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H. ANKE, T. KEMMER, G. HÖFLE
1981 Volume 34 Issue 8 Pages
923-928
Published: 1981
Released on J-STAGE: April 12, 2006
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Five structurally related, angular azaphilones, the deflectins, were isolated from the mycelia of
Aspergillus deflectus. The structures of all compounds have been established. Besides the inhibitory effects on the growth of bacteria and fungi, these compounds showed lytic activity towards bacteria and erythrocytes and cytotoxic activity towards cells of the ascitic form of Ehrlich carcinoma of mice. The inhibitory effects of the deflectins could be reversed by the addition of serum or serum albumin.
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I. TAXONOMY OF PRODUCING ORGANISM AND FERMENTATION
YASUHIRO ITOH, RYUZOU ENOKITA, TAKAO OKAZAKI, SEIGO IWADO, AKIO TORIKA ...
1981 Volume 34 Issue 8 Pages
929-933
Published: 1981
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A soil isolate of actinomycete, strain No. 43871 produced a new antifungal antibiotic, candiplanecin. Pale brownish to yellow orange color of colonies on agar media, the formation of bottle-shaped, cylindrical sporangia bearing motile spores and the presence of
meso-DAP and glycine in the cell wall ascribed this strain to genus
Ampullariella. From its morphological characteristics together with the cultural and physiological features, this strain was determined to be a new subspecies of
Ampullariella regularis and designated as
Ampullariella regularis subsp.
mannitophila subsp. nov.(FERM-P No. 5646). Production of candiplanecin was carried out by conventional submerged culture, in which 2 μg/ml as the highest antibiotic titer was obtained.
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II. ISOLATION, PHYSICO-CHEMICAL CHARACTERIZATION AND BIOLOGICAL ACTIVITIES
YASUHIRO ITOH, AKIO TORIKATA, CHIWAKO KATAYAMA, TATSUO HANEISHI, MAMOR ...
1981 Volume 34 Issue 8 Pages
934-937
Published: 1981
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New antibiotic, candiplanecin, was found in the culture broth of an actinomycete identified as
Ampullariella regularis subsp.
mannitophila subsp. nov. Candiplanecin was produced by conventional submerged culture and isolated by column chromatography on Diaion HP 20 followed by extraction with ethyl acetate and further column chromatography on Sephadex LH-20 column and finally on PrepPAK-500/C18 column. The antimicrobial spectrum of the antibiotic revealed its activity against yeasts and fungi.
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I. TAXONOMY OF PRODUCING ORGANISM, ISOLATION, CHARACTERIZATION AND BIOLOGICAL ACTIVITIES OF RUBEOMYCIN A, A1, B AND B1
YASUO OGAWA, HIDEO SUGI, NOBORU FUJIKAWA, HIROYUKI MORI
1981 Volume 34 Issue 8 Pages
938-950
Published: 1981
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A new antibiotic complex has been obtained from the cultures of an actinomycete, strain FA-1180, isolated from a soil sample collected at lake side of Biwa in Japan. On the basis of taxonomic studies the producing microorganism is designated as
Actinomadura roseoviolacea var.
biwakoensis nov. var. The antibiotic complex belongs to the class of anthracycline glycoside antibiotics. All components form deep red fine needles on crystallization; components are named rubeomycin A, A
1, B and B
1. These components exhibit activity against Gram-positive bacteria as well as Yoshida sarcoma cell
in vitro. These components are also effective on P388 leukemia.
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I. ISOLATION AND CHARACTERIZATION OF VARIOUS BLOCKED MUTANTS
AKIHIRO YOSHIMOTO, YASUE MATSUZAWA, TOSHIKAZU OKI, TOMIO TAKEUCHI, HAM ...
1981 Volume 34 Issue 8 Pages
951-958
Published: 1981
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During genetic study on obtaining high-yield variants of aclacinomycin A-producer, a variety of blocked mutants were isolated from
Streptomyces galilaeus MA144-M1 and were characterized. The isolated mutants included those which accumulated only specific components of parental glycosides, those which produced new aklavinone glycosides devoid of parental rhodosamine or both rhodinose and cinerulose, those which produced non-glycosidic aglycones, and antibiotic-negative mutants, some of which were able to glycosidate exogenous aklavinone. By biotransformation with the aglycone feeding culture, the precursor activity of new aglycones was also tested. From the results and in relation to the characterization of isolated mutants, the biosynthetic pathway of aclacinomycin A and related antibiotics is discussed.
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II. STRUCTURE OF 2-HYDROXYAKLAVINONE AND NEW AKLAVINONE GLYCOSIDES
YASUE MATSUZAWA, AKIHIRO YOSHIMOTO, NORIO SHIBAMOTO, HIROYASU TOBE, TO ...
1981 Volume 34 Issue 8 Pages
959-964
Published: 1981
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Four blocked mutants of aclacinomycin-producing
Streptomyces galilaeus MA144-M1 produced new anthracyclinones; 2-hydroxyaklavinone, its non-esterified analog and 2-hydroxy-7-deoxyaklavi none, several new anthracyclines; 2-deoxyfucosyl-2-deoxyfucosyl-rhodosaminylaklavinone (MA144 U1), 2-deoxyfucosyl-rhodosaminylaklavinone (MA144 U2) and five aklavinone glycosides devoid of amino sugar, designated as MA144 U5, U6, U7, U8 and U9.
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T. SCHUPP, P. TRAXLER, J. A. L. AUDEN
1981 Volume 34 Issue 8 Pages
965-970
Published: 1981
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A recombinant strain of
Nocardia mediterranei was found to produce a number of new rifamycins which are structurally related to rifamycin S, rifamycin W and rifamycin G. This strain was derived from two
Nocardia mediterranei mutants by intraspecific recombination.
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PETER TRAXLER, THOMAS SCHUPP, HERMANN FUHRER, WILHELM J. RICHTER
1981 Volume 34 Issue 8 Pages
971-979
Published: 1981
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The structures of 3-hydroxyrifamycin S and six further novel ansamycins isolated from the recombinant strain R-21 of
Nocardia mediterranei were identified by spectroscopic methods. Three types of structure were distinguished: Type 1: Ansamycins of the rifamycin S type Type 2: Ansamycins of the rifamycin G type Type 3: Ansamycins of the rifamycin W type
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YOUXIN SONG, TSUTOMU SAWA, MASAMI TSUCHIYA, YUKIO HORIUCHI, SHINICHI K ...
1981 Volume 34 Issue 8 Pages
980-983
Published: 1981
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An active principle inhibiting β-lactamases, which was found in the culture of a bacillus strain was a mixture of known C14-C17 fatty acids. The mixture was separated into five components by high-performance liquid chromatography. Among these components, 12-methyltetradecanoic acid showed the strongest activity (ID
50: 20-146 μM). The anteiso fatty acids having the 1-methylpropyl group exhibited an interesting activity inhibiting β-lactamases.
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THE USE OF HPLC IN BIOSYNTHETIC STUDIES OF CEPHALOSPORIN C IN THE CELL-FREE SYSTEM
R. D. MILLER, L. L. HUCKSTEP, J. P. MCDERMOTT, S. W. QUEENER, S. KUKOL ...
1981 Volume 34 Issue 8 Pages
984-993
Published: 1981
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A new cepham metabolite has been isolated from the filtered broth of
Cephalosporium acremonium by high performance liquid chromatography (HPLC) and identified as 7β-(5-Damino-adipamido)-3β-hydroxy-3α-methyl-cepham-4α-carboxylic acid (
I). Pure penicillin N was prepared using HPLC in the analytical mode. When
I was added in place of penicillin N as substrate for the cell-free biosynthetic of cephalosporin, no formation of deacetoxycephalosporin C (
II) was observed. A synthetic cepham derivative, 7β-(5-D-aminoadipamido)-3-exomethylene-cepham-4α-carboxylic acid (
III) was also tested in the cell-free system as a possible intermediate. The compound
III was shown to be an inhibitor of the ring expansion enzyme that converts penicillin N to deacetoxycephalosporin C.
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KAZUHIKO ISHIZU, SHIZUO MURATA, KIYONORI MIYOSHI, YUKIO SUGIURA, TOMOH ...
1981 Volume 34 Issue 8 Pages
994-1000
Published: 1981
Released on J-STAGE: April 12, 2006
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The 1:1 Cu(II) complexes of bleomycin (BLM) A2, BLM B2,
epi-BLM B2,
iso-BLM B2, depyruvamide-BLM A2, deglyco-BLM B2 and the structurally related peptides (P-5m, P-3A and P-3) have been comprehensively investigated by ESR and electrochemical methods. ESR spectra for Cu(II) complexes of BLM A2,
epi-BLM B2, depyruvamide-BLM A2 and P-3 revealed the axially symmetric g-anisotropies. In contrast, ESR features of the
iso-BLM B2, deglyco-BLM B2, P-5m and P-3A complexes, which lack the sixth ligation by the 3-
O-carbamoyl group of mannose, exhibited rhombic g-anisotropies with decrease of the A
// values. The cyclic voltamograms showed that all of the Cu(II) complexes underwent the well defined quasi-reversible one-electron Cu(II)/Cu(I) coupled redox reaction. The inverse of the redox potential, which measures the effective strength of the ligand field splitting, gave a linear relation with the observed g// value of each Cu(II) complex except for depyruvamide-BLM and P-3. The present results confirmed that the 3-O-carbamoyl group of the mannose moiety of the BLM molecule contributes to the stability of the metal site in BLM-Cu(II) complexes by ligation at the sixth coordination site.
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O-PROPIONYLLEUCOMYCIN A5 (TMS-19-Q)">I. SYNTHESIS AND BIOLOGICAL PROPERTIES OF 3"-O-PROPIONYLLEUCOMYCIN A5 (TMS-19-Q)
HIDEO SAKAKIBARA, OSAMU OKEKAWA, TATSURO FUJIWARA, MASARU OTANI, SATOS ...
1981 Volume 34 Issue 8 Pages
1001-1010
Published: 1981
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Using leucomycin A
5 (
1), 3"-
O-propionylleucomycin A
5 (
7) was synthesized by the following synthetic route: 2"-
O-acetylation, 3, 9-di-
O-trimethylsilylation, 3"-
O-propionylation, 3, 9-di-
O-detrimethylsilylation and 2'-
O-deacetylation. Acylation of the 3"-tertiary hydroxyl group of 2'-
O-acetyl-3, 9-di-
O-trimethylsilylleucomycin A
5 with propionyl chloride in the presence of tribenzylamine at 70°C gave a 3"-
O-propionyl derivative in 96%. yield. The structure of the final compound, 3"-
O-propionylleucomycin A
5 (
7) was confirmed by means of mass,
1H-NMR and
13C-NMR spectrometry and chemical degradations. 3"-
O-Propionylleucomycin A
5 (
7) showed higher antibacterial activity
in vitro and higher serum levels than its mother antibiotic. The biological properties of
7 also were compared with those of josamycin and midecamycin.
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O-ACYL DERIVATIVES OF LEUCOMYCIN">II. ANTIBACTERIAL ACTIVITIES AND SERUM LEVELS OF 3"-O-ACYL DERIVATIVES OF LEUCOMYCIN
HIDEO SAKAKIBARA, OSAMU OKEKAWA, TATSURO FUJIWARA, MINORU AIZAWA, SATO ...
1981 Volume 34 Issue 8 Pages
1011-1018
Published: 1981
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3"-
O-Acylation of leucomycin A5 increased its
in vitro antibacterial activity against sensitive microorganisms and also some resistant ones. An increased effect was particularly noted when an acetyl or propionyl group was introduced. On the contrary, acylation of the C-3 and C-9 hydroxyl groups reduced the antibacterial activity
in vitro. Introduction of an acyl group at the C-3" hydroxyl group increased the serum level of the compound. The increase in serum level from 3"-
O-acylation is higher than that from 3-
O-acylation. The serum level of the 3"-
O-propionyl derivative of leucomycin A5 was higher than that of the 3"-
O-acetyl derivative. 3"-
O-Propionylleucomycin A5 (5) was the derivative that showed the highest antibacterial activity and yielded the highest serum level among the derivatives examined.
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DEREK HORTON, WALDEMAR PRIEBE
1981 Volume 34 Issue 8 Pages
1019-1025
Published: 1981
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The 14-azido-, 14-thiocyanato-, 14-acetoxy-, and 14-acetylthio- derivatives of 7-
O-(3, 4-di-
O-acetyl-2, 6-dideoxy-α-L-
lyxo-hexopyranosyl)daunomycinone were synthesized by displacement reactions conducted on the corresponding 14-bromide. The
in vivo antitumor activities of the products were compared with that of the 14-hydroxyl derivative in the murine P-388 lymphocytic leukemia assay. The 14-acetoxy derivative was highly active and of low toxicity; the other products showed negligible or low activities.
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VITTORIO ARIOLI, MARISA BERTI, GIULIANA CARNITI, ELEONORA RANDISI, ELS ...
1981 Volume 34 Issue 8 Pages
1026-1032
Published: 1981
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DL 473, a new semisynthetic rifamycin, was 2-10 times more active
in vitro than rifampicin (RAMP) against several clinical isolates of
Mycobacterium tuberculosis and only slightly less active than RAMP against Gram-positive and Gram-negative bacteria. It showed excellent therapeutic activity in mice in experimental infections caused by
Staphylococcus aureus, Streptococcus pyogenes group A,
Streptococcus pneumoniae and
Klebsiella pneumoniae. In the experimental TB infection in the mouse DL 473 was clearly more active than isoniazide and RAMP, two of the most effective antitubercular drugs in current use. The LD50 in the mouse was significantly higher than that of RAMP and the half-life was about 5 times longer than that of RAMP.
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L. MARSILI, C. R. PASQUALUCCI, A. VIGEVANI, B. GIOIA, G. SCHIOPPACASSI ...
1981 Volume 34 Issue 8 Pages
1033-1038
Published: 1981
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A number of semisynthetic rifamycin derivatives modified at positions 3 and/or 4, belonging to general structures 3, 5, and 6 (see Scheme 1), have been prepared. The synthesis, structure and antimicrobial evaluation of the new compounds are described. All the derivatives have "
in vitro" antibacterial activities well comparable with that of rifampicin.
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GIANNI CHINALI
1981 Volume 34 Issue 8 Pages
1039-1045
Published: 1981
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The activities of kirromycin oxime, aurodox 2, 4-dinitrophenylhydrazone and four
O-derivatives of aurodox have been compared to those of kirromycin (mocimycin) and its natural
N-methyl analog aurodox in the
in vitro system of
E. coli. All synthetic derivatives were able to inhibit protein biosynthesis like the original antibiotics. Moreover, the analogs did promote all the effects of kirromycin on the reactions dependent on elongation factor Tu. From these results it can be concluded that the acidic hydroxyl and keto functions of kirromycin and aurodox are not directly involved in the action of the antibiotics on elongation factor Tu and can, thus, be chemically modified without loss of activity. In most cases, however, derivatization lowered the affinity of the antibiotic for elongation factor Tu. This suggests that the pyridone moiety of kirromycin and aurodox and the first part of its side chain should play a role in the association of these antibiotics with elongation factor Tu.
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RESPONSE OF ESCHERICHIA COLI AND SERRATIA MARCESCENS TO CEFMENOXIME (SCE-1365), A NEW BROADSPECTRUM CEPHALOSPORIN
MASAFUMI NAKAO, MASAHIRO KONDO, KANJI TSUCHIYA
1981 Volume 34 Issue 8 Pages
1046-1054
Published: 1981
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The morphological response of
Escherichia coli and
Serratia marcescens to cefmenoxime (SCE-1365)7, 7β-[2-(2-aminothiazol-4-yl)-(
Z)-2-methoxyiminoacetamido]-3-[(1-methyl-1
H-tetrazol-5-yl)thiomethyllceph-3-em-4-carboxylic acid, a new broad-spectrum cephalosporin, was investigated. The action of cefmenoxime was bactericidal against both
E. coil and
S. marcescens even at rather low concentrations. The pattern and the rate of the decrease of colony-forming units (CFU) were similar over a fairly wide range of concentration; this was especially noticeable in
S. marcescens. In
E. coli filamentous cells were induced at low concentrations of the cephalosporin. Spheroplasts appeared at higher concentrations, and they lysed later. A bulge was formed at the middle of the cell at concentrations near the minimal inhibitory concentration (MIC), and vacuole-like structures surrounded by membrane were also observed in the cytoplasm of the filamentous cells. In
S. marcescens filamentation of cells occurred over a considerable range of concentration. With longer times of incubation, granular structures and fused nuclear regions were noticed in the sparse cytoplasm.
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IWAO YAMAZAKI, YOSHIHIRO SHIRAKAWA, TAKESHI FUGONO
1981 Volume 34 Issue 8 Pages
1055-1063
Published: 1981
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The renal excretory mechanism of cefmenoxime was compared with those of 6 other cephalosporins (cefotaxime, deacetylcefotaxime, cefotiam, cefazolin, cephaloridine and cefsulodin) in rats and rabbits. In rats, renal clearance (C
f-Drug: corrected for serum protein binding) of cefmenoxime (4.06 ml/minute) was lower than that of cefazolin, similar to that of cefotiam, and higher than those of cefotaxime, deacetylcefotaxime, cephaloridine, and cefsulodin. In rabbits, the value for cefmenoxime (2, 519 ml/minute) was markedly higher than those for the other drugs. If the clearance ratio (C
f-Drug/C
Inulin=CRf) is more than unity, tubular secretion of a drug is indicated. In rats, the tubular secretion of cefmenoxime equalled the glomerular filtration (CRf=2.17). The tubular secretion of cefmenoxime was lower than that of cefazolin but similar to that of cefotiam. None of the other cephalosporins seemed to be secreted significantly. In rabbits, a large amount of cefmenoxime was secreted (CRf-208). The tubular secretion was larger than those of the other cephalosporins. All the drugs except cefsulodin showed significant tubular secretion.
A species difference was observed in the CRf of the cephalosporins: the values were generally higher in rabbits than in rats.
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YOSHIKAZU SUGIMOTO, TOSHIO NISHIMURA, HIDEO SUZUKI, NOBUO TANAKA
1981 Volume 34 Issue 8 Pages
1064-1066
Published: 1981
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GÜNTER LAZAR, HANS ZÄHNER, SABINE BREIDING, MANFRED DAMBERG, ...
1981 Volume 34 Issue 8 Pages
1067-1068
Published: 1981
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HISAYOSHI NAKAZAWA, SUSUMU HORIKAWA, HIROSHI OGAWARA
1981 Volume 34 Issue 8 Pages
1070-1072
Published: 1981
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TSUYOSHI KIHARA, HIROO KUSAKABE, GOTO NAKAMURA, TOSIO SAKURAI, KIYOSHI ...
1981 Volume 34 Issue 8 Pages
1073-1074
Published: 1981
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ISOLATION AND STRUCTURES OF NEW 16-MEMBERED AGLYCONES, MYCINOLIDE IV AND PROTOMYCINOLIDE IV
MITSUO HAYASHI, HIROKO OHARA, MASARU OHNO, HIDEO SAKAKIBARA, SHUZO SAT ...
1981 Volume 34 Issue 8 Pages
1075-1077
Published: 1981
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D. O. SPRY, R. D. MILLER, L. L. HUCKSTEP, N. NEUSS, S. KUKOLJA
1981 Volume 34 Issue 8 Pages
1078-1079
Published: 1981
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