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JOHN H. WILTON, GERARD C. HOKANSON, JAMES C. FRENCH
1985 Volume 38 Issue 11 Pages
1449-1452
Published: 1985
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The isolation and properties of PD 118, 576, a new cytotoxic antibiotic obtained from the culture broth of a
Streptomyces sp., are described. The structure of this compound was established by spectral analyses of the parent compound and its tri-
O-acetyl derivative. PD 118, 576 proved to be related to the bafilomycins and therefore is a new member of this recently discovered family of macrolide antibiotics.
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I. TAXONOMY, FERMENTATION, ISOLATION AND CHARACTERIZATION
MASAMI EZAKI, MORITA IWAMI, MICHIO YAMASHITA, SEIJI HASHIMOTO, TADAAKI ...
1985 Volume 38 Issue 11 Pages
1453-1461
Published: 1985
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Biphenomycin A, C
23H
28N
4O
8, and biphenomycin B, C
23H
28N
4O
7, were isolated from the cultured broth of
Streptomyces griseorubiginosus No. 43708. The antibiotics are active
in vitro and
in vivo against bacteria, and are especially potent against Gram-positive bacteria. The acute toxicity of biphenomycin A is very low in mice.
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II. STRUCTURAL ELUCIDATION OF BIPHENOMYCINS A AND B
ITSUO UCHIDA, NOBUHARU SHIGEMATSU, MASAMI EZAKI, MASASHI HASHIMOTO, HA ...
1985 Volume 38 Issue 11 Pages
1462-1468
Published: 1985
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The structures of biphenomycins A and B, novel peptide antibiotics produced by a strain of
Streptomyces, have been established as
1 and
2, respectively, on the basis of spectroscopic and chemical evidence. They are unique in that they are cyclic peptides containing a biphenyl moiety included in a 15-membered ring and show potent antibacterial activities especially against Gram-positive bacteria.
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I. DISCOVERY, IDENTIFICATION, ISOLATION AND CHARACTERIZATION
KEIZO YOSHIDA, MORITA IWAMI, YOSHIKAZU UMEHARA, MOTOAKI NISHIKAWA, ITS ...
1985 Volume 38 Issue 11 Pages
1469-1475
Published: 1985
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WB-3559 A, B, C and D were produced by a bacterium which was classified as a member of the genus
Flavobacterium. These compounds were purified by solvent extraction followed by chromatography on silica gel and then isolated by HPLC. The chemical structures were determined on the basis of chemical and spectroscopic evidence as in the succeeding papers. WB-3559 A, B, C and D stimulated rabbit plasma euglobulin clot lysis time. A chemically synthesized compound (WB-3559 D-syn) stimulated mouse plasma euglobulin clot lysis time when injected intravenously.
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II. STRUCTURE ELUCIDATION AND SYNTHESIS
ITSUO UCHIDA, KEIZO YOSHIDA, YOSHIO KAWAI, SHIGEHIRO TAKASE, YOSHIKUNI ...
1985 Volume 38 Issue 11 Pages
1476-1486
Published: 1985
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The structures of WB-3559 A, B, C and D, new fibrinolytic agents isolated from
Flavobacterium sp. No. 3559, have been elucidated to be as shown in
1, 2, 3 and
4, respectively, on the basis of chemical and spectroscopic evidence. Total synthesis of WB-3559 D (
4) was achieved starting from the optically active aldehyde
14.
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I. TAXONOMY, FERMENTATION AND BIOLOGICAL PROPERTIES
KUNIOMI MATSUMOTO, TAKASHI SHOMURA, MASARU SHIMURA, JUNKO YOSHIDA, MIT ...
1985 Volume 38 Issue 11 Pages
1487-1493
Published: 1985
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A new antibiotic SF-2185 was found active against plant pathogen, particularly the causal organisms of cucumber downy mildew and rice blast. The producing organism, strain SF-2185, is a novel actinomycete and has been identified as
Dactylosporangium aurantiacum subsp.
gifuense.
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BIOSYNTHESIS, ISOLATION AND CHARACTERIZATION
MARVIN D. SCHULMAN, DELIA VALENTINO, OTTO D. HENSENS, DEBORAH ZINK, MA ...
1985 Volume 38 Issue 11 Pages
1494-1498
Published: 1985
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Streptomyces avermitilis normally produces eight avermectins. Avermectin A components contain three methoxyl groups; two on the oleandrose disaccharide and one on the aglycone moiety at C
5. Avermectin B components contain methoxyl groups only on the oleandrose disaccharide. Sinefungin inhibits methylation at all three sites. Addition of sinefungin to
S. avermitilis Agly-1, a mutant which produces virtually only avermectin aglycone A components, alters the fermentation and causes an accumulation of avermectin aglycone B components. Addition of sinefungin to
S. avermitilis 08, a high producing strain, results in accumulation of 8 new avermectins which lack methoxyl groups on the oleandrose moieties as well as the aglycone. These new avermectins were isolated and shown to possess anthelmintic and insecticidal activity.
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I. FLUORINATED VULGAMYCINS
AKIRA KAWASHIMA, HARUO SETO, MASAO KATO, KEIICHI UCHIDA, NOBORU OTAKE
1985 Volume 38 Issue 11 Pages
1499-1505
Published: 1985
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Attempts to prepare fluorinated vulgamycins have been followed by
19 NMR spectroscopy. Isolation, structural elucidation and biological activities of fluorovulgamycins are reported.
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ADRIANO MALABARBA, MAURO LANDI, ROSA PALLANZA, BRUNO CAVALLERI
1985 Volume 38 Issue 11 Pages
1506-1511
Published: 1985
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Actagardine (originally designated as metabolite B or gardimycin) is a polypeptide antibiotic produced by fermentation of
Actinoplanes strains ATCC 31048 and 31049. During the course of repeated fermentations two new compounds, coded D and E, were isolated. Some physico-chemical and biological characteristics of actagardine and of both compounds are presented. Compound D is derived from chemical transformation of actagardine.
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NOBUYOSHI YASUDA, KEIJI MATSUDA, HIDEO TSUTSUMI, TAKAO TAKAYA
1985 Volume 38 Issue 11 Pages
1512-1525
Published: 1985
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The novel, semisynthetic pseudodisaccharide antibiotic, 3-
O-demethylsporaricin A, wassynthesized
via 3-
O-demethylsporaricin B obtained by glycosidation of its aminocyclitol part. The aminocyclitol part was synthesized as D, L-form from D, L-(1, 2, 3/4, 5, 6)-1, 4-bis(benzyloxycarbonylamino)-5, 6-
O-isopropylidene-2, 3, 5, 6-cyclohexanetetraol
via three key steps, namely, deoxygenation, inversion of a hydroxyl group, and
N-methylation. The physical and biological properties of synthetic 3-
O-demethylsporaricin A and an authentic sample derived from sporaricin B were identical.
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APPLICATION TO THE EARLY CHARACTERIZATION OF AMINOGLYCOSIDE ANTIBIOTICS
GENEVIÈVE INCHAUSPE, CHRISTIAN DESHAYES, DANIEL SAMAIN
1985 Volume 38 Issue 11 Pages
1526-1535
Published: 1985
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The use of perfluorinated carboxylic acids counter ions is described for easy combination of ion pair HPLC and FD-MS. This technique is applied to the analysis of aminoglycoside antibiotics and to the problem of their early characterization from culture broths. Reliable molecular weight informations can be obtained with this method from minute amounts of purified products (10 μg) allowing formal identification in most cases.
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II. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 3-ACYLAMINO-2-AZETIDINONE-1-OXYSULFONIC ACIDS
CHOSAKU YOSHIDA, TAKAKO HORI, KAISHU MOMONOI, KATSUYUKI NAGUMO, JOJI N ...
1985 Volume 38 Issue 11 Pages
1536-1549
Published: 1985
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The synthesis and
in vitro antibacterial and β-lactamase inhibitory activity of the 2-azetidinone-1-oxysulfonic acids having a substituent at C-4 position of the β-lactam ring are described. The influence of C-4 substituents on the antibacterial activity was examined for the compounds having α-ureidoacetyl or α-oxyiminoacetyl group as acyl side chain at C-3 position. The antibacterial activity is correlated with the C-4 substituents and acyl side chain. Especially, 4(
R)-methyl substituted derivatives exhibited excellent activity against Gram-negative bacteria and 4-dimethyl substituted derivatives exhibited strong activity against resistant Gram-negative bacteria except for
Pseudomonas aeruginosa.
39 and
40 showed strong inhibitory activity against cephalosporinase of
Enterobacter cloacae H-27.
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S. WOLFE, C. LÜBBE, S. E. JENSEN, H. HERNANDEZ, A. L. DEMAIN
1985 Volume 38 Issue 11 Pages
1550-1554
Published: 1985
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The
S-carboxymethyl-D-cysteine side-chain analogs of cephalosporin C and deacetoxycephalosporin C were found to have markedly increased
in vitro activity against Gram-positive and Gram-negative bacteria compared to the natural antibiotics. The
S-carboxymethyl-L-cysteine analogs were less active than the
S-carboxymethyl-D-cysteine analogs but against most organisms tested, still more active than the natural compounds. The effect of replacement of CH
2 with S was less dramatic in the case of penicillin N and isopenicillin N. The
S-carboxymethyl-D-cysteine analog of deacetoxycephalosporin C was found to be orally available in rats.
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KENJI OKONOGI, AKIRA SUGIURA, MITSUZO KUNO, HIDEO ONO, SETSUO HARADA, ...
1985 Volume 38 Issue 11 Pages
1555-1563
Published: 1985
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Cephem and nocardicin-type monocyclic, β-lactam antibiotics with a formylamino substituent were highly resistant to hydrolysis by both penicillinases and cephalosporinases. Among antibiotics with a methoxy substituent, an
N-sulfonated monocyclic β-lactam antibiotic, sulfazecin was resistant to β-lactamases, but cephem antibiotics were sensitive to the cephalosporinase of
Enterobacter cloacae. The resistance of the antibiotics to the β-lactamases depended primarily on the presence of the substituent, but affinity for the β-lactamases was affected not only by the substituent but also by the presence of other side chains. Formylamino compounds and sulfazecin were as good inducers of β-lactamases as semisynthetic 7-methoxycephalosporins, but naturally occurring 7-methoxycephalosporins were poor inducers. The inducer activities of the antibiotics were not necessarily related to their β-lactamase stabilities. The stabilities of the compounds to the β-lactamases were well reflected in their antibacterial activities against β-lactamase producing bacteria.
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STRUCTURE-ACTIVITY RELATIONSHIPS
KEIJIRO UCHINO, HIROSHI OGAWARA, TETSU AKIYAMA, AKIRA FUKUCHI
1985 Volume 38 Issue 11 Pages
1564-1567
Published: 1985
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Nucleoticidin and melanocidins A and B exhibited potent inhibitory activity against 5'-nucleotidases from rat liver membrane and snake venom. These inhibitors are polysaccharides with highly branched side chains having at least disaccharide units. This conclusion was supported by the results with polysaccharides of known chemical structures. The inhibitors showed non-competitive inhibition with respect to AMP, and urea-treatment caused a marked decrease or a disappearance of the 5'-nucleotidase inhibitory activity. Therefore, it is concluded that steric factors also play an important role in their inhibitory activity.
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JANET C. ONISHI, THOMAS W. MILLER
1985 Volume 38 Issue 11 Pages
1568-1572
Published: 1985
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Streptomyces avermitilis produces avermectin, oligomycin and a polyene antifungal. The latter two compounds account for the antifungal activity in the methanol extracts of the fermentation broth. Pure avermectin does not inhibit fungi or affect fungal chitin metabolism.
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III. MODE OF ACTION OF LEPTOMYCIN B ON SCHIZOSACCHAROMYCES POMBE
TETSUO HAMAMOTO, TAKESHI UOZUMI, TERUHIKO BEPPU
1985 Volume 38 Issue 11 Pages
1573-1580
Published: 1985
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Mode of action of leptomycin B (LMB), a new antifungal antibiotic, was studied with
Schizosaccharomyces pombe. A low concentration of LMB caused inhibition of cell division, producing elongated cells with morphologically altered nuclei and several cell plates, while it inhibited nucleic acid synthesis in intact cells at 100-fold higher concentration. Addition of LMB during G2 phase in synchronous culture blocked following events in cell cycle. Analysis of the effect of LMB on
cdc mutants suggested the antibiotic inhibited some specific step, possibly in M phase just prior to nuclear division.
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MASAHIDE HASOBE, MINEO SANEYOSHI, KIYOSHI ISONO
1985 Volume 38 Issue 11 Pages
1581-1587
Published: 1985
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Guanine 7-
N-oxide produced by
Streptomyces sp. was found to inhibit
in vitro the replication of herpes virus (
Oncorhynchus masou virus, OMV), rhabdo virus (infectious hematopoietic necrosis virus, IHNV) and a bi-segmented double-strand virus (infectious pancreatic necrosis virus, IPNV) derived from salmonids with IC
50 values of about 10μg/ml, 20μg/ml and 32μg/ml, respectively. The agent was not toxic for the host cells (chinook salmon embryo, CHSE-214) at the IC
50 concentrations. Labeling of IHNV viral RNA and host cellular DNA and RNA with [
3H]uridine and [
3H]-thymidine during drug treatment showed that guanine 7-
N-oxide did not reduce the incorporation of these precusors into RNA and DNA. The anti-IHNV activity of guanine 7-
N-oxide was enhanced synergistically by neplanocin A, an inhibitor of RNA methylation. The mechanism of action of guanine 7-
N-oxide is discussed, in regard to maturation of viral messenger RNA including capping.
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RONG TSUN WU, TAKAYOSHI OKABE, SUN HEE KIM, HIDEO SUZUKI, NOBUO TANAKA
1985 Volume 38 Issue 11 Pages
1588-1595
Published: 1985
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Cadeguomycin markedly stimulated the uptake of thymidine, deoxycytidine and uridine into the acid-insoluble fraction of K562 human leukemic cells, but did not significantly affect adenosine incorporation. The enhancement of pyrimidine nucleoside uptake was 6-17 fold over the control. Aspartate incorporation into nucleic acid was not significantly blocked by the antibiotic, suggesting that the stimulation of pyrimidine nucleoside incorporation is not due to the inhibition of
de novo pyrimidine nucleotide synthesis. Net DNA and RNA syntheses, observed by [
32P]phosphate uptake, were not significantly affected by cadeguomycin. The enzymatic activity of thymidine, deoxycytidine and uridine kinases was higher in cadeguomycin-treated cells than in untreated cells, suggesting that the enhancement of pyrimidine nucleoside uptake occurs in the phosphorylation process. The stimulatory activity of cadeguomycin of thymidine uptake was reversed by guanosine and deoxyguanosine, but not by adenosine and deoxyadenosine, suggesting that intracellular metabolism and/or action of cadeguomycin is related to that of guanosine and deoxyguanosine. The stimulation of pyrimidine nucleoside incorporation by cadeguomycin was also found with YAC-1 cells, but not with the other cell lines. The enhancement effect of the antibiotic seems to be not directly related to its cytotoxicity.
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FUSAO TAKUSAGAWA
1985 Volume 38 Issue 11 Pages
1596-1604
Published: 1985
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The physical and biological roles of the cyclic depsipeptides of actinomycin, quinomycin and triostin antibiotic families are proposed by examining the crystal structures of d(GC)-actinomycin D and d(CGTACG)-triostin A. The analyses suggest that not only are DNA-amino acid hydrogen-bonding and chromophore-base pair stacking crucially important for DNA-antibiotic interaction, but also that the unique structure of the cyclic depsipeptides (the perfect hydrophobic character of the inner surface) is equally necessary to insure that these interactions are directed, unambiguous and screened from interference by solvent. Beyond this, the characteristic nature of the outer surfaces suggests a further hypothesis for the biological role of the cyclic depsipeptide rings; when the antibiotics bind in the region around the pause or rho-dependent termination sites on the DNA, the drugs actually terminate transcription by RNA polymerase and cause release of a premature RNA transcript. Termination is likely because the antibiotics carry five to six consecutive apparent A/T sequences on the surface of the cyclic depsipeptide rings, thus presenting a deceptive termination signal to the polymerase.
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I. PHYSICO-CHEMICAL DATA AND PARTIAL STRUCTURE
MASATAKA KONISHI, HIROAKI OHKUMA, KYO-ICHIRO SAITOH, HIROSHI KAWAGUCHI ...
1985 Volume 38 Issue 11 Pages
1605-1609
Published: 1985
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ASAO MURAI, YUSUKE AMINO, TOSHIHIKO ANDO
1985 Volume 38 Issue 11 Pages
1610-1613
Published: 1985
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KANKI KOMIYAMA, KAZUYO IWASAKI, MASAMI MIURA, HIROSHI YAMAMOTO, YOSHIN ...
1985 Volume 38 Issue 11 Pages
1614-1616
Published: 1985
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KIYOSHI ISONO, MASAKAZU URAMOTO, HIROO KUSAKABE, KEN-ICHI KIMURA, KAZU ...
1985 Volume 38 Issue 11 Pages
1617-1621
Published: 1985
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MASAYA NAKAGAWA, HIROYUKI KAWAI, YOICHI HAYAKAWA, HARUO SETO, NOBORU O ...
1985 Volume 38 Issue 11 Pages
1622-1624
Published: 1985
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II. FLUORINATED ACTINOMYCINS
AKIRA KAWASHIMA, HARUO SETO, IMASAO KATO, ARATA YASUDA, KEIICHI UCHIDA ...
1985 Volume 38 Issue 11 Pages
1625-1628
Published: 1985
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HAMAO UMEZAWA, TAKAAKI AOYAGI, TOSHIYUKI TANAKA, HIROYUKI SUDA, AKIRA ...
1985 Volume 38 Issue 11 Pages
1629-1630
Published: 1985
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SATOSHI OMURA, KAZUO TSUZUKI, TOSHIAKI SUNAZUKA, HAJIME TOYOTA, ITSUO ...
1985 Volume 38 Issue 11 Pages
1631-1632
Published: 1985
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