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I. DISCOVERY, TAXONOMY, ISOLATION, AND PROPERTIES
YOSHIO KURODA, MASAKUNI OKUHARA, TOSHIO GOTO, EIKO IGUCHI, MASANOBU KO ...
1980 Volume 33 Issue 2 Pages
125-131
Published: 1980
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A new antibiotic, designated FR-900130, has been discovered in the culture filtrate of
Streptomyces. The producing organism has been identified as
Streptomyces catenulae. The antibiotic was purified by adsorption onto Duolite C-20, passage through Amberlite IRC-50, final purification and desalting on Sephadex G-25. It shows antimicrobial activity against Gram-positive bacteria and synergy with D-cycloserine. The antibiotic is very labile in alkaline solution above pH 8.0 and decomposed during lyophilization or solvent precipitation. It was converted to an acetyl derivative and the biological properties of the derivative were examined.
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II. ISOLATION AND STRUCTURE ELUCIDATION OF THE ACETYL DERIVATIVE OF FR-900130
YOSHIO KURODA, MASAKUNI OKUHARA, TOSHIO GOTO, MASANOBU KOHSAKA, HATSUO ...
1980 Volume 33 Issue 2 Pages
132-136
Published: 1980
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FR-900130 is a new antibiotic having an acetylene moiety and is very unstable in aqueous solution. The antibiotic was isolated as the acetyl derivative by ion-exchange resin and adsorption chromatography. The structure has been determined to be L-2-amino-3-butynoic acid by spectral data of its derivatives.
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LEUSERAMYCIN, A NEW POLYETHER ANTIBIOTIC PRODUCED BY STREPTOMYCES HYGROSCOPICUS
TAKU MIZUTANI, MICHIO YAMAGISHI, HIROSHI HARA, AKIRA KAWASHIMA, SADAFU ...
1980 Volume 33 Issue 2 Pages
137-143
Published: 1980
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A new antibiotic leuseramycin has been isolated from the cultured mycelium of the strain of
Streptomyces hygroscopicus TM-531. Physicochemical data, in particular those of
1H- and
13C-NMR spectra, revealed that leuseramycin is closely related to dianemycin in its structure, the former having a methyl group in place of the hydroxymethyl group at C-30. It is active against Gram-positive bacteria, some phytopathogenic fungi and some protozoa.
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THE ASSIGNMENTS OF THE 13C-NMR SPECTRA OF DIANEMYCIN AND LENOREMYCIN
KAZUTOSHI MIZOUE, HARUO SETO, TAKU MIZUTANI, MICHIO YAMAGISHI, AKIRA K ...
1980 Volume 33 Issue 2 Pages
144-156
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All the resonances observed in the
13C-NMR spectra of polyether antibiotics, dianemycin and lenoremycin (Ro 21-6150) have been assigned by the aid of selective proton decoupling experiments, T
1, value measurements and biosynthetic methods as well as comparison to model compounds such as monensin, nigericin, etheromycin and carriomycin.
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I. PRODUCTION, ISOLATION AND PROPERTIES OF Bu-2313 A AND B
I. PRODUCTION, HIROSHI TSUKIURA, KOJI TOMITA, MINORU HANADA, SEIKICHI ...
1980 Volume 33 Issue 2 Pages
157-165
Published: 1980
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An unidentified oligosporic actinomycete strain, No. E864-61, produced two new antibiotics, Bu-2313 A (C
27H
35NO
9) and Bu-2313 B (C
26H
33NO
9). Bu-2313 A and B each exhibited a broad antibiotic spectrum against Gram-positive and Gram-negative anaerobic bacteria, and showed
in vivo activity against experimental infections produced by
B. fragilis and
C. perfringens. Bu-2313 also inhibited some aerobic bacteria such as streptococci. Bu-2313 B was approximately two-fold more active than Bu-2313 A.
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II. STRUCTURE DETERMINATION OF Bu-2313 A AND B
MITSUAKI TSUNAKAWA, SOICHIRO TODA, TAKA-AKI OKITA, MINORU HANADA, SUSU ...
1980 Volume 33 Issue 2 Pages
166-172
Published: 1980
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The structures of Bu-2313 A and B have been determined. They are dienoyltetramic acid-containing antibiotics structurally related to streptolydigin and tirandamycin.
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III. SEMI-SYNTHESIS OF Bu-2313 A AND B, AND THEIR ANALOGS
SOICHIRO TODA, SUSUMU NAKAGAWA, TAKAYUKI NAITO, HIROSHI KAWAGUCHI
1980 Volume 33 Issue 2 Pages
173-181
Published: 1980
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Analogs of Bu-2313 A and B were prepared by C-acylation of tetramic acid derivatives with the dienoic acid moiety obtained by periodate oxidation of Bu-2313 A or B. The C-acylation proceeded in the presence of a strong base such as potassium
t-butoxide, sodium hydride or lithium hydride, whereas the use of triethylamine afforded O-acylated products. The semi-synthetic Bu-2313 analogs exhibited antibacterial spectra similar to the parent antibiotic but none exceeded Bu-2313 B in activity.
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STUDIES ON ANTIBIOTICS FROM THE GENUS BACILLUS. XXVII)
JUN'ICHI SHOJI, RYUZI SAKAZAKI, YOSHIHARU WAKISAKA, KENZO KOIZUMI, SHI ...
1980 Volume 33 Issue 2 Pages
182-185
Published: 1980
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A new peptide antibiotic complex, named octapeptin D, was isolated from culture broth of a microorganism belonging to the genus
Bacillus. The trihydrochloride of the antibiotic was obtained as a colorless powder, soluble in water and methanol. The empirical formula, C
47H
88N
12O
11•3HCl•H
2O, was indicated by elemental analysis. Amino acid analysis on the acid hydrolyzate demonstrated the presence of 2, 4-diaminobutyric acid (4 moles), serine (1 mole) and leucine (3 moles). Gas chromatographic analysis with the methylated product of the ethereal extract of the acid hydrolyzate revealed the presence of β-hydroxy isodecanoic acid, β-hydroxy decanoic acid, β-hydroxy isoundecanoic acid and β-hydroxyanteisoundecanoic acid. Octapeptin D is active against Gram-negative and Gram-positive bacteria
in vitro and
in viva.
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STUDIES ON ANTIBIOTICS FROM THE GENUS BACILLUS. XXVIII)
TOSHIYUKI KATO, JUN'ICHI SHOJI
1980 Volume 33 Issue 2 Pages
186-191
Published: 1980
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Amino acid analysis of the acid hydrolyzate of octapeptin D revealed the amino acid composition. These amino acids were converted to L-leucyl-derivatives and analyzed by high performance liquid chromatography to clarify their chiralities. These were determined to he: 2, 4-diaminobutyric acid (4L), Ser (D), Leu (2L, 1D). Deacylation with polymyxin acylase afforded deacyl octapeptin D. EDMAN degradation on deacyl octapeptin D revealed the N-terminal amino acid. Application of the chemical cleavage reaction for fragmentation of seryl peptides on tri (DNP)-octapeptin D afforded a DNP-heptapeptide, whose sequence was clarified by EDMAN degradation. Octapeptin D was separated into four components (D
1 D
2, D
3 and D
4) by high performance liquid chromatography. All the components were examined for their amino acid and fatty acid compositions. From the results, the structures of octapeptins D
1, D
2, D
3 and D
4 were determined.
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SEIICHI TANIDA, TORU HASEGAWA, KAZUNORI HATANO, EIJI HIGASHIDE, MASAHI ...
1980 Volume 33 Issue 2 Pages
192-198
Published: 1980
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Ansamitocins are new maytansinoid antitumor antibiotics produced by an actinomycete strain No. C-15003 (N-1). The organism is characterized by coremia formation on solid media, release of the rod-shaped motile spores with peritrichous flagella in liquid media, the formation of some branched mycelia at a later stage of growth in liquid culture which break up into motile elements, lysozyme resistance, the occurrence of
meso-diaminopimelic acid in the cell wall, and guanine-cytosine content of 71±1 mol %. From these results, the organism has been designated as
Nocardia sp. No. C-15003 (N-1). In the fermentation fluids, activity against eukaryotic microorganisms was detected. Three of the purified materials, which have the activity against
Tetrahymena pyriformis strain
W and
Hamigera avellanea IFO 7721, were new ansamycin antibiotics with antileukemic activities and were named ansamitocins P-3, P-3' and P-4. Ansamitocins show growth inhibitory activity against several eukaryotic microorganisms but no activity against prokaryotic microorganisms. The acyl moieties at the C-3 position of ansamitocins are essential for their antifungal activities.
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I. PRODUCING ORGANISM, FERMENTATION AND ANTIMICROBIAL ACTIVITIES
SEIICHI TANIDA, TORU HASEGAWA, EIJI HIGASHIDE
1980 Volume 33 Issue 2 Pages
199-204
Published: 1980
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New antibiotics, macbecins I and II, have been found in the culture fluid of an actinomycete, which has the following properties: delayed fragmentation of vegetative mycelia, formation of coremia on solid media, the occurrence of
meso-diaminopimelic acid in the cell wall, lysozyme resistance, and guanine-cytosine content of 71±1 mol%. The organism has been designated
Nocardia sp. No. C-14919 (N-2001). A marked enhancement of the production of macbecins I and II was observed in cultures containing L-tyrosine. The antibiotics are moderately active against several Gram-positive bacteria and fungi. The antibiotics also inhibit the growth of
Tetrahymena pyriformis W at 2μg/ml but show no activity against the regeneration of cilia in partially deciliated
Tetrahymena at 10μg/ml.
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II. ISOLATION AND CHARACTERIZATION
MASAYUKI MUROI, MOTOWO IZAWA, YOSHIO KOSAI, MITSUKO ASAI
1980 Volume 33 Issue 2 Pages
205-212
Published: 1980
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New antitumor antibiotics, macbecins I and II, were isolated from the culture broth of
Nocardia sp. No. C-14919. Macbecins I and II belong to the ansamycin group and have a benzoquinone and hydroquinone nucleus, respectively. Both showed antitumor activity against murine leukemia P 388
in vivo.
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TAXONOMY, ISOLATION, PHYSICO-CHEMICAL AND BIOLOGICAL PROPERTIES
NORIO EZAKI, SHINJI MIYADOH, TAKASHI HISAMATSU, TAKAO KASAI, YUJIRO YA ...
1980 Volume 33 Issue 2 Pages
213-220
Published: 1980
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BN-183B is a new antitumor antibiotic with chlorine in its molecule found in the culture broth of
Pseudomonas sp. BN-183. The compound was weakly basic and isolated as a hydrochloride in a pure state. The molecular formula of its free base was determined as C
14H
20-
N
2O
6Cl
2. The antibiotic showed not only strong antimicrobial activity against both Gram-positive and Gram-negative bacteria but also marked activity toward experimental tumors such as lymphoid leukemia L-1210 and lymphocytic leukemia P-388 in mice. No mutagenicity of BN-183B was noted.
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II. STUDIES ON DISTRIBUTION AND EXCRETION OF PRUMYCIN
SHUJI OKUBO, NOBUO NAKAMURA, MAKOTO MORIMOTO, KAZUYUKI MINEURA, HIROFU ...
1980 Volume 33 Issue 2 Pages
221-225
Published: 1980
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Tissue distribution, excretion and metabolism of prumycin in normal mice and rats were studied by microbiological assay. Following the injection of prumycin into mice, high activity was detected and continued for 24 hours in the kidney, and the activity was also high in the skin, uterus, bone, liver, lung and stomach in this order. But concentration in the brain, heart, spleen and testis were too low to detect even 5 minutes after the injection. Prumycin was not inactivated by a variety of tissue homogenates
in vitro. Therefore, inability to detect activity of prumycin in the spleen and testis appears to result from poor distribution rather than inactivation by these organs. About 70% of injected prumycin was excreted into rat urine in 24 hours but it was not detectable in feces. When prumycin was injected intravenously into dogs at the dose over 10 mg/kg, vomiting was observed in all animals, and LD
50 was about 50 mg/kg.
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III. MODE OF ACTION OF PRUMYCIN ON HELA S-3 CELLS
SHUJI OKUBO, NOBUO NAKAMURA, MAKOTO MORIMOTO, KAZUYUKI MINEURA, HIROFU ...
1980 Volume 33 Issue 2 Pages
226-230
Published: 1980
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The mode of action of prumycin was investigated using synchronized and asynchronous cultured HeLa S-3 cells. Prumycin inhibited significantly the growth of HeLa S-3 cells at the concentration over 5 mcg/nil. DNA synthesis as well as protein synthesis was strongly inhibited at the concentration of 10 mcg/ml of prumycin, but RNA synthesis was not inhibited by the same concentration. Prumycin did not block the transition of the cells from M phase to G
1 phase, however, G
2 phase cells were blocked clearly by this antibiotic.
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IV. EFFECT OF PRUMYCIN ON MOUSE IMMUNE SYSTEM
SHUJI OKUBO, MAKOTO MORIMOTO, KAZUYUKI MINEURA, HIROFUTO MARUMO, SATOS ...
1980 Volume 33 Issue 2 Pages
231-235
Published: 1980
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The effect of prumycin on the mouse immune system was studied. Prumycin at a dose of 75 mg/kg (1/2LD
50) Showed essentially no suppression of hemolytic plaque forming cells (PFC) against sheep red blood cells (SRBC) when it was administered on day 0, 1 or 2. However, a weak suppression was observed by administration of prumycin on day 3. Also a remarkable suppression of PFC was demonstrated when mouse spleen cells were pre-incubated with prumycin at the concentration over 62.5 mg/kg
in vitro. The delayed-type hypersensitivity reaction against SRBC was remarkably suppressed by cyclophosphamide, but it was not much by prumycin, except by administration on the day of elicitation. Prumycin of a high concentration inhibited an uptake of 3H-thymidine by mouse spleen lymphocytes incubated with or without phytohemagglutinin, but that of a low concentration, 1.9-0.03 mcg/ml, slightly increased the blastogenic stimulation of lymphocytes.
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JUN HAGINAKA, TERUMICHI NAKAGAWA, TOYOZO UNO
1980 Volume 33 Issue 2 Pages
236-243
Published: 1980
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Metabolism and pharmacokinetics of cephaloglycin in man were investigated. High performance liquid chromatographic and gas chromatographic-mass spectrometric analyses of metabolites excreted in human urine following oral administration of cephaloglycin revealed that cephaloglycin was biotransformed in two pathways
i.e. elimination of 3-acetyl group and hydrolysis of side chain amide linkage. The former yielded deacetylcephaloglycin, a part of which further underwent lactonization to deacetylcephaloglycin lactone, and the latter led to benzoyl formic acid
via phenylglycine. The urinary excretion amounts of these metabolites and intact cephaloglycin were determined by a reversed phase ion pair high performance liquid chromatography. The average total excretion amounts at infinite time accounted for 0.50% of the administered dose for intact cephaloglycin, 17.09% for deacetylcephaloglycin, 0.35 for deacetylcephaloglycin lactone, and 0.86% for benzoyl formic acid. The excretion of phenylglycine was less than 0.2%, its chromatographic peak being too small to allow accurate determination. The rate constants for absorption, metabolism, and urinary excretion were estimated by the moment analysis of the excretion rate-time curves.
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KIMIE KOBINATA, MASAKAZU URAMOTO, TAKU MIZUNO, KIYOSHI ISONO
1980 Volume 33 Issue 2 Pages
244-246
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KIYOSHI TSUDA, TSUYOSHI NIHARA, MASAHIRO NISHII, GOTO NAKAMURA, KIYOSH ...
1980 Volume 33 Issue 2 Pages
247-248
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WALTRAUT M. J. KNÖLL, KENNETH L. RINEHART, Jr., PAUL F. WILEY, LI ...
1980 Volume 33 Issue 2 Pages
249-251
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DOUGLAS E. DORMAN, ROBERT L. HAMILL, JOHN L. OCCOLOWITZ, YOSHIHIRO TER ...
1980 Volume 33 Issue 2 Pages
252-255
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BRUCE B. JARVIS, G. PATRICK STAHLY, GOWSALA PAVANASASIVAM, EUUENE P. M ...
1980 Volume 33 Issue 2 Pages
256-258
Published: 1980
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