The Journal of Antibiotics

FERMENTATION, ISOLATION, CHARACTERIZATION AND STRUCTURE OF ANTIBIOTIC U-58, 431

L. SLECHTA, C. G. CHIDESTER, F. REUSSER

1980 Volume 33 Issue 9 Pages 919-923
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.919

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A new antibiotic U-58, 431 has been isolated from the fermentation broth of Streptomyces helicus DIETZ and Li, sp. n. (UC-5837) and the structure of this antibiotic, namely, 6-amino-3, 4, 5, 8-tetrahydro-4, 9-dihydroxy-3-methyl-5, 8-dioxo-1, 4-ethano-1H-2-benzopyron-7-carboxamide has been determined by X-ray crystallography. The antibiotic inhibits a variety of Gram-positive and Gram-negative bacteria in vitro. However, it is toxic to mice and does not protectexperimentally infected animals when administered at the maximum tolerated dose.

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STUDIES ON A NEW AMINOGLYCOSIDE ANTIBIOTIC, DACTIMICIN

I. PRODUCING ORGANISM AND FERMENTATION

TAKASHI SHOMURA, MICHIO KOJIMA, JUNKO YOSHIDA, MITSUGU ITO, SHOICHI AM ...

1980 Volume 33 Issue 9 Pages 924-930
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.924

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The producing organism of a new antibiotic, dactimicin, is described. The presence of finger-shaped sporangia bearing motile spores, the absence of aerial mycelium and its cell wall of type II, ascribe this organism to the genus Dactylosporangiran. The cultural and physiological features distinguish this organism from all the described Dactylosporangium species. Therefore, it is considered to be a new species for which the name Dactylosporangium matsuzakiense sp. nov. is proposed. Fermentation of dactimicin is also described.

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TETRONIC ACID DERIVATIVES FROM ASPERGILLUS PANAMENSIS

PRODUCTION, ISOLATION, CHARACTERIZATION AND BIOLOGICAL ACTIVITY^*

H. ANKE, H. SCHWAB, H. ACHENBACH

1980 Volume 33 Issue 9 Pages 931-939
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.931

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When Aspergillus pauamensis, CBS 120.45, was grown on a medium with high carbon and low nitrogen content, it was found to produce six antibiotically active metabolites. All compounds were identified as tetronic acid derivatives; three of them were found to be identical with gregatins A, B, and D, previously reported as metabolites of Cephalosporiuin gregatum. The other three compounds are new. All six compounds show antibacterial activity towards Gram-negative and Gram-positive bacteria. Five of the antibiotics exhibit inhibitory effects on the macromolecular syntheses in cells of the ascitic form of EHRLICH carcinoma (ECA) of mice.

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TETROCARCINS, NOVEL ANTITUMOR ANTIBIOTICS

I. PRODUCING ORGANISM, FERMENTATION AND ANTIMICROBIAL ACTIVITY

FUSAO TOMITA, TATSUYA TAMAOKI

1980 Volume 33 Issue 9 Pages 940-945
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.940

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A novel antitumor antibiotic complex has been obtained from the culture broth of Actinomycete strain DO-11 (KY11091) isolated from a soil sample collected in Sendai, Miyagi, Japan. On the taxonomic studies the producing organism is described as Micromonospora chalcea KY11091. For the production of the antibiotics, soluble starch served as a good carbon source and yeast extract was the best nitrogen source tested. The antibiotic complex designated as tetrocarcins is active against Gram-positive bacteria, but is not active against Gram-negative bacteria. Tetrocarcin A showed bacteriocidal activity against Bacillus subtilis.

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TETROCARCINS, NOVEL ANTITUMOR ANTIBIOTICS

II. ISOLATION, CHARACTERIZATION AND ANTITUMOR ACTIVITY

TATSUYA TAMAOKI, MASAJI KASAI, KUNIKATSU SHIRAHATA, SHUJI OHKUBO, MAKO ...

1980 Volume 33 Issue 9 Pages 946-950
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.946

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Novel antitumor antibiotics, tetrocarcin complex composed of three components (A, B and C) were isolated from the culture broth of Micromonospora chalcea KY11091 through various procedures. Tetrocarcins showed marked activity against experimental tumors such as mouse sarcoma 180 and mouse leukemia P388. Multiple injections showed better therapeutic effect against tumors. Mode of action of tetrocarcin A against Bacillus subtilis was found to be through the inhibition of RNA synthesis.

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INCREASED PRODUCTION OF SAFRAMYCIN A AND ISOLATION OF SAFRAMYCIN S

TADASHI ARAI, KATSUHIRO TAKAHASHI, KIMIKO ISHIGURO, KATSUKIYO YAZAWA

1980 Volume 33 Issue 9 Pages 951-960
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.951

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This paper reports on an increased production of saframycin A, which is a satellite antibiotic to streptothricin and a trace component in the culture of Streptomyces lavendulae No. 314. Some improvement in the yield of the antibiotic was attained by supplementing the standard medium with two end-produtcs of metabolic pathways related to saframycin biosynthesis. A further significant increase of saframycin A potency could be attained by addition
of NaCN to the culture broth. Finally, a drastic degradation of saframycin A in the culture was successfully prevented by maintaining the pH lower than 5.5 after peak production of the antibiotic. The combined application of these improvements resulted in approximately 1, 000-fold increase in saframycin A production as compared with the parental level. The precursor of saframycin A in the culture, which yielded saframycin A upon cyanation
was isolated, characterized and named saframycin S. Physicochemical properties of saframycin S were described and structural formulae were discussed.

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NEW ANTIBIOTICS, CARBAZOMYCINS A AND B

II. STRUCTURAL ELUCIDATION

KATSU-ICHI SAKANO, SHOSHIRO NAKAMURA

1980 Volume 33 Issue 9 Pages 961-966
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.961

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The structures of carbazomycins A and B are elucidated to be 3, 4-dimethoxy-1, 2-dimethylcarbazole and 4-hydroxy-3-methoxy-1, 2-dimethylcarbazole, respectively. Further, ¹³C-chemical shifts of carbazomycins and their derivatives are assigned simultaneously.

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PAPULACANDINS, A NEW FAMILY OF ANTIBIOTICS WITH ANTIFUNGAL ACTIVITY

STRUCTURES OF PAPULACANDINS A, B, C AND D

PETER TRAXLER, HANS FRITZ, HERMANN FUHRER, WILHELM J. RICHTER

1980 Volume 33 Issue 9 Pages 967-978
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.967

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The structures of the papulacandins A, B, C and D, new antibiotics of Papularia sphaerosperma have been established by means of spectral analysis and degradation reactions. Base catalysed hydrolysis of the main product papulacandin B (1) gave two new hydroxylated long-chain unsaturated fatty acids 5 and 6 along with a hitherto unknown spirocyclic diglycoside 7. The structure of 7 was determined by further degradation reactions. The positions of attachment of the two fatty acids to the spirocyclic diglycoside 7 through ester-bonds were established by selective base catalysed hydrolysis of 1 and spectral analysis of 1 and some derivatives and degradation products thereof. The structures of papulacandin A (2), papulacandin C (3) and papulacandin D (4) were determined in an analogous way.

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STUDIES ON THE IONOPHOROUS ANTIBIOTICS. XXVI

THE ASSIGNMENTS OF THE ¹³C-NMR SPECTRA OF LONOMYCIN A AND MUTALOMYCIN

HARUO SETO, KAZUTOSHI MIZOUE, NOBORU OTAKE

1980 Volume 33 Issue 9 Pages 979-988
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.979

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All resonances observed in the ¹³C-nmr spectra of the polyether antibiotics lonomycin A and mutalomycin have been assigned by the aid of biosynthetic method, selective proton decoupling as well as comparison with structurally related compounds.

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THE STRUCTURE OF LIENOMYCIN, A PENTAENE MACROLIDE ANTITUMOR ANTIBIOTIC

I. THE STRUCTURE OF THE CARBON SKELETON AND THE LOCATION OF FUNCTIONALITIES

J. PAWLAK, J. ZIELINSKI, J. GOLIK, J. GUMIENIAK, E. BOROWSKI

1980 Volume 33 Issue 9 Pages 989-997
Published: 1980
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DOIhttps://doi.org/10.7164/antibiotics.33.989

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The structure of a novel type of pentaene macrolide named lienomycin (I) was established by selected chemical transformations of I followed by MS examination of the products. This report provides evidence on the structure of the carbon skeleton of I and on the location of functionalities.

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THE STRUCTURE OF LIENOMYCIN, A PENTAENE MACROLIDE ANTITUMOR ANTIBIOTIC

II. THE LOCATION OF THE PENTAENE CHROMOPHORE AND OF SIX ISOLATED DOUBLE BONDS. THE COMPLETE STRUCTURE OF THE ANTIBIOTIC

J. PAWLAK, J. ZIELINSKI, J. GOLIK, E. JERECZEK, E. BOROWSKI

1980 Volume 33 Issue 9 Pages 998-1004
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.998

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The locations of the isolated double bonds and of the pentaene chromophore in lienomycin (I) were established by chemical degradation of I followed by MS and ¹H NMR examination of the products. The complete structure of the antibiotic is proposed.

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SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 7β-[2-(2-AMINOTHIAZOL-4-YL)ACETAM IDO]- CEPHALOSPORIN DERIVATIVES

I. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 7β-[2-ALKYLAND 2-HYDROXY-2-(2-AMINOTHIAZOL-4-YL)- ACETAMIDO]CEPHALOSPORINS

MICHIHIKO OCHIAI, AKIRA MORIMOTO, YOSHIHIRO MATSUSHITA, TATSUHIKO KANE ...

1980 Volume 33 Issue 9 Pages 1005-1013
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1005

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2-Alkyl- and 2-hydroxy derivatives of 7β-[2-aminothiazol-4-yl)acetamido]cephalosporins were synthesized to improve the antibacterial activity of the parent compounds especially against β-lactamase-producing organisms. Some of these compounds showed an increase in activity against Serratia marcescens(Xb, XXIIIa) and Enterobacter cloacae (Xb, XIV). The 2, 2-dimethyl derivative (XXVIHb) showed a definite loss of activity.

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SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 7β-[2-(2-AMINOTHIAZO L-4-YL)ACETAMIDO]- CEPHALOSPORIN DERIVATIVES

II. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 7β-[2-(2-AMINOTHIAZOL- 4-Y L) ACETA MIDO]-7α-METHOXYCEPHALOSPORINS

MICHIHIKO OCHIAI, AKIRA MORIMOTO, YOSHIHIRO MATSUSHITA, MAKOTO KIDA

1980 Volume 33 Issue 9 Pages 1014-1021
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1014

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7β-[2-(2-Aminothiazol-4-yl)acetamido]-7α-methoxycephalosporins were synthesized both by acylation of the 7β-amino-7α-methoxycephalosporin compound (VIII) and a new direct acyl-exchange reaction of 7α-methoxy-7β-phosphoramido compound (VII). Some of these compounds (IXa, IXb) showed higher antibacterial activity than the 7α-unsubstituted compound against β-lactamase-producing strains of Serratia marcescens and Proteus vulgaris.

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SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 7β-[2-(2-AMINOTHIAZOL-4-Y L)ACETAMIDO]- CEPHALOSPORIN DERIVATIVES

III. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 7β-[2-AMINO- 2-(2-A MINOTHIAZOL-4-YL)ACETAMIDO]CEPHALOSPORINS

MICHIHIKO OCHIAI, AKIRA MORIMOTO, TAIITI OKADA, YOSHIHIRO MATSUSHITA, ...

1980 Volume 33 Issue 9 Pages 1022-1030
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1022

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New derivatives of 7β-[2-(2-aminothiazol-4-yl)acetamido]cephalosporins having amino group at the 2-position of the 7-acyl moiety were synthesized in the hope that they would show improved antibacterial activity. Some of these compounds (XXa, XXd, XVb) showed improved activity against Enterobacter cloacae. Replacement of the annular amino group by a methyl group caused loss of activity.

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DIASTEREOMERIC 7-α-UREIDOACETYL CEPHALOSPORINS

V. ANTIMICROBIAL ACTIVITY, β-LACTAMASE STABILITY AND PHARMACOKINETICS OF 7-(α-UREIDO-2-AMINO-4- THIAZOLYLACETYL)-CEPHALOSPORINS

I. POLACEK, B. STARKE

1980 Volume 33 Issue 9 Pages 1031-1036
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1031

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Diastereomeric 7-(α-ureido-2-amino-4-thiazolylacetyl)cephalosporins are broad-spectrum antimicrobial agents with activity mainly against Gram-negative bacteria. The L-isomers were more potent than the D-isomers. All compounds showed some degree of stability to β-lactamases. The compounds reached high serum and tissue fluid levels and were excreted unchanged mainly in urine.

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CEFOXITIN RESISTANCE BY A CHROMOSOMAL CEPHALOSPORINASE IN ESCHERICHIA COLI

IKUKO TAKAHASHI, TETSUO SAWAI, TOHRU ANDO, SABURO YAMAGISHI

1980 Volume 33 Issue 9 Pages 1037-1042
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1037

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Cefoxitin resistance, an unique property found in clinical isolates of Escherichia coli was investigated. Cefoxitin resistant strains, 255 and GN206, produced cephalosporinase constitutively. The cephalosporinase was located in the periplasm, and its production was considered to be mediated by chromosomal gene(s). Cephalosporinase-less mutants from both strains were susceptible to cefoxitin as well as other β-lactam antibiotics, suggesting that the cephalosporinase was responsible for the resistance to β-lactam antibiotics including cefoxitin. The cephalosporinases from the E. coli strains were partially purified and their enzymological properties were compared with those of cephalosporinases of Citrobacter freundii and Proteus morganii. Although the cephalosporinases of E. coli, as well as other cephalosporinases, showed little activity for cefoxitin-hydrolysis, the E. coli cephalosporinases exhibited a significantly higher affinity for cefoxitin than other cephalosporinases. It was assumed that the E. coli enzyme located around the targets of cefoxitin protected the targets from the antibiotic by its high affinity for the antibiotic.

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INHIBITION OF TYROSINE HYDROXYLASE, A Fe(II)-STIMULATED MONOOXYGENASE, BY BLEOMYCIN

KAZUHIRO OKA, TAKESHI KATO, TOMOHISA TAKITA, TOMIO TAKEUCH, HAMAO UMEZ ...

1980 Volume 33 Issue 9 Pages 1043-1047
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1043

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Tyrosine hydroxylase was shown to be inhibited in vitro by bleomycin. At a concentration of 1×10^-4 M, copper-free BLM-A2 inhibited tyrosine hydroxylase activity by 50%, and all other bleomycins investigated including copper-bound BLM-A2 showed similar degrees of inhibition of tyrosine hydroxylase. The kinetic data have shown that the inhibition by BLM-A2 is competitive with a tetrahydropterin cofactor (6-methyl-tetrahydropterin) and uncompetitive with tyrosine. The inhibition of tyrosine hydroxylase by bleomycin was not reversed by Fe(II) or superoxide dismutase. These results suggest that the inhibition may be neither due to the chelating action of bleomycin with ferrous ion nor due to the production of superoxide and hydroxyl radicals by the formation of an oxygen-labile Fe(II)-bleomycin complex.

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EFFECTS OF SEVERAL ANTHRACYCLINE ANTITUMOR ANTIBIOTICS ON THE TRANSCRIPTIONAL ACTIVITY OF ISOLATED NUCLEOLI

VIRGIL H. DUVERNAY, STANLEY T. CROOKE

1980 Volume 33 Issue 9 Pages 1048-1053
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1048

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The class II anthracycline antitumor antibiotics musettamycin, rudolfomycin, aclacinomycin and marcellomycin, which were shown in earlier studies to preferentially inhibit the synthesis of nucleolar RNA in intact tumor cells, were studied in an isolated nucleolar transcriptional assay. Their effects were compared with those of the nucleolar non-selective anthracyclines adriamycin, carminomycin and pyrromycin, as well as with the 10-descarbomethoxyanalogs of marcellomycin and rudolfomycin. The isolated nucleolar transcriptional assay was found to have linear activity for 30 minutes at 30°C. At increasing concentrations of α-amanatin up to 200μg/ml, the maximum degree of inhibition of transcriptional activity was found to be 6-7%. The ranking of nucleolar RNA synthesis inhibitory potencies of the class I and II anthracyclines and the 10-descarbomethoxy-analogs obtained previously in intact cells was reproduced in the isolated nucleoli assay system described here. Thus, evidence for the use of this assay as a screen for nucleolar active antitumor agents is presented.

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ANTITUMOR EFFECT OF BACTOBOLIN AND ITS INFLUENCE ON MOUSE IMMUNE SYSTEM AND HEMATOPOIETIC CELLS

MASAAKI ISHIZUKA, SHIGEKI FUKASAWA, TORU MASUDA, JUNICHI SATO, NOBUO K ...

1980 Volume 33 Issue 9 Pages 1054-1062
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1054

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Bactobolin prolonged survival period of mice bearing leukemia L-1210 in various dose schedules. The administration of bactobolin before or at time of immunization with sheep red blood cells (SRBC) did not affect antibody formation and delayed-type hypersensitivity (DTH) to SRBC. The administration after immunization suppressed antibody formation markedly but not DTH response. Bactobolin showed stronger suppressive action on antibody formation in vitro than mitomycin C. Bactobolin did not reduce establishment of tumor immunity which was mediated by T cells and macrophages. Comparing to other antitumor antibiotics which were effective against L-1210, bactobolin did not affect phagocytosis of mouse peritoneal macrophages. It has an extremely low toxicity to mouse spleen cells treated by concanavalin A (Con A) and lipopolysaccharide (LPS). It did not affect colony formation of mouse bone marrow cells in the presence of LPS-induced colony stimulating factor. The administration of bactobolin did not reduce the number of leucocytes in peripheral blood. From these results, the usefulness of bactobolin in the treatment of cancer was discussed.

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THE MECHANISM OF ACTION OF POLYCHLOROSUBTILIN

IBRAHIM R. SHIMI, FAHMY T. ALI

1980 Volume 33 Issue 9 Pages 1063-1070
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1063

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Polychlorosubtilin (PCS) inhibits the growth of Escherichia coli. The antibiotic affected neither respiration nor glycolysis while the synthesis of nucleic acids and proteins were feebly hindered. Formation of aminoacyl-tRNA, peptide bonds and translocation from A to P sites of ribosomes were insignificantly influenced by the drug. The antibiotic exerted its effect(s) on ribosomes by interfering with the 30 S subunits. The 23 S and 30 SP were both sensitive to the drug but the latter was more obviously affected. Changes after developing resistance to the drug by the bacteria were localized in the 30 SP, 23 S and accordingly the 30 S subunits. The principal action of PCS was to cause multisited miscoding upon the incorporation of labeled aminoacyl-tRNA, therefore, malformed protein fractions (abnormal) were synthesized. As a natural consequence such abnormal fractions would not be expected to manifest the vital metabolic activities in the normal way.

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THE BASE CATALYZED REARRANGEMENT OF 3-O-DEMETHYLFORTIMICIN A

PAUL A. LARTEY, DAVID J. GRAMPOVNIK

1980 Volume 33 Issue 9 Pages 1071-1073
Published: 1980
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DOIhttps://doi.org/10.7164/antibiotics.33.1071

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OGANOMYCINS, NEW 7-METHOXYCEPHALOSPORINS PRODUCED BY PRECURSOR FERMENTATION WITH HETEROCYCLIC THIOLS

TAKASHI OSONO, SHUNICHI WATANABE, TAKESHI SAITO, HIROSHI GUSHIMA, KEIS ...

1980 Volume 33 Issue 9 Pages 1074-1078
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1074

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CHEMISTRY OF BLEOMYCIN. XXVII CLEOMYCIN, A NEW FAMILY OF BLEOMYCIN-PHLEOMYCIN GROUP

HAMAO UMEZAWA, YASUHIKO MURAOKA, AKIO FUJII, HIROSHI NAGANAWA, TOMOHIS ...

1980 Volume 33 Issue 9 Pages 1079-1082
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1079

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BIOCONVERSION OF 5-O-(4', 6'- DIDEOXY-3'-C-ACETYL-β-D- XYLOHEXOPYRANOSYL)- PLATENOLIDE-II BY STREPTOMYCES HYGROSCOPICUS IMET JA 6599-NG-33-354r

U. GRÄFE, G. REINHARDT, W. SCHADE, P. MÜHLIG, H. THRUM, L. R ...

1980 Volume 33 Issue 9 Pages 1083-1085
Published: 1980
Released on J-STAGE: April 12, 2006

DOIhttps://doi.org/10.7164/antibiotics.33.1083

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