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I. TAXONOMY, FERMENTATION AND BIOLOGICAL PROPERTIES
J. B. TUNAC, B. D. GRAHAM, W. E. DOBSON
1983 Volume 36 Issue 12 Pages
1595-1600
Published: 1983
Released on J-STAGE: April 12, 2006
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CI-920 (PD 110, 161) and two analogues (PD 113, 270 and PD 113, 271) are novel antitumor compounds produced by a new actinomycete characterized as
Streptomyces pulveraceus subsp.
fostreus ATCC 31906. The antitumor compounds are predominantly produced during the stationary (idiophase) growth phase of the organism. CI-920 is active
versus the murine P388 lymphocytic and L1210 lymphoid leukemia with T/C values of 246 and 207, respectively. This compound has no significant antimicrobial activity.
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II. ISOLATION AND CHARACTERIZATION
S. S. STAMPWALA, R. H. BUNGE, T. R. HURLEY, N. E. WILLMER, A. J. BRANK ...
1983 Volume 36 Issue 12 Pages
1601-1605
Published: 1983
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A complex of structurally related compounds that exhibit
in vivo antileukemic activity was isolated from fermentation broths of a new streptomycete. The components of this complex are water soluble phosphate esters containing a conjugated triene system. The isolation and characterization of three of these components are described.
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I. SEPARATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES OF LEUCINOSTATINS A AND B
KAZUTAKA FUKUSHIMA, TADASHI ARAI, YUJI MORI, MAKOTO TSUBOI, MAKOTO SUZ ...
1983 Volume 36 Issue 12 Pages
1606-1612
Published: 1983
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Leucinostatin, a peptide antibiotic, was separated by silica gel and alumina column chromatography into two related components designated as leucinostatin A hydrochloride (C
61H
111N
11O
13•HCl) and leucinostatin B hydrochloride (C
61H
109N
11O
13•HCl). Physico-chemical as well as biological properties of the two separated components were analyzed. These properties pointed to closely resembling chemical structures.
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II. THE STRUCTURES OF LEUCINOSTATINS A AND B
KAZUTAKA FUKUSHIMA, TADASHI ARAI, YUJI MORI, MAKOTO TSUBOI, MAKOTO SUZ ...
1983 Volume 36 Issue 12 Pages
1613-1630
Published: 1983
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Structures
I and
II have been assigned to leucinostatins A and B based on fast atom bombardment, secondary ion, field desorption and chemical ionization mass spectrometry, NMR studies and chemical degradation methods of the intact antibiotics and their acid hydrolysis products.
The essential difference between leucinostatins A and B is concluded to be the replacement of (2
S)-
N1,
N1-dimethylpropane-1, 2-diaminein leucinostatin A by (2
S)-
N1-methylpropane-1, 2-diamine in leucinostatin B. This was further confirmed from the evidence that methylation with methyl iodide led each antibiotic to the identical compound which was named leucinostatin A-M (
III).
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S. J. BOX, M. L. GILPIN, M. GWYNN, G. HANSCOMB, S. R. SPEAR, A. G. BRO ...
1983 Volume 36 Issue 12 Pages
1631-1637
Published: 1983
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A new antibiotic designated MM 14201 has been detected in a culture of
Streptomyces sp. NCIB 11813. Methods for the production and purification of MM 14201 are described. Biological evaluation has shown it has broad spectrum antibacterial activity being most effective against
Serratia and
Pseudomonas sp. Structural studies are reported which have demonstrated MM 14201 is a new epoxyquinone derivative.
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SCREENING, FERMENTATION, ISOLATION, STRUCTURE AND BIOLOGICAL ACTIVITY
SHIGEYOSHI MIYASHIRO, TOSHIHIKO ANDO, KAZUO HIRAYAMA, TAKAO KIDA, HIRO ...
1983 Volume 36 Issue 12 Pages
1638-1643
Published: 1983
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Two streptothricin-group antibiotics, AN-201 I and II, were newly discovered and isolated from the culture broth of
Streptomyces nojiriensis C-13. These antibiotics were purified by IRC-50 (H
+) and CM-Sephadex C-50 chromatography, and paper electrophoresis. Structural analysis of AN-201 I and II showed that they were N
β-acetylated derivatives of streptothricin E and D, respectively. They had antibacterial activities against several strains of
Escherichia coli, Bacillus subtilis, Micrococcus luteus and
Staphylococcus aureus, and showed a strong selective cytotoxic effect on 3T3 cells transformed with SV-40 as compared with their normal cells in a test system
in vitro as well as
in vivo.
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KURUMI ISHIMARU, JUNKO ISHIDA, NORIKO NOBORIO, SHOSHIRO NAKAMURA
1983 Volume 36 Issue 12 Pages
1644-1650
Published: 1983
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A new antifungal antibiotic named histidinomycin was isolated from the broth filtrate of a streptomycete, tentatively designated as isolate H 878-MY 1. Histidinomycin was purified as the monohydrochloride and the molecular formula was proposed to be C
22H
30N
8O
11•HCl. The antibiotic gave histidine by acid hydrolysis. Histidinomycin showed rather narrow antimicrobial spectrum for only few genera of phytophathogenic fungi.
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H. IRSCHIK, K. GERTH, G. HÖFLE, W. KOHL, H. REICHENBACH
1983 Volume 36 Issue 12 Pages
1651-1658
Published: 1983
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From the culture supernatant of the myxobacterium,
Myxococcus fulvus strain Mx f50, an antibiotic activity was isolated which blocked growth of many Gram-positive and several Gram-negative bacteria, but not of yeasts and fungi. The activity consisted of two closely related compounds, myxopyronins A and B. The myxopyronins appear to be new antibiotics, and seem to specifically inhibit bacterial RNA polymerase.
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M. J. PERRY, A. HENDRICKS-GITTINS, L. M. STACEY, M. W. ADLARD, W. C. N ...
1983 Volume 36 Issue 12 Pages
1659-1663
Published: 1983
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Isolates of
Microsporum canis, Microsporum gypseum and
Epidermophyton floccosum were observed to produce antibacterial activities under cross-resistance to fusidic acid. The activity from
E. floccosum was shown to be due to fusidic acid, diketofusidic acid and 3-ketofusidic acid. Possible contributions of these antibiotics to microbial interaction during dermatophytosis is discussed.
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ALEX CORNISH, MICHAEL J. WARING, ROBERT D. NOLAN
1983 Volume 36 Issue 12 Pages
1664-1670
Published: 1983
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Protoplasts of
Streptomyces echinatus have been used to investigate the biosynthesis of echinomycin (quinomycin A). It has been shown that this organism has the capacity to convert a series of triostins to the corresponding quinomycins by a mechanism involving methylation. Evidence is presented which suggests that triostin A is the natural precursor of echinomycin. Conversion of tetra-
N-demethyl analogues of triostin A to corresponding analogues of echinomycin was not detected.
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W. J. MCGAHREN, R. A. LEESE, F. BARBATSCHI, G. O. MORTON, N. A. KUCK, ...
1983 Volume 36 Issue 12 Pages
1671-1682
Published: 1983
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The isolation and characterization of many of the components of the avoparcin complex are described. A number of mild degradations products from this complex are similarly treated. Conditions for the analytical and preparative HPLC resolution of these materials are outlined.
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G. A. ELLESTAD, W. SWENSON, W. J. MCGAHREN
1983 Volume 36 Issue 12 Pages
1683-1690
Published: 1983
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The epimerization of avoparcin entities is discussed in some detail. The absolute stereochemistry of avoparcin is now known since the
N-methyl terminal amino acid of the aglycone has been isolated and shown to exhibit negative optical rotation and hence has the
R-configuration. The same amino acid has been isolated from an epimerized solution of avoparcin and found to have positive rotation and hence the
S-configuration. A comparison is made of the CD curves of β-avoparcin and
epi-β-avoparcin. Some discussion on the effect of protonation of the terminal
N-methyl group on the antibacterial activity of avoparcin is included.
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F. SZTARICSKAI, J. BORDA, M. M. PUSKÁS, R. BOGNÁR
1983 Volume 36 Issue 12 Pages
1691-1698
Published: 1983
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Comparative HPLC examination of seven antibiotics of vancomycin type has been undertaken. Investigation has shown that on column I in eluent system B, ristomycin A (ristocetin A) can be not only separated from vancomycin, but both antibiotics can be quantitatively determined. Under these conditions the lowest detectable quantities of the individual antibiotics have been also stated. By the application of this column and eluent system A, ristomycin A (ristocetin A) and the major component of the A-35512 B antibiotic complex can be readily separated from one-another and from avoparcin α and β.
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III. SYNTHESES AND ANTITUMOR ACTIVITY OF TOMAYMYCIN ANALOGS
ZENZABURO TOZUKA, HISATOYO YAZAWA, MASAYOSHI MURATA, TAKAO TAKAYA
1983 Volume 36 Issue 12 Pages
1699-1708
Published: 1983
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The syntheses and antitumor activity of tomaymycin analogs are described. Structural modification of such parts of tomaymycin as the ethylidenepyrrole ring, aminal bond, and substituents of the benzene ring are discussed.
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SATOSHI OMURA, JUNJI INOKOSHI, HAJIME MATSUBARA, HARUO TANAKA
1983 Volume 36 Issue 12 Pages
1709-1712
Published: 1983
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Structure-activity relationships of tylosin and related compounds were evaluated in terms of their antimicrobial and ribosome-binding activities. Demycarosyl derivatives, demycarosyltylosin and 20-deoxydemycarosylrelomycin, were slightly weaker than tylosin and 20-deoxyrelomycin, respectively, both in antimicrobial activity and in affinity to ribosomes. The corresponding demycarosyl-demycinosyl derivatives had weaker antimicrobial activities despite their relatively high affinities to ribosomes. A 23-deoxy-demycarosyl-demycinosyl derivative, 20-oxo-5-
O-mycaminosylprotylonolide, had a higher affinity to ribosomes than that of tylosin and was equivalent to tylosin in antimicrobial activity against Gram-positive bacteria. These results suggest that the mycinose moiety increases the ability of the molecule to enter bacterial cells. Among the derivatives tested, a 23-iodo derivative, 20-deoxy-23-iodo-5-
O-mycarosyltylonolide, had the highest affinity for ribosomes as well as the highest antimicrobial activity.
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HAJIME MATSUBARA, JUNJI INOKOSHI, AKIRA NAKAGAWA, HARUO TANAKA, SATOSH ...
1983 Volume 36 Issue 12 Pages
1713-1721
Published: 1983
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Reductive aminations of the aldehyde group at C-20 position of tylosin and demycarosyltylosin (desmycosin) were carried out using primary and secondary amines in the presence of sodium cyanoborohydride. Some of these derivatives brought about higher antimicrobial and ribosome-binding activities, and the structure-activity relationship is discussed.
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MASARU UYEDA, KUNIHIKO KUBOTA, SHIGEYUKI MIYAMURA, MOTOO SHIBATA
1983 Volume 36 Issue 12 Pages
1722-1728
Published: 1983
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Two transformation products of maridomycin (MDM) III, MDM-S
1 and MDM-S
2 named after
Serratia marcescens, were isolated by silica gel chromatography. NMR and IR analysis revealed that MDM-S
1 and -S
2 had no aldehyde group at C-18 on the macrolactone ring, and that the hydroxyl group at C-9 seemed to disappear. Although MDM-S
1 and -S
2 are less active against Gram-positive bacteria than starting MDM III. they are interesting materials in view of the introduction of nitrogen into each molecule, and that the transformation products are produced by Gram-negative bacteria which are thought to be insensitive to macrolide antibiotics.
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TAKESHI YAMADA, TAKAHISA YAMANOUCHI, YASUKO ONO, AKIHISA NAGATA, TATEA ...
1983 Volume 36 Issue 12 Pages
1729-1734
Published: 1983
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Palmitoyltuberactinamine N (Pal-Tua N) and di-β-lysylcapreomycin IIA (di-β-Lys-Cpm IIA), which are synthetic derivatives of the antituberculous agent tuberactinomycin (Tum) and capreomycin (Cpm) respectively, were tested for anti-bacterial activity. Pal-Tua N inhibited not only tuberactinomycin-resistant
Mycobacterium smegmatis but also
Escherichia coli, Corynebacterium diphtheriae, Staphylococcus aureus, Streptococcus pyogenes, although it has lost activity against
Mycobacterium tuberculosis. Di-β-Lys-Cpm IIA inhibited the growth of laboratory-derived Tum-resistant
M. smegmatis and
M. tuberculosis as well as Tum-resistant
M. tuberculosis from patients with one exceptional case.
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KARL-HEINZ VAN PÉE, OLGA SALCHER, PETER FISCHER, MICHAEL BOKEL, ...
1983 Volume 36 Issue 12 Pages
1735-1742
Published: 1983
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The mutant strain ACN of
Pseudoinonas aureofaciens ATCC 15926 produces several bromo derivatives of pyrrolnitrin. Five brominated amino- and three brominated nitrophenyl pyrrole compounds could be isolated, and their structures were established by
1H NMR, UV and mass spectroscopy. The isolated amino compounds showed no biological activity; the nitro derivatives inhibited the growth of
Neurospora crassa ATCC 9276, though not as effective as pyrrolnitrin itself. 2-Carboxy-4-(2-amino-3-bromophenyl)pyrrole (X) is demonstrated to be an intermediate in the biosynthesis of brominated pyrrolnitrin; the biosynthetic pathway to bromo derivatives of pyrrolnitrin is discussed.
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KATSUO TAKEDA, KAZUE KAWAGUCHI, MASANORI OKANISHI
1983 Volume 36 Issue 12 Pages
1743-1747
Published: 1983
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Three plasmids, pSCY 2, pSCY 3 and pSCY 4, were detected in
Streptomyces noursei B3, a producer of cycloheximide and nystatin. pSCY 3 and pSCY 4 had molecular sizes of 15.1 megadaltons (Md) and 3.2 Md, respectively. When covalently closed circular (ccc) DNAs were extracted from the mycelia during the course of cultivation, the yield of ccc DNA extracted per mycelium reached the highest value at the starting point of the exponential growth phase and decreased rapidly during exponential phase; the yield increased gradually in stationary phase. The smallest plasmid, pSCY 4, could not be detected after 42 hours of cultivation. To purify and characterize DNA of the major plasmid pSCY 3, it was cloned into
Escherichia coli using pACYC 184 as a vector, and the physical maps of the composite plasmids were constructed.
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KUNIMOTO HOTTA, ATSUSHI TAKAHASHI, NORIKO SAITO, YOSHIRO OKAMI, HAMAO ...
1983 Volume 36 Issue 12 Pages
1748-1754
Published: 1983
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Actinomycetes were characterized in terms of resistance to 11 different aminoglycoside antibiotics (AGs). Strains freshly isolated in AG containing media showed wide varieties of multiple AG resistance, while the majority of ISP (International Streptomyces Project) cultures and the actinomycete strains isolated in an AG free medium were susceptible to all or most of the AGs tested. Marked characteristics were noted in multiple AG resistance of gray and yellow colored actinomycetes and AG-producing strains. In gray colored isolates, multiple resistance to kanamycin A, dibekacin, ribostamycin, butirosin A, istamycin A and neamine was often observed. Yellow colored isolates having multiple AG resistance were mostly resistant to neamine, ribostamycin and streptomycin and, to a lesser extent, istamycin A, dibekacin and butirosin A. Most of the AG producers tested showed unique multiple AG resistance patterns.
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SATOSHI OMURA, KAZUHIKO OTOGURO, HARUO TANAKA
1983 Volume 36 Issue 12 Pages
1755-1761
Published: 1983
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The mode of action of virustomycin A, a novel 18-membered acrolide, on
Trichomonas Foetus was investigated. The antibiotic inhibited the biosynthesis of RNA, DNA and protein in the organism. The inhibition of RNA biosynthesis was the most severe. Virustomycin A repressed the incorporation of [
3H]uridine into both acid-soluble and insoluble fractions, whereas actinomycin D inhibited the incorporation of [
3H]uridine into acid-insoluble fraction alone. Furthermore, it was found that virustomycin A interfered with nucleotide formation from uridine and adenosine but not with their transport to the cells. On the other hand, the antibiotic did not inhibit the activities of uridine kinase and uracil phosphoribosyltransferase in a cell-free extract from the organism. These data suggest that the antibiotic interferes with the formation of phosphate donor(s)(possibly ATP-forming system)of the organism.
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HUGO PEETERS, RAINER ZOCHER, NORBERT MADRY, PETER B. OELRICHS, HORST K ...
1983 Volume 36 Issue 12 Pages
1762-1766
Published: 1983
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The enzymatic formation of the cyclodepsipeptide beauvericin was demonstrated in cell-free extracts from
Beauveria bassiana. In analogy to the enniatin synthetase system formation of beauvericin is strictly dependent on the presence of the constituent amino and hydroxy acid,
S-adenosylmethionine, and ATP/Mg
2+. Synthesizing activity could be enriched about 12-fold by fractional ammonium sulfate precipitation. Besides the enniatin synthetase system this represents another example of the cell-free synthesis of a depsipeptide from eucaryotic origin.
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MILTON J. ZMIJEWSKI Jr., MARCIA J. MIKOLAJCZAK
1983 Volume 36 Issue 12 Pages
1767-1769
Published: 1983
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KARTAR SINGH, S. N. SEHGAL, S. RAKHIT, CLAUDE VÉZINA
1983 Volume 36 Issue 12 Pages
1770-1773
Published: 1983
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MICHIO YAMASHITA, SEIJI HASHIMOTO, MASAMI EZAKI, MORITA IWAMI, TADAAKI ...
1983 Volume 36 Issue 12 Pages
1774-1776
Published: 1983
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TSUYOSHI KIHARA, KIMIE KOBINATA, HIROO KUSAKABE, KIYOSHI ISONO
1983 Volume 36 Issue 12 Pages
1777-1780
Published: 1983
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SATOSHI OMURA, AKIRA NAKAGAWA, RIMIKO IWATA, AKIKO HATANO
1983 Volume 36 Issue 12 Pages
1781-1782
Published: 1983
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SATOSHI OMURA, NOBUTAKA IMAMURA, KIYOIZUMI HINOTOZAWA, KAZUHIKO OTOGUR ...
1983 Volume 36 Issue 12 Pages
1783-1786
Published: 1983
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HAMAO UMEZAWA, TAKESHI NAKAMURA, SHUNZO FUKATSU, TAKAAKI AOYAGI, KUNIA ...
1983 Volume 36 Issue 12 Pages
1787-1788
Published: 1983
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KUNIMOTO HOTTA, ATSUSHI TAKAHASHI, YOSHIRO OKAMI, HAMAO UMEZAWA
1983 Volume 36 Issue 12 Pages
1789-1791
Published: 1983
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SATOSHI OMURA, YOSHITAKE TANAKA, HIROSHI MAMADA, ROKURO MASUMA
1983 Volume 36 Issue 12 Pages
1792-1794
Published: 1983
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