The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 39, Issue 3
Displaying 1-23 of 23 articles from this issue
  • VINCENT L. REYNOLDS, J. PATRICK MCGOVREN, LAURENCE H. HURLEY
    1986 Volume 39 Issue 3 Pages 319-334
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
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  • I. TAXONOMY OF THE PRODUCING STRAIN, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL CHARACTERIZATION AND ANTIMICROBIAL PROPERTIES
    RICHARD A. NELSON, JOSEPH A. POPE Jr., GEORGE M. LUEDEMANN, LLOYD E. M ...
    1986 Volume 39 Issue 3 Pages 335-344
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    A microorganism, designated as RV-79-9-101 and now identified as Micromonospora purpureochromogenes subsp. halotolerans, isolated from a mud sample in the Philippines, has been shown to produce a complex of antibiotics called crisamicins. Thin-layer chromatography and bioautography, employing solvent extracts of whole fermentation broths, revealed a minimum of five antimicrobial components. The major biologically-active component
    of the antibiotic complex, crisamicin A, was obtained in pure form after preparative silica gel column chromatography followed by crystallization. Based on physico-chemical data crisamicin A has been identified as a novel member of the isochromanequinone group of antibiotics. It exhibits excellent in vitro activity against Gram-positive bacteria but little or no activity towards Gram-negative bacteria or fungi.
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  • DAKUI LING, LOIS S. SHIELD, KENNETH L. RINEHART Jr.
    1986 Volume 39 Issue 3 Pages 345-353
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    A new antibiotic, crisamicin A, with in vitro activity against Gram-positive bacteria, B16 murine melanoma cells, and herpes simplex, vaccinia, and vesicular stomatitis viruses, has been isolated from Micromonospora purpureochromogenes subsp. halotolerans. On the basis of 1H and 13C NMR spectroscopic, high resolution field desorption mass spectrometric, and circular dichroism studies of the antibiotic and several of its derivatives, the structure of crisamicin A has been assigned.
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  • HIROSHI KASE, HIRONORI FUJITA, JOJI NAKAMURA, KAZUKO HASHIZUME, JOJI G ...
    1986 Volume 39 Issue 3 Pages 354-363
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    Streptomyces gabonae KY2234 was found to produce a new compound, MY336-a, which bound to β-adrenergic receptor. The compound was isolated from the fermentation broth of KY2234. MY336-a showed a high affinity for the β-receptor, labeled with [3H]dihydroalprenolol in the membrane fractions of rat heart (β1-adrenergic receptor) or lung (β2-adrenergic receptor), whereas the compound bound very weakly to α-adrenergic receptor, labeled with [3H]dihydroergokryptine in rat brain. The inhibition constants (Ki) of the compound were 0.73 and 0.14 μM for the β-receptors of heart and lung, respectively. 5'-Guanylylimidodiphosphate (Gpp(NH)p) did not alter the affinity of the β-receptors for MY336-a. In isolated guinea-pig atria, MY336-a produced an inhibition of the positive chronotropic and inotropic effects of isoproterenol. MY336-a also antagonized the relaxation of tone induced by isoproterenol in isolated guinea-pig trachea. No partial agonistic activity was detected in MY336-a in the isolated atria and trachea. In anaesthetized dogs, MY336-a (1 mg/kg, iv) exerted negative inotropic action (left ventricular dp/dt max, -32.6%).
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  • CONVERTING ENZYME PRODUCED BY ACTINOMADURA SPICULOSOSPORA
    TOSHIRO KOGUCHI, KOJI YAMADA, MASAYUKI YAMATO, RYO OKACHI, KIYOSHI NAK ...
    1986 Volume 39 Issue 3 Pages 364-371
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    A novel inhibitor of angiotensin I converting enzyme (ACE), named K-4, was isolated from the culture broth of Actinomadura spiculosospora nov. sp. K-4. The K-4 was an oligopeptide containing L-phenylalanine with (R)-1-amino-2-(4-hydroxyphenyl)ethylphosphonic acid as the C-terminal residue. The compound proved to be a specific and reversible inhibitor of ACE with the inhibition constant (Ki) of 0.18μM, and inhibited ACE non-competitively by use of hippuryl-L-histidyl-L-leucine (HHL) as a substrate. When administrated intravenously to rats, K-4 inhibited the pressor response to angiotensin I.
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  • JERAULD S. SKOTNICKI, BRUCE A. STEINBAUGH
    1986 Volume 39 Issue 3 Pages 372-379
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The synthesis and in vitro antibacterial profile of a series of (Z)-(2-amino-4-thiazolyl)-[(2, 3-dialkoxypropoxy)imino]acetyl derivatives of 7-aminocephalosporanic acid and 3-aminomonobactamic acid are reported.
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  • JERAULD S. SKOTNICKI, DONALD P. STRIKE
    1986 Volume 39 Issue 3 Pages 380-383
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The synthesis of C-3' isothiazolyl and related cephalosporins is presented. The compounds exhibit activity against a variety of Gram-positive and Gram-negative organisms.
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  • XI. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF NEW 3-(2, 2-DIHALOVINYL)CEPHALOSPORINS
    KOHJI KAWABATA, TAKASHI MASUGI, TAKAO TAKAYA
    1986 Volume 39 Issue 3 Pages 384-393
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The synthesis and in vitro antibacterial activity of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-carboxymethoxyiminoacetamido]-3-(2, 2-dihalovinyl)cephalosporins (1) are described. 3-(2, 2-Dihalovinyl)cephalosporins (1c and 1d) exhibited excellent antimicrobial activity against both Gram-positive and Gram-negative bacteria, especially showed higher activity against Staphylococcus aureus than the corresponding 3-vinylcephalosporin (1a; FK027).
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  • XII. SYNTHESIS AND ACTIVITY OF NEW 3-ETHYNYLCEPHALOSPORIN
    KOHJI KAWABATA, TAKASHI MASUGI, TAKAO TAKAYA
    1986 Volume 39 Issue 3 Pages 394-403
    Published: 1986
    Released on J-STAGE: April 19, 2006
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    The synthesis of the orally absorbed 3-ethynylcephalosporin (1b) is described. In addition, the structure-activity relationships and oral absorption in rats of 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-carboxymethoxyiminoacetamido]cephalosporins (1) having various aliphatic hydrocarbon groups at the 3-position are discussed. Of these cephalosporins (1), 3-ethynylcephalosporin (1b) exhibited better activity against Staphylococcus aureus than the other cephalosporins (1a, 1c and 1d) and showed moderate oral absorption in rats.
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  • XIII. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 7β-[(Z)-2-ARYL-2-CARBOXYMETHOXYIMINOACETAMIDO]- 3-VINYLCEPHALOSPORINS
    KOHJI KAWABATA, HIDEAKI YAMANAKA, HISASHI TAKASUGI, TAKAO TAKAYA
    1986 Volume 39 Issue 3 Pages 404-414
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The synthesis, antibacterial activity and oral absorption of the 7β-[(Z)-2-aryl-2-carboxymethoxyiminoacetamido]-3-vinylcephalosporins (1) are described. Of these cephalosporin derivatives (1), 7β-[(Z)-2-(2-amino-4-thiazolyl)-2-carboxymethoxyiminoacetamido]-3-vinylcephalosporin (1a; FK027) exhibited the highest activity against Gram-negative bacteria and showed also good excretion after oral administration to rats. In addition, the effects on the antibacterial activity and oral absorption of the amino function on the thiazole ring are discussed.
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  • SYNTHESIS AND IN VIVO ANTITUMOR ACTIVITIES OF HALOGENATED AND OTHER RELATED DERIVATIVES OF HERBIMYCIN A
    KIYOSHI SHIBATA, SADAYOSHI SATSUMABAYASHI, HIROSHI SANO, KANKI KOMIYAM ...
    1986 Volume 39 Issue 3 Pages 415-423
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    Several halogenated and other related derivatives of herbimycin A have been synthesized and evaluated in vivo for their activities against Ehrlich ascites carcinoma. Some of these derivatives show higher activities than herbimycin A. Among them the derivatives modified at the 4, 5, 6, and 7-positions of the ansa chain showed particularly high activities.
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  • VIII. ABSOLUTE STRUCTURES OF RHIZOXIN AND A RELATED COMPOUND
    SHIGEO IWASAKI, MICHIO NAMIKOSHI, HISAYOSHI KOBAYASHI, JUN FURUKAWA, S ...
    1986 Volume 39 Issue 3 Pages 424-429
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The absolute structure of rhizoxin (1), a potent antifungal and antitumor antibiotic, was determined by interrelation with compound 2 whose structure was established by X-ray analysis. Since a 18OH group was introduced at C-3 on a hydrolytic cleavage of C-2, C-3 epoxy group with alkaline H218O, the original epoxy oxygen should be retained at C-2. The stereo-chemistry at C-2 and C-3 positions in rhizoxin was, therefore, determined as 2R, 3S.
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  • MING LI, YONG-LE CHEN
    1986 Volume 39 Issue 3 Pages 430-436
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    Antitumor antibiotics rhodilunancins A and B were isolated from a culture of Streptomyces violaceus var. lunanensis var. n. No. 1289 by acidic acetone extraction of mycelia and purified by silica gel chromatography. Rhodilunancin A is identical to cosmomycin A. Rhodilunancin B is identical to cosmomycin B (=rhodomycin Y). Both antibiotics exhibited activities against Gram-positive bacteria and inhibition on DNA synthesis of P388 leukemia cell in vitro.
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  • C. A. CLARIDGE, J. A. BUSH, T. W. DOYLE, D. E. NETTLETON, J. E. MOSELE ...
    1986 Volume 39 Issue 3 Pages 437-446
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    When the normal fermentation medium for the production of mitomycin C with Streptomyces caespitosus is supplemented with a number of primary amines, two new types of mitomycin analogs described as Type I and Type II are produced. Type I analogs are related to mitomycin C with the amine substitution at position C7 on the mitosane ring. Type II analogs also contain the same substitutions at C7 but the conformation of the mitosane ring is related to mitomycin B having an OH at positions C9a and a methyl substituted aziridine. The products obtained from the supplementation of the medium with methylamine, ethylamine, propylamine, propargylamine and 2-methylallylamine were isolated and characterized. In all cases the Type I analogs are more active in a prophage induction test and against L1210 lymphatic leukemia in mice. A number of other amines have been tested and shown to yield new products that have not yet been isolated. No secondary amines are incorporated.
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  • I. SALT FORMATION AND NORMAL KETALIZATION
    G. A. ELLESTAD, N. CANFIELD, R. A. LEESE, G. O. MORTON, J. C. JAMES, M ...
    1986 Volume 39 Issue 3 Pages 447-456
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The formation of monovalent and divalent salt complexes of maduramicin is described and the 13C NMR chemical shift assignments of these materials are tabulated and discussed. In the spectrum of the thallium salt, 20 of the 47 signals are split due to the thallium-carbon coupling. Similarly the preparation of both the free acid and the sodium salt complexes of the normal methyl and ethyl ketal derivatives of maduramicin are outlined. Their 13C NMR spectra are fully assigned together with discussion of displacements observed due to this derivatization.
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  • SALLY E. WILLIAMS, JOCHEN SCHACHT
    1986 Volume 39 Issue 3 Pages 457-462
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    In order to assess the potential importance of different cellular binding sites for the adverse effects of aminoglycosides (i.e. oto- and nephrotoxicity) the binding of neomycin and calcium to phospholipids and other anionic cell constituents was assayed in vitro. Phospholipids demonstrated binding affinities that strongly favored neomycin (Km, 10 to 100μm) over calcium (Km, 300 to 1, 120μm). Both neomycin and calcium showed strongest binding to lipids with monoester phosphate groups: phosphatidic acid, phosphatidylinositol 4-phosphate, and phosphatidylinositol 4, 5-bisphosphate. The lipids bound 0.2 to 0.4 molecules of neomycin and 0.5 to 1 molecule of calcium, respectively, per lipid. Anionic non-lipid compounds such as melanin, gangliosides or chondroitin sulfate were ineffective competitors of neomycin binding to lipids. The results emphasize the importance of phospholipids as cellular binding sites for aminoglycosides. Furthermore, if one considers extra- and intracellular calcium and neomycin concentrations, the relative affinity of lipids for these two compounds suggests an explanation for both the reversible and the essentially irreversible toxic effects of the aminoglycosides.
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  • PIA VILLA, FABRIZIO CORTI, AMALIA GUAITANI, IVAN BARTOSEK, FRANCO CASA ...
    1986 Volume 39 Issue 3 Pages 463-468
    Published: 1986
    Released on J-STAGE: April 19, 2006
    JOURNAL FREE ACCESS
    The effects of a new fluorinated macrolide (P-0501A) on drug metabolizing enzymes of rat liver were compared with three erythromycins-the base, the stearate and the estolate-after 7 days of dosing (1.36 mmol/kg po daily). The three erythromycins induced the synthesis of microsomal enzymes, but the products of their metabolism inactivated cytochrome P-450 in the order base<stearate<estolate. N-Demethylation of erythromycin and aminopyrine
    increased, while O-demethylation of 4-nitroanisole was reduced and hydroxylation of aniline was not changed after in vivo treatment. Pentobarbital sleeping time was prolonged and liver glutathione levels were lower in treated rats than in controls. In contrast to the three erythromycins, P-0501A did not induce the synthesis of microsomal enzymes, did not form an inactive complex with cytochrome P-450 and did not affect mono-oxygenase activities or pentobarbital narcosis.
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  • D. L. KERN, J. P. SCHAUMBERG, G. C. HOKANSON, J. C. FRENCH
    1986 Volume 39 Issue 3 Pages 469-470
    Published: 1986
    Released on J-STAGE: April 19, 2006
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  • JERAULD S. SKOTNICKI
    1986 Volume 39 Issue 3 Pages 471-472
    Published: 1986
    Released on J-STAGE: April 19, 2006
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  • SHIZUKA FUJII, KATSURO KUBO, OSAMU JOHDO, AKIHIRO YOSHIMOTO, TOMOYUKI ...
    1986 Volume 39 Issue 3 Pages 473-475
    Published: 1986
    Released on J-STAGE: April 19, 2006
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  • YOKO IKEDA, SHINICHI KONDO, DAISHIRO IKEDA, KAZUTERU YOKOSE, HIROAKI F ...
    1986 Volume 39 Issue 3 Pages 476-478
    Published: 1986
    Released on J-STAGE: April 19, 2006
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  • MICHAEL J. BASKER, RICHARD T. COOK, JOHN LOWTHER, ANDREW W. TAYLOR
    1986 Volume 39 Issue 3 Pages 479-482
    Published: 1986
    Released on J-STAGE: April 19, 2006
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  • DESMOND J. BEST, GEORGE BURTON, FRANK P. HARRINGTON, JOHN LOWTHER
    1986 Volume 39 Issue 3 Pages 483-485
    Published: 1986
    Released on J-STAGE: April 19, 2006
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