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I. TAXONOMY OF PRODUCING ORGANISM
TAKAO OKAZAKI, RYUZO ENOKITA, HIROKO MIYAOKA, TOSHIO TAKATSU, AKIO TOR ...
1987 Volume 40 Issue 7 Pages
917-923
Published: July 25, 1987
Released on J-STAGE: April 19, 2006
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Strain SANK 60983, an actinomycete isolated from a soil sample, was found to produce the new glycopeptide antibiotics, chloropolysporins A, B and C. Short chains of spores occur in the both aerial and substrate hyphae.
meso-Diaminopimelic acid is present in the cell wall and galactose and arabinose in the whole-cell hydrolysate. Mycolic acid is absent. On the basis of the morphological, cultural and physiological characteristics, this strain was determined to be a new species of
Faenia designated
Faenia interjecta sp. nov. The type strain of
F. interjecta Okazaki and Enokita is SANK 60983.
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II. FERMENTATION, ISOLATION AND PHYSICO-CHEMICAL CHARACTERIZATION
TOSHIO TAKATSU, MUTSUO NAKAJIMA, SAE OYAJIMA, YASUHIRO ITOH, YOSHIHARU ...
1987 Volume 40 Issue 7 Pages
924-932
Published: July 25, 1987
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New antibiotics, chloropolysporins A, B and C, were found in the culture broth of an actinomycete identified as
Faenia interjecta sp. nov. They were isolated from the culture filtrate by column chromatography on various resinous adsorbents, followed by preparative reverse phase HPLC. Chloropolysporins A, B and C possessed all the same new aglycone composed of actinoidic acid, 3-chloro-4-hydroxyphenylglycine,
N-methyl-p-hydroxyphenylglycine and vancomycinic acid. From elementary analyses and mass spectroscopic measurements, the molecular formulae of chloropolysporins A, B and C appear to be C
89H
99O
39N
8Cl
3 (MW 2, 008), C
83H
89O
34N
8Cl
3 (MW 1, 846) and C
77H
79O
30N
8Cl
3 (MW 1, 700), respectively. Their physico-chemical characterizations including molecular formulae revealed that chloropolysporins A, B and C were new members of glycopeptide antibiotics.
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III. STRUCTURE ELUCIDATION OF CHLOROPOLYSPORINS
TOSHIO TAKATSU, SHUJI TAKAHASHI, MUTSUO NAKAJIMA, TATSUO HANEISHI, TAK ...
1987 Volume 40 Issue 7 Pages
933-940
Published: July 25, 1987
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Structure elucidations of chloropolysporins A, B and C were achieved mainly by chemical degradation studies. These components possessed the same pseudoaglycone in common and their structures were closely related to that of β-avoparcin. The structures of chloropolysporins differ from that of β-avoparcin in the presence of vancomycmic acid moiety instead of monodechlorovancomycinic acid moiety and glucose, not ristosaminylglucose, in its side chain. Chloropolysporin C was identified as derhamnosylchloropolysporin B based on its
1H NMR and mass spectral analysis and degradation studies. Two minor components, chloropolysporins D and E, were identified as the epimers of each of chloropolysporins B and C, respectively, based on their Cotton effects and retention times on reverse phase HPLC.
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IV. PARTIALLY DEGLYCOSYLATED DERIVATIVES
TOSHIO TAKATSU, SHUJI TAKAHASHI, YASUYUKI TAKAMATSU, TETSUYA SHIOIRI, ...
1987 Volume 40 Issue 7 Pages
941-945
Published: July 25, 1987
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Chloropolysporins A, B and C, new members of the glycopeptide antibiotic family, were enzymatically and chemically converted to their partially deglycosylated derivatives. The α- and β-avoparcins were also deglycosylated by the same method. The conversions were achieved by treatments with rhamnosidase (Naringinase) and α-mannosidase, and by mild acid hydrolysis.
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V. COMPARATIVE STUDIES OF THE BIOLOGICAL PROPERTIES
TOSHIO TAKATSU, TOSHIAKI KATAYAMA, MUTSUO NAKAJIMA, SHUJI TAKAHASHI, T ...
1987 Volume 40 Issue 7 Pages
946-952
Published: July 25, 1987
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Chloropolysporins A, B and C, as well as derivatives prepared from this group and α-and β-avoparcins by enzymatic and mild acid hydrolysis, were active against Gram-positive bacteria including clinically isolated methicillin-resistant Staphylococci (MIC 0.39 - 6.25 /Jg/ml) and anaerobic enterobacteria (MIC 0.10-1.56 μg/ml). Derhamnosyl and demannosyl derivatives from both groups of antibiotics showed stronger activities than the parent compounds. The MIC and MBC values against Staphylococci were similar and were not effected by the presence of serum. Moreover, chloropolysporin C exhibited very strong synergistic effects with various β-lactam antibiotics against methicillin-resistant strains of
Staphylococcus aureus. Some of these compounds also protected mice from experimental infection with
S. aureus. Acute toxicities of chloropolysporins by intravenous administration ranged from 215-290mg/kg in mice. Chloropolysporin B as well as other glycopeptide antibiotics, showed distinctive growth promoting activity in broiler chickens.
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I. CALCIUM 3-HYDROXYQUINOLINE-2-CARBOXYLATE FROM A STREPTOMYCES
SABINE BREIDING-MACK, AXEL ZEECK
1987 Volume 40 Issue 7 Pages
953-960
Published: July 25, 1987
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Streptomyces griseoflavus subsp. (Gö 3592) was investigated by chemical screening methods. The mycelium contained gilvocarcin V (
1). The culture filtrate contained the calcium salt of 3-hydroxyquinoline-2-carboxylic acid (
2) confirmed by spectroscopic methods and by a 5-step partial synthesis of the free acid (
3).
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KENICHI YANO, JUNJI OONO, KINICHI MOGI, TAKEMITSU ASAOKA, TOSHIAKI NAK ...
1987 Volume 40 Issue 7 Pages
961-969
Published: July 25, 1987
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A strain of streptomycete was found to produce a new antibiotic pyrroxamycin. This compound was isolated from the culture broth of
Streptomyces sp. S46506. The chemical structure was determined to be 4, 5-dichloro-2-(6', 8'-dichloro-4'
H-1', 3'-benzodioxin-4'-yl)-3-nitropyrrole by its chemical character and
1H and
13C NMR spectral analysis. Pyrroxamycin was active against Gram-positive bacteria and dermatophytes.
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SIEGFRIED B. CHRISTENSEN, H. S. ALLAUDEEN, MICHAEL R. BURKE, STEVEN A. ...
1987 Volume 40 Issue 7 Pages
970-990
Published: July 25, 1987
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An extensive taxonomic investigation identified strain SK&F-AAJ-271 as a new species, designated
Actinomadura parvosata. Fermentations of this organism produce a complex of acidic, lipophilic glycopeptide antibiotics, the parvodicins. Structures for seven of the isolated components were derived from a combination of mass spectral, high-field NMR and chemical techniques. The
O-acetyl functionality present in two of the isolated components is a structural feature unique among the known members of this class of antibiotics. The parvodicins are active
in vitro against a range of Gram-positive bacteria. The most active parvodicin, C
1, produces high serum levels
in vivo and has the potential for a long duration of action.
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TAKAYUKI NAITO, HIDEAKI HOSHI, SHIMPEI ABURAKI, YOSHIO ABE, JUN OKUMUR ...
1987 Volume 40 Issue 7 Pages
991-1005
Published: July 25, 1987
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The synthesis and structure-activity relationships of 7-[D-α-amino-α-(4-hydroxyphenyl)-acetamido]-3-[(
Z)-l-propenyl]-3-cephem-4-carboxylic acid (BMY-28100) and its analogs in the 3- and 7-side chains are described. The 3-(substituted-propenyl) groups were introduced by the Wittig reaction of the 3-phosphoniomethyl cephems which were derived from the 3-chloromethyl derivatives. The reaction gave predominantly the
cis isomer regarding the 3-side chain. The
cis and
trans isomers showed characteristic UV and
1H NMR spectra. Most of cephems of this series were well-absorbed orally and more active both
in vitro and
in vivo than cephalexin and cefaclor against Gram-positive organisms. Their Gram-negative activity varied depending on the 3- and 7-substituents. Compounds with a
cis-propenyl group showed the best Gram-negative activity among the 3-alkenyl analogs prepared, whereas the D-4-hydroxyphenylglycyl and D-4-hydroxy-3-methoxyphenylglycyl substitutions in the 7-side chain were found suitable to improve the Gram-negative activity of 3-
cis-propenyl series of cephalosporins to the level favorably compared with that of cefaclor. The 3, 4-dihydroxyphenyl analog was found to be metabolized
in vivo to the 4-hydroxy-3-methoxyphenyl derivative and, therefore, showed nearly the same
in vivo activity as that of the latter. BMY-28100 was selected for further evaluation and the results will be reported in the subsequent paper.
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XII. ANTIBACTERIAL IN VITRO EVALUATION OF 10-DIHYDRO-10-DEOXO-11-AZAERYTHROMYCIN A: SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIP OF ITS ACYL DERIVATIVES
SLOBODAN DJOKIC, GABRIJELA KOBREHEL, GORJANA LAZAREVSKI
1987 Volume 40 Issue 7 Pages
1006-1015
Published: July 25, 1987
Released on J-STAGE: April 19, 2006
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Antibacterial
in vitro evaluation of 10-dihydro-10-deoxo-11-azaerythromycin A
† (
5), the new 15-membered semi-synthetic macrolide antibiotic with nitrogen as additional atom in the aglycone ring of erythromycin A (
1), was reported. Although amine (
5) and its 13, 14-cyclic carbonate (
14) were less active than 1 against erythromycin-sensitive
Staphylococcus aureus strains they showed advantageous properties against Gram-negative test organisms and clinical isolates. Also, a large number of acyl derivatives of
5 were synthesized and evaluated. N-11 monoacyl compounds exhibited 2 to 50 times lower
in vitro antibacterial efficacy than the parent amine (
5).
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TETSUO KOBAYASHI, SUEHARU HORINOUCHI, TAKESHI UOZUMI, TERUHIKO BEPPU
1987 Volume 40 Issue 7 Pages
1016-1022
Published: July 25, 1987
Released on J-STAGE: April 19, 2006
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Streptothricin acetyltransferase was purified from
Streptomyces lividans harboring a plasmid which carried the streptothricin-resistance gene cloned from a streptothricin-producing strain,
Streptomyces lavendulae No. 1080. Some properties of the enzyme were determined and the reaction product was identified to be
Nβ-acetylstreptothricin by NMR spectroscopy.
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SYNTHESIS AND BIOLOGICAL PROPERTIES
ANDRZEJ CZERWINSKI, WILFRIED A. KÖNIGT, PAWEL SOWINSKI, EDWARD BO ...
1987 Volume 40 Issue 7 Pages
1023-1027
Published: July 25, 1987
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Synthesis and biological properties of a number of amides of polyene macrolide antibiotic aureofacin obtained in the reaction of the antibiotic with various glycine esters are described.
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WERNER E. G. MÜLLER, NORBERT WEISSMANN, ARMIN MAIDHOF, MICHAEL BA ...
1987 Volume 40 Issue 7 Pages
1028-1035
Published: July 25, 1987
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Under otherwise identical conditions, deoxyspergualin preferentially inhibits the growth of the T-cell leukemia line L5178y; an effective dose for a 50% inhibition (ED
50) of 0.0007μM was determined. A much weaker cytostatic activity was found for murine lymphocytes (ED
50: approximately 25 μM) and for CV-1 monkey kidney cells (ED
50: 16.3 μM). Deoxyspergualin causes biphasic and differential effects on DNA metabolism of murine T and B lymphocytes. At lower concentrations (0.3 - 5 μM) the [
3H]TdR incorporation into nonactivated or lipopolysaccharide-activated lymphocytes is significantly stimulated by the compounds; this effect was not observed with lymphocyte cultures stimulated with concanavalin A. This change of TdR incorporation rates was found to parallel with the variations of DNA polymerase α activity. Deoxyspergualin causes an additive effect together with bleomycin and a significant synergistic cytostatic effect in combination with avarol and avarone. Moreover, it is reported that deoxyspergualin causes neither a selective inhibitory effect on DNA-, RNA- or protein synthesis nor an alteration of the intracellular distribution pattern of the Ro and La antigens. However, detailed enzymic studies revealed that deoxyspergualin reduces DNA polymerase α but not β activity in lymphocytes at the ED
50 concentration of this compound. These results support previous documentations that deoxyspergualin is of potential clinical usefulness (a) in treatment of certain tumors and (b) in organ transplantation.
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S. K. DAS, S. MUKHERJEE, S. MAJUMDAR, S. BASU, S. K. BOSE
1987 Volume 40 Issue 7 Pages
1036-1043
Published: July 25, 1987
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Mycobacillin partially quenched the strong fluorescence when 1-anilino naphthalene 8-sulfonate (ANS) was added to protoplast or plasma membrane but is without any effect on weak fluorescence when added to cell-free extract. There are two classes of ANS binding sites on protoplast or plasma membrane of which one class is sensitive to mycobacillin, being competitively abolished by it. Mycobacillin also non-competitively inhibits the binding of pyrene, a lipid specific probe. Thus it follows from the inhibition by mycobacillin of ANS or pyrene binding to protoplast or plasma membrane that the site of action of the antibiotic is located in the plasma membrane. Interaction between mycobacillin and the plasma membrane is physico-chemical in nature.
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STEPHEN W. MAMBERT, WANDA G. OKASINSKI, CHERYL D. PINTER, JOSEFINO B. ...
1987 Volume 40 Issue 7 Pages
1044-1049
Published: July 25, 1987
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The novel antitumor antibiotics PD 114, 759 and PD 115, 028 were evaluated for their ability to cause repairable DNA damage and the induction of SOS functions in bacterial systems. PD 114, 759 and PD 115, 028 were preferentially toxic to DNA repair-defective
Escherichia coll WP100
uvrA recA in comparison to wild-type
E. coll WP2 at concentrations of lO-30 μg/ml in agar diffusion assays. Both compounds were inducers of cell filamentation and prophage λ (two
E. coli SOS functions) at concentrations of 0.1-1 μg/ml. In addition, the ability of PD 114, 759 and PD 115, 028 to retain their filamentation-inducing effects under both aerobic conditions and anaerobic conditions suggests that a bioreductive, rather than an oxygen-requiring, mechanism is involved in the DNA-reactive effects of these agents.
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TRIPTIKUMAR MUKHOPADHYAY, KIRITY ROY, Louis COUTINHO, R. H. RUPP, B. N ...
1987 Volume 40 Issue 7 Pages
1050-1052
Published: July 25, 1987
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KOJI KOBAYASHI, CHIKAO NISHINO, JUNICHI OHYA, SHIGERU SATO, TAKASHI MI ...
1987 Volume 40 Issue 7 Pages
1053-1057
Published: July 25, 1987
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HAMAO UMEZAWA, SHOHACHI NAKAJIMA, HIROYUKI KAWAIT, NOBUYASU KOMESHIMAT ...
1987 Volume 40 Issue 7 Pages
1058-1061
Published: July 25, 1987
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KYUICHI NEMOTO, FUMINORI ABE, TERUYA NAKAMURA, MASAAKI ISHIZUKA, TOMIO ...
1987 Volume 40 Issue 7 Pages
1062-1064
Published: July 25, 1987
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KYUICHI NEMOTO, JUNPEI ITO, FUMINORI ABE, TERUYA NAKAMURA, TOMIO TAKEU ...
1987 Volume 40 Issue 7 Pages
1065-1066
Published: July 25, 1987
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ANDRZEJ CZERWINSKI, WILFRIED A. KÖNIG, SANTE MARTELLI, PAWEL SOWI ...
1987 Volume 40 Issue 7 Pages
1067-1070
Published: July 25, 1987
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GIUSEPPE CASSINELLI, MARZIA BALLABIO, ARPAD GREIN, SERGIO MERLI, GIOVA ...
1987 Volume 40 Issue 7 Pages
1071-1074
Published: July 25, 1987
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AKIRA NAKAGAWA, NOBUKO FUKAMACHI, KOHJI YAMAKI, MASAHIKO HAYASHI, SACH ...
1987 Volume 40 Issue 7 Pages
1075-1076
Published: July 25, 1987
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HIROO HOSHINO, NOBUAKI SHIMIZU, NOBUYOSHI SHIMADA, TOMOHISA TAKITA, TO ...
1987 Volume 40 Issue 7 Pages
1077-1078
Published: July 25, 1987
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Dr. M. G. BRAZHNIKOVA
1987 Volume 40 Issue 7 Pages
1079-1080
Published: July 25, 1987
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