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1. PRODUCTION, ISOLATION AND CHARACTERIZATION
TERUAKI OZASA, KENICHI SUZUKI, MIHO SASAMATA, KOUICHI TANAKA, MASATO K ...
1989 Volume 42 Issue 9 Pages
1331-1338
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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Phospholine was isolated as an antitumor antibiotic from the fermentation broth of
Streptomyces hygroscopiciis. Phospholine is an amphoteric compound which has an amino group and a phosphoric acid ester as functional groups. Phospholine shows strong activities against L1210, P388 and EL-4.
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2. STRUCTURE DETERMINATION
TERUAKI OZASA, KOUICHI TANAKA, MIHO SASAMATA, HIDETOSHI KANIWA, MINORU ...
1989 Volume 42 Issue 9 Pages
1339-1343
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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Phospholine, an antitumor antibiotic, has the molecular formula of C
25H
40NO
8P and posesses a δ-lactone and a phospholic acid ester as functional groups. Its structure was determined based on interpretation of fast atom bombardment MS,
1H NMR,
13C NMR,
1H-
1H correlation spectroscopy (COSY),
13C-
1H COSY, heteronuclear multiple bond correlation spectroscopy, elemental analysis and chemical modifications.
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KANKI KOMIYAMA, SHINJI FUNAYAMA, YUMI ANRAKU, AKIRA MITA, YOKO TAKAHAS ...
1989 Volume 42 Issue 9 Pages
1344-1349
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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Three antioxidant isoflavonoids characterized as 4', 7, 8-trihydroxyisoflavone (
1), 3', 4', 7-trihydroxyisoflavone (
2) and 8-chloro-3'4', 5, 7-tetrahydroxyisoflavone (
3) were isolated from the cultured broth of
Streptomyces sp. OH-1049. Among them, 3 is a novel isoflavonoid possessing a chlorine atom in the molecule.
In
in vitro studies, these antibiotics were found to possess antioxidant activity whereas showed almost no cytocidal activities against HeLa S
3 cells.
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SHINJI FUNAYAMA, YUMI ANRAKU, AKIRA MITA, KANKI KOMIYAMA, SATOSHI OMUR ...
1989 Volume 42 Issue 9 Pages
1350-1355
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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Structures of three antioxidant isoflavonoids isolated from the cultured broth of
Streptomyces sp. OH-1049 were shown to be 4', 7, 8-trihydroxyisoflavone (
1), 3', 4', 7-trihydroxyisoflavone (
2) and 8-chloro-3', 4', 5, 7-tetrahydroxyisoflavone (
3), respectively. Among them, 3 is a novel isoflavonoid possessing a chlorine atom in the molecule.
Compound
1 was synthesized and its antitumor activities were tested against IMC carcinoma, SI80, P388 leukemia and P388/ADM leukemia
in vivo. As a result,
1 showed 139% increase in life span (ILS) against SI80 bearing mice whereas it showed slight or no ILS against IMC carcinoma, P388 leukemia and P388/ADM leukemia bearing mice.
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TOSHIHIRO SHIBATA, MOTOAKI NISHIKAWA, YASUHISA TSURUMI, SHIGEHIRO TAKA ...
1989 Volume 42 Issue 9 Pages
1356-1361
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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FR-901235 is a new type of immunoactive substance produced by an imperfect fungus,
Paecilomyces carneus F-4882.
The mitogen-induced lymphocyte proliferation which had been suppressed by addition of immunosuppressive factor, was restored to a normal level by the addition of FR-901235. Furthermore, the subsequent administration of FR-901235 partially restored the impaired delayed-type hypersensitivity to sheep red blood cells in tumor-bearing mice.
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SATOSHI YAGINUMA, AKIRA ASAHI, ATSUKI MORISHITA, MITSUO HAYASHI, MASAT ...
1989 Volume 42 Issue 9 Pages
1362-1369
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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New thiol protease inhibitors, estatins A and B, were isolated from the culture filtrate of
Myceliophthora thermophila M4323. The basic, water-soluble inhibitors were characterized as having an agmatine,
tuans-epoxysuccinic acid and L-phenylalanine or L-tyrosine moieties in the structure. The molecular formulas C
18H
25N
5O
5 and C
18H
25N
5O
6 for A and B were indicated by elemental analysis and fast atom bombardment MS. Estatins were specific inhibitors against thiol proteases such as papain, ficin and bromelain. They suppressed IgE antibody production in mice, but not IgG.
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SUSUMU FUSHIMI, SHIGERU NISHIKAWA, NOBUAKI MITO, MASAHIKO IKEMOTO, MIT ...
1989 Volume 42 Issue 9 Pages
1370-1378
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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Homoalanosine having a herbicidal activity was isolated from the culture filtrate of a soil isolate SC-1688 which was classified as
Streptomyces galilaeus. The chemical structure of homoalanosine was determined to be L-2-amino-4-nitrosohydroxyaminobutyric acid by analyses of spectral and biological data. The antibiotic has high herbicidal activity at low concentrations against especially common cocklebur and ladysthumb among the tested weeds and crops. Foliar application of this antibiotic inhibited the growth of roots and buds. This result indicated that homoalanosine had a systemic herbicidal activity.
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YASUTSUGU UEDA, JULIA M. CHUANG, LEONARD B. CRAST, R. A. PARTYKA
1989 Volume 42 Issue 9 Pages
1379-1392
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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Several new semi-synthetic coumermycin analogs, which carry a polar substituent at the C-3 amide moiety have been prepared.
In vitro antibacterial activity of these new analogs against Gram-positive organisms, particularly methicillin-resistant strains of Staphylococci species has been described.
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VALENTINE ROCHEROLLE, ALAIN OLESKER, GABOR LUKACS
1989 Volume 42 Issue 9 Pages
1393-1397
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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The title new daunorubicin analogues have been prepared from methyl 4, 6-
O-benzylidene-2-
C-methyl-α-D-
ribo-hexopyranosid-3-ulose and daunomycinone. The antitumor activity of these compounds was very similar to that of daunorubicin.
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JOSÉ M. FERNÁNDEZ-CAÑÓN, ANGEL REGLERO, HO ...
1989 Volume 42 Issue 9 Pages
1398-1409
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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The transport system of phenylacetic acid (PA) in
Penicillium chrysogenum was studied. Kinetic measurements were carried out "
in vivo" at 25°C in 0.06 M phosphate buffer at pH 6.5. Uptake was a linear function of time over 3 minutes and the
Km was 5.2μM. PA uptake was inhibited by 2, 4-dinitrophenol, 4-nitrophenol, sodium azide, potassium cyanide,
N-ethylmaleimide, amino acids, xylose and fatty acids whereas lactose and ribose stimulated it. Benzylpenicillin, phenoxymethylpenicillin, penicillins DF, K and 6-aminopenicillamc acid did not modify uptake whereas phenoxyacetic acid and many phenyl derivatives strongly inhibited the incorporation of PA.
PA transport is an inducible system that is strictly regulated by the carbon source used for
P. chrysogenum growth. Uptake is not induced by phenoxyacetic acid and is repressed by L-lysine.
The absence of the PA transport system when
P. chrysogenum is grown in the presence of readily metabolized sugars and its repression by L-lysine suggests that this is a critical regulatory point in the control of benzylpenicillin biosynthesis.
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JOSÉ M. FERNÁNDEZ-CAÑÓN, ANGEL REGLERO, HO ...
1989 Volume 42 Issue 9 Pages
1410-1415
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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The phenylacetic acid (PA) transport system of
Penicillium chrysogenum is induced by PA, 2-hydroxyphenylacetic and 4-phenylbutyric acids but not by benzoic, phenoxyacetic acid and phenylpropionic acids. Substitution in the aromatic moiety (3-hydroxyphenylacetic, 4-hydroxyphenylacetic acids), replacement of the aromatic moiety by other rings (thiophene2-acetic acid, indole-3-acetic or indole-3-butyric acids) or the presence of an amino group in the α-position (2-aminophenylacetic acid) eliminates inducing activity. 2-Phenylbutyric acid dose not induce the PA transport system indicating that fatty acid-β-oxidation is needed to generate the authentic regulatory molecule (phenylacetyl-CoA) from 4-phenylbutyric acid. Furthermore, the uptake system synthesized in presence of PA, 2-hydroxyphenylacetic or 4-phenylbutyric acids is under carbon catabolic repression control and is also repressed by L-lysine suggesting that the three molecules induce in
P. chrysogenum a single mechanism of transport.
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HONORINA MARTÍNEZ-BLANCO, ANGEL REGLERO, MIGUEL A. FERRERO, J. ...
1989 Volume 42 Issue 9 Pages
1416-1423
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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The phenylacetic acid (PA) transport system in
Penicillium chrysogenum is an induciblesystem (see FERNÁNDEZ-CAÑÓN
et al.; preceding papers) which is repressed by free amino acids when these molecules are added to the complex fermentation broths at the induction time. L-Tyrosine, L-α-aminoadipic acid, L-tryptophan, L-phenylalanine and L-methionine are the molecules that cause the greatest delay in induction. The addition of Krebs-cycle intermediates to the complex fermentation broth did not affect the rate of induction with the exception of oxalacetic acid and citric acid which strongly increased it. Ammonium salts and acetate also repressed the biosynthesis of the enzymes involved in the PA uptake.
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NOBUYASU KOMESHIMA, HLROYUKI KAWAI, SHOHACHI NAKAJIMA, MASAHIKO WATANA ...
1989 Volume 42 Issue 9 Pages
1424-1429
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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3'-Deamino-3'-morpholino-lS-deoxo-lO-hydroxycarminomycin (MX2), a morpholino anthracycline derived from 13-deoxo-lO-hydroxycarminomycin (R20X2) was 16 times less cytotoxic than R20X2 against cultured P388 leukemia cells. The reduced cytotoxicity of MX2 was not explainable by intracellular or intranuclear concentration of the drug or by its DNA-intercalating activity. Binding of MX2 and R20X2 to DNA was measured, after isolating the DNA fraction from an incubation mixture of the drugs with P388 cells or with calf thymus DNA. The amount of R20X2 bound to the DNA was obviously larger than that of MX2, and was dependent on incubation time. These data suggest that the poor binding activity of MX2 to DNA contributes to its reduced cytotoxicity.
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JACQUES BERNILLON, JEAN FAVRE-BONVIN, MARIE-THÉRÈSE POMM ...
1989 Volume 42 Issue 9 Pages
1430-1432
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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TAKASHI ADACHI, JOJI SASAKI, SADAFUMI OMURA
1989 Volume 42 Issue 9 Pages
1433-1437
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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RAMAKRISHNAN NAGARAJAN, DONNIS M. BERRY, AMELIA A. SCHABEL
1989 Volume 42 Issue 9 Pages
1438-1440
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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M. B. KOBRIN, H. S. KATRUKHA, G. B. FEDOROVA
1989 Volume 42 Issue 9 Pages
1441-1442
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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CATHERINE RUGGERI, MARIA DE LOS A. LABORDE, AIMÉE DESSINGES, LI ...
1989 Volume 42 Issue 9 Pages
1443-1445
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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JAMES A. MATSON, WILLIAM C. ROSE, JAMES A. BUSH, ROBERT MYLLYMAKI, WIL ...
1989 Volume 42 Issue 9 Pages
1446-1448
Published: September 25, 1989
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MASATAKA KONISHI, HIROAKI OHKUMA, KIYOSHI MATSUMOTO, TAKASHI TSUNO, HI ...
1989 Volume 42 Issue 9 Pages
1449-1452
Published: September 25, 1989
Released on J-STAGE: April 19, 2006
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