The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 43 , Issue 11
Showing 1-21 articles out of 21 articles from the selected issue
  • E. SELVA, G. BERETTA, R. PALLANZA, B. P. GOLDSTEIN, M. BERTI, D. M. F. ...
    1990 Volume 43 Issue 11 Pages 1349-1358
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Antibiotic SB22484 is a novel member of the aurodox type antibiotic group produced in submerged-fermentation cultures of Streptomyces sp. NRRL 15496.
    The antibiotic complex is composed of two pairs of isomers with MW's of 752 and 766. The individual isomers, which were separated by preparative HPLC, equilibrate to a mixture of the isomer pair when left in aqueous solution.
    In vitro, SB22484 antibiotics strongly inhibited neisseriae and were also active against Streptococci, Ureaplasma urealyticum and Haemophilus influenzae.
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  • PIETRO FERRARI, DUNCAN EDWARDS, GIAN GUALBERTO GALLO, ENRICO SELVA
    1990 Volume 43 Issue 11 Pages 1359-1366
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    SB22484, active against Neisseriae gonorrhoeae and Neisseriae meningitidis, is a complex of four factors, designated 1 through 4, which from two pairs of isomers, 1 and 3, and 2 and 4. Factors 1 and 3 account for 65% of the complex, factor 3 being the predominant one.
    On the basis of the existing and implemented correlations between structure and physico-chemical characteristics (UV and IR spectroscopies, ionization properties, MS as FAB and as negative and positive CI, 1H NMR spectroscopy as 2D COSY and NOESY) in the aurodox field, the complete structures were assigned. Factor 3 can be described as N-[7-[5(R)-[7-[1, 2-dihydro-4-hydroxy-1H-2-oxo-3-pyridinyl]-6-methyl-7-oxo-1(E), 3(E), 5(E)-heptatrienyl]tetrahydro-3(S), 4(R)-dihydroxyfuran-2(S)-yl]-6(S)-methoxy-5, 7(R)-dimethyl-2(E), 4(E)-heptadienyl]-α(S)-methyl-5(S)-methyltetrahydro-2(S), 4(S or R)-dihydroxy-6(S)-[1(E), 3(Z)-pentadienyl]-2H-pyran-2-acetamide. Factor 1 is an epimer of factor 3 with the opposite configuration at the anomeric center. Factors 2 and 4 have an ethyl group instead of the methyl group a to the acetamide moiety and are in the same stereochemical relationship as the pair 1 and 3.
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  • YOSUKE SAWADA, TAKASHI TSUNO, HARUAKI YAMAMOTO, MAKI NISHIO, MASATAKA ...
    1990 Volume 43 Issue 11 Pages 1367-1374
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Four blocked mutants which accumulated new dihydrobenzo[a]naphthacenequinone metabolites, designated pradimicins M, N, O and P, have been isolated from cultures of mutants of Actinomadura hibisca P157-2 resulting from treatment with N-methyl-N'-nitro-N-nitrosoguanidine. The structures of the four compounds were determined by spectral analysis. Pradimicins N, O and P contain D-alanine, while pradimicin M does not. The conformations at C-5 and C-6 of these compounds are different from those of the original pradimicins.
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  • J. G. ONDEYKA, R. T. GOEGELMAN, J. M. SCHAEFFER, L. KELEMEN, L. ZITANO
    1990 Volume 43 Issue 11 Pages 1375-1379
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Paraherquamide and six novel analogs were isolated from the fermentation of Penicillium charlesii (ATCC 20841). All seven natural products displayed potent antinematodal activity against Caenorhabditis elegans. None of the novel analogs were more potent than paraherquamide
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  • J. M. LIESCH, C. F. WICHMANN
    1990 Volume 43 Issue 11 Pages 1380-1386
    Published: November 25, 1990
    Released: April 19, 2006
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    Paraherquamides B (2, C27H33N3O4), C (3, C28H33N3O4), D (4, C28H33N3O5), E (5, C28H35N3O4), F (6, C28H35N3O3), and G (7, C28H35N3O4) are novel metabolites of Penicillium charlesii. The structures of these compounds have been determined by NMR and MS analysis.
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  • RAYMOND J. ASHTON, MARTIN D. KENIG, KONG LUK, DONALD N. PLANTEROSE, GI ...
    1990 Volume 43 Issue 11 Pages 1387-1393
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Six strains of Actinomadura pelletieri were shown to produce a novel macrolide antibiotic, designated MM 46115. MM 46115 was active against parainfluenza virus 1 and 2 and Grampositive bacteria. Methods are described for the production of MM 46115 by strain IP 729.63, and for the isolation of the compound from a butanol extract of the culture filtrate.
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  • OSAMU NAKAYAMA, MASASHI YAGI, MIHO TANAKA, SUMIO KIYOTO, ITSUO UCHIDA, ...
    1990 Volume 43 Issue 11 Pages 1394-1402
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    WS-7528, produced by Streptomyces sp. No. 7528, was extracted from cultured broth, purified by solvent extraction followed by chromatography on silica gel and then isolated as pale yellow powder (C16H14O5, mp 95-98°C). WS-7528 inhibited estrogen binding to its receptor protein in rat uterine cytosol. The IC50 value of WS-7528 for partially purified rat uterine cytosol receptor was 5.7×10-8M.
    This compound was found to induce the growth of the estrogen dependent cell line MCF-7.
    WS-7528 was tested orally and subcutaneously in immature rats to confirm its effect on the growth of the uterus.
    WS-7528 has also weak anti-inflammatory activity on the carrageenin paw edema of the rat model.
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  • ANDREAS FREDENHAGEN, GABRIELE FENDRICH, FRITZ MÄRKI, WALTER M&Aum ...
    1990 Volume 43 Issue 11 Pages 1403-1412
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Duramycins B and C, two new lanthionine containing antibiotics, have been isolated from Streptoverticillium strain R2075 and Streptomyces griseoluteus (R2107). The known antibiotics duramycin and cinnamycin were reisolated from Streptoverticillium hachijoense (DSM 40114) and Streptomyces longisporoflavus (DSM 40165). The structures of these latter two compounds should be revised by changing ammo acid residue 3 to glutamine and 17 to asparagine, respectively.
    Cinnamycin therefore seems to be identical to Ro 09-0198. Leucopeptin has been shown to be identical to duramycin. Physico-chemical data of these compounds provide evidence for a similar structure for all duramycin antibiotics. All compounds of this group inhibit human phospholipase A2 at a concentration of 10-6 molar.
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  • DOROTHÉE KUHNT, TIMM ANKE, HELMUT BESL, MONIKA BROSS, RUPERT HE ...
    1990 Volume 43 Issue 11 Pages 1413-1420
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Three new inhibitors of cholesterol biosynthesis have been isolated from cultures of Xerula melanotricha and their structures elucidated by spectroscopic methods. Dihydroxerulin (1) in admixture with xerulin (2) strongly inhibits the incorporation of 14C- acetate into cholesterol in HeLa cells while the incorporation of 14C-mevalonate is not affected. Xerulinic acid (3) shows similar biological activities but a higher cytotoxicity.
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  • FUMIAKI HAYASHI, KAZUO NAGASHIMA, YOSHIHIRO TERUI, YOSHIMI KAWAMURA, K ...
    1990 Volume 43 Issue 11 Pages 1421-1430
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    PA48009, a lanthionine-containing peptide antibiotic was isolated from the culture broth of Streptoverticillium griseoverticillatum PA-48009, and identified as duramycin. Determination of the structure using both Edman degradations and 2D NMR spectroscopy showed the need to revise the structure of duramycin given in literature. Duramycin (PA48009) was different from lanthiopeptin (Ro 09-0198, cinnamycin) only by a Lys/Arg exchange at position 2.
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  • PETER HAMMANN, GERHARD KRETZSCHMAR, GERHARD SEIBERT
    1990 Volume 43 Issue 11 Pages 1431-1440
    Published: November 25, 1990
    Released: April 19, 2006
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    The synthesis and the biological activity of 34 acyl derivatives of elaiophylin (1) and 6 deglycosidation products were described. Especially the unsymmetric deglycosidation products 33, 38 and 40 and dimethyloctahydroelaiophylin (21) exhibited an activity against nematodes.
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  • MASAYUKI MURAKAMI, TSUTOMU AOKI, MUNENORI MATSUURA, WATARU NAGATA
    1990 Volume 43 Issue 11 Pages 1441-1449
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Several 2-substituted oxapenems, la, 1b and 1c, bearing the hydroxyethyl side-chain at 6α were synthesized in a highly stereoselective manner starting from the commercially available 3α-hydroxyethyl-4β-acetoxyazetidinone (5). The stability, in vitro antibacterial activity, and β-lactamase inhibitory properties of these oxapenems were examined. The 2-isopropyl penem 1c had considerable stability as shown by its t1/2 of 200 minutes in pH 7.0 buffer solution and at 37°C, while the other two la and 1b were labile. Interestingly, the antibacterial activity of these compounds paralleled their stability and thus penem 1c showed appreciable MICs, whereas the other two were virtually inactive. All three penems inhibited certain cephalosporinases strongly, but penicillinases only weakly. Thus, the inhibitory spectrum was similar to that for epi-thienamycin B and not the spectrum for clavulanic acid.
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  • KATSUYOSHI IWAMATSU, KUNIO ATSUMI, KENJI SAKAGAMI, HIROKO OGINO, TAKAS ...
    1990 Volume 43 Issue 11 Pages 1450-1463
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The synthesis and biological activity of a series of 3-[2-(5-hydroxy-4-pyridon-2-yl)ethenyl]cephalosporin derivatives are described. They showed very potent activity against Gram-negative bacteria, especially Pseudomonas Aeruginosa. (6R, 7R)-7-[(Z]-2-(2-Aminothiazol-4-yl)-2-(l-carboxy-l-methyl)-ethoxyiminoacetamido]-3-[(Z]-2-(l, 5-dihydroxy-4-pyridon-2-yl)ethenyl]ceph-3-em-4-carboxylic acid, CP6162 (8e), was selected for further evaluation as an antipseudomonal chemotherapeutic agent.
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  • KEIICHI AJITO, DAISHIRO IKEDA, CHISATO NOSAKA, KEIKO KOMURO, SHINICHI ...
    1990 Volume 43 Issue 11 Pages 1464-1470
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The preparation and antitumor effects of 3'-deamino-3'-morpholino derivatives of pirarubicin are described. Di-N-alkylation of pirarubicin with bis(2-iodoethyl)ether gave 3'-morpholino-pirarubicin, which was converted into its 13-tosylhydrazone, 13-deoxy derivative and 13-(S)- and 13-(R)-dihydro derivatives. Intraperitoneal administration to murine tumors indicated that the effective dose ranges of the compounds having sp3 carbon at C-13 position were broader than those of the compounds having sp2 carbon. By oral administration, 13-(S)-dihydro isomer was more effective than 13-(R)-dihydro isomer.
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  • ALDO TRANI, ADRIANO MALABARBA, PIETRO FERRARI, ROSETTA PALLANZA, MARIS ...
    1990 Volume 43 Issue 11 Pages 1471-1482
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The condensation of the terminal carboxyl group of the deglucoteicoplanin (TD) with various substituted hydrazines produced hydrazide derivatives having different physico-chemical properties. This chemical modification of the carboxyl function does not affect the ability of teicoplanin antibiotics to interfere in bacterial cell-wall synthesis.
    The antibacterial activity of deglucoteicoplanin hydrazides (V) were found to depend mostly on their ionic character. All the hydrazides were slightly more active than TD on Escherichia coli. Those possessing an additional basic group were more in vitro active than TD against Gram-negative microorganisms. In Experimental Streptococcus pyogenes septicemia in the mouse, basic hydrazides were more active than other derivatives when administered subcutaneously although they are as potent as TD.
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  • HIROAKI URABE, KEITARO TOYAMA, HIROSHI OGAWARA
    1990 Volume 43 Issue 11 Pages 1483-1488
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A β-lactamase gene was cloned from Streptomyces cellulosae as a 2.3-kb DNA fragment using Streptomyces lividans 1326 and PIJ385 as a host-vector system. During the course of cloning, a part of the chromosomal DNA fragment cloned together with a part of the vector plasmid were deleted, indicating instability of this contiguous DNA region. The enzyme from the clone showed similar properties with respect to binding of blue dextran and isoelectric point to the enzyme from S. cellulosate. The cloned gene hybridized not only to DNA of S. cellulosae, the source of DNA, but also to DNAs of several Streptomyces species, irrespective of their formation of β-lactamase. These results suggest that this gene may have homology to genes other than the one for β-lactamase.
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  • KAYOKO SUZUKAKE-TSUCHIYA, YUKARI MORIYA, KATSUHISA YAMAZAKI, MAKOTO HO ...
    1990 Volume 43 Issue 11 Pages 1489-1496
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    During the course of in vitro screening of agents which are preferentially active against ras oncogene-expressed cells, a new anthracycline (identified as 2-demethylsteffimycin D) and a heptaene (possibly a new member of partricins) were isolated from microbial fermentation broths. Among known compounds tested, 5-fluorouracil, 5-fluorodeoxyuridine and oxanosine showed high selectivity towards ras oncogene-expressed cells.
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  • MOHINDAR S. PUAR, DORIS SCHUMACHER
    1990 Volume 43 Issue 11 Pages 1497-1501
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • BRUCE B. JARVIS, CATHERINE A. ARMSTRONG, MING ZENG
    1990 Volume 43 Issue 11 Pages 1502-1504
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • HIROYUKI KUMAGAI, TOHRU MASUDA, MICHIYO OHSONO, SEIKO HATTORI, HIROSHI ...
    1990 Volume 43 Issue 11 Pages 1505-1507
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • HIDEAKI SUZUKI, SATOSHI TAKENAKA, KENJI KINOSHITA, TOSHIRO MOROHOSHI
    1990 Volume 43 Issue 11 Pages 1508-1511
    Published: November 25, 1990
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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