The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 41 , Issue 2
Showing 1-22 articles out of 22 articles from the selected issue
  • ISOLATION, STRUCTURE DETERMINATION, AND BIOSYNTHESIS
    WILLIAM L. RUSSELL, RAMESH C. PANDEY, CARL P. SCHAFFNER, HENRY M. FALE ...
    1988 Volume 41 Issue 2 Pages 149-156
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Micromonospora purpureochromogenes subsp, halotolerans was found to produce crisarnicin C, a novel antibiotic, together with crisamicin A. Crisamicin C was purified by silica gel column chromatography and its physico-chemical properties, structure and biosynthesis were studied. Crisamicin C, mp 260°C (dec), showed UV maxima at 392 (ε 9, 497), 261 (ε 32, 959) and 232 nm (ε 24, 623) in CH3CN, and gave an IR spectrum with absorbances at 1782 (lactone), 1705 and 1655 (quinone) cm-1. Crisamicin C plasma desorption mass spectrornetry (PD-MS) m/z 615.9 ((M+H)+, hydroquinone) was 16 amu higher than crisamicin A PD-MS m/z 600 ((M+H)+, hydroquinone) suggesting that the two antibiotics differ by one additional oxygen in crisamicin C. Analysis of 1H and 13C NMR spectra, in comparison with those of crisamicin A, indicated that crisamicin C was the 4'a, 10'a epoxide derivative of crisamicin A. Carbon-thirteen labeled acetate feeding experiments were used to confirm the positions of the epoxide and other structural features. Crisamicin C was a more potent antibiotic than crisamicin A, but shared the same spectrum of antimicrobial activity (Grampositive only).
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  • A. D. ARGOUDELIS, L. BACZYNSKYJ, W. J. HAAK, W. M. KNOLL, S. A. MIZSAK ...
    1988 Volume 41 Issue 2 Pages 157-169
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Paulomycin A2 (C34H46N2O17S), paulomycin C (C32H42N2O17S), paulomycin D (C31H40N2O17S), paulomycin E (C29H36N2O16S) and paulomycin F (C29H38N2O16S) have been isolated from fermentations of Streptomyces paulus strain 273. The structure of these compounds was determined using NMR and mass spectroscopic techniques. The new paulomycins, like paulomycins A and B (J. Antibiotics 35: 285-294, 1982) are highly active mainly against Gram-positive organisms.
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  • I. SYNTHESIS, ANTIBACTERIAL ACTIVITY AND ORAL ABSORPTION OF NEW 3-(O-SUBSTITUTED)-7β-[D-α-AMINO-α-(4-HYDROXYPHENYL)ACETAMIDO]CEPHALOSPORINS
    CHIHIRO YOKOO, MASAMI GOI, AKIRA ONODERA, MITSUO MURATA, TAKATOSHI NAG ...
    1988 Volume 41 Issue 2 Pages 170-180
    Published: February 25, 1988
    Released: April 19, 2006
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    The synthesis, antibacterial activity and oral absorption of new 7β-[D-α-amino-α-(4-hydroxyphenyl)acetamido]cephalosporins (1) with various O-substituents at the C-3 position of a cephalosporin nucleus are described. Of these, the cephalosporins (1b-1e) having an alkoxycarbonylmethoxy group at the C-3 position showed good oral absorption in rats as well as potent activity against Gram-positive bacteria. The structure-activity relationships of 1 are also presented.
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  • II. SYNTHESIS, ANTIBACTERIAL ACTIVITY AND ORAL ABSORPTION OF 3-ALKOXYCARBONYLMETHOXY-7β-[(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-(O-SUBSTITUTED OXYIMINO)-ACETAMIDO]CEPHALOSPORINS
    CHIHIRO YOKOO, MASAMI GOI, AKIRA ONODERA, MITSUO MURATA, TAKATOSHI NAG ...
    1988 Volume 41 Issue 2 Pages 181-192
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The synthesis, antibacterial activity and oral absorption in rats of 3-alkoxycarbonylmethoxy-7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(O-substituted oxyimino)acetamido]cephalosporins (1) are described. In this cephalosporin series, 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)acetamido]cephalosporins (Ib, 1i and 1j) with a lower alkoxycarbonylmethoxy group at the C-3 position of a cephem nucleus exhibited not only potent activity against Gram-negative bacteria but also good oral absorption in rats. Structure-activity relationships of 1 are also presented.
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  • BARBARA STEFANSKA, MARIA DZIEDUSZYCKA, MARIA BONTEMPS-GRACZ, EDWARD BO ...
    1988 Volume 41 Issue 2 Pages 193-198
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Eleven N-enamine derivatives of daunorubicin and of its 5-imino analogue as well as of doxorubicin have been synthesized and evaluated for antileukemic activity in vitro and in vivo. Comparison of biological activities of examined compounds with other enamine derivatives of daunorubicin, reported earlier by us, has indicated that the optimal activity is shown by N-(1-carboethoxypropen-1-yl-2)daunorubicin.
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  • PETER D. SENTER, DAVID R. LANGLEY, WALTER E. MANGER, DOLATRAI M. VYAS
    1988 Volume 41 Issue 2 Pages 199-201
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    7-Cysteaminomitosane (RR-150) has been reported to be superior to mitomycin C against P388 leukemia and B-16 melanoma in mice and is less leukopenic. Studies reported here indicated the absence of a free thiol group in RR-150 and therefore the structure was incorrectly assigned. Reaction of mitomycin A. with either 2-aminoethanethiol or cystamine gave the same disulfide, 7-N, 7'-N'-dithiodiethylenedimitomycin C, which is the newly proposed structure for RR-150. Attempts to produce 7-cysteaminomitosane by reduction of the disulfide have not succeeded because of its apparent instability.
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  • JILL BARBER, JOHN A. CARVER, REUBEN LEBERMAN, GRAHAM M. V. TEBB
    1988 Volume 41 Issue 2 Pages 202-206
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The binding of the antibiotic kirromycin (mocimycin) to its target protein, bacteriadelongation factor Tu (EF-Tu), has been studied by 1H NMR spectroscopy using deuterated protein. Narrow lines were observed in the spectrum of the unbound protein (due to residual protons) and in the spectrum of the kirromycin-EF-Tu complex. The spectrum of the complex has been compared with the spectra of the unbound protein and the unbound drug, and the results are interpreted in terms of the mode of antibiotic action of kirromycin.
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  • MARIE-LAURE HOURDOU, FRANÇHISE BESSON, GEORGES MICHEL
    1988 Volume 41 Issue 2 Pages 207-211
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The biosynthesis of the β-amino acid components of iturins A was studied in comparison to the biosynthesis of fatty acids. Palmitic acid was incorporated into the lipid moiety of iturins A when it was added to the culture medium of the iturin producer Bacillus subtilis. Addition of unlabeled palmitic acid enhanced the formation of straight-chain β-amino acids and addition of valine or leucine increased the production of branched β-amino acids. These mod fications correlated with modifications in the corresponding biosynthesized fatty acids.
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  • BERNARD FABRE, ELISE ARMAU, GILLES ETIENNE, FRÉDÉRIC LEG ...
    1988 Volume 41 Issue 2 Pages 212-219
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A simple and selective assay system was developed in the search for new insecticidal substances from Actinomycetales strains propagated on solid culture media. The strains were first tested for their ability to produce antimicrobial compounds. Only strains displaying weak or no activity were retained and screened in the insecticidal bioassay. Microbial solid cultures were given as food to larvae and to adults of Musca domestica to detect insecticide producers. A second phase, after extraction of the active compounds, consisted of an evaluation of the insecticidal potency and a primarily biological identification of the products synthesized by the selected strain.
    Of 6, 280 actinomycete strains which were screened, 47 were active but only 30 of these were finally chosen in the second phase of screening. All these strains, except one, produced known metabolites such as piericidins, avermectins or valinomycin. The one strain, CL307-24, and its insecticide products appeared novel and will be the topic of further study.
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  • TETSUSHI SAINO, TETSUYA SOMENO, SHIN-ICHI ISHII, TAKAAKI AOYAGI, HAMAO ...
    1988 Volume 41 Issue 2 Pages 220-225
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Thirty analogues of leupeptin were synthesized and examined for their inhibitory activities against trypsin, papain, plasmin, kallikrein, thrombin and urokinase in vitro. Benzoyland α-naphthalenesulfonyl-L-leucyl-L-argininal were 8 times more inhibitory to papain, benzyloxycarbonyl-L-pyroglutamyl-L-leucyl-L-argininal 10 times more to trypsin and plasmin, and DL-2-pipecolyl-L-leucyl-L-argininal 25 times more to kallikrein than leupeptin. Against urokinase, only L-pyroglutamyl-L-leucyl-L-argininal exhibited a potent inhibitory activity. α-Naphthalenesulfonyl-, dansyl- and benzyloxycarbonyl-(2S, 3R)-3-ammo-2-hydroxy-4-phenylbutyryl-L-leucyl-L-argininal were inhibitory to thrombin.
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  • HIROYUKI ANZAI, YOICHI KUMADA, OSAMU HARA, TAKESHI MURAKAMI, REIKO ITO ...
    1988 Volume 41 Issue 2 Pages 226-233
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    We have developed a method for gene replacement in Streptomyces hygroscopicus which permits introduction of an in vitro derived mutation carried on a plasmid into the chromosome. We constructed the plasmid pMSB212 which can replicate in S. hygroscopicus and contains the step5 gene of the bialaphos biosynthetic pathway which was inactivated by a frame-shift mutation caused by filling in the cohesive ends of the EcoR I site in the structural gene. pMSB212 was introduced into a bialaphos producer strain and by protoplast regeneration of the primary thiostrepton-resistant transformants, non-producing mutants, were obtained. Biochemical and genetical analyses indicated that these mutants were specifically blocked by introduction of the frame-shift mutation in the step5 gene on the chromosome. This method will enable us to obtain isogenic mutants of known genes and to identify new genes encoded on a cloned fragment.
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  • HIROSHI KURAMOCHI, MASAHARU HIRATSUKA, SAKIKO NAGAMINE, KATSUTOSHI TAK ...
    1988 Volume 41 Issue 2 Pages 234-238
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The amine oxidase activities contained in calf serum and human serum were detected at levels of 90.8 and less than 0.1 nmol O2/minute/ml serum, respectively, by measuring oxygen consumption coupled with spermidine oxidation. Deoxyspergualin (NKT-01) and spergualin (SGL) containing spermidine in their structure were also oxidized in calf serum at the rate of 3.6 and 11.6 nmol O2/minute/ml serum, respectively. To investigate whether amine oxidase is essential for NKT-01 and SGL to exhibit their antiproliferative activities or not, the in vitro activities of NKT-01, SGL and polyamines against LI210 cells were examined in the presence of calf or human serum. Polyamines exhibited antiproliferative activity only in the presence of calf serum, while NKT-01 and SGL inhibited cell growth in the presence of both calf and human serum. In the presence of calf serum the activity of NKT-01 was inhibited by aminoguanidine, an amine oxidase inhibitor. Aminoguanidine did not inhibit the activity of NKT-01 in the presence of human serum. The activity of NKT-01 was shown at much lower concentrations in the presence of human serum than that in the presence of calf serum, and was strongly dependent on incubation time. The in vivo activities of NKT-01, SGL and SGL derivatives correlated with their in vitro activities in the presence of human serum. These results suggest that the in vivo antitumor activities of NKT-01, SGL and SGL derivatives may be attributed to a mechanism different from those of amine oxidase-oxidized product and represent a novel growth inhibitory action.
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  • SATOSHI OKUNO, ISAO MAEZAWA, YOSHIMITSU SAKUMA, TADAHIRO MATSUSHITA, T ...
    1988 Volume 41 Issue 2 Pages 239-246
    Published: February 25, 1988
    Released: April 19, 2006
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    The serum concentrations, urinary and biliary excretions of six penicillin derivatives including aspoxicillin (ASPC) were studied in rats and the correlation between the values of pharmacokinetic parameters thus obtained and the Rm values measured by means of reversed phase TLC were analyzed.
    Among the penicillins studied, the hydrophilicity of amoxicillin was the highest (the lowest Rm value), which was followed by those of ASPC, ampicillin, p-hydroxypiperacillin, dehydroxyaspoxicillin and piperacillin in descending order. These Rm values were then correlated with the AUC values at 20 mg/kg of dosing, giving the results that more hydrophilic penicillins having a hydroxyl group show higher serum concentrations as well as greater AUC values. The studies of correlation between the Rm values and the urinary or biliary excretion revealed that hydrophilic penicillins were almost excreted into urine, but more hydrophobic ones were mainly eliminated into bile.
    From the above results, a hydroxyl group introduced to the phenyl group of ASPC was considered to have a role that increases the hydrophilicity of ASPC, giving higher and longer persistency of the serum levels and increasing the excretion of drugs into urine.
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  • HIROSHI TOMODA, HIDETOSHI KUMAGAI, YOKO TAKAHASHI, YOSHITAKE TANAKA, Y ...
    1988 Volume 41 Issue 2 Pages 247-249
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • KAZUHIKO OTOGURO, AKIRA NAKAGAWA, SATOSHI OMURA
    1988 Volume 41 Issue 2 Pages 250-252
    Published: February 25, 1988
    Released: April 19, 2006
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  • A. L. LABORDE, J. I. CIALDELLA, F. B. SHILLIDAY, V. P. MARSHALL
    1988 Volume 41 Issue 2 Pages 253-254
    Published: February 25, 1988
    Released: April 19, 2006
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  • C. HÖNLINGER, W. A. HAMPEL, M. RÖHR, C. P. KUBICEK
    1988 Volume 41 Issue 2 Pages 255-257
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • YOSHITAKE TANAKA, KEIKO KIMURA, YASUKO KOMAGATA, KAZUO TSUZUKI, HIROSH ...
    1988 Volume 41 Issue 2 Pages 258-260
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • AKIRA OKURA, MASAAKI ISHIZUKA, TOMIO TAKEUCHI
    1988 Volume 41 Issue 2 Pages 261-263
    Published: February 25, 1988
    Released: April 19, 2006
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  • NAN-JIN WANG, YUAN FU, GUI-HUA YAN, GUANG-HONG BAO, CHANG-FU XU, CUN-H ...
    1988 Volume 41 Issue 2 Pages 264-267
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • YAEKO KONDA, AKIRA NAKAGAWA, YOSHIHIRO HARIGAYA, MASAYUKI ONDA, ROKURO ...
    1988 Volume 41 Issue 2 Pages 268-270
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • TOYOSHIGE ENDO, KAORI KOBAYASHI, NAOHIRO NAKAYAMA, TERUO TANAKA, TAKAS ...
    1988 Volume 41 Issue 2 Pages 271-273
    Published: February 25, 1988
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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