The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 44 , Issue 6
Showing 1-19 articles out of 19 articles from the selected issue
  • I. TAXONOMY, PRODUCTION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
    TAKAAKI AOYAGI, SHIGEMI YOSHIDA, NAOKO MATSUDA, TAKAKO IKEDA, MASA HAM ...
    1991 Volume 44 Issue 6 Pages 573-578
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Leuhistin has been isolated from the culture broth of Bacillus laterosporus BMI156-14F1 as part of a program designed to find microorganism-produced inhibitors of aminopeptidase M (AP-M). It was purified by use of column chromatography on Sepabeads SP206, Amberlite IRC-50, MCI gel CHP-20P and Sephadex G-10 and then isolated as colorless needles. Leuhistin inhibits AP-M strongly and it also inhibits AP-A and AP-B weakly. It is competitive with the substrate, and the inhibition constant (Ki) was 2.3 × 10-7 M.
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  • II. STRUCTURE DETERMINATION OF LEUHISTIN
    SHIGEMI YOSHIDA, HIROSHI NAGANAWA, TAKAAKI AOYAGI, TOMIO TAKEUCHI, YAS ...
    1991 Volume 44 Issue 6 Pages 579-581
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Leuhistin, a new inhibitor of aminopeptidase M, has been isolated from the culture broth of Bacillus laterosporus BMI156-14F1. The structure of leuhistin was determined by NMR studies. X-Ray and chemical analysis confirmed the absolute structure to be (2R, 3S)-3-amino-2-hydroxy-2-(1H-imidazol-4-ylmethyl)-5-methylhexanoic acid.
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  • TAXONOMY, FERMENTATION, ISOLATION AND PHYSICO-CHEMICAL CHARACTERIZATION
    MASAHIRO AOKI, TATSUO OHTSUKA, MASAYOSHI YAMADA, YOSHIKO OHBA, HLROYUK ...
    1991 Volume 44 Issue 6 Pages 582-588
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Cyclothiazomycin is a novel renin inhibitor produced by Streptomyces sp. NR0516. It was isolated from fermentation broth by extraction with butyl alcohol, QAE-Toyopearl column chromatography and preparative HPLC. Cyclothiazomycin, which was determined to be a unique polythiazole-containing bicyclic peptide, exhibited inhibitory activity against human plasma renin with IC50 being 1.7 μM.
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  • I. TAXONOMY, FERMENTATION, ISOLATION, CHARACTERIZATION AND BIOLOGICAL ACTIVITIES
    TAKAFUMI ISHII, TSUNEAKI HIDA, TAKENORI ISHIMARU, SHIGEMI IINUMA, KATS ...
    1991 Volume 44 Issue 6 Pages 589-599
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A novel nonsteroidal aromatase inhibitor, TAN-931, was isolated from the culture filtrate of a soil isolate fungus, No. 8974. The strain was identified as Penicillium funiculosum No. 8974. TAN-931 inhibited human placental and rat ovarian aromatase activity, and the IC50 value was 17.2 and 162 μm, respectively. The inhibition of human placental aromatase was uncompetitive with respect to androstenedione conversion with a Ki value of 40 μM. When TAN-931 was subcutaneously administered at doses of 25, 50 and 100 mg/kg (once/day, × 4) to 20-day-old female Sprague-Dawley rats treated with gonadotropin, the plasma estradiol-17 β level and the weight of ovaries and uterus were markedly reduced in a dose-dependent manner. The in vivo inhibitory activity of TAN-931 was more potent than that of 4-hydroxyandrostenedione.
    Consecutive administration of TAN-931 (100 mg/kg, sc, twice/day, × 7) to 9-week-old male Sprague-Dawley rats did not induce any adrenal hypertrophy even though administration of aminoglutethimide caused 2-fold enlargement of the adrenal under the same conditions.
    Specific binding of TAN-931 to the estrogen receptor from a human breast cancer cell line, MCF-7, was not detected.
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  • II. STRUCTURE ELUCIDATION, CHEMICAL MODIFICATION AND BIOLOGICAL ACTIVITY
    TSUNEAKI HIDA, TAKAFUMI ISHII, TSUNEO KANAMARU, MASAYUKI MUROI
    1991 Volume 44 Issue 6 Pages 600-612
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The structure of TAN-931, a novel nonsteroidal aromatase inhibitor, was determined by chemical reactions and spectral analyses including 2D NMR experiments to be 4-(2, 6-dihydroxybenzoyl)-3-formyl-5-hydroxybenzoic acid. Several derivatives of TAN-931 were prepared, and it was found that the 3-formyl and 2'- and/or 6'-hydroxyl groups play an important role in its inhibitory activity. Among the compounds synthesized, 4-(2, 6-dihydroxybenzoyl)-3-formyl-5-methoxy-N, N-dimethylbenzamide was found to be more effective than TAN-931 when administered orally.
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  • TAXONOMY, FERMENTATION, ISOLATION, CHEMICAL CONVERSIONS, AND PHYSICO-CHEMICAL AND BIOCHEMICAL PROPERTIES
    Y. K. TONY LAM, DEBRA BOGEN, RAYMOND S. CHANG, KRISTINE A. FAUST, OTTO ...
    1991 Volume 44 Issue 6 Pages 613-625
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The discovery and physico-chemical characterization of three novel and minor virginiamycin M1 analogs as potent gastrin antagonists from a culture of a strain of Streptomyces olivaceus are described. These analogs are L-156, 586, L-156, 587 and L-156, 588. They are, respectively, 15-dihydro-13, 14-anhydro-, 13, 14-anhydro- and 13-desoxy-analogs of virginiamycin M1. We also chemically converted virginiamycin M1 (via L-156, 587) to L-156, 586 and its unnatural epimer, L-156, 906. These analogs are competitive and selective antagonists of gastrin and brain cholecystokinin binding at nanomolar concentrations. These are the most potent gastrin/brain cholecystokinin antagonists from natural products. The same compounds showed poor Gram-positive antibiotic activity versus virginiamycin M1. Structurally related Gram-positive antibiotics, griseoviridin and madumycin I, were inactive in gastrin and brain cholecystokinin binding at up to 100 μM.
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  • ENZYMATIC BROMINATION OF NIKKOMYCIN Z
    HEINRICH DECKER, UWE PFEFFERLE, CHRISTIANE BORMANN, HANS ZÄHNER, ...
    1991 Volume 44 Issue 6 Pages 626-634
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Two brominated nikkomycins were produced by enzymatic halogenation of nikkomycin Z in the presence of a nonheme bromoperoxidase isolated from Streptomyces aureofaciens Tü 24. The monobrominated and dibrominated nikkomycin Z derivatives were substituted at the hydroxypyridyl moiety of the N-terminal amino acid of nikkomycin Z at position C-6''' (ZBr) or C-4''' and C-6''' (ZBr2).
    The brominated nikkomycin Z derivatives had a decreased affinity to chitin synthase of Coprinus cinereus as compared to nikkomycin Z and exhibited a low inhibitory activity towards various fungi and yeasts.
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  • MASAHIRO AOKI, HARUYOSHI SHIRAI, NOBORU NAKAYAMA, YOSHIKO ITEZONO, MIT ...
    1991 Volume 44 Issue 6 Pages 635-645
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Avidinorubicin (MW 1, 214, C60H86N4O22) was isolated from the cultured broth of strain NR0576 (which was identified as Streptomyces avidinii STAPLEY et al.) by butyl alcohol extraction, Sephadex LH-20 column chromatography and preparative HPLC. Avidinorubicin inhibited thrombin-induced platelet aggregation with an IC50 being 7.9 μM and was determined to be a novel anthracycline possessing two units of a new aminosugar, avidinosamine, in place of two decilonitrose groups in decilorubicin.
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  • TETSURO YAMASAKI, YUKIO NARITA, HIDEAKI HOSHI, SHIMPEI ABURAKI, HIDEO ...
    1991 Volume 44 Issue 6 Pages 646-658
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The synthesis and biological properties of 1-N-[4-(substituted)amidino and guanidino-2-hydroxybutyryl]kanamycins A and B are described. Reaction of 3, 3'', 6'-tri-N-tert-butoxycarbonylamikacin with an appropriate amidinating or guanidinating reagent and subsequent deblocking gave a series of amikacin derivatives having an amidino or guanidino group on the 4'''-position. The corresponding kanamycin B analogs were also prepared by a similar procedure. Among these derivatives, 1-N-(4-formamidino- and guanidino-2-hydroxybutyryl)kanamycins A (7a and 7k) and B (11 and 14) exhibited antibacterial activity similar to the corresponding 4-amino analogs. The nephrotoxic potential of selected compounds is also briefly discussed.
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  • SUN HEE KIM, KIMITAKE OKAZAKI, TAKAYOSHI OKABE, TOSHIO NISHIMURA, TADA ...
    1991 Volume 44 Issue 6 Pages 659-664
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The relationship between the activity and the chemical structure of cadeguomycin (CDM, 7-carboxy-7-deazaguanosine) was studied with six analogs of CDM. Both activities of CDM, enhancing the incorporation of [3H]thymidine in K562 cells and potentiating the cytotoxicity of cytosine arabinoside for K562 cells, were significantly augmented by the replacement of the 7-carboxyl group with cyano (CDM-CN) or formyl (CDM-CHO), but they were not changed by the replacement with methyl. The activities were almost completely diminished by the replacement of ribose with arabinose, but the simultaneous replacement of carboxyl and ribose with formyl and arabinose showed higher activities than those of CDM. The replacement of 7-carboxy-7-deazaguanine with 7-carboxy-7-deazainosine markedly weakened the activity. CDM-CN and CDM-CHO at 0.2 μg/ml significantly potentiated the activity of cytosine arabinoside against MOLT-3 cells but CDM at 1 μg/ml did not. These results indicate that the ribose and guanine moieties in the CDM molecule are very important for its activity. Also replacing the carboxyl group at the C-7 position with cyano or formyl group is a useful way to strengthen the CDM activity. These compounds would effectively potentiate cytosine arabinoside against various kinds of tumor cells which CDM could not do.
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  • STRUCTURE AND ABSOLUTE CONFIG-URATION OF NAPHTHOMEVALIN, A NEW DIHYDRO-NAPHTHOQUINONE ANTIBIOTIC FROM Streptomyces sp.
    THOMAS HENKEL, AXEL ZEECK
    1991 Volume 44 Issue 6 Pages 665-669
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • SM 196 A AND B, NOVEL BIOLOGICALLY ACTIVE ANGUCYCLINONES FROM Streptomyces sp.
    SUSANNE GRABLEY, PETER HAMMANN, KLAUS HÜTTER, HEINZ KLUGE, RALF T ...
    1991 Volume 44 Issue 6 Pages 670-673
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • CONWAY C. CHANG, GEORGE O. MORTON, JOHN C. JAMES, MARSHALL M. SIEGEL, ...
    1991 Volume 44 Issue 6 Pages 674-677
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • MIKAEL BOLS, NIELS RASTRUP ANDERSEN, JYTTE HANSEN, AYDIN ZEYNEL OCAKTA ...
    1991 Volume 44 Issue 6 Pages 678-679
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • HIDEAKI HOSHI, SHIMPEI ABURAKI, TETSURO YAMASAKI, TAKAYUKI NAITO, HIRO ...
    1991 Volume 44 Issue 6 Pages 680-682
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • SHIGEMI YOSHIDA, TAKAAKI AOYAGI, TOMIO TAKEUCHI
    1991 Volume 44 Issue 6 Pages 683-684
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • YOSHIHIRO TESHIMA, KAZUO SHIN-YA, AKIRA SHIMAZU, KEIKO FURIHATA, HA SA ...
    1991 Volume 44 Issue 6 Pages 685-687
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • JAMES B. MCALPINE, SUSAN J. SWANSON, MARIANNA JACKSON, DAVID N. WHITTE ...
    1991 Volume 44 Issue 6 Pages 688-690
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • WLODZIMIERZ KURYLOWICZ
    1991 Volume 44 Issue 6 Pages 691-692
    Published: June 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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