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KATSUKIYO YAZAWA, KATSUHIRO TAKAHASHI, YUZURU MIKAMI, TADASHI ARAI, NA ...
1986 Volume 39 Issue 12 Pages
1639-1650
Published: 1986
Released on J-STAGE: April 19, 2006
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A new series of saframycins Y3, Yd-1, Yd-2, Ad-1, Y2b and Y2b-d was produced by directed biosynthesis employing resting cells of saframycin producer,
Streptomyces lavendulae No. 314. Their structures were determined by comparison with the spectral data of UV, IR, and
1H and
13C NMR of saframycin A, whose structure has already been established. Saframycin Y3 is 25-deoxy-25-aminosaframycin A, while saframycin Yd-1 is 26-homosaframycin Y3, and saframycin Y2b is a dimer of saframycin Y3. Saframycin Ad-1 is 26-homosaframycin A. Saframycin Yd-2 is 26-demethylsaframycin Y3, and saframycin Y2b-d is a dimmer of saframycin Yd-1.
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T. R. HURLEY, R. H. BUNGE, N. E. WILLMER, G. C. HOKANSON, J. C. FRENCH
1986 Volume 39 Issue 12 Pages
1651-1656
Published: 1986
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The isolation and characterization of the title antibiotics, which are produced by the same
Streptomyces sp., is described. The potent antitumor agent, PD 124, 895, is an analog of hydroxyelactocin (PD 114, 721). PD 124, 966 is a new member of the depsipeptide family of antibiotics.
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I. ISOLATION, CHARACTERIZATION AND BIOLOGICAL PROPERTIES
HANNELORE DRAUTZ, HANS ZÄHNER, JÜRGEN ROHR, AXEL ZEECK
1986 Volume 39 Issue 12 Pages
1657-1669
Published: 1986
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The colored urdamycins A to F, six new angucycline antibiotics produced by
Streptomyces fradiae strain Tü 2717, were detected by chemical screening. They are biologically active against Gram-positive bacteria and stem cells of murine L1210 leukemia. The urdamycins are glycosides and differ in their aglycones, which can be liberated by acidic hydrolysis besides the sugars D-olivose and L-rhodinose. The structure of the main compound, urdamycin A (3b), follows from the spectroscopic and chemical data in connection with an X-ray analysis. The aglycone urdamycinone A (3a) is identical with aquayamycin. The structures of urdamycin B (4b), E (3c), F and partial structures of urdamycin C and D, will be presented in a subsequent paper. The new term "angucycline/angucyclinone" is used for an increasing group of related antibiotics.
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AKIRA ENDO, DAISUKE KOMAGATA, HIDEAKI SHIMADA
1986 Volume 39 Issue 12 Pages
1670-1673
Published: 1986
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Monacolin M, a new specific inhibitor of cholesterol biosynthesis structurally related to monacolin K (mevinolin), was isolated from cultures of a strain of
Monascus ruber. The structure of monacolin M was determined to be β-hydroxybutyryl ester of monacolin J by a combination of physical techniques. It was suggested that monacolin M is derived from monacolin J
via a synthetic pathway distinct from that for the synthesis of monacolin K, α-methylbutyryl ester of monacolin J. The inhibitory effect of monacolin M on β-hydroxy-β-methylglutaryl-CoA reductase was slightly lower than that of monacolin K.
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I. TAXONOMY, FERMENTATION, ISOLATION AND CHARACTERIZATION
SUSUMU SANO, KATSUSHIGE IKAI, HIROYUKI KURODA, TERUYA NAKAMURA, AKIRA ...
1986 Volume 39 Issue 12 Pages
1674-1684
Published: 1986
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New aminopeptidase B inhibitors that we named OF4949-
I, II, III and
IV were isolated from the culture broth of a fungus,
Penicillium rugulosum OF4949. The molecular formula of
I was C
23H
26N
4O
8 and that of
II, C
22H
24N
4O
8, judging from elemental analysis and secondary ion mass spectrometry. The concentrations of
I, II, III and
IV required for 50% inhibition of aminopeptidase, using Ehrlich ascites carcinoma cells as the source of the enzyme, were 0.0054, 0.0048, 3.4 and 1.7 μg/ml, respectively. Components
I and
II augmented delayed-type hypersensitivity in mice to sheep red blood cells.
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II. ELUCIDATION OF STRUCTURE
SUSUMU SANO, KATSUSHIGE IKAI, KAORU KATAYAMA, KAZUTOH TAKESAKO, TERUYA ...
1986 Volume 39 Issue 12 Pages
1685-1696
Published: 1986
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The structures of OF4949-
I, II, III and
IV were identified by analysis of the products of their chemical degradation and by
1H NMR,
13C NMR, and mass spectrometry. These compounds were new cyclic peptides containing diphenyl ether as a chromophore. OF4949-
I had two amino acids, β-hydroxy-L-asparagine and 4-methylisodityrosine. The structural differences between
I and
II and between
III and
IV lay solely in the diphenyl ether moiety; the phenolic hydroxyl group in
II and
IV was methylated in
I and
III. OF4949-
III and
IV contained L-asparagine instead of the β-hydroxy-L-asparagine moiety of
I and
II.
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III. BIOSYNTHESIS
SUSUMU SANO, MITSUHIRO UENO, KAORU KATAYAMA, TERUYA NAKAMURA, AKIRA OB ...
1986 Volume 39 Issue 12 Pages
1697-1703
Published: 1986
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To elevate production of OF4949 by
Peuicillium rugulosum OF4949 and to elucidate the pathway of its biosynthesis, mutants were selected on the basis of their resistance to growth inhibition by phenylalanine analogs. A mutant resistant to
m-fluorophenylalanine, strain No. M414, had 3-fold the production of the parent. In a study of the biosynthesis of OF4949-I and II, several
14C-labeled compounds were examined as possible precursors of OF4949. L-[
14C]Tyrosine and L-[
14C]asparagine were incorporated efficiently. Most of the radioactivity of L-[
14C]tyrosine was found in the 4-methylisodityrosine (
B2) or isodityrosine (
B1) moieties, and that of L-[
14C]asparagine was in the β-hydroxyasparagine moiety.
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JOHN W. WESTLEY, CHAO-MIN LIU, JOHN F. BLOUNT, LOUIS TODARO, LILIAN H. ...
1986 Volume 39 Issue 12 Pages
1704-1711
Published: 1986
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Streptomyces sp. X-14873 (ATCC 31679) has been found to produce a number of secondary metabolites. Three have been identified as the novel actinomycins, X-14873B, C and D, each of which contains both proline and 3-hydroxy-5-methylproline. Potentially, the most important microbial product from this fermentation is the novel polyether antibiotic X-14873A (
1) which differs from lysocellin (
5) only in the substituents at carbons C-4 and C-5 in the tetrahydropyranyl ring. The methyl group and proton in lysocellin are replaced by an ethyl and hydroxyl group, respectively in X-14873A. In addition, two other novel polyethers, X-14873H (
2) and G (
3), were isolated and shown to differ from 1 in lacking a carboxyl group and in the case of 3, possessing an ether bridge across the terminal tetrahydrofuranyl ring system.
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CHAO-MIN LIU, JOHN W. WESTLEY, T. E. HERMANN, B. LA T. PROSSER, N. PAL ...
1986 Volume 39 Issue 12 Pages
1712-1718
Published: 1986
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Novel polyether antibiotics X-14873A, X-14873G, and X-14873H are produced by the fermentation of
Streptomyces sp. X-14873 (ATCC 31679). This report presents taxonomic studies and fermentation conditions for the antibiotic producing culture. The antibiotics are mainly active against Gram-positive bacteria. The ionophore properties of X-14873A are also characterized.
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PRISKA SPIRI-NAKAGAWA, YUKIKO FUKUSHI, KAZUNORI MAEBASHI, NOBUTAKA IMA ...
1986 Volume 39 Issue 12 Pages
1719-1723
Published: 1986
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In the course of screening for new high molecular weight peptidoglycan synthesis inhibitors, izupeptins A and B, antibiotics active against Gram-positive bacteria including methicillin-resistant Staphylococci and
Clostridium were discovered. The antibiotics were found to be new members of the glycopeptide antibiotic family, namely of the vancomycin type, based on chemical and spectroscopic data. The molecular weight of izupeptin A was determined to be 1, 475 by SI (secondary ion)-MS (integer molecular weight, 1, 473), and it contains two chlorine atoms.
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H. A. KIRST, M. DEBONO, K. E. WILLARD, B. A. TRUEDELL, J. E. TOTH, J. ...
1986 Volume 39 Issue 12 Pages
1724-1735
Published: 1986
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A large group of ester derivatives of tylosin-related macrolides was prepared in which the hydroxyl groups at C-3 and C-4" were acylated by either chemical or biochemical methods. Most of the derivatives exhibited excellent
in vitro antimicrobial activity. However, only the 3, 4"-diacyl derivatives of tylosin and macrocin showed any significant improvements of
in vivo efficacy against experimental infections in rodents.
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MASAAKI ISHIZUKA, TORU MASUDA, SHIGETOSHI MIZUTANI, MICHIYO OSONO, HIR ...
1986 Volume 39 Issue 12 Pages
1736-1743
Published: 1986
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Spergualin and its analog, 15-deoxyspergualin showed a marked antitumor effect against L1210 by intraperitoneal and oral administrations. After treatment with these substances 40- or 60-day survivors (cured mice of L1210) were resistant to reinoculation of L1210 cells. They were resistant only to L1210. The antitumor effector cells in these mice were determined to be T cells. NK activity of spleen cells was also enhanced by spergualins. The antitumor activity of 15-deoxyspergualin was markedly reduced in immuno-deficient mice. IL (interleukin)-2 production, but not IL-1, was enhanced in supernatant of mixed lymphocyte cultures by treatment with 15-deoxyspergualin. The mechanism of action of 15-deoxyspergualin on the immune system was discussed.
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AKIHITO YAMAGUCHI, MAYUMI NEMOTO, AKIKO ADACHI, TSUNEYOSHI INABA, TETS ...
1986 Volume 39 Issue 12 Pages
1744-1753
Published: 1986
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When
Citrobacter freundii cephalosporinase was incubated with 6β-[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin sulfone (cloxacillin sulfone) in phosphate buffer, the enzyme was suddenly inactivated just after the completion of enzymatic degradation of the cloxacillin sulfone. Such delayed inactivation was due to a secondary inhibitor formed from cloxacillin sulfone during the incubation period. The inactivation was delayed due to the protection of the enzyme by cloxacillin sulfone from the attack of the secondary inhibitor. Phosphate anions were essential for the formation of the secondary inhibitor. However, once the secondary inhibitor was formed, the inactivation occurred in the absence of phosphate anions although the degree of the inactivation depended on the length of the preincubation period with phosphate anions. The main species (more than 80%) of the inactivated enzyme was detected as a single protein band with a slightly lower pI value than that of the native enzyme on isoelectric focusing on a plate.
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JOSÉ M. LUENGO, JOSÉ L. IRISO, M. J. LÓPEZ-NIETO
1986 Volume 39 Issue 12 Pages
1754-1759
Published: 1986
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In vitro synthesis of different natural penicillins (hexanoyl, heptanoyl and octanoyl-penicillin) have been carried out by direct acylation of 6-aminopenicillanic acid (6-APA) with several fatty acid-CoA derivatives (hexanoyl-CoA, heptanoyl-CoA and octanoyl-CoA). The reactions were catalyzed by the enzyme Acyl-CoA: 6-aminopenicillanic acid acyltransferase from
Penicillium chrysogenum AS-P-78. This enzyme only accepts as substrate, aliphatic side chain precursors whose carbon length is between 6 and 8 atoms. Although the enzymatic synthesis of octanoylpenicillin has been previously reported the
in vitro synthesis of hexanoyl and heptanoyl penicillins is described here for the first time.
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URSULA FAUTH, HANS ZÄHNER, ANDREAS MÜHLENFELD, HANS ACHENBAC ...
1986 Volume 39 Issue 12 Pages
1760-1764
Published: 1986
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ROBIN D. CLARK, MICHAEL L. MADDOX, HOWARD R. SPIRES, PETER L. LONG
1986 Volume 39 Issue 12 Pages
1765-1768
Published: 1986
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HIROSHI YAMAKI, NOBUO TANAKA, HIROYOSHI ARIGA
1986 Volume 39 Issue 12 Pages
1769-1771
Published: 1986
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GERALD L. ROWIN, JACK E. MILLER, GEORG ALBERS-SCHÖNBERG, JANET C. ...
1986 Volume 39 Issue 12 Pages
1772-1775
Published: 1986
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SHIGEYUKI MIZOBUCHI, JUNICHIRO MOCHIZUKI, HIROSHI SOGA, HIROYUKI TANBA ...
1986 Volume 39 Issue 12 Pages
1776-1778
Published: 1986
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KAZUYUKI DOBASHI, KUNIO ISSHIKI, TSUTOMU SAWA, TAMAMI OBATA, MASA HAMA ...
1986 Volume 39 Issue 12 Pages
1779-1783
Published: 1986
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KAZUO TSUZUKI, HAJIME MATSUBARA, AKIRA NAKAGAWA, SATOSHI OMURA
1986 Volume 39 Issue 12 Pages
1784-1787
Published: 1986
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I. STRUCTURE-ACTIVITY RELATIONSHIPS IN SOME SEMI-SYNTHETIC 7α-FORMAMIDOCEPHALOSPORINS
MICHAEL J. BASKER, CLIVE L. BRANCH, STEPHEN C. FINCH, ANGELA W. GUEST, ...
1986 Volume 39 Issue 12 Pages
1788-1791
Published: 1986
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II. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF SOME 7α-FORMAMIDOCEPH-3-EM-1-OXIDE AND 7α-FORMAMIDO-1-OXADETHIACEPH-3-EM DERIVATIVES
CLIVE L. BRANCH, MICHAEL J. BASKER, MICHAEL J. PEARSON
1986 Volume 39 Issue 12 Pages
1792-1795
Published: 1986
Released on J-STAGE: April 19, 2006
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