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L. PAIRET, S. K. WRIGLEY, I. CHETLAND, E. E. REYNOLDS, M. A. HAYES, J. ...
1995 Volume 48 Issue 9 Pages
913-923
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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A series of azaphilones produced by
Penicillium sclerotiorum (Xenova culture collection number XI1853) active in assays for the detection of antagonists of the endothelin-A (ET
A) and endothelin-B (ET
B) receptors has been identified. The series includes two novel sclerotiorin analogues, (8
S, 8
a-
R)-7-deacetyl-1,
O8, 8, 8a-tetrahydro-7-
epi-sclerotiorin,
1, and its 5-dechloro analogue,
2. It also includes 5-chloroisorotiorin,
6, previously unreported as a natural product, in addition to the major product of these fermentations, (+)-sclerotiorin,
5. Data for the inhibition of endothelin-1 (ET-1) and endothelin-3 (ET-3) binding in the ET
A and ET
B receptor assays respectively are reported for this series. Compounds
1 and
2 were more selective for the rabbit ET
A receptor than for the rat ET
B receptor. The IC
50 values for
1 and
2 were 9 and 28 μM respectively in an assay based on binding of ET-1 to rabbit ET
A receptors. In an assay based on the binding of ET-3 to the rat ET
B receptor compounds
1 and
2 exhibited IC
50's of 77 and 172 μM. Members of this series of compounds demonstrated antagonist behavior in a secondary assay based on blockade of ET-1 stimulated arachidonic acid release from rabbit renal artery smooth muscle cells, when present at concentrations of ≥30μM.
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I. Production, Isolation, Characterization and Biological Activities
TSUTOMU KAMIYAMA, TAKAYUKI UMINO, TOMOKO SATOH, SAYOKO SAWAIRI, MICHIK ...
1995 Volume 48 Issue 9 Pages
924-928
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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Sulfobacins A and B, novel von Willebrand factor (vWF) receptor antagonists, have been isolated from the culture broth of
Chryseobacterium sp. (
Flavobacterium sp.) NR 2993 by ethyl acetate extraction, and by Sephadex LH-20 and silica gel column chromatographies. The physico-chemical properties of the Sulfobacins indicate that their structures are completely different from that of aurintricarboxylic acid, the one known vWF receptor antagonist. Sulfobacins A and B inhibit the binding of vWF.to its receptor with IC
50s of 0.47 and 2.2/IM, respectively. Sulfobacin A also inhibits ristocetin-induced agglutination in human platelets fixed with paraformaldehyde with an IC
50 of 0.58 μM.
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II. Structural Elucidation
TSUTOMU KAMIYAMA, TAKAYUKI UMINO, YOSHIKO ITEZONO, YUMIKO NAKAMURA, TO ...
1995 Volume 48 Issue 9 Pages
929-936
Published: September 25, 1995
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Sulfobacins A and B are novel von Willebrand factor (vWF) receptor antagonists produced by
Chryseobacterium sp. NR 2993. The structures of sulfobacins A and B have been determined to be (2
R, 3
R)-3-hydroxy-2[(
R)-3-hydroxy-15-methylhexadecanamido]-15-methylhexadecanesulfonic acid and (2
R, 3
R)-3-hydroxy-15-methyl-2-[13-methyltetradecanamido]-hexadecanesulfonic acid, respectively, by various 2D NMR experiments and by methanolysis. The absolute configurations of the sulfobacins were determined by a modified MOSHER'S method. The structures are related to sulfonolipids, major components of the cell envelope of gliding bacteria of the genus
Cytophaga.
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I. Production, Isolation and Biological Properties
HIROSHI TOMODA, MINAKO ITO, NORIKO TABATA, ROKURO MASUMA, YUICHI YAMAG ...
1995 Volume 48 Issue 9 Pages
937-941
Published: September 25, 1995
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Humicola sp. FO-2942, a soil isolate, was found to produce a series of new inhibitors of diacylglycerol acyltransferase (DGAT). Three active compounds, designated amidepsines A, B and C, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography, ODS column chromatography and HPLC. Amidepsines inhibit DGAT activity with IC
50 values of 10.2-51.6μM in an enzyme assay system using rat liver microsomes. Amidepsines also showed specific inhibition of triacylglycerol formation in intact Raji cells, indicating that they inhibit DGAT activity in living cells.
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II. Structure Elucidation of Amidepsines A, B and C
HIROSHI TOMODA, NORIKO TABATA, MINAKO ITO, SATOSHI OMURA
1995 Volume 48 Issue 9 Pages
942-947
Published: May 25, 1995
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Structures of amidepsines A, B, C and D, diacylglycerol acyltransferase (DGAT) inhibitors, were determined by spectroscopic studies including various NMR measurements. They were elucidated as 2-hydroxy-4-[[2-hydroxy-4-[(2, 4-dimethoxy-6-methylbenzoyl)oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid
N-alanine amide for amidepsine A, 2-hydroxy-4-[[2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid
N-alanine amide for amidepsine B and 2-hydroxy-4-[[2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid
N-valine amide for amidepsine C. Amidepsine D was identified with 2, 4-di-
O-methylgryphoric acid.
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SATOSHI NAKANISHI, SHIGERU CHIBA, HIROSHI YANO, ISAO KAWAMOTO, YUZURU ...
1995 Volume 48 Issue 9 Pages
948-951
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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A novel compound MS-444 was isolated from the culture broth of a bacterial strain KY7123. The strain was identified as
Micromonospora sp. from its morphological and cultural characteristics. The compound inhibited the activity of purified smooth muscle myosin light chain kinase with an IC
50 value of 10μM. The production, isolation, physico-chemical properties and biological activities of MS-444 were described in this paper.
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YUMIKO AOTANI, YUTAKA SAITOH
1995 Volume 48 Issue 9 Pages
952-953
Published: September 25, 1995
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MS-444 is a novel myosin light chain kinase inhibitor, isolated from the culture broth of
Micromonospora sp. KY7123. The structure of MS-444 was determined to be 5, 8-dihydroxy-3-methyl-(9
H)-naphtho[2, 3-c]furan-4-one by means of spectral analysis.
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YOICHI HAYAKAWA, KIN-YA SOHDA, KAZUO SHIN-YA, TOMOMI HIDAKA, HARUO SET ...
1995 Volume 48 Issue 9 Pages
954-961
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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The retinoblastoma protein (pRB) is inactivated during the development of a wide variety of human cancers. In the course of our screening for antitumor antibiotics by using pRB-inactivated cells, an actinomycete strain was found to produce two active substances, which were elucidated to be new members of the leptomycin-anguinomycin family by NMR spectral analysis and were designated anguinomycins C and D. The anguinomycins induced growth arrest against normal cells and induced cell death against transformed cells, in which pRB was inactivated by viral oncoproteins such as human papilloma virus E7, adeno virus El A and simian virus 40 large T antigen.
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HERBERT IRSCHIK, ROLF JANSEN, KLAUS GERTH, GERHARD HÖFLE, HANS RE ...
1995 Volume 48 Issue 9 Pages
962-966
Published: September 25, 1995
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A new antibiotic, chivosazol, was isolated from the culture broth of the myxobacterium
Sorangium cellulosum strain So eel2. It is a macrocyclic ring with one oxazol ring and a glycosidically bound 6-deoxyglucose (quinovose) at C-11. The antibiotic shows antimicrobial activity against yeasts and filamentous fungi, and is especially potent against mammalian cells. It was not active against bacteria.
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GIORGIO LAMPIS, DELIA DEIDDA, CARLO MAULLU, MARIA A. MADEDDU, RAFFAELL ...
1995 Volume 48 Issue 9 Pages
967-972
Published: September 25, 1995
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A series of new compounds with antiviral properties were isolated from a
Bacillus sp. strain B-60. They were named sattabacin (
1), hydroxysattabacin (
2), sattazolin (
3) and methylsattazolin (
4). The biologically active compounds were recovered from fermentation broth by ethyl acetate extraction and silica-gel column fractionation. Their antiviral activity was mainly expressed against the Herpes simplex viruses type 1 and 2. The compound
3 showed a selective inhibition of protein synthesis in Herpesvirus-infected cells.
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Production, Physico-chemical and Biological Properties
KLAUS GERTH, DIETMAR SCHUMMER, GERHARD HÖFLE, HERBERT IRSCHIK, HA ...
1995 Volume 48 Issue 9 Pages
973-976
Published: September 25, 1995
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An antifungal activity, ratjadon, was detected in the culture broth of
Sorangium cellulosum (Myxococcales) strain So ce360. The metabolite was quantitatively bound to the adsorber resin XAD-16, which was added to the medium at the beginning of the fermentation. The antibiotic spectrum was narrow, but some important phytopathogenic fungi, especially species of Oomycetes, were inhibited at very low concentrations.
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KLAUSJÜRGEN DORNBERGER, WOLFGANG IHN, MICHAEL RITZAU, UDO GRÄ ...
1995 Volume 48 Issue 9 Pages
977-989
Published: September 25, 1995
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Four new members of peptaibol antibiotics, designated as chrysospermins A, B, C, and D, were isolated from the mycelium of
Apiocrea chrysosperma AplOl by solvent extraction, silica gel chromatography and preparative recycling HPLC. Their structures as new nonadecapeptides were settled by detailed spectroscopic analysis and chemical degradation experiments. The chrysospermins display antibacterial and antifungal activity, and induce pigment formation by the fungus
Phoma destructiva.
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HERBERT A. KIRST, STEPHEN H. LARSEN, JONATHAN W. PASCHAL, JOHN L. OCCO ...
1995 Volume 48 Issue 9 Pages
990-996
Published: September 25, 1995
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A new member of the spiroketal-containing macrolide class of fermentation-derived natural products was isolated from mycelial extracts of
Streptomyces diastatochromogenes. The principal component, A82548A, was shown to possess a 22-membered macrolide ring system onto which was incorporated both a spiroketal and a hemiketal moiety. Relative stereochemistry was established by single crystal X-ray diffraction studies. Absolute stereochemistry was determined
via hydrolysis of the amino sugar glycosidically linked to the aglycone, which was identified as L-kedarosamine. The overall three-dimensional structure is closely related to that of the macrolides cytovaricin, rutamycin, and ossamycin.
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Production, Taxonomy, Isolation, Physico-chemical Characterization and Biological Activity
PRAMATHESH S. PATEL, STELLA HUANG, SUSAN FISHER, DOLORES PIRNIK, CAROL ...
1995 Volume 48 Issue 9 Pages
997-1003
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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Bacillaene, a novel polyene antibiotic, was discovered and isolated from fermentation broths of a strain of
Bacillus subtilis. The novel antibiotic has a nominal molecular weight of 580 and an empirical formula of C
35H
48O
7. Bacillaene is active against a broad spectrum of bacteria in agar-plate diffusion assays. Studies
in vitro indicate that the antibiotic inhibits prokaryotic protein synthesis but not eukaryotic protein synthesis. Cell survival studies performed with strains of
Escherichia coli indicate that the antibiotic is a bacteriostatic agent.
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NAOYUKI FUKUCHI, KAZUO FURIHATA, JIRO NAKAYAMA, TOSHINARI Goudo, SEIJI ...
1995 Volume 48 Issue 9 Pages
1004-1010
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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In the course of screening search for plant growth regulators, a culture filtrate of
Streptomyces graminofadens 3C02 was found to inhibit the growth of lettuce seedlings. The active substances, named rotihibin A (
1) and B (
2), were revealed to be lipo-peptidal compounds. Rotihibins inhibit growth of various plants at below 1 μg/ml, but do not show lethal activity even at higher doses.
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Production and Biohydroxylation of Grisorixin by Nigericin-producing Streptomyces hygroscppicus NRRL B-1865
JAMAL MOUSLIM, ANNIE CUER, LUCIEN DAVID, JEAN-CLAUDE TABET
1995 Volume 48 Issue 9 Pages
1011-1014
Published: September 25, 1995
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With addition of methyl oleate, the increased yield of antibiotic production by nigericin-producing
Streptomyces hygroscopicus NRRL B-1865 also resulted in the isolation of three additional polyether antibiotics. Two of these are abierixin and epinigericin, as new antibiotics. The third antibiotic is grisorixin. The production of both abierixin (opened ring A and 30-CH
2OH) and grisorixin (ring A and 30-CH
3) poses the problem of the identity of the last pathway precursor of the major metabolite, nigericin (ring A and 30-CH
2OH). Transformation experiments of abierixin by
S. hygroscopicus gave negative results. Hydroxylation of grisorixin to nigericin by
S. hygroscopicus represents the final step in nigericin biosynthesis.
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SENJI TAKAHASHI, KENICHI UCHIDA, AKIRA NAKAGAWA, YOKO MIYAKE, MASATSUN ...
1995 Volume 48 Issue 9 Pages
1015-1020
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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The biosynthesis of lactacystin, a new microbial metabolite which induces differentiation of neuroblastoma cells, was studied by the feeding experiments of various
13C-labeled compounds and NMR spectroscopic analysis. The feeding experiments showed that lactacystin consists of three biosynthetic units, namely isobutyrate (and/or L-valine), L-leucine and L-cysteine. The C
10 unit containing γ-lactam moiety arises by a condensation between methylmalonic semialdehyde and C
α position of L-leucine, followed by intramolecular cyclization. Two diastereotopic methyls, C-11 and C-12 of lactacystin were found to originate from the
pro-R and
pro-S methyls of leucine, respectively, as shown by incorporating a new type of chiral
13C-labeled L-leucine.
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HIROSHI YAMAKI, MOTOWO NAKAJIMA, HIROYUKI SEIMIYA, HIDEYUKI SAYA, MASA ...
1995 Volume 48 Issue 9 Pages
1021-1026
Published: September 25, 1995
Released on J-STAGE: April 19, 2006
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Geldanamycin is an antibiotic that preferentially inhibits Gl/S transition and causes G2/M arrest in human leukemia HL-60 cells. With it, we selectively inhibited recombinant Src tyrosine kinase without significantly inhibiting protein kinase A. The perturbation of cell cycling by geldanamycin was accompanied by marked suppression of c-MYC expression.
In contrast to this, pRB expression was remarkably enhanced by geldanamycin. In the untreated HL-60 cells, c-MYC was apparently enriched in nuclear matrix preparation, and significant amounts of hyperphosphorylated pRB, p70 and p40 proteins were observed to associate with the nuclear matrix. The amounts of these proteins associated with the nuclear matrix, however, were markedly decreased by treatment with geldanamycin. This finding suggests that the association of c-MYC, hyperphosphorylated pRB, p70 and p40 proteins with the nuclear matrix is essential in cell cycling, especially in Gl/S and G2/M progressions, and that this association is a part of signal transduction pathway in Src kinase activation.
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FUSAHIRO HIGASHITANI, KOUICHI NISHIDA, AKIO HYODO, MATSUHISA INOUE
1995 Volume 48 Issue 9 Pages
1027-1033
Published: May 25, 1995
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When
Enterobacter cloacae,
Citrobacter freundii, and
Proteus vulgaris were treated with piperacillin (PIPC) in combination with tazobactam (TAZ), the
in vitro frequency of emergence of resistant strains (β-lactamase producing mutants) was lower than with PIPC or ceftazidime (CAZ) treated bacteria. In a mouse intraperitoneal infection model caused by
E. cloacae, β-lactamase derepressed mutants were detected following therapy with PIPC or CAZ, although no derepressed mutants were detected after treatment with PIPC in combination with TAZ. This suppression of the selection of derepressed mutants, which produce large amounts of β-lactamases, by the combination of TAZ and PIPC suggests that the combination delays the increase of resistant mutants compared with PIPC alone.
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JAN PAWLAK, PAWEL SOWINSKI, EDWARD BOROWSKI, PIERLUIGI GARIBOLDI
1995 Volume 48 Issue 9 Pages
1034-1038
Published: September 25, 1995
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The gross structure of perimycin A was revised: the position of the keto group was changed from C-13 to C-5. The Stereostructure of perimycin A was established based upon NMR studies.
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ENRICO SELVA, PIETRO FERRARI, MICHAEL KURZ, PAOLO TAVECCHIA, LUIGI COL ...
1995 Volume 48 Issue 9 Pages
1039-1042
Published: September 25, 1995
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ANDREAS FREDENHAGEN, CHRISTOF ANGST, HEINRICH H. PETER
1995 Volume 48 Issue 9 Pages
1043-1045
Published: September 25, 1995
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HONG-WOO LEE, EUNG-NAM KIM, HOE-JOO SON, KYE-KWANG KIM, JOON-KYUM KIM, ...
1995 Volume 48 Issue 9 Pages
1046-1048
Published: September 25, 1995
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Synthesis and Antibacterial Activity of 7β-[(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-cephalosporin Derivatives Bearing Various Quaternary Ammonium Methyl Groups at the 3 Position
HIDENORI OHKI, KOHJI KAWABATA, SHINYA OKUDA, TOSHIAKI KAMIMURA, KAZUO ...
1995 Volume 48 Issue 9 Pages
1049-1051
Published: September 25, 1995
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RYUJU HASHIMOTO, SENJI TAKAHASHI, KUNIKATSU HAMANO, AKIRA NAKAGAWA
1995 Volume 48 Issue 9 Pages
1052-1054
Published: September 25, 1995
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