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THE ISOLATION AND PRELIMINARY CHEMICAL CHARACTERIZATION OF ACTAPLANIN
MANUEL DEBONO, KURT E. MERKEL, R. MICHAEL MOLLOY, MITCHELL BARNHART, E ...
1984 年 37 巻 2 号 p.
85-95
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Actaplanin (A4696), a new complex of broad spectrum Gram-positive antibiotics is produced by
Actinoplanes inissouriensis. High performance liquid chromatography was used to show that this complex is composed of several actaplanins. Hydrolytic experiments with actaplanins A, B
1, B
2, B
3, C
1 and G showed that these actaplanins were composed of the same peptide core, an amino sugar and varying amounts of glucose, mannose and rhamnose. The neutral sugar content was determined for each actaplanin. A bioautographic study of aglycone formation during hydrolysis of the actaplanin complex showed that within a short time a simple mixture of two antimicrobially active hydrolysis products was obtained. These substances retained the antimicrobial spectrum and a high percentage of the antibiotic activity of the parent actaplanin complex. Methanolysis of the actaplanin complex as well as the individual actaplanins resulted in the selective loss of the neutral sugar moieties and the isolation of actaplanin Ψ(pseudo)-aglycone-the core peptide which still retained an amino sugar group. The
1H NMR spectrum of this substance indicated a similarity to many features of ristocetin Ψ-aglycone. Hydrolytic studies showed that the amino sugar present in actaplanin was identical with L-ristosamine. It is concluded that the aglycone of actaplanin is a complex peptide composed of aromatic amino acids, and that the actaplanins each possess this aglycone and L-ristosamine but are differentiated by their neutral sugar composition.
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L. A. DOLAK, T. M. CASTLE, B. R. HANNON, F. REUSSER
1984 年 37 巻 2 号 p.
96-102
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Antibiotic U-64846 is a new entity with the molecular formula C
18H
35ClN
4O
9 (MW 486). It is a very water soluble, reddish solid which decomposes above 300°C and which is air-sensitive. The antibiotic is produced by
Streptomyces braegensis and it inhibits a variety of Gram-positive bacteria. Acidic hydrolysis gave 3, 7-diaminoheptanoic acid. The antibiotic gives
1H NMR,
13C NMR, IR and UV spectra which indicate it is not closely related to known antibiotic families.
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TADASHI ARAI, JUN UNO, IICHIRO HORIMI, KAZUTAKA FUKUSHIMA
1984 年 37 巻 2 号 p.
103-109
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Fermentation of
Streptomyces hygroscopicus var.
crystallogenes, the copiamycin source, yielded several minor components with antifungal activity. One of these minor components, neocopiamycin A, was isolated and characterized. The structure of neocopiamycin A was determined as
N-demethylcopiamycin on the basis of spectroscopic evidence. The antibiotic was found to be more active against Gram-positive bacteria and fungi but less toxic than copiamycin.
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BAFILOMYCINS, A NEW GROUP OF MACROLIDE ANTIBIOTICS PRODUCTION, ISOLATION, CHEMICAL STRUCTURE AND BIOLOGICAL ACTIVITY
GERHARD WERNER, HANSPAUL HAGENMAIER, HANNELORE DRAUTZ, ANGELIKA BAUMGA ...
1984 年 37 巻 2 号 p.
110-117
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
The bafilomycins A
1, A
2, B
1, B
2, C
1 and C
2, a new type of macrolide antibiotics with a 16-membered lactone ring, were isolated from the fermentation broth of three
Streptomyces griseus strains (TÜ 1922, TÜ 2437, TÜ 2599) by ethyl acetate extraction and column chromatography on silica gel. The bafilomycins exhibit activity against Gram-positive bacteria and fungi. Physico-chemical data, chemical structures and biological activities are reported.
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I. MICROBIAL DEEPOXIDATION AND SUBSEQUENT ISOMERIZATION OF DELTAMYCINS A1, A2, A3, A4 (CARBOMYCIN A) AND X
YASUO FUKAGAWA, YOSHIFUMI MUTOH, TOMOYUKI ISHIKURA, JOSEPH LEIN
1984 年 37 巻 2 号 p.
118-126
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Carbomycin A (deltamycin A
4) was deepoxidized to carbomycin A P1 by
Streptomyces halstedii subsp.
deltae (a deltamycins producer), favorably under anaerobic conditions. Carbomycin A P1 was spontaneously converted to geometric isomers designated carbomycins A P2 and A P3. This type of deepoxidation and subsequent isomerization was not limited to carbomycin A, but generally occurrable in other 16-membered epoxyenone macrolide compounds. Many bacteria and actinomycetes were also found to have an ability to deepoxidize deltamycins reductively. The chemical structures of carbomycins A P1, A P2 and A P3 were elucidated as shown in Fig. 3.
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II. CHEMICAL DEEPOXIDATION BY DISSOLVING METAL REDUCTION
YOSHIFUMI MUTOH, YASUTAKA SHIMAUCHI, YASUO FUKAGAWA, TOMOYUKI ISHIKURA ...
1984 年 37 巻 2 号 p.
127-129
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
16-Membered epoxyenone macrolide antibiotics were reductively deepoxidized with dissolving metals such as zinc. Angolamycin and rosamicin which have a methyl substituent at C-12 in the epoxyenone structure were deepoxidized, but not isomerized further to the geometric isomers P2 and P3.
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III. IN VITRO AND IN VIVO EVALUATION OF DEEPOXIDATION PRODUCTS OF CARBOMYCIN A, DELTAMYCIN A1, 4″-PHENYLACETYLDELTAMYCIN, ANGOLAMYCIN AND ROSAMICIN
MICHIKO SAKAMOTO, YOSHIFUMI MUTOH, YASUO FUKAGAWA, TOMOYUKI ISHIKURA, ...
1984 年 37 巻 2 号 p.
130-135
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Deepoxidation products P1, P2 and P3 of carbomycin A, deltamycin A
1 and 4″-phenylacetyldeltamycin showed high
in vitro antibacterial and antimycoplasmal activities which were comparable to those of the respective parent compounds. By contrast, the
in vitro antimicrobial potencies of angolamycin P1 and rosamicin P1 were about ten-fold lower than those of the parent macrolides. In mice, the increase in the plasma levels of the epoxyenone macrolides due to deepoxidation was highly significant with the P1, P2 and P3 derivatives of carbomycin A and 4″-phenylacetyldeltamycin, whereas angolamycin P1 gave a moderately-improved plasma level compared with angolamycin.
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O. K. SEBEK, L. A. DOLAK
1984 年 37 巻 2 号 p.
136-142
発行日: 1984年
公開日: 2006/04/19
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フリー
A new soil actinomycete (UC 5762, NRRL 11111) was found to transform novobiocin to 11-hydroxynovobiocin. The product was isolated by solvent extraction and column chromatography, and identified by IR, UV,
1H NMR and
13C NMR spectroscopy. Related structures (8, 9-dihydronovobiocin, novobiocic acid and chlorobiocin) were similarly transformed to their corresponding C-11 hydroxylated analogues. The microbial process is superior to chemical (selenium dioxide) oxidation which yielded a mixture of 11-hydroxy- and 11-oxonovobiocin.
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JEAN-MARC GIRODEAU, ROLAND PINEAU, MARYSE MASSON, FRANCOIS LE GOFFIC
1984 年 37 巻 2 号 p.
143-149
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Lividamine and paromamine were converted into two key intermediate ethylenic aldehydes
10a and
10b. Reductive amination of the two aldehydes yielded the protected sisamine
11a and the three analogs
11b, 12a and
12b. These four derivatives were deprotected to yield the four pseudodisaccharides
1a, 1b, 2a and
2b which were less active
in vitro than neamine against
Escherichia coli ATCC 9637 and
Staphylococcus aureus 209P.
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JEAN-MARL GIRODEAU, ROLAND PINEAU, MARYSE MASSON, FRANCOIS LE GOFFIC
1984 年 37 巻 2 号 p.
150-158
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
The three protected sisamine derivatives
2i,
2j and
3, with a free 5-hydroxyl group, have been synthesized. Glycosylation at the 5 position with various pentofuranose derivatives yielded after deprotection of the
6a-i ribostamycin related aminoglycoside. These pseudotrisaccharides showed only low antibacterial activities with respect to the parent compounds.
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MARILYN K. SPEEDIE, DONNA L. HARTLEY
1984 年 37 巻 2 号 p.
159-166
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
The enzyme activities which catalyze the conversion of tryptophan to β-methyltryptophan by two different routes have been demonstrated in cell-free extracts of streptonigrin-producing
Streptomyces flocculus. The first route involves direct methylation of tryptophan by a
C-methyltransferase. The second involves transamination of tryptophan to indolepyruvate, methylation of indolepyruvate to β-methylindolepyruvate, followed by a reverse transamination reaction to yield β-methyltryptophan. The direct methylation route was confirmed by the fact that the methyltransferase activity is still present after the transaminase has been inactivated by hydroxylamine treatment. The L-tryptophan
C-methyltransferase has been purified 30-fold by ammonium sulfate precipitation and a Sephadex G-150 column. The indolepyruvate
C-methyltransferase activity copurified with the tryptophan
C-methyltransferase activity, but the transaminase did not. These results show that a metabolic grid exists for the first antibiotic-committed step of the streptonigrin biosynthetic pathway.
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HEBE B. GREIZERSTEIN, ALBERT J. SIEMENS
1984 年 37 巻 2 号 p.
167-171
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
The effect of cefoperazone on ethanol and acetaldehyde metabolism was studied in rat liver homogenates and with a purified aldehyde dehydrogenase. Rat liver homogenates were incubated with ethanol (30 mM) alone or in combination with cefoperazone (15 or 150 μg/g liver). Ethanol and acetaldehyde concentrations were determined at 6, 12, 18 and 24 minutes. Cefoperazone added to the incubation medium inhibited ethanol and acetaldehyde metabolism in a concentration-dependent manner. The addition of cefoperazone to rat liver homogenates incubated with acetaldehyde (300 μM), however, did not inhibit acetaldehyde disappearance for a period of 15 minutes. Purified aldehyde dehydrogenase was incubated with 300 μM acetaldehyde. When cefoperazone was added, acetaldehyde disappearance was significantly slower than without cefoperazone. The data indicate that cefoperazone inhibits ethanol metabolism in rat liver homogenates in a concentration-dependent manner. The effect of the antibiotic on acetaldehyde elimination in liver homogenate, however, depends on the concentration of acetaldehyde in the medium. The acetaldehyde dehydrogenase obtained from yeast is inhibited by cefoperazone.
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F. BESSON, F. PEYPOUX, M. J. QUENTIN, G. MICHEL
1984 年 37 巻 2 号 p.
172-177
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
Iturin A and bacillomycin L, antibiotics of the iturin group inhibit the growth of
Saccharomyces cerevisiae and the lethal doses were respectively 10 and 60 μg/ml. Both antibiotics had an effect on the incorporation of radioactive precursors into macromolecules which decreased with increasing concentrations of antibiotics. However, no specificity was observed on the various macromolecules, proteins, ribonucleic acids and polysaccharides. The site of action on yeast cells was demonstrated to be the cytoplasmic membrane: both antibiotics of iturin group lysed spheroplasts of
S. cerevisiae. Moreover, a rapid leakage of potassium ions occurred in the presence of the antibiotics; this leakage was directly associated to the killing effect. These results are consistent with a disruption of the structural integrity of the cytoplasmic membrane correlated to the loss of viability of the yeast cells.
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SATISH K. ARORA, PETER MAIN
1984 年 37 巻 2 号 p.
178-181
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
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III. STRUCTURE DETERMINATION OF NEW TRESTATIN COMPONENTS Ro 09-0766, Ro 09-0767 AND Ro 09-0768
KAZUTERU YOKOSE, MAYUMI OGAWA, KIYOSHI OGAWA
1984 年 37 巻 2 号 p.
182-186
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー
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I. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 6-O- METHYLERYTHROMYCINS A
SHIGEO MORIMOTO, YOKO TAKAHASHI, YOSHIAKI WATANABE, SADAFUMI OMURA
1984 年 37 巻 2 号 p.
187-189
発行日: 1984年
公開日: 2006/04/19
ジャーナル
フリー