The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
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Volume 44, Issue 8
Displaying 1-17 of 17 articles from this issue
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  • MM 55266 AND MM 55268, GLYCOPEPTIDE ANTIBIOTICS PRODUCED BY A NEW STRAIN OF Amycolatopsis
    ISOLATION, PURIFICATION AND STRUCTURE DETERMINATION
    STEPHEN J. BOX, NIGEL J. COATES, CHRIS J. DAVIS, MARTIN L. GILPIN, CAT ...
    1991 Volume 44 Issue 8 Pages 807-813
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.807
    JOURNAL FREE ACCESS
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    Two novel glycopeptide antibiotics MM 55266 and MM 55268 containing fatty acid acyl functions, and of molecular formula C86H89N8O35Cl5 and C87H91N8O35C15, respectively, have been isolated and identified from a complex produced by Amycolatopsis sp. NCIB 40089. Fermentation conditions for their production, and methods for their isolation are described. Structures have been deduced by use of COSY and NOE NMR techniques and supported by chemical degradation studies. Both glycopeptides possessed good antibacterial activity against Gram-positive organisms.
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  • A NEW ANTIBIOTIC, OKICENONE
    I. TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL CHARACTERISTICS
    KANKI KOMIYAMA, SHINJI FUNAYAMA, YUMI ANRAKU, MASAMI ISHIBASHI, YOKO T ...
    1991 Volume 44 Issue 8 Pages 814-818
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.814
    JOURNAL FREE ACCESS
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    A new antibiotic, okicenone was isolated from the culture broth of Streptomyces sp. KO-3599. The antibiotic possesses cytocidal activity against mammalian tumor cells in vitro at concentrations of 0.53-11.0μg/ml whereas the antibiotic showed no antimicrobial activities against Gram-positive and Gram-negative bacteria, fungi or yeast at a concentration of 1, 000μg/ml.
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  • A NEW ANTIBIOTIC, OKICENONE
    II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE ELUCIDATION
    SHINJI FUNAYAMA, MASAMI ISHIBASHI, KANKI KOMIYAMA, SATOSHI OMURA
    1991 Volume 44 Issue 8 Pages 819-823
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.819
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    The structure of a new cytocidal antibiotic, okicenone was elucidated to be 3, 4-dihydro-4, 6, 9-trihydroxy-8-methyl-1(2H)-anthracenone on the basis of spectroscopic methods.
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  • HYDRAMYCIN, A NEW ANTITUMOR ANTIBIOTIC
    TAXONOMY, ISOLATION, PHYSICO-CHEMICAL PROPERTIES, STRUCTURE AND BIOLOGICAL ACTIVITY
    MINORU HANADA, KEIKO KANETA, YUJI NISHIYAMA, YUTAKA HOSHINO, MASATAKA ...
    1991 Volume 44 Issue 8 Pages 824-831
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.824
    JOURNAL FREE ACCESS
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    A new antitumor antibiotic hydramycin was isolated from the fermentation broth of Streptomyces violaceus P950-4 (ATCC 53807). It showed potent antibacterial and cytotoxic activity and increased the survival time of mice inoculated with P388 leukemia. A new structure related to the pluramycin group antibiotics was assigned by its spectroscopic experiments.
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  • A NOVEL HEPATOPROTECTIVE γ-LACTONE, MH-031
    I. DISCOVERY, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURAL ELUCIDATION
    YUMIKO ITOH, HIROSHI SHIMURA, MAYUMI ITO, NAOHARU WATANABE, MICHIO YAM ...
    1991 Volume 44 Issue 8 Pages 832-837
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.832
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    A new subspecies of Streptomyces rishiriensis A-5969 (PERM BP-1394) was isolated and shown to produce a novel α, β-unsaturated γ-lactone derivative, MH-031, which exhibited hepatoprotective activity in primary cultured rat hepatocytes intoxicated with D-galactosamine.
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  • THE STRUCTURE OF HENEICOMYCIN
    RAY S. DEWEY, OTTO D. HENSENS, ALAN W. DOUGLAS, GEORG ALBERS-SCHÖ ...
    1991 Volume 44 Issue 8 Pages 838-843
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.838
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    The antibiotic heneicomycin (1), C44H62N2O11, was isolated from cultures of Streptomyces filipinensis as an amorphous yellow powder. Mass spectral and NMR analysis showed the compound to be a deoxy modification of aurodox (2), a member of the elfamycin antibiotic family. A marked change in mass spectral fragmentation compared to aurodox and 1H NMR couplings indicated the absence of the hydroxyl at position 30 of aurodox (position 3 of the tetrahydropyran).
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  • ANTIBACTERIAL ACTIVITY OF 5-ACYLAMINOTHIAZOLE DERIVATIVES, SYNTHETIC DRUGS RELATED TO β-LACTAM ANTIBIOTICS
    BERNARD PIROTTE, JACQUES DELARGE, JACQUES COYETTE, JEAN-MARIE FRERE
    1991 Volume 44 Issue 8 Pages 844-853
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.844
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    Newly synthesized 5-acylaminothiazolium salts and one 5-acylaminothiazolidine, considering their chemical structure and reactivity, have been proposed as potential inhibitors of bacterial serine DD-peptidases. A moderate antibiotic activity with (5-phenylacetylamino-3-thiazolio)acetate and (5-phenylacetylaminothiazolidin-3-yl)acetic acid was observed on Staphylococcus aureus ATCC 25923. The methyl- and tert-butyl esters of the thiazolium salt have shown lower MIC values. Moreover, when introduced into an exponential growth phase culture of S. aureus, the three active thiazolium salts induced a partial lysis indicating an impairing of the bacterial cell wall biosynthesis. The observed time-dependent binding of the best compound to the PBPs of S. aureus was too slow and occurred at too high concentrations to account for its MIC value. Consequently, the antibiotic activity of the thiazolium salts on the S. aureus cells seems not to be satisfactorily explained by a penicillin-like interaction with the PBPs.
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  • CEPHALOSPORIN ANTIBIOTICS
    I. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 3-THIAZOLIOMETHYL DERIVATIVES
    EIJI NAKAYAMA, KOICHI FUJIMOTO, SHIGEKI MURAMATSU, MASAO MIYAUCHI, KAT ...
    1991 Volume 44 Issue 8 Pages 854-863
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.854
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    The synthesis and the structure-activity relationships of 3-thiazoliomethyl cephalosporins are described. In a series of these parenteral compounds, 2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido group was found to be a favorable substituent for the C-7 position of the cephem nucleus. They showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including some β-lactamase producing species.
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  • CEPHALOSPORIN ANTIBIOTICS
    II. SYNTHESIS AND BIOLOGICAL PROPERTIES OF CS-461 AND RELATED COMPOUNDS
    EIJI NAKAYAMA, KATSUHIKO WATANABE, MASAO MIYAUCHI, KOICHI FUJIMOTO, SH ...
    1991 Volume 44 Issue 8 Pages 864-869
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.864
    JOURNAL FREE ACCESS
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    The synthesis, structure-activity relationships, and biological properties of 3-thiazoliomethyl cephalosporins are described. 7-[2-(2-Aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[5-(2-hydroxyethyl)-4-methylthiazoliomethyl]-3-cephem-4-carboxylate sulfate (CS-461) showed potent antibacterial activity against a wide variety of bacteria both in vitro and in vivo. Furthermore, CS-461 exhibited significantly low acute toxicity in mice.
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  • (6R, 8S)-(2-BENZIMIDAZOLYL)HYDROXYMETHYLPENICILLANIC ACIDS AS POTENT ANTIBACTERIAL AGENTS AND β-LACTAMASE INHIBITORS
    YUHPYNG L. CHEN, KIRK HEDBERG, KAREN GUARINO, JAMES A. RETSEMA, MARGAR ...
    1991 Volume 44 Issue 8 Pages 870-884
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.870
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    (6R, 8S)-(2-Benzimidazolyl)hydroxymethylpenicillanic acids (1a-1x) are potent antibacterial agents and β-lactamase inhibitors against Gram-positive bacteria and Haemophilus influenzae. The corresponding (6R, 8R)-isomers (2a-2x), the 6, 6-spiro benzimidazole-penam alcohol (3), (7R, 9S)-(2-benzimidazolyl)hydroxymethylcephalosporanic acid (4), and 6β-(2-benzimidazolyl)aminopenicillanic acid (5) are much less active as antibacterials or β-lactamase inhibitors. The syntheses and structure-activity relationships of these compounds are discussed. Antibacterial activity and β-lactamase inhibition data are presented.
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  • NAPHTHYRIDINOMYCIN-DNA ADDUCTS: A MOLECULAR MODELING STUDY
    M. B. COX, P. ARJUNAN, S. K. ARORA
    1991 Volume 44 Issue 8 Pages 885-894
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.885
    JOURNAL FREE ACCESS
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    Monocovalent groove binding complexes of antitumor antibiotic naphthyridinomycin and its analogs with DNA sequence d(ATGCAT)2 have been studied by molecular mechanics to understand which enantiomer of the drug and what chirality at C(7) of the drug are preferred for forming better drug-DNA adducts. The effect of hydroquinone intermediate and the substitution at C(11) on drug-DNA interactions have also been investigated. The results indicate that the enantiomer that forms the best adduct is different from the one reported earlier in the literature. The drug with an R configuration at C(7) is preferred for binding. The hydroquinone models do not necessarily provide a given analog of the drug with additional favorable DNA interactions. The substitution at-C(11) by OH provides the best binding model. This finding agrees well with the results from previous biochemical studies. The sequence specific studies indicate that the sequence d(ATGCAT)2 is slightly preferred over others.
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  • PURIFICATION OF LINCOSAMINIDE O-NUCLEOTIDYLTRANSFERASE FROM Streptomyces coelicolor MÜLLER
    V. P. MARSHALL, J. E. MCGEE, J. I. CIALDELLA, L. BACZYNSKYJ, D. G. CHI ...
    1991 Volume 44 Issue 8 Pages 895-900
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.895
    JOURNAL FREE ACCESS
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    An enzyme (lincosaminide O-nucleotidyltransferase) that catalyzes 3-(5'-ribonucleotidylation) of pirlimycin and several other lincosaminide antibiotics has been purified approximately 35-fold from cell-free extracts of Streptomyces coelicolor Müller NRRL 3532 (UC 5240). The crude enzyme was prepared using lysozyme and was treated with MnCl2 and (NH4)2SO4. Final purification was achieved by anion exchange chromatography. The pirlimycin reaction product was verified as being pirrimycin-3-(5'-adenylate) by NMR spectroscopy and MS. As a result of purification, this lincosaminide nucleotidylating and inactivating enzyme was separated from the macrolide phosphorylating enzyme also present in the cell-free extract.
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  • TOTAL SYNTHESIS AND BIOLOGICAL EVALUATION OF UNNATURAL (-)-MEDERMYCIN [(-)-LACTOQUINOM YCIN]
    KUNIAKI TATSUTA, HIDEKAZU OZEKI, MAMI YAMAGUCHI, MASASHI TANAKA, TOSHI ...
    1991 Volume 44 Issue 8 Pages 901-902
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.901
    JOURNAL FREE ACCESS
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  • STUDIES ON FREE RADICAL SCAVENGING SUBSTANCES FROM MICROORGANISMS
    II. NEOCARAZOSTATINS A, B AND C, NOVEL FREE RADICAL SCAVENGERS
    SHINICHIRO KATO, KAZUTOSHI SHINDO, YOKO KATAOKA, YUJI YAMAGISHI, JUNIC ...
    1991 Volume 44 Issue 8 Pages 903-907
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.903
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  • NOVEL ANTITUMOR ANTIBIOTICS, SAPTOMYCINS D AND E
    NAOKI ABE, NOBUYASU ENOKI, YASUKAZU NAKAKITA, HIDEAKI UCHIDA, RYOICHI ...
    1991 Volume 44 Issue 8 Pages 908-911
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.908
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  • SYNTHESES AND ENZYME INHIBITING ACTIVITIES OF CYCLOPHELLITOL ANALOGS
    KUNIAKI TATSUTA, YOSHIHISA NIWATA, KAZUO UMEZAWA, KAZUNOBU TOSHIMA, MA ...
    1991 Volume 44 Issue 8 Pages 912-914
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.912
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  • INHIBITION OF EPIDERMAL GROWTH FACTOR-INDUCED ACTIVATION OF PHOSPHOLIPASE C BY PSI-TECTORIGENIN
    MASAYA IMOTO, NAOMI SHIMURA, KAZUO UMEZAWA
    1991 Volume 44 Issue 8 Pages 915-917
    Published: August 25, 1991
    Released on J-STAGE: April 19, 2006
    DOIhttps://doi.org/10.7164/antibiotics.44.915
    JOURNAL FREE ACCESS
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