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I. TAXONOMY, FERMENTATION AND BIOLOGICAL ACTIVITY
W. M. MAIESE, J. KORSHALLA, J. GOODMAN, M. J. TORREY, S. KANTOR, D. P. ...
1990 Volume 43 Issue 9 Pages
1059-1063
Published: September 25, 1990
Released on J-STAGE: April 19, 2006
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A new antibacterial antibiotic, designated simaomicin α (LL-D42067 α) was isolated from the fermentation broth of an actinomycete strain. Based on cultural, physiological, morphological and chemical characteristics, culture LL-D42067 was identified as a new subspecies of
Actinomadura madurae. Simaomicin α demonstrated potent activity against Gram-positive bacteria and was active
in vivo against a variety of
Eimeria species causing coccidiosis in chickens.
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KAZUSHI OSHINO, HIDETOSHI KUMAGAI, HIROSHI TOMODA, SATOSHI OMURA
1990 Volume 43 Issue 9 Pages
1064-1068
Published: September 25, 1990
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Atpenin B, a new antifungal antibiotic produced by
Penicillium sp. FO-125, inhibited the growth of Raji cells (IC
50, 30 μM).The incorporation of [
14C]leucine and [
3H]thymidine into Raji cells was inhibited by atpenin B with IC
50 values of 0.10 and 0.12 μM, respectively. The incorporation of [
14C]palmitate into the cells was not inhibited but its incorporation into lipid fractions was inhibited by atpenin B (IC
50, 0.13-0.24 μM). Studies on the site of atpenin B action demonstrated that atpenin B decreases the cellular adenosine 5'-triphosphate (ATP) level in Raji cells with IC
50 value of 0.020 μM, suggesting the inhibition of ATP-generating system by atpenin B.
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II. ISOLATION, CHARACTERIZATION, STRUCTURE ELUCIDATION AND SOLUTION CONFORMATIONS
G. H. BAKER, R. J. J. DORGAN, J. R. EVERETT, J. D. HOOD, M. E. POULTON
1990 Volume 43 Issue 9 Pages
1069-1076
Published: September 25, 1990
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A novel series of milbemycin antibiotics were isolated from the fermentation broth of a
Streptomyces species designated E225. The structures of the four main metabolites VM 44857 (
1), VM 44864 (
2), VM 44865 (
3) and VM 44866 (
4) were determined by NMR techniques. In addition we describe the solution conformations of the major metabolite VM 44857 (
1).
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TADASHI EGUCHI, HUI-YIN LI, JUN-ICHI KAZAMI, KATSUMI KAKINUMA, NOBORU ...
1990 Volume 43 Issue 9 Pages
1077-1081
Published: September 25, 1990
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The temperature-dependent and concentration-dependent
1H NMR studies as well as
13C-relaxation experiments on gilvocarcin V tetraacetate strongly suggest intermolecular stacking of the antibiotic in solution.
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JÜRGEN K. KETTENRING, ADRIANO MALABARBA, KÁROLY VÉK ...
1990 Volume 43 Issue 9 Pages
1082-1088
Published: September 25, 1990
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By combination of several
1H NMR techniques, the sequence of actagardine has been elucidated. It has been shown that it is a tetracyclic 19-residue peptide antibiotic. It differs from the previously described lanthionine-containing peptide antibiotics belonging to the lantibiotic class.
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ADRIANO MALABARBA, ROSETTA PALLANZA, MARISA BERTI, BRUNO CAVALLERI
1990 Volume 43 Issue 9 Pages
1089-1097
Published: September 25, 1990
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A series of basic carboxamides of actagardine (
1), a lantibiotic possessing good antistreptococcal activity, were synthetized. Some physico-chemical characteristics, in particular charge and lipophilicity, that influence water solubility were determined. The
in vitro and
in vivo activity was evaluated. The monocarboxamides were generally more active than actagardine against selected Gram-positive bacteria. The 3, 3-dimethylamino-l-propylamide hydrochloride (
4) showed good water solubility, bactericidal action and favourable antibacterial activity and it appears to be a suitable drug for further investigation.
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ANDRZEJ CZERWINSKI, WILFRIED A. KÖNIG, PAWEL SOWINSKI, LEONARD FA ...
1990 Volume 43 Issue 9 Pages
1098-1100
Published: September 25, 1990
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Synthesis and biological properties of amphotericin B
O-methyl oxime are described. The presence of an intact hemiketal ring in the antibiotic molecule appeared to be essential for its biological activity.
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MINORU YOSHIDA, YUTAKA HOSHIKAWA, KOSHI KOSEKI, KENJI MORI, TERUHIKO B ...
1990 Volume 43 Issue 9 Pages
1101-1106
Published: September 25, 1990
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Biological activities of four chemically synthesized trichostatin-related compounds, (
R)-trichostatin A, (
S)-trichostatm A, (
R)-trichostatic acid, and (
S)-trichostatic acid, were investigated. Assays of differentiation-inducing activity in Friend leukemia cells and G
2-arresting activity in the cell cycle of normal rat fibroblast cells were used as monitoring systems for comparing the bioactivities of these compounds. The results clearly showed that both of the enantiomers of trichostatic acid had no activity in both the assay systems. In the case of (
S)-trichostatin A, the antipode of naturally occurring trichostatin A, 50% effective concentrations were determined to be 50-70-fold higher than those of (
R)-trichostatin A. The relationship between this ratio and the value of enantiomeric excess strongly suggests that (
S)-trichostatin A is also biologically inactive. These results indicate that the absolute configuration and the presence of the hydroxamate group of trichostatin A are essential for its biological activity.
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ADRIANO MALABARBA, ALDO TRANI, JÜRGEN KETTENRING, ERMINIO GERLI, ...
1990 Volume 43 Issue 9 Pages
1107-1121
Published: September 25, 1990
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The synthesis and the biological properties of a series of
N15-alkyl and
N15,
N15-dialkyl derivatives of teicoplanin A2, its pseudoaglycones and aglycone are described.
The alkylation of the terminal amino group did not affect the ability of these teicoplanin derivatives to bind with Ac
2-L-Lys-D-Ala-D-Ala, a synthetic model of the antibiotic's target peptide in bacterial cell walls, but influenced their
in vitro and
in vivo antimicrobial activities to a different extent, depending on the structure and length of the alkyl chains and the type and number of sugars present.
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VI. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 3-(3-ISOXAZOLYL)OXYMETHYL CEPHALOSPORIN DERIVATIVES
EIJI NAKAYAMA, KATSUHIKO WATANABE, MASAO MIYAUCHI, KOICHI FUJIMOTO, JU ...
1990 Volume 43 Issue 9 Pages
1122-1130
Published: September 25, 1990
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The synthesis and biological activities of a series of 3-(isoxazol-3-yl)oxymethyl cephalosporins are described. 7-[2-(2-Aminothiazol-4-yl)-(
Z)-2-methoxyiminoacetamido] -3- [ (isoxazol-3-yl)oxy- methyl]-3-cephem-4-carboxylic acid (
7a) showed potent activity against both Gram-positive and Gram-negative bacteria including some β-lactamase producing species. Its pivaloyloxymethyl ester provided a good urinary recovery after oral administration to mice.
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A. F. CACCIAPUOTI, D. LOEBENBERG, E. L. MOSS, F. W. MENZEL, J. A. RUDE ...
1990 Volume 43 Issue 9 Pages
1131-1136
Published: September 25, 1990
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A series of tylosins and acyl derivatives of 23-
O-demycinosyltylosin (DMT) were initially tested for
in vitro antibacterial activity and serum levels in squirrel monkeys (po) and mice (iv). Overall, the DMT compounds were more active
in vitro than the tylosins. Two tetraacylated DMTs, Sch 37644 and Sch 38646, were selected from the initial studies for further evaluation and compared to erythromycin and A-56268 (6-
O-methyl erythromycin). Sch 37644 and Sch 38646 were 2 to 8-fold less potent
in vitro against Gram-positive bacteria than erythromycin and A-56268. In squirrel monkeys, Sch 37644 (AUC, 19.7 μg•hour/ml) and A-56268 (21.6 μg•hour/ml) had similar serum levels following po administration of 20 mg/kg, while Sch 38646 (11.8 μg•hour/ml) and erythromycin (1.5 μg•hour/ml) had lower levels. In mice administered 200mg/kg orally, Sch 37644 (AUC, 19.4 μg•hour/ml) and Sch 38646 (15.4 μg•hour/ml) had higher serum levels than erythromycin (5.7 μg•hour/ml). A-56268 was the most active po macrolide in mouse protection studies (PD
50s) against Staphylococci and Streptococci, while Sch 37644 and Sch 38646 were similar to erythromycin.
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DAVID F. CORBETT, STEVEN COULTON, DAVID J. KNOWLES, ROBERT SOUTHGATE
1990 Volume 43 Issue 9 Pages
1137-1149
Published: September 25, 1990
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A number of C-2 aminoalkenylthio-carbapenem derivatives possessing both the (5
R, 6
R, 8
S)- and the (5
R, 6
S, 8
R)-stereochemistries have been prepared from the olivanic acids MM 22382 and MM 22383, respectively. Certain members of this new class of compounds displayed potent, broad spectrum antibacterial activity as well as improved stability to human kidney homogenate.
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KIYOAKI KATANO, HIROKO OGINO, KATSUYOSHI IWAMATSU, SATORU NAKABAYASHI, ...
1990 Volume 43 Issue 9 Pages
1150-1159
Published: September 25, 1990
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Substituted (cyclopentenopyridinium)thiomethyl groups were introduced as C-3 substituents of (6
R, 7
R)-7-[(
Z)-2-(2-aminothiazol-4-yl)-2-oxyimino] acetamidocephalosporins. Structure-activity relationships of this class of cephalosporins are discussed on the basis of their MIC. The selected compounds,
3a and
4a (ME1221), having an acidic substituent, showed excellent
in vivo efficacy and low toxicity.
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SHINTARO NISHIMURA, NOBUYOSHI YASUDA, HIROSHI SASAKI, KOHJI KAWABATA, ...
1990 Volume 43 Issue 9 Pages
1160-1168
Published: September 25, 1990
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The synthesis and biological properties of some 3-vinylthio- and 3-vinylthiomethylcephem derivatives are described. Both series possess potent antibacterial activity. Among them, 3-[(
Z)-2-cyanovinylthiomethyl]cephem derivative was found to have an expanded antibacterial spectrum.
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JÜRGEN ROHR, AXEL ZEECK
1990 Volume 43 Issue 9 Pages
1169-1178
Published: September 25, 1990
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The structure-activity relationships of the anthracycline-related antibiotics of the tetracenomycin C/elloramycin-type were investigated by derivatization of elloramycin (
1) and elloramycinone (
2). During hydrolysis experiments a unique transglycosylation reaction was discovered, converting elloramycin (
1) into isoelloramycin (
10) by treatment with anhydrous trifluoroacetic acid. Following the proposed structure-activity relationship concept, 8-
O-methylelloramycinone (
14) was synthesized from elloramycinone (
2), and was shown to be the most active derivative according to the proliferation inhibition assay against murine L1210 leukemia cells.
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JAMES M. SCHAEFFER, EASTER G. FRAZIER, ALAN R. BERGSTROM, JOANNE M. WI ...
1990 Volume 43 Issue 9 Pages
1179-1182
Published: September 25, 1990
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Cochlioquinone A, isolated from the fungus
Helminthosporium sativum, was found to have nematocidal activity. Cochlioquinone A is a competitive inhibitor of specific [
3H]ivermectin binding suggesting that cochlioquinone A and ivermectin interact with the same membrane receptor.
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TOSHIRO IWAMOTO, AKIHIKO FUJIE, YASUHISA TSURUMI, KUMIKO NITTA, SEIJI ...
1990 Volume 43 Issue 9 Pages
1183-1185
Published: September 25, 1990
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III. EFFECTS OF WF-3681 AND ITS DERIVATIVES ON SORBITOL ACCUMULATION IN DIABETIC RATS
MOTOAKI NISHIKAWA, KEIZO YOSHIDA, MASANORI OKAMOTO, MASANOBU KOHSAKA
1990 Volume 43 Issue 9 Pages
1186-1188
Published: September 25, 1990
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F. VAUFREY, A. M. DELORT, G. JEMINET, G. DAUPHIN
1990 Volume 43 Issue 9 Pages
1189-1191
Published: September 25, 1990
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TAKASHI NOGAMI, YASUHIRO SHIGIHARA, NAOKO MATSUDA, YOSHIKAZU TAKAHASHI ...
1990 Volume 43 Issue 9 Pages
1192-1194
Published: September 25, 1990
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KUNIO ISSHIKI, TSUTOMU SAWA, HIROSHI NAGANAWA, YUMI KOIZUMI, NAOKO MAT ...
1990 Volume 43 Issue 9 Pages
1195-1198
Published: September 25, 1990
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MICHAEL R. BARBACHYN, TERRENCE C. TUOMINEN
1990 Volume 43 Issue 9 Pages
1199-1203
Published: September 25, 1990
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YOSHIHIKO YAGI
1990 Volume 43 Issue 9 Pages
1204-1205
Published: September 25, 1990
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