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FIVE NOVEL METABOLITES RELATED TO BENZ[A]ANTHRACENE FROM AN UNIDENTIFIED ACTINOMYCETE DESIGNATED X-14881
HUBERT MAEHR, CHAO-MIN LIU, MARK LIU, AGOSTINO PERROTTA, JOANNE M. SMA ...
1982 Volume 35 Issue 12 Pages
1627-1631
Published: 1982
Released on J-STAGE: April 12, 2006
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Five metabolites of actinomycete X-14881 were isolated from the fermentation broth and characterized. The major component was identified as [3
R-(3α, 6aβ, 7β, 12α, 12aα)] or [3
S-(3β, 6aα, 7α, 12β, 12aβ)]-6a, 7, 12-trihydroxy-3, 4, 6a, 7, 12, 12a-hexahydro-8-methoxy-3-methylbenz[a]- anthracen-1(2
H)-one; the other four are closely related derivatives thereof.
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SATOSHI OMURA, HIDEKI SHIMIZU, YUZURU IWAI, KIYOIZUMI HINOTOZAWA, KAZU ...
1982 Volume 35 Issue 12 Pages
1632-1637
Published: 1982
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A novel antibiotic, AM-2604 A was isolated from the fermentation broth of
Streptomyces sp. AM-2604 by solvent extraction and silica gel column chromatography. The antibiotic is pale yellow needles possessing UV absorption maxima at 280 nm and 330 nm (sh). The antibiotic possesses weak activity against fungi and trichomonad and potent inhibitory activity against various RNA and DNA viruses
in vitro.
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KLAUS ECKARDT, DIETER TRESSELT, WOLFGANG IHN, GERTRAUD BRADLER, G. REI ...
1982 Volume 35 Issue 12 Pages
1638-1640
Published: 1982
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Sarubicin B, isolated from the culture filtrate of a
Streptomyces strain JA 2861, is a new quinone antibiotic. The compound was isolated as an orange crystalline powder, mp 282-284°C.
In vitro sarubicin B was found to inhibit Gram-positive bacteria. It was not active against Gram-negative microorganisms.
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HIROYASU TORE, AKIHIRO YOSHIMOTO, TOMOYUKI ISHIKURA, HIROSHI NAGANAWA, ...
1982 Volume 35 Issue 12 Pages
1641-1645
Published: 1982
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Two blocked mutants of the aclacinomycin-producing
Streptomyces galilaeus MA144-M1 produced new anthraquinones and anthracyclinones. The mutant ANR-58 produced compounds 58A, 58B, 58C (7-deoxy-2-hydroxyaklavinone), 58D (2-hydroxyaklavinone) and 58WR. All these compounds have the 2-hydroxyl group. The mutant ANR-665 produced compounds 665A and 665B. The compounds 58A, 58B and 665A have an anthraquinone skeleton.
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JUN'ICHI SHOJI, HIROSHI HINOO, RYUZI SAKAZAKI, TOSHIYUKI KATO, KOICHI ...
1982 Volume 35 Issue 12 Pages
1646-1650
Published: 1982
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N-Acetylisopenicillin N was isolated from the culture broth of
Streptomyces tokunonensis sp. nov., and identified from
1USH NMR spectroscopy and release of L-α-aminoadipic acid by acid hydrolysis. In the course of this study, the specimen of penicillin N isolated from this strain was proved to contain a small amount of isopenicillin N by HPLC.
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H. A. KIRST, G. G. MARCONI, F. T. COUNTER, P. W. ENSMINGER, N. D. JONE ...
1982 Volume 35 Issue 12 Pages
1651-1657
Published: 1982
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A novel low-molecular weight inhibitor of an aminoglycoside-inactivating enzyme, initially isolated from fermentation broths of
Streptomyces neyagawaensis, was determined to be 7-hydroxytropolone. Its structure was confirmed by synthesis.
In vitro synergy was demonstrated between 7-hydroxytropolone and certain aminoglycosides against bacteria which were resistant to those aminoglycosides by virtue of a 2"-
O-adenylyltransferase. The synthesis and characterization of some analogs of 7-hydroxytropolone is also described.
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RICHARD C. THOMAS, CONNIE G. CHIDESTER
1982 Volume 35 Issue 12 Pages
1658-1664
Published: 1982
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The structure and absolute configuration of the macrolide antibiotic albocycline (
1a) has been determined by X-ray crystallographic analysis on the derived
p-bromobenzoate (
1b). The absolute configuration of albocycline is 4
R, 7
S, 12
S, 13
R.
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HIROYUKI IWASAWA, SHINICHI KONDO, DAISHIRO IKEDA, TOMIO TAKEUCHI, HAMA ...
1982 Volume 35 Issue 12 Pages
1665-1669
Published: 1982
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The method for chemical modification of spergualin with retention of the configuration at the C-11 has been achieved by the use of tetrahydropyranyl group for protection of the 11-hydroxyl group. (-)-15-Deoxyspergualin (
2), which shows about eight times stronger inhibition against mouse leukemia L-1210 than the natural (-)-spergualin (
1), and (-)-spergualin-15-phosphate (
3) possessing a good antitumor activity have been synthesized starting from
1.
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KAZUMICHI UOTANI, HIROSHI NAGANAWA, TAKAAKI AOYAGI, HAMAO UMEZAWA
1982 Volume 35 Issue 12 Pages
1670-1674
Published: 1982
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Biosynthetic pathways of ebelactone A and B were studied by
13C NMR spectroscopy. By using
13C labeled compounds as precursors it was determined that ebelactone A was derived from one molecule of acetic acid and six propionic acids and ebelactone B from one molecule of acetic acid, five propionic acids and one butyric acid.
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H. A. KIRST, G. M. WILD, R. H. BALTZ, R. L. HAMILL, J. L. OTT, F. T. C ...
1982 Volume 35 Issue 12 Pages
1675-1682
Published: 1982
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Although a substantial number of 16-membered macrolides related to tylosin have now been isolated and evaluated as antibiotics, none appeared to be superior to tylosin in treating bacterial or mycoplasmal infections caused by sensitive organisms. Nevertheless, this comparison of the antibiotic activity of 16-membered macrolides clearly indicates that novel antibiotics with potentially useful activity can be obtained from mutant strains which have been blocked at various steps in their biosynthesis of antimicrobial agents. The novel compounds thus produced may also be used as starting materials for additional chemical and microbiological modification. Furthermore, the mutant strains which produced these novel compounds should be useful recipients for interspecific genetic recombination by protoplast fusion or gene cloning to yield hybrid antibiotics.
1, 2) Even greater exploitation of these methods will be required in the continuing search for new antibiotics and improved methods for producing them.
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ROLE OF PENICILLIN-BINDING PROTEINS IN PENICILLIN RESISTANT MUTANTS
HISAYOSHI NAKAZAWA, HIROSHI OGAWARA
1982 Volume 35 Issue 12 Pages
1683-1691
Published: 1982
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Several mutants isolated after
N-methyl-
N'-nitro-
N-nitrosoguanidine mutagenesis of
Streptomyces cacaoi strain KCC S-0352, were resistant to benzylpenicillin ranging in concentration from 1, 000 to 5, 000 μg/ml (4- to 20-fold more resistant than the parent). These mutants also acquired resistance to mecillinam, cephamycin C and methicillin. The affinity for beta;-lactams of penicillin-binding proteins (including PBP-2-a possible lethal target of beta;-lactams in
Streptomyces cacaoi) in the mutants decreased. Addition of Triton X-100 or ethylenediaminetetraacetic acid, but not toluene, reduced the minimum inhibitory concentration of beta;-lactams.
In vitro accessibility of [
14C]benzylpenicillin to whole cells and membrane fractions was lower in the mutants than in the parent. The binding of beta;-lactams to penicillin-binding proteins in both the parent and mutants was increased by pretreatment with Triton X-100 or ethylenediaminetetraacetic acid. The results of this study of penicillin-binding suggest that penicillin-binding proteins play a major role in "acquired" resistance as well as "intrinsic" resistance.
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AKIHITO YAMAGUCHI, RYOICHI HIRUMA, TETSUO SAWAI
1982 Volume 35 Issue 12 Pages
1692-1699
Published: 1982
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Liposomes containing penicillinase or cephalosporinase were prepared from the phospholipids of
Escherichia coli. After free β-lactamase was inactivated by clavulanic acid or penicillanic acid sulfone followed by separation of inactivated enzyme and inhibitor from liposomes by gel filtration, the permeability of these liposomes to ampicillin, cefazolin and cephaloridine was estimated by measuring the hydrolysis of these antibiotics by the entrapped enzymes. The permeability parameter C (minute
-1 μM lipid
-1) of ampicillin, cefazolin and cephaloridine was calculated to be 2.35×10
-4, 0.33×10
-4 and 0.52×10
-4, respectively. The lipid bilayer permeability of these antibiotics was also measured by using the liposomes containing these antibiotics. About half of the initially entrapped ampicillin was released from the liposomes within 80 minutes, while no significant release of cefazolin and cephaloridine could be detected during the same period. These results clearly indicates that the lipid bilayer membrane is more permeable to ampicillin than cefazolin and cephaloridine, and they are consistent with the observations of SAWAI
et al.
1), who showed that ampicillin was a more effective antibacterial drug than cefazolin and cephaloridine against the porin-deficient mutants.
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REIKO KARIYAMA
1982 Volume 35 Issue 12 Pages
1700-1704
Published: 1982
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Effect of antibiotics affecting cell wall synthesis on phospholipid composition in
Staphylococcus aureus 209P was examined. Each antibiotic was added in the middle exponential growth phase and the growth was followed turbidimetrically. Penicillin, fosfomycin, cycloserine, moenomycin and cefazolin caused a leveling off of turbidity and growth to cease with-out lysis. Enramycin and bacitracin were bacteriolytic. Bacteriolytic antibiotics caused a greater increase of cardiolipin content than those that were non-bacteriolytic. The amount of phosphatidylglycerol decreased in proportion to the increment of cardiolipin content. Since bacteriolytic antibiotics bind to undecaprenol, the role of cardiolipin was discussed in relation to the mechanism of synthesis of cell surface materials.
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VINCENT P. GULLO, SHELDON B. ZIMMERMAN, RAY S. DEWEY, OTTO HENSENS, PA ...
1982 Volume 35 Issue 12 Pages
1705-1707
Published: 1982
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TAKEMITSU ASAOKA, KATSUKIYO YAZAWA, YUZURU MIKAMI, TADASHI ARAI, KATSU ...
1982 Volume 35 Issue 12 Pages
1708-1710
Published: 1982
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AKIRA TERAHARA, TATSUO HANEISHI, MAMORU ARAI, TADASHI HATA, HARUMITSU ...
1982 Volume 35 Issue 12 Pages
1711-1714
Published: 1982
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HIROYUKI IWASAWA, DAISHIRO IKEDA, SHINICHI RONDO, HAMAO UMEZAWA
1982 Volume 35 Issue 12 Pages
1715-1718
Published: 1982
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1. INCORPORATION OF 13C-AND 2H-LABELED PRECURSORS INTO BIALAPHOS
HARUO SETO, SATOSHI IMAI, TAKASHI TSURUOKA, ATUYUKI SATOH, MICHIO KOJI ...
1982 Volume 35 Issue 12 Pages
1719-1721
Published: 1982
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U. GRÅFE, W. SCHADE, I. ERITT, W. F. FLECK, L. RADICS
1982 Volume 35 Issue 12 Pages
1722-1723
Published: 1982
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JUNKO NISHIKAWA, KAZUO TORI, MAMORU TAKASUKA, HIROSHI ONOUE, MASAYUKI ...
1982 Volume 35 Issue 12 Pages
1724-1728
Published: 1982
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MAMORU TAKASUKA, JUNKO NISHIKAWA, KAZUO TORI
1982 Volume 35 Issue 12 Pages
1729-1733
Published: 1982
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