membrane activities.

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GENTAMICIN ACCUMULATION BY SENSITIVE STRAINS OF ESCHERICHIA COLI AND PSEUDOMONAS AERUGINOSA

L.E. BRYAN, H. M. VAN DEN ELZEN

1975 Volume 28 Issue 9 Pages 696-703
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.696

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Gentamicin accumulation with time shows multiphasic kinetics in strains of Escherichia coli and Pseudomonas aeruginosa. All but first phase accumulation may be prevented or reduced by inhibitors of electron transport, by a sulfhydryl poison, by agents which uncouple electron transport and oxidative phosphorylation and by an inhibitor of protein synthesis. The phases of accumulation which are sensitive to these inhibitors are required for loss of cell viability. Gentamicin can be extracted from cells in an unchanged form as judged by paper chromatography and is concentrated 4 to 250 times over extracellular concentrations within the bacterial cell. Gentamicin accumulation has been shown to occur before there is any evidence of release of acid-soluble ³H-adenine from cells. These data demonstrate that productive gentamicin accumulation capable of causing cell death is by active transport.

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A FACILE PREPARATION OF ERYTHRONOLIDE A OXIME

RONALD A. LEMAHIEU, MATHEW CARSON, RICHARD W. KIERSTEAD

1975 Volume 28 Issue 9 Pages 704
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.704

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A NOVEL INTRAMOLECULAR DISPLACEMENT REACTION OF 5-O-DESOSAMINYLERYTHRONOLIDE A OXIME

RONALD A. LEMAHIEU, JOHN F. BLOUNT, RICHARD W. KIERSTEAD

1975 Volume 28 Issue 9 Pages 705-706
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.705

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STRUCTURE OF EVERNINOMICIN B

ASHIT K. GANGULY, ANIL K. SAKSENA

1975 Volume 28 Issue 9 Pages 707-709
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.707

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STRUCTURE OF EVERNINOMICIN C

ASHIT K. GANGULY, SOL SZMULEWICZ

1975 Volume 28 Issue 9 Pages 710-712
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.710

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A NEW ANTIBIOTIC, C-9154

TORU HASEGAWA, MITSUKO ASAI, KONOMI HAIBARA, TOGO YAMANO, HIDESUKE IWA ...

1975 Volume 28 Issue 9 Pages 713-716
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.713

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A NEW ANTIBIOTIC, BACIPHELACIN

HISAYOSHI OKAZAKI, TOYOKAZU KISHI, TERUHIKO BEPPU, KEI ARIMA

1975 Volume 28 Issue 9 Pages 717-719
Published: 1975
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.28.717

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