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TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES, STRUCTURE AND BIOLOGICAL ACTIVITY
AKIHIKO FUJIE, TOSHIRO IWAMOTO, NOBUHARU SHIGEMATSU, MASAMI EZAKI, MOT ...
1990 Volume 43 Issue 5 Pages
449-455
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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FR112123 is a new oligopeptide antibiotic produced by
Streptomyces viridochromogenes No. 7587. The structure of FR112123 is elucidated as
N-(
N6-(
N2-glycyl-L-glutaminyl)-D-lysyl)-D-alanine (
1) by spectroscopic and chemical evidence. It resembles a partial structure of peptidoglycan in bacteria. The compound has a superior activity against an
Escherichia coli mutant sensitive to inhibitors of cell wall synthesis, although it has a weak activity against the parent strain. These suggest that FR112123 might act on the biosynthesis of bacterial cell wall.
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JIRO ITOH, YASUO TAKEUCHI, SHUICHI GOMI, SHIGEHARU INOUYE, TAKASHI MIK ...
1990 Volume 43 Issue 5 Pages
456-461
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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A new antibiotic, MK4588, structurally related to xanthocillin, was isolated from the culture broth of
Leptosphaeria sp. L-179. Antibiotic MK4588 exhibited inhibitory activity against a limited range of Gram-positive and Gram-negative bacteria. The antibiotic was degraded by alkali to a more active product. The structures of MK4588 and the degradation product were determined to be (1
R*, 6
S*, 7
S*)-7-(
Z)-(1-isocyano-2-(4-methoxyphenyl))ethenyl-l-hydroxy-7-isocyanobicyclo[4, 2, 0]oct-2-en-4-one and (
Z)-2, 3-diisocyano-l-(4-methoxyphenyl)buta-l, 3-diene, respectively, by NMR spectral analyses coupled with X-ray crystallographic analysis of MK4588.
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I. SCREENING OF MICROORGANISMS, AND ISOLATION AND PHYSICO-CHEMICAL PROPERTIES OF EUROCIDINS C, D AND E
KAZUYA NAKAGOMI, MAKOTO TAKEUCHI, HIDEOKI TANAKA, NOBORU TOMIZUKA, TER ...
1990 Volume 43 Issue 5 Pages
462-469
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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Microorganisms producing anti-inflammatory substances were screened by the inhibitory effect on mast cell degranulation. Three new compounds related to pentaene macrolide eurocidins, eurocidins C, D and E, have been isolated from the culture broth of
Streptoverticillium eurocidicum IFO 13491 as the inhibitors. Their molecular weights and molecular formulae were estimated as 781.89 and C
39H
59NO
15 for eurocidin C, 795.92 and C
40H
61NO
15 for eurocidin D, and 779.92 and C
40H
61NO
14 for eurocidin E, respectively.
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II. STRUCTURE ELUCIDATION OF EUROCIDINS D AND E
KAZUYA NAKAGOMI, SHINICHI SAKAI, HIDEOKI TANAKA, NOBORU TOMIZUKA, YOSH ...
1990 Volume 43 Issue 5 Pages
470-476
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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The planar structures of new eurocidin related compounds, eurocidins D and E, were elucidated from
1H-
1H shift correlated 2D NMR spectra and other NMR data. All protons in the molecules were assigned. Eurocidins D and E have novel pentaenic structures of eurocidin family.
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MASAYA NAKAGAWA, YOICHI HAYAKAWA, KAZUO FURIHATA, HARUO SETO
1990 Volume 43 Issue 5 Pages
477-484
Published: May 25, 1990
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Variapeptin and citropeptin were found as novel hexadepsipeptide antibiotics produced by
Streptomyces variabilis and
Streptomyces flavidovirens, respectively. Their structures were elucidated by NMR spectral analysis including a variety of 2D techniques. Variapeptin and citropeptin are structurally related to azinothricin and A83586C, respectively.
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TOHRU YASUZAWA, YUTAKA SAITOH, HIROSHI SANO
1990 Volume 43 Issue 5 Pages
485-491
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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The structures of the new anthraquinone antitumor antibiotic DC92-B and its photodegradation product DC92-D were determined by their spectral studies. DC92-B and D are pluramycin antibiotics, related to hedamycin which possess a characteristic ring F and a side chain containing a
cis-epoxide and terminal dimethyl.
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I. STRUCTURAL STUDIES ON LANDOMYCINS A-D
THOMAS HENKEL, JÜRGEN ROHR, JOHN M. BEALE, LUDGER SCHWENEN
1990 Volume 43 Issue 5 Pages
492-503
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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The chemical structure of the new angucycline antibiotic landomycin A has been elucidated
via chemical and spectroscopic methods, in particular by 2D NMR correlation spectroscopy,
e.g.,
1H,
1H-COSY,
13C,
1H-COSY, correlation spectroscopy
via long-range-couplings and heteronuclear multiple bond connectivity spectroscopy sequences. The spectroscopic investigations were carried out principally with the octaacetyl derivative of landomycin A, which is more soluble in organic solvents than landomycin A itself. The structure consists of a new, unusual angucyclinone, landomycinone A, and of six deoxy sugars, four D-olivoses and two L-rhodinoses, which are all assembled in one chain thus forming the sequence (olivose-4→1-olivose-3-→-rhodinose)
2. This long sugar chain is bonded as a phenolic glycoside to the aglycone moiety, a unique structural feature among quinone glycoside antibiotics. By comparison with the main component landomycin A, the structures of three minor congeners, namely landomycins B, C and D, could be proposed.
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GUY T. CARTER, JEANNE A. NIETSCHE, DAVID R. WILLIAMS, DONALD B. BORDER ...
1990 Volume 43 Issue 5 Pages
504-512
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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A new family of antibacterial antibiotics has been isolated from
Micromonospora citrea. The compounds, designated citreamicins α, β, γ, ζ and η are of the polycyclic xanthone structure type. Their isolation, characterization and structure determination are presented.
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KOHJI KAWABATA, YOSHIKO INAMOTO, KAZUO SAKANE, TOSHIRO IWAMOTO, SEIJI ...
1990 Volume 43 Issue 5 Pages
513-518
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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The structure of FR109615, a new antifungal antibiotic, was determined to be (1
R, 2
S)-2-aminocyclopentane-l-carboxylic acid ((-)-
cis-2-ACPC:
8a) by X-ray analysis. (-)-
cis-2-ACPC (
8a) was also synthesized
via optical resolution of
3a and
3b derived from (±)-
cis-2-ACPC hydrochloride (
1).
8a showed potent antifungal activity, while its antipode (+)-
cis-2-ACPC (
8b) had no activity.
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MAKOTO SUNAGAWA, HARUKI MATSUMURA, TAKAAKI INOUE, MASATOMO FUKASAWA, M ...
1990 Volume 43 Issue 5 Pages
519-532
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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A series of new carbapenem compounds, which have a pyrrolidin-3'-ylthio group substituted with various aminocarbonyl group at C-5' position as C-2 side chain, have been prepared. The antibacterial activity and the stability to renal dehydropeptidase-I of these compounds were investigated, and the structure-activity relationships were discussed. In this series, SM-7338; (1
R, 5
S, 61
S)-2-[(3
S, 5
S)-5-dimethylaminocarbonylpyrrolidin-3-ylthio]-6-[(
R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (
5a) was the most interesting compound.
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HAJIME KAMACHI, MASAHISA OKA, YUKIO NARITA, SEIJI IIMURA, SHIMPEI ABUR ...
1990 Volume 43 Issue 5 Pages
533-543
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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The synthesis and antimicrobial activity of eight derivatives of 7-[(
Z)-2-(2-aminothiazol-4-yl)-and 7-[(
Z)-2-(5-amino-1, 2, 4-thiadiazol-3-yl)-2-methoxyiminoacetamido]cephalosporins having an (
E) or (
Z)-3-ammonio-1-propenyl group in the C-3 side chain are described. The (
E)-propenyl derivatives were more active than their corresponding
Z-isomers and showed well-balanced, broad antibacterial activity against both Gram-positive and Gram-negative bacteria including
Pseudomonas aeruginosa.
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IV. SYNTHESIS AND BIOLOGICAL PROPERTIES OF 6-O-METHYLERYTHROMYCIN B
SHIGEO MORIMOTO, TAKASHI ADACHI, YOKO MISAWA, TAKATOSHI NAGATE, YOSHIA ...
1990 Volume 43 Issue 5 Pages
544-549
Published: May 25, 1990
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6-
O-Methylerythromycin B has been synthesized from erythromycin B
via regioselective methylation of the 6-hydroxyl group in 71 % overall yield. This compound shows
in vitro antibacterial activity comparable to erythromycins A and B and exhibits superior
in vivo activity with improved pharmacokinetic properties.
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VALERIE M. GOOD, MICHAEL N. GWYNN, DAVID J. C. KNOWLES
1990 Volume 43 Issue 5 Pages
550-555
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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MM 45289 (A82846A, eremomycin), a glycopeptide antibiotic of the vancomycin type, was confirmed to have improved antibacterial activity over vancomycin. However its affinity (
Ka) for the target site peptide mimetic diacetyl-L-lysyl-D-alanyl-D-alanine (DALAA) was 23-fold lower. Concentrations of DALAA required to reverse the antibacterial activity of MM 45289 were in the order of 10 to 50-fold higher than for vancomycin. These results have implications for both mode of action studies and mechanism-based screening strategies for this class of antibiotic.
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SETSUKO KUNIMOTO, KEIKO KOMURO, CHISATO NOSAKA, TSUTOMU TSUCHIYA, SHUN ...
1990 Volume 43 Issue 5 Pages
556-565
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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From various new anthracyclines containing fluorine in their sugar moieties, 7-
O-(2, 6-dideoxy2-fluoro-α-L-talopyranosyl)adriamycinone-14-hemipimerate (FAD 104) has been selected for clinical investigation, because of its excellent antitumor activity and solubility. In this paper, the mechanism whereby FAD 104 exhibits good antitumor activity
in vivo was studied through experiments
in vitro in comparision with doxorubicin (DOX). FAD 104 had weaker activity than DOX in DNA single and double strand scission in P388 cells and in binding to calf thymus DNA. FAD 104 was taken up by P388 cells faster than DOX. The ester linkage in FAD 104 was gradually hydrolyzed at neutral pH. FAD 104 was metabolized to 7-
O-(2, 6-dideoxy-2-fluoro-α-L-talopyranosyl)adriamycinone (FT-ADM) when incubated with mouse or human serum. In mouse serum the esterase activity was about 100 times higher than in human serum. The product of nonenzymatic and enzymatic esterolysis, FT-ADM, was rapidly taken up by P388 cells and accumulated, reaching at a 9.7-fold higher level than DOX. Thus FAD 104 was less active than DOX in itself, but it showed much higher activity through conversion into FT-ADM, due to the action of esterase or to spontaneous and gradual hydrolysis at physiological pH. 7-
O-(2, 6-Dideoxy-2-fluoro-α-L-talopyranosyl)adriamycinol (FT-ADM-OH), another metabolite found in mouse serum had the least biological activity among the fluorine-containing anthracycline glycosides, but its activity was still higher than DOX.
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V. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 4''-O-METHYL DERIVATIVES OF ERYTHROMYCIN A 11, 12-CYCLIC CARBONATE
SHIGEO MORIMOTO, YOKO MISAWA, HIDEAKI KONDOH, YOSHIAKI WATANABE, SADAF ...
1990 Volume 43 Issue 5 Pages
566-569
Published: May 25, 1990
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VI. STRUCTURE AND ANTIBACTERIAL ACTIVITY OF ACID DEGRADATION PRODUCTS OF 6-O-METHYLERYTHROMYCINS A
SHIGEO MORIMOTO, YOKO MISAWA, TOSHIFUMI ASAKA, HLDEAKI KONDOH, YOSHIAK ...
1990 Volume 43 Issue 5 Pages
570-573
Published: May 25, 1990
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DESMOND J. BEST, GEORGE BURTON, DAVID T. DAVIES, JOHN S. ELDER, TERENC ...
1990 Volume 43 Issue 5 Pages
574-577
Published: May 25, 1990
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HIROTADA YAMADA, SHINJI UEDA, MASAYUKI MUTOH, HIDEO NAGATA, HIROSHI NO ...
1990 Volume 43 Issue 5 Pages
578-583
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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KUNIO ISSHIKI, TSUTOMU SAWA, HIROSHI NAGANAWA, SEIKO HATTORI, TAKAKO I ...
1990 Volume 43 Issue 5 Pages
584-585
Published: May 25, 1990
Released on J-STAGE: April 19, 2006
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