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NAOKI TSUJI, MASAAKI KOBAYASHI
1978 Volume 31 Issue 10 Pages
939-944
Published: 1978
Released on J-STAGE: April 12, 2006
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In addition to trichostatins A and B, a new antifungal antibiotic, trichostatin C was isolated. The structure was shown to be a glucoside of trichostatin A by spectroscopic examinations and chemical degradations. Trichostatin C is presumably the first example of a glucopyranosyl hydroxamate from nature.
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H. HOEKSEMA, C. LEWIS, S. A. MIZSAK, J. A. SHILEY, D. R. WAIT, H. A. W ...
1978 Volume 31 Issue 10 Pages
945-948
Published: 1978
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Rubradirin B, C
40H
33N
3O
15, was separated from other components of the rubradirin complex
by chromatographic and crystallization procedures. The spectrum of antibacterial activity
is similar to that of rubradirin, but the antibiotic is less active.
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E. MARTINELLI, P. ANTONINI, R. CRICCHIO, G. LANCINI, R. J. WHITE
1978 Volume 31 Issue 10 Pages
949-951
Published: 1978
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J. R. EVANS, EUNICE J. NAPIER, R. A. FLETTON
1978 Volume 31 Issue 10 Pages
952-958
Published: 1978
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A new quinoline compound, G1499-2 [C
18H
21NO(
I)] is produced by
Cytophaga johnsonii. G1499-2 has an unusual structure containing a cyclopropylidene radical. The compound has limited antibiotic activity against a few bacteria. It is not toxic to mice.
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YUZURU IWAI, AKIKO KORA, YOKO TAKAHASHI, TAKAKO HAYASHI, JUICHI AWAYA, ...
1978 Volume 31 Issue 10 Pages
959-965
Published: 1978
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Two antibiotics of frenolicin group, antibiotic AM-3867 I and II were isolated from the fermentation broth of
Streptomyces roseofulvus strain No. AM-3867, a soil isolate. The former was a new antibiotic designated as frenolicin B and its structure containing γ-lactone was determined, while the latter was identified as deoxyfrenolicin having been chemically prepared from frenolicin.
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TAMIO FUJIWARA, TATSUO TANIMOTO, KOICHI MATSUMOTO, EIJI KONDO
1978 Volume 31 Issue 10 Pages
966-969
Published: 1978
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By the use of our improved colony selection technique, xylostasin and ribostamycin producing mutants were isolated from nitrosoguanidine treated Bacillus circulars B15M, a producer of butirosins A and B. Among these structurally related aminoglycosides, ribostamycin is the well-known product of a
Streptomyces and has not been isolated as a bacterial metabolite.
A selected mutant of strain 306, which produces xylostasin and ribostamycin, was further mutagenized in expectation of getting an improved strain having the ability to accumulate a large amount of ribostamycin in the culture broth. One mutant, strain 451, derived from strain 306, produced ribostamycin free of xylostasin.
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K. ECKARDT, D. TRESSELT, W. IHN
1978 Volume 31 Issue 10 Pages
970-973
Published: 1978
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A combination of chemical reactions and NMR data has established the structure of griseorhodin C to be
II.
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13C-NMR SPECTRAL ANALYSIS OF THE INTERGLYCOSIDIC LINKAGES OF THE HETEROTETRASACCHARIDE SIDE-CHAIN
A. NESZMÉLYI, F. SZTARICSKAI, A. LIPTÁK, R. BOGNÁ ...
1978 Volume 31 Issue 10 Pages
974-975
Published: 1978
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By
13C-NMR studies on
Ia,
IIa,
IIb and
IVa obtained by the chemical degradation of
ristomycin A and on several synthetic model compounds it has been proved that an O-β-D-arabinopyranosyl-(1→2)-O-α-D-mannopyranosyl-(1→2)-O-[α-L-rhamnopyranosyl-(1→6)]-D-glucopyranosyl heterotetrasaccharide moiety is connected to the aglycone of the antibiotic.
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9-DEOXY-4(R)-DIHYDROSPECTINOMYCIN AND 9-DEOXYSPECTINOMYCIN
LOUISE FOLEY, JACK T. S. LIN, MANFRED WEIGELE
1978 Volume 31 Issue 10 Pages
979-984
Published: 1978
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A route to 9-deoxyspectinomycin (
12) and 9-deoxy-4(
R)-dihydrospectinomycin (
8) is described.
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9-EPI-4(R)-DIHYDROSPECTINOMYCIN AND 9-EPI-SPECTINOMYCIN
LOUISE FOLEY, JACK T. S. LIN, MANFRED WEIGELE
1978 Volume 31 Issue 10 Pages
985-990
Published: 1978
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The preparation of 9-
epi-4(
R)-dihydrospectinomycin (
8) and of 9-
epi-spectinomycin (
11) is described.
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TAKAYUKI USUI, TSUTOMU TSUCHIYA, SUMIO UMEZAWA
1978 Volume 31 Issue 10 Pages
991-996
Published: 1978
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1-Deamidino-, 3-deamidino- and 1, 3-di(deamidino)dihydrostreptomycin (
1, 2, 3) were prepared by treatment of dihydrostreptomycin (DHSM) with ammonia at 100°C. The 3-guanidino group of DHSM is suggested to be more important than the 1-guanidino group for the antibacterial activity of DHSM. 1-
N-[(
S)-4-Amino-2-hydroxybutyryl] and 1-
N-[(
S)-4-guanidino-2-hydroxybutyryl] derivatives (
4, 6) of 1-deamidinodihydrostreptomycin were further prepared.
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DWIGHT D. WELLER, ARTHUR HABER, KENNETH L. RINEHART Jr.
1978 Volume 31 Issue 10 Pages
997-1006
Published: 1978
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All resonances observed in the
13C NMR spectrum of the antitumor antibiotic pactamycin and its degradation product pactamygate have been assigned, employing off-resonance and specific proton decoupling as well as comparison with the
13C NMR spectra of the model compounds
m-aminoacetophenone and ethyl 6-methylsalicylate.
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ADIL A. OTHMAN, NAJIM A. AL-MASUDI, USAMA S. AL-TIMARI
1978 Volume 31 Issue 10 Pages
1007-1012
Published: 1978
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Three cyclitol derivatives, 2, 4/3-triacetoxycyclohexanone diethyl dithioketal (
XVIII), and 2, 3, 4-tri-O-acetyl-1-O-ethyl-2, 4/1, 3-cyclohexanetetrol (
XXA) and 2, 3, 4-tri-O-acetyl-1-O-ethyl-1, 2, 4/3-cyclohexanetetrol (
XXB), have been synthesized
via the cyclisation of 2, 3, 4-tri-O-acetyl-5, 6-dideoxy-D-
xylo-hex-5-enose diethyl dithioacetal (
XIV) and the cyclisation of 2, 3, 4-tri-O-acetyl-5, 6-dideoxy-D-
xylo-hex-5-enose diethyl acetal (
XV) under ultraviolet or direct sunlight, in aqueous acetone.
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STRUCTURE-ACTIVITY RELATIONSHIPS OF 6-[α-(α'-UREIDOACYLAMINO) ACYLAMINO] PENICILLANIC ACIDS
HARRY FERRES, MICHAEL J. BASKER, DESMOND J. BEST, FRANK P. HARRINGTON, ...
1978 Volume 31 Issue 10 Pages
1013-1022
Published: 1978
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The influence on the structure-activity relationships (S. A. R.) of the stereochemistry and various alkyl, aryl, aralkyl and heterocyclic substituents at the two chiral centres in the dipeptide side-chain of a new series of penicillins was examined. In many cases the effects of these changes had a pronounced influence on the degree of activity against Gram-positive and especially Gram-negative bacteria. Several compounds indicated that the size, shape and spatial disposition of a substituent were the parameters of importance in influencing activity, rather than its lipophilic or electronic character. The most active homologues in the series provided broad-spectrum penicillins which in terms of their
in vitro antibacterial properties showed improvements over certain of the marketed penicillins. Thus 6-[D-α(α'-ureidoacylamino) acylamino]penicillanic acids were found which had a carbenicillin-like profile, with improvements against
Pseudonionas aeruginosa, Klebsiella aerogenes, sensitive and β-lactamaseproducing Gram-positive cocci.
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I. CONVERSION OF NEAMINE ANALOGS INTO BUTIROSIN ANALOGS BY MUTANTS OF BACILLUS CIRCULANS
KATSUO TAKEDA, SATOSHI OKUNO, YOSHITAMI OHASHI, TAMOTSU FURUMAI
1978 Volume 31 Issue 10 Pages
1023-1030
Published: 1978
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By N-methyl-N'-nitro-N-nitrosoguanidine treatment, neamine-negative mutants which required neamine for biosynthesis of butirosins were obtained from a butirosin-producing organism
Bacillus circulars. These mutants also produced butirosins from paromamine and could be divided into two types I and II. Mutants of type I could not produce butirosins from 2-deoxystreptamine, whereas those of type II could. Two typical mutants MCRL 5003 (type I) and MCRL 5004 (type II) could produce butirosin analogs, 3', 4'-dideoxybutirosins, 6'-N-methylbutirosins, 3', 4'-dideoxy-6'-N-methylbutirosins and 3', 4'-dideoxy-6'-C-methylbutirosins from neamine analogs, gentamine C
1a, 6'-N-methylneamine, 6'-N-methylgentamine C
1a, and gentamine C
2, respectively.
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II. 3', 4'-DIDEOXY-6'-N-METHYLBUTIROSINS, NEW SEMISYNTHETIC AMINOGLYCOSIDES
KATSUO TAKEDA, AKIO KINUMAKI, HARUO HAYASAKA, TOUTARO YAMAGUCHI, YUKIO ...
1978 Volume 31 Issue 10 Pages
1031-1038
Published: 1978
Released on J-STAGE: April 12, 2006
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A pair of new butirosin analogs was isolated from the fermentation broth obtained by cultivating a neamine-negative mutant of the butirosin-producing organism
Bacillus circulans in the medium supplemented with 6'-N-methylgentamine C
1a. These antibiotics were characterized and elucidated as 3', 4'-dideoxy-6'-N-methylbutirosins A and B (DMB-A & DMB-B), by chemical and spectroscopic studies. DMB-A and DMB-B exhibited broad-spectrum antibacterial activities with
in vitro potency similar to or slightly less than that for the butirosin A, with the exception of strains of
Pseudomonas aeruginosa and
Serratia marcescens against which they exhibited activities equal to or slightly greater than that for butirosin A. As expected, they exhibited stronger activities against butirosin-resistant organisms which contain acetylating enzymes AAC(6')-I and AAC(6')-IV, and phosphorylating enzyme APH(3')-II. They were also active against some of the clinical isolates resistant to butirosins, dibekacin and/or gentamicin. The acute intravenous toxicity in mice of the DMB complex (B: 70-80%) was somewhat less than that of the butirosin A.
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III. 6'-N-METHYLBUTIROSINS AND 3', 4'-DIDEOXY-6'-C-METHYLBUTIROSINS, NEW SEMISYNTHETIC AMINOGLYCOSIDES
KATSUO TAKEDA, AKIO KINUMAKI, SATOSHI OKUNO, TADAHIRO MATSUSHITA, YUKI ...
1978 Volume 31 Issue 10 Pages
1039-1045
Published: 1978
Released on J-STAGE: April 12, 2006
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Two pairs of butirosin analogs were isolated from the fermentation broths obtained by cultivating a neamine-negative mutant of the butirosin-producing organism
Bacillus circulars in the medium supplemented with 6'-N-methylneamine and gentamine C
2, respectively. These antibiotics were characterized as 6'-N-methylbutirosins A and B (NMB-A & NMB-B), and 3', 4'-dideoxy-6'-C-methylbutirosins A and B (DCB-A & DCB-B), respectively, by chemical and spectroscopic studies. NMB-A and NMB-B exhibited broad-spectrum antibacterial activities with
in vitro potency similar to or slightly less than that for butirosin A, but with greater activities against butirosin-resistant strain which contains acetylating enzyme AAC- (6')-I. The activities of NMB-A and NMB-B against
Pseudomonas aeruginosa strains were relatively weak. DCB-B had broad-spectrum activity, and exhibited greatly improved activity against butirosin-resistant organisms which contain acetylating enzymes AAC(6')-I and AAC(6')-IV, and phosphorylating enzyme APH(3')-II. These new butirosin analogs were also active against some of the clinical isolates resistant to butirosins, dibekacin and/or gentamicin.
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HANS H. GADEBUSCH, R. SCHWIND, P. LUKASZOW, R. WHITNEY, R. J. MCRIPLEY
1978 Volume 31 Issue 10 Pages
1046-1058
Published: 1978
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SQ 14, 359 is a new cephamycin-type (7α-OCH
3) antibiotic belonging to a series containing a 7α-ureidoacetyl substituent. The compound is the most potent extended spectrum derivative of this type yet reported, surpassing CS-1170 and cefoxitin by a wide margin. This activity in vitro which extends throughout the Enterobacteriaceae is particularly prominent against Gram-negative organisms that are producers of "cephalosporinase-type" β-lactamases such as Enterobacter, Serratia, Citrobacter and indole-positive Proteus species. Superior activity also is demonstrated in vitro against streptococci, β-lactamase-producing staphylococci,
Haemophilus influenzae, Neisseria gonorrhoeae, and many Gram-negative pathogens resistant to aminoglycoside antibiotics. Experimental chemotherapeutic studies have confirmed these observations in wound and selected systemic infections in mice as well as acute pyelonephritis and meningitis in rats. The pharmacokinetics for each drug including antibiotic bound to serum was similar in both mice and rats. The pharmacokinetic profile in blood and cerebrospinal fluid favored SQ 14, 359.
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JAMES A. MAJESKI, MICHAEL J. MORRIS, J. WESLEY ALEXANDER
1978 Volume 31 Issue 10 Pages
1059-1062
Published: 1978
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Polymorphonuclear neutrophilic leukocyte chemotaxis was examined
in vitro in the presence of two new antibiotics: cefamandole and cefoxitin. Results indicate that cefamandole inhibited neutrophil chemotaxis to a significant degree only at high antibiotic concentrations of 100 μg/ml (P<0.01) and has no significant effect at normal serum therapeutic range. Cefoxitin was found to produce a 43% inhibition (P<0.01) of human
in vivo neutrophil chemotaxis at antibiotic concentrations of 100 μg/ml and have a minimal inhibitory effect (1-9%) at low concentrations (1-5 μg/ml). Both cefamandole and cefoxitin had no significant effect on opsonophagocytosis.
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CHATRCHAI WATANAKUNAKORN
1978 Volume 31 Issue 10 Pages
1063-1064
Published: 1978
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KATSUYOSHI YONEYAMA, SHIGEKO SEKIDO, TOMOMASA MISATO
1978 Volume 31 Issue 10 Pages
1065-1066
Published: 1978
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H. HOEKSEMA, C. CHIDESTER, S. A. MIZSAK, L. BACZYNSKYJ
1978 Volume 31 Issue 10 Pages
1067-1069
Published: 1978
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YOICHI IITAKA, HIKARU NAKAMURA, TOKUJI NAKATANI, YASUHIKO MURAOKA, AKI ...
1978 Volume 31 Issue 10 Pages
1070-1072
Published: 1978
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TOMOHISA TAKITA, YASUHIKO MURAOKA, TOKUJI NAKATANI, AKIO FUJII, YOICHI ...
1978 Volume 31 Issue 10 Pages
1073-1077
Published: 1978
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