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I. DISCOVERY, FERMENTATION AND ANTIBACTERIAL ACTIVITY
ROBERT J. THERIAULT, RONALD R. RASMUSSEN, WILLIAM L. KOHL, JOSEPH F. P ...
1986 Volume 39 Issue 11 Pages
1509-1514
Published: 1986
Released on J-STAGE: April 19, 2006
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Nocardia lurida has been shown to produce two novel quinone antibiotics, benzanthrins A and B. The antibiotics were discovered in concentrated butanol extracts of fermentation broths and were separated by TLC and HPLC. Benzanthrins A and B were produced in a fermentation medium consisting of glucose, yeast, selected peptones and CaCO
3. The antibiotics were present primarily at 66 hours in shake flask fermentations and from 66 to 162 hours in 14-liter fermentors. Benzanthrins A and B inhibited a number of Gram-positive pathogenic bacteria but were inactive against Gram-negative bacteria.
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II. ISOLATION, ELUCIDATION OF STRUCTURE AND POTENTIAL ANTITUMOR ACTIVITY
RONALD R. RASMUSSEN, MERRILL E. NUSS, MICHAEL H. SCHERR, SANDRA L. MUE ...
1986 Volume 39 Issue 11 Pages
1515-1526
Published: 1986
Released on J-STAGE: April 19, 2006
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The benzanthrins, which were produced by
Nocardia lurida, were extracted from the fermentation broth with CH
2Cl
2. Subsequent purification on Sephadex LH-20 and diolbonded silica gel, followed by countercurrent chromatography, afforded analytically pure benzanthrins A and B. FAB-MS revealed that benzanthrins A and B were isomeric. It was demonstrated through degradative and spectroscopic studies that the benzanthrins were diglycosides of a trihydroxy benz[a]anthraquinone chromophore where one of the sugars was linked through carbon and the other through oxygen. Benzanthrins A and B differed in the stereochemistry of the
O-glycosidic sugar. Both compounds inhibited the growth of Gram-positive bacteria and 9KB, 9PS and 9ASK tumor cells in tissue culture.
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I. PRODUCING ORGANISM, FERMENTATION, ISOLATION, AND CHARACTERIZATION
KATSUHIKO NAGAOKA, MASARU MATSUMOTO, JUNJI OONO, KOUICHI YOKOI, SEIJI ...
1986 Volume 39 Issue 11 Pages
1527-1532
Published: 1986
Released on J-STAGE: April 19, 2006
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A strain of
Streptomyces griseofuscus S42227 (FERM P-8443) was found to produce new antitumor antibiotics, called azinomycins A and B. The molecular formulas of azinomycins A and B were determined as C
30H
33N
3O
10 and C
31H
33N
3O
11, respectively. They were active against Gram-positive bacteria, Gram-negative bacteria and L5178Y cells in tissue culture.
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LAVERNE D. BOECK, FREDERICK P. MERTZ
1986 Volume 39 Issue 11 Pages
1533-1540
Published: 1986
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A47934, a novel glycopeptide-aglycone antibiotic, is produced by a strain of
Streptomyces toyocaensis, NRRL 15009. A47934 is unique among reported glycopeptides in that it contains a sulfate ester. Like several other glycopeptides, the majority of the A47934 produced remained associated with the producing biomass, from which it could be released into aqueous media by alkalization. Antibiotic biosynthesis was depressed when initial levels of phosphate phosphorus in the medium exceeded the normal level of 35 μg/ml. Enrichment of the fermentation medium with tyrosine depressed A47934 yields while enrichment with
p-hydroxyphenylglycine or
p-hydroxyphenylglyoxylic acid stimulated antibiotic biosynthesis.
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II. DECARBOXYLATION, ABNORMAL KETALIZATION AND DEHYDRATION
W. J. MCGAHREN, G. O. MORTON, M. M. SIEGEL, D. B. BORDERS, J. C. JAMES ...
1986 Volume 39 Issue 11 Pages
1541-1550
Published: 1986
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The behavior of the free acid and ammonium salt of maduramicin towards heat and alcohols is examined. In refluxing lower alcohols the free acid material is decarboxylated. In addition a bisketal decarboxylated compound as well as an A-ring monoketal decarboxylated derivative are formed. Heating the ammonium salt of the ionophores in suspension in water, or dissolved in inert solvents such as heptane or xylene can cause decarboxylation as well as concomitant dehydration of the F-ring. Reaction of dansyl chloride with the free acid of maduramicin can cause dehydration of the B-ring under very mild conditions.
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ISAO KAWAMOTO, ROKURO ENDO, SHINICHI SUGAWARA
1986 Volume 39 Issue 11 Pages
1551-1556
Published: 1986
Released on J-STAGE: April 19, 2006
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The synthesis and
in vitro antimicrobial activity of a new penem antibiotic, sodium (5
R, 6
S)-2-(2-fluoroethylthio)-6-[(1
R)-1-hydroxyethyl]penem-3-carboxylate (1), are reported. The MIC values of 1 are compared with those of some related 2-halcalkylthio penems prepared in this work, and also Sch 29482 and thienamycin.
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ROKURO MASUMA, YOSHITAKE TANAKA, HAJIME TANAKA, SATOSHI OMURA
1986 Volume 39 Issue 11 Pages
1557-1564
Published: 1986
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Nanaomycin production by
Streptanyces rosa subsp.
notoensis in complex media was inhibited by exogenously supplied inorganic phosphate. The inhibition was reversed by phosphate-trapping agents such as allophane and aluminum oxide. Under such condition nanaomycin production increased to the control level, and the phosphate content dropped down to the unsupplemented level. When allophane was added to conventional complex media containing nutrient-derived inorganic phosphate, the production of nanaomycin and several other antibiotics, which are subject to phosphate regulation, was enhanced several fold with the simultaneous reduction of free phosphate. The term "phosphate-depressed fermentation" is proposed for this technique.
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JOSÉ M. LUENGO, JOSÉ L. IRISO, MANUEL J. LÓPEZ-NI ...
1986 Volume 39 Issue 11 Pages
1565-1573
Published: 1986
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The enzyme phenylacetyl-CoA: 6-Aminopenicillanic acid acyltransferase of
Penicillium chrysogenum was evaluated by direct bioassay against
Micrococcus luteus ATCC 9341. The enzyme required dithiothreitol, was inactivated by 0.2 mM Hg2+ (100%), Zn2+ (80%), Cu2+ (60%), 1 mM N-ethylmaleimide (80%), and showed maximal catalytic activity at pH 8.4 and 20°C. The V50 values for phenylacetyl-CoA and 6-aminopenicillanic acid were 0.55 mM and 1 μM, respectively. When octanoyl-CoA was employed as substrate similar results were obtained. In both cases the product generated showed strong antibacterial activity which was quickly lost when incubation was carried out with β-lactamase. Reactions performed in the presence of
Escherichia coli penicillin acylase did not generated active products when phenylacetyl-CoA was the substrate; they did with octanoyl-CoA. Time-course experiments revealed that the highest enzyme levels are found in 36 hours mycelium and remained almost constant from 48 to 96 hours; thereafter the level of the enzyme slowly decreased.
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DAISUKE KOMAGATA, HARUYUKI YAMASHITA, AKIRA ENDO
1986 Volume 39 Issue 11 Pages
1574-1577
Published: 1986
Released on J-STAGE: April 19, 2006
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Approximately 1, 600 fungal strains were tested for ability to convert compactin (ML-236B) to ML-236A and
Emericella unguis IFO 8087 was found to be the most active.
E. unguis converted ML-236B to ML-236A with a yield of over 90%.
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ALFREDO RODRÍGUEZ-TEBAR, DAVID VÁZQUEZ, JOSÉ L. P ...
1986 Volume 39 Issue 11 Pages
1578-1583
Published: 1986
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The thermodynamics of the interaction between the glycopeptide antibiotics vancomycin and ristocetin and bacterial peptidoglycan peptide analogs have been studied by means of a microcalorimetric titration technique. From results of the calorimetric measurements, changes in Gibbs energies, enthalpies, entropies and heat capacities for the binding reactions have been calculated. The derived thermodynamic data have been discussed on the basis of stereochemical data available for the interaction of acetyl-D-alanyl-D-alanine with each of the two antibiotics. The significance of entropic factors connected with conformational changes of the antibiotics is stressed.
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KOZO TOMATSU, SHIGEYUKI ANDO, SHINJI MASUYOSHI, MINORU HIRANO, TAKEO M ...
1986 Volume 39 Issue 11 Pages
1584-1591
Published: 1986
Released on J-STAGE: April 19, 2006
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BMY-28142, 7-[(
Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1-methylpyrrolidinio) methyl-3-cephem-4-carboxylate, exhibited a well-balanced, extended-spectrum of antibacterial activity both
in vitro and
in vivo. Against Staphylococci and Streptococci, BMY-28142 was about four to ten times more active than ceftazidime and comparable to cefotaxime. Most Enterobacteriaceae were more susceptible to BMY-28142 than to ceftazidime, though strains of
Pseudomonas aeruginosa were slightly more sensitive to ceftazidime. BMY-28142 showed potent activity against Gram-negative bacteria resistant to ceftazidime and/or cefotaxime. Bactericidal activity of BMY-28142 against 10 strains of
P. aeruginosa was superior to that of ceftazidime. In bacterial infection models in mice, BMY-28142 was more effective than ceftazidime against three Gram-positive and three Gram-negative pathogens. The anti-pseudomonal
in vivo activity of BMY-28142 was nearly comparable to that of ceftazidime. The blood levels and urinary excretion rates of BMY-28142 in mice were similar to those of ceftazidime.
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AKIRA TSUJI, HIDEKI HIROOKA, IKUMI TAMAI, TETSUYA TERASAKI
1986 Volume 39 Issue 11 Pages
1592-1597
Published: 1986
Released on J-STAGE: April 19, 2006
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Transport of a new cephalosporin developed for oral use, FK089, has been studied with the rat everted small intestine
in vitro. Uptake was found to be pH-dependent with the maximum rate at an acidic pH below 5 and with a 5-fold lower rate at pH 7.0. The shape of the pH-rate profile was very similar to that of cefixime and different from that of pH-lipophilicity profile of FK089. The saturation kinetics of the uptake of FK089 were demonstrated at pH 5.0. By correcting the nonsaturable rate process, the kinetics of the mutual inhibition of FK089 uptake by cefixime and cefixime uptake by FK089 were all consistent with competitive type inhibition. The results indicate that carrier-mediated transport is responsible for transport of cephem antibiotics without an α-amino group in the side chain at the 7-position of the cephem nucleus in the intestinal brush-border membrane.
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S. RENGARAJU, S. NARAYANAN, P. L. GANJU, M. A. AMIN, M. R. S. IYENGAR, ...
1986 Volume 39 Issue 11 Pages
1598-1601
Published: 1986
Released on J-STAGE: April 19, 2006
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KAZUTAKA FUKUSHIMA, KATSUKIYO YAZAWA, TADASHI ARAI
1986 Volume 39 Issue 11 Pages
1602-1604
Published: 1986
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J. FUSKA, D. UHRÍN, B. PROKSA, Z. VOTICKÝ, J. RUPPELDT
1986 Volume 39 Issue 11 Pages
1605-1608
Published: 1986
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AKIRA ENDO, KEIJI HASUMI, AKIRA YAMADA, RIKA SHIMODA, HIROSHI TAKESHIM ...
1986 Volume 39 Issue 11 Pages
1609-1610
Published: 1986
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WILLIAM J. WHEELER, DON R. FINLEY, JOHN L. OTT
1986 Volume 39 Issue 11 Pages
1611-1614
Published: 1986
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KIYOTO EDO, YURIKO AKIYAMA, KUNIHITO SAITO, MICHINAO MIZUGAKI, YOSHIO ...
1986 Volume 39 Issue 11 Pages
1615-1619
Published: 1986
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DONALD R. KIRSCH, MARGARET H. LAI
1986 Volume 39 Issue 11 Pages
1620-1622
Published: 1986
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NOBUYOSHI SHIMADA, SHIGERU HASEGAWA, TAKASHI HARADA, TAKAYUKI TOMISAWA ...
1986 Volume 39 Issue 11 Pages
1623-1625
Published: 1986
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HIKARU NAKAMURA, SHIGERU HASEGAWA, NOBUYOSHI SHIMADA, AKIO FUJII, TOMO ...
1986 Volume 39 Issue 11 Pages
1626-1629
Published: 1986
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KIYOSHI SHIBATA, SADAYOSHI SATSUMABAYASHI, AKIRA NAKAGAWA, SATOSHI OMU ...
1986 Volume 39 Issue 11 Pages
1630-1633
Published: 1986
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KUNIO ISSHIKI, TSUYOSHI TAMAMURA, TSUTOMU SAWA, HIROSHI NAGANAWA, TOMI ...
1986 Volume 39 Issue 11 Pages
1634-1635
Published: 1986
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AKIRA NAKAGAWA, YUZURU IWAI, HIDEKI SHIMIZU, SATOSHI OMURA
1986 Volume 39 Issue 11 Pages
1636-1638
Published: 1986
Released on J-STAGE: April 19, 2006
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