The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 49 , Issue 2
Showing 1-17 articles out of 17 articles from the selected issue
  • SIOBHAN STEVENS-MILES, MICHAEL A. GOETZ, GERALD F. BILLS, ROBERT A. GI ...
    1996 Volume 49 Issue 2 Pages 119-123
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Cytosporin A, B and C, three antagonists of [125I]-angiotensin II binding to rat adrenal glands were discovered in fermentations of an endophytic Cytospora sp. during routine screening using semi-automated procedures. The most potent of these displayed an IC50 of 1.5-3 μM and was specific for angiotensin II AT2.
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  • GREGORY M. BRILL, USHA PREMACHANDRAN, JAMES P. KARWOWSKI, RODGER HENRY ...
    1996 Volume 49 Issue 2 Pages 124-128
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    The novel calcineurin inhibitor, dibefurin, has been isolated from the fungal culture AB 16501-759. The isolation was bioactivity-directed fractionation using an assay which measures the phosphatase activity of calcineurin. The compound was purified by countercurrent, reverse phase and gel filtration chromatographics. Several studies, including crystallographic, NMR and MS, revealed that dibefurin is a novel dimeric compound of a unique structural type.
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  • Taxonomy, Fermentation, Isolation, Structure Elucidation and Biological Activity
    YOSHIO KAJIMURA, MIYUKI KANEDA
    1996 Volume 49 Issue 2 Pages 129-135
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Fusaricidin A, a new depsipeptide antibiotic, was isolated from the culture broth of Bacillus polymyxa KT-8 obtained from the rhizosphere of garlic suffering from the basal rot caused by Fusarium oxysporum. The structure of fusaricidin A was determined by ID and 2D NMR and MS experiments coupled with amino acid analysis to be a hexadepsipeptide containing 15-guanidino-3-hydroxypentadecanoic acid as a side chain. The absolute configuration of each amino acid residue was determined by chiral HPLC. Fusaricidin A is active against fungi and Gram-positive bacteria.
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  • I. Taxonomy, Fermentation, Isolation and Biological Properties
    KAZUMA KAMIGIRI, YASUTO SUZUKI, MITSUYOSHI SHIBAZAKI, MOTOO MORIOKA, K ...
    1996 Volume 49 Issue 2 Pages 136-139
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Novel antibacterial antibiotics, kalimantacins A, B and C, have been isolated from the fermentation broth of Alcaligenes sp. YL-02632S. In this paper, the taxonomy of the producing strain, fermentation, isolation and biological activities of kalimantacins are reported. Kalimantacins inhibit the growth of Staphylococcus aureus and S. epidermidis including multiple-drug resistant strains.
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  • II. Physico-chemical Properties and Structure Elucidation
    TATSUHIRO TOKUNAGA, KAZUMA KAMIGIRI, MASAYA ORITA, TOSHIAKI NISHIKAWA, ...
    1996 Volume 49 Issue 2 Pages 140-144
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Kalimantacin A, B and C are new antibiotics produced by Alcaligenes sp. YL-02632S. Their structures were elucidated to be novel long chain structure compounds containing O-carbamoyl, amide and carboxylic acid moieties based on various 2D NMR experiments and MS analysis.
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  • I. Taxonomy, Isolation and Characterization
    E. SELVA, L. GASTALDO, G. S. SADDLER, G. TOPPO, P. FERRARI, G. CARNITI ...
    1996 Volume 49 Issue 2 Pages 145-149
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Novel cyclic peptide antibiotics A21459 A and B are produced by a member of the genus Actinoplanes sp. These antibiotics inhibit bacterial protein synthesis and have selective antimicrobial activity against clostridia, mycoplasma and some Gram-negative bacteria.
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  • II. Structure Elucidation
    P. FERRARI, K. VÉKEY, M. GALIMBERTI, G. G. GALLO, E. SELVA, L. ...
    1996 Volume 49 Issue 2 Pages 150-154
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    The structures of the antibiotics, active against a few Gram-negative bacteria and Clostridium difficile, were determined on the basis of physicochemical analyses on the intact molecules and on the acid hydrolysate of A21459 A. FAB-MS and 1H and 13C NMR investigations identified the amino acid units and determined their sequence.
    Antibiotics A21459 A and B are homodetic cyclic peptides constituted by eight amino acid units. They are glycine, methoxytryptophan, tryptophan, cysteine, alanine, sarcosine, dehydroalanine, and α-aminobutyric acid for A21459 A (alanine for A21459 B). Cysteine and alanine condensed to form a thiazole moiety, according to the biosynthesis of thiazole containing antibiotics.
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  • TSUTOMU TSURUOKA, HARUMI FUKUYASU, MIYUKI ISHII, TAKAYUKI USUI, SEIJI ...
    1996 Volume 49 Issue 2 Pages 155-161
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    The antimetastatic activity often compounds structurally related to nojirimycin A was examined using a pulmonary metastatic model of mouse B16 melanoma. Nojirimycin B, deoxynojirimycin, D-gluco-δ-lactam, CP3068 and CP3069 are structural analogues of nojirimycin A, and showed potent or moderate antimetastatic activities. Nojirimycin A, nojirimycin B, deoxynojirimycin and D-gluco-δ-lactam showed potent or moderate inhibitory activities against α-glucosidase, β-glucosidase and β-mannosidase, but CP3068 and CP3069 in which the structures were related to D-gluco-δ-lactam showed no inhibitory activities. CP3041, CP3042, CP3043, CP3045 and CP3048 are analogues of sodium D-glucaro-δ-lactam (ND2001), a carboxy derivative of nojirimycin A, and showed potent or moderate antimetastatic activities. But no analogue was superior to ND2001 concerning with antimetastatic and anti-β-glucuronidase activities. CP3041 and CP3042 showed potent and moderate inhibitory activities against β-glucuronidase, respectively, but CP3043, CP3045 and CP3048 showed little or no activities.
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  • HERBERT A. KIRST, JON S. MYNDERSE, JAMES W. MARTIN, PATRICK J. BAKER, ...
    1996 Volume 49 Issue 2 Pages 162-167
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Ossamycin is a cytotoxic agent of undetermined structure that was originally isolated in 1965 from culture broths of Streptomyces hygroscopicus var. ossamyceticus. Its overall structure and relative stereochemistry have now been determined by single crystal X-ray diffraction studies. Absolute stereochemistry was established according to the previously determined configuration of its aminosaccharide constituent, ossamine. The aglycone of ossamycin possesses a 24-membered macrolide ring system onto which is incorporated both a 6, 6-spiroketal and a 5-membered hemiketal ring system. The overall three-dimensional structure possesses features in common with the related macrocyclic antibiotics dunaimycin, cytovaricin, and A82548A.
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  • III. Biochemical Properties of RES-1149-1, -2 and Structure-activity Relationships
    TATSUHIRO OGAWA, YOUICHI UOSAKI, TAKEO TANAKA, EUI TSUKUDA, AKIRA MIHA ...
    1996 Volume 49 Issue 2 Pages 168-172
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    RES-1149-1 and -2, produced by Aspergillus sp. RE-1149, were found to be non-peptidic antagonists for endothelin type B receptor (ETB receptor). RES-1149-1 and -2 selectively inhibited the endothelin-1 (ET-1) binding to ETB receptor in a competitive manner with IC50 values of 1.5 μM and 20 μM, respectively. RES-1149-1 inhibited the increase in intracellular Ca2+ concentration elicited by 1 nM ET-1 in COS-7 cells expressing human ETB receptor, but not in the case of cells expressing ETA receptor. In addition, some structure-activity relationships are described.
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  • KEN YASUI, YOSHINORI TAMURA, TAKUJI NAKATANI, ISAO HORIBE, KENJI KAWAD ...
    1996 Volume 49 Issue 2 Pages 173-180
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    5β-Methoxy (20), 14-methyl (24), 14, 14-dibromo-15-nor (25), 8-O-acyl (26-45), 8-O-alkyl (46), 8-O-alkoxycarbonyl (47, 48), and 8-O-carbamoyl (49) derivatives of PA-48153C, a novel immunosuppressant isolated from fermentation products of Streptomyces prunicolor PA-48153, were prepared. These compounds were found to retain the inhibitory activity on the responses of both T arid B cells to mitogens. Among them, the C-8 hexanoate 28 showed potent suppressive effects on mitogen responses with less cytotoxicity to EL4 cells and was selected for in vivo evaluation.
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  • HELEN LINSDELL, CATHERINE TOIRON, MARTA BRUIX, GERMÁN RIVAS, MA ...
    1996 Volume 49 Issue 2 Pages 181-193
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    The thermodynamics of glycopeptide antibiotic dimerization have been studied by means of sedimentation equilibrium, using A82846B, vancomycin, ristocetin and complexes formed with several cell wall model pep tides. These results indicate that vancomycin dimerization can be strongly promoted in two ways: i) stabilization of the antibiotic conformation in which the carbonyl group of residue three is on the back face of the molecule and ii) preferential interaction of the dimer with the lysine residue of N, N'-diacetyl-lysyl-D-alanyl-D-alanine. This effect was not found in ristocetin. A82846B forms stable dimers at very low antibiotic concentration. Two conformational forms have been found for complexed A82846B by 1H NMR. However, calorimetric binding experiments have shown that all its binding sites are thermodynamically equivalent. The affinity of the A82846B dimer for the tripeptide has been estimated to be about SkJ • mol-1 higher than that of the vancomycin monomer and about -2.6kJ•mol-1 lower than that of dimeric vancomycin. The possible role of dimerization in the biological activity of glycopeptide antibiotics1) is discussed further on the basis of present thermodynamic data.
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  • A. Y. PAVLOV, T. F. BERDNIKOVA, E. N. OLSUFYEVA, O. V. MIROSHNIKOVA, S ...
    1996 Volume 49 Issue 2 Pages 194-198
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    Carboxamides and hydrazide of glycopeptide antibiotic eremomycin were obtained by a direct reaction of the carboxy group of eremomycin with an appropriate amine or hydrazine using diphenyl phosphorazidate as a condencing agent. Eremomycin hydrazide was also obtained by hydrazinolysis of the eremomycin methyl ester. Use of dicyclohexylcarbodiimide or 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide for amidation led to the corresponding eremomycin ureides. The ESI-MS data indicate that eremomycin and its amides exist as dimers. The carboxamide, methylamide and benzylamide of eremomycin were as active against Gram-positive bacteria as the parent antibiotic, and the methylamide, benzylamide and hydrazide were almost an order of magnitude more active than eremomycin against Staphylococcus epidermidis clinical isolates in vitro. Amide of eremomycin as well as ureides were devoid of histamine liberating properties, which demonstrates that protection of the carboxyl group leads to a decrease in the allergenic properties.
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  • Synthesis and Structure-activity Relationships of 2-(5-Substituted Pyrrolidin-3-ylthio)-1β-methylcarbapenenis
    YASUYOSHI Iso, TADASHI IRIE, YUTAKA NISHINO, KIYOSHI MOTOKAWA, YASUHIR ...
    1996 Volume 49 Issue 2 Pages 199-209
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
    The synthesis and biological activity of (1R, 5S, 6S)-2-[(3S, 5S)-5-substituted pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acids are described. These compounds exhibit potent antibacterial activity against a wide range of both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. Of these new carbapenems, (1R, 5S, 6S)-2-[(3S, 5S)-5-sulfamoylaminomethyl pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (S-4661) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.
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  • Isolation and Structure Elucidation of a New Cyclopentenone Derivative (3-Dimethylamino-5-hydroxy-5-vinyl-2-cyclopenten-l-one)
    TRIPTIKUMAR MUKHOPADHYAY, KIRITY ROY, S. N. SAWANT, SUNIL K. DESHMUKH, ...
    1996 Volume 49 Issue 2 Pages 210-211
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
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  • C. FIAKPUI, G. THOMAS, M. P. SINGH, R. G. MICETICH, R. SINGH
    1996 Volume 49 Issue 2 Pages 212-215
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
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  • CHENG-BIN CUI, MAKOTO USUKATA, HIDEAKI KAKEYA, RIE ONOSE, GEN OKADA, I ...
    1996 Volume 49 Issue 2 Pages 216-219
    Published: February 25, 1996
    Released: November 21, 2006
    JOURNALS FREE ACCESS
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