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I. TAXONOMY, FERMENTATION, ISOLATION, CHARACTERIZATION AND BIOLOGICAL ACTIVITIES
TSUTOMU KAMIYAMA, TAKAYUKI UMINO, NORIKO FUJISAKI, KUMIKO FUJIMORI, TO ...
1993 Volume 46 Issue 7 Pages
1039-1046
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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Tetrafibricin is a novel fibrinogen receptor antagonist produced by
Streptomyces neyagawaensis NR0577. It was isolated from the culture broth by Diaion HP-21 adsorption, MeOH extraction, MCI GEL CHP-20P column chromatography, preparative HPLC and Toyopearl HW-40 SF column chromatography. The physico-chemical properties of tetrafibricin indicated that the structure of tetrafibricin is different from the known peptide fibrinogen receptor antagonists and closely related to the polyene macrolide antibiotics. Tetrafibricin strongly inhibited the binding of fibrinogen to its receptors with an IC
50 of 46 nM. It also inhibited ADP-, collagen-, and thrombin-induced aggregation of human platelets with IC
50s of 5.6, 11.0 and 7.6μM, respectively.
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II. STRUCTURAL ELUCIDATION
TSUTOMU KAMIYAMA, YOSHIKO ITEZONO, TAKAYUKI UMINO, TOMOKO SATOH, NOBOR ...
1993 Volume 46 Issue 7 Pages
1047-1054
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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The structure of tetrafibricin, a novel and potent fibrinogen receptor antagonist isolated from the culture broth of
Streptomyces neyagawaensis NR0577, was determined. Tetrafibricin has a unique structure containing primary amine, conjugated tetraenoic acid, and polyhydroxy functionalities that is biosynthetically related to the polyene macrolide antibiotics.
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I. TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES
YASUHIRO HORI, YUKIKO ABE, MASAMI EZAKI, TOSHIO GOTO, MASAKUNI OKUHARA ...
1993 Volume 46 Issue 7 Pages
1055-1062
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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New non-steroidal estrogen-receptor antagonists, R1128 A, B, C and D, were isolated from the cultured broth of
Streptomyces sp. No. 1128 by solvent extraction, silica gel chromatography, reverse phase chromatography and preparative HPLC. These compounds inhibited estrogen binding to its receptor. The IC
50 values of R1128 A, B, C and D for partially purified rat uterine cytosol receptor were 1.1×10
-7M, 1.2×10
-7M, 2.6×10
-7M and 2.7 × 10
-7M, respectively.
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II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION
YASUHIRO HORI, SHIGEHIRO TAKASE, NOBUHARU SHIGEMATSU, TOSHIO GOTO, MAS ...
1993 Volume 46 Issue 7 Pages
1063-1068
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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R1128 A, B, C and D, new non-steroidal estrogen-receptor antagonists, were isolated from the cultured broth of
Streptomyces sp. No. 1128. Their structures were elucidated to be l, 3, 6-trihydroxy-8-alkylanthraquinones on the basis of their physico-chemical properties and spectroscopic data.
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III. PHARMACOLOGICAL PROPERTIES AND ANTITUMOR ACTIVITIES
YASUHIRO HORI, YUKIKO ABE, MAKOTO NISHIMURA, TOSHIO GOTO, MASAKUNI OKU ...
1993 Volume 46 Issue 7 Pages
1069-1075
Published: July 25, 1993
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R1128 B (l, 3, 6-trihydroxy-8-
n-butylanthraquinone), a new antibiotic produced by
Streptomyces sp. No. 1128, inhibited estrogen binding to its receptor. The IC
50 value of R1128B for partially purified rat uterine cytosol receptor was 1.2×10
-7 M. However, the IC
50 value of Rl 128 B against androgen-receptor binding was about 50-fold greater than that against estrogen-receptor binding. Rl 128 B was a competitive inhibitor against estrogen-receptor binding. R1128 B inhibited the growth of estrogen-responsive human mammary adenocarcinoma MCF-7 cells in soft agar. This inhibition, however, was reversed when estradiol was added to the culture medium. Rl 128 B showed antitumor activities against MCF-7 both xenografted to nude mice and implanted in subrenal capsule of mice (SRC assay). The potency of R1128 B was about 8-fold lower than that of tamoxifen both
in vitro and
in vivo.
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KAZUTOSHI SHINDO, MASARU KAMISHOHARA, ATSUO ODAGAWA, MICHIKO MATSUOKA, ...
1993 Volume 46 Issue 7 Pages
1076-1081
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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A new antitumor antibiotic vicenistatin was isolated from the culture broth of
Streptomyces sp. HC34. The structure of vicenistatin was elucidated by NMR spectral analysis. Vicenistatin exhibited antitumor activity against human colon carcinoma Co-3 in the xenograft model.
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FRIEDRICH MAYERL, QI GAO, STELLA HUANG, STEVEN E. KLOHR, JAMES A. MATS ...
1993 Volume 46 Issue 7 Pages
1082-1088
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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Eupenifeldin was isolated from cultures of
Eupenicillium brefeldianum ATCC 74184 by extraction and crystallization. The compound was identified as a pentacyclic bistropolone on the basis of spectral data and its complete structure was established by single-crystal X-ray analysis. The compound is cytotoxic against the HCT-116 cell line and has
in vivo antitumor activity in the P388 leukemia model.
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I. TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL AND BIOLOGICAL PROPERTIES
MASASHI UEKI, KEIICHI UENO, SHINJI MIYADOH, KEIICHI ABE, KOZO SHIBATA, ...
1993 Volume 46 Issue 7 Pages
1089-1094
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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A new benzoxazole, UK-1, was isolated from the mycelial cake of an actinomycete strain 517-02. Based on morphological, cultural and physiological characteristics, strain 517-02 was seemed to be a close relative of
Streptomyces morookaense. UK-1 showed potent cytotoxic activity against B16, HeLa and P388 cells and did not show any antimicrobial activity.
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II. STRUCTURAL ELUCIDATION
Kozo SHIBATA, MASARU KASHIWADA, MASASHI UEKI, MAKOTO TANIGUCHI
1993 Volume 46 Issue 7 Pages
1095-1100
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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The structure of UK-1 isolated from the mycelium of
Streptomyces sp. 517-02 was elucidated to be a novel benzoxazole dimmer derivative (
1) on the basis of spectroscopic methods.
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JENS BREINHOLT, GEORG W. JENSEN, RUBY I. NIELSEN, CARL E. OLSEN, JENS ...
1993 Volume 46 Issue 7 Pages
1101-1108
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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Three macrocyclic polylactones have been isolated from
Penicillium verruculosum. Two were found to be novel and the third to be identical with NG-012
1). Their structures were elucidated by spectroscopic and chemical methods. A full assignment of
1H- and
13C-resonances in acetone-
d6 are given for all three compounds. The compounds show antifungal activity.
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TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES, STRUCTURE ELUCIDATION AND BIOLOGICAL ACTIVITY
VINOD R. HEGDE, MAHESH G. PATEL, VINCENT P. GULLO, ANN C. HORAN, ARTHU ...
1993 Volume 46 Issue 7 Pages
1109-1115
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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A novel natural product (
1), with antifungal activity was isolated from the culture broth of an actinomadurae. The active compound was separated from broth by
n-butanol extraction and purified by silica gel and multicoil counter current chromatography. Physico-chemical data suggested the structure of this compound to be a novel macrolactam disaccharide related to Sch 38518 (
3). The structure was determined by spectroscopic studies on the acetate derivative. It was active against
Candida spp. (MIC's, 4-64μg/ml) but less active than the monosaccharide, Sch 38518 (MIC's, 1-16μg/ml).
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OSAMU ANDO, MUTSUO NAKAJIMA, KIYOSHI HAMANO, KAZUKO ITOI, SHUJI TAKAHA ...
1993 Volume 46 Issue 7 Pages
1116-1125
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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Trehalamine, (3a
R, 4
R, 5
S, 6
S, 6a
S)-2-amino-4-(hydroxymethyl)-3a, 5, 6, 6a-tetrahydro-4
H-cyclopent[
d]oxazole-4, 5, 6-triol (
1) and D-glucose were obtained by acid hydrolysis of trehazolin (
3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded an aminocyclitol, (1
R, 2
S, 3
R, 4
S, 5
R)-5-ammo-l-(hydroxymethyl)cyclopentane-1, 2, 3, 4-tetraol (
2). Trehalamine, the aglycon of trehazolin, was also found in the culture broths of two trehazolin producing strains,
Micromonospora sp. SANK 62390 and
Amycolatopsis sp. SANK 60791. These trehazolin related compounds trehalamine (
1) and
2 were poor inhibitors of trehalase (
1; IC
50 1.8 × 10
-4 M,
2; > 5.0 × 10
-4 M). On the other hand they inhibited more potently rat intestinal sucrase (
1; IC
50 6.8 × 10
-5M) and sweet almond β-glucosidase (
2; IC
50 5.6× 10
-6M) than trehazolin.
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FRANK PETERSEN, HANS ZÄHNER, JÖRG W. METZGER, STEFAN FREUND, ...
1993 Volume 46 Issue 7 Pages
1126-1138
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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During germination spores of
Streptomyces viridochromogenes NRRL B-1551 excrete a compound, germicidin, which has an inhibitory effect on the germination of its own arthrospores at a concentration as low as 200 pM (40pg/ml). At higher concentrations germicidin inhibits porcine Na
+/K
+-activated ATPase and retards the germination of the cress
Lepidium sativum. Germicidin is the first known autoregulative inhibitor of spore germination in the genus
Streptomyces and was isolated from the supernatant of germinated spores, but also from the supernatant of the submerged culture.
Spectroscopic analysis and derivatization reactions revealed germicidin to be 6-(2-butyl)-3-ethyl4-hydroxy-2-pyrone (C
11H
16O
3). Crude isolates of germicidin from the supernatant of submerged culture, but not from the spores, contained a second, structurally very similar compound (C
10H
14O
3), in which in contrast to germicidin a 2-propyl instead of the 2-butyl chain was bound to C-6 and which did not show any activity in the germination and ATPase assay. The germination assay was evaluated as a new screening model for specifically active compounds.
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II. ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE ELUCIDATION
KAZUO KUMAGAI, AKIO FUKUI, SHIN TANAKA, MASAHIKO IKEMOTO, KOICHI MORIG ...
1993 Volume 46 Issue 7 Pages
1139-1144
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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A new macrolide antibiotic, PC-766B, was isolated from the cells of
Nocardia brasiliensis SC-4710 by acetone extraction, and purified by gel filtration, silica gel chromatography, HPLC and TLC. The structure of PC-766B was determined by NMR spectral analysis to be a new class of the hygrolidin family antibiotics. PC-766B had a 16-membered macrocyclic lactone ring, a 6-membered hemiketal ring and a 2-deoxy-D-rhamnose moiety. DL-α-Tocopherol, known as an antioxidant agent, significantly improved the stability of PC-766B and prevented the decomposition of PC-766B during the storage of the antibiotic.
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SEIJI HORI, KEIJI KANEMITSU, JINGORO SHIMADA
1993 Volume 46 Issue 7 Pages
1145-1148
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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Cephalosporins have been well known to have potent convulsant activity. We studied the mechanism of the convulsions induced by cephalosporins. Cefazolin, cephaloridine, cefpirome and cefmetazole inhibited the receptor binding of γ-aminobutyric acid (GABA), an inhibitory transmitter in the mammalian central nervous system. As fluoroquinolones also inhibited GABA receptor binding and this inhibition was enhanced in the presence of non-steroidal anti-inflammatory drugs (NSAIDs), we studied the effect of cephalosporins on GABA receptor binding in the presence of NSAIDs. The inhibitory activity of cephalosporins was not enhanced in the presence of NSAIDs. These results suggested that cephalosporins might induce convulsions through the inhibition of GABA receptor binding, and that concurrent administration of cephalosporins and NSAIDs might not enhance the convulsant activity of cephalosporins.
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I. ISOLATION AND STRUCTURE DETERMINATION OF TAUTOMERIC COMPOUNDS
Y. NAMIKI, N. KIHARA, S. KODA, K. HANE, T. YASUDA
1993 Volume 46 Issue 7 Pages
1149-1155
Published: July 25, 1993
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Tautomeric phenomenon was observed in the HPLC chromatogram obtained from a novel potent immunosuppressant, FK506, in ethanol solution. Two tautomeric compounds derived from FK506 were isolated and purified by HPLC. Their structures were elucidated by spectral analyses. The mechanisms for this tautomerization were also established based on the results of structure analysis.
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IV. STRUCTURE-ACTIVITY RELATIONSHIPS OF DELAMINOMYCINS AND DERIVATIVES
MITSUHIRO UENO, MASAHIDE AMEMIYA, KATSUHISA YAMAZAKI, MASATOMI IIJIMA, ...
1993 Volume 46 Issue 7 Pages
1156-1162
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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Delaminomycins A, B, C and their derivatives were prepared and investigated biological activities of them. Among these compounds, spiro compounds (
A2,
B2 and
C2) showed stronger inhibitory activity than natural products (
A1,
B1 and
C1) on B16 melanoma cells adhesion assay and Con A-induced proliferation of murine splenic lymphocytes assay. In MLCR and antimicrobial assay, however,
A1,
B1 and
C1 showed more potent inhibitory activity than spiro compounds (
A2,
B2 and
C2).
On the other hand, as to C-5' substituents of pyrrolidine ring, the order of inhibitory activity was R=OH>R=OCH
3>R=H on Con A-induced proliferation of murine splenic lymphocytes assay. In MLCR and antimicrobial assay, however, the order of inhibitory activities were R=H>R=OCH
3>R=OH.
Inhibitory activities of
A4 which was lacked pyrrolidine ring were reduced on B16 melanoma cells adhesion assay and on cytotoxicity against tumor cells
in vitro in comparison with those of
A1.
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XII. A FACILE SYNTHESIS OF CLARITHROMYCIN (6-O-METHYLERYTHROMYCIN A) VIA 2'-SILYLETHERS OF ERYTHROMYCIN A DERIVATIVES
YOSHIAKI WATANABE, TAKASHI ADACHI, TOSHIFUMI ASAKA, MASATO KASHIMURA, ...
1993 Volume 46 Issue 7 Pages
1163-1167
Published: July 25, 1993
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SATOSHI OMURA, HIROSHI TOMODA, YOUNG KOOK KIM, HIROYUKI NISHIDA
1993 Volume 46 Issue 7 Pages
1168-1169
Published: July 25, 1993
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JONG KOO PARK, KAORU SAKAI, HARUO OGAWA, KEIJI HASUMI, AKIRA ENDO
1993 Volume 46 Issue 7 Pages
1170-1172
Published: July 25, 1993
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NOBORU FUJII, YOSHINORI YAMASHITA, SHIGERU CHIBA, YOUICHI UOSAKI, YUTA ...
1993 Volume 46 Issue 7 Pages
1173-1174
Published: July 25, 1993
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G. BERETTA, F. LE MONNIER, E. SELVA, F. MARINELLI
1993 Volume 46 Issue 7 Pages
1175-1177
Published: July 25, 1993
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TOSHIAKI SUNAZUKA, NORIKO TABATA, TOHRU NAGAMITSU, HIROSHI TOMODA, SAT ...
1993 Volume 46 Issue 7 Pages
1178-1180
Published: July 25, 1993
Released on J-STAGE: April 19, 2006
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