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I. ISOLATION AND CHARACTERIZATION
E. SELVA, G. BERETTA, N. MONTANINI, G. S. SADDLER, L. GASTALDO, P. FER ...
1991 Volume 44 Issue 7 Pages
693-701
Published: July 25, 1991
Released on J-STAGE: April 19, 2006
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A novel antibiotic, GE2270 A, was isolated from the fermentation broth of a strain of
Planobispora rosea. The product was found to inhibit bacterial protein synthesis. Structural characteristics showed similarities between GE2270 A and thiazolyl peptides such as micrococcin which is known to inhibit protein synthesis by acting directly on the ribosome. Despite this similarity GE2270 A showed functional analogy to kirromycin-like antibiotics and pulvomycin, as its molecular target was found to be elongation factor Tu (EF-Tu).
GE2270 A is active against Gram-positive microorganism and anaerobes and differs from the other EF-Tu inhibitors in its spectrum of antimicrobial activity.
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II. STRUCTURE ELUCIDATION
JÜRGEN KETTENRING, LUIGI COLOMBO, PIETRO FERRARI, PAOLO TAVECCHIA ...
1991 Volume 44 Issue 7 Pages
702-715
Published: July 25, 1991
Released on J-STAGE: April 19, 2006
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GE2270 A, produced by
Planobispora rosea ATCC 53773, inhibits Gram-positive bacteria and anaerobes by acting on the bacterial protein synthesis. The structure has been determined by physico-chemical methods applied to the intact molecule and to the main hydrolysis products.
Characterization by UV, IR, NMR (double quantum filter COSY), acid-base ionization, elemental analysis and FAB-MS indicated that GE2270 A is a highly modified peptide having MW 1, 289 and formula C
56H
55N
15O
10S
6, and a weak basic function, and that it belongs to the thiazolyl peptide group of antibiotics. Acid hydrolysis yielded a main product (MW 634), responsible for the chromophoric absorption, and a number of hydrolyzed products of lower MW.
13C NMR inverse techniques and MS studies (El, positive ion chemical ionization, and collision induced dissociation FAB-MS-MS experiments) on GE2270 A, the chromophoric compound, and the other hydrolysis products led to the complete identification of the various amino acid residues and their sequence. Two out of the six chiral centers have been determined.
The structure is thought to originate from modification of a chain of 14 amino acids in a process which creates 6 thiazole rings and one pyridine. The modification process also closes the linear polypeptide to form a cyclic part with an attached side-chain. GE2270 A plausibly has a similar biosynthetic origin to that of other thiazolyl peptide antibiotics such as nosiheptide and micrococcin.
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YOSHIHIRO NISHIMOTO, SHOHEI SAKUDA, SEIJI TAKAYAMA, YASUHIRO YAMADA
1991 Volume 44 Issue 7 Pages
716-722
Published: July 25, 1991
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Three of new allosamidins, termed glucoallosamidins A (
5), B (
6) and methyl-
N-demethylallosamidin (
4), were isolated as yeast chitinase inhibitors from the mycelium of
Streptomyces sp. SA-684.
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TAXONOMY, FERMENTATION, ISOLATION, STRUCTURE DETERMINATION AND BIOLOGICAL ACTIVITY
KATSUHISA KOJIRI, HISAO KONDO, TOMOKO YOSHINARI, HIROHARU ARAKAWA, SHI ...
1991 Volume 44 Issue 7 Pages
723-728
Published: July 25, 1991
Released on J-STAGE: April 19, 2006
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A new antitumor substance, BE-13793C, which has topoisomerase inhibitory activity was isolated from the culture broth of a strain of actinomycetes. The producing strain, BA13793, isolated from a soil sample collected in Seto, Aichi Prefecture, Japan, had a resemblance to
Streptoverticillium mobaraense. The active principle was extracted from the mycelium of strain BA 13793 with methanol and purified by Sephadex LH-20 column chromatography. BE-13793C showed strong inhibitory activity against topoisomerases I and II and inhibited the growth of doxorubicin-resistant or vincristine-resistant P388 murine leukemia cell lines, as well as their parent P388 cell line.
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BARBARA G. ISAAC, STEPHEN W. AYER, LEO J. LETENDRE, RICHARD J. STONARD
1991 Volume 44 Issue 7 Pages
729-732
Published: July 25, 1991
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The structures of five naturally-occurring herbicidal nucleosides have been determined by spectral analysis. Three (5'-deoxyguanosine, coaristeromycin and S'-deoxytoyocamycin) are novel natural products while the remaining two (coformycin and adenine 9-β-D-arabinofuranoside) are known natural products which have not previously been reported to be herbicidal.
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I. PRODUCTION, ISOLATION, CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
NOBUAKI NARUSE, OSAMU TENMYO, KIMIO KAWANO, KOJI TOMITA, NORIYUKI OHGU ...
1991 Volume 44 Issue 7 Pages
733-740
Published: July 25, 1991
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Five unidentified actinomycete strains produced a series of novel antiviral antibiotics which have a unique 2, 6-dialkyl-10-ethyl-3(or 9)-hydroxy-13-tridecanelactam nucleus substituted with 3-amino-3, 6-dideoxy-L-talose or 3-amino-3, 6-dideoxy-L-mannose(L-mycosamine). The antibiotic components exhibited potent inhibitory activity against influenza virus type A Victoria strain infection in Madin Darby canine kidney cells by the cytopathic effect reduction assay.
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II. STRUCTURE DETERMINATION
NOBUAKI NARUSE, TAKASHI TSUNO, YOSUKE SAWADA, MASATAKA KONISHI, TOSHIK ...
1991 Volume 44 Issue 7 Pages
741-755
Published: July 25, 1991
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A series of structurally related antiviral antibiotics, fluvirucins A
1, A
2, B
1, B
2, B
3, B
4 and B
5 have been isolated from the fermentation broths of five unidentified actinomycete isolates. Based on spectroscopic analysis, partial degradation experiments and
13C-enriched acetic acid-fed biosynthetic studies, their structures were elucidated to be 2, 6, 10-trialkyl-3(or 9)-aminoglycosyl-13-tridecanelactams.
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III. THE STEREOCHEMISTRY AND ABSOLUTE CONFIGURATION OF FLUVIRUCIN A1
NOBUAKI NARUSE, MASATAKA KONISHI, TOSHIKAZU OKI, YOSHINOBU INOUYE, HIR ...
1991 Volume 44 Issue 7 Pages
756-761
Published: July 25, 1991
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Fluvirucin A
1 was established as (2
R, 3
S, 6
R, 10
S)-3-[(3-amino-3, 6-dideoxy-α-L-talopyranosyl)-oxy]-2, 6-dimethyl-10-ethyl-13-tridecanelactam by chemical, spectroscopic, and X-ray crystallographic analyses.
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HARUO OGAWA, KEIJI HASUMI, KAORU SAKAI, SHIGEO MURAKAWA, AKIRA ENDO
1991 Volume 44 Issue 7 Pages
762-767
Published: July 25, 1991
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Pannorin, a naphthopyrone that inhibits 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase, the rate-limiting enzyme in cholesterol synthesis, was isolated from a culture broth of
Chrysosporium pannorum Ml0539 by solvent extraction, Bio-Gel P-6 column chromatography and reverse phase HPLC (Silica ODS). Spectroscopic analyses of the compound yielded 4, 8, 10-trihydroxy-5-methyl-2
H-naphtho[1, 2-
b]pyran-2-one as the proposed structure. Pannorin inhibited HMG-CoA reductase and
in vitro sterol synthesis 50% at a concentration of 160μM.
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1. FERMENTATION, ISOLATION AND CHARACTERIZATION
TERUAKI OZASA, TAKASHI YONEDA, MARI HIRASAWA, KENICHI SUZUKI, KOICHI T ...
1991 Volume 44 Issue 7 Pages
768-773
Published: July 25, 1991
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New antibiotics designated as thiazocins A and B were isolated from the culture broth of
Actinosynnema sp. C-304. Thiazocins A and B exhibited inhibitory activities against an aldose reductase from human placenta.
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KAZUO TSUZUKI, FU-SHAN YAN, KAZUHIKO OTOGURO, SATOSHI OMURA
1991 Volume 44 Issue 7 Pages
774-784
Published: July 25, 1991
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Simple, efficient syntheses of jietacin A, a nematocidal antibiotic, and its analogs have been developed in order to study structure-activity relationships. A series of α, β-unsaturated azoxy compounds was prepared from phenylselenomethyl azoxy compounds as key intermediates and its nematocidal activity was determined.
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BEATE VON DER HAAR, DOUWE ROSENBERG, WERNER DITTRICH, HILDGUND SCHREMP ...
1991 Volume 44 Issue 7 Pages
785-792
Published: July 25, 1991
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Streptomyces lividans and several other
Streptomyces species are resistant to the steroid-like antibiotic fusidic acid. This resistance is mediated by structural modification of the antibiotic. Using TLC, CD, UV, IR, NMR and mass spectroscopy the structure of one of the resulting inactive compounds was determined. It is derived from fusidic acid by the loss of an acetyl group and the formation of a lactone ring between C-21 and C-16. In addition, helvolic acid, a compound closely related to fusidic acid, has been shown to be modified.
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BARBARA G. ISAAC, STEPHEN W. AYER, RICHARD J. STONARD
1991 Volume 44 Issue 7 Pages
793-794
Published: July 25, 1991
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BARBARA G. ISAAC, STEPHEN W. AYER, RICHARD J. STONARD
1991 Volume 44 Issue 7 Pages
795-796
Published: July 25, 1991
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DETECTION, ISOLATION AND BIOLOGICAL ACTIVITIES OF CHIRAL SYNTHONS FROM Streptomyces
SUSANNE GRABLEY, PETER HAMMANN, HEINZ KLUGE, JOACHIM WINK, PETRA KRICK ...
1991 Volume 44 Issue 7 Pages
797-800
Published: July 25, 1991
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NOBUYOSHI YASUDA, KAZUO SAKANE
1991 Volume 44 Issue 7 Pages
801-802
Published: July 25, 1991
Released on J-STAGE: April 19, 2006
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KEIKO NAKAGAWA, KAZUO SATO, TAKAO OKAZAKI, AKIO TORIKATA
1991 Volume 44 Issue 7 Pages
803-805
Published: July 25, 1991
Released on J-STAGE: April 19, 2006
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