The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 46 , Issue 1
Showing 1-24 articles out of 24 articles from the selected issue
  • I. TAXONOMY, YIELD IMPROVEMENT AND FERMENTATION
    JUNKO WATANABE, NORIKO FUJISAKI, KUMIKO FUJIMORI, YOJIRO ANZAI, SHOICH ...
    1993 Volume 46 Issue 1 Pages 1-10
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Streptomyces sp. NR0489 produces tetronothiodin, a novel brain-type cholecystokinin receptor antagonist. This species was differentiated from its related species S. gelaticus, S. griseolus and S. hydrogenans on the basis of their cultural characteristics, such as the utilization of carbohydrates and the presence or absence of various enzymatic activities. We applied the DNA-DNA hybridization method using photobiotin, which proved the genetic difference between the four species mentioned above. The yield improvement effort including single colony isolation, mutation, and protoplast regeneration together with medium optimization resulted in more than an 81-fold increase of the productivity of tetronothiodin as compared to that of the wild type strain.
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  • II. ISOLATION, CHARACTERIZATION AND BIOLOGICAL ACTIVITIES
    TATSUO OHTSUKA, HIROMICHI KOTAKI, NOBORU NAKAYAMA, YOSHIKO ITEZONO, NO ...
    1993 Volume 46 Issue 1 Pages 11-17
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A novel cholecystokinin type-B receptor antagonist named tetronothiodin has been isolated by column chromatography and preparative HPLC from the fermentation broth of Streptomyces sp. NR0489. Tetronothiodin inhibited the binding of CCK8 (C-terminal octapeptide of cholecystokinin) to rat cerebral cortex membranes (CCK type-B receptors) with an IC50 of 3.6nM, whereas it did not inhibit CCK8 binding to rat pancreatic membranes (CCK type-A receptors). It also inhibited CCK8 induced Ca2+ mobilization in GH3 cells, a rat anterior pituitary cell line, but was without effect on the basal cytosolic Ca2+ concentration. This finding indicated tetronothiodin was an antagonist of CCK type-B receptors.
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  • III. STRUCTURAL ELUCIDATION
    TATSUO OHTSUKA, NOBORU NAKAYAMA, YOSHIKO ITEZONO, NOBUO SHIMMA, TOSHIK ...
    1993 Volume 46 Issue 1 Pages 18-24
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Tetronothiodin (1) is a potent and selective cholecystokinin type B (CCK-B) receptor antagonist produced by Streptomyces sp. NR0489. Its structure was elucidated to be a macrocyclic compound comprising cyclohexene, α-acyltetronic acid and tetrahydrothiophene moieties based on various 2D NMR experiments on 1 and its dihydro derivative. The stereochemistries for the cyclohexene and tetrahydrothiophene rings were elucidated based on the analysis of NOEs obtained by NOESY experiments and NOE difference spectroscopy. The relative configuration of the cyclohexene moiety in 1 was revealed to be the same as that of the corresponding part in kijanimicin and chlorothricin, which can be structurally related to 1 in terms of their containing a cyclohexene ring with a spirotetronic acid in the molecule.
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  • TAXONOMY, FERMENTATION, ISOLATION, STRUCTURES AND BIOLOGICAL ACTIVITIES
    YOSHIMI NIHEI, HARUAKI YAMAMOTO, MASAMI HASEGAWA, MINORU HANADA, YASUO ...
    1993 Volume 46 Issue 1 Pages 25-33
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    New 5-lipoxygenase inhibitors, designated epocarbazolins A and B, were isolated from the culture broth of Streptomyces anulatus T688-8. These compounds showed potent rat 5-lipoxygenase inhibitory activity with weak antibacterial activity. Structural studies revealed that epocarbazolins are new carbazole antibiotics having a novel substitution pattern and an epoxide in the side chain.
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  • I. PRODUCTION, TAXONOMY OF THE PRODUCING ORGANISM AND BIOLOGICAL ACTIVITY
    MARIANNA JACKSON, JAMES P. KARWOWSKI, PATRICK E. HUMPHREY, WILLIAM L. ...
    1993 Volume 46 Issue 1 Pages 34-38
    Published: January 25, 1993
    Released: April 19, 2006
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    A novel antibiotic complex, named the calbistrins, has been discovered in the culture broth of a soil fungus. The producing organism, designated AB 1875C-28, was identified as a strain of Penicillium restrictum. Calbistrin A, the most potent of the 4-membered complex, has MICs of 0.78 μg/ml against Candida albicans. Only poor activity is observed against non-candida yeasts, filamentous fungi and bacteria.
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  • II. ISOLATION AND ELUCIDATION OF STRUCTURE
    GREGORY M. BRILL, RANDAL H. CHEN, RONALD R. RASMUSSEN, DAVID N. WHITTE ...
    1993 Volume 46 Issue 1 Pages 39-47
    Published: January 25, 1993
    Released: April 19, 2006
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    The novel antifungal agents, calbistrins A, B, C and D have been isolated from a strain of Penicillium restrictum (AB 1875C-28). The four congeners were separated by bioactivity directed fractionation using countercurrent chromatography and preparative-HPLC. NMR studies revealed that the calbistrins each contain a carboxylic acid conjugated tetraene attached through an aliphatic ester linkage to a hexahydronaphthalene system.
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  • JIN-ZHONG XAIO, SHIGENORI KUMAZAWA, NOBUJI YOSHIKAWA, TAKASHI MIKAWA, ...
    1993 Volume 46 Issue 1 Pages 48-55
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Novel antifungal antibiotics, designated as dactylfungins A (1) and B (3), were isolated from the culture broth of Dactylaria parvispora D500. Dactylfungins A and B were found to be new substances containing an α-pyrone and a γ-pyrone ring, respectively, which conjoined with a polyalcohol moiety and a long side chain, based on NMR spectral analyses. The antibiotics were active against Candida pseudotropicalis and other fungi, with an MIC value at less than 10 μg/ml.
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  • II. NEW ANTHRACYCLINE METABOLITES PRODUCED BY A BLOCKED MUTANT STRAIN RPM-5
    AKIHIRO YOSHIMOTO, SHIZUKA FUJII, OSAMU JOHDO, KATSURO KUBO, HIROSHI N ...
    1993 Volume 46 Issue 1 Pages 56-64
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A daunorubicin-blocked mutant strain RPM-5 derived from a new baumycin-producing Streptomyces sp. D788 accumulated a major precursor metabolite D788-1 (10-carboxy-13-deoxocarminomycin) and nine minor metabolites in the culture broth. Five among them were new with a substituent at C-10 or the altered side chains at C-9. Isolation, purification and identification of all anthracycline metabolites produced by strain RPM-5 are described with their antitumor activities against L1210 cells.
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  • TAXONOMY, FERMENTATION AND BIOLOGICAL ACTIVITY
    NOZOMI KATAYAMA, YUKIMASA NOZAKI, KENJI OKONOGI, SETSUO HARADA, HIDEO ...
    1993 Volume 46 Issue 1 Pages 65-70
    Published: January 25, 1993
    Released: April 19, 2006
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    A Gram-negative bacterium was found to produce new iron-containing peptide antibiotics, ferrocins A, B, C and D, and the producing bacterium was characterized and identified as Pseudomonas fluorescens YK-310. These new antibiotics showed antibacterial activity against Gram-negative bacteria in vitro. Although the ferrocins showed similar antibacterial activity against both Escherichia coli and Pseudomonas aeruginosa on the standard assay media, they showed strong therapeutic effects selectively against P. aeruginosa in experimentally infected mice.
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  • YASUHIRO MINE, YUJI WATANABE, HIROSHI SAKAMOTO, KAZUO HATANO, KYOICHIR ...
    1993 Volume 46 Issue 1 Pages 71-87
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    FK037 is a new parenteral cephalosporin, which offers some advantages over the commercially available parenteral cephalosporins. It demonstrated potent broad-spectrum activity against clinical isolates of Gram-positive bacteria including methicillin-resistant staphylococci, and Gram-negative bacteria including Pseudomonas aeruginosa. Against clinical isolates of aerobic Gram-positive bacteria, FK037, like cefpirome, demonstrated more potent activity than ceftazidime, cefoperazone and ceftizoxime. It is noteworthy that FK037, on the basis of the MIC90s, was the most active of all the cephalosporins tested against methicillin-resistant Staphylococcus aureus (MRSA). It was similar in activity to cefpirome against methicillin-sensitive S. aureus (MSSA). Against clinical isolates of aerobic Gram-negative bacteria, FK037, like cefpirome, was superior to cefoperazone, similar to ceftazidime and inferior to ceftizoxime in activity. Against P. aeruginosa, FK037 was superior to cefoperazone, similar or slightly superior to cefpirome and inferior to ceftazidime in activity. However, FK037 exhibited significant activity against Citrobacter and Enterobacter which were highly resistant to ceftazidime, cefoperazone and ceftizoxime. FK037 had an advantage in that its bactericidal activity against S. aureus, Escherichia coli and P. aeruginosa at sub-MICs (1/2 or 1/4 the MIC) was much stronger than those of cefpirome and ceftazidime. Moreover, it exhibited potent bactericidal activity against MSSA, MRSA and P. aeruginosa in a pharmacokinetic in vitro model simulating human plasma concentrations after intravenous dosage of 0.125, 1.0 and 1.0g, respectively. FK037 inhibited essential penicillin-binding proteins (PBPs), 1, 2 and 3 of S. aureus with a 50% inhibitory concentration (I50) of 0.58 μg/ml or lower. Of essential PBPs 3, Ia and Ib of E. coli and P. aeruginosa, FK037 inhibited PBP 3 at the lowest I50 (0.03 and 0.04 μg/ml, respectively) and PBPs Ia and Ib with I50 values of 2.7 μg/ml or lower. FK037, like cefpirome, was highly stable to hydrolysis by various β-lactamases except Ic cephalosporinase from Bacteroides fragilis, and had extremely low affinity for β-lactamases. Therefore, FK037 was more potent than ceftazidime in activity against β-lactamase-producing bacteria except P. aeruginosa and Serratia marcescens. The ability of FK037 to penetrate the outer membrane of E. coli was slightly higher than that of ceftazidime, but slightly lower than that of cefpirome.
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  • YASUHIRO MINE, YUJI WATANABE, HIROSHI SAKAMOTO, KAZUO HATANO, YOSHIMI ...
    1993 Volume 46 Issue 1 Pages 88-98
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    FK037 has potent therapeutic activity against lethal systemic infections and experimental local infections due to a wide variety of Gram-positive and Gram-negative bacteria such as staphylococci, Streptococcus pneumoniae, Enterobacteriaceae and Pseudomonas aeruginosa in mice. In murine systemic infections, FK037 was the most effective of the cephalosporins and imipenem tested against highly methicillin-resistant Staphylococcus aureus (H-MRSA). It was more effective than ceftazidime against selected strains of S. aureus and Enterobacteriaceae, except Serratia marcescens and P. aeruginosa against which FK037 was as effective as ceftazidime and was as effective as cefpirome against all organisms tested, except MRSA and P. aeruginosa against which FK037 was more effective than cefpirome. These results correlated well with its in vitro activity. In murine local infections, with few exceptions, FK037 was more effective than ceftazidime and cefpirome against Klebsiella pneumonia in ED50 values and against methicillin-sensitive S. aurens (MSSA) subcutaneous abscess, pyelonephritis with Staphylococcus epidermidis, E. coli and P. aeruginosa, intrauterine infections with S. aureus and E. coli in reducing the number of viable bacteria in the abscess, kidneys and uterus. It is noteworthy that the therapeutic effects of FK037 were more potent than had been anticipated from its in vitro activity against local infections with staphylococci and P. aeruginosa when compared with ceftazidime or cefpirome. In addition, the therapeutic effects of FK037 were equipotent or superior to those of cefpirome and ceftazidime against pneumonia due to MSSA, K. pneumoniae and P. aeruginosa in reducing the number of viable bacteria in the lungs in mice using an in vivo pharmacokinetic model simulating human plasma concentrations after drip infusion of usual clinical doses (0.25 to 1.0g for MSSA, 0.063 to 0.125g for K. pneumoniae and 1.0 to 2.0 g for P. aeruginosa). FK037 induced an in vivo post-antibiotic effect (PAE) of 3.4 hours against a thigh infection with MSSA in neutropenic mice. These results strongly suggest that it has potential for clinical use against various infections due to bacteria which include staphylococci and P. aeruginosa.
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  • YASUHIRO MINE, YUJI WATANABE, HIROSHI SAKAMOTO, KAZUO HATANO, KYOICHIR ...
    1993 Volume 46 Issue 1 Pages 99-119
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    FK037 exhibits potent in vitro and in vivo antibacterial activity against methicillin-resistant staphylococci. In in vitro studies, FK037 was the most active of the cephalosporins and imipenem tested against the highly methicillin-resistant staphylococci (MIC > 100 μg/ml). Only 2 of 57 strains of highly methicillin-resistant Staphylococcus aureus (H-MRSA) had a FK037 MIC value of 50 μg/ml. On the other hand, 55, 40 and 19 strains had MICs of 50 or ≥ 100 μg/ml to cefpirome, flomoxef and imipenem, respectively. Against 13 strains of highly methicillin-resistant coagulase-negative staphylococci (H-MRCNS), FK037 inhibited all the strains at ≤ 50/ μg/ml, but there were many strains highly resistant to the reference drugs with MICs of ≥ 100 μg/ml. The influence of culture conditions such as low temperature, high inoculum and supplementation with 4% NaCl on the anti-MRSA activity of FK037 was less than those with cefpirome, flomoxef and imipenem. The in vitro frequency of spontaneous mutant cells highly resistant to FK037 in MRSA was lower than that to cefpirome and flomoxef. These findings were supported by lack of colonies inside the inhibition zone demarcated by FK037 in a disk sensitivity test, although many colonies proliferated inside the inhibition zone demarcated by flomoxef and imipenem. The increase in MIC of FK037 against a MRSA strain during subculture in the presence of the drug was smaller than that noted with the reference drugs. FK037 had higher affinity and faster binding for the PBP 2a of MRSA than that of the reference drugs. Moreover, the capacity to induce PBP 2a was lower for FK037 than that of cefpirome but higher than that of flomoxef. In an in vitro pharmacokinetic model simulating human plasma concentrations, FK037 showed potent bactericidal activity against H-MRSA in the plasma concentrations after intravenous infusion dosing with 1.0g. FK037 was synergistically active against H-MRSA in combination with either imipenem of fosfomycin. The in vitro post-antibiotic effect (PAE) of FK037 against H-MRSA ranged from 1.2 to 1.7 hours at one to four times the MIC.
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  • HIROSHI SAKAMOTO, KAZUO HATANO, YASUYUKI HIGASHI, YASUHIRO MINE, SHOJI ...
    1993 Volume 46 Issue 1 Pages 120-130
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Single-dose pharmacokinetics of FK037 has been investigated in laboratory animals. After bolus intravenous dosing with 20mg/kg, the elimination half-life of FK037 varied in the species; with values of 0.27, 0.30, 0.97, 1.29 and 1.76 hours in mice, rats, rabbits, dogs and monkeys, respectively. The volume of distribution ranged between 260 ml/kg in rats and 390 ml/kg in dogs. These parameters approximated those of ceftazidime and cefpirome used as reference drugs. The renal clearance of FK037 was almost equal to glomerular filtration rate (GFR) in rabbits. Probenecid did not affect the elimination half-life of FK037 and its clearance ratio to GFR. These findings suggest that FK037 is solely excreted by glomerular filtration. FK037 readily penetrated into the tissues and inflammatory exudate fluid in rats, and the tissue level was highest in the kidneys, and decreased in the following order; lungs>heart>liver>spleen. Penetration of FK037, cefpirome and ceftazidime into the cerebrospinal fluid were determined using induced staphylococcal meningitis in rabbits. The penetration percentage ranged from 14.2 to 16.0% for these drugs with no significant differences. The major route of excretion of FK037 was via the kidney, with more than 74% of the dose being excreted in the urine within 24 hours after dosing to each species. Biliary excretion was low, 0.79% in rats. Bioautograms showed only unchanged drug in the plasma, urine and bile. Serum protein binding was low (8.8 to 17.6%) in all the species studied.
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  • TOM S. CHEN, L. So, R. WHITE, R. L. MONAGHAN
    1993 Volume 46 Issue 1 Pages 131-134
    Published: January 25, 1993
    Released: April 19, 2006
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    The microbial metabolism of MK 954 (Fig. 1), a novel nonpeptide angiotensin II receptor antagonist, was investigated using 40 microorganisms in an initial screen for cultures that will produce metabolites similar to those produced in the mammalian liver. The microbial transformation occurred under aerobic conditions in shake flasks incubated at 27°C. Three metabolites of MK 954 were isolated and identified as the 1'-hydroxy M2, 3'-hydroxy M1 and glucuronic acid conjugated M3 derivatives. The structures of the metabolites were established by UV, 1H-NMR spectroscopy and FAB-MS spectrometry and are identical to metabolites produced by incubation of MK 954 with mammalian liver slices.
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  • MASAMI EZAKI, NOBUHARU SHIGEMATSU, MICHIO YAMASHITA, TADAAKI KOMORI, K ...
    1993 Volume 46 Issue 1 Pages 135-140
    Published: January 25, 1993
    Released: April 19, 2006
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    A precursor of biphenomycin A in mixed culture of Streptomyces griseorubiginosus No. 43708 with Pseudomonas maltophilia No. 1928 was isolated and characterized. The structure of the precursor, designated biphenomycin C was determined to be a peptide which is composed of biphenomycin A and arginylserine residue (Fig. 1), on the basis of chemical and spectroscopic evidence.
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  • HITOSI AGEMATU, Tosmo TSUCHIDA, KAICHIRO KOMINATO, NORIO SHIBAMOTO, TA ...
    1993 Volume 46 Issue 1 Pages 141-148
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Penicillin X methyl ester was transformed into three types of dimer by laccase from Coriolus versicohr. The dimers are considered to be formed by free-radical addition of phenoxy radicals produced by laccase. The enzyme reaction with the ester as substrate was more suitable for forming dimers than that with the sodium salt as substrate. Penicillin X pivaloyloxymethyl ester was also transformed into a dimer, which had antibacterial activity in the presence of esterase.
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  • I. LECTIN-MIMIC BINDING OF BMY-28864 TO YEAST MANNAN IN THE PRESENCE OF CALCIUM
    TOMOKAZU UEKI, KEI-ICHI NUMATA, YOSUKE SAW ADA, TASUKU NAKAJIMA, YASUO ...
    1993 Volume 46 Issue 1 Pages 149-161
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    BMY-28864 (BMS-181184), a water-soluble pradimicin derivative, specifically bound on the yeast cell surface in the presence of calcium, which was considered to be the initial step that triggered chain reactions leading to the fungicidal action. Close cause-effect relationships of the cell wall binding of BMY-28864 with its antifungal activity and potassium leakage induction were observed by Candida albicans and Saccharomyces cerevisiae in the presence and absence of calcium. Using mannan and methyl α-D-mannopyranoside as specific sugars, the mode of binding of BMY-28864 to sugar was examined in vitro in the presence of calcium. Quantitative component analysis revealed that the precipitate of BMY-28864 with methyl α-D-mannopyranoside and calcium was a ternary complex possessing a molar component ratio of 2.1:4.3:1.0. These findings altogether proved that BMY-28864, although not protein, recognized specific sugars such as mannose in the same manner as lectin, and that the ternary complex formation of BMY-28864 with specific sugar and calcium was the first step
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  • II. STRUCTURE DETERMINATION
    JAMES A. MATSON, KIMBERLY L. COLSON, GILBERT N. BELOFSKY, BONNIE B. BL ...
    1993 Volume 46 Issue 1 Pages 162-166
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The structure of sandramycin, a novel antitumor antibiotic, was established by spectroscopic analysis and chiral chromatography of its acid hydrolysate. It was determined to be a cyclic decadepsipeptide with a two-fold axis of symmetry and 3-hydroxyquinaldic acid as an appended chromophore.
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  • VANGA S. RAO, JOAN C. FUNG-TOMC, JAMES V. DESIDERIOM
    1993 Volume 46 Issue 1 Pages 167-176
    Published: January 25, 1993
    Released: April 19, 2006
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    Mono- and dipeptide derivatives of C4-β-aminoalkyl carbapenems were synthesized by the use of ammo acid N-carboxy anhydride for the peptide bond formation. They were shown to act as prodrugs in vivo while imparting the much desired chemical stability. The β-chloroalanyl derivative was suggested to act, in part, as a "dual-purpose" antibacterial.
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  • II. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF NEW 7β-[(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETAMIDO]-CEPHALOSPORINS WITH 1, 2, 3-TRIAZOLE IN C-3 SIDE CHAIN
    MASAHARU KUME, TADATOSHI KUBOTA, YASUO KIMURA, HIROMU NAKASHIMIZU, KIY ...
    1993 Volume 46 Issue 1 Pages 177-192
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The synthesis, antibacterial activity and oral absorbability of 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1H-1, 2, 3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid (1g) and related compounds are described. Their oral absorbability was influenced by the spacer length between C-3 of a cephem nucleus and C-4' of 1, 2, 3-triazole. The SCH2S structure was also found to contribute to their good oral absorption. The quantitative relationship between the bioavailability and the spacer length of cephalosporins (1a-1n) is discussed.
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  • MAKI NISHIO, MASAMI HASEGAWA, KIYOSHI SUZUKI, YOSUKE SAWADA, DEREK J. ...
    1993 Volume 46 Issue 1 Pages 193-195
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • MINORU TORIYA, SATOSHI YAGINUMA, SAKAE MUROFUSHI, KIYOSHI OGAWA, NAOKI ...
    1993 Volume 46 Issue 1 Pages 196-200
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • JAMAL MOUSLIM, ANNIE CUER, LUCIEN DAVID, J. C. TABET
    1993 Volume 46 Issue 1 Pages 201-203
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • A. A. TYMIAK, J. G. TUTTLE, S. D. KIMBALL, T. WANG, V. G. LEE
    1993 Volume 46 Issue 1 Pages 204-206
    Published: January 25, 1993
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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