The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 33 , Issue 11
Showing 1-31 articles out of 31 articles from the selected issue
  • I. PRODUCING ORGANISM, FERMENTATION, ISOLATION AND CHARACTERIZATION
    MICHIKO TAKEUCHI, MASATOSHI INUKAI, RYUZO ENOKITA, SEIGO IWADO, SHUJI ...
    1980 Volume 33 Issue 11 Pages 1213-1219
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Strain No. 15748, identified as Streptomyces lydicus, produced a new antibiotic malioxamycin. Malioxamycin is a water-soluble, amphoteric antibiotic with low molecular weight, having a valine and a malic acid moieties in its structure. It gave a positive ninhydrin and ferric chloride reactions. Malioxamycin inhibited the growth of some Gram-negative bacteria by acting on peptidoglycan synthesis in the cell wall and produced spheroplasts from those sensitive bacteria.
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  • II. STRUCTURAL ELUCIDATION AND TOTAL SYNTHESIS
    SHUJI TAKAHASHI, MICHIKO TAKEUCHI, MASATOSHI INUKAI, MAMORU ARAI
    1980 Volume 33 Issue 11 Pages 1220-1223
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Malioxamycin (1) is a new antibiotic produced by Streptomyces lydicus No. 15748. The structure of malioxamycin has been determined by nmr and mass spectra to possess a hydroxamic acid bond between L-valine and D-malic acid. This structure was confirmed by total synthesis of the antibiotic with (R)-aminooxysuccinic acid and the active ester of L-valine.
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  • TAKU MIZUTANI, MICHIO YAMAGISHI, HIROSHI HARA, SADAFUMI OMURA, MASAHIR ...
    1980 Volume 33 Issue 11 Pages 1224-1230
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Lonomycin B (II), C44H75O14Na, m.p. 181-182°C, and lonomycin C (III), C43H73O14Na, m.p. 186-187°C, were isolated as their sodium salts from the fermentation broth of Streptomyces ribosidificus TM-481. Their physicochemical properties demonstrated that II and III are closely related congeners of lonomycin A (I). The identical mass spectra of methyl esters of I and II indicated that II is a stereoisomer of I. On the other hand, the mass spectrum of a methyl ester of III showed a peak at m/e 810 due to M+-H2O which is smaller by 14 mass units than the maximum peak at m/e 824 due to M+-H2O of the methyl esters of I and II.
    This result together with the elemental analysis strongly suggested that III is a demethyl derivative of I or II. II and III are slightly less active than I in their antimicrobial activities.
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  • MOTOO SHIBATA, MASARU UYEDA, YUTAKA KIDO, NORIO TOYA, RYUICHI NAKASHIM ...
    1980 Volume 33 Issue 11 Pages 1231-1235
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    From the results of taxonomic studies, Streptomyces sp. strain No. K-82 isolated from a soil sample collected in Kumamoto city, was identified as a strain belonging to Streptomyces lavendulae WAKSMAN & HENRICI 1948. The strain produced an active new antibiotic called K-82 A and minor components named the B complex. Antibiotic K-82 A was isolated as dark reddish needles by silica gel column chromatography and found to have both antibacterial activity and high phage induction activity. The K-82 B complex was found to consist of at least five components, among which K-82 B2 and B3 were isolated as crystals. Substance K-82 B2 was identified as benzoic acid from its physicochemical properties. Substance B3 like B2 had only marginal antibiotic activity.
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  • KAZUNORI OHBA, TAKASHI SHOMURA, TAKASHI TSURUOKA, SHOJI OMOTO, MICHIO ...
    1980 Volume 33 Issue 11 Pages 1236-1242
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    A new antibiotic, substance SF-1771, has been isolated from the fermentation broth of Streptomyces toyocaensis SF-1771. The antibiotic is highly active against Gram-positive and -negative bacteria and effective against sarcoma 180 cells of ascites type in mice . It belonged to the phleomycin-bleomycin group antibiotics, but has been differentiated from the known antibiotics by the physicochemical properties, chromatographic behaviours and amino acid analysis.
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  • TAKASHI SHOMURA, SHOJI OMOTO, KAZUNORI OHBA, HIROKO OGINO, MICHIO KOJI ...
    1980 Volume 33 Issue 11 Pages 1243-1248
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    A new type of bleomycin group antibiotic, SF-1961 was isolated from the fermentation broth of Streptomyces species. SF-1961 possessed β-amino-β-(4-amino-6-carboxypyrimidin-2-yl)-propionic acid instead of its 5-methyl derivative which was a common component of bleomycins and phleomycins.
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  • S. NARAYANAN, M. R. S. IYENGAR, P. L. GANJU, S. RENGARAJU, TAKASHI SHO ...
    1980 Volume 33 Issue 11 Pages 1249-1255
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    γ-Chloronorvaline (AL-719) and γ-hydroxynorvalinelactone (AL-719Y) were isolated from the culture broth of Streptomyces griseosporeus AL-719. Physico-chemical studies led to the structure elucidation of AL-719 and 719Y, with their respective configurations of (2S, 4S) and
    (2S, 4R). AL-719 shows antibacterial activity on a synthetic agar, especially against Pseudomonas aeruginosa, which was reversed by L-leucine. The producing strain AL-719 was characterized.
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  • I. DETECTION, ISOLATION AND CHARACTERIZATION
    WEN-CHIN LIU, GAIL ASTLE, ERRY SCOTT WELLS Jr., WILLIAM H. TREJO, PACI ...
    1980 Volume 33 Issue 11 Pages 1256-1261
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Micromonospora chalcea subsp. izumensis produces a novel β-lactamase inhibitor izumenolide (EM4615). Isolation of izumenolide was performed by extraction into butanol under acidic conditions and then back extraction into water at neutrality. The compound was precipitated from the aqueous phase by the addition of calcium or barium salts. Further purification was achieved by distribution in BuOH-1N NaOH. Izumenolide is a macrolide containing sulfate ester groups.
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  • II. BIOLOGICAL PROPERTIES
    KAREN BUSH, DANIEL P. BONNER, RICHARD B. SYKES
    1980 Volume 33 Issue 11 Pages 1262-1269
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Izumenolide is a potent inhibitor of β-lactamases, especially from Gram-negative bacteria. The I50 value of 0.01 μg/ml for TEM-2 β-lactamase, after 10 min preincubation, corresponds to a ratio of 7.6 moles inhibitor per mole of enzyme. The initial inhibitory reaction with TEM-2 β-lactamase exhibits mixed reaction kinetics, suggesting a possible overlapping binding site with the active center. TEM-2 β-lactamase is irreversibly inactivated by izumenolide in a biphasic reaction. Carbenicillin offers partial protection against inactivation. izumenolide exhibits limited antibiotic activity against some Gram-negative bacteria. Against β-lactamase producing bacteria izumenolide provides protection to ampicillin and cephaloridine but the protection is limited due to permeability problems associated with izumenolide entry into the cells.
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  • THE STRUCTURE OF ETHERICIN B, A NEW DIPHENYLETHER ANTIBIOTIC
    W. A. KÖNIG, R. KRAUSE, W. LOEFFLER, D. SCHANZ
    1980 Volume 33 Issue 11 Pages 1270-1273
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Ethericin B(Ia) was isolated together with ethericin A1) from fermentations of Aspeigillus funiculosus Tü 680. The structure of ethericin B was established as 4-carbethoxy-5, 5'-dihydroxy-3, 3'-dimethyl-diphenyl ether by chemical degradation, mass spectrometry, 1H-NMR and comparison with synthetic 4-carbethoxy-5, 5'-dimethoxy-3, 3'-dimethyl-diphenyl ether.
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  • TAKEO DEUSHI, TAKASHI YAMAGUCHI, KAZUHIRO KAMIYA, AKIO IWASAKI, TOSHIM ...
    1980 Volume 33 Issue 11 Pages 1274-1280
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Streptomyces sannanensis KC-7038 used for the production of sannamycins A and B has also produced another antibiotic sannamycin C, in the culture broth. Physico-chemical characterization revealed that sannamycin C is a new aminoglycoside antibiotic having 6-N-methylpurpurosamine
    C and 2-deoxy-3-epi-fortamine. Its 4-N-glycyl derivative indicated inhibitory activity against Gram-positive and Gram-negative bacteria containing aminogly-coside resistant strains.
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  • DAISHIRO IKEDA, YUKIO HORIUCHI, SHINICHI KONDO, HAMAO UMEZAWA
    1980 Volume 33 Issue 11 Pages 1281-1288
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    4-N, 6'-N, 3-O-Tridemethylistamycin A0 (9) and 6'-N, 3-O-didemethylistamycin A0 (15)
    were synthesized from 3, 2', 6'-tri-N-benzyloxycarbonyl-3', 4'-dideoxyneamine 1, 6-carbamate
    (1) through an aziridine derivative 6 by an analogous procedure employed in the total synthesis
    of istamycin A0 (19). Acylation of 15 with glycine at the 4-methylamino group gave 6'-N, 3-Odidemethylistamycin
    A (18) having interesting activities especially against pseudomonas, but
    4-N, 6'-N, 3-O-tridemethylistamycin A (12) derived from 9 showed only weak activity. Therefore,
    the 4-N-methyl group of istamycin A (20) is essential for the antimicrobial activity.
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  • TETSUO SUAMI, KIN-ICHI TADANO, KINYA MATSUZAWA
    1980 Volume 33 Issue 11 Pages 1289-1299
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Chlorination of antibiotic fortimicin A with triphenylphosphine and carbon tetrachloride
    has been attempted, and 2-chloro-, 2, 5-dichloro-, and 2-chloro-4-ene derivatives have been
    obtained. Successive dehalogenation of the chlorinated fortimicins A with tributylstannane
    gave the corresponding deoxyfortimicins A. Among five deoxyfortimicins A, 2-deoxyfortimicin
    A exhibits improved antimicrobial activity, compared to the parent fortimicin A.
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  • ROKURO OKAMOTO, TSUMORU FUKUMOTO, HIDEO NOMURA, KOHKI KIYOSHIMA, KENJI ...
    1980 Volume 33 Issue 11 Pages 1300-1308
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    By microbial transformation of tylosin (I), the following eight new acyl derivatives were obtained: 3-acetyltylosin (II), 3-propionyltylosin (III), 4''-butyryltylosin (IV), 4''-isovaleryltylosin (V), 3-acetyl-4''-butyryltylosin (VI), 3-acetyl-4''-isovaleryltylosin (VII), 3-propionyl-4''-butyryltylosin (VIII) and 3-propionyl-4''-isovaleryltylosin (IX).
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  • ROKURO OKAMOTO, MASAMI TSUCHIYA, HIDEO NOMURA, HIROSHI IGUCHI, KOHKI K ...
    1980 Volume 33 Issue 11 Pages 1309-1315
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    The antibacterial activity of acyl derivatives of tylosin were examined in vitro and in vitro. The 4''-acyl group in the acylated tylosins enhanced the antibacterial activity and antimycoplasmal activity against some macrolide-resistant strains. The orally administered 3-acetyl-4''-isovaleryltylosin produced a higher blood level in mice and rabbits than tylosin and a good therapeutic effect on the infection of Staphylococcus aureus Smith in mice.
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  • NUCLEAR MAGNETIC RESONANCE ANALYSIS OF APLASMOMYCIN AND DESBOROAPLASMOMYCIN
    TOM S. S. CHEN, CHING-JER CHANG, HEINZ G. FLOSS
    1980 Volume 33 Issue 11 Pages 1316-1322
    Published: 1980
    Released: April 12, 2006
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    The 360 MHz 1H NMR spectra of the boron-containing macrolide antibiotic aplasmomycin and of desboroaplasmomycin were analyzed to extract most of the parameters revealing the conformations of these compounds in CDCl3 solution. It was found that the conformation of aplasmomycin in CDCl3 solution is identical to that in the solid state and that removal of the boron atom from aplasmomycin results only in a slight conformational change of the molecule in CDCl3. All resonances observed in the 13C NMR spectrum of the antibiotic have been assigned on the basis of chemical shift theory, multiplicity analyses, single frequency proton decoupling experiments, comparison with several derivatives and model compounds, specific deuteration experiments, and analysis of one-bond carbon-carbon couplings of pairs of carbon atoms.
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  • DEMETHOXYCARBONYLATION, 10-EPIMERIZATION AND 4-O-METHYLATION OF ACLACINOMYCIN A
    HIROSHI TANAKA, TAKEO YOSHIOKA, YASUTAKA SHIMAUCHI, YASUE MATSUZAWA, T ...
    1980 Volume 33 Issue 11 Pages 1323-1330
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Demethoxycarbonyl derivatives of aclacinomycin A and of its 7-epimer, 10-epi-aclacinomycin
    A and 4-O-methylaclacinomycin A were chemically derived from aclacinomycin A.
    The cytotoxicity and inhibitory effects on RNA and DNA synthesis in cultured L1210 leukemia
    cells of the 4-O-methyl derivative approximated that of aclacinomycin A, while the demethoxycarbonyl
    derivatives and 10-epi-aclacinomycin A exhibited decreased activities in comparison
    with the parent compound.
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  • I. GLYCOSIDATION OF VARIOUS ANTHRACYCLINONES BY AN ACLACINOMYCINNEGATIVE MUTANT AND BIOSYNTHESIS OF ACLACINOMYCINS FROM AKLAVINONE
    TOSHIKAZU OKI, AKIHIRO YOSHIMOTO, YASUE MATSUZAWA, TOMIO TAKEUCHI, HAM ...
    1980 Volume 33 Issue 11 Pages 1331-1340
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    An aclacinomycin-negative mutant strain KE303 which required aklavinone aglycone for the production of anthracycline antibiotics was derived from Streptomyces galilaeus, and employed for the glycosidation of various anthracyclinones. ε-, γ- and β-Rhodomycinones, ε-isorhodomycinone, ε- and β-pyrromycinones and chemically modified aklavinones were found to be glycosidated to the biologically active anthracyclines, when they were fed to the growing culture. However, the feeding of daunomycinone, 13-deoxydaunomycinone, adriamycinone and steffimycinone did not yield any glycoside. The bioconversion of presumptive precursor glycosides revealed that aclacinomycin A is biosynthesized by the step-wise glycosidation from aklavinone via aklavin and MA144 S1.
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  • II. STRUCTURE OF NEW ANTHRACYCLINE ANTIBIOTICS OBTAINED BY MICROBIAL GLYCOSIDATION AND BIOLOGICAL ACTIVITY
    YASUE MATSUZAWA, AKIHIRO YOSHIMOTO, TOSHIKAZU OKI, HIROSHI NAGANAWA, T ...
    1980 Volume 33 Issue 11 Pages 1341-1347
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    New anthracycline antibiotics derived from ε-, γ- and β-rhodomycinones and ε-isorhodomycinone by the microbial glycosidation using an aclacinomycin-negative mutant, the strain KE303, of Streptomyces galilaeus MA144-M1 were studied to elucidate their structures and biological activities. These antibiotics were the products in which the anthracyclinones added as precursors were linked at C-7 or C-10 position with the same trisaccharide moiety (cinerulosyl-2-deoxyfucosyl-rhodosaminyl group) as in the parental antibiotic aclacinomycin A. In addition to antimicrobial activity, they exhibited the growth inhibition of cultured L1210 leukemia cells and the marked inhibition against DNA and RNA synthesis.
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  • PRODUCTION IN PENICILLIUM CHRYSOGENUM FERMENTATIONS
    STEVEN P. BRUNDIDGE, FEDERICO C. A. GAETA, DEREK J. HOOK, CHESTER SAPI ...
    1980 Volume 33 Issue 11 Pages 1348-1351
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    Analysis of a 13C NMR spectrum of a concentrated broth from Penicillium chrysogenum fermentation revealed the presence of penicillin V and 6-oxo-piperidine-2-carboxylic acid (1) as the principal constituents. The latter lactam, identical to an authentic sample prepared by the cyclization of α-aminoadipic acid was present to the extent of 28mol% of penicillin V. The lactam isolated from the broth was nearly racemic, having a slight excess of the L-isomer. This isolation provides further evidence regarding the biosynthetic precursors of the hydrophobic penicillins.
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  • T. F. MICH, G. G. HUANG, P. W. K. WOO, J. P. SANCHEZ, C. L. HEIFETZ, D ...
    1980 Volume 33 Issue 11 Pages 1352-1356
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    A new broad spectrum semisynthetic cephalosporin (CN-92, 982) was prepared from the condensation of an acetylaminoacylaminophenyl pyridone with trans-7-[(D-2-phenylglycyl) amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-Δ3-cephem-4-carboxylic acid. The new cephalosporin displayed an in vitro antibacterial spectrum similar to other cephaloglycine types such as cefoperazone and SM-1652. The compound produced a high and prolonged blood level following a single intramuscular dose in a dog.
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  • TETSUO OKA, KAZUKO HASHIZUME, HIRONORI FUJITA
    1980 Volume 33 Issue 11 Pages 1357-1362
    Published: 1980
    Released: April 12, 2006
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    The inhibitory activities of representative β-lactam compounds, such as penicillins G and N, cephalosporins C and G, clavulanic acid, nocardicin A and thienamycin against Escherichia coli KN-126 and Bacillus megaterium KM peptidoglycan transpeptidases were studied. Their modes of action against E. coli are discussed on the basis of the results and the published binding data for penicillin binding proteins. The effects of modifications at position 3 and 7 of the cephalosporin and those at α-carbon of the benzyl side-chain of cephalosporin G and penicillin G were studied. The introduction of an amino group at this position in cephalosporin G together with the removal of an acetoxy group from the acetoxymethyl group at position 3 reduced the inhibitory activity against E. coli transpeptidase considerably. The activity was restored by the replacement of the methyl group at position 3 of cephalexin with chlorine. The restoration was accompanied by about 15-fold increase in the lytic activity of cephachlor against E. coli.
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  • KINETICS OF [14C]BENZYLPENICILLIN BINDING, TEMPERATURE SENSITIVITY AND RELEASE OF [14C]BENZYLPENICILLIN FROM THE COMPLEX
    SUSUMU HORIKAWA, HISAYOSHI NAKAZAWA, HIROSHI OGAWARA
    1980 Volume 33 Issue 11 Pages 1363-1368
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
    On the membrane-bound penicillin-binding proteins (PBP) of Streptomyces cacaoi and S. clavuligerus, the kinetics of [14C]benzylpenicillin binding, the temperature sensitivity, the release of [14C]benzylpenicillin from the [14C]benzylpenicillin-PBP complexes and the changes of the PBP patterns during the growth cycle were examined. All the PBP in both strains, especially PBP in S. clavuligerus, had very low affinity for benzylpenicillin, comparing with other bacteria. As for the temperature sensitivity of the binding ability, all the PBP in S. cacaoi were highly sensitive to heat, while PBP-3 in S. clavuligerus retained the binding activity after incubation at 60°C for 10 minutes. The release of [14C]benzylpenicillin from the complexes with PBP-1, PBP-2 in S. cacaoi and PBP-3 in S. clavuligerus was relatively fast initially. However, this soon reached a plateau and the complexes retained [14C]benzylpenicillin even after prolonged incubation. During the growth cycle, the PBP patterns in S. cacaoi did not change significantly. However, in S. clavuligerus, a band of molecular weight of about 120, 000 daltons was observed only in the membrane fraction of early log phase, and PBP-1 (Mr=83, 000) and PBP-2 (Mr=79, 000) appeared only slightly in this phase.
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  • CAROL W. MOORE
    1980 Volume 33 Issue 11 Pages 1369-1375
    Published: 1980
    Released: April 12, 2006
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    Two of eight mutants (bmr) isolated in Saccharomyces cerevisiae on the basis of their increased resistance to lethal effects of antitumor bleomycins (BM), and about two-thirds of 180 yeast mutants (bms) isolated on the basis of their increased sensitivities to cell-killing by phleomycins (PM) or BM were sensitive to one or more of the agents UV, X-rays or hydrogen peroxide. Thus these mutants are likely to be altered in processes acting directly or indirectly on DNA damage. The remaining six bmr mutants and approximately 60 bms mutants appear as resistant as the parent strain to cell-killing by UV or X-rays, and are likely therefore, to be altered in cell wall or membrane function. A genetic basis for the phenotypes of some of the bmr and bms mutants has been established.
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  • ITSUO KUROBANE, LEO C. VINING, A. GAVIN MCINNES, NANCY N. GERBER
    1980 Volume 33 Issue 11 Pages 1376-1379
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
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  • III. A COMMENT ON THE STRUCTURE OF GENTAMICIN A
    HUBERT MAEHR, JOANNE SMALLHEER, CARL P. SCHAFFNER
    1980 Volume 33 Issue 11 Pages 1380-1382
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
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  • J. P. BENDIRDJIAN, B. FOUCHER, J. P. FILLASTRE
    1980 Volume 33 Issue 11 Pages 1383-1385
    Published: 1980
    Released: April 12, 2006
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  • W. L. BAKER, BARBARA D. BLAKE
    1980 Volume 33 Issue 11 Pages 1386-1387
    Published: 1980
    Released: April 12, 2006
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  • MASAHITO NAKAYAMA, AKIO IWASAKI, SHIGERU KIMURA, TOSHIMI MIZOGUCHI, SO ...
    1980 Volume 33 Issue 11 Pages 1388-1390
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
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  • L. A. DOLAK, L. E. JOHNSON
    1980 Volume 33 Issue 11 Pages 1391-1394
    Published: 1980
    Released: April 12, 2006
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  • SATOSHI OMURA, AKIRA NAKAGAWA, HIROSHI HASHIMOTO, RUIKO OIWA, YUZURU I ...
    1980 Volume 33 Issue 11 Pages 1395-1396
    Published: 1980
    Released: April 12, 2006
    JOURNALS FREE ACCESS
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