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I. Taxonomy, Fermentation, Isolation and Biological Activity
KRISHNA KODUKULA, MAREDITH ARCURI, JINGFANG QIAN CUTRONE, ROBERT M. HU ...
1995 Volume 48 Issue 10 Pages
1055-1059
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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During the screening of microbial fermentation extracts for their ability to inhibit the binding of
125I-peptid YY (PYY) to the neuropeptide Y (NPY) receptor using the scintillation proximity assay (SPA), BMS-192548 was isolated from the extract of
Aspergillus niger WB2346 by bioassayguided fractionation. BMS-192548 showed the inhibitory activity against
125I-PYY binding to SK-N-MC and SMS-KAN cells, which express NPY
1 and NPY
2 receptors, respectively, with IC
50 values of 24μM in Y
1 and 27μM in Y
2 receptor binding. BMS-192548 demonstrated weak cytotoxicity against murine tumor cell line M-109 with an IC
50 value of 240 μM.
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II. Physico-chemical Properties and Structural Characterization
YUE-ZHONG SHU, JINGFANG QIAN CUTRONE, STEVEN E. KLOHR, STELLA HUANG
1995 Volume 48 Issue 10 Pages
1060-1065
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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The structure of BMS-192548, a tetracyclic binding inhibitor of neuropeptide Y receptors, was established by spectroscopic methods. The compound has an unusul B-C-D ring β-diketone moiety.
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I. Taxonomy, Fermentation, Isolation, Physico-chemical Properties and Biological Activities
YASUHISA TSURUMI, HIROTUGU UEDA, KENICHI HAYASHI, SHIGEHIRO TAKASE, MO ...
1995 Volume 48 Issue 10 Pages
1066-1072
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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Novel endothelin converting enzyme (ECE) inhibitors, WS75624 A and B, have been isolated from the fermentation broth of
Saccharothrix sp. No. 75624. These inhibitors were purified from an acetone extract of whole culture broth followed by HP-20 column chromatography, silica gel column chromatography and HPLC. WS75624 A and B showed highly potent ECE inhibitory activity, and both had IC
50 values of 0.03μg/ml. WS75624 A and B also showed other metalloprotease (collagenase and neutral endopeptidase) inhibitory activity with IC
50 values of 1 μg/ml.
Since large amount of WS75624 B was isolated, we tried
in vivo evaluation using WS75624 B. WS75624 B inhibited big endothelin-induced pressor effect when administered to SD rat intravenously with big ET-1.
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II. Structure Elucidation of WS75624 A and B
SEIJI YOSHIMURA, YASUHISA TSURUMI, SHIGEHIRO TAKASE, MASAKUNI OKUHARA
1995 Volume 48 Issue 10 Pages
1073-1075
Published: October 25, 1995
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The structures of WS75624 A and B, novel endothelin converting enzyme inhibitors, were determined to be
1 and
2A, respectively, by a combination of chemical evidence and a series of 2D NMR spectral analyses.
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TOSHIKI MACHIDA, KYOICHIRO HIGASHI, HIROSHI OGAWARA
1995 Volume 48 Issue 10 Pages
1076-1080
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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The effects of cochlioquinone A, isolated from
Drechslera sacchari, were studied
in vitro and
in vivo. This compound specifically inhibited diacylglycerol kinase activity with
Ki=3.lμM. The kinetics revealed that cochlioquinone A inhibited diacylglycerol kinase in competition with ATP, and non-competitively with diacylglycerol. The compound inhibited neither protein kinase C, epidermal growth factor receptor-associated protein tyrosine kinase, nor phospholipase C. Cochlioquinone A reduced the concentration of phosphatidic acid in T cell lymphoma with a half maximal concentration of 3μM, and simultaneously augmented the phosphorylation of SOkDa protein, a known substrate of protein kinase C. The degree of the phosphorylation of 80 kDa protein in the presence of cochlioquinone A was similar to that in the presence of phorbol myristate acetate (0.1μg/ml).
These results demonstrate that cochlioquinone A is a specific inhibitor of diacylglycerol kinase, which regulates the activity of protein kinase C.
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MARTIN L. GILPIN, MARK FULSTON, DAVID PAYNE, REBECCA CRAMP, IAN HOOD
1995 Volume 48 Issue 10 Pages
1081-1085
Published: October 25, 1995
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Two novel metabolites, SB 212021 and SB 212305, have been isolated from a
Streptomyces and shown to have molecular formulae of C
15H
10N
2O
5 and C
20H
17N
3O
8S, respectively. The structures were deduced by a combination of NMR techniques and mass spectral fragmentation patterns and shown to be novel members of the phenazine group of antibiotics. In the absence of added zinc, both compounds had IC
50's of 1-75μM for the
Bacteroides fragilis 262 CfiA and
Xanthomonas maltophilia L-1 metallo-β-lactamases. The compounds also inhibited ACE with IC
50's of 55 and 68μM, respectively. Mode of action studies illustrate that the compounds inihibit some metalloenzymes by chelation of the active site metal ion. They exhibit poor antibacterial activity.
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I. Taxonomy, Fermentation, Isolation and Biological Characteristics
KANKI KOMIYAMA, SATOSHI TAKAMATSU, YONG-PIL KIM, ATSUKO MATSUMOTO, YOK ...
1995 Volume 48 Issue 10 Pages
1086-1089
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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In the course of screening for non-steroidal growth inhibitors of testosterone-responsive Shionogi carcinoma 115 cells, louisianins A, B, C and D, were isolated from fermentation broth of
Streptomyces sp. WK-4028. Louisianin A remarkably inhibited the growth of SC 115 cells in the presence of 10
-7M testosterone at an IC
50 value of 0.6μg/ml, whereas, no inhibition was observed on the other cell lines. Furthermore, inhibitory activity of testosterone 5α-reductase and antimicrobial activity have not been observed at a concentration of 50μg/ml and 1, 000μg/ml, respectively.
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II. Physico-chemical Properties and Structural Elucidation
SATOSHI TAKAMATSU, YONG-PIL KIM, MASAHIKO HAYASHI, KIMIO FURUHATA, HIR ...
1995 Volume 48 Issue 10 Pages
1090-1094
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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New non-steroidal growth inhibitors of testosterone-responsive SC 1 15 cells, louisianins A (MW: 189; C
11H
11NO
2), B (MW: 191; C
11H
13NO
2), C (MW: 173; C
11H
11NO) and D (MW: 173; C
11H
11NO) were isolated from the cultured broth of
Streptomyces sp. WK-4028. Their structures were determined on the basis of spectroscopic data. The structure of louisianin A in particular was confirmed by X-ray crystallographic analysis. The four compounds commonly possess a unique pyrindine skeleton in the molecule.
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YOSHIO KAJIMURA, MASANORI SUGIYAMA, MIYUKI KANEDA
1995 Volume 48 Issue 10 Pages
1095-1103
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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Bacillopeptins, new iturin-group antifungal antibiotics, were isolated from the culture broth of
Bacillus subtilis FR-2 obtained from the rhizosphere of garlic suffering from the basal rot caused by
Fusarium oxysporum. Their structures were elucidated to be cyclic lipopeptides similar to bacillomycin L by NMR and mass spectral studies coupled with amino acid analysis. The absolute configuration of each amino acid residue was determined by chiral HPLC.
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I. Taxonomy, Fermentation, Isolation, Characterization and Biological Activities
TOSHIO TSUCHIDA, HIRONOBU IINUMA, CHIGUSA NISHIDA, NAOKO KINOSHITA, TS ...
1995 Volume 48 Issue 10 Pages
1104-1109
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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The novel antimicrobial antibiotic against
Pasteurella piscicida, tetrodecamycin (
1) and weakly active dihydrotetrodecamycin (
2) were isolated from the fermentation broth of
Streptomyces nashvillensis MJ885-mF8. They were purified by adsorption on Diaion HP-20, silica gel column chromatography and crystallization. The MICs of
1 were 6.25-12.5μg/liter and 1.56-6.25μg/ml against Gram-positive bacteria including methicillin-resistant
Staphylococcus aureus (MRSA) and 12 strains of
P. piscicida, respectively.
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II. Structure Determination
TOSHIO TSUCHIDA, HIRONOBU IINUMA, RYUICHI SAWA, YOSHIKAZU TAKAHASHI, H ...
1995 Volume 48 Issue 10 Pages
1110-1114
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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Novel antimicrobial antibiotics against
Pasteurella piscidda, tetrodecamycin (
1) and weakly active dihydrotetrodecamycin (
2) were isolated from a culture broth of
Streptomyces nashvillensis MJ885-mF8. The planar structure of
1 was determined to be 2-acyl-4-ylidene tetronic acid alkyl ether containing decaline ring by various NMR spectral data of
1 and its acetyl derivative (
3). The structure of
2 was elucidated by comparison with the spectral data of
1 and confirmed by catalytic reduction of
1 into
2. The X-ray crystallography of
2 showed the relative stereochemistry. Their absolute configurations were determined by using modified Mosher's method.
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TOSHIO FUKAI, JUN KURODA, MASATAKA KONISHI, TARO NOMURA, NOBUAKI NARUS ...
1995 Volume 48 Issue 10 Pages
1115-1122
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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The structures of new antibiotics, Bu-2841-08 and -10, have been determined. They are cyclic depsipeptides and the sequence of amino acid residues was established by mass spectral analysis of the hydrolyzed linear peptide and NMR spectral analysis of the parent cyclic peptides.
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I. Taxonomy, Fermentation, Isolation and Biological Properties
EISAKU TAKAHASHI, TAKASHI KIMURA, KAZUHIKO NAKAMURA, MASATO ARAHIRA, M ...
1995 Volume 48 Issue 10 Pages
1124-1129
Published: October 25, 1995
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A novel herbicidal compound, phosphonothrixin, was found in the fermentation broth of
Saccharothrix sp. ST-888 cultured on a vegetable juice medium. The compound exhibiting acidic and hydrophilic properties was obtained when the fermentation broth of ST-888 was subjected to ion exchange chromatography, gel filtration chromatography and ion-pair chromatography. Phosphonothrixin significantly inhibited germination of gramineous and broadleaf weeds. Foliar application of this antibiotic gave rise to chlorosis in all of the plants tested.
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II. Structure Determination
TAKASHI KIMURA, KAZUHIKO NAKAMURA, EISAKU TAKAHASHI
1995 Volume 48 Issue 10 Pages
1130-1133
Published: October 25, 1995
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Phosphonothrixin (
1) is a novel herbicidal agent produced by
Saccharothrix sp. ST-888. This unique compound possessing a C-P bond and an isoprene unit was determined to be 2-hydroxy-2-hydroxymethyl-3-oxobutyl-phosphonic acid. Unusually rapid proton-deuterium (H-D) exchange of the methyl ketone unit of this antibiotic in D
2O solution was observed. Phosphonothrixin can be classified as a new type of natural product herbicide having a C-P bond in the molecule.
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KAZUHIKO NAKAMURA, TAKASHI KIMURA, HISASHI KANNO, EISAKU TAKAHASHI
1995 Volume 48 Issue 10 Pages
1134-1137
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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Phosphonothrixin (
1) is a novel herbicidal agent produced by
Saccharothrix sp. ST-888, with a unique structure possessing a C-P bond and an isoprene unit. The total synthesis of this antibiotic was accomplished from methyl (bromomethyl)acrylate in six steps.
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KATSUHISA YAMAZAKI, MASAHIDE AMEMIYA, MASAAKI ISHIZUKA, TOMIO TAKEUCHI
1995 Volume 48 Issue 10 Pages
1138-1140
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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We have employed the DNA-methylgreen binding assay as a primary screening method for identifying apoptosis inducers in microbial products. Capsimycin, toyocamycin and cytostatin affect the binding of methylgreen to DNA of FS3 cells in this test system. The effect of cytostatin on apoptosis induction was confirmed by means of the ELISA system.
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CHARLES J. GILL, GEORGE K. ABRUZZO, AMY M. FLATTERY, JEFFREY G. SMITH, ...
1995 Volume 48 Issue 10 Pages
1141-1147
Published: October 25, 1995
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L-701, 677, L-708, 299 and L-708, 365 are novel azalide derivatives of erythromycin that exhibit improved acid stability over erythromycin, azithromycin and clarithromycin. The half-life in aqueous solution at pH = 2.1 of these compounds ranged from 0.3 hour for erythromycin to 16.2 hours for L-708, 299. The rank order of half-life in acid solution from most to least stable was L-708, 299>L-701, 677>L-708, 365 > azithromycin = clarithromycin>erythromycin. In a disseminated
Streptococcus pyogenes mouse infection model, azithromycin and L-708, 365 were slightly more efficacious than clarithromycin, L-701, 677 and L-708, 299; all 5 compounds being more active than erythromycin. In a
Klebsiella pneumoniae pulmonary challenge mouse model, azithromycin, L-701, 677, L-708, 299 and L-708, 365 were all equal in efficacy and at least four-fold more active than clarithromycin and erythromycin. Clarithromycin, L-708, 365 and interestingly erythromycin, showed greater bacterial clearance than azitnromycin, L-701, 677 and L-708, 299 in a localized infection model that measured clearance of
Staphylococcus aureus from mouse thigh tissues. Our results indicate that L-701, 677, L-708, 299 and L-708, 365 exhibit improved acid stability and were at least equally efficacious as presently marketed macrolide/azalide antibiotics.
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II. Structure Determination
TOSHIO TSUCHIDA, RYUICHI SAWA, YOSHIKAZU TAKAHASHI, HIRONOBU IINUMA, T ...
1995 Volume 48 Issue 10 Pages
1148-1152
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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A new structural class of antibiotics, azicemicins A (
1) and B (
2) were isolated from the culture broth of
Amycolatopsis sp. MJ126-NF4. Their structures were elucidated from their physico-chemical properties, various NMR experiments and chemical transformations and were shown to be 3-(lmethyl-2-aziridinyl)-and 3-(2-aziridinyl)-3, 4-dihydro-3, 7, 8, 10, 12b-pentahydroxy-9, 12-dimethoxybenz[a]anthracene-1, 6(2H, 5H)-dione, respectively.
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OSAMU JOHDO, H. NISHIDA, R. OKAMOTO, AKIHIRO YOSHIMOTO, TOMIO TAKEUCHI
1995 Volume 48 Issue 10 Pages
1153-1158
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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Two new anthracycline antibiotics, 10-
epi-oxaunomycin and 10-
epi-11-deoxyoxaunomycin, were photochemically obtained from anthracycline metabolites D788-1 (10-carboxy-13-deoxocarminomycin) and D788-3 (10-carboxy-ll-deoxy-13-deoxocarminomycin) and were examined for their growth inhibitory activities on cultured LI210 leukemic cells. Effects of the S configuration of C-10 and a hydroxyl group at C-11 on the bioactivity are discussed in comparison with oxaunomycin and 11-deoxyoxaunomycin.
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MASAHIRO NATSUME, JUNKO TAZAWA, KAORI YAGI, HIROSHI ABE, SATORU KONDO, ...
1995 Volume 48 Issue 10 Pages
1159-1164
Published: October 25, 1995
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Nine new pamamycin homologues were isolated from the culture broth of
Streptomyces alboniger IFO 12738 using a combination of ODS and NH
2 HPLCs, and their structures determined by GC-MS. The structural differences in these homologues are in the numbers and positions of methyl and ethyl groups. The aerial mycelium-inducing and growth-inhibitory activities in
S. alboniger of these homologues and their antibiotic activity against
Bacillus subtilis were examined. The effects of the alkyl substituents on these activities are discussed.
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M. ESTELA ALVAREZ, CAROLE B. WHITE, JILL GREGORY, GWENDOLYN C. KYDD, A ...
1995 Volume 48 Issue 10 Pages
1165-1167
Published: October 25, 1995
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CHOONG HWAN LEE, HIROYUKI KOSHINO, MYUNG CHUL CHUNG, HO JAE LEE, YUNG ...
1995 Volume 48 Issue 10 Pages
1168-1170
Published: October 25, 1995
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STEPHEN J. COVAL, MOHINDAR S. PUAR, DAVID W. PHIFE, JOSEPH S. TERRACCI ...
1995 Volume 48 Issue 10 Pages
1171-1172
Published: October 25, 1995
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JUN KOHNO, MAKI NISHIO, KIMIO KAWANO, SHIN-ICHI SUZUKI, SABURO KOMATSU ...
1995 Volume 48 Issue 10 Pages
1173-1175
Published: October 25, 1995
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MAKOTO UBUKATA, B. RADHA RANI, CHENG-BINI CUI, HIROYUKI OSADA
1995 Volume 48 Issue 10 Pages
1176-1178
Published: October 25, 1995
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B. RADHA RANI, CHENG-BINI CUI, MAKOTO UBUKATA, HIROYUKI OSADA
1995 Volume 48 Issue 10 Pages
1179-1181
Published: October 25, 1995
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YOICHI HAYAKAWA, KIN-YA SOHDA, HARUO SETO
1995 Volume 48 Issue 10 Pages
1182-1184
Published: October 25, 1995
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J. NAFZIGER, G. AVERLAND, E. BERTOUNESQUE, G. GAUDEL, C. MONNERET
1995 Volume 48 Issue 10 Pages
1185-1187
Published: October 25, 1995
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MICHIHIRO SUGANO, AIYA SATO, YASUTERU IIJIMA, KOUHEI FURUYA, HARUMITSU ...
1995 Volume 48 Issue 10 Pages
1188-1190
Published: October 25, 1995
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TOMOHISA KUZUYAMA, TAKAYUKI SEKI, TOHRU DAIRI, TOMOMI HIDAKA, HARUO SE ...
1995 Volume 48 Issue 10 Pages
1191-1193
Published: October 25, 1995
Released on J-STAGE: April 19, 2006
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