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I. TAXONOMY, PRODUCTION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
TAKAAKI AOYAGI, TAKAYUKI AOYAMA, FUKIKO KOJIMA, NAOKO MATSUDA, MASATO ...
1992 Volume 45 Issue 9 Pages
1385-1390
Published: September 25, 1992
Released on J-STAGE: April 19, 2006
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Benastatins have been isolated as part of a program designed to find microorganism-produced inhibitors of glutathione S-transferase from
Streptomyces sp. MI384-DF12. They were purified by chromatography of reversed-phase silica gel, silica gel and Capcell Pak C
18 (HPLC) followed by solvent extraction and then isolated as yellow powders. Benastatins A and B have the molecular formulae, C
30H
28O
7 and C
30H
30O
7, respectively. They were competitive with 3, 4-dichloronitrobenzene as the substrate, and the inhibition constants (
Ki) of benastatins A and B were 5.0 × 10
-6 and 3.7 × 10
-6, respectively.
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II. STRUCTURE DETERMINATION OF BENASTATINS A AND B
TAKAYUKI AOYAMA, HIROSHI NAGANAWA, YASUHIKO MURAOKA, HIKARU NAKAMURA, ...
1992 Volume 45 Issue 9 Pages
1391-1396
Published: September 25, 1992
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Benastatins A and B, new inhibitors of glutathione
S-transferase, have been isolated from the culture broth of
Streptomyces sp. MI384-DF12. By X-ray crystallography, benastatin A was determined to be 8, 13-dihydro-1, 7, 9, 11-tetrahydroxy-13-dimethyl-8-oxo-3-pentyl-benzo[
a]naphthacene-2-carboxylic acid. The structure of benastatin B was elucidated by NMR studies.
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PRODUCING ORGANISM, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL AND IN VITRO BIOLOGICAL PROPERTIES
Y. K. T. LAM, C. F. WICHMANN, M. S. MEINZ, L. GUARIGLIA, R. A. GIACOBB ...
1992 Volume 45 Issue 9 Pages
1397-1402
Published: September 25, 1992
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A novel inositol mono-phosphatase inhibitor, L-671, 776 (
1), was discovered from a culture of the hyphomycete,
Memnoniella echinata (ATCC 20928).
1 has a molecular weight of 388 and a molecular formula of C
23H
32O
5. The mode of inhibition is non-competitive, with a
Ki of 450μM. It shows no inhibition of
myo-inositol 1, 4-bisphosphate 1-phosphatase or
myo-inositol 1, 4, 5-triphosphate 5-phosphatase, although it weakly inhibits
myo-inositol 1, 4, 5-triphosphate 3-kinase (IC
50 = 3 mM). It elevates inositol monophosphates in rat parotid slices (EC
50 approximately 3 mM), but abolishes agonist effects. It also produces short-lived contraction of guinea pig trachea at 300 μM.
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TAXONOMY, PRODUCTION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITIES
TAKAAKI AOYAGI, HIROYUKI SUDA, KAZUMICHI UOTANI, FUKIKO KOJIMA, TAKAYU ...
1992 Volume 45 Issue 9 Pages
1404-1408
Published: September 25, 1992
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Nagstatin, a new inhibitor of
N-acetyl-β-D-glucosaminidase (NAG-ase) was discovered in the fermentation broth of
Streptomyces amakusaensis MG846-fF3. It was purified by chromatography on Dowex 50W, Avicel and Sephadex LH-20 followed by the treatment of active carbon and then isolated as colorless powder. Nagstatin has the molecular formula of C
12H
17N
3O
6. It is competitive with the substrate, and the inhibition constant (
Ki) was 1.7 × 10
-8M.
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I. PRODUCING ORGANISM, FERMENTATION, ISOLATION AND PHYSICO-CHEMICAL PROPERTIES
HIDETOSHI TAKAHASHI, HIROYUKI OSADA, HIROYUKI KOSHINO, TAKUJI KUDO, SH ...
1992 Volume 45 Issue 9 Pages
1409-1413
Published: September 25, 1992
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New antibiotics named reveromycins A, B, C and D were isolated as inhibitors of mitogenic activity induced by epidermal growth factor (EGF) in a mouse epidermal keratinocyte. Reveromycins were produced by a soil actinomycete (strain SN-593) which belongs to the genus
Streptomyces.
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II. BIOLOGICAL ACTIVITIES
HIDETOSHI TAKAHASHI, HIROYUKI OSADA, HIROYUKI KOSHINO, MUTSUMI SASAKI, ...
1992 Volume 45 Issue 9 Pages
1414-1419
Published: September 25, 1992
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Reveromycins A, B, C and D showed inhibitory activity against EGF-stimulated mitogen response in Balb/MK cells. Furthermore reveromycins A, C and D exhibited morphological reversion of
srcts-NRK cells, antiproliferative activity against human tumor cell lines and antifungal activity. The effects of reveromycins A, C and D on eukaryotic cells were closely similar to each other, but those of reveromycin B were very weak.
In vitro studies revealed that reveromycin A is a selective inhibitor of protein synthesis in eukaryotic cells.
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III. STRUCTURES OF REVEROMYCINS A, B, C AND D
HIROYUKI KOSHINO, HIDETOSHI TAKAHASHI, HIROYUKI OSADA, KIYOSHI ISONO
1992 Volume 45 Issue 9 Pages
1420-1427
Published: September 25, 1992
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Reveromycins A, B, C and D are new group inhibitors of the mitogenic activity of epidermal growth factor (EGF), produced by
Streptomyces sp. Reveromycins are novel polyketide type antibiotics which have two terminal carboxylic groups, a spiroketal, a succinate and a varied side chain in the molecule. Determination of their structures by chemical and spectroscopic methods, in particular NMR studies, is described.
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HIROYUKI KOSHINO, HIROYUKI OSADA, SHUICHI AMANO, RIE ONOSE, KIYOSHI IS ...
1992 Volume 45 Issue 9 Pages
1428-1432
Published: September 25, 1992
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RK-1409B, a new inhibitor of protein kinase C, was isolated from the culture broth of
Streptomyces platensis subsp.
malvinus RK-1409. The structure was elucidated on the basis of spectroscopic analyses. RK-1409B inhibited protein kinase C
in vitro and the morphological change of a human chronic leukemia cell line, K-562, induced by phorbol 12, 13-dibutyrate with IC
50 value of 0.4μM.
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PRODUCTION, ISOLATION, STRUCTURE AND BIOLOGICAL ACTIVITY
KOKO SUGAWARA, YUJI NISHIYAMA, SOICHIRO TODA, NOBUJIRO KOMIYAMA, MASAM ...
1992 Volume 45 Issue 9 Pages
1433-1441
Published: September 25, 1992
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Streptomyces amphibiosporus R310-104 (ATCC 53964) produced a novel antibiotic lactimidomycin which showed inhibitory activity against fungi and prolonged the survival time of mice transplanted with experimental tumors. Structural studies clarified that lactimidomycin is a new glutarimide antibiotic having a unique unsaturated 12-membered lactone ring.
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TAXONOMY, ISOLATION, PHYSICO-CHEMICAL PROPERTIES, STRUCTURE AND BIOLOGICAL ACTIVITY
CHIKAKO KOTAKE, TETSURO YAMASAKI, TOSHIO MORIYAMA, MIEKO SHINODA, NOBU ...
1992 Volume 45 Issue 9 Pages
1442-1450
Published: September 25, 1992
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New antifungal antibiotics, butyrolactols A and B, have been isolated from the culture broth of
Streptomyces rochei S785-16. They are novel type of molecules containing a common 2, 3-dihydroxybutyrolactone nucleus substituted with a different long hydroxyalkyl side chain. Butyrolactol A showed good antifungal activity against
Aspergillus fumigatus and
Trichophyton mentagrophytes, and moderately inhibited the growth of yeasts.
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I. ISOLATION AND BIOLOGICAL PROPERTIES
WALTER P. FRANKMÖLLE, LINDA K. LARSEN, FAITH R. CAPLAN, GREGORY M ...
1992 Volume 45 Issue 9 Pages
1451-1457
Published: September 25, 1992
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Laxaphycins are responsible for the antifungal and cytotoxic activity of crude ethanolic extracts from the cultured blue-green alga
Anabaena laxa. These cyclic peptides exhibit an unusual biological synergism when tested for antifungal or cytotoxic effects. The isolation procedure for the peptides, their characterization and biological activities are described here along with experiments demonstrating synergism between the two major laxaphycins.
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II. STRUCTURES OF LAXAPHYCINS A, B, D AND E
WALTER P. FRANKMÖLLE, GEORG KNÜBEL, RICHARD E. MOORE, GREGOR ...
1992 Volume 45 Issue 9 Pages
1458-1466
Published: September 25, 1992
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Laxaphycins A and B are the major components in an antifungal mixture of cyclic peptides from the terrestrial blue-green alga
Anabaena laxa FK-1-2. NMR and MS spectral studies coupled with amino acid analysis indicate that the gross structures of laxaphycins A and B are cyclic (Aoc-Hse-
E-Dhb-Hyp-Hse-Phe-Leu-Ile-Ile-Leu-Gly) where Aoc is a 3-aminooctanoic acid residue and cyclic (Ala-Hleu-Gln-
N-Melle-Hasn-Thr-Pro-Leu-Thr-Ade-Val-Hleu) where Ade is a 3-aminodecanoyl unit, respectively. Laxaphycin E, a minor cyclic undecapeptide, differs in gross structure from laxaphycin A in possessing a 3-aminodecanoic acid unit (Ade) in lieu of Aoc, whereas laxaphycin D, a minor cyclic dodecapeptide, differs from laxaphycin B in possessing a 3-aminooctanoyl unit (Aoc) instead of an Ade unit.
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I. PRODUCTION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITY
MLTSUAKI TSUNAKAWA, NOBUJIRO KOMIYAMA, OSAMU TENMYO, KOJI TOMITA, KIMI ...
1992 Volume 45 Issue 9 Pages
1467-1471
Published: September 25, 1992
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Kibdelosporangium albatum No. R761-7 (ATCC 55061) produced new antiviral antibiotics, cycloviracins B
1 and B
2. They show weak activity against Gram-positive bacteria and potent antiviral activity against herpes simplex virus type 1. Unique acylsaccharide structures were established for cycloviracins B
1 and B
2 by degradation and spectroscopic analysis.
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II. STRUCTURE DETERMINATION
MITSUAKI TSUNAKAWA, CHIKAKO KOTAKE, TETSURO YAMASAKI, TOSHIO MORIYAMA, ...
1992 Volume 45 Issue 9 Pages
1472-1480
Published: September 25, 1992
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The structures of novel antiviral antibiotics, cycloviracins B
1 and B
2 have been determined by means of chemical and spectroscopic methods including 2D NMR correlation spectroscopy. The antibiotics are unique macrocyclic diesters consisting of two D-glucoses, three 2-
O-methyl-D-glucoses and two (C
24 and C
26) hydroxy fatty acids.
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LESLEY PHILLIPS, ELIZABETH M. H. WELLINGTON, SARAH B. REES, LU SHU JUN ...
1992 Volume 45 Issue 9 Pages
1481-1491
Published: September 25, 1992
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Total DNA preparations from 74 antibiotic-producing type strains and 102 natural
Streptomyces isolates were examined by dot blots for homology to 6 antibiotic production and resistance genes. Pattern diversity of hybridizations decreased as stringency increased from 65% to 85%. There were 146 unique profiles at 65% stringency with 13 repeated patterns, whilst there were only 14 unique and 11 repeated profiles at 85% stringency. Most of the strains which hybridized at 85% reacted with one or two probes although a few strains showed multiple homologies. This data was used to cluster strains and the groups denned were examined for phenotypic antibiotic resistance. Producers of certain classes of antibiotics clustered to specific groups and some gene homologies were more common amongst strains which produced similar antibiotics.
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III. BIOSYNTHESIS
CAROL A. JONES, PHILIP J. SIDEBOTTOM, RICHARD J. P. CANNELL, DAVID NOB ...
1992 Volume 45 Issue 9 Pages
1492-1498
Published: September 25, 1992
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The biosynthetic origin of the carbon and oxygen atoms of the novel fungal secondary metabolite
1 was studied. Incorporation studies with single and multiple labelled
13C precursors indicated that the major portion of the molecule was derived from two polyketide chains made up of acetate units. One of the chains had benzoic acid (which can be derived from phenylalanine) as a starter unit. The remaining carbons were derived from a four-carbon unit related to succinate and from methionine. Studies with [1-
13C,
18O
2]acetate and
18O
2 indicated that five of the oxygens, including both of the heterocyclic oxygens, were derived from atmospheric oxygen. The oxygens at the two ester carbonyls were derived from acetate.
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MONTGOMERY E. FAVRET, JONATHAN W. PASCHAL, THOMAS K. ELZEY, LAVERNE D. ...
1992 Volume 45 Issue 9 Pages
1499-1511
Published: September 25, 1992
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The biosynthetic origin of antibiotic A10255 was investigated using
14C- and
13C-labeled amino acids. DL-[1-
13C]Serine labeled 15 of the 17 amino acid residues present in A10255G. These included the oxazole, thiazole, dehydroalanine, masked glycine, masked alanine and pyridine moieties. The same 15 residues labeled by serine were labeled by [2-
13C]glycine, apparently by conversion of the glycine to [2, 3-
13C]serine. Formation of the pyridine ring occurred
via a C3 to C3 condensation of two serines. The results indicated origin of the masked alanine from alanine; the masked glycine from glycine; the thiazole residues from cysteine; and the threonine, masked dehydrobutyrine, masked dehydronorvaline and masked dehydroleucine residues from threonine. L-[CH
3-
13C]Methionine labeled the methyl carbon of the masked dehydronorvaline moiety in factor B and the two methyl carbons of the masked dehydroleucine moiety in factor E. The results demonstrate that A10255 originates exclusively from amino acids in a manner similar to the closely related thiopeptide antibiotics nosiheptide and thiostrepton.
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TOSHIKAZU OKI, MASATOSHI KAKUSHIMA, MINORU HIRANO, AKIYO TAKAHASHI, AK ...
1992 Volume 45 Issue 9 Pages
1512-1517
Published: September 25, 1992
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BMS-181184 is a water-soluble pradimicin derivative with a broad antifungal spectrum
in vitro and demonstrable efficacy against systemic infections with
Candida albicans, Cryptococcus neoformans and
Aspergillus fumigatus in normal and cyclophosphamide-treated immunosuppressed mice.
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HAJIME KAMACHI, SEIJI IIMURA, SATSUKI OKUYAMA, HIDEAKI HOSHI, SACKING ...
1992 Volume 45 Issue 9 Pages
1518-1525
Published: September 25, 1992
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The 4'-
N-alkyl (
1-
10) and 4'-
N-acyl derivatives (
11-
21) of pradimicins (PRMs) were synthesized by trimethylsilylation of PRMs A, C and FA-1 followed by condensation with appropriate alkylating and acylating agents. The 4'-hydroxy derivatives (
23 and
24) were synthesized from PRM FA-2 in a 3-step sequence. Among these compounds, the 4'-
N-carboxylsubstituted alkyl (
1,
5,
8 and
10), 4'-
N-formyl (
11) and 4'-axial-hydroxy (
23) derivatives retained the antifungal activity of the parent compounds and showed great improvement in water solubility.
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NAO-AKI WATANABE, ISAO SUGIYAMA
1992 Volume 45 Issue 9 Pages
1526-1532
Published: September 25, 1992
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Cefclidin (E1040), which has an aminothiadiazolyl group in the 7β-side chain, showed about four-fold higher activity against
Pseudomonas aeruginosa than its aminothiazolyl counterpart. Cefclidin had lower affinity and a higher V
max value for the chromosomal type I β-lactamase (cephalosporinase) from
P. aeruginosa than its aminothiazolyl counterpart. No differences between the affinities of both compounds for the most of the sensitive essential PBPs were observed. Hydrophilicity of cefclidin was higher than that of its counterpart. The antipseudomonal activity of cefclidin, which was increased by the introduction of the aminothiadiazolyl group, was suggested to have resulted mainly from higher resistance to cephalosporinase hydrolysis at pharmacologically relevant low concentrations due to its low affinity for cephalosporinase, and secondarily from good penetration of cefclidin through the outer membrane due to increased hydrophilicity.
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VI. SYNTHESIS, ANTIBACTERIAL ACTIVITY AND ORAL EFFICACY IN MICE OF NEW 7β-[(Z)-2-(2-AMINOTHIAZOL-4-YL)-2-(HYDROXYIMINO)-ACETAMIDO]-3-(SUBSTITUTED ALKYLTHIO)CEPHALOSPORINS
CHIHIRO YOKOO, AKIRA ONODERA, HIROSHI FUKUSHIMA, KAZUO NUMATA, TAKATOS ...
1992 Volume 45 Issue 9 Pages
1533-1539
Published: September 25, 1992
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A series of new 7β-[(
Z)-2-(2-aminothiazol-4-yl)-2-(hydroxyimino)acetamido]cephalosporins (
1) having various substituted alkylthio groups at the C-3 position of the cephem nucleus were prepared and evaluated for antibacterial activity and oral absorption in rats. Of these, the cephalosporin with a cyanomethylthio group (
1a) showed the greatest activity against
Staphylococcus aureus and Gram-negative bacteria. Its pivaloyloxymethyl ester (
6a), a representative prodrug, exhibited good
in vivo efficacy in mice by oral administration. The structure-activity relationships of
1 are also presented.
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MOHINDAR S. PUAR, DORIS SCHUMACHER, TOM MOLLITOR, BERNARD ROSENKRANTZ, ...
1992 Volume 45 Issue 9 Pages
1540-1543
Published: September 25, 1992
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The structures of two solid-state rearrangement products, A and B, of rosaramicin have been assigned on the basis of
13C NMR spectral data and a single-crystal X-ray analysis of the acetone solvate of product B.
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JOHN P. DIRLAM, JON BORDNER, SHANG-POA CHANG, ANTONIO GRIZZUTI, THEODO ...
1992 Volume 45 Issue 9 Pages
1544-1548
Published: September 25, 1992
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BRIGITTE KUNZE, ROLF JANSEN, LUTZ PRIDZUN, ELKE JURKIEWICZ, GERHARD HU ...
1992 Volume 45 Issue 9 Pages
1549-1552
Published: September 25, 1992
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MASATOMI IIJIMA, TOHRU MASUDA, HIKARU NAKAMURA, HIROSHI NAGANAWA, SHOG ...
1992 Volume 45 Issue 9 Pages
1553-1556
Published: September 25, 1992
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TAKAYUKI AOYAMA, HIROSHI NAGANAWA, HIROYUKI SUDA, KAZUMICHI UOTAN, TAK ...
1992 Volume 45 Issue 9 Pages
1557-1558
Published: September 25, 1992
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