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I. Taxonomy, Fermentation, Isolation and Characterization
MASATO NAKAMURA, YASUNOBU ITO, KIYOSHI OGAWA, YUJI MICHISUJI, SHIN-ICH ...
1995 Volume 48 Issue 12 Pages
1389-1395
Published: December 25, 1995
Released on J-STAGE: April 19, 2006
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Stachybocins A, B and C, novel endothelih (ET) receptor antagonists, were isolated from the culture filtrate of
Stachybotrys sp. M6222. They were extracted with ethyl acetate and then purified by alumina and silica gel column chromatographies. The molecular formulae of Stachybocins were determined to be C
52H
70N
2O
10 (stachybocin A) and C
52H
70N
2O
11 (stachybocins B and C). It was supposed that they consisted of spirobenzofuran and terpene units from NMR spectra. They showed the inhibitory activity of
125I-ET-1 binding to rat ET
A, human ET
A and human ET
B receptors.
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II. Structure Determination of Stachybocins A, B and C
KIYOSHI OGAWA, MASATO NAKAMURA, MITSUO HAYASHI, SATOSHI YAGINUMA, SYUJ ...
1995 Volume 48 Issue 12 Pages
1396-1400
Published: December 25, 1995
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The structures of Stachybocins A, B and C, new endothelin receptor antagonists, were determined by NMR spectral analysis using pulse-field-gradient techniques. Stachybocin A consists of two spirobenzofuran units each fused to a substituted decalin, which were connected by a lysine residue. Stachybocins B and C are derivatives of Stachybocin A with an additional hydroxy group at the same position in the different decalin unit.
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TATSUHIRO OGAWA, KATSUHIKO ANDO, YUMIKO AOTANI, KATSUMI SHINODA, TAKEO ...
1995 Volume 48 Issue 12 Pages
1401-1406
Published: December 25, 1995
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RES-1214-1 and -2, novel and non-peptidic endothelin antagonists, were isolated from the culture broth of a fungus,
Pestalotiopsis sp. RE-1214. RES-1214-1 and -2 selectively inhibited the ET-1 binding to endothelin type A receptor (ET
A receptor) with IC
50 values of 1.5μM and 20μM, respectively. RES-1214-1 and -2 inhibited the increase in intracellular Ca
2+ concentration elicited by 1 nM ET-1 in A10 cells. Taxonomy of producing strains, fermentation, isolation, structural determination, and biochemical properties of RES-1214-1 and -2 are described.
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TERUMI KAGAMIZONO, EMIKO NISHINO, KEITA MATSUMOTO, AKIRA KAWASHIMA, MA ...
1995 Volume 48 Issue 12 Pages
1407-1413
Published: December 25, 1995
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A new platelet aggregation inhibitor, bassiatin, was isolated from the cultured broth of
Beauveria bassiana which had been isolated from a soil sample collected in Yunnan province, China. The structure of bassiatin was determined to be (3
S, 6
R)-4-methyl-6-(1-methylethyl)-3-phenylmethyl-1, 4-perhydrooxazine-2, 5-dione by NMR analysis, X-ray crystallographic analysis and chemical synthesis. Bassiatin inhibited ADP-induced aggregation of rabbit platelets with the IC
50 being 1.9×10
-4M.
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KAZURO SHIOMI, HONG YANG, Qi Xu, NORIKO ARAI, MIKIE NAMIKI, MASAHIKO H ...
1995 Volume 48 Issue 12 Pages
1413-1418
Published: December 25, 1995
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A new radical scavenger, named phenopyrrozin, was isolated from the culture broth of
Penidllium sp. FO-2047. Phenopyrrozin was purified from whole broth by solvent extraction, silica gel chromatography, and HPLC. The structure of phenopyrrozin was elucidated as 5, 6, 7, 7a-tetrahydro2-hydroxy-l-phenyl-3
H-pyrrolizin-3-one. The IC
50 of phenopyrrozin against lipid peroxidation induced by Cr
2K
2O
7 was 73μg/ml. Phenopyrrozin also reduced chromosomal aberrations induced by paraquat.
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KEIJI HASUMI, KAZUYUKI TAKIZAWA, FUMIHITO TAKAHASHI, JONG Koo PARK, AK ...
1995 Volume 48 Issue 12 Pages
1419-1424
Published: December 25, 1995
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A complex of metabolites consisting of two isomeric cyclic acylpeptides was isolated from a culture of
Bacillus sp. A1238 by successive chromatographies on Amberlite XAD-7, silica gel and silica ODS columns. By a combination of spectroscopic and chemical analyses, the two subcomponents were identified as isomers of halobacillin, and the complex was designated isohalobacillin. Each molecule of isohalobacillin subcomponents contains either a 3-hydroxy-l-oxo-13-methyltetradecyl or a 3-hydroxy-1-oxo-12-methyltetradecyl moiety in place of a 3-hydroxy-loxopentadecyl moiety that is found in the halobacillin molecule. In a cell-free assay, isohalobacillin inhibited acyl-CoA: cholesterol acyltransferase by 50% at a concentration of 50μM. When added to a culture of macrophage J774, the agent inhibited oxidized low density lipoprotein-induced synthesis of cholesteryl ester from [
14C]oleate without affecting surface binding, internalization and degradation of the lipoprotein in the cells.
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I. Taxonomy, Fermentation, Isolation, Physico-chemical Properties and Biological Activities
KENICHI YASUMURO, YASUTO SUZUKI, MITSUYOSHI SHIBAZAKI, KYOKO TERAMURA, ...
1995 Volume 48 Issue 12 Pages
1425-1429
Published: December 25, 1995
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In the course of our screening for elastase inhibitors from microorganism, we have found two new cyclic-depsipeptides designated YM-47141 and 47142. In this paper, we describe the taxonomy of the producing organism and isolation, physico-chemical properties, and biological activities of YM-47141 and 47142.
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II. Structure Elucidation
MASAYA ORITA, KENICHI YASUMURO, KUNIHIKO KOKUBO, MINORU SHIMIZU, KENJI ...
1995 Volume 48 Issue 12 Pages
1430-1434
Published: December 25, 1995
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YM-47141 and YM-47142 are new elastase inhibitor produced by
Flexibacter sp. Q17897. These structures were elucidated by MS and NMR spectral analysis. YM-47141 and YM-47142 were the cyclic pep tides containing tricarbonyl moiety hydrated on the center carbonyl carbon in DMSO-
d6.
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I. Taxonomy, Fermentation, Isolation and Biological Activities
MASAHIKO HAYASHI, YONG-PIL KIM, HIDEMI HIRAOKA, MASAHIKO NATORI, SATOS ...
1995 Volume 48 Issue 12 Pages
1435-1439
Published: December 25, 1995
Released on J-STAGE: April 19, 2006
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Potent anti-adherent activity was detected in fermentation extracts of microbial strain FO-5050. Active compounds designated macrosphelide A and B were isolated and the structure was determined to be 16-membered macrolide antibiotics possessing three ester bonds in the ring structure. Macrosphelide A dose-dependently inhibited the adhesion of HL-60 cells to LPS-activated HUVEC monolayer (IC
50, 3.5μM); macrosphelide B also inhibited HL-60 adhesion but to a lesser extent (IC
50, 36μM). Macrosphelide A did not show any antimicrobial and cytocidal activities at the concentration of 1000μg/ml and 100μg/ml, respectively.
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MIN CHU, IMBI TRUUMEES, MARNIE L. ROTHOFSKY, MAHESH G. PATEL, FRANK GE ...
1995 Volume 48 Issue 12 Pages
1440-1445
Published: December 25, 1995
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Sch 52900 (
1) and Sch 52901 (
2), two new inhibitors of
c-fos proto-oncogene induction, have been isolated from the fermentation broth of the fungal culture (SCF-1168),
Gliocladium sp. Along with compounds
1 and
2, a known compound verticillin A (
3) was also obtained from the culture. Structure elucidation of
1 and
2, accomplished by analysis of spectral data in comparison with the data of
3, revealed both
1 and
2 were found to be closely related to the verticillin family of diketopiperazines. All three compounds prevented serum-stimulated transcription of the human
c-fos promoter, using a
fos/lac Z reporter gene assay, with IC
50 values of 1.5, 18 and 0.5μM for
1,
2 and
3, respectively. Northern analysis revealed that exposure of cells to compound
3 causes inhibition of both phorbol ester-induced
c-fos induction and serum-induced JE induction in the absence of inhibiting RNA synthesis, as measured by [
3H]uridine incorporation. These results suggest that this class of compounds exerts antitumor activity by blocking a signal transduction pathway that is common to and necessary for the induction of at least a subset of immediate early genes involved in cell proliferation.
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KIMBERLY D. MCBRIEN, RONALD L. BERRY, SUSAN E. LOWE, KIM M. NEDDERMANN ...
1995 Volume 48 Issue 12 Pages
1446-1452
Published: December 25, 1995
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The new cytotoxic agents rakicidins A and B were isolated from cultured broth of a
Micromonospora sp. Spectroscopic and amino acid analysis has shown that rakicidin A is a new cyclic lipopeptide, consisting of 4-amino-penta-2, 4-dienoic acid, 3-hydroxy-2, 4, 16-trimethylheptadecanoic acid, sarcosine, and 3-hydroxyasparagine. Rakicidin B differs by one methylene group in the lipid side chain. These compounds exhibited cytotoxicity against the Ml09 cell line.
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CHIEKO KUNUGITA, FUSAHIRO HIGASHITANI, AKIO HYODO, NORIO UNEMI, MATSUH ...
1995 Volume 48 Issue 12 Pages
1453-1459
Published: December 25, 1995
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A new extended spectrum β-lactamase was detected in
Serratia marcescens 42039 that was isolated from urine of patients with complicated urinary tract infection in Japan. This strain produced three different β-lactamase types (TEM-1, a cephalosporinase, and a new β-lactamase: CKH-1). The TEM-1 and CKH-1 encoding genes were conjugated from
S. marcescens 42039 to
Escherichia coli K-12 at frequencies of 10
-5 to 10
-6. The MICs of β-lactams against the transconjugant were: ampicillin >1600, piperacillin 800, cephalothin 1600, ceftazidime 6.25, cefotaxime 100, and ceftriaxone 200μg/ml. The CKH-1 enzyme was purified to more than 90% by ion-exchange chromatography. The molecular weight of purified CKH-1 was 30 K dalton and the isoelectric point was 8, 2, Relative Vmax/
Km values (cephaloridme=100) of penicillin G, cephalothin, and oxyiminocephalosporins such as cefuroxime, ceftriaxone, and cefotaxime, were 256, 226, 116, 87, and 49, respectively. The I
50 values of tazobactam, BRL-42715, and clavulanic acid against CKH-1 enzyme were 0.0011, 0.0002, and 0.097μM, respectively. The enzymatic activity of CKH-1 was not inhibited by EDTA and anti-TEM-1 serum. These findings indicate that CKH-1 is a member of the groups of class A β-lactamases. This is the first report of a plasmid-mediated oxyiminocephalosporin hydrolyzing broad-spectrum β-lactamase from clinical isolates of
S. marcescens.
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TAKUMI WATANABE, TOMIO TAKEUCHI, MASAMI OTSUKA, SHIN-ICHIRO TANAKA, KA ...
1995 Volume 48 Issue 12 Pages
1460-1466
Published: December 25, 1995
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We have synthesized derivatives of dephostatin, a protein tyrosine phosphatase (PTPase) inhibitor, to study the structure-activity relationships of this inhibitor. Inactive analogs revealed some insight into structural requirements for PTPase inhibitory activity of dephostatin. Both a nitroso group and phenolic hydroxyl groups were found to be essential for the inhibitory activity. Among the dephostatin derivatives synthesized, one of the regioisomers of dephostatin showed PTPase inhibitory activity equivalent to that of dephostatin, and also had increased stability.
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TERUYUKI SAKAI, HIROYUKI KAWAI, MASARU KAMISHOHARA, ATSUO ODAGAWA, AKA ...
1995 Volume 48 Issue 12 Pages
1467-1480
Published: December 25, 1995
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New derivatives of spicamycin modified at the fatty acid moieties of the molecule were synthesized and their structure-activity relationships were examined. The antitumor activity was greatly influenced by modification of the fatty acid moieties to tetradecadienoyl or dodecadienoyl analogues exhibiting better antitumor activity against COL-1 human colon cancer xenograft than SPM VIII.
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KOICHI NISHI, MITSURU IMUTA, YASUO KIMURA, HIDEAKI MIWA
1995 Volume 48 Issue 12 Pages
1481-1487
Published: December 25, 1995
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The synthesis and antibacterial activity of the title compounds having an isoxazolidine ring at the C-2 position are described. These derivatives were synthesized by the 1, 3-dipolar cycloaddition reaction of nitrone with 2-vinyl carbapenems. This 1, 3-dipolar cycloaddition reaction proceeded regioselectively to give diastereomeric isomers of 2-(isoxazolidin-5-yl)carbapenems. It was ascertained that the antibacterial activity of β-methylcarbapenem derivatives was superior to that of the corresponding 1H-carbapenem derivatives, and between the 2-(isoxazolidin-5-yl)-1β-methylcarbapenems the antibacterial activity of the 5'
R-isomer was slightly better than that of the 5'
S-isomer.
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ROBERTA FONTANA, MARIA ALTAMURA, FEDERICO ARCAMONED, GIUSEPPE CORNAGLI ...
1995 Volume 48 Issue 12 Pages
1488-1493
Published: December 25, 1995
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The antibacterial activities of three new penems with 4-hydroxyprolinamide, 1-prolinamide and
N-methyl-
N-2-propionamide substituents, respectively, in position 2 and of their stereoisomers were examined against
Staphylococcus aureus,
Enterococcus faecalis,
Enterococcus faecium,
Escherichia coli and
Pseudomonas aeruginosa. All substituents conferred a broad antibacterial spectrum on the penem moiety. Changes in stereoisomerism selectively improved the activity against
E. coli,
S. aureus or enterococci. The structure-activity relationships of each compound were discussed in relation to minimum inhibitory concentrations, penicillin-binding protein (PBP) affinity and outer membrane permeability coefficient in
E. coli. In this microorganism, PBP 2 was the target for all compounds. Changes in stereoisomerism influenced the affinity for PBPs 1A/B and 2. All antibiotics easily permeated the outer membrane of
E. coli and, within each group of compounds, the penetration rate correlated with the antibacterial activity.
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TAKASHI HIRAO, NOBUAKI TSUGE, SHINSUKE IMAI, KAZUO SHIN-YA, HARUO SETO
1995 Volume 48 Issue 12 Pages
1494-1496
Published: December 25, 1995
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KIN SING LAM, JUDITH A. VEITCH, JERZY GOLIK, WILLIAM C. ROSE, TERRENCE ...
1995 Volume 48 Issue 12 Pages
1497-1501
Published: December 25, 1995
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MASAYUKI IGARASHI, WEI CHEN, TOSHIO TSUCHIDA, MAYA UMEKITA, TSUTOMU SA ...
1995 Volume 48 Issue 12 Pages
1502-1505
Published: December 25, 1995
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KATSUHISA KOJIRI, SHIGERU NAKAJIMA, AISAKU FUSE, HAJIME SUZUKI, HIROYU ...
1995 Volume 48 Issue 12 Pages
1506-1508
Published: December 25, 1995
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TOMIO MORINO, MASAKAZU NISHIMOTO, AKIRA MASUDA, SHINJI FUJITA, TAKAAKI ...
1995 Volume 48 Issue 12 Pages
1509-1510
Published: December 25, 1995
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LUCIA CARRANO, AMBRA GUINDANI, MAURIZIO DENARO, KHALID ISLAM
1995 Volume 48 Issue 12 Pages
1511-1514
Published: December 25, 1995
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II. Sequence Analysis and Structure Determination of Siamycin I
D. J. DETLEFSEN, S. E. HILL, K. J. VOLK, S. E. KLOHR, M. TSUNAKAWA, T. ...
1995 Volume 48 Issue 12 Pages
1515-1517
Published: December 25, 1995
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TOMOYUKI SHIBATA, SHINWA KURIHARA, TETSUO OIKAWA, NOBUYUKI OHKAWA, NAO ...
1995 Volume 48 Issue 12 Pages
1518-1520
Published: December 25, 1995
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NAOTO KAWAMURA, RYUICHI SAWA, YOSHIKAZU TAKAHASHI, TSUTOMU SAWA, NAOKO ...
1995 Volume 48 Issue 12 Pages
1521-1524
Published: December 25, 1995
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YOSHITAKE TANAKA, MASAKO SUGOH, HIROSHI YOSHIDA, NORIKO ARAI, KAZURO S ...
1995 Volume 48 Issue 12 Pages
1525-1526
Published: December 25, 1995
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