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IV. HATOMARUBIGINS A, B, C AND D, NEW ISOTETRACENONE ANTIBIOTICS EFFECTIVE AGAINST MULTIDRUG-RESISTANT TUMOR CELLS
YOICHI HAYAKAWA, SANG-CHUL HA, YOON JEONG KIM, KAZUO FURIHATA, HARUO S ...
1991 Volume 44 Issue 11 Pages
1179-1186
Published: November 25, 1991
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A complex of new isotetracenone group antibiotics was isolated from the cultured broth of
Streptomyces sp. 2238-SVT4. It consisted of four related compounds, designated hatomarubigins A, B, C and D, whose structures were elucidated by NMR spectral analysis including a variety of 2D techniques. They enhanced the cytotoxicity of colchicine against multidrug-resistant tumor cells.
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KATSUSHIGE IKAI, KAZURO SHIOMI, KAZUTOH TAKESAKO, SHIGETOSHI MIZUTANI, ...
1991 Volume 44 Issue 11 Pages
1187-1198
Published: November 25, 1991
Released on J-STAGE: April 19, 2006
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Structures of 17 minor forms of aureobasidins (Abs), Abs B-R, were elucidated by mass fragmentation and amino acid analysis. The fragmentation patterns by FAB-MS spectroscopy of Abs A-E seemed to follow predictable rules, so we used the rules to elucidate the 13 other Abs. All Abs consisted of eight amino acids and one hydroxy acid.
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KATSUSHIGE IKAI, KAZURO SHIOMI, KAZUTOH TAKESAKO, IKUNOSHIN KATO, HIRO ...
1991 Volume 44 Issue 11 Pages
1199-1207
Published: November 25, 1991
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The
1H and
13C NMR spectra of aureobasidins A and E were analyzed by a variety of 2D NMR techniques. Two isomers of aureobasidin A existed as an equilibrium mixture in deuteriochloroform. The isomerism was associated with
cis-trans rotation of the amide bond between
N-methylphenylalanine and proline. Almost all of the aureobasidin E was found in deuteriochloroform as one conformer; the amide bond between β-hydroxy-
N-methylphenylalanine and proline was in the
cis-conformation. Experiments with the NOE made identification of the conformation of the amide bonds of aureobasidins A and E possible.
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FULL 1H AND 13C ASSIGNMENT, MOTIONAL BEHAVIOR, DIMERIZATION AND COMPLEXATION WITH AC-D-ALA-D-ALA
GYULA BATTA, FERENC SZTARICSKAI, KATALIN E. KÖVÉR, CHRISTI ...
1991 Volume 44 Issue 11 Pages
1208-1221
Published: November 25, 1991
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Complete
1H and
13C NMR assignments are presented for eremomycin (
1) and some of its desglycosylated derivatives
2,
3 and compared to the structurally closely related glycopeptide vancomycin. Primary structure and stereochemistry of eremomycin is corroborated by the present high field total correlation spectroscopy, NOESY and heteronuclear multiple-bond correlation NMR methods. A rough motional characterization of the title compound is attempted by
13C-T
1 and
13C-{
1H} NOE measurements. Dimerization of eremomycin is observed both in DMSO-
d6-CCl
4 and D
2O solutions. Complexation with cell wall analogue dipeptide Ac-D-Ala-D-Ala is also demonstrated.
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RYO MURAMATSU, SHIN-ICHIRO ABE, HIDEYA HAYASHI, KENJI YAMAGUCHI, KEIKO ...
1991 Volume 44 Issue 11 Pages
1222-1227
Published: November 25, 1991
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The primary structuture of phenomycin, an antitumor polypeptide antibiotic isolated from the culture broth of
Streptomyces fervens var.
phenomyceticus, was determined. Sequence analysis has revealed that it consists of 89 amino acid residues (M
r 9, 524) and no disulfide bridge is present. The sequence of phenomycin at residues 48-70 was found to be hydrophilic, being surrounded by hydrophobic regions at both sides. Furthermore, clustering of half the lysine residues in this hydrophilic region and marked basicity of phenomycin imply the external disposition of this region. Phenomycin does not show significant sequence homology to any known proteins including antitumor polypeptide antibiotics.
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SHINICHI KONDO, SHUICHI GOMI, DAISHIRO IKEDA, MASA HAMADA, TOMIO TAKEU ...
1991 Volume 44 Issue 11 Pages
1228-1236
Published: November 25, 1991
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In vitro activities of benanomicins and their analogues against human immunodeficiency virus and fungi including
Candida,
Cryptococcus and
Aspergillus, were examined. The free carboxyl group and at least one sugar moiety in the benanomicins were essential for their activities. Benanomicin A was most active and had low toxicity, and was selected as the best candidate for chemotherapy.
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KIYOHIRO NISHIKAWA, CHIEKO SHIBASAKI, TOMOKO UCHIDA, KATSUTOSHI TAKAHA ...
1991 Volume 44 Issue 11 Pages
1237-1246
Published: November 25, 1991
Released on J-STAGE: April 19, 2006
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The mode of
in vivo cell-killing by 15-deoxyspergualin (NKT-01) was assessed by measuring change of whole body radioactivity of mice inoculated with
125I-iododeoxyuridine-labeled P388 leukemia cells. Although NKT-01 showed strong life prolonging effect on P388 leukemia-bearing mice, significant excretion of
125I was not observed within 4 days after the start of treatment with NKT-01. Thereafter, the remaining
125I was reduced gradually and reached about half of control level on day 7. Colony forming ability in soft agar media of peritoneal tumor cells taken after completion of 5-day treatment with NKT-01 was markedly reduced to less than 3%. These results suggested that life prolongation of NKT-01 was produced both by a cytostatic effect, which lasts for an extraordinarily long period, and by a subsequent cytotoxic effect. Cell cycle distribution analysis using flow cytometry showed the cytostatic action of NKT-01 caused G
0/G
1 arrest of the tumor cells. Therefore, the drug-sensitive cycling population of the tumor cells was reduced, and combination with other antitumor agents was antagonistic, if they were administered simultaneously or consecutively with NKT-01. In contrast, if the other drugs such as cyclophosphamide, cisplatin and cytosine arabinoside, were administered prior to NKT-01, a synergistic combination effect was obtained. This synergism might be due to prolongation of the period of cell cycle perturbation caused by other drugs (such as G
2 arrest by cisplatin) by the cytostatic effect of NKT-01. Although the precise mechanisms of the cytostatic action of NKT-01 remain unclear, it might play an important role in the combination with other antitumor drugs.
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CEDRIC J. PEARCE, GUY T. CARTER, JEANNE A. NIETSCHE, DONALD B. BORDERS ...
1991 Volume 44 Issue 11 Pages
1247-1251
Published: November 25, 1991
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When the citreamicin-producing organism
Micromonospora citrea NRRL 189351 was incubated in the presence of the methylation inhibitors sinefungin or aminopterin, biosynthesis of the ζ component was stimulated approximately 20 to 200-fold above the level normally produced. Inhibition of a second methylation reaction, which is superficially very similar to the first, was not detected. Other known methylation inhibitors failed to yield any change in the natural pattern of citreamicins produced. This approach is an excellent route for preparing citreamicin ζ, which can be used as a substrate for semi-synthesis or for further biosynthetic studies.
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H. MARTÍNEZ-BLANCO, A. REGLERO, J. M. LUENGO
1991 Volume 44 Issue 11 Pages
1252-1258
Published: November 25, 1991
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Forty-seven different penicillins, including some of great clinical importance, have been synthesized "
in vitro" by coupling the newly described enzyme phenylacetyl-CoA ligase (PCL) from
Pseudomonas putida and acyl-CoA: 6-aminopenicillanic acid (6-APA) acyltransferase (AT) from
Penicillium chrysogenum. Incubations were carried out at 30°C in 50 mM HCl-Tris buffer pH 8.0. The reaction mixtures contained 6-APA, CoA, ATP, dithiothreitol, Mg
2+ and the corresponding penicillin side-chain precursor. This is the first description of the enzymatic synthesis of all the natural penicillins known, many of the semisynthetic until now reported, and some penicillins that could only be currently obtained by chemical synthesis. The efficiency of this prokaryotic-eukaryotic enzymatic-coupled system and its application to the synthesis of different β-lactam antibiotics are discussed.
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JUN'ICHI KOBAYASHI, MASASHI TSUDA, MASAMI ISHIBASHI, HIDEYUKI SHIGEMOR ...
1991 Volume 44 Issue 11 Pages
1259-1261
Published: November 25, 1991
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J. P. DIRLAM, W. P. CULLEN, L. H. HUANG, T. H. NELSON, J. R. OSCARSON, ...
1991 Volume 44 Issue 11 Pages
1262-1266
Published: November 25, 1991
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MARGARET A. MCHENNEY, RICHARD H. BALTZ
1991 Volume 44 Issue 11 Pages
1267-1269
Published: November 25, 1991
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XII. ISOLATION AND STRUCTURAL ELUCIDATION OF MYCINAMICINS X AND XI
KENJI KINOSHITA, SATOSHI TAKENAKA, MITSUO HAYASHI
1991 Volume 44 Issue 11 Pages
1270-1273
Published: November 25, 1991
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MAKOTO UBUKATA, CHIEKO TANAKA, HIROYUKI OSADA, KIYOSHI ISONO
1991 Volume 44 Issue 11 Pages
1274-1276
Published: November 25, 1991
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JIANXIN YANG, SHAOXIA FAN, HONGSHENG PEI, BAOQUAN ZHU, WENSI XU, HIROS ...
1991 Volume 44 Issue 11 Pages
1277-1279
Published: November 25, 1991
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YOON JEONG KIM, KAZUO FURIHATA, AKIRA SHIMAZU, KEIKO FURIHATA, HARUO S ...
1991 Volume 44 Issue 11 Pages
1280-1282
Published: November 25, 1991
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HIROSHI NISHIOKA, TSUTOMU SAWA, KUNIO ISSHIKI, YOSHIKAZU TAKAHASHI, HI ...
1991 Volume 44 Issue 11 Pages
1283-1285
Published: November 25, 1991
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2. CONVERSION OF 2-HYDROXYPROPYL-PHOSPHONIC ACID TO FOSFOMYCIN BY BLOCKED MUTANTS OF Streptomyces wedmorensis
HARUO SETO, TOMOMI HIDAKA, TOMOHISA KUZUYAMA, SEUI SHIBAHARA, TAKAYUKI ...
1991 Volume 44 Issue 11 Pages
1286-1288
Published: November 25, 1991
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