The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 40 , Issue 6
Showing 1-23 articles out of 23 articles from the selected issue
  • I. FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES OF THE ANTIBIOTIC
    MICHIO ICHIMURA, TOSHIRO KOGUCHI, TOHRU YASUZAWA, FUSAO TOMITA
    1987 Volume 40 Issue 6 Pages 723-726
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A new antibiotic, CV-1, was isolated from the culture broth of a Streptomyces sp. by various chromatographies. CV-1 showed antibacterial activity against Escherichia coli in cooperation with spiramycin, a macrolide antibiotic. The mode of action of CV-1 seemed to be the inhibition of lipopolysaccharide synthesis.
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  • II. STRUCTURE DETERMINATION
    TOHRU YASUZAWA, MAYUMI YOSHIDA, MICHIO ICHIMURA, KUNIKATSU SHIRAHATA, ...
    1987 Volume 40 Issue 6 Pages 727-731
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The structure of a new antibiotic, CV-1 was determined to be 1, 2-diamino-1, 2-N, N'-carbonyl-1, 2-dideoxy-α-D-glucose hydrate by spectral and chemical studies. CV-1 possessed a unique open ring hemiaminal structure. CV-1 synthesized from N-car bamoyl-D-glucosamine was identical to material isolated from fermentation.
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  • I. TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
    TAKASHI SHOMURA, SHUICHI GOMI, MITSUGU ITO, JUNKO YOSHIDA, ERIKO TANAK ...
    1987 Volume 40 Issue 6 Pages 732-739
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A new species of Streptomyces is described for which the name Streptomyces aculeolatus is proposed. The organism produces new antibiotics SF2415A1, A2, A3, Bl, B2 and B3 active against Gram-positive bacteria. Empirical molecular formulae of the antibiotics SF2415A1, A2, A3, Bl, B2 and B3 were determined to be C26H31N2O5Cl, C26H30N2O5, C26H30N2O5Cl2, C26H33O5Cl, C26H32O5 and C26H32O5C12, respectively.
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  • II. THE STRUCTURAL ELUCIDATION
    SHUICHI GOMI, SHOKICHI OHUCHI, TORU SASAKI, JIRO ITOH, MASAJI SEZAKI
    1987 Volume 40 Issue 6 Pages 740-749
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Structures of new antibiotics SF2415A1, A2, A3, Bl, B2 and B3 were deduced from spectroscopic analyses and degradation studies. The structure of SF2415A3, which has the most antibacterial activity, was proposed to be 3, 4a-dichloro-9-diazo-3, 4, 4a, 10a-tetrahydro-6-hydroxy-2, 2, 7-trimethyl-10a-[(E)-3, 7-dimethyl-2, 6-octadienyl]-(2H, 9H)naphtho[2, 3-b]pyran-5, 8, 10-trione. All of antibiotics SF2415 have a semi-naphthoquinone structure.
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  • A. D. ARGOUDELIS, L. BACZYNSKYJ, M. T. Kuo, A. L. LABORDE, O. K. SEBEK ...
    1987 Volume 40 Issue 6 Pages 750-760
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Arginomycin is a new nucleoside antibiotic produced by Streptomyces arginensis. Arginomycin, C18H28N8O5, which inhibits the growth of Gram-positive bacteria and fungi in vitro, is structurally related to blasticidin S and found to be relatively non-toxic.
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  • M. DEBONO, M. BARNHART, C. B. CARRELL, J. A. HOFFMANN, J. L. OCCOLOWIT ...
    1987 Volume 40 Issue 6 Pages 761-777
    Published: June 25, 1987
    Released: April 19, 2006
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    A21978C, produced by Streptomyces roseosporus, NRRL 11379, is a complex of new acidic lipopeptolide antibiotics which inhibits Gram-positive bacteria. HPLC separation of the various components from the purified complex resulted in the isolation of A21978C1, -C2 and -C3 (major components) and -C4, -C5 and -C0 (minor components). Each of these components was fermented with cultures of Actinoplanes utahensis (NRRL 12052) to give the identical inactive peptide ("A21978C nucleus") by removal of the fatty acid acyl groups from the TV-terminus. This peptide was composed of 13 amino acids: L-kynurenine, L-threo-3-methylglutamic acid, L-asparagine, L-aspartic acid (3 residues), glycine (2 residues), L-tryptophan, L-ornithine, D-alanine, o-serine and L-threonine. The amino acid sequence was determined using a combination of the Edman degradation and gas chromatography mass spectrum (GC-MS) analysis of appropriately derivatized peptides obtained from partial hydrolysis. Each major component was shown to be acylated with a branched chain fatty acid at the N-terminus and the structure of this fatty acid was determined by 1H NMR and mass spectral methods. A structure for A21978C was assigned on the basis of this degradative and physico-chemical information.
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  • KOHTAROU FUNAISHI, KENJI KAWAMURA, YASUYUKI SUGIURA, NORIYUKI NAKAHORI ...
    1987 Volume 40 Issue 6 Pages 778-785
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A novel antibiotic, kazusamycin B (C32H46O7, MW 542), was isolated from the fermentation broth of Streptomyces sp. No. 81-484 and the structure was established mainly on the basis of its physico-chemical properties. Unambiguous 13C NMR spectral analysis of kazusamycin B has been also accomplished. Kazusamycin B possesses potent cytocidal activities against L1210 (IC50 0.0018 μg/ml) and P388 (IC100 0.0016 μg/ml) leukemia cells in vitro.
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  • RENUKA MIOSRA, RAMESH C. PANDEY, BRUCE D. HILTON, PETER P. ROLLER, JAM ...
    1987 Volume 40 Issue 6 Pages 786-802
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    IR, UV-visible spectroscopy, circular dichroism, 1H and 13C NMR studies, high resolution electron impact, field desorption, and fast atom bombardment mass spectral studies are reported for fredericamycin A (NSC-305263), a novel antitumor antibiotic of acid-base indicator type produced by Streptomyces griseus (FCRC-48). The spectral data are correlated with the structure obtained by X-ray crystallography as (E, E)-6', 7'-dihydro-4, 9, 9'tr ihydroxy-6-methoxy- 3'-(1, 3-pentadienyl)-spiro-[2H-benz[f] indene-2, 8'-[8H]-cyclopent-[g]isoquinoline]-l, 1', 3, 5, 8(2'H)-pentone. The novel spiro ring antibiotic exhibits unusual 1H and 13C NMR spectroscopic and chemical behavior, not previously observed in other antibiotic structures.
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  • YUHPYNG L. CHEN, Cnm-Wu CHANG, KIRK HEDBERG, KAREN GUARINO, WILLARD M. ...
    1987 Volume 40 Issue 6 Pages 803-822
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    6-(Heterocyclyl)methylene penam sulfones (1) are effective β-lactamase inhibitors and potent ampicillin and cefazolin potentiators against both Gram-positive and Gram-negative β-lactamase producing bacteria. Several of these analogs having a π-deficient 2-heteroaryl substituent attached to the C6-methylene position showed better inhibitory activity than elavulanic acid, Ro 15-1903, 6β-bromopenicillanic acid, and sulbactam against a variety of β-lactamases. The compounds were devoid of any antibacterial activity, but in combination with ampicillin or cefazolin, exhibited synergistic activity at least equal to elavulanic acid, Ro 15-1903, 6β-bromopenicillanic acid or sulbactam against β-lactamase producing strains. Structure-activity relationships for a number of compounds are described. The structureactivity relationships can be rationalized by an enzyme inhibition mechanism which we have previously proposed on the basis of methanolysis of 6-(2-pyridyl)methylene penam sulfone (1a). Two synthetic routes to prepare compounds of structural type 1 via either a Wittig reaction or an aldol condensation are reported. β-Lactamase inhibition and MIC data are presented.
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  • H. A. KIRST, J. E. TOTH, J. A. WIND, M. DEBONO, K. E. WILLARD, R. M. M ...
    1987 Volume 40 Issue 6 Pages 823-842
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A large series of C-23-modified derivatives of 5-O-mycaminosyltylonolide were synthesized, in which the C-23 hydroxyl group was replaced by halo, aryl ether or thioether, azido, amino or dialkylamino substituents via SN2 displacement reactions. The majority of derivatives possessed excellent in vitro activity against a variety of aerobic and anaerobic bacteria. While some of the compounds treated experimental infections in rodents by parenteral administration, none showed any significant efficacy or bioavailability after oral dosing. Novel rearrangement products were obtained from some of the reactions; these were identified as 13, 23-cyclopropyl-12, 22-exomethylene and 13, 23-cyclopropyl-12-alkoxy derivatives.
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  • V. SYNTHESIS AND IN VITRO ANTIVIRAL ACTIVITY OF NEW AMINOGLYCOSIDE DERIVATIVES HAVING PALMITOYL GROUP
    KEIJI MATSUDA, NOBUYOSHI YASUDA, HIDEO TSUTSUMI, TAKAO TAKAYA
    1987 Volume 40 Issue 6 Pages 843-854
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The synthesis and antiviral activity of various aminoglycoside derivatives having a palmitoyl group are described. All of these aminoglycoside derivatives exhibited almost the same excellent antiviral activity against herpes simplex virus type I and influenza virus.
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  • URSULA DEGWERT, ROSEMARIE VAN HÜLST, HERMANN PAPE, RICHARD E. HER ...
    1987 Volume 40 Issue 6 Pages 855-861
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Feeding experiments with Actinoplanes sp. SN223/29 showed that 3-amino-5-hydroxy[7-]SP13C]benzoic acid is not incorporated into acarbose (I). The valienamine moiety of I is thus not derived in the same way, from the shikimate pathway, as the m-C7N units in the ansamycin, mitomycin and ansamitocin antibiotics. Feeding experiments with [U-13C3]glycerol followed by analysis of I by multiple quantum NMR spectroscopy support this conclusion and point to formation of the valienamine moiety by cyclization of a heptulose phosphate which arises from a triose phosphate via successive transfer of two 2-carbon fragments by transketolase, as proposed by PAPE and co-workers.
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  • MAN WAH YUNG, COLIN GREENT
    1987 Volume 40 Issue 6 Pages 862-867
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    It has been suggested that the aminoglycoside drugs are ototoxic because they contain amine groups that interact with membrane phospholipids. The interaction of kanamycin A and kanamycin B with vesicles containing various phospholipids was assessed from studies of vesicle aggregation and of the fluorescence of the probes l-anilino-8-naphthalene sulfonic acid (ANS) and l, 6-diphenyl-l, 3, 5-hexatriene (DPH) added to the system.
    Kanamycin B, with 5 amino groups, showed a stronger interaction with the acidic phospholipids than kanamycin A, with only 4 amino groups. The evidence indicated that the interaction was an ionic one involving the charged groups of both components with penetration of the hydrocarbon interior of the bilayers. Of all the phospholipids tested polyphosphoinositide showed the greatest ability to interact with the kanamycins, supporting the proposal that interaction with this phospholipid may be the basis of the ototoxicity of aminoglycosides.
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  • JUNICHI MITSUYAMA, MASAHIRO TAKAHATA, TAKASHI YASUDA, ISAMU SAIKAWA
    1987 Volume 40 Issue 6 Pages 868-872
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The relationship between the chemical structure and the mode of action of piperacillinanalogues (PIPC-analogues) against Escherichia coli and Klebsiella pneumoniae were investigated. The antibacterial activity of PIPC-analogues increased with an increase in the number of carbon atoms at the N-4 position of 2, 3-dioxopiperazine. Their mode of action is discussed on the basis of the results of studies on outer membrane permeability, stability to β-lactamase and binding affinity to penicillin-binding proteins (PBPs). The outer membrane permeability and stability to β-lactamase were hardly affected by the chain length of the alkyl group at the N-4 position. On the other hand, the affinity to PBPs, especially to PBP 3, became stronger with increase of the number of carbon atoms at N-4 position. These results suggest that increased affinity to PBPs is the main reason for the increased antibacterial activity of the PIPC-analogues reported here.
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  • ERIC W. FISHER, CHARLES J. DECEDUE, BRADLEY T. KELLER, RONALD T. BORCH ...
    1987 Volume 40 Issue 6 Pages 873-881
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Neplanocin A, a cyclopentenyl analog of adenosine, is a naturally occurring antibiotic possessing potent inhibitory activity toward the enzyme S-adenosylhomocysteine (AdoHcy) hydrolase. In the present study, we examined whether there was a correlation between the inhibition of prokaryotic AdoHcy hydrolase and the reported antibacterial activity of neplanocin A, e.g. Alcaligenes faecalis (YAGINUMA et al., J. Antibiotics 34: 359-366, 1981). Of 16 bacterial species screened, only 2 organisms (both of which contained AdoHcy hydrolase) were sensitive to 10 nM neplanocin A when grown on agar plates. None of the 16 strains showed any growth sensitivity in broth culture to concentrations of the antibiotic as high as 4 mM. However, treatment of A. faecalis in broth culture with 14 μM neplanocin A resulted in complete inhibition of cellular AdoHcy hydrolase and subsequent elevation of intracellular AdoHcy. No alternative method for degrading or removing the excess AdoHcy from these cells was detected. Bacillus subtilis, which exhibited no AdoHcy hydrolase activity showed no alteration of AdoHcy metabolism when treated with the same concentration of the antibiotic. These results indicate that inhibition of AdoHcy hydrolase is not related to the antibacterial activity of neplanocin A and suggest that using this enzyme as a target for the design of antimicrobial agents is not likely to prove a productive approach.
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  • PETRI VILJANEN
    1987 Volume 40 Issue 6 Pages 882-886
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Outer membrane disorganizing polycation, polymyxin B nonapeptide (PMBN), reduced drastically the production of recombinants when present at sub-MIC concentrations during F'-mediated Escherichia coll conjugation. The decrease of recombinants was accompanied by a less marked decrease of viability in the recipient population in a manner resembling lethal zygosis. No reduction was seen when either donor or recipient was grown in the same PMBN concentration, washed and resuspended to PMBN-free medium before mating. The same concentration of outer membrane disorganizing polycations of higher bactericidal activity (protamine and polylysine) caused only a moderate reduction in transconjugant frequency when present during mating. Spermine and tetralysine, which are not effective disorganizers of the outer membrane, did not reduce the recombinant frequency or the viability of the recipients.
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  • ROBERT S. WEHBIE, CAI RUNSHENG, HENRY A. LARDY
    1987 Volume 40 Issue 6 Pages 887-893
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    We have examined the ion transport properties and the inhibition of rat liver mitochondrial substrate oxidation by the antibiotic W341C. W341C was able to transport 22Na+ and 42K+ across a bulk carbon tetrachloride layer. A preference was shown for K+ transport. With equal molar antibiotic concentrations, W341C transported 42K+ at a greater rate than the K+-selective ionophore nigericin, but transported 22Na+ at a lesser rate than the Na+-selective ionophore monensin. Like nigericin, W341C was able to deplete mitochondrial K+, but not Mg2+ nor Ca2+. The inhibition of mitochondrial substrate oxidation by W341C paralleled the patterns obtained with nigericin. These data indicate that W341C is a K+selective ionophore that inhibits mitochondrial substrate oxidation by a mechanism analogous to that of nigericin.
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  • KYUICHI NEMOTO, FUMINORI ABE, KEIKO KARAKAWA, HIROO HORINISHI, HAMAO U ...
    1987 Volume 40 Issue 6 Pages 894-898
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Ubenimex enhanced colony formation of bone marrow cells from CDF1 mice induced by L929 cell supernatant, which shows a macrophage-colony-stimulating activity (M-CSA), and also enhanced the colony formation induced CDF1 mouse spleen cell conditioned medium, which shows a granulocyte and macrophage-colony-stimulating activity. The maximal effect was obtained at 0.01 μg/ml. But, ubenimex showed no effect on the nature of the colonies induced by each CSA. By preincubation of the bone marrow cells with ubenimex, M-CSA-induced colony-forming and the M-CSA-binding activities of the cells were increased. These results suggest that ubenimex enhances the CSA-induced colony formation of bone marrow progenitor cells of CDF1 mouse by increasing the amount of the CSA-binding to the cells.
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  • HIKARU NAKAMURA, KAZURO SHIOMI, HIRONOBU IINUMA, HIROSHI NAGANAWA, TAM ...
    1987 Volume 40 Issue 6 Pages 899-903
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • MITSUAKI MORIGUCHI, YOSHIFUMI KARA, SHIN-ICHI HATANAKA
    1987 Volume 40 Issue 6 Pages 904-906
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • XING-CHUN CHENG, TSUYOSHI KIHARA, HIROO KUSAKABE, JUNJI MAGAE, YUMIKO ...
    1987 Volume 40 Issue 6 Pages 907-909
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • KUNIAKI TATSUTA, YOSHIYUKI KOBAYASHI, MITSUHIRO KINOSHITA
    1987 Volume 40 Issue 6 Pages 910-912
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • HARUYASU KINASHI, MIYUKI SHIMAJI
    1987 Volume 40 Issue 6 Pages 913-916
    Published: June 25, 1987
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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