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TADASHI NARITA, MASARU MATSUMOTO, KINICHI MOGI, KEN-ICHI KUKITA, RYUIC ...
1989 年 42 巻 3 号 p.
347-356
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
Streptomyces ravidus S50905 was found to produce a new antibiotic, deacetylravidomycin
N-oxide, together with ravidomycin and deacetylravidomycin in a culture medium containing sodium anthraquinone-β-sulfonate. The structure of this new compound was determined from NMR and mass spectrometric data, and further confirmed by chemical synthesis from deacetylravidomycin.
Deacetylravidomycin
N-oxide was antitumor active against P388 leukemia and Meth A fibrosarcoma in a wide range of doses, and considerably less toxic than deacetylravidomycin. Its antibacterial activity was less potent than deacetylravidomycin. Ravidomycin
N-oxide was also synthesized from ravidomycin and its biological properties were tested.
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MING-S. Kuo, DAVID A. YUREK, STEPHEN A. MIZSAK
1989 年 42 巻 3 号 p.
357-360
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The structure of ficellomycin, an antibiotic previously discovered by ARGOUDELIS
et al., is elucidated as valyl-2-[4-guanidyl-1-azabicyclo[3.1.0]hexan-2-yl]glycine (
1) by NMR, MS, and derivatization studies. The l-azabicyclo[3.1.0]hexane moiety in
1 represents an unusual ring system making ficellomycin a unique natural product compound.
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ANGELO BORGHI, PIERO ANTONINI, MARGHERITA ZANOL, PIETRO FERRARI, LUIGI ...
1989 年 42 巻 3 号 p.
361-366
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
Teicoplanin is an antibiotic produced by fermentation of
Actinoplanes teichomyceticus as a complex formed by five closely related glycopeptides characterized by different tatty acid chains of ten and eleven carbon atoms. In addition, minor quantities of related substances are present. Two of them, named RS-1 and RS-2, were shown to be teicoplanins having as fatty acid chains 10-methylundecanoic acid and
n-dodecanoic acid, respectively. Other two related substances, named RS-3 and RS-4, have now been isolated and purified starting from fermentation broths of a mutant of the same microorganism producing them in substantial amounts. This was achieved by semipreparative reversed-phase liquid chromatography carried out on high-pressure scale.
The structures were assigned on the basis of
1H NMR spectra and homonuclear COSY 2D experiments and fast atom bombardment MS spectrometry, in comparison with the large mass of data till now accumulated on teicoplanin. RS-3 and RS-4 are teicoplanins having as fatty acid chains 6-methyloctanoic acid and n-nonanoic acid, respectively.
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I. DERIVATIVES SUBSTITUTED AT C(5) OR C(6) OF THE PIPERAZINE RING
DAVID T. DAVIES, FRANK P. HARRINGTON, SARAH J. KNOTT, ROBERT SOUTHGATE
1989 年 42 巻 3 号 p.
367-373
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The synthesis and antibacterial activity of a series of penicillins and 6α-formamidopenicillins containing a C(5) or C(6)-substituted piperazine-2, 3-dione moiety in the C(6)-β-sidechain is described.
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TOMOYUKI SHIBATA, YUKIO SUGIMURA
1989 年 42 巻 3 号 p.
374-381
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The diastereoselective synthesis of the 1-β-methylcarbapenems, (1
R, 5
R, 6
S)-6-((
R)-1- hydroxyethyl)-2-((
S)-1-acetimidoylpyrrolidin-3-ylthio)-1-methyl-1-carbapen-2-em-3-carboxylic acid and sodium (1
R, 5
R, 6
S-6-((
R)-1-hydroxyethyl)-2-(5-chloro-2-oxobenzoxazolm-3-yl)-lmethyl-1-carbapen-2-em-3-carboxylate has been achieved. The key step was an aldol reaction between the achiral boron enolate which was generated from dibutylboron triflate and 3-propionyl-2-oxobenzoxazoline, and (3
R, 4
R)-4-acetoxy-3-((
R)-1-hydroxyethyl)azetizin-2-one.
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LA VERNE D. BOECK, DAVID S. FUKUDA, BERNARD J. ABBOTT, MANUEL DEBONO
1989 年 42 巻 3 号 p.
382-388
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
Echinocandin B (ECB) is a lipopeptide antifungal agent produced by several species of
Aspergillus. The lipid side chain of cyclic lipopeptides is known to be an important determinant of their antibiotic activity and toxicity. Deacylation of another lipopeptide antibiotic, A21978C, had formerly been accomplished with
Actinoplanes utahensis. In spite of the structural dissimilarities between the peptide cores and acyl side chains of A21978C and ECB,
A. utahensis also removed the linoleoyl acyl unit from the amino terminus of ECB to yield the bioinactive cyclic peptide core, or "nucleus". The ECB nucleus, which contained a new titratable group at the
N-terminus, was subsequently employed for chemical reacylation with other side chains to yield a variety of novel ECB analogs. One of these, cilofungin (LY121019), containing an
N-(4-
n-octyloxybenzoyl)acyl unit, is currently undergoing clinical evaluation.
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M. DEBONO, B. J. ABBOTT, D. S. FUKUDA, M. BARNHART, K. E. WILLARD, R. ...
1989 年 42 巻 3 号 p.
389-397
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The antifungal antibiotic, echinocandin B (ECB), was modified by a sequential procedure in which the initial step involved enzymatic removal of the native
N-linoleoyl group from the
N-terminus using an
Actinoplanes utahensis culture. The resulting product, ECB nucleus, was reacylated using active esters or acid halides of various substituted acids to give a series of ECB analogs. These analogs possessed anti-
Candida activity both
in vitro and
in vivo (mice). Other studies have shown that one of these, cilofungin, the 4-
n-octyloxybenzoyl-ECB analog (LY121019), has excellent anti-
Candida activity, low toxicity and is superior to other available antifungal antibiotics.
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H.-R. TSOU, Z. H. AHMED, R. R. FIALA, M. W. BULLOCK, G. T. CARTER, J.J ...
1989 年 42 巻 3 号 p.
398-406
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The biosynthesis of LL-F28249α in a culture of
Streptomyces cyaneogriseus has been studied using
13C,
14C and
18O labeled precursors. A complete
13C NMR spectrum of F28249α has been assigned. Incorporation studies using
13C labeled precursors indicate that the carbon skeleton of F28249α is derived from seven acetate, six propionate and one 2-methylpropionate units. The origin of the oxygen atoms of F28249α has been examined by feeding [1-
13C,
18O
2]acetate, [1-
13C,
18O
2]propionate, [2-
13C]acetate/
18O
2 and
18O
2 separately to the fermentation culture and analyzing the resulting labeled LL-F28249α samples by
13C NMR, electron impact MS and chemical ionization MS. Out of a total of eight oxygen atoms in LL-F28249α, four oxygen atoms are derived from acetate, three from propionate and one from molecular oxygen.
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DAISUKE KOMAGATA, HIDEAKI SHIMADA, SHIGEO MURAKAWA, AKIRA ENDO
1989 年 42 巻 3 号 p.
407-412
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The microbial metabolites monaeolins J and L are specific inhibitors of 3-hydroxy-3-methylglutaryl Co A reductase, the rate-limiting enzyme in cholesterol synthesis. The producing strain
Monascus ruber M 4681 was found to convert exogenously added monacolin L to J. In this hydroxylation reaction
18O
2 was incorporated into monacolin L, giving [
18O]monacolin J. The cell-free extracts of
M. ruber quantitatively hydroxylated monacolin L to J, and molecular oxygen was required for the hydroxylation. The enzyme was located in the microsomal fraction and specific for NADPH. The enzyme activity was inhibited by metyrapone, carbon monoxide, sulfhydryl reagents and cytochrome c. The results indicate that monacolin L is the precursor of monacolin J, and that a monooxygenase is involved in this reaction.
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MICHIKO M. NAKANO, TAKAO KIKUCHI, HIROSHI MASHIKO, HIROSHI OGAWARA
1989 年 42 巻 3 号 p.
413-422
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The appropriate location and orientation of the kanamycin resistance gene (
kmr) cloned on multicopy plasmids were determined by subcloning experiments. The transcription start site was identified by high-resolution SI mapping and the
kmr mRNA was shown to have a long leader of about 400 bp. An additional transcript upstream of the
kmr gene was also detected, which ran in the opposite direction and overlapped 2 to 3 nucleotides with the
kmr transcript. The presumptive promoter region of this physiologically unidentified RNA was similar to the
Escherichia coli promoter consensus sequence both in the -10 and -35 regions, whereas the putative promoter region of the
kmr gene exhibited sequence similarities in the - 10 region to the promoters of the endoglycosidase H (
endoH) and the viomycin phosphotransferase (
vph) genes from
Streptomyces.
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MICHIKO M. NAKANO, IKUO BUTSUYA, HIROSHI OGAWARA
1989 年 42 巻 3 号 p.
423-430
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The previously cloned kanamycin resistance gene (
kmr) from
Streptomyces kanamyceticus ISP5500 was shown to modify the 3OS ribosomal subunit in a subunit exchange experiment. The
kmr gene, which was normally repressed in
S. kanamyceticus, appeared to be induced under growth conditions which activated kanamycin biosynthesis. SI mapping analysis revealed that the expression of the
kmr gene was regulated at the transcriptional level. Acetylation of kanamycin is another resistance mechanism in the kanamycin producer. However, unlike
kmr-mediated resistance, the enzyme which catalyzed acetylation was not regulated coordinately with kanamycin biosynthesis.
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HARUO TANAKA, KAZUHITO KAWAKITA, HIDEKAZU SUZUKI, PRISKA SPIRI-NAKAGAW ...
1989 年 42 巻 3 号 p.
431-439
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The mode of action of cervinomycin, which is a new antibiotic active against Grampositive bacteria including anaerobes, was studied in
Staphylococcus aureus using triacetylcervinomycin A
1 (ACVM), an acetyl derivative of cervinomycin A
1. ACVM inhibited strongly the growth of the organism when it was added to a culture at the time of inoculation at a concentration of 1.0μg/ml, but did not inhibit when added to a logarithmic phase culture even at 10.0 μg/ml. The antibiotic also inhibited the incorporation of labeled precursors of cell wall peptidoglycan (
N-acetylglucosamine), RNA (uridine), DNA (thymidine) and protein (L-leucine) into both whole cell and acid-insoluble macromolecular fractions. ACVM stimulated the leakage of UV
260-absorbing materials, amino acids and potassium ions from resting cells and protoplasts. Phospholipids partially reversed the inhibitory activity of ACVM in a growing culture. These findings suggest that ACVM interact with phospholipids in the cytoplasmic membrane and then interfere with the membrane transport system.
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MASAHIRO NATSUME, KAZUHISA YASUI, SHINGO MARUMO
1989 年 42 巻 3 号 p.
440-447
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
Ca
2+ induced the formation of aerial mycelia in
Streptomyces ambofaciens. Its effect was inhibited by ethylene glycol bis(β-aminoethyl ether)-
N,
N,
N',
N'-tetraacetic acid, a Ca
2+ specific chelating agent. A survey of 36 strains of actinomycetes showed that Ca
2+ regulated aerial mycelium formation in 21 (58%) of them. The Ca
2+ concentration required for aerial mycelium formation in the culture medium ranged from 0.1 to 1.5 mM.
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JUNKO YOSHIDA, SHOZO TAKAMURA, SHIRO SUZUKI
1989 年 42 巻 3 号 p.
448-453
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
A simplified method for purification of an antitumor acidic glycoprotein (SAGP) from
Streptococcus pyogenes (Su strain) by immunoaffinity chromatography is described. A cellfree crude extract prepared from the cocci was applied to the anti-SAGP IgG coupled Sepharose column, and elution was conducted with an alkaline buffer. The material eluted was confirmed to be homogeneous and identical with SAGP as demonstrated by both relative mobility on the SDS-polyacrylamide gel column and the antigenicity on the double diffusion agar plate. The cell-growth inhibitory activity of SAGP prepared by the present method was almost the same as that of SAGP purified by the previous time-consuming method. Since this simplified method provides a higher yield of SAGP, it will be useful in further studies on the biological properties of SAGP.
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JENNIFER M. WILSON, PETER C. T. HANNAN, CHRISTINE SHILLINGFORD, DAVID ...
1989 年 42 巻 3 号 p.
454-462
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
The antimicrobial activity of a new semi-synthetic oral erythromycin derivative, ER 42859, was evaluated
in vitro and
in vivo in comparison with erythromycin, spiramycin, josamycin, oleandomycin and the newer semi-synthetic derivatives flurithromycin, roxithromycin and A-56268. MIC values of ER 42859 were superior to those of roxithromycin, oleandomycin, josamycin and spiramycin but generally 2-fold poorer than those of erythromycin. The activity equalled that of erythromycin against
Haemophilus influenzae and was superior to that of roxithromycin and A-56268 against this organism. MIC values of the compound were greatly influenced by pH due to the dibasic nature of the molecule. ER 42859 had markedly superior activity to erythromycin, spiramycin, josamycin, oleandomycin and flurithromycin against experimental infections in mice and similar activity to roxithromycin and A-56268. Blood and tissue levels were high and prolonged in rodents. In volunteers, blood levels were prolonged but inferior to those of erythromycin.
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SHUNICHIRO MASAKI, TAKAO KONISHI, NAOKI TSUJI, JUNICHI SHOJI
1989 年 42 巻 3 号 p.
463-466
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
Resorcinomycin A,
N-[(
S)-α-guanidino-3, 5-dihydroxy-4-isopropylphenylacetyl]glycine,
S-RSM-A, a new antibiotic produced by
Streptoverticillium roseoverticillatum, has an antibacterial spectrum directed towards mycobacterial species.
It is not active against Gram-negative and Gram-positive bacteria, except mycobacteria and weakly active against mycoplasmas.
In vitro activities of the
S-,
R- and
S,
R-isomers of RSM-A against atypical mycobacterial strains were compared with those of streptomycin (SM) and kanamycin (KM) by 2-fold agar dilution methods using Middlebrook 7H10 agar medium. Although
R-RSM-A and
S,
R-RSM-A were comparable or inferior to both antibiotics, the antimycobacterial activity of
S-RSM-A was superior to that of SM and KM.
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KUNIO ISSHIKI, TSUTOMU SAWA, HIROSHI NAGANAWA, NAOKO MATSUDA, SEIKO HA ...
1989 年 42 巻 3 号 p.
467-469
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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SEPHEN H. LARSEN, DONNIS M. BERRY, JONATHAN W. PASCHAL, JAMES M. GILLI ...
1989 年 42 巻 3 号 p.
470-471
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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JOHN H. COATS, GRACE P. LI, MING-S. T. Kuo, DAVID A. YUREK
1989 年 42 巻 3 号 p.
472-474
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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MING-S. T. Kuo, DAVID A. YUREK, JOHN H. COATS, GRACE P. LI
1989 年 42 巻 3 号 p.
475-478
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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HISAYO NOMOTO, SHIGEO KATSUMATA, KEIICHI TAKAHASHI, SHINJI FUNAYAMA, K ...
1989 年 42 巻 3 号 p.
479-481
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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GEOFFREY W. GRIGG, CHRISTINA M. COLLIS
1989 年 42 巻 3 号 p.
482-485
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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TAKAAKI AOYAGI, HAJIME MORISHIMA, KATSUHISA KOJIRI, TAKUZO YAMAMOTO, F ...
1989 年 42 巻 3 号 p.
486-488
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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KATSUHISA KOJIRI, HAJIME MORISHIMA, TAKUZO YAMAMOTO, TAKAAKI AOYAGI, T ...
1989 年 42 巻 3 号 p.
489-490
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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TOMOMI HIDAKA, MICHIKO MORI, SATOSHI IMAI, OSAMU HARA, KOZO NAGAOKA, H ...
1989 年 42 巻 3 号 p.
491-494
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー
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HIROSHI YONEHARA
1989 年 42 巻 3 号 p.
495
発行日: 1989/03/25
公開日: 2006/04/19
ジャーナル
フリー