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I. TAXONOMY OF THE PRODUCING ORGANISM AND ISOLATION AND BIOLOGICAL PROPERTIES OF THE ANTIBIOTICS
ATSUSHI TAKAHASHI, NORIKO SAITO, KUNIMOTO HOTTA, YOSHIRO OKAMI, HAMAO ...
1986 Volume 39 Issue 8 Pages
1033-1040
Published: 1986
Released on J-STAGE: April 19, 2006
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A bacterial isolate from soil, designated as TB-2125 had a unique pattern of multiple resistance to aminoglycoside antibiotics (AG) and produced new nucleoside antibiotics. Taxonomic properties of this strain fell into those of
Bacillus circulans, providing unique characteristics such as strict susceptibility to acidic pH, motility of colony as well as multiple AG-resistance. Two new antibiotics which were named bagougeramines A and B had a broad antimicrobial activity and a specific activity against the two spotted spider mite.
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II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION
ATSUSHI TAKAHASHI, DAISHIRO IKEDA, HIROSHI NAGANAWA, YOSHIRO OKAMI, HA ...
1986 Volume 39 Issue 8 Pages
1041-1046
Published: 1986
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Bagougeramines A and B obtained as sulfates were soluble in water and positive to Sakaguchi, chlorine-tolidine and ninhydrin color reactions. Their structures were determined by acid hydrolysis and spectroscopic analysis. Structurally they were closely related to gougerotin and they contained the guanidino-D-alanine instead of the serine residue in gougerotin. Bagougeramine B had the spermidine instead of the 6'-NH
2 in structure of bagougeramine A.
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TAXONOMY, FERMENTATION, ISOLATION AND CHARACTERIZATION
HIROSHI YAMAGUCHI, SHINGO SATO, SHIRO YOSHIDA, KINJI TAKADA, MASAYOSHI ...
1986 Volume 39 Issue 8 Pages
1047-1053
Published: 1986
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A new antibiotic capuramycin was isolated from the culture filtrate of
Streptomyces griseus 446-S3 by adsorption and partition column chromatography. Based on its chemical structure being an uracil nucleoside with a caprolactam substituent, this substance was named as capuramycin. This paper describes the taxonomy of a producing organism, fermentation, isolation, characterization and biological properties of capuramycin.
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TAXONOMY, FERMENTATION, ISOLATION, STRUCTURE DETERMINATION, SYNTHESIS AND ANTIBACTERIAL ACTIVITY
PUSHPA D. SINGH, JANICE H. JOHNSON, CAROL A. AKLONIS, JOSEPH O'SULLIVA ...
1986 Volume 39 Issue 8 Pages
1054-1058
Published: 1986
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A new antibiotic, SQ 30, 957, 4-diazo-3-methoxy-2, 5-cyclohexadien-1-one, has been isolated from fermentation broths of
Penicillium funiculosum. The structure (1) was deduced from its spectroscopic properties and its degradation reaction. SQ 30, 957 has excellent activity against anaerobic bacteria such as
Clostridium and
Bacteroides and has moderate activity against aerobic bacteria. The compound has an LD
50 of less than 17 mg/kg in mice by intraperitoneal administration.
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HIROSHI KASE, KAZUYUKI IWAHASHI, YUZURU MATSUDA
1986 Volume 39 Issue 8 Pages
1059-1065
Published: 1986
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K-252a, a metabolite isolated from the culture broth of
Nocardiopsis sp. K-252a, was found to exhibit an extremely potent inhibitory activity on protein kinase C. The IC
50 value was 32.9 nM.
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SATOSHNI AKANISHI, YUZURU MATSUDA, KAZUYUKI IWAHASHI, HIROSHI KASE
1986 Volume 39 Issue 8 Pages
1066-1071
Published: 1986
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Nocardiopsis sp. K-290 was found to produce novel metabolites, designated K-252b, c and d, which were structurally related to K-252a. These compounds were isolated from the culture broth and the physico-chemical and biochemical properties were examined. The compounds strongly inhibited protein kinase C. IC
50 values (the concentrations causing 50% inhibition) for the effects of K-252b, c and d on the rat brain enzyme were 38.3, 214, and 337 nM, respectively.
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TOHRU YASUZAWA, TAKAO IIDA, MAYUMI YOSHIDA, NORIAKI HIRAYAMA, MITSURU ...
1986 Volume 39 Issue 8 Pages
1072-1078
Published: 1986
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The structures of four new protein kinase C inhibitors of microbial origin, K-252a, b, c and d were determined by spectral studies and chemical conversion.
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SATOSHI OMURA, NOBUTAKA IMAMURA, KAZUHITO KAWAKITA, YOKO MORI, YUKIKO ...
1986 Volume 39 Issue 8 Pages
1079-1085
Published: 1986
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A soil isolate,
Streptomyces sp. WK-142, was found to produce new acid protease inhibitors, ahpatinins A, B, D, E, F and G active against pepsin and renin. Ahpatinin C was found to be identical with pepstatin A. The structure determinations were based on mass spectral data. Four of the compounds contain the unusual amino acid, 4-amino-3-hydroxy-5-phenylpentanoic acid as a building component.
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T. R. HURLEY, T. A. SMITKA, J. H. WILTON, R. H. BUNGE, G. C. HOKANSON, ...
1986 Volume 39 Issue 8 Pages
1086-1091
Published: 1986
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Two antibiotics were isolated from culture broths of a
Streptomyces sp. and identified as 8″-hydroxypactamycin and 7-deoxypactamycin. The latter antibiotic was shown to be identical to cranomycin. An additional compound, 8″-hydroxypactamycate, was also isolated.
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TAKAYUKI NAITO, SHIMPEI ABURAKI, HAJIME KAMACHI, YUKIO NARITA, JUN OKU ...
1986 Volume 39 Issue 8 Pages
1092-1107
Published: 1986
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The synthesis of a series of 7-[(
Z)-2-(2-aminothiazol-4-yl)-2-oxyiminoacetamido]-3-ammoniomethyl-3-cephems is described. Variations of an oxyimino moiety in the 7-side chain and a quaternary ammonium moiety in the 3-side chain were examined and structure-activity relationships studied. BMY-28142, the 3-(
Nmethylpyrrolidinio)methyl derivative of the 7-α-methoxyimino series of cephalosporins, exhibited broad antimicrobial activity against both Gram-positive and Gram-negative bacteria including
Pseudomonas aeruginosa.
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H. A. KIRST, M. DEBONO, J. E. TOTH, B. A. TRUEDELL, K. E. WILLARD, J. ...
1986 Volume 39 Issue 8 Pages
1108-1122
Published: 1986
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A large number and wide variety of acyl derivatives of the tylosin-related macrolides 23-demycinosyltylosin (DMT), 23-demycinosyloxytylosin (DMOT) and 5-
O-mycaminosyltylonolide (OMT) were synthesized and evaluated. This encompassed conversion of the hydroxyl groups at 2', 4' and 23 of the appropriate macrolides to the corresponding esters, in which a variety of different substitution patterns were examined. A wide range of acyl substituents was investigated, particularly for 23-
O-acyl derivatives of OMT, since these were substantially more active
in vitro than OMT itself. However, the acyl derivatives which were prepared demonstrated no substantial improvement in oral efficacy or bioavailability over the parent macrolides.
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JUNG J. LEE, JONATHAN P. LEE, PAUL J. KELLER, CHARLES E. COTTRELL, CHI ...
1986 Volume 39 Issue 8 Pages
1123-1134
Published: 1986
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Feeding experiments with [
U-
13C
3]- and (2
R)-[1-
2H
2]glycerol showed that glycerol is incorporated intact into carbon atoms 22, 23 and 24 of the aglycone of chlorothricin. C-1 of glycerol gives rise to C-22 with retention of one atom of deuterium, which occupies the H-22
R position. A mechanism for the assembly of the aglycone is proposed which invokes phosphoenolpyruvate as the direct precursor of the 3-carbon moiety and a Baeyer-Villiger oxidation as the mode of formation of the macrocyclic lactone functionality. A feeding experiment with [1, 2-
13C
2]succinate suggests that the propionate units of the aglycone polyketide are formed entirely via the methylmalonyl-CoA mutase reaction. The formation of the two 2, 6-dideoxy-D-rhamnose moieties of chlorothricin from glucose was shown to involve replacement of the 2-hydroxyl group of the sugar by hydrogen with inversion of configuration at C-2. This contrasts with the retention stereochemistry observed earlier for the analogous formation of the 2, 6-dideoxyhexose moiety of the antibiotic granaticin.
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METABOLIC INTERRELATIONSHIPS OF CARBOXYLIC ACID PRECURSORS AND POLYETHER ANTIBIOTICS
MARY M. SHERMAN, STEVE YUE, C. RICHARD HUTCHINSON
1986 Volume 39 Issue 8 Pages
1135-1143
Published: 1986
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The metabolic interrelationships of isobutyrate,
n-butyrate, and propionate in
Streptomyces lasaliensis are established to show how these acids are used as precursors for the biosynthesis of the polyether antibiotic, lasalocid A.
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JOSÉ M. LUENGO, MANUEL J. LÓPEZ-NIETO, FRANCISCO SALTO
1986 Volume 39 Issue 8 Pages
1144-1147
Published: 1986
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Benzylpenicillin, a typical antibiotic produced by some species of fungi, was obtained by direct cyclization of the heteropeptide phenylacetyl-L-cysteinyl-D-valine using cell-free extracts of
Streptomyces clavuligerus. This is the first description of evidence of the synthesis of benzylpenicillin from a non natural molecule using a bacterial enzyme.
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AKITO NAKAMURA, KAZUO NAGAI, SEIKICHI SUZUKI, KUNIO ANDO, GAKUZO TAMUR ...
1986 Volume 39 Issue 8 Pages
1148-1154
Published: 1986
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A novel method of screening for immunomodulating substances is developed employing lymphocytes and three mitogens. Concanavalin A (Con A) and phytohemagglutinin (PHA) are applied as T cell specific stimulants and lipopolysaccharide (LPS) as a B cell specific stimulant respectively. The lymphocytes obtained from mouse spleen are cultured with an antibiotic or a sample extract in the presence or absence of mitogen for three days and pulsed
with [
33H]thymidine for five hours before harvest. Differential effects of a sample compound on [3H]thymidine incorporation by the activated and quiescent lymphocytes are scored. In this procedure most of the tested antibiotics or chemical compounds with different mode of actions show non-specific effects. Cyclosporin A, a potent immunosuppresive substance, suppresses both Con A and PHA responses more extensively than LPS response and quiescent cell growth, and two cytochrome bc1, complex inhibitors, funiculosin and antimycin A3, are less suppressive to PHA response than to the others. The present system was also applied to the methanol extracts of the culture broths prepared from the type strains of Actinomycetes and Penicillium.
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AKITO NAKAMURA, KAZUO NAGAI, KUNIO ANDO, GAKUZO TAMURA
1986 Volume 39 Issue 8 Pages
1155-1159
Published: 1986
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In the course of screening for immunomodulating substances among microbial metabolites using a triple mitogen assay system, we detected an immunosuppressive activity which is similar to cyclosporin A. Two active components were isolated as red pigments from the fermentation broth of
Streptomyces hiroshimensis and they were identified with prodigiosin 25-C and metacycloprodigiosin respectively. These compounds inhibited T lymphocyte proliferation which was induced by plant lectins, concanavalin A (Con A) and phytohemagglutinin (PHA), much more extensively than B lymphocyte proliferation which was induced by lipopolysaccharide (LPS). Prodigiosin 25-C completely inhibited induction of cytotoxic T cells in a mixed lymphocyte reaction (MLR) at 4 ng/ml.
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II. KF8940 (2-n-HEPTYL-4-HYDROXYQUINOLINE-N-OXIDE), A POTENT AND SELECTIVE INHIBITOR OF 5-LIPOXYGENASE, PRODUCED BY PSEUDOMONAS METHANICA
SHIGETO KITAMURA, KAZUKO HASHIZUME, TAKAO IIDA, ETSUKO MIYASHITA, KUNI ...
1986 Volume 39 Issue 8 Pages
1160-1166
Published: 1986
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Pseudomonas methanica KY4634 was found to produce 5-lipoxygenase inhibitor designated KF8940, MY12-62a and MY12-62c. The inhibitors were purified by solvent extraction, silica gel column chromatography, reversed-phase low pressure liquid chromatography and crystallization. The chemical structures of KF8940, MY12-62a and MY12-62c were determined to be 2-
n-heptyl-4-hydroxyquinoline-
N-oxide, 2-
n-heptyl-4-hydroxyquinoline and 3-
n-heptyl-3-hydroxy-1, 2, 3, 4-tetrahydroquinoline-2, 4-diore, respectively, on the basis of their physico-chemical properties. Among them, KF8940 was the most potent inhibitor. The compound inhibited 5-lipoxygenase of rat basophilic leukemia cells in a dose-dependent manner and the half maximal inhibitory concentration (IC
50) was 1.5 × 10
-7 M. At this concentration, KF8940 did not inhibit bovine platelet 12-lipoxygenase and cyclooxygenase, and the IC
50 values for these enzyme were 3.5 × 10
-5 M and 1.7 × 10
-4 M, respectively. The results indicated that KF8940 is a potent and selective inhibitor of 5-lipoxygenase. The IC
50 value of MY12-62c for 5-lipoxygenase was 1.9 × 10
-5 M and that of MY12-62a was 1.9 × 10
-5 M.
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MASAHIRO TAKAHATA, YOSHIKO YAMASHIRO, AKIRA YOTSUJI, YOSHIKAZU FUKUOKA ...
1986 Volume 39 Issue 8 Pages
1167-1171
Published: 1986
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The antibacterial activity of 5-fluorouracil, an antineoplastic agent, was found to be enhanced by piperacillin, a β-lactam antibiotic, resulting in a synergism. It was considered that the synergism was caused by an increase of 5-fluorouracil uptake into the bacterial cell. On the other hand, amount of piperacillin bound to penicillin binding protein (PBP) did not change when 5-fluorouracil was added. The morphological change of the cell was due to the 5-fluorouracil when synergism appeared between 5-fluorouracil and piperacillin.
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FUMINORI ABE, MICHIKO HAYASHI, HIROO HORINISHI, AKIRA MATSUDA, MASAAKI ...
1986 Volume 39 Issue 8 Pages
1172-1177
Published: 1986
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The effect of ubenimex on graft-versus-host reaction and delayed cutaneous hypersensitivity in mice was studied. Ubenimex enhanced the graft-versus-host reaction in a dose range from 0.005 to 0.5 mg/kg. Ubenimex inhibited the aging-caused decrease of delayed cutaneous hypersensitivity to oxazolone and the efficacy was greater with older mice. Ubenimex also inhibited mitomycin C and L1210-caused decreases of delayed cutaneous hypersensitivity to picryl chloride. However, the excess decrease caused by mitomycin C was not significantly altered by ubenimex.
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MASAYA NAKAGAWA, KAZUO FURIHATA, KEIKO FURIHATA, KAZUYOSHI ADACHI, HAR ...
1986 Volume 39 Issue 8 Pages
1178-1179
Published: 1986
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SATOSHI OMURA, AKIRA NAKAGAWA, NOBUKO FUKAMACHI, KAZUHIKO OTOGURO, BON ...
1986 Volume 39 Issue 8 Pages
1180-1181
Published: 1986
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VIYYOOR M. GIRIJAVALLABHAN, ASHIT K. GANGULY, PATRICK A. PINTO, RICHAR ...
1986 Volume 39 Issue 8 Pages
1182-1186
Published: 1986
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VIYYOOR M. GIRIJAVALLABHAN, ASHIT K. GANGULY, YI-TSUNG LIU, PATRICK A. ...
1986 Volume 39 Issue 8 Pages
1187-1190
Published: 1986
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