The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 55 , Issue 1
Showing 1-18 articles out of 18 articles from the selected issue
  • YUKI UCHIHATA, NORITAKA ANDO, YOKO IKEDA, SHINICHI KONDO, MASA HAMADA, ...
    2002 Volume 55 Issue 1 Pages 1-5
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    The novel cyclic hexadepsipeptide named pipalamycin was isolated from a culture filtrate of Streptomyces sp. ML297-90F8 as an apoptosis-inducing agent. The antibiotic was found to be consisting of each one mole of alanine, N-hydroxyalanine, glycine, N-acylated 3-hydroxyleucine, and two moles of piperazic acid. Pipalamycin induced apoptosis in apoptosis-resistant human pancreatic adenocarcinoma AsPC-1 cells at 0.3μg/ml in 24-48 hours. It also showed antibacterial activity on Gram-positive bacteria such as Staphylococcus aureus and Micrococcus luteus. Fermentation, isolation, structural elucidation and the biological activities of pipalamycin are described.
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  • SHINICHI SAKEMI, JON BORDNER, DEBRA L. DECOSTA, KOEN A. DEKKER, HIDEO ...
    2002 Volume 55 Issue 1 Pages 6-18
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    CJ-15, 696 and 7 novel furopyridine antibiotics were isolated from the fungus Cladobotryum varium CL12284. Their structures were determined by X-ray crystallography and spectral analysis. Three biotransformed analogs were also prepared from CJ-15, 696. CJ-15, 696 showed moderate activity against various Gram-positive bacteria including some drug resistant strains such as methicillin resistant Staphylococcus aureus (MRSA).
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  • YUTAKA SUGIE, KOEN A. DEKKER, TAISUKE INAGAKI, YOON-JEONG KIM, TATSUO ...
    2002 Volume 55 Issue 1 Pages 19-24
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    A new antibiotic, CJ-17, 572 (I) was isolated from the fermentation broth of a fungus Pezicula sp. CL11877. The structure of I was determined to be a new equisetin derivative by spectroscopic analyses. The compound inhibits the growth of multi-drug resistant Staphylococcus aureus and Enterococcus faecalis with IC50s of 10 and 20μg/ml, respectively.
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  • YUTAKA SUGIE, SAE INAGAKI, YOSHINAO KATO, HIROYUKI NISHIDA, CHANG-HONG ...
    2002 Volume 55 Issue 1 Pages 25-29
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    A new equisetin derivative, CJ-21, 058 (I) was isolated from the fermentation broth of an unidentified fungus CL47745. It shows antibacterial activity against Gram-positive multi-drug resistant bacteria by inhibiting ATP-dependent translocation of precursor proteins across a bacterial cell membrane.
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  • MASATOSHI TANIGUCHI, KOJI NAGAI, MASATO WATANABE, NAMI NIIMURA, KEN-IC ...
    2002 Volume 55 Issue 1 Pages 30-35
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    A novel benz[a]anthraquinone, YM-181741, was isolated from the culture broth of actinomycete strain Q57219. The strain was identified as Streptomyces sp. by morphological and chemotaxonomic characterization. YM-181741 was purified from the culture supernatant by serial column chromatography. The structure of YM-181741 was determined by spectroscopic analysis including one- and two-dimensional NMR experiments. YM-181741 showed selective anti-Helicobacter pylori activity with a MIC value of 0.2μg/ml.
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  • 1. Production, Isolation and Biological Activities
    BÄRBEL KÖPCKE, MARTIN JOHANSSON, OLOV STERNER, HEIDRUN ANKE
    2002 Volume 55 Issue 1 Pages 36-40
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Eight secondary metabolites were isolated from submerged cultures of the ascomycete A111-95 during a search for new nematicidal metabolites. (-)-Galiellalactone (7) and compound 2 are metabolites previously obtained from cultures of Galiella rufa while the compounds 1, 3, 4, 5, 6 and 8 (3 and 4 were obtained as an unseparable mixture), were isolated as natural products for the first time. Compound 2, pregaliellalactone (5) and the mixture of 3 and 4 showed nematicidal activities towards Caenorhabditis elegans and Meloidogyne incognita. All compounds showed moderate or weak cytotoxic activities.
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  • Hydroxylation of Epo A and B to Epothilones E and F
    KLAUS GERTH, HEINRICH STEINMETZ, GERHARD HÖFLE, HANS REICHENBACH
    2002 Volume 55 Issue 1 Pages 41-45
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    When Sorangium cellulosum So ce90 is grown without XAD adsorber resin there is a steady state of epothilone A and B biosynthesis and hydroxylation of these products to epothilones E and F. This biotransformation at position C-21 of the thiazole ring is not restricted to producers of epothilones. It is carried out by a substrate induced monooxygenase. Epothilones E and F are further degraded by opening of the lactone ring by an esterase. Steps of degradation of different strains of S. cellulosum are compared.
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  • I. 13C-Labeling Experiments
    HIROSHI HORI, TAKAYUKI KAJIURA, YASUHIRO IGARASHI, TAMOTSU FURUMAI, KA ...
    2002 Volume 55 Issue 1 Pages 46-52
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Biosynthesis of hibarimicin was studied based on the feeding experiments with 13C labeled acetates. All carbons in the aglycon, except for the methoxy carbons, were derived from acetate. The carbon framework of the aglycon was proved to be constructed by dimerization of an intermediate which was biosynthesized via the decarboxylation and skeltal rearrangement starting from an undecaketide. The rearrangement was confirmed by detecting the long range (three-bond) coupling between two carbons in the difference spectra of selective 13C decoupled INADEQUATE of hibarimicin B labeled with sodium [1, 2-13C2] acetate.
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  • II. Elucidation of Biosynthetic Pathway by Cosynthesis Using Blocked Mutants
    TAKAYUKI KAJIURA, TAMOTSU FURUMAI, YASUHIRO IGARASHI, HIROSHI HORI, KA ...
    2002 Volume 55 Issue 1 Pages 53-60
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    The biosynthetic pathway of hibarimicin (HBM) was proposed on the basis of the experimental results obtained by using blocked mutants of Microbispora rosea subsp. hibaria TP-A0121, the HBM producer. In its biosynthesis, the oxidative coupling of the aromatic undecaketide unit generates a symmetrical aglycon HMP-Y1 (hibarimicin-mutant product Y1), which is oxidatively modified to hibarimicinone, the HBM aglycon. The following glycosylation of hibarimicinone gives rise to the HBM complex. We identified that HMP-Y1 prepared by methanolysis of HMP-Y6, a glycosylated metabolite from a blocked mutant, was the key intermediate: transformation of 13C-labeled HMP-Y1 to HBM B was confirmed by NMR measurements. Mutant strain produced another type of aglycon HMP-P1 in which the coupled polyketide units were intramolecularly bridged by the ether bond. This metabolite also arose by the spontaneous elimination of methanol molecule from hibarimicinone.
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  • III. Structures of New Hibarimicin-related Metabolites Produced by Blocked Mutants
    YASUHIRO IGARASHI, TAKAYUKI KAJIURA, TAMOTSU FURUMAI, HIROSHI HORI, KA ...
    2002 Volume 55 Issue 1 Pages 61-70
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Structures of metabolites produced by blocked mutants of Microbispora rosea subsp. hibaria TP-A0121, hibarimicin-producer, were determined by spectroscopic analysis. HMP-Y6 is the dimer of the west half of hibarimicin B, the aglycon of which is the genuine biosynthetic intermediate. HMP-P1 is the shunt product arising from the release of a methanol molecule from hibarimicinone. HMP-P4, the glycoside of HMP-P1, is glycosylated with two amicetoses and two digitoxoses same as hibarimicin B. HMP-M1, M2, M3 and M4 are shunt products derived from the monomeric undecaketide intermediates.
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  • III. Immunosuppressive Efficacy
    KAZUHIKO KUROSAWA, KOSAKU TAKAHASHI, NOBUAKI FUJISE, YASUSHI YAMASHITA ...
    2002 Volume 55 Issue 1 Pages 71-77
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Novel immunosuppressants, SNF4435C and D produced by a strain of Streptomyces spectabilis, were examined for their pharmacodynamical profiles. SNF4435C and D suppressed the responses of both murine splenocytes and human peripheral blood lymphocytes in the mixed lymphocyte reaction (MLR) with IC50 values of 0.5μM and 0.2μM, respectively. In the mouse MLR experiments, SNF4435C and D did not block the production of interleukin-2 (IL-2) and the compounds-induced suppression was not restored by the addition of exogeneous IL-2. In addition, the significant inhibitory action was still retained even when SNF4435C or D was added after 48 hours from the start of the culture. These results were distinct from the behaviors observed with FK-506. SNF4435C, the major component, suppressed mouse delayed type hypersensitivity (DTH) and prolonged rat skin allograft survival.
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  • YUKIO KOIZUMI, KEIJI HASUMI
    2002 Volume 55 Issue 1 Pages 78-82
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    We have found that malformin A1, a cyclopentapeptide metabolite of Aspergillus niger, enhanced 2.0-to 3.2-fold the 125I-fibrin clot lysis when incubated at 1-10μM with both U937 cells and blood plasma, both of which were essential to the malformin A1 action. The effect was inhibited by ε-aminocaproic acid and anti-urokinase serum, but not by anti-tissue-type plasminogen activator IgG, showing that the enhancement was mediated by urokinase-catalyzed plasminogen activation. However, malformin A1 affected neither cellular urokinase activity nor cell-free reactions involved in the fibrinolytic pathway. Malformin-treated, washed cell had an increased capacity to degrade fibrin in the presence of plasma. These results suggest that malformin A1 enhances fibrinolytic activity by affecting cell-mediated response to initiate and/or propagate fibrinolytic activity.
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  • SHIGEKI OHYAMA, YASUKO WADA, KEIJI HASUMI
    2002 Volume 55 Issue 1 Pages 83-91
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Three thiopeptide metabolites that enhance fibrin binding of plasminogen were isolated from a culture of Streptomyces sp. R1401. A combination of spectroscopic analyses revealed that these compounds were identical with the antibiotic A10255B, E and G. These agents enhanced fibrin binding of plasminogen and plasminogen/urokinase-mediated fibirinolysis at concentrations of 5-20μM. A10255B reversibily increased urokinase-catalyzed activation of plasminogen by lowering Km, while the agent did not enhance urokinase activity when substrates other than plasminogen were used, indicating that the agent affects plasminogen to increase its affinity to urokinase. A smaller but significant increase in activation was also observed when conformationally relaxed plasminogen derivatives such as Lys-plasminogen and mini-plasminogen were used. Two related thiopeptide antibiotics with a C-terminal amide had no effect on plasminogen activation, suggesting a role of the terminal carboxyl of the A10255 molecule in activity.
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  • HAYAMITSU ADACHI, YOSHIO NISHIMURA, TOMIO TAKEUCHI
    2002 Volume 55 Issue 1 Pages 92-98
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Some derivatives of bactobolin were prepared from bactobolin (1) by transformation of the dichloromethyl group at C-3 to the hydroxymethyl, carboxylic acid, methanesulfonyloxymethyl and aldehydeoxime groups. The derivatives proved to be less active than the parent antibiotic 1 against bacteria as well as cytotoxicity, indicating that the functionality at C-3 considerably influences the biological activity.
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  • KEITA KONO, MASAKO SUGIURA, TAKAFUMI KOHAMA
    2002 Volume 55 Issue 1 Pages 99-103
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
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  • 2. Structure Elucidation
    MARTIN JOHANSSON, BÄRBEL KÖPCKE, HEIDRUN ANKE, OLOV STERNER
    2002 Volume 55 Issue 1 Pages 104-106
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
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  • SAYRA KHATUN, ALASTAIR C. W. WAUGH, MARIA B. REDPATH, PAUL F. LONG
    2002 Volume 55 Issue 1 Pages 107-108
    Published: January 25, 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
    Download PDF (325K)
  • 2002 Volume 55 Issue 1 Pages C1
    Published: 2002
    Released: January 27, 2009
    JOURNALS FREE ACCESS
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