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I. TAXONOMY, FERMENTATION, PURIFICATION AND BIOLOGICAL ACTIVITIES
SUSUMU FUSHIMI, SHIGERU NISHIKAWA, AKIRA SHIMAZU, HARUO SETO
1989 Volume 42 Issue 7 Pages
1019-1025
Published: July 25, 1989
Released on J-STAGE: April 19, 2006
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New antibiotics phoslactomycins A, B, C, D, E and F, which contain α, β-unsaturated δ-lactone, phosphate ester, conjugated diene and cyclohexane ring moieties, were isolated from the culture broth of a soil isolate actinomycete. Morphological, cultural and physiological studies revealed that the isolate is a strain of
Streptomyces nigrescens. Phoslactomycins were obtained by butanol extraction, gel filtration and reverse phase chromatography. The antibiotics show strong activity against various fungi, particularly phytopathogenic fungi (
Botrytis cinerea and
Alternaria kikuchiana).
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II. STRUCTURE ELUCIDATION OF PHOSLACTOMYCINS A TO F
SUSUMU FUSHIMI, KAZUO FURIHATA, HARUO SETO
1989 Volume 42 Issue 7 Pages
1026-1036
Published: July 25, 1989
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Phoslactomycins A to F are new antifungal antibiotics produced by
Streptomyces nigrescens SC-273. On the basis of physico-chemical properties and NMR studies, their structures have been determined as shown in Fig. 6. They are characterized by possessing α, β-unsaturated δ-lactone, phosphate ester, conjugated diene and cyclohexane ring moieties. The structural difference between them is ascribed to a substituent bound to the cyclohexane ring.
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SATOSHI OMURA, SHIGERU EDA, SHINJI FUNAYAMA, KANKI KOMIYAMA, YOKO TAKA ...
1989 Volume 42 Issue 7 Pages
1037-1042
Published: July 25, 1989
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A new antibiotic, phenazinomycin (C
27H
32N
2O, MW 400), was isolated from the cultural mycelium of
Streptomyces sp. WK-2057. This antibiotic possesses antibacterial activities against Gram-positive bacteria
in vitro, direct cytotoxic activities against HeLa S
3, P388 and P388 doxorubicin-resistant cells
in vitro and antitumor activities against experimental murine tumors
in vivo.
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HARUMITSU IMAI, SHIGEO FUJITA, KENICHI SUZUKI, MOTO MORIOKA, TATSUHIRO ...
1989 Volume 42 Issue 7 Pages
1043-1048
Published: July 25, 1989
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Hatomamicin, a new alkaloid antibiotic, was isolated from the culture filtrate of a strain of
Saccharopolyspora. The antibiotic was extracted with EtOAc and purified by silica gel column chromatography. The free alkaloid was obtained as pale yellowish prisms from CH
3CN solution. It exhibits antimicrobial activity against Gram-positive organisms. The apparent molecular formula of hatomamicin was determined to be C
22H
31NO
5. The structure has been established by a combination of spectroscopic and X-ray crystallographic studies.
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SATOSHI NAKANISHI, KATSUHIKO ANDO, ISAO KAWAMOTO, HIROSHI KASE
1989 Volume 42 Issue 7 Pages
1049-1055
Published: July 25, 1989
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New inhibitors of Ca
2+ and calmodulin-dependent cyclic-nucleotide phosphodiesterase, KS-501 and KS-502 were isolated from a fungus, Sporothrix sp. KAC-1985. Inhibitory concentration causing 50% inhibition (IC
50) values of KS-501 and KS-502 for bovine brain enzyme were 1.8 and 4.3μM, respectively. The compounds exhibited no or weak inhibition for calmodulin-independent cyclic-nucleotide phosphodiesterases and protein kinase C.
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XIV. ISOLATION OF COMPONENTS OF INTACT SPORAVIRIDIN
KEN-ICHI HARADA, IKUMI KIMURA, TAKAMI SAKAZAKI, HIDEAKI MURATA, MAKOTO ...
1989 Volume 42 Issue 7 Pages
1056-1062
Published: July 25, 1989
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Six components of sporaviridin (SVD) were successfully isolated by HPLC using methanol - 1M ammonium chloride as the mobile phase. Each component possesses expectedly antimicrobial activity. To ensure the structural relationship between the intact SVD and
N-acetylated sporaviridins (
N-Ac-SVD), they were converted to the corresponding of
N-acetates by acetylation in methanol, whose structures had already been determined as glycosides consisting of a 34-membered macrocyclic lactone, viridopentaoses, D-glucose and
N-acetylvancosamine.
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TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES, STRUCTURE AND BIOLOGICAL PROPERTIES
M. PATEL, V. HEGDE, A. HORAN, T. BARRETT, R. BISHOP, A. KING, J. MARQU ...
1989 Volume 42 Issue 7 Pages
1063-1069
Published: July 25, 1989
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The complex containing a new platelet aggregation inhibitor, Sell 38519, was recovered from the fermentation filtrate of
Thermomonospora sp. SCC 1793. A chemically defined medium was developed which favored the production of Sch 38519. The antibiotic was isolated from the fermentation filtrate by absorption on macroreticular resin and further purified by ion exchange chromatography and reverse phase HPLC. Sch 38519 is an isochromanequinone structurally related to medermycin, lactoquinomycin and granaticin. It inhibits thrombin-induced aggregation of human platelets with an IC
50 of 68μg/ml. Sch 38519 is also active against Gram-positive and Gram-negative bacteria.
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3. ISOLATION, PURIFICATION AND CHARACTERIZATION OF CALICHEAMICINS β1Br, γ1Br, α2I, α3I, β1I, γ1I AND δ1I
MAY D. LEE, JOANN K. MANNING, DAVID R. WILLIAMS, NYDIA A. KUCK, RAYMON ...
1989 Volume 42 Issue 7 Pages
1070-1087
Published: July 25, 1989
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Novel antitumor antibiotics, calicheamicins β
1Br, γ
1Br, α
2I, α
3I, β
1I, γ
1I and δ
1I were recovered from the fermentation broth of
Micromonospora echinospora ssp.
calichensis by solvent extraction, selective precipitation, normal phase, reversed phase and partition chromatography. The individual components were characterized by their UV, IR,
1H and
13C NMR spectral data.
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DOREEN M. ASHWORTH, DUNCAN S. HOLMES, JOHN A. ROBINSON, HIDEAKI OIKAWA ...
1989 Volume 42 Issue 7 Pages
1088-1099
Published: July 25, 1989
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Streptomyces cinnamonensis produces the polyether ionophore antibiotic monensin A. Following a single round of mutagenesis by UV light, a derivative of this strain has been isolated, which secretes a new metabolite identified as 26-deoxymonensin A (
3). The structural elucidation of the new metabolite followed from a spectroscopic analysis, and its identity was proven conclusively following a comparison to 26-deoxymonensin A (
3) obtained synthetically from monensin A. The preparation of labelled forms of
3 is described, together with incorporation experiments using the parent strain of
S. cinnamonensis. Only very low levels of incorporation of
3 into monensin A were observed.
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HIROSHI ONOUE, YUKITOSHI NARUKAWA
1989 Volume 42 Issue 7 Pages
1100-1113
Published: July 25, 1989
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Four possible racemic isomers of
N-acetyl-5-methylthienamycin derivatives were synthesized and their antibacterial activities are discussed in relation to their physico-chemical properties. 5-Methylcarbapenems having various C-2 side chains were also prepared.
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III. SYNTHESIS AND ANTITUMOR ACTIVITIES OF AMINO ACYL DERIVATIVES
KIYOSHI SHIBATA, SADAYOSHI SATSUMABAYASHI, HIROSHI SANOT, KANKI KOMIYA ...
1989 Volume 42 Issue 7 Pages
1114-1123
Published: July 25, 1989
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Amino acyl derivatives of hitachimycin have been synthesized and evaluated their activities including antibacterial, cytocidal against HeLa cells and
in vivo antitumor against sarcoma 180. 15-
O-(
tert-Butoxycarbonyl(BOC)-glycyl)hitachimycin (
2), 15-
O-(BOC-β-alanyl)hitachimycin (4), 15-
O-(BOC-(
O-tert-Bu)-glutamyl)hitachimycin (
6) and 15-
O-L-alanylhitachimycin (
11) showed comparable
in vivo antitumor activity with hitachimycin and the solubility of these compounds was improved.
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SHINTARO NISHIMURA, HIROSHI SASAKI, NOBUYOSHI YASUDA, YOSHIMI MATSUMOT ...
1989 Volume 42 Issue 7 Pages
1124-1132
Published: July 25, 1989
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A series of 7α-hydroxyethyl-1-oxacephems (
1) was synthesized. The main focus of this study was to investigate biological activity relationships between 1-oxacephems (
1) and the corresponding cephems (
2). Replacement of the sulfur atom of
2 by the oxygen atom caused an enhancement of antibacterial activity, although the antibacterial activity of 1 was not high enough. Additionally
1 showed β-lactamase inhibitory activity, especially against cephalosporinase. However, the potency was lower than that of
2.
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KEIICHI AJITO, DAISHIRO IKEDA, KEIKO KOMURO, CHISATO NOSAKA, NOBUKO WA ...
1989 Volume 42 Issue 7 Pages
1133-1144
Published: July 25, 1989
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The preparation and biological evaluation of
N-salicylidene derivatives of pirarubicin are described. Pirarubicin was treated with various kinds of aryl aldehydes. Most of compounds synthesized here were more active than pirarubicin
in vitro. Some of them showed significant prolongation of the survival period in experimental mice by oral administration. Interestingly, a derivative containing forphenicine exhibited the broadest dose-response range by intraperitoneal administration.
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SHUICHI GOMI, MASAJI SEZAKI
1989 Volume 42 Issue 7 Pages
1145-1150
Published: July 25, 1989
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The biosynthesis of benanomicins A and B, produced by actinomycete strain MH193-16F4, was investigated by feeding experiments with
14C- and
13C-labeled compounds followed by measurement of radioactivity and
13C NMR analysis. A 2D double quantum coherence NMR spectrum of benanomicin A derived from sodium [1, 2-
13C
2]acetate provided the location of intact acetate units, and confirmed the
13C assignments of benanomicins. The results indicate that the aglycone of benanomicins is derived from a dodecaketide, methionine and alanine.
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IV. BIOSYNTHETIC STUDIES OF URDAMYCINS A-D
JÜRGEN ROHR, JOHN M. BEALE, HEINZ G. FLOSS
1989 Volume 42 Issue 7 Pages
1151-1157
Published: July 25, 1989
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The biogenetic origin of the angucycline antibiotics urdamycins A-D was studied by feeding experiments with isotope labeled precursors and by NMR analysis. Feeding experiments with [1-
13C]acetate and [1, 2-
13C
2]acetate show that the chromophores of urdamycins A and B and the angucycline 4-ring skeleton of the urdamycins C and D chromophores are formed from a single decapolyketide chain. The chromophores of the urdamycins C and D contain additional structural elements which derived from the amino acids tyrosine and tryptophan, respectively. The latter was shown by feeding deuterium-labeled tyrosine and 13C-labeled tryptophan derivatives. Feeding of [1-
13C]glucose and of [
U-
13C
3]glycerol proved that the
C-glycosidic moiety and the three sugars (2 × L-rhodinose, 1 × D-olivose each) of the urdamycins arise from glucose. Experiments with
14C-labeled urdamycin A, obtained by biosynthesis from [14C]acetate, showed this compound to be a late precursor of the urdamycins C and D.
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PETER CONRADT, KURT E. J. DITTMAR, HEIKE SCHLIEPHACKE, WOLFRAM TROWITZ ...
1989 Volume 42 Issue 7 Pages
1158-1162
Published: February 20, 1989
Released on J-STAGE: April 19, 2006
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Myxothiazol, a potent inhibitor of the cytochrome bc
1 oxidoreductase, was shown by the use of flow cytometry to block reversibly the late G
1/S phase of the cell cycle of human lymphoblastic T-cell line Jurkat (clone 886) at concentrations of 0.5 μ/ml. These observations are compared to those of other drugs, such as antimycin. which effect the respiratory chain, and with O
2-deficiency.
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HIROSHI KURAMOCHI, KATSUTOSHI TAKAHASHI, TOMIO TAKEUCHI
1989 Volume 42 Issue 7 Pages
1163-1170
Published: July 25, 1989
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The uptake of [
3H]peplomycin-Cu(II) ([3H]PEP-Cu(II)) into various tumor cell lines was studied. The time course of [
3H]PEP-Cu(II) uptake into AH66, AH66F, Ehrlich and P388 cells was biphasic. The first phase of uptake was completed within 5 minutes. The second, slower phase, of uptake into AH66, AH66F and Ehrlich cells increased linearly with incubation time, but that into P388 cells reached a plateau level. In L1210 cells, only the first rapid uptake was observed. The lower uptake into P388 and L1210 cells during the second phase may be related to their insensitivity to PEP.
However, the uptake into AH66F cells was higher than that into AH66 cells, although AH66F cells were less sensitive to PEP than AH66 cells. Deamide PEP was detected in intact cells which had taken up [3H]PEP-Cu(II) during 4 hours. This confirmed that PEP-Cu(H) was transported into the cell, the copper removed and PEP metabolized to deamide PEP.
[
3H]PEP-Cu(II) uptake into AH66 and AH66F cells increased in proportion to the extracellular concentration of drug up to at least 200 μg/ml, suggesting that uptake was not mediated by a carrier system. Metabolic inhibitors such as NaN
3 and 2, 4-dinitrophenol enhanced [
3H]PEP-Cu(II) uptake, but did not influence efflux. Uptake was also enhanced by membrane modifiers such as dibucaine and chlorpromazine which increase the fluidity of lipid membranes. The results suggest that PEP-Cu(II) was taken up into tumor cells by passive diffusion, controlled by an energy-dependent cell membrane barrier.
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I. EFFECTS OF CERULENIN ON ACTIVE OXYGEN-GENERATION AND LIPID METABOLISM IN PHAGOCYTES
MUNEHIRO NAKATA, TOSHIO TOMITA, SHIRO KANEGASAKI
1989 Volume 42 Issue 7 Pages
1171-1177
Published: July 25, 1989
Released on J-STAGE: April 19, 2006
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The antibiotic cerulenin, a known inhibitor of fatty acid and sterol synthesis, inhibited bactericidal activity of mouse peritoneal macrophages and chemiluminescence (CL) response upon phagocytosis. The antibiotic also inhibited the CL response of human neutrophils upon exposure to various stimuli such as chemotactic pep tide
N-formylmethionylleucylphenylalanine (fMLP), calcium ionophore A23187 and Staphylococcal delta toxin. The loss of CL response of both types of cells was observed only after incubation of the cells with cerulenin for certain periods. The results of radioactive precursor incorporation suggest that lipid metabolism blocked by cerulenin affected in turn signal transduction across the cell membrane and inhibited CL production in these cells.
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II. INHIBITION BY CERULENIN OF INTRACELLULAR CALCIUM MOBILIZATION IN HUMAN NEUTROPHILS
MUNEHIRO NAKATA, TOSHIO TOMITA, TETSUTARO IIZUKA, SHIRO KANEGASAKI
1989 Volume 42 Issue 7 Pages
1178-1183
Published: January 12, 1989
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Generation of superoxide anion (O
2-) and mobilization of intracellular Ca
2+ in human neutrophils upon exposure to stimuli such as
N-formylmethionylleucylphenylalanine (fMLP) were inhibited by the antibiotic cerulenin, which inhibits fatty acid and cholesterol biosynthesis. The inhibition of O
2- generation and Ca
2+-mobilization required certain periods of incubation with cerulenin and both abilities of the cells were gradually lost following a similar time-course. In contrast, significant Ca
2+-influx from the medium was observed in cerulenin-treated cells as well as untreated cells. The results suggest that an event which coincides with the Ca
2+mobilization and not Ca
2+ per se is important for the induction of O
2- generation in the fMLP-stimulated cells and that this step is blocked in cerulenin-treated cells. Phorbol myristate acetate or synthetic l-oleoyl-2-acetylglycerol were able to bypass the block and induced O
2- generation in cerulenin-treated cells.
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JANICE H. JOHNSON, D. W. PHILLIPSON, ALICIA D. KAHLE
1989 Volume 42 Issue 7 Pages
1184-1185
Published: July 25, 1989
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HARUMITSU IMAI, KENICHI SUZUKI, SHIGENOBU KADOTA, MASARU IWANAMI, TAKE ...
1989 Volume 42 Issue 7 Pages
1186-1188
Published: July 25, 1989
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DENISE PARISOT, MICHEL DEVYS, MICHEL BARBIER
1989 Volume 42 Issue 7 Pages
1189-1190
Published: July 25, 1989
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HIROSHI OHASHI, YING-HUA ZHENG, TAKUYA NIHIRA, YASUHIRO YAMADA
1989 Volume 42 Issue 7 Pages
1191-1195
Published: July 25, 1989
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SHINSUKE IMAI, KAZUO FURIHATA, YOICHI HAYAKAWA, TADASHI NOGUCHI, HARUO ...
1989 Volume 42 Issue 7 Pages
1196-1198
Published: July 25, 1989
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DOLATRAI M. VYAS, DANIEL BENIGNI, WILLIAM C. ROSE, WILLIAM T. BRADNER, ...
1989 Volume 42 Issue 7 Pages
1199-1201
Published: July 25, 1989
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TSUTOMU OIKAWA, KENJI HIROTANI, MARIKO SHIMAMURA, HIROMI ASKING-FUSE, ...
1989 Volume 42 Issue 7 Pages
1202-1204
Published: February 14, 1989
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