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ISOLATION, CHARACTERIZATION, STRUCTURE AND BIOLOGICAL PROPERTIES
HANNELORE DRAUTZ, PETER REUSCHENBACH, HANS ZÄHNER, JÜRGEN RO ...
1985 Volume 38 Issue 10 Pages
1291-1301
Published: 1985
Released on J-STAGE: April 19, 2006
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Elloramycin (1), a new antibiotic produced by
Streptomyces olivaceus strain TÜ 2353, was detected by chemical screening. The dark yellow compound, molecular formula C
32H
36O
15, is weakly active against a variety of Gram-positive bacteria, especially streptomycetes and against stem cells of L-1210 leukemia. Acidic hydrolysis of the antibiotic liberated elloramycinone (3) as aglycone and 2, 3, 4-tri-
O-methyl-L-rhamnose, which was identified as methyl glycoside 5b. The structure of elloramycin was established by comparison of the spectra (UV,
1H NMR,
13C NMR) with those of the known tetracenomycin C (2), 3 and the fact that 2 and 3 gave the same tetramethyl ether after permethylation. Elloramycin is an anthracycline-like antibiotic, the aglycone resembles tetracenomycin C, the sugar is connected in a phenolic α-glycosidic linkage.
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I. PRODUCTION, ISOLATION AND PROPERTIES
MITSUAKI TSUNAKAWA, MINORU HANADA, HIROSHI TSUKIURA, KOJI TOMITA, KOZO ...
1985 Volume 38 Issue 10 Pages
1302-1312
Published: 1985
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A strain of
Streptomyces hygroscopicus No. J296-21 (ATCC 39150) was found to produce a complex of new antibiotics, called inosamycins, which consisted of components A, B, C, D and E. They are novel aminocyclitol antibiotics structurally related to neomycin, paromomycin and ribostamycin. The antibiotic complex and each component of inosamycin exhibit a broad antibacterial spectrum but they are inactive against most of the aminoglycoside-resistant organisms. The antibacterial activity of inosamycin A, the major component of the complex, is comparable to that of neomycin but its acute toxicity is significantly lower (
ca. 1/3) than that of neomycin.
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II. STRUCTURE DETERMINATION
MITSUAKI TSUNAKAWA, MINORU HANADA, HIROSHI TSUKIURA, MASATAKA KONISHI, ...
1985 Volume 38 Issue 10 Pages
1313-1321
Published: 1985
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Structures of the new aminocyclitol antibiotics, inosamycins A, B, C, D and E, have been determined by a combination of chemical degradation and spectroscopic studies. They are structurally related to neomycin, paromomycin and ribostamycin but differ in that all the inosamycin components contain 2-deoxy-
scyllo-inosamine in place of 2-deoxystreptamine in the known aminoglycoside antibiotics.
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SATOSHI OMURA, RIMIKO IWATA, YUZURU IWAI, SEIKO TAGA, YOSHITAKE TANAKA ...
1985 Volume 38 Issue 10 Pages
1322-1326
Published: 1985
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A new antibiotic, luminamicin, was isolated from the culture broth of an actinomycete strain OMR-59. It exhibits antibacterial activity against anaerobic bacteria, especially against
Clostridium sp. The molecular formula of the antibiotic was determined as C
32H
38O
12 on the basis of high resolution mass spectrum, elemental analysis and NMR spectrum.
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I. TAXONOMY, ISOLATION AND BIOLOGICAL ACTIVITY
NOBUO TANAKA, TAKAYOSHI OKABE, FUJIO ISONO, MASAMI KASHIWAGI, KUNIKO N ...
1985 Volume 38 Issue 10 Pages
1327-1332
Published: 1985
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Lactoquinomycin, a novel basic antibiotic, was isolated from the culture broth of a soil streptomyces by repeated solvent extraction and adsorption column chromatography. Morphological, cultural and physiological studies revealed that the organism belongs to the species
Streptomyces tanashiensis. The antibiotic was active against bacteria, particularly Gram-positive organisms, and neoplastic cells
in vitro. Antibiotic-resistant cell sublines of L5178Y lymphoblastoma were more significantly inhibited by lactoquinomycin than the parental cell line. Lactoquinomycin was effective against Ehrlich carcinoma in mice.
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II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE ASSIGNMENT
TAKAYOSHI OKABE, KUNIKO NOMOTO, HIROSHI FUNABASHI, SHIGENOBU OKUDA, HI ...
1985 Volume 38 Issue 10 Pages
1333-1336
Published: 1985
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Lactoquinomycin, a new antibiotic, C
24H
27NO
8, mp 151-159°C (dec), FAB-MS:
m/z 458 (MH
+), is a basic substance, showing UV λ
MeOHmax (ε) 215 (37, 600), 254 (10, 700) and 432nm (4, 760), and IR νCHCl
3max (γ-lactone), 1665 and 1650 (quinone) cm
-1. The structure of lactoquinomycin has been elucidated by
-1H NMR and ORD in comparison with those of kalafungin.
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J. B. TUNAC, B. D. GRAHAM, S. W. MAMBER, W. E. DOBSON, M. D. LENZINI
1985 Volume 38 Issue 10 Pages
1337-1343
Published: 1985
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Four novel antitumor antibiotics (PD 114, 759, PD 115, 028, PD 119, 707, and PD 119, 193) are produced as a complex by a new species of
Actinomadura. The proposed name for the culture is
Actinomadura verrucosospora subsp. veractimyces ATCC 39363. The antibiotics are extremely bioactive, with MIC values of <0.006ng/ml against several bacteria and ID
50 values of 0.003-0.107ng/ml against L1210 leukemia cells
in vitro. Antitumor activities vs. P388 leukemia
in vivo were observed at doses of 0.313, 0.40, and 0.5μg/kg (daily×5) for PD 119, 707, PD 115, 028, and PD 114, 759, respectively.
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J. B. TUNAC, M. UNDERHILL
1985 Volume 38 Issue 10 Pages
1344-1349
Published: 1985
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2'-Chloropentostatin (2-CP) is a new nucleoside antibiotic produced by
Actinomadura sp. ATCC 39365. A selectively sensitive assay organism,
Enterococcus faecalis PD 05045 (MIC 0.005μg/ml) was instrumental in the discovery of this compound. 2-CP is a tight-binding inhibitor of adenosine deaminase (
Ki=1.1×10
-10M).
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O-ACYL- 4"-O-SULFONYL AND 3, 3"-DI-O-ACYL-4"-O-ALKYL DERIVATIVES OF SPIRAMYCIN I">VI. SYNTHESIS AND ANTIBACTERIAL ACTIVITIES OF 3, 3"-DI-O-ACYL- 4"-O-SULFONYL AND 3, 3"-DI-O-ACYL-4"-O-ALKYL DERIVATIVES OF SPIRAMYCIN I
HIROSHI SANO, TOSHIAKI SUNAZUKA, HARUO TANAKA, KINYA YAMASHITA, RYO OK ...
1985 Volume 38 Issue 10 Pages
1350-1358
Published: 1985
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3, 3"-Di-
O-acyl-4"-
O-sulfonyl and 3, 3"-di-
O-acyl-4"-
O-alkyl derivatives of spiramycin I were synthesized and evaluated by four parameters, antibacterial activity, affinity to ribosomes, lypophilicity and therapeutic effects. Among them, 3, 3"-di-
O-acetyl-4"-
O-mesyl and 3, 3"-di-
O-acetyl-4"-
O-methylspiramycin I having relatively small substituents at 4"-position were the most effective in mouse protection tests, and the results were comparable to acetylspiramycin.
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3. SYNTHESIS AND ACTIVITY OF 21-EPI-RIFAMYCIN S
M. BRUFANI, L. CELLAI, L. COZZELLA, M. FEDERICI
1985 Volume 38 Issue 10 Pages
1359-1362
Published: 1985
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Rifamycins inhibit bacterial DNA-dependent RNA polymerase through the formation of non-covalent bonds by the oxygenated groups at C(1), C(8), C(21), and C(23). These must be unhindered and underivatized, with the antibiotic in a proper overall molecular conformation. The present study shows that contrary to previous conclusions the availability of the hydroxyl group at C(21) is not as important as that of the other three groups. In support of this is the observation that 21-
epi-rifamycin S is partially active, both on the isolated DNA-dependent RNA polymerase and on some Gram-positive bacterial strains.
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KAZUTOH TAKESAKO, TERUHIKO BEPPU, TERUYA NAKAMURA, AKIRA OBAYASHI
1985 Volume 38 Issue 10 Pages
1363-1370
Published: 1985
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Guanidylfungin A was chemically modified by alkylation, reduction and/or demalonylation. Demalonylmethylguanidylfungin A became soluble in water and showed approximately eight-fold higher activity against fungi and Gram-positive bacteria than guanidylfungin A along with strongly fungicidal effect. Similarly, copiamycin was converted to demalonylmethylcopiamycin, which also showed higher antifungal activity than copiamycin itself.
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GERHARD EMMER, PETER KNEUSSEL, JOHANNES HILDEBRANDT, FRIEDERIKE TURNOW ...
1985 Volume 38 Issue 10 Pages
1371-1386
Published: 1985
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New penem derivatives with various substituted, enantiomerically pure pyrrolidine-thio side chains at the C-2 position were synthesized and their chemotherapeutic potentials assessed in comparison with Sch 29482. The following criteria were used for preliminary evaluation : Antibacterial activity
in vitro, β-lactamase inhibition and apparent hydrolysis rates by crude murine and human kidney enzyme preparations. The most active compounds, 16e, 16f and 18 exhibit properties typical of this substance class with a tendency towards greater antibacterial potency in comparison with Sch 29482, especially against
Pseudomonas aeruginosa. No clear-cut structure-activity relationships could be found with respect to β-lactamase inhibition and stability against degrading renal enzymes.
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NORIYOSHI NOGUCHI, HIROTOMO MASUYA, TOHORU SUGAWARA, YASUHIKO KAWANO, ...
1985 Volume 38 Issue 10 Pages
1387-1400
Published: 1985
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The synthesis and antibacterial activity of 3-[(
Z)-2-alkoxyimino-2-(2-aminothiazol-4-yl)-acetamido]-2-azetidinone-1-sulfonic acid derivatives with a heteroatom-bound substituent at the 4-position are described. The effect of various 4-substituents on the antibacterial activity was examined. Some of these compounds showed excellent antibacterial activity especially against Gram-negative bacteria, including β-lactamase-producing strains.
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DEBORAH A. STEINBERG, GAIL A. PETERSON, RICHARD J. WHITE, WILLIAM M. M ...
1985 Volume 38 Issue 10 Pages
1401-1407
Published: 1985
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The stimulation of bioluminescence in
Photobacterium leiognathi has previously been described as a test for genotoxic compounds. An adaptation of this procedure has been developed which uses a dim variant of
P. leiognathi and permits the prescreening of microbial fermentation broths for potential antitumor agents. Bioluminescence in this organism was stimulated by compounds which bind to DNA or affect DNA synthesis. Antibiotics with target sites such as protein, cell wall or RNA synthesis, did not alter bioluminescence. Fermentation broths from over 5, 000 soil isolates were prescreened in this assay and 95 (1.6%) were defined as active. Further analysis of selected cultures suggested that about half produced compound(s) with DNA-binding activity. These results suggest that the photobacterium induction assay (PIA) may be useful as a prescreen for potential antitumor agents. The assay is rapid, simple and requires only microgram quantities of material for testing.
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YOSHIYUKI MATSUSHITA, HIROYUKI KUMAGAI, AKIHIRO YOSHIMOTO, HIROSHI TON ...
1985 Volume 38 Issue 10 Pages
1408-1419
Published: 1985
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(2"R)-4'-
O-Tetrahydropyranyladriamycin (THP) is a new derivative of doxorubicin (adriamycin, ADM). The concentrations of THP and ADM required to inhibit by 50% the growth of a cultured L1210 cells was 0.003μg/ml and 0.016μg/ml, respectively. Various therapeutic designs of combinations of THP with other antitumor agents were investigated
in viva using the L1210 murine leukemia. The combination of THP with cytosine arabinoside (Ara-C), cyclocytidine hydrochloride (Cyclo-C), 6-mercaptopurine (6-MP) and cyclophosphamide (EX) showed a great effectiveness following daily intraperitoneal treatment from days I to 10. High therapeutic effects were also obtained with the combinations of THP with Ara-C, Cyclo-C, vincristine (VCR) and EX following intravenous combination therapy one day following implantation of L1210 leukemia. Schedule dependency and its therapeutic efficacy of THP were examined. THP showed almost the same antitumor activity on the solid-type sarcoma-180 or solid-type Ehrlich carcinoma as ADM by intraperitoneal or intravenous treatment. THP showed some superior activity to ADM in the advanced stage of L1210 leukemia. High antitumor activity of THP on murine leukemia L1210 has been reported by TSURUO
et al. (Cancer Res. 42 : 1462-1467, 1982) and was also confirmed. THP gave many mice cures, especially in the intravenous treatment.
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ARUN KUMAR, MAHAK SINGH, V. S. CHAUHAN
1985 Volume 38 Issue 10 Pages
1420-1422
Published: 1985
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G. C. S. REDDY, R. SAHAI, H. W. FEHLHABER, B. N. GANGULI
1985 Volume 38 Issue 10 Pages
1423-1425
Published: 1985
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A. L. LABORDE, J. I. CIALDELLA, J. A. Fox, V. P. MARSHALL
1985 Volume 38 Issue 10 Pages
1426-1428
Published: 1985
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I. ANTIMICROBIAL AND CYTOCIDAL ACTIVITIES
YOSHIO INOUYE, HIROMASA OKADA, SWAPAN KUMAR ROY, TADAYO MIYASAKA, SATO ...
1985 Volume 38 Issue 10 Pages
1429-1432
Published: 1985
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XXVIII MOYUKAMYCIN, A NEW GLYCOSYLATED POLYETHER ANTIBIOTIC
HIROSHI NAKAYAMA, HARUO SETO, NOBORU OTAKE, MICHIKO YAMAGISHI, AKIRA K ...
1985 Volume 38 Issue 10 Pages
1433-1436
Published: 1985
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MASAJI SEZAKI, TORU SASAKI, TADASHI NAKAZAWA, UETO TAKEDA, MICHIAKI IW ...
1985 Volume 38 Issue 10 Pages
1437-1439
Published: 1985
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MASAHIRO NISHII, JIN-ICHIRO INAGAKI, FUJIO NOHARA, KIYOSHI ISONO, HIRO ...
1985 Volume 38 Issue 10 Pages
1440-1443
Published: 1985
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JUNG J. LEE, TOM S.S. CHEN, CHING-JER CHANG, CATHERINE FENSELAU, HEINZ ...
1985 Volume 38 Issue 10 Pages
1444-1446
Published: 1985
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SATOSHI OMURA, KAZUO TSUZUKI, YUZURU IWAI, MASANORI KISHI, SHIRO WATAN ...
1985 Volume 38 Issue 10 Pages
1447-1448
Published: 1985
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