The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 44 , Issue 2
Showing 1-21 articles out of 21 articles from the selected issue
  • SHINICHI KONDO, SHUICHI GOMI, KAZUMICHI UOTANI, SHIGEHARU INOUYE, TOMI ...
    1991 Volume 44 Issue 2 Pages 123-129
    Published: February 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Four minor benanomicins, dexylosylbenanomicins A and B, 2'-demethylbenanomicin A and 7-methoxybenanomicinone have been isolated from the culture filtrate of Actinomadura sp. MH193-16F4. Their structures were confirmed by spectral analyses. Dexylosylbenanomicins A and B were derived chemically from benanomicins A and B, respectively.
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  • MOTOAKI NISHIKAWA, YASUHISA TSURUMI, HIDETSUGU MURAI, KEIZO YOSHIDA, M ...
    1991 Volume 44 Issue 2 Pages 130-135
    Published: February 25, 1991
    Released: April 19, 2006
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    WF-2421 is a novel aldose reductase inhibitor produced by Humicola grisea. WF-2421 was purified from the culture filtrate by successive ion exchange chromatography and the chemical structure was assigned to be α-formamido-5'-(2-formamido-l-hydroxyethyl)-β, 2', 6-trihydroxy-3-biphenylpropanoic acid (1) on the basis of spectroscopic evidence.
    The IC50 value of WF-2421 was 3 × 10-8 M against partially purified aldose reductase of rabbit lens.
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  • HIROSHI TOMODA, HIROYUKI NISHIDA, ROKURO MASUMA, JING CAO, SHIGENOBU O ...
    1991 Volume 44 Issue 2 Pages 136-143
    Published: June 25, 1991
    Released: April 19, 2006
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    Penicillium purpurogenum FO-608, a soil isolate, was found to produce a series of new inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). Three active compounds, designated purpactins A, B and C, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography and HPLC. Purpactins inhibit ACAT activity in an enzyme assay system using rat liver microsomes with IC50 values of 121-126 μM. Purpactin A also inhibited cholesterol ester formation in J 774 macrophages, indicating the inhibition of ACAT activity in the living cells by purpactin A.
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  • HIROYUKI NISHIDA, HIROSHI TOMODA, JING CAO, SHIGENOBU OKUDA, SATOSHI O ...
    1991 Volume 44 Issue 2 Pages 144-151
    Published: February 25, 1991
    Released: April 19, 2006
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    The structure of purpactins, novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors, was determined by spectroscopic analyses. Purpactin A was deduced to be 3-l'-acetoxy-11-hydroxy-4- methoxy-9-methyl-3'-methylbutyl-5H, 7H-dibenzo[b, g]-l, 5-dioxocin-5-one, purpactin B was 5-1"- acetoxy-6'-hydroxyrnethyl-4-methoxy-4'-methyl-3"-methylbutyl-spiro[benzofuran-2, r-cyclohex a- 3', 5'-diene]-2', 3(2H)-dione and purpactin C was 5-l"-acetoxy-6'-formyl-4-methoxy-4'-methyl-3"- methylbutyl-spiro[benzofuran-2, 1'-cyclohexa-3', 5'-diene]-2', 3(2H)-dione. Purpactin A was attributed to 1'-O-acetylpenicillide.
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  • HIROYUKI NISHIDA, HIROSHI TOMODA, JING CAO, SACHIKO ARAKI, SHIGENOBU O ...
    1991 Volume 44 Issue 2 Pages 152-159
    Published: February 25, 1991
    Released: April 19, 2006
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    Acylated drivatives of the C-1' and/or C-11 hydroxy group(s) of penicillide were synthesized and their inhibitory activity against acyl-CoA:cholesterol acyltransferase (ACAT) was studied. Introduction of long acyl group into either or both hydroxy residue(s) decreased the inhibitory activity. A small acyl moiety such as acetyl or n-butyryl at the C-1' hydroxy group is responsible for potent inhibitory activity against ACAT. The 1'-O-acetyl-11-O-tetrahydropyranyl derivative (11-O-2"-tetrahydropyranylpurpactin A) showed high selectivity (cytotoxic dose vs. effective dose) in a cell assay using J774 macrophages.
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  • DAMICHI SONODA, HIROYUKI OSADA, Jun UZAWA, KIYOSHI ISONO
    1991 Volume 44 Issue 2 Pages 160-163
    Published: February 25, 1991
    Released: April 19, 2006
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    A new glutarimide antibiotic named actiketal was isolated from the culture fluid of the epiderstatin-producing streptomycete, Streptomyces pulveraceus subsp. epiderstagenes. The IC50 of the antibiotic for inhibition of the incorporation of [3H]thymidine into epidermal growth factor-stimulated Balb/MK cells was 14.5 μM. The structure of this compound was determined by 1H and 13C NMR spectroscopic analyses using 1H-1H COSY, 13C-1H COSY, heteronuclear multiple-bond correlation spectroscopy, selective 13C-{1H} NOE's techniques.
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  • W. WEBER, W. FISCHLI, E. HOCHULI, E. KUPFER, E. K. WEIBEL
    1991 Volume 44 Issue 2 Pages 164-171
    Published: February 25, 1991
    Released: April 19, 2006
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    Anantin, a peptide binding to the receptor of the atrial natriuretic factor (ANF) was isolated from a strain of Streptomyces coerulescens. The molecule consists of 17 natural L-amino acids which form a peptidic ring system. It has a MW of 1, 871.0. The chemical composition is C90H111 N21O24.
    The compound was found to bind competitively to ANF-receptors from bovine adrenal cortex (Kd = 0.61 μM). Furthermore, it dose-dependently inhibited the ANF-induced intracellular cyclic guanosine monophosphate accumulation in bovine aorta smooth muscle cells. At the same concentration no agonistic effects were detectable in these cells. Thus, anantin is considered to be the first microbially produced antagonist of the cardiac hormone, ANF.
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  • D. F. WYSS, H.-W. LAHM, M. MANNEBERG, A. M. LABHARDT
    1991 Volume 44 Issue 2 Pages 172-180
    Published: February 25, 1991
    Released: April 19, 2006
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    Anantin, a naturally occurring peptide from Streptomyces coerulescens, binds competitively to the receptor of atrial natriuretic factor (ANF) from bovine adrenal cortex (Kd=0.6 μM) and acts as ANF antagonist. Protein chemical data and FAB-MS have identified anantin to be a cyclic polypeptide consisting of 17 common L-amino acids. The molecule is highly stable and precludes the application of standard sequencing methods. The primary sequence of anantin was determined by 2D 1H NMR spectroscopy and the application of advanced protein chemical methods to be Gly1-Phe2-Ile3-Gly4-Trp5-Gly6-Asn7-Asp8-Ile9-Phe10-Gly11-His12-Tyr13-Ser14-Gly15-Asp16-Phe17. The molecule is cyclized between the β-carboxyl group of Asp8 and the amino group of Gly1.
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  • HIROSHI HIROTA, AKIRA ITOH, JUNKO IDO, YUKIMASA IWAMOTO, EIICHI GOSHIM ...
    1991 Volume 44 Issue 2 Pages 181-186
    Published: February 25, 1991
    Released: April 19, 2006
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    The planar structure of a new polyene macrolide antibiotic, YS-822A, which was isolated from the culture filtrate of a mutant strain H-8 of Streptoverticillium eurocidicum var. asterocidicus S-822, was established as I on the basis of spectroscopic evidences and by comparison of spectroscopic data with nystatin A1 (II) and amphotericin A (III), representative polyene macrolide antibiotics. Molecular formula of YS-822A was established as C37H59NO14 (MW 741) by elemental analysis, NMR, and FAB mass spectra. The UV spectrum of YS-822A was very similar to that of nystatin A1, suggesting that YS-822A also has a conjugated all-trans-tetraene moiety. 1H and 13C NMR spectra of YS-822A showed a number of broad and overlapped signals, but the 1H-1H and 13C-1H COSY spectra implied the existence of a mycosamine moiety and several other partial structures. The connectivity of these partial structures was established by extensive 2D NMR experiments, including homonuclear Hartmann-Hahn and heteronuclear multiple-bond connectivity measurements, which led to the determination of the gross planar structure of YS-822A as I.
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  • HARTMUT LAATSCH, MICHAEL KELLNER, HORST WEYLAND
    1991 Volume 44 Issue 2 Pages 187-191
    Published: February 25, 1991
    Released: April 19, 2006
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    A red pigment produced by the actinomycete strain B 4358 was identified as butyl-meta-cycloheptylprodiginine (4) by 1H, 13C and correlation via long range coupling NMR spectra. It shows striking spectroscopic similarities to butyl-ortho-cycloheptylprodiginine (1), the structure of which needs to be revised.
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  • M. N. PREOBRAZHENSKAYA, E. V. BAKINA, L. S. POVAROV, E. I. LAZHKO, L. ...
    1991 Volume 44 Issue 2 Pages 192-199
    Published: February 25, 1991
    Released: April 19, 2006
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    A series of phenylthiourea and ethylthiourea derivatives of daunorubicin and its congeners was prepared by reaction of the 3'-amino group of the antibiotic with phenylisothiocyanate or ethylisothiocyanate. S-Methylation yielded S-methylisothiouronium salts which when reacted with amines resulted in an intramolecular cyclization with the participation of the neighboring 4'-OH group. The structures and predominant conformations of the thiourea derivatives and daunorubicino(3'-N, 4'-O-d)oxazolines were determined by 1H and 13C NMR. Cytostatic activities of the thiourea and oxazoline derivatives were compared with the cytostatic activities of N-methylurea and N-methyl-N-nitrosourea containing daunorubicin and its congeners. Carminomycin derivatives were endowed with the highest cytostatic activity.
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  • THOMAS P. DEMUTH, RONALD E. WHITE, RUTH A. TIETJEN, RONALD J. STORRIN, ...
    1991 Volume 44 Issue 2 Pages 200-209
    Published: February 25, 1991
    Released: April 19, 2006
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    A series of cephalosporins derived from cephalothin containing an ester-linked quinolonyl substituent at the C-10 position (C-10 quinolonyl-cephem esters) has been prepared and evaluated for in vitro antibacterial activity. The C-10 quinolonyl-cephem esters exhibited a broadened spectrum of activity when compared with cephalothin and the corresponding quinolones, including activity against β-lactamase-producing bacteria.
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  • D. R. KIRSCH, M. H. LAI, J. MCCULLOUGH, A. M. GILLUM
    1991 Volume 44 Issue 2 Pages 210-217
    Published: February 25, 1991
    Released: April 19, 2006
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    The desirable features for a screening assay to detect antibacterial antibiotics include 1) high specificity for the desired antibiotic type 2) high sensitivity 3) lack of interference by other compounds likely to be associated with the antibiotic of interest and 4) ease of operation to allow a large number of samples to be tested. These characteristics are largely found in screens employing strains carrying fusions between antibiotic induced promoters and the structural genes for Escherichia coli β-galactosidase. Screens were designed based upon fusions with three antibiotic induced promoters: the tetracycline induced tetA/tetR promoter from transposon Tn10, the erythromycin induced promoter from the Staphylococcus aureus ermC erythromycin-resistance gene and the chloramphenicol induced promoter from the S. aureus cat86 chloramphenicol-resistance gene. Because there have been no reports of vancomycin induced resistance determinants, a Tn903 random gene fusion pool was screened to isolate a vancomycin induced gene fusion. This gene fusion was induced fairly specifically by glycopeptide antibiotics and the fusion was used as the basis for a glycopeptide screen.
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  • ANDREW L. STALEY, KENNETH L. RINEHART
    1991 Volume 44 Issue 2 Pages 218-224
    Published: February 25, 1991
    Released: April 19, 2006
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    [Carboxy-]sp14C]-3-amino-5-hydroxybenzoic acid (AHBA) has been shown to be incorporated by Streptomyces spectabilis to the extent of greater than 0.1% (35:1 dilution) in the ansamycin antibiotic streptovaricin C, the major component of the streptovaricin complex. When [carboxy-13C]AHRA was similarly administered, C-21 (quinone methide carbonyl at 188.3 ppm) of streptovaricin C was specifically labeled (at twenty one times natural abundance). In preparation for the 13C incorporation study the 13C NMR spectrum of streptovaricin C was investigated, making extensive use of short- and long-range HETCOR. These assignments revise some of those proposed earlier for streptovaricin C.
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  • CHRISTOPHER M. M. FRANCO, URMILA P. BORDE, E. K. S. VIJAYAKUMAR, SUGAT ...
    1991 Volume 44 Issue 2 Pages 225-231
    Published: February 25, 1991
    Released: April 19, 2006
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    Butalactin, [2-(4', 5'-epoxy-hex-2'(E)-en)oyl-2-hydroxy-3-hydroxymethyl-2, 3-(Z)-butanolide] is a new antibiotic produced by Streptomyces sp. HIL Y-86, 36923. Taxonomically, the producing organism most closely resembles Streptomyces corchorusii. The strain also produces cineromycin B. Though butalactin is structurally related to 'signal molecules' such as A-factor, the anthracycline inducing factors and the virginiae butanolides, it does not show inducing activity for antibiotic production or aerial mycelium formation in the indicator strain. Butalactin possesses a weak antibiotic activity against Gram-positive and Gram-negative bacteria.
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  • KEIKO NAKAGAWA, SHUNICHI MIYAKOSHI, AKIO TORIKATA, KAZUO SATO, YOSHIHI ...
    1991 Volume 44 Issue 2 Pages 232-240
    Published: February 25, 1991
    Released: April 19, 2006
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    Many strains of zygomycetes and actinomycetes were found to convert milbemycin A4 (1a) to 13β-hydroxymilbemycin A4 (1b). Among these strains, Cunninghamella echinulata ATCC 9244 had the most efficient 13β-hydroxylation ability on milbemycins. In the conversion of milbemycin A3 (2a), 29-hydroxymilbemycin A4 (4a), and 30-hydroxymilbemycin A4 (5a) with this strain, only 13 β-hydroxylated products were obtained. On the other hand, starting from milbemycin A4 (1a) and 5-ketomilbemycin A4 5-oxime (6a), 13β, 24- and 13β, 30-dihydroxy derivatives were also isolated along with 13β-hydroxylated products. Similarly, conversion of milbemycin D (3a) and LL-F28249α (8a) gave 13β- and 28-hydroxy derivatives (8b and 8c).
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  • JACK E. BALDWIN, JULIETTE W. BIRD, ROBERT A. FIELD, NIAMH M. O'CALLAGH ...
    1991 Volume 44 Issue 2 Pages 241-248
    Published: February 25, 1991
    Released: April 19, 2006
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    δ-(L-α-Aminoadipoyl)-L-cysteinyl-D-valine (ACV) synthetase was isolated and partially characterised from Cephalosporium acremonium CO728 and Streptomyces clavuligerus. The purification procedure resulted in a 745- and 277-fold increase in specific enzyme activity, respectively. Both enzymes had similar apparent molecular masses of ca. 300 kdaltons by SDS-polyacrylamide electrophoresis, under reducing and denaturing conditions, and in excess of 600 kdaltons in the native state by gel filtration. Attempts to obtain an N-terminal amino acid sequence of ACV synthetase from C. acremonium were unsuccessful, hence internal amino acid sequence data were obtained after tryptic digestion of the protein. Phosphopantothenic acid was shown to be associated with the enzyme from both sources, which suggests the possible involvement of pantothenate as a 'swinging arm' in the formation of the tripeptide ACV.
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  • OTTO D. HENSENS, ROBERT P. BORRIS, LAWRENCE R. KOUPAL, CHARLES G. CALD ...
    1991 Volume 44 Issue 2 Pages 249-254
    Published: February 25, 1991
    Released: April 19, 2006
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  • MAKOTO TAHARA, TAKAYOSHI OKABE, KAZUO FURIHATA, NOBUO TANAKA, HIDEYO Y ...
    1991 Volume 44 Issue 2 Pages 255
    Published: February 25, 1991
    Released: April 19, 2006
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  • YOSHINORI MINAMI, MASAHITO KOMURO, KUMIKO SAKAWA, NAOBUMI ISHIDA, KEIZ ...
    1991 Volume 44 Issue 2 Pages 256-258
    Published: February 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • HIROYUKI OSADA, HIROYUKI KOSHINO, KIYOSHI ISONO, HIDETOSHI TAKAHASHI, ...
    1991 Volume 44 Issue 2 Pages 259-261
    Published: February 25, 1991
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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