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I. TAXONOMY, FERMENTATION AND ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
KAZUYUKI DOBASHI, NAOKO MATSUDA, MASA HAMADA, HIROSHI NAGANAWA, TOMOHI ...
1988 Volume 41 Issue 11 Pages
1525-1532
Published: November 25, 1988
Released on J-STAGE: April 19, 2006
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Two antifungal antibiotics octacosamicins A and B were isolated from the culture broth of a strain of actinomycetes, which was identified as a strain of
Amycolatopsis. These antibiotics were isolated by resin adsorption and purified by column chromatography and preparative HPLC. Both antibiotics were found to be new substances from their physicochemical properties. They showed broad antifungal spectra.
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II. THE STRUCTURE ELUCIDATION USING VARIOUS NMR SPECTROSCOPIC METHODS
KAZUYUKI DOBASHI, HIROSHI NAGANAWA, YOSHIKAZU TAKAHASHI, TOMOHISA TAKI ...
1988 Volume 41 Issue 11 Pages
1533-1541
Published: November 25, 1988
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The structures of octacosamicins A and B, two new antifungal antibiotics, were studied by spectrometries and chemical modifications. The 2D NMR techniques including 1Hdetected heteronuclear multiple bond correlation method were successfully applied to this study. These antibiotics have unique linear chain structure possessing
N-hydroxyguanidyl group at the terminal.
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ADRIAN GEIGER, WALTER KELLER-SCHIERLEIN, MATTHIAS BRANDL, HANS ZÄ ...
1988 Volume 41 Issue 11 Pages
1542-1551
Published: November 25, 1988
Released on J-STAGE: April 19, 2006
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From a strain of
Streptomyces antibioticus seven yellow phenazines were isolated. The antibacterially most active antibiotic was identified as (-)-saphenamycin, a second one with compound DC-86-Y (saphenic acid). Three compounds were new: Saphenic acid methyl ether, 6-acetylphenazine-1-carboxylic acid and an inseparable mixture of fatty acid esters of saphenic acid. Two simple phenazines were phenazine-1-carboxylic acid (tubermycin B) and unsubstituted phenazine, which was isolated for the first time from a microorganism.
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URS BAHNMÜLLER, WALTER KELLER-SCHIERLEIN, MATTHIAS BRANDL, HANS Z ...
1988 Volume 41 Issue 11 Pages
1552-1560
Published: November 25, 1988
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A synthesis of racemie saphenic acid is described. From this acid 9 ester derivatives of saphenamycin were prepared. Those with aromatic acid components showed high activity against many Gram-positive and some Gram-negative bacteria. Of the esters with aliphatic acid moieties only the acetate and, to a lesser extent, the butyrate showed considerable antibacterial activities, whereas esters with higher fatty acids showed strongly reduced, if any, activities against some test organisms. Similar results were obtained with ID50 values against the eucaryotic tumor cell line CCRF/CEM. The salicylate, which is structurally similar to saphenamycin, was most active.
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I. TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES
TOSHIYUKI KAMEYAMA, ATSUSHI TAKAHASHI, HIROSHI MATSUMOTO, SHOGO KURASA ...
1988 Volume 41 Issue 11 Pages
1561-1567
Published: November 25, 1988
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Thrazarine,
O-((3
R)-2-diazo-3-hydroxybutyryl)-L-serine, is a new antitumor antibiotic produced by
Streptomyces coerulescens MH802-fF5. Thrazarine was isolated from culture filtrate by Sephadex LH-20 column chromatography and reversed phase HPLC. Thrazarine induced cytolysis of tumor cell lines co-cultured with nonactivated macrophages. This effect was tumor specific because the nontumorigenic cells were not lysed by macrophages in the presence of thrazarine. Thrazarine inhibited DNA synthesis and growth of tumor cells directly. It showed neither antimicrobial activity nor the inhibition of transamidation reactions in contrast to azaserine. Toxicities of thrazarine were much weaker than those of azaserine.
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II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION
ATSUSHI TAKAHASHI, HIKARU NAKAMURA, DAISHIRO IKEDA, HIROSHI NAGANAWA, ...
1988 Volume 41 Issue 11 Pages
1568-1574
Published: November 25, 1988
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A new antitumor antibiotic thrazarine was soluble in water and positive to anisaldehydesulfuric acid and ninhydrin color reactions. The absolute structure of thrazarine was determined to be
O-((3
R)-2-diazo-3-hydroxybutyryl)-L-serine by acid hydrolysis, spectroscopic analysis and X-ray crystallographic analysis. Structurally, thrazarine was a new member of azaserine group antibiotics.
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I. DISCOVERY, TAXONOMY OF PRODUCING ORGANISM, FERMENTATION AND BIOLOGICAL ACTIVITY
JILAN HU, YU-CHUAN XUE, MEI-YU XIE, RUI ZHANG, TOSHIO OTANI, YOSHINORI ...
1988 Volume 41 Issue 11 Pages
1575-1579
Published: November 25, 1988
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Strain C-1027, an actinomycete isolated from a soil sample collected in China, was found to produce the new antibiotic, C-1027. From taxonomical studies on its morphological, cultural and physiological characteristics, this antibiotic-producing strain was identified as
Streptomyces ghbisporus C-1027. Antibiotic C-1027 has antimicrobial activity against most Gram-positive bacteria but not against
Mycobacterium sp. or Gram-negative bacteria. This antibiotic shows remarkable activity in spermatogonial assay and potent cytotoxicity against KB carcinoma cells in vitro, and exhibits inhibition on transplantable tumors in mice.
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II. ISOLATION AND PHYSICO-CHEMICAL PROPERTIES
TOSHIO OTANI, YOSHINORI MINAMI, TERUYOSHI MARUNAKA, Rui ZHANG, MEI-YU ...
1988 Volume 41 Issue 11 Pages
1580-1585
Published: November 25, 1988
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A new macromolecular antibiotic C-1027 was obtained from the broth filtrate of
Streptomyces ghbisporus C-1027 by precipitation with ammonium sulfate, DEAE-cellulose column chromatography and gel filtration chromatography on a Sephadex G-75 column. This antibiotic, prepared as a white powder, is an acidic polypeptide having an isoelectric point of pH 3.5-3.7 and a molecular weight of 15, 000 as determined by SDS-polyacrylamide gel electrophoresis and gel filtration chromatography. The acid hydrolysate of the purified antibiotic C-1027 contained no methionine or tryptophan. From the physico-chemical data, it may be considered to possess a very labile non-protein chromophore.
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I. TAXONOMY OF THE PRODUCING STRAIN
HIROSHI HATANAKA, MORITA IWAMI, TOHRU KINO, TOSHIO GOTO, MASAKUNI OKUH ...
1988 Volume 41 Issue 11 Pages
1586-1591
Published: November 25, 1988
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A new subspecies of the genus
Streptomyces, the proposed name of which is
Streptomyces hygroscopicus subsp.
yakushimaensis subsp. nov., is described. Soil isolate, strain No. 7238, produces the novel immunosuppressants, FR-900520 and FR-900523. The organism is characterized by its gray aerial mycelium color, hygroscopic spore mass and spiral spore chains with warty or spiny spore surfaces. It is nonchromogenic. Strain No. 7238 shows characteristics most closely related to
Streptomyces antimycoticus and
S. hygroscopicus, although there are differences in physiological characteristics and carbohydrate utilization. In terms of morphological characteristics, strain No. 7238 is different from
S. antimycoticus, but resembles
S. hygroscopicus. The differences are not sufficient to establish a new species. It would be most suitable to designate strain No. 7238 as a new subspecies within the species of
S. hygroscopicus.
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II. FERMENTATION, ISOLATION AND PHYSICO-CHEMICAL AND BIOLOGICAL CHARACTERISTICS
HIROSHI HATANAKA, TOHRU KINO, SUSUMU MIYATA, NORIAKI INAMURA, AKIO KUR ...
1988 Volume 41 Issue 11 Pages
1592-1601
Published: November 25, 1988
Released on J-STAGE: April 19, 2006
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FR-900520 and FR-900523, novel neutral macrolide immunosuppressants, were isolated from the cultured broth of
Streptomyces hygroscopicus subsp.
yakushimaensis No. 7238. Their molecular formulae were determined as C
43H
69NO
12 and C
42H
67NO
12, respectively. The compounds suppressed immune response
in vitro. IC
50 values of FR-900520 and FR900523 for mouse mixed lymphocyte reaction were 0.55 nM and 1.6nM, respectively. FR900520, the major component, clealy prolonged skin allograft survival in rats.
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HAJIME KAMACHI, YUKIO NARITA, TAKAAKI OKITA, YOSHIO ABE, SEIJI IIMURA, ...
1988 Volume 41 Issue 11 Pages
1602-1616
Published: November 25, 1988
Released on J-STAGE: April 19, 2006
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The synthesis and structure-activity relationships of 7-[(
Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(
Z)-1-propenyl]-3-cephem-4-carboxylic acid (BMY-28232), its 3-alkenyl analogs (
6 and
7) and
O-substituted derivatives of the oxyimino moiety (
10) are described, as well as the oral pharmacokinetics and
in vivo activities of the 1-acetoxyethyl ester of BMY-28232 (BMY-28271) and its analogous esters (
11). The 3-alkenyl groups were introduced by the Wittig reaction of the ylide (
2) prepared from the 3-chloromethyl cephem (1) to afford the
Z (main) and
E (minor) isomers regarding the 3-side chain. The
O-substituted derivatives (
10) were prepared by 7-
N-acylation of the 7-amino cephem (
4a) with the corresponding
O-substituted side chain acids (
8). The prodrug esters (
11) were prepared by esterification of BMY-28232 with an appropriate halide. BMY-28232 was the most active among the 3-alkenyl analogs tested against Gram-negative organisms and much more active than the
O-substituted derivatives against Gram-positive bacteria. BMY-28271 showed good oral bioavailability (66 %) and good
in vivo efficacy in mice against infections of
Staphylococcus aureus Smith (PD
50, 0.68 mg/kg) and
Escherichia coli Juhl (0.54 mg/kg).
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TAKEO YOSHIOKA, KOHKI KIYOSHIMA, MIHARU MAEDA, MICHIKO SAKAMOTO, TOMOY ...
1988 Volume 41 Issue 11 Pages
1617-1628
Published: November 25, 1988
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Eleven 4''-
O-acyltylosin derivatives were synthesized and subjected to a two-step screening system consisting of antimicrobial activity and esterase stability assays. The new derivatives were all active against macrolide-resistant Staphylococci and mycoplasmas, but only 4''-
O-methoxy)phenylacetyltylosin and 4''-
O-(4-acetyl)phenylacetyltylosin showed better resistance to mouse liver esterase than 4''-
O-phenylacetyl tylosin (reference compound C).
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RINZO NISHIZAWA, YUKIO TAKEI, MASAO YOSHIDA, TSUGIO TOMIYOSHI, TETSUSH ...
1988 Volume 41 Issue 11 Pages
1629-1643
Published: November 25, 1988
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Stable spergualin analogues were synthesized by substitutions of the α-hydroxyglycine residue of spergualin with various α- or ω-amino acids.
The antitumor activity of these analogues against L1210 and their immunosuppressive effects on delayed-type hypersensitivity and antibody formation was then examined. Analogues substituted with glycine and L-serine showed significant biological activity but were less potent than 15-deoxyspergualin.
Among the analogues synthesized so far, 10-[
N-4-(4-guanidinophenyl)butyryl-L-seryl]-1, 5, 10-triazadecane has possessed the strongest antitumor and immunosuppressive activities.
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ERIC HUNT, DAVID J. C. KNOWLES, CHRISTINE SHILLINGFORD, ISKANDER I. ZO ...
1988 Volume 41 Issue 11 Pages
1644-1648
Published: November 25, 1988
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Erythromycin A 11, 12-methylene acetal (
5) and the corresponding 9-methoxime, 9-dihydro, and 8-hydroxy derivatives have been prepared and their antibacterial activities compared with those of erythromycin A and its 11, 12-cyclic carbonate. The simple methylene acetal
5 showed excellent activity against Gram-positive organisms
in vitro.
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DARARAT RODPHAYA, TAKUYA NIHIRA, SHOHEI SAKUDA, YASUHIRO YAMADA
1988 Volume 41 Issue 11 Pages
1649-1658
Published: November 25, 1988
Released on J-STAGE: April 19, 2006
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Patulolides are 12-membered macrolides produced by
Penicillium urticae S11R59, and they are the simplest macrolide antibiotics. All carbon signals, including six methylene signals of patulolides A (
1), B (
2), and C (
3), were completely assigned by use of the
13C two-dimensional INADEQUATE. The biosynthesis of patulolides was investigated with
13C labeled acetate. Feeding of [l-
13C]acetate to a culture of P. urticae SI 1R59 gave patulolides A (
1), B (
2), and C (
3), each of which showed enrichment at carbons 1, 3, 5, 7, 9, and 11; enrichment at carbons 2, 4, 6, 8, 10, and 12 was observed upon feeding of [2-
13C]acetate. These results showed that patulolides A (
1), B (
2), and C (
3) are pure acetogenic hexaketides derived from six acetate units coupled in head-to-tail fashion.
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RICHARD A. NELSON, JOSEPH A. POPE, RAMESH C. PANDEY, LLOYD E. MCDANIEL ...
1988 Volume 41 Issue 11 Pages
1659-1667
Published: November 25, 1988
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The biosynthesis of crisamicin A, a novel dimeric isochromanequinone antibiotic from
Micromonospora purpureochromogenes subsp.
halotolerans has been investigated by [1-
13C] and [2-
13C] labeled acetate precursor feeding experiments. Analysis of the proton noise decoupled and off resonance
13C NMR spectra of
13C enriched and unenriched crisamicin A and their acetate derivatives indicated the biosynthesis
via the polyketide pathway, as expected. Further analysis of the enriched spectra allowed the complete assignment of the carbon signals. Of particular interest was the establishment of the linkage between the two monomeric halves of the molecule and determination of the location of the phenolic hydroxyls.
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TAKENORI ISHIMARU, TSUNEO KANAMARU, TOSHIYUKI TAKAHASHI, HISAYOSHI OKA ...
1988 Volume 41 Issue 11 Pages
1668-1674
Published: November 25, 1988
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Fibrostatin C, a novel prolyl hydroxylase inhibitor produced by
Streptomyces catenulae subsp.
griseospora No. 23924, inhibited the activity of purified chick embryo prolyl hydroxylase by about 50% at a concentration of 2.9×10
-5 M. The inhibition was mixed type with respect to (Pro-Pro-Gly)
5 with a Ki of 2.1×10
-5 M. When an excess of ferrous ions or ascorbate was added to the reaction mixture, the inhibition was negligibly or slightly reversed, respectively.
Fibrostatin C, when administered intraperitoneally at 1 mg/kg/day or orally at about 100mg/kg/day as a dietary admixture, significantly inhibited estradiol-17β stimulated collagen biosynthesis in the uterus of the immature rat.
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YOSHIE YOSHIKAWA, HIROYUKI UCHIDA, HIROYUKI KURODA, TERUYA NAKAMURA, A ...
1988 Volume 41 Issue 11 Pages
1675-1680
Published: November 25, 1988
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We studied the effects of deoxyspergualin (NKT-01) on the events of lymphocyte activation in vivo by inoculating mice in the footpad with allogeneic spleen cells, and compared the effects with those of cyclosporin A (CyA). The administration of NKT-01 increased the numbers of cells recovered from the popliteal lymph node (PLN) 7 days after inoculation, but inhibited the proliferation of these cells in the presence of exogenous interleukin 2 (IL-2). NKT-01 enhanced IL-2 production, but suppressed the production of macrophage activating factor (MAF) in the mixed lymphocyte reaction between the PLN cells and allogeneic spleen cells treated with mitomycin C. CyA decreased the numbers of PLN cells little, and suppressed the response to exogenous IL-2 and the production of both IL-2 and MAP. Results with tumor cells used as allogeneic cells suggested that there was a close relationship between the suppression of MAP production by NKT-01 and its inhibition of allograft rejection. The findings showed that NKT-01 inhibited both the MAP production by and the response to IL-2 of PLN cells, and that these effects were involved in the suppression of allograft rejection by NKT-01.
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H. ANKE, I. CASSER, M. SCHRAGE, W. STEGLICH
1988 Volume 41 Issue 11 Pages
1681-1684
Published: November 25, 1988
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I. SYNTHESIS AND IN VITRO ACTIVITY OF NOVEL 2-CHIRAL SUBSTITUTED PENEMS
MASAJI ISHIGURO, HIROMITSU IWATA, TAKASHI NAKATSUKA, RIE TANAKA, YOKO ...
1988 Volume 41 Issue 11 Pages
1685-1693
Published: November 25, 1988
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JACK E. BALDWIN, ROBERT M. ADLINGTON, NICHOLAS P. CROUCH, JANICE B. CO ...
1988 Volume 41 Issue 11 Pages
1694-1695
Published: November 25, 1988
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TOSHIO OTANI, YOSHINORI MINAMI, TERUYOSHI MARUNAKA, RUI ZHANG, MEI-YU ...
1988 Volume 41 Issue 11 Pages
1696-1698
Published: November 25, 1988
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CHANTAL LATOUD, FRANQOISE PEYPOUX, GEORGES MICHEL
1988 Volume 41 Issue 11 Pages
1699-1700
Published: November 25, 1988
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TOSHIKAZU OKI, MASATAKA KONISHI, Kozo TOMATSU, KOJI TOMITA, KYO-ICHIRO ...
1988 Volume 41 Issue 11 Pages
1701-1704
Published: November 25, 1988
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JOSEPH O'SULLIVAN, CAROL A. AKLONIS, WEN-CHIH LIU
1988 Volume 41 Issue 11 Pages
1705-1707
Published: November 25, 1988
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AKIKO TANABE, HIDEKI NAKASHIMA, OSAMU YOSHIDA, NAOKI YAMAMOTO, OSAMU T ...
1988 Volume 41 Issue 11 Pages
1708-1710
Published: November 25, 1988
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