The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 52, Issue 11
Displaying 1-14 of 14 articles from this issue
  • I. Screening Strategy and Validation
    ARMIN MAIER, CORINNA MAUL, MARION ZERLIN, ISABEL SATTLER, SUSANNE GRAB ...
    1999 Volume 52 Issue 11 Pages 945-951
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Chemical screening using thin-layer chromatography and various staining reagents offers the opportunity to visualize an almost complete picture of a microbial secondary metabolite pattern (metabolic finger-print). A thorough application of this strategy resulted in a number of biologically active new secondary metabolites, although the screening strategy is per se not correlated to any biological activity. In the present paper we report on a novel approach called biomolecular-chemical screening which combines the chemical screening strategy with binding studies of biological relevance. Making use of thin-layer chromatography (TLC) and subsequent staining, biomolecular-chemical screening allows to examine binding properties of low molecular weight metabolites to certain bio-macromolecules. The screening strategy itself, as well as independent validation of the results using DNA as selected bio-macromolecule are presented. The biomolecular-chemical screening method is useful to screen binding behaviour towards DNA of both, pure metabolites by one-dimensional TLC, and crude extracts by twodimensional TLC. Investigation of pure secondary metabolites as well as screening of crude microbial extracts and new secondary metabolites obtained with this screening strategy are presented in accompanying papers.
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  • II. Application Studies with Pure Metabolites
    ARMIN MAIER, CORINNA MAUL, MARION ZERLIN, SUSANNE GRABLEY, RALF THIERI ...
    1999 Volume 52 Issue 11 Pages 952-959
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    The novel screening strategy called "biomolecular-chemical screening" combines the advantages of the chemical screening approach-the analysis of the chromatographic and chemical behaviour of secondary metabolites on TLC plates-with binding studies of these molecules with bio-macromolecules like DNA. This approach was advantageously used to detect the interaction of pure compounds with DNA. In order to prove the reliability of the biomolecular-chemical screening and to examine DNA-binding properties, 470 pure secondary metabolites were analysed by this method. Besides the confirmation of already known binders with the TLC-based method, for a number of natural products DNA-binding properties were discovered for the first time. In consequence, binding of pure compounds can be measured by ID TLC in a reliable and easy manner, in which DNA is applied together with the test compound at the starting spot. Analysis is performed via differences in Rf-values in comparison to a reference chromatogram without DNA.
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  • HISAYOSHI AKAGAWA, YUKIE TAKANO, AYAKO ISHII, SATOSHI MIZUNO, REIKO IZ ...
    1999 Volume 52 Issue 11 Pages 960-970
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Stresgenin B was isolated as an inhibitor of heat-induced heat shock protein (HSP) gene expression from a culture broth of Streptomyces sp. AS-9 by silica gel chromatography and HPLC. The molecular formula of the novel compound was determined as C11H13NO5 by high resolution FAB-MS analysis, and the structure was determined by UV, 1H NMR, 13C NMR, HMQC, HMBC, and NOESY spectra. Stresgenin B inhibited heat-induced luciferase reportergene expression directed by the human hspTOB promoter in Chinese hamster ovary (CHO) cells at concentrations lower than the concentrations for inhibition of dexamethasone-induced luciferase reporter-gene expression directed by the mouse mammary tumor virus (MMTV)-LTR promoter. The inhibition of heat-induced reporter gene expression was evident even when cells were exposed to stresgenin B only during heat stress treatment. Moreover, the compound inhibited heat-induced syntheses of hsp72/73, hsp90, and hspllO and thereby suppressed the induction of thermotolerance. Stresgenin B showed moderate cytotoxic activities against several neoplastic cell lines and also showed antibacterial activities against Micrococcus luteus, Bacillus subtilis and Staphylococcus aureus strains.
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  • Taxonomy, Fermentation, Biological Properties, Isolation and Structure Elucidation
    HITOSHI TAKEUCHI, NAOKI ASAI, KAZUNORI TANABE, TERUYA KOZAKI, MASANORI ...
    1999 Volume 52 Issue 11 Pages 971-982
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    For the purpose of discovering novel agents that inhibit HIV-1 replication at the transcriptional level, we have established cell lines reflecting the HIV-1 long terminal repeatdriven gene expression. Using these cell lines, we have screened approximately 10, 000 microorganism products and found that the culture supernatant of Streptomyces sp. Mer-2487 suppresses the HIV-1 Tat-induced gene expression without affecting the basal or tumor necrosis factor-α-induced transcription. The purified active component has a unique structure, as shown in Fig. 1. This compound has an inhibitory effect on HIV-1 replication in chronically infected cells as well as acutely infected cells, suggesting that the inhibition occurs at a postintegration step of HIV-1 proviral DNA in the HIV-1 replication cycle.
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  • Taxonomy, Fermentation, Isolation, Physico-chemical Properties and Biological Activity
    CRISTINA ACEBAL, LIBRADA M. CAÑEDO, JOSÉ L. FERNÁ ...
    1999 Volume 52 Issue 11 Pages 983-987
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Agrochelin, a new alkaloid cytotoxic substance, was produced by the fermentation of Agrobacterium sp. The compound was obtained from the bacterial cells by solvent extraction and purified by silica gel chromatography. Agrochelin (1) and its acetyl derivative (2) exhibited cytotoxic activity.
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  • SIMON F. HINKLEY, JAMES C. FETTINGER, KIM DUDLEY, BRUCE B. JARVIS
    1999 Volume 52 Issue 11 Pages 988-997
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Four novel metabolites have been isolated from a rice culture of Memnoniella echinata (JS6308) by solvent extraction and radial silica chromatography. The structures were elucidated by spectroscopic techniques, and the absolute stereochemistry of memnobotrin A determined by X-ray crystallography.
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  • SANG-JUN LEE, BONG-SIKYUN YUN, DUCK-HYUN CHO, ICK-DONG YOO
    1999 Volume 52 Issue 11 Pages 998-1006
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Two new peptides, tylopeptins A and B, were isolated from the methanol extract of the fruiting body of the mushroom, Tylopilus neofelleus. These peptides were identified as peptaibols possessing an acetylated N-terminal residue, fourteen amino acids, and leucinol as the C-terminal amino alcohol. Sequential determination and complete 1H and 13C resonance assignments were based on positive ion FAB mass spectroscopy and two dimensional NMR techniques. These peptides were subsequently shown to be active against some Gram-positive bacteria, but inactive against pathogenic fungi and Gram-negative bacteria.
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  • LAURA J. L. NORCIA, ANNETTE M. SILVIA, JOHN P. DIRLAM, RODNEY C. SCHNU ...
    1999 Volume 52 Issue 11 Pages 1007-1016
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Two cyclic homopentapeptides, CP-101, 680 and CP-163, 234 [6a-(3', 4'-dichlorophenylamino) analogs of viomycin and capreomycin, respectively], were identified as novel antibacterial agents for the treatment of animal disease, especially for livestock respiratory disease. The in vitro microbiological characterization of both CP-101, 680 and CP-163, 234 was carried out using their parent compounds, viomycin and capreomycin, as controls. This characterization included antibacterial spectrum, influence of media, inoculum size, pH, EDTA, polymixin B nonapeptide (PMBN), serum, cell-free protein synthesis inhibition, and time-kill kinetics. Our results indicated that the capreomycin analog, CP-163, 234, showed slightly improved in vitro potency over the viomycin analog, CP-101, 680. Both analogs showed very potent cell-free protein synthesis inhibition activity and were bactericidal against Pasteurella haemolytica, P. multocida and Actinobacillus pleuropneumoniae at the level of 4 times and 8 times MICs. CP-163, 234 was bactericidal at the level of 4× and 8× MIC against E. coli, but re-growth was observed after 24 hours incubation at both concentrations of CP-101, 680.
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  • I. Taxonomy and Fermentation
    HIROSHI KANZAKI, DAISUKE IMURA, REIKO SASHIDA, AKIO KOBAYASHI, KAZUYOS ...
    1999 Volume 52 Issue 11 Pages 1017-1022
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Strain KO-23, an actinomycete producing albonoursin as well as streptopyrone, was identified as Streptomyces albulus by morphological and biochemical studies. Fermentation conditions for albonoursin, a dehydro cyclic dipeptide exhibiting a pronounced inhibitory activity toward pronuclear fusion of sea urchin eggs, were optimized. Under the optimum conditions, the actinomycete produced 16mg/liter of albonoursin, 30 times higher than that in the original culture. The cells cultivated under these conditions highly express biosynthetic enzymes for albonoursin, and thus are available for biosynthetic studies of dehydro cyclic peptides.
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  • M. G. ANDERSON, R. W. RICKARDS, E. LACEY
    1999 Volume 52 Issue 11 Pages 1023-1028
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Spectroscopic data define the structures of the flagranones A (2), B (3) and C (4) from the nematode-trapping fungus Duddingtonia flagrans. These antibiotics are structurally related to the farnesylated cyclohexenoxides of the oligosporon group recently isolated from the nematode-trapping fungus Arthrobotrys oligospora, and show similar antimicrobial activity.
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  • LOTHAR HEINISCH, ERNST ROEMER, PETER JÜTTEN, WOLFGANG HAAS, WALTE ...
    1999 Volume 52 Issue 11 Pages 1029-1041
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
    Madurahydroxylactone is a secondary metabolite from Nonomuria rubra (former Actinomadura rubra) with in vitro activity against Gram-positive bacteria and belongs to the family of benzo[a]naphthacenequinones. A series of derivatives of madurahydroxylactone were synthesized to investigate the effect on the antibacterial activity. Reaction with alcohols and amines gave cyclic acetals or aminals derived from the lactone form, whereas other amino reagents like hydroxylarnines and acyl or sulfonyl hydrazides led to the corresponding imine derivatives of the aldehyde. Hydrazine, alkyl and aryl hydrazines react with madurahydroxylactone under cyclization to give compounds of the new heterocyclic basic structure naphthaceno[1, 2-g]phthalazine. Some new compounds strongly inhibit Gram-positive bacteria, in part stronger than the parent compound.
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  • NORIKO TABATA, HIROSHI TOMODA, YUICHI YAMAGUCHI, ROKURO MASUMA, MARK J ...
    1999 Volume 52 Issue 11 Pages 1042-1045
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
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  • AKIRA ASAI, YOSHINORI YAMASHITA, KATSUHIKO ANDO, SHINGO KAKITA, KATSUN ...
    1999 Volume 52 Issue 11 Pages 1046-1049
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
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  • FERENC SZTARICSKAI, GYULA BATTA, ZOLTÁN DINYA, MIKLÓS HO ...
    1999 Volume 52 Issue 11 Pages 1050-1055
    Published: November 25, 1999
    Released on J-STAGE: September 19, 2008
    JOURNAL FREE ACCESS
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