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ISOLATION, PURIFICATION AND STRUCTURE DETERMINATION
STEPHEN J. BOX, NIGEL J. COATES, CHRIS J. DAVIS, MARTIN L. GILPIN, CAT ...
1991 Volume 44 Issue 8 Pages
807-813
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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Two novel glycopeptide antibiotics MM 55266 and MM 55268 containing fatty acid acyl functions, and of molecular formula C
86H
89N
8O
35Cl
5 and C
87H
91N
8O
35C
15, respectively, have been isolated and identified from a complex produced by
Amycolatopsis sp. NCIB 40089. Fermentation conditions for their production, and methods for their isolation are described. Structures have been deduced by use of COSY and NOE NMR techniques and supported by chemical degradation studies. Both glycopeptides possessed good antibacterial activity against Gram-positive organisms.
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I. TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL CHARACTERISTICS
KANKI KOMIYAMA, SHINJI FUNAYAMA, YUMI ANRAKU, MASAMI ISHIBASHI, YOKO T ...
1991 Volume 44 Issue 8 Pages
814-818
Published: August 25, 1991
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A new antibiotic, okicenone was isolated from the culture broth of
Streptomyces sp. KO-3599. The antibiotic possesses cytocidal activity against mammalian tumor cells
in vitro at concentrations of 0.53-11.0μg/ml whereas the antibiotic showed no antimicrobial activities against Gram-positive and Gram-negative bacteria, fungi or yeast at a concentration of 1, 000μg/ml.
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II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE ELUCIDATION
SHINJI FUNAYAMA, MASAMI ISHIBASHI, KANKI KOMIYAMA, SATOSHI OMURA
1991 Volume 44 Issue 8 Pages
819-823
Published: August 25, 1991
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The structure of a new cytocidal antibiotic, okicenone was elucidated to be 3, 4-dihydro-4, 6, 9-trihydroxy-8-methyl-1(2
H)-anthracenone on the basis of spectroscopic methods.
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TAXONOMY, ISOLATION, PHYSICO-CHEMICAL PROPERTIES, STRUCTURE AND BIOLOGICAL ACTIVITY
MINORU HANADA, KEIKO KANETA, YUJI NISHIYAMA, YUTAKA HOSHINO, MASATAKA ...
1991 Volume 44 Issue 8 Pages
824-831
Published: August 25, 1991
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A new antitumor antibiotic hydramycin was isolated from the fermentation broth of
Streptomyces violaceus P950-4 (ATCC 53807). It showed potent antibacterial and cytotoxic activity and increased the survival time of mice inoculated with P388 leukemia. A new structure related to the pluramycin group antibiotics was assigned by its spectroscopic experiments.
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I. DISCOVERY, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURAL ELUCIDATION
YUMIKO ITOH, HIROSHI SHIMURA, MAYUMI ITO, NAOHARU WATANABE, MICHIO YAM ...
1991 Volume 44 Issue 8 Pages
832-837
Published: August 25, 1991
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A new subspecies of
Streptomyces rishiriensis A-5969 (PERM BP-1394) was isolated and shown to produce a novel α, β-unsaturated γ-lactone derivative, MH-031, which exhibited hepatoprotective activity in primary cultured rat hepatocytes intoxicated with D-galactosamine.
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RAY S. DEWEY, OTTO D. HENSENS, ALAN W. DOUGLAS, GEORG ALBERS-SCHÖ ...
1991 Volume 44 Issue 8 Pages
838-843
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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The antibiotic heneicomycin (
1), C
44H
62N
2O
11, was isolated from cultures of
Streptomyces filipinensis as an amorphous yellow powder. Mass spectral and NMR analysis showed the compound to be a deoxy modification of aurodox (
2), a member of the elfamycin antibiotic family. A marked change in mass spectral fragmentation compared to aurodox and
1H NMR couplings indicated the absence of the hydroxyl at position 30 of aurodox (position 3 of the tetrahydropyran).
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BERNARD PIROTTE, JACQUES DELARGE, JACQUES COYETTE, JEAN-MARIE FRERE
1991 Volume 44 Issue 8 Pages
844-853
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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Newly synthesized 5-acylaminothiazolium salts and one 5-acylaminothiazolidine, considering their chemical structure and reactivity, have been proposed as potential inhibitors of bacterial serine DD-peptidases. A moderate antibiotic activity with (5-phenylacetylamino-3-thiazolio)acetate and (5-phenylacetylaminothiazolidin-3-yl)acetic acid was observed on
Staphylococcus aureus ATCC 25923. The methyl- and
tert-butyl esters of the thiazolium salt have shown lower MIC values. Moreover, when introduced into an exponential growth phase culture of
S. aureus, the three active thiazolium salts induced a partial lysis indicating an impairing of the bacterial cell wall biosynthesis. The observed time-dependent binding of the best compound to the PBPs of
S. aureus was too slow and occurred at too high concentrations to account for its MIC value. Consequently, the antibiotic activity of the thiazolium salts on the
S. aureus cells seems not to be satisfactorily explained by a penicillin-like interaction with the PBPs.
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I. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 3-THIAZOLIOMETHYL DERIVATIVES
EIJI NAKAYAMA, KOICHI FUJIMOTO, SHIGEKI MURAMATSU, MASAO MIYAUCHI, KAT ...
1991 Volume 44 Issue 8 Pages
854-863
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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The synthesis and the structure-activity relationships of 3-thiazoliomethyl cephalosporins are described. In a series of these parenteral compounds, 2-(2-aminothiazol-4-yl)-(
Z)-2-methoxyiminoacetamido group was found to be a favorable substituent for the C-7 position of the cephem nucleus. They showed potent antibacterial activity against both Gram-positive and Gram-negative bacteria including some β-lactamase producing species.
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II. SYNTHESIS AND BIOLOGICAL PROPERTIES OF CS-461 AND RELATED COMPOUNDS
EIJI NAKAYAMA, KATSUHIKO WATANABE, MASAO MIYAUCHI, KOICHI FUJIMOTO, SH ...
1991 Volume 44 Issue 8 Pages
864-869
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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The synthesis, structure-activity relationships, and biological properties of 3-thiazoliomethyl cephalosporins are described. 7-[2-(2-Aminothiazol-4-yl)-(
Z)-2-methoxyiminoacetamido]-3-[5-(2-hydroxyethyl)-4-methylthiazoliomethyl]-3-cephem-4-carboxylate sulfate (CS-461) showed potent antibacterial activity against a wide variety of bacteria both
in vitro and
in vivo. Furthermore, CS-461 exhibited significantly low acute toxicity in mice.
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YUHPYNG L. CHEN, KIRK HEDBERG, KAREN GUARINO, JAMES A. RETSEMA, MARGAR ...
1991 Volume 44 Issue 8 Pages
870-884
Published: August 25, 1991
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(6
R, 8
S)-(2-Benzimidazolyl)hydroxymethylpenicillanic acids (
1a-
1x) are potent antibacterial agents and β-lactamase inhibitors against Gram-positive bacteria and
Haemophilus influenzae. The corresponding (6
R, 8
R)-isomers (
2a-
2x), the 6, 6-spiro benzimidazole-penam alcohol (
3), (7
R, 9
S)-(2-benzimidazolyl)hydroxymethylcephalosporanic acid (
4), and 6β-(2-benzimidazolyl)aminopenicillanic acid (
5) are much less active as antibacterials or β-lactamase inhibitors. The syntheses and structure-activity relationships of these compounds are discussed. Antibacterial activity and β-lactamase inhibition data are presented.
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M. B. COX, P. ARJUNAN, S. K. ARORA
1991 Volume 44 Issue 8 Pages
885-894
Published: August 25, 1991
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Monocovalent groove binding complexes of antitumor antibiotic naphthyridinomycin and its analogs with DNA sequence d(ATGCAT)
2 have been studied by molecular mechanics to understand which enantiomer of the drug and what chirality at C(7) of the drug are preferred for forming better drug-DNA adducts. The effect of hydroquinone intermediate and the substitution at C(11) on drug-DNA interactions have also been investigated. The results indicate that the enantiomer that forms the best adduct is different from the one reported earlier in the literature. The drug with an
R configuration at C(7) is preferred for binding. The hydroquinone models do not necessarily provide a given analog of the drug with additional favorable DNA interactions. The substitution at-C(11) by OH provides the best binding model. This finding agrees well with the results from previous biochemical studies. The sequence specific studies indicate that the sequence d(ATGCAT)
2 is slightly preferred over others.
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V. P. MARSHALL, J. E. MCGEE, J. I. CIALDELLA, L. BACZYNSKYJ, D. G. CHI ...
1991 Volume 44 Issue 8 Pages
895-900
Published: August 25, 1991
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An enzyme (lincosaminide
O-nucleotidyltransferase) that catalyzes 3-(5'-ribonucleotidylation) of pirlimycin and several other lincosaminide antibiotics has been purified approximately 35-fold from cell-free extracts of
Streptomyces coelicolor Müller NRRL 3532 (UC 5240). The crude enzyme was prepared using lysozyme and was treated with MnCl
2 and (NH
4)
2SO
4. Final purification was achieved by anion exchange chromatography. The pirlimycin reaction product was verified as being pirrimycin-3-(5'-adenylate) by NMR spectroscopy and MS. As a result of purification, this lincosaminide nucleotidylating and inactivating enzyme was separated from the macrolide phosphorylating enzyme also present in the cell-free extract.
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KUNIAKI TATSUTA, HIDEKAZU OZEKI, MAMI YAMAGUCHI, MASASHI TANAKA, TOSHI ...
1991 Volume 44 Issue 8 Pages
901-902
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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II. NEOCARAZOSTATINS A, B AND C, NOVEL FREE RADICAL SCAVENGERS
SHINICHIRO KATO, KAZUTOSHI SHINDO, YOKO KATAOKA, YUJI YAMAGISHI, JUNIC ...
1991 Volume 44 Issue 8 Pages
903-907
Published: August 25, 1991
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NAOKI ABE, NOBUYASU ENOKI, YASUKAZU NAKAKITA, HIDEAKI UCHIDA, RYOICHI ...
1991 Volume 44 Issue 8 Pages
908-911
Published: August 25, 1991
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KUNIAKI TATSUTA, YOSHIHISA NIWATA, KAZUO UMEZAWA, KAZUNOBU TOSHIMA, MA ...
1991 Volume 44 Issue 8 Pages
912-914
Published: August 25, 1991
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MASAYA IMOTO, NAOMI SHIMURA, KAZUO UMEZAWA
1991 Volume 44 Issue 8 Pages
915-917
Published: August 25, 1991
Released on J-STAGE: April 19, 2006
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