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XIII. ISOLATION AND STRUCTURES OF NOVEL FERMENTATION PRODUCTS FROM Micromonospora griseorubida (FERM BP-705)
KENJI KINOSHITA, SATOSHI TAKENAKA, HIDEAKI SUZUKI, TOSHIRO MOROHOSHI, ...
1992 Volume 45 Issue 1 Pages
1-9
Published: January 25, 1992
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Novel 16-membered macrolide antibiotics, mycinamicins IX, XII, XIII, XIV, XV, XVI, XVII and XVIII have been isolated from the culture filtrate of
Micromonospora griseorubida (FERM BP-705). Fermentation, isolation, structure determination and biosynthetic consideration of these mycinamicin analogs are described.
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TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL ACTIVITY
NOZOMI KATAYAMA, YUKIMASA NOZAKI, SHIGETOSHI TSUBOTANI, MASAHIRO KONDO ...
1992 Volume 45 Issue 1 Pages
10-19
Published: January 25, 1992
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A Gram-negative bacterium was found to produce new antibacterial antibiotics, sperabillins A, B, C and D, and the producing bacterium was characterized and identified as
Pseudomonas fluorescens YK-437. Sperabillins were isolated by column chromatographies using cation-exchange resins, activated carbon and cation-exchange Sephadex, and preparative reverse-phase HPLC. Sperabillins showed antibacterial activity against Gram-negative and Gram-positive bacteria including antibiotic-resistant strains of
Pseudomonas aeruginosa and
Staphylococcus aureus. Sperabillin A inhibited DNA, RNA, protein, and cell wall biosynthesis in
Escherichia coli. Sperabillins showed good protective effects in experimentally infected mice.
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MINORU HANADA, KOKO SUGAWARA, YUJI NISHIYAMA, HIDEO KAMEI, MASAMI HATO ...
1992 Volume 45 Issue 1 Pages
20-28
Published: January 25, 1992
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Streptomyces cucumerosporus strain L703-4 (ATCC 53784) produces a new 4-methyl-3-hydroxyanthraniloylpentapeptide lactone for which we have proposed the name protactin, in addition to several actinomycin components. Protactin is rather resistant to air oxidation but it can be converted to a new actinomycin, actinomycin Zp by ferricyanide oxidation. Actinomycin Zp possesses
in vitro antibacterial activity and
in vivo antitumor activity against P-388 leukemia in mice.
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CLAVICORONIC ACID, A NOVEL INHIBITOR OF REVERSE TRANSCRIPTASES FROM Clavicorona pyxidata (PERS. EX FR.) DOTY
GERHARD ERKEL, TIMM ANKE, ALBERTO GIMENEZ, WOLFGANG STEGLICH
1992 Volume 45 Issue 1 Pages
29-37
Published: January 25, 1992
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A novel inhibitor of RNA-directed DNA-polymerases was isolated from fermentations of
Clavicorona pyxidata. Its structure was elucidated by spectroscopic methods. Clavicoronic acid (
1) is a noncompetitive inhibitor of avian myeloblastosis virus (
Ki 130 μM) and Moloney murine leukemia virus (
Ki 68μM) reverse transcriptases. In permeabilized cells and isolated nucleic DNA- and RNA-synthesis are not affected. Clavicoronic acid markedly inhibits the multiplication of vesicular stomatitis virus in baby hamster kidney cells by interfering with this virus's RNA-directed RNA-polymerase.
1 exhibits no cytotoxic and very weak antimicrobial activities.
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I. TAXONOMY AND FERMENTATION OF THE PRODUCING CULTURE; ISOLATION AND STRUCTURES OF CINATRINS
HIROSHI ITAZAKI, KAZUO NAGASHIMA, YOSHIMI KAWAMURA, KOICHI MATSUMOTO, ...
1992 Volume 45 Issue 1 Pages
38-49
Published: January 25, 1992
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Cinatrins A, B, C
1, C
2 and C
3, a family of phospholipase A
2 inhibitors were isolated from the fermentation broth of
Circinotrichum falcatisporum RF-641. They were found to be novel spiro-γ-dilactones and γ-lactones derived from 1, 2, 3, 5-tetra or 1, 2, 3(or 1, 2, 4)-trihydroxypentadecane1, 2, 3-tricarboxylic acids. Structures were elucidated by MS and NMR studies and chemical transformations. The structure of cinatrin C
3 was confirmed by X-ray crystallographic analysis, and its absolute configuration was determined by comparison of the CD spectra with related compounds.
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II. BIOLOGICAL ACTIVITIES
KAZUSHIGE TANAKA, HIROSHI ITAZAKI, TADASHI YOSHIDA
1992 Volume 45 Issue 1 Pages
50-55
Published: January 25, 1992
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Cinatrins A, B and C
3 inhibited phospholipase A
2 purified from rat platelets in a dose-dependent manner. Cinatrin C
3, the most potent component (IC
50 70μM), was noncompetitive with a
Ki value of 36 μM. Cinatrins B and C
3 also inhibited both porcine pancreas and
Naja naja venom phospholipase A
2. Inhibition of rat platelet phospholipase A
2 by cinatrin C
3 was independent of Ca
2+ and substrate concentration. Comparison with duramycin, another phospholipase A
2 inhibitor, displayed inhibition dependent on substrate concentration when phosphatidylethanolamine was the substrate. These results indicate that the inhibition of phospholipase A
2 by cinatrin C
3 may result from direct interaction with the enzyme.
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I. STRAIN DESCRIPTION, FERMENTATION, ISOLATION AND PROPERTIES
SUSANNE GRABLEY, ERNOLD GRANZER, KLAUS HÜTTER, DIETER LUDWIG, MAR ...
1992 Volume 45 Issue 1 Pages
56-65
Published: January 25, 1992
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A family of new 10-membered lactones was detected by chemical screening. Taxonomic studies and fermentation conditions of the producing organisms, which belong to the species
Penicillium simplicissimum and
Penicillium corylophilum, are presented. The isolation as well as physico-chemical data of the new compounds named decarestrictines A to D are reported.
In vitro testing using the HEP-G2 cell assay showed the decarestrictines to be inhibitors of cholesterol biosynthesis, which could be confirmed
in vivo. In addition to the decarestrictines from
P. corylophilum epoxyagroclavine-I (
1) was isolated.
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II. STRUCTURE ELUCIDATION OF THE DECARESTRICTINES A TO D
AXEL GÖHRT, AXEL ZEECK, KLAUS HÜTTER, REINHARD KIRSCH, HEINZ ...
1992 Volume 45 Issue 1 Pages
66-73
Published: January 25, 1992
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The structures of the novel 10-membered lactones, named decarestrictines A
1/A
2 (
1/
2), B (
3), C
1/C
2 (
5/
6) and D (
7), are presented. The structures of these secondary metabolites, isolated from different
Penicillium species, were established by spectroscopic analysis and confirmed by X-ray analysis of
7 and a derivative of
3 leading to the stereochemical information. The decarestrictines vary in the oxygenation pattern between C-3 and C-7 and show structural similarities to known lactones from other fungi.
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I. TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
SUSUMU MIYATA, MICHIZANE HASHIMOTO, YUKO MASUI, MASAMI EZAKI, SHIGEHIR ...
1992 Volume 45 Issue 1 Pages
74-82
Published: January 25, 1992
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WS-7338 A, B, C and D, novel endothelin receptor antagonists, have been isolated from fermentation broth of
Streptomyces sp. No. 7338. These antagonists were purified from the culture mycelium by extraction with acetone, followed by carbon column chromatography and HPLC. Among them, WS-7338 B showed good activity in an endothelin receptor binding assay with an IC
50 of2.7×10
-7M.
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II. BIOLOGICAL CHARACTERIZATION AND PHARMACOLOGICAL CHARACTERIZATION OF WS-7338 B
SUSUMU MIYATA, MICHIZANE HASHIMOTO, KEIKO FUJIE, MOTOAKI NISHIKAWA, SU ...
1992 Volume 45 Issue 1 Pages
83-87
Published: January 25, 1992
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WS-7338, produced by
Streptomyces sp. No. 7338, was found to be a competitive and specific antagonist against ET-1 receptors in
in vitro studies and WS-7338 B is also active
in vivo. Furthermore, WS-7338 B was a specific antagonist for vascular ET-1 receptors (ET
A receptors) and significantly prevented the accumulation of intracellular inositol 1, 4, 5-triphosphate (IP
3) in endothelin treated rat aorta tissues.
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SHINICHIRO TOKI, KATSUHIKO ANDO, MAYUMI YOSHIDA, ISAO KAWAMOTO, HIROSH ...
1992 Volume 45 Issue 1 Pages
88-93
Published: January 25, 1992
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A novel compound, ES-242-1, which binds to a site on
N-methyl-D-aspartate (NMDA) receptor that is coupled to the channel domain, was isolated from the culture broth of a fungus,
Verticillium sp. SPC-15898. ES-242-1 inhibited the [
3H]thienyl cyclohexylpiperidine ([
3H]TCP) binding to rat crude synaptic membrane fractions with an IC
50 value of 116 nM, but did not inhibit the [
3H]kainate binding to its receptor, which is another subtype of the excitatory amino acid receptor.
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ARTHUR A. PATCHETT, DAVID TAUB, OTTO D. HENSENS, ROBERT T. GOEGELMAN, ...
1992 Volume 45 Issue 1 Pages
94-102
Published: January 25, 1992
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The conversion of [2-deutero-3-fluoro-D-Ala
8]cyclosporin A (
1) to a dehydroalanine analog [Δ-Ala
8]cyclosporin A (
2) was achieved with lithium diisopropylamide in THF at low temperature. This dehydro compound is a useful intermediate for the preparation of position 8 analogs of cyclosporin A formed from it by the conjugate addition of thiol compounds. NMR conformational studies have provided evidence for the restoration of D-stereochemistry in the modified Ala
8 residues. The preparation of several of these cyclosporin analogs and their bioactivities are described.
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ISAO SUGIYAMA, YUUKI KOMATSU, HIROSHI YAMAUCHI
1992 Volume 45 Issue 1 Pages
103-112
Published: January 25, 1992
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The synthesis and
in vitro antibacterial activity of a series of 7-[(
Z)-2-aminoaryl-2-oxyiminoacetamido]-3-ammoniomethyl-3-cephems are described. Variation of an oxyimino moiety with aminoaryl at the C-7 side chain and a quaternary ammonium moiety at the C-3 side chain were examined and structure-activity relationships were studied.
E1040, the 3-(4-carbamoylquinuclidinio)methyl derivative of the 7-α-methoxyimino series of aminothiadiazolyl cephalosporins, exhibited excellent activity against both Gram-positive and Gram-negative bacteria, particularly against
Pseudomonas aeruginosa, and possessed high stability to β-lacctamases.
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NOBUO SAKATA, KAYOKO S. TSUCHIYA, YUKARI MORIYA, HIDEMI HAYASHI, MAKOT ...
1992 Volume 45 Issue 1 Pages
113-117
Published: January 25, 1992
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An antitumor antibiotic C-1027, a complex protein consisting of an apoprotein and a non-covalently bound chromophore, showed some aminopeptidase activity, 1/15 (on the basis of activity per mg protein) that of porcine kidney enzyme [E.C. 3.4.11.2] by use of L-phenylalanyl 4-methyl-coumaryl-7-amide as the substrate. Neither the apoprotein alone nor the chromophore alone were active. Amastatin and bestatin but not leupeptin inhibited the activity. The enzyme activity of the holo-antibiotic, as opposed to that of the porcine kidney enzyme, was readily lost by UV irradiation, indicating that the intact structure of the chromophore was needed to maintain the native conformation of the holo-antibiotic. The cytotoxicity of the holo-antibiotic, but not that of the chromophore, to Ehrlich carcinoma cells
in vitro was reduced to 1/5 by 1 μg/ml of amastatin which alone had no effect on cell growth. The porcine aminopeptidase was not cytotoxic at all even at higher concentrations (higher enzyme activities/ml). Amastatin possibly occupied the catalytic domain of the holo-antibiotic, interfering with the binding of the holo-antibiotic with some cell-surface protein(s). Amastatin did not inhibit the holo-antibiotic to cleave isolated DNA.
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I. DESMETHYLATION OF FK506 AND IMMUNOMYCIN (FR 900520) BY Actinoplanes sp. ATCC 53771
TOM S. CHEN, BYRON H. ARISON, LINDA S. WICKER, EDWARD S. INAMINE, RICH ...
1992 Volume 45 Issue 1 Pages
118-123
Published: January 25, 1992
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The immimosuppressants FK506 and FR 900520 were desmethylated by
Actinoplanes sp. ATCC 53771 to yield various
O-desmethylated products. The products were isolated and purified by solvent extraction and HPLC chromatography, and identified by NMR and MS spectroscopy.
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KAZUO SHIN-YA, AKIRA SHIMAZU, YOICHI HAYAKAWA, HARUO SETO
1992 Volume 45 Issue 1 Pages
124-125
Published: January 25, 1992
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MASUO MORISAKI, TADASHI ARAI
1992 Volume 45 Issue 1 Pages
126-128
Published: January 25, 1992
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MASAMI OGASAWARA, MASAMI HASEGAWA, YASUTARO HAMAGISHI, HIDEO KAMEI, TO ...
1992 Volume 45 Issue 1 Pages
129-132
Published: January 25, 1992
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OTTO D. HENSENS, RAYMOND F. WHITE, ROBERT T. GOEGELMAN, EDWARD S. INAM ...
1992 Volume 45 Issue 1 Pages
133-135
Published: January 25, 1992
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RYUICHI SAWA, YOSHIKAZU TAKAHASHI, SAKIKO ITOH, KAZUO SHIMANAKA, NAOKO ...
1992 Volume 45 Issue 1 Pages
136-139
Published: January 25, 1992
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TATSUO OHTSUKA, TSUTOMU KUDOH, NOBUO SHIMMA, HIROMICHI KOTAKI, NOBORU ...
1992 Volume 45 Issue 1 Pages
140-143
Published: January 25, 1992
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SHUNJI KAGEYAMA, TSUTOMU TSUCHIYA, SUMIO UMEZAWA, TOMIO TAKEUCHI
1992 Volume 45 Issue 1 Pages
144-146
Published: January 25, 1992
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