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I. TAXONOMY OF THE PRODUCING ORGANISM, FERMENTATION, ISOLATION AND BIOLOGICAL ACTIVITY
CHRISTOPHER M. M. FRANCO, JULIA N. GANDHI, SUGATA CHATTERJEE, BIMAL N. ...
1987 Volume 40 Issue 10 Pages
1361-1367
Published: October 25, 1987
Released on J-STAGE: April 19, 2006
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A new macrolide antibiotic, swalpamycin, has been isolated from the culture broth of
Streptomyces sp. Y-84, 30967. Taxonomically the producing organism most closely resembles
Streptomyces anandii and has therefore been named
S. anandii subsp.
swalpus. Swalpamycin is a neutral 16-membered macrolide active against Gram-positive bacteria including erythromycin-resistant strains.
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II. STRUCTURE ELUCIDATION
SUGATA CHATTERJEE, GOUKANAPALLI C. S. REDDY, CHRISTOPHER M. M. FRANCO, ...
1987 Volume 40 Issue 10 Pages
1368-1374
Published: October 25, 1987
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A new antibiotic swalpamycin (
1) has been isolated from the culture broth of
Streptomyces sp. Y-84, 30967. The antibiotic has the molecular formula of C
37H
56O
14 and belongs to the class of 16-membered neutral macrolide antibiotics. Its structure has been elucidated by an analysis of its spectral properties. It contains a novel aglycone herein called swalpanolide.
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I. TAXONOMY, FERMENTATION AND BIOLOGICAL PROPERTIES
MARIANNA JACKSON, JAMES P. KARWOWSKI, ROBERT J. THERIAULT, PRABHAVATHI ...
1987 Volume 40 Issue 10 Pages
1375-1382
Published: October 25, 1987
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Coloradocin was discovered in a screen for anti-anaerobe activity. The producing organism was determined to be a new species of
Actinoplanes, designated
Actinoplanes coloradoensis sp. nov. Coloradocin inhibits
Bacteroides,
Clostridium and other anaerobes. It does not inhibit most aerobic bacteria but is effective against
Neisseria gonorrhoeae and
Haemophilus influenzae. Coloradocin has low acute toxicity.
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II. IDENTITY WITH LUMINAMICIN AND ELUCIDATION OF STRUCTURE
RONALD R. RASMUSSEN, MICHAEL H. SCHERR, DAVID N. WHITTERN, ALEX M. BUK ...
1987 Volume 40 Issue 10 Pages
1383-1393
Published: October 25, 1987
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Coloradocin was isolated from a fermentation broth by adsorption onto Amberlite XAD-2. The activity was eluted in MeOH and purified by gel filtration on Shephadex LH-20, followed by liquid-liquid chromatography on diol-bonded silica gel. The last two steps in the purification of this antibiotic included reverse-phase chromatography on CIS-bonded silica gel and countercurrent chromatography on an Ito Coil Planet Centrifuge to give material of 90% purity. Analytically pure material was obtained by preparative HPLC. As a result of extensive homo and heteronuclear two-dimensional NMR studies, a structure was proposed for coloradocin. The structure consists of a decalin ring system fused to a 10-membered macrolactone which in turn is fused to a 14-membered macrolactone possessing an enol ether in conjugation with an unsaturated cyclic anhydride functionality. Coloradocin is related to a small class of antibiotics which include nodusmicin and nargenicin and was shown to be identical to luminamicin for which no structure has been reported.
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I. TAXONOMY, FERMENTATION, ISOLATION AND CHARACTERIZATION
MOTOAKI NISHIKAWA, YASUHISA TSURUMI, TAKAYUKI NAMIKI, KEIZO YOSHIDA, M ...
1987 Volume 40 Issue 10 Pages
1394-1399
Published: October 25, 1987
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WF-3681 was isolated from a cultured filtrate of
Chaetomella raphigera as a novel inhibitor of aldose reductase. It was extracted with ethyl acetate and then purified with silica gel chromatography. Its molecular formula was determined to be C
13H
12O
5 by elemental analysis and high resolution electron impact mass spectrometry. IC
50 of WF-3681 was 2.5×10
-7 M for partially purified aldose reductase of rabbit lens.
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II. STRUCTURE DETERMINATION AND SYNTHESIS
TAKAYUKI NAMIKI, MOTOAKI NISHIKAWA, YOSHIKUNI ITOH, ITSUO UCHIDA, MASA ...
1987 Volume 40 Issue 10 Pages
1400-1407
Published: October 25, 1987
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The structure of WF-3681, a novel aldose reductase inhibitor produced by
Chaetomella raphigera Swift No. 3681, was deduced to be
1 on the basis of its spectroscopic and chemical evidences and confirmed by a total synthesis starting from (
E)-5-phenyl-4-pentenol.
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FERMENTATION, ISOLATION AND STRUCTURE ELUCIDATION
MAHESH PATEL, VINCENT P. GULLO, VINOD R. HEGDE, ANN C. HORAN, FRANK GE ...
1987 Volume 40 Issue 10 Pages
1408-1413
Published: October 25, 1987
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A novel tetracycline antibiotic, Sch 33256, was isolated from a culture broth of a new species of
Actinomadura. The antibiotic was isolated by solvent extraction, Sephadex G-25 column chromatography and crystallization. The structure was determined by comparison of the spectra with that of chlortetracycline. Spectroscopic analysis of the compound yielded 2'-
N-methyl-8-methoxychlortetracycline as the proposed structure.
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FERMENTATION, ISOLATION AND STRUCTURE ELUCIDATION
MAHESH PATEL, VINCENT P. GULLO, VINOD R. HEGDE, ANN C. HORAN, JOSEPH A ...
1987 Volume 40 Issue 10 Pages
1414-1418
Published: October 25, 1987
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An actinomycete identified as a
Dactylosporangium sp. produces a new tetracycline, 4ahydroxy-8-methoxychlortetracycline (Sch 34164). The addition of magnesium ions to complex fermentation media increased the antibiotic titers. Sch 34164 was isolated by solvent extraction and Sephadex G-25 column chromatography. The novel structure was proposed based on spectroscopic analysis. The shift of C-4a (35 to 77 ppm) and C-8 (140 to 163 ppm) in the
13C NMR as compared to chlortetracycline was indicative of the novel hydroxyl and methoxy substituents, respectively.
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ISOLATION OF A THIRD 8-METHOXY SUBSTITUTED CHLORTETRACYCLINE
ELIZABETH B. SMITH, HANAN K. MUNAYYER, MICHAEL J. RYAN, B. ALLEN MAYLE ...
1987 Volume 40 Issue 10 Pages
1419-1425
Published: October 25, 1987
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Actinomadura brunnea produces 2'-
N-methyl-8-methoxychlortetracycline. A derivative of this strain has been isolated that is specifically blocked in methylation of the 2'-amino position. This isolate was detected by screening approximately 30, 000 colonies of a mutagenized population of
Actinomadura brunnea using a direct soft agar overlay with an
Escherichia coli indicator. The antibiotic produced by the blocked mutant has been identified as 8-methoxychlortetracycline (Sch 36969) based upon its biological activity, relative mobility on TLC and HPLC, and spectroscopic data.
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A. CACCIAPUOTI, E. L. Moss, F. MENZEL, C. ADAM CRAMER, W. WEISS, D. LO ...
1987 Volume 40 Issue 10 Pages
1426-1430
Published: October 25, 1987
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The
in vitro activities of three new 8-methoxychlortetracyclines, Sch 36969, 33256 and 34164 were compared to tetracycline, minocycline and doxycycline. Against aerobic Gramnegative rods Sch 36969 had a geometric mean MIC (GMM) of 4.2 μg/ml, about 8-fold more potent than Sch 33256, and similar to all the other compounds. Sch 36969 also had good activity against methicillin-resistant (GMM, 0.21 μg/ml) and -susceptible Staphylococci (GMM, 0.14 μg/ml), Streptococci (GMM, 0.06 μg/ml), and most anaerobic bacteria (GMM, <0.5 μg/ml). In general, Sch 36969 was similar to, or more potent than, all the other compounds tested. Serum levels of Sch 36969 in squirrel monkeys were 4-fold lower (AUC, 4.5 μg•hours/ml) than those of chlortetracycline (AUC, 16.1 μg•hours/ml). In mouse protection tests (PD
50s) against various strains of bacteria, Sch 36969 was similar in activity to tetracycline, but up to 6-fold less active than chlortetracycline. The structure activity relationships for these new chlortetracyclines are described.
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BACIMETHRIN ISOLATED FROM STREPTOMYCES ALBUS IDENTIFICATION, DERIVATIVES, SYNTHESIS AND BIOLOGICAL PROPERTIES
HANNELORE DRAUTZ, WERNER MESSERER, HANS ZÄHNER, SABINE BREIDING-M ...
1987 Volume 40 Issue 10 Pages
1431-1439
Published: October 25, 1987
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Bacimethrin (
1), known as a thiamine antagonist produced by
Bacillus megatherium, was isolated from
Streptomyces albus and has been further characterized by NMR spectra and acetylation. A new easy three step synthesis for
1 is described. The biological activity of
1, and its mode of action were discussed. There are indications that bacimethrin inhibits the phosphorylation of 4-amino-5-hydroxymethyl-2-methylpyrimidme (Pyr-OH) during thiamine biosynthesis.
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TAICHI MANOME, EMIKO HOSHINO
1987 Volume 40 Issue 10 Pages
1440-1447
Published: October 25, 1987
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The thiostrepton-resistance gene is expressed in
Streptomyces jumonjinensis [16]-8 SANK 61185 carrying the plasmid pIJ702 but not the tyrosinase gene. We have isolated DNA fragments from various streptomycetes that restore expression of the tyrosinase gene on pIJ702 in this organism. The nucleotide sequences of two of these DNA fragments show that they contain putative ribosome binding sites and -10 regions of possible promoters.
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KYUICHI NEMOTO, MICHIKO HAYASHI, JUNPEI ITO, FUMINORI ABE, TOMOHISA TA ...
1987 Volume 40 Issue 10 Pages
1448-1451
Published: October 25, 1987
Released on J-STAGE: April 19, 2006
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We investigated the effect of spergualin (SGL) upon the development of spontaneous systemic lupus erythematosus-like lesions in male MRL/MpJ-lpr/lpr mice. SGL was administered ip at doses of 2.5, 5 and 10 mg/kg to two groups of mice. One group received SGL prophylactically from 7 to 21 weeks of age. The other group received SGL curatively from 13 to 27 weeks of age. The occurrence of lupus lesions was characterized by enlarged lymphoid organs, high anti-DNA titer and blood urea nitrogen, and severe glomerular nephritis. In both groups these characteristics were significantly suppressed by SGL in a dosedependent manner. This inhibitory activity was greatest at a dose of 10 mg/kg. These findings suggest that SGL has prophylactic and curative effects against lupus lesions in autoimmune disease in mice.
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ICHIHIKO YAMAMOTO, MASAYA NAKAGAWA, YOICHI HAYAKAWA, KAZUYOSHI ADACHI, ...
1987 Volume 40 Issue 10 Pages
1452-1454
Published: October 25, 1987
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HUBERT MAEHR, RALPH H. EVANS
1987 Volume 40 Issue 10 Pages
1455-1456
Published: October 25, 1987
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HIROSHI TOMODA, KAZUAKI IGARASHI, YOSHITAKE TANAKA, SATOSHI OMURA
1987 Volume 40 Issue 10 Pages
1457-1460
Published: October 25, 1987
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KUNIO ISSHIKI, YOSHIKAZU TAKAHASHI, HIRONOBU IINUMA, HIROSHI NAGANAWA, ...
1987 Volume 40 Issue 10 Pages
1461-1463
Published: October 25, 1987
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TAKAYUKI USUI, SUMIO UMEZAWA
1987 Volume 40 Issue 10 Pages
1464-1467
Published: October 25, 1987
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YOSHIO HAMASHIMA, TADATOSHI KUBOTA, KYOJI MINAMI, KOJI ISHIKURA, TOSHI ...
1987 Volume 40 Issue 10 Pages
1468-1470
Published: October 25, 1987
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MASAYA IMOTO, KAZUO UMEZAWA, KUNIO ISSHIKI, SETSUKO KUNIMOTO, TSUTOMU ...
1987 Volume 40 Issue 10 Pages
1471-1473
Published: October 25, 1987
Released on J-STAGE: April 19, 2006
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