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KAZURO SHIOMI, HIKARU NAKAMURA, HIRONOBU IINUMA, HIROSHI NAGANAWA, TOM ...
1987 Volume 40 Issue 9 Pages
1213-1219
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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Napyradiomycins A2 and B4, new members of the napyradiomycins, have been isolated from the culture broth of
Chainia rubra MG802-AF1. The structure of napyradiomycin A2 was elucidated as 16-hydroxy-17-methylenenapyradiomycin A1 by NMR studies. The absolute structure of napyradiomycin B4 was determined as 13-hydroxy-13-methylnapyradiomycin B1 by X-ray crystallography and therefore the configuration of C(4a) in other napyradiomycins is assumed as the
R configuration. The geometrical isomerism of napyradiomycin C1 was estimated as 12
E and 16
E by nuclear Overhauser effect experiments.
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MASAYUKI TAKIZAWA, SHIGETOSHI TSUBOTANI, SEIICHI TANIDA, SETSUO HARADA ...
1987 Volume 40 Issue 9 Pages
1220-1230
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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A new pyrrole-amidine antibiotic TAN-868 A was isolated from the culture broth of
Streptomyces idiomorphus sp. nov. Its chemical structure was determined by spectroscopic analyses and degradation studies to be 4-[(2
S, 4
R)-4-hydroxy-5-iminoprolyl]amino-
N-(2-amidinoethenyl)-2-pyrrolecarboxamide. The antibiotic is active against bacteria, fungi and a protozoan, and has cytotoxic activity against murine tumor cells. DNA thermal denaturation studies suggest that TAN-868 A preferentially interacts with AT rich regions of doublestranded DNA.
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I. TAXONOMY, ISOLATION AND CHARACTERIZATION
TAKENORI ISHIMARU, TSUNEO KANAMARU, KAZUHIKO OHTA, HISAYOSHI OKAZAKI
1987 Volume 40 Issue 9 Pages
1231-1238
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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Fibrostatins, potent inhibitors of prolyl hydroxylase, were isolated as orange crystals from the culture broth of strain No. 23924, which was identified as
Streptomyces catenulae subsp.
griseospora.
In vitro inhibitory activity (ID
50 value) of fibrostatins A, B, C, D, E and F against prolyl hydroxylase of chick embryos was 23, 39, 29, 180, 10 and 14 A"M, respectively.
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KAZUHIKO OHTA, FUMIKO KASAHARA, TAKENORI ISHIMARU, YOSHIKAZU WADA, TSU ...
1987 Volume 40 Issue 9 Pages
1239-1248
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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The structures of six inhibitors of prolyl hydroxylase, fibrostatins A, B, C, D, E and F produced by a strain of
Streptomyces, were deduced to be
1,
2,
3,
4,
5 and
6, respectively, from chemical and spectroscopic evidence, especially from extensive
13C NMR studies including selective decoupling and low power selective decoupling experiments monitored by
13C-
1H long-range couplings. These compounds are the first naturally occurring 2, 6, 7-or 3, 6, 7-tri-substituted or 2, 3, 6, 7-tetra-substituted 5-hydroxy-1, 4-naphthoquinone inhibitors possessing
N-acetyl-L-cystein-S-yl moieties in the molecule.
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I. FERMENTATION, ISOLATION, AND PHYSICO-CHEMICAL AND BIOLOGICAL CHARACTERISTICS
TORU KINO, HIROSHI HATANAKA, MICHISANE HASHIMOTO, MICHIHISA NISHIYAMA, ...
1987 Volume 40 Issue 9 Pages
1249-1255
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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FK-506, a novel immunosuppressant, has been isolated from the fermentation broth of
Streptomyces tsukubaensis No. 9993 as colorless prism and the molecular formula was determined as C
44H
69NO
12.H
2O. The compound suppressed immune responses
in vitro and
in vivo with mice. This immunosuppressive effect was more potent than that of ciclosporin.
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II. IMMUNOSUPPRESSIVE EFFECT OF FK-506 IN VITRO
TORU KINO, HIROSHI HATANAKA, SUSUMU MIYATA, NORIAKI INAMURA, MICHIHISA ...
1987 Volume 40 Issue 9 Pages
1256-1265
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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The immuno-pharmacological profile of a novel immunosuppressive agent, FK-506 produced by a streptomycete, is presented here. We proceeded to test the effect of the agent on various
in vitro immune systems. It showed that mixed lymphocyte reaction, cytotoxic T cell generation, the production of T cell-derived soluble mediators such as interleukin 2 (IL-2), interleukin 3 and gamma-interferon and the expression of the IL-2 receptor were suppressed by this agent. The IC
50 values of FK-506 and ciclosporin (CS) in all tests were approximately 0.1nM and 10nM, respectively. Therefore, the novel agent, FK-506 suppressed
in vitro immune systems at about hundred times lower concentration than CS.
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I. TAXONOMY, FERMENTATION, ISOLATION AND PHYSICO-CHEMICAL PROPERTIES
HIROYUKI KAWAI, YOICHI HAYAKAWA, MASAYA NAKAGAWA, KAZUO FURIHATA, KEIK ...
1987 Volume 40 Issue 9 Pages
1266-1272
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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Arugomycin (AGM) is a new anthracycline antibiotic produced by strain No. 1098-(Vsb2)AV2 which was identified as
Streptomyces violaceochromogenes. AGM was isolated by solvent extraction, silicic acid chromatography and Sephadex LH-20 column chromatography. Acid treatment of AGM gave the chromophore, named arugorol, which was identified as 4'-
epi-nogalarol, and sugar moieties. AGM inhibited the growth of Gram-positive bacteria and showed antitumor activity against sarcoma S-180 and Ehrlich ascites tumors.
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II. STRUCTURAL ELUCIDATION
HIROYUKI KAWAI, YOICHI HAYAKAWA, MASAYA NAKAGAWA, KAZUO FURIHATA, HARU ...
1987 Volume 40 Issue 9 Pages
1273-1282
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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The structure of arugomycin was determined by chemical degradation, and NMR and mass spectral analyses to be a new anthracycline antibiotic with arugorol (4'-
epi-nogalarol) as the chromophore and two sugar chains comprising diginosyl-decilonitrosyl-2-deoxyfucose, and (4-
O-fumaryl-diginosyl)-diginosyl-2-deoxyfucosyl-diginose.
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III. BIOLOGICAL ACTIVITIES OF ARUGOMYCIN AND ITS ANALOGUES OBTAINED BY CHEMICAL DEGRADATION AND MODIFICATION
AKIHIRO SHIMOSAKA, HIROYUKI KAWAI, YOICHI HAYAKAWA, NOBUYASU KOMESHIMA ...
1987 Volume 40 Issue 9 Pages
1283-1291
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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Biological activities of arugomycin and its analogues obtained by chemical degradation and modification were evaluated. Differences in the sugar moieties affected their biological activities including induction of differentiation of mouse Friend erythroleukemia cells and mouse myeloid leukemia cells, antitumor activities against sarcoma S-180, Ehrlich ascites carcinoma and P388 leukemia, and cytotoxicity against murine leukemia cells. Some relationships were found between the sugar moieties and biological activities.
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MAKOTO SATO, MAKOTO TAKEMURA, SHOHGO ATARASHI, KUNIO HIGASHI, TAKAYASU ...
1987 Volume 40 Issue 9 Pages
1292-1302
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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Thienamycin derivatives (
4) having a cyclic amidine moiety at the C-2 position were prepared. The susceptibility to renal dehydropeptidase-1 and the antimicrobial activity of these compounds were determined. Their structure-activity relationships are also discussed.
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II. CHEMICAL MODIFICATION OF THE SPERMIDINE MOIETY
YOSHIHISA UMEDA, MAKOTO MORIGUCHI, HIROYUKI KURODA, TERUYA NAKAMURA, A ...
1987 Volume 40 Issue 9 Pages
1303-1315
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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Chemical modifications of the spermidine moiety of an antitumor antibiotic, spergualin (
Ia), and the structure-activity relationship are described. Replacement of spermidine with other poly amines decreased the antitumor activity against mouse leukemia LI 210. Analogues containing an oxidized spermidine moiety that probably formed during oxidation with amine oxidase were inactive. Spermidine is indispensable for the antitumor activity. A facile method for the synthesis of glyoxyloyl polyamine, a key intermediate of spergualin-related compounds, is also reported.
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III. NOVEL METHOD FOR SYNTHESIS OF OPTICALLY ACTIVE 15-DEOXYSPERGUALIN AND 15-DEOXY-l 1-O-METHYLSPERGUALIN
YOSHIHISA UMEDA, MAKOTO MORIGUCHI, KATSUSHIGE IKAI, HLROYUKI KURODA, T ...
1987 Volume 40 Issue 9 Pages
1316-1324
Published: September 25, 1987
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Optically active 15-deoxyspergualin (
II) and 15-deoxy-ll-
O-methylspergualin (
IIa) were synthesized, and their antitumor activities were examined. The (-)-enantiomers of both
II and
Ha were active against mouse leukemia LI 210, while the (+)-enantiomers were almost inactive. The optical resolution of the key intermediate, (±)-
N-(7-guanidinoheptanoyl)-α-alkoxyglycine (
VI) was achieved by use of an exopeptidase, serine (acid) carboxypeptidase [EC 3.4.16.1] and (±)-
N-(7-guanidinoheptanoyl)-α-alkoxyglycyl-L-amino acid (
VIII) as the substrate. Considering the enzymatic susceptibility of the substrate (
VIII), we deduced that the absolute configuration of the carbon at 11 (C-11) of the bioactive (-)-enantiomer, and so that of natural spergualin (
I), is
S. This is, to our knowledge, the first report of the use of carboxypeptidase for the resolution of
N-acyl amino acid.
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II. THE SYNTHESIS AND ORAL ACTIVITY OF 7-[R-2-AMINO-2-(3-CHLORO-4-HYDROXYPHENYL)ACETAMIDO]-3-METHYLTHIO-3-CEPHEM-4-CARBOXYLIC ACID AND RELATED COMPOUNDS
KENJI SAKAGAMI, TADAHIRO WATANABE, SHUNZO FUKATSU, HAJIME NITTA, MINOR ...
1987 Volume 40 Issue 9 Pages
1325-1330
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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A series of 3-methylthio-3-cephem-4-carboxylic acids were prepared to test their antibacterial activities, and 7-[
R-2-amino-2-(3-chloro-4-hydroxyphenyl)acetamido]-3-methylthio-3-cephem-4-carboxylic acid was found to be a new orally active antibiotic.
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DAVID E. CANE, BERNARD J. RAWLINGS, CHI-CHING YANG
1987 Volume 40 Issue 9 Pages
1331-1334
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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LOTHAR W. BIEBER, ÁLVARO A. DA SILVA FILHO, JOSÉ F. DE M ...
1987 Volume 40 Issue 9 Pages
1335-1338
Published: September 25, 1987
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GIULIANO GRANDOLINI, CARLO G. CASINOVI, LAJOS RADICS
1987 Volume 40 Issue 9 Pages
1339-1340
Published: September 25, 1987
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HORACIO A. PRIESTAP
1987 Volume 40 Issue 9 Pages
1341-1343
Published: September 25, 1987
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J. ARONOVITCH, D. GODINGER, S. GOLDSTEIN, G. CZAPSKI
1987 Volume 40 Issue 9 Pages
1344-1348
Published: September 25, 1987
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YOICHI HAYAKAWA, KAZUYOSHI ADACHI, NOBUYASU KOMESHIMA
1987 Volume 40 Issue 9 Pages
1349-1352
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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KEN-ICHI KIMURA, SHOJI NAKAYAMA, TADAYOSHI KOYAMA, SHIN-ICHI SHIMADA, ...
1987 Volume 40 Issue 9 Pages
1353-1355
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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SATOSHI OMURA, HIROSHI TOMODA, HIDETOSHI KUMAGAI, MICHAEL D. GREENSPAN ...
1987 Volume 40 Issue 9 Pages
1356-1357
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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TOMIO TAKEUCHI, TSUTOMU SAWA, HIROSHI NAGANAWA, MASA HAMADA, HAMAO UME ...
1987 Volume 40 Issue 9 Pages
1358-1360
Published: September 25, 1987
Released on J-STAGE: April 19, 2006
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