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I. Taxonomy of Producing Strain, Fermentation, Isolation, Physico-chemical Properties and Biological Properties
TETSUO AKIYAMA, SHIGEKO HARADA, FUKIKO KOJIMA, NAOKO KINOSHITA, MASA H ...
1998 年 51 巻 3 号 p.
253-260
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
A new inhibitor of dipeptidyl peptidase II (DPP-II, EC 3.4.14.2), designated as epostatin, was discovered in the fermentation broth of a strain isolated in our institute. The strain has been identified as
Streptomyces sp. MJ995-OF5 on the basis of taxonomic studies. Epostatin was obtained as a yellow powder after seqential purification by chromatography on Diaion HP-20,
n-butanol extraction, Sephadex LH-20 column chromatography and centrifugal partition chromatography (CPC). Epostatin inhibited DPP-II competitively in a dose dependent manner. The compound was slightly inhibitory against other dipeptidyl peptidases.
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I. Producing Organism, Fermentation, Isolation and Biological Activities
HARUMI OGAWA, YOSHINORI YAMASHITA, RITSUKO KATAHIRA, SHIGERU CHIBA, TO ...
1998 年 51 巻 3 号 p.
261-266
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
We developed a microbial prescreen using
Bacillus stearothermophilus NUB3620 and bacteriophage TP-68 to detect potential antitumor compounds acting on DNA or topoisomerases. During the course of screening microbial cultures for their antibacteriophage activities, we found that
Streptomyces sp. isolated from a soil sample collected in Iwakuni city, Yamaguchi prefecture, Japan, produced a new antitumor antibiotic, UCH9. UCH9 was isolated from culture broth by a combination of EtOAc extraction and column chromatography. UCH9 has a new structure related to the antitumor antibiotic chromomycins. It exhibited antimicrobial activity against Gram-positive organisms. UCH9 also showed cytotoxic activity against HeLa S3 cells with an IC
50 value of 13nM and exhibited antitumor activity
in vivo against mouse leukemia P388.
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II. Structure Elucidation of UCH9 by Mass and NMR Spectroscopy
RITSUKO KATAHIRA, YOICHI UOSAKI, HARUMI OGAWA, YOSHINORI YAMASHITA, HI ...
1998 年 51 巻 3 号 p.
267-274
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
The structure of UCH9, which is a novel antitumor agent, was determined by spectroscopic methods. UCH9 consists of an aglycone and five 2, 6-dideoxy sugars (three D-olivoses, one 4-
O-methyl-D-olivose and one D-oliose). Four of the five sugars are sequentially connected through a β1→3 linkage (olivose-1→3-4-
O-methyl-olivose-1→3-oliose-1→3-olivose). On the basis of the results of spectroscopic analysis, it was found that UCH9 belongs to the aureolic acid family of antibiotics. The structure of UCH9 is unique in that mono- and tetrasaccharide moieties, and a long hydrophobic side chain (
sec-butyl group) are attached to the aglycone, while di- and trisaccharide moieties and a methyl or a hydrogen are attached in the case of the known aureolic acid analogs. It is known that aureolic acid analogs form a dimer in the presence of Mg
2+. NMR, FAB-MS and atomic absorption analysis revealed that UCH9 isolated from
Streptomyces also forms a dimer, containing one equivalent molar Mg
2+
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MAKOTO OJIKA, YOSHIHIRO SUZUKI, AKANE TSUKAMOTO, YOUJI SAKAGAMI, RYOSU ...
1998 年 51 巻 3 号 p.
275-281
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
New bithiazole-type antibiotics, cystothiazoles A (C
20H
26N
2O
4S
2) and B (C
20H
26N
2O
5S
2), have been isolated from a culture broth of the myxobacterium,
Cystobacter fuscus. The gross structures of these compounds were elucidated by spectroscopic analysis, and their absolute stereochemistry was determined by chemical degradation of cystothiazole A. Cystothiazole A inhibits fungi and human tumor cells, whereas it is inactive against bacteria. The antifungal activity appears to result from the inhibition of submitochondrial NADH oxidation. Although these compounds are structurally related to the known antibiotic myxothiazol, cystothiazole A was more active against fungi and less cytotoxic than myxothiazol.
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YA-FANG QIAO, TADAYASU OKAZAKI, TSUTOMU ANDO, KAZUTOSHI MIZOUE, KATSUY ...
1998 年 51 巻 3 号 p.
282-287
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
During our screening of microbial metabolites for effective drugs against tumor cell lines, we discovered a new pyrano[4′, 3′:6, 7]naphtho[1, 2-b]xanthene derivative, FD-594 from the fermentation broth of
Streptomyces sp. TA-0256. FD-594 shows moderate activity against tumor cell lines, comparative to that of adriamycin, as well as antibacterial activity against some Gram-positive bacteria.
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KATSUYA KONDO, TADASHI EGUCHI, KATSUMI KAKINUMA, KAZUTOSHI MIZOUE, YA- ...
1998 年 51 巻 3 号 p.
288-295
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
The structure of a novel antitumor antibiotics FD-594 (1), produced by
Streptomyces sp. TA-0256, was determined to have a glycosylated pyrano[4′, 3′:6, 7]naphtho[1, 2-b]-xanthene skeleton by means of spectral data. The biosynthetic studies of the chromophore of 1 was also carried out by feeding experiments with [1-
13C]-, [2-
13C]-, and [1, 2-
13C
2]sodium acetate. The labeling pattern was determined by
13C NMR including 2D INADEQUATE experiments, which allowed us to elucidate that the chromophore of 1 is derived from 14 acetate, followed by the loss of one carbon atom.
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I. Taxonomy and Fermentation
D. ABBANAT, M. LEIGHTON, W. MAIESE, E.B.G. JONES, C. PEARCE, M. GREENS ...
1998 年 51 巻 3 号 p.
296-302
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
The cell wall targeted antifungal activity of
Hypoxylon oceanicum LL-15G256 extracts resulted from the production of novel lipodepsipeptides and previously reported macrocyclic polylactones. In an optimized medium, titers of the lipodepsipeptide and the polylactones reached approximately 200-400 mg/liter and 25-50 mg/liter, respectively. The optimum fermentation temperature for production of 15G256γ was 28°C. Seawater appeared to have an inhibitory effect on metabolite accumulation at lower fermentation temperatures.
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II. Isolation and Structure Determination
GERHARD SCHLINGMANN, LISA MILNE, DAVID R. WILLIAMS, GUY T. CARTER
1998 年 51 巻 3 号 p.
303-316
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
Fermentations of the marine fungus
Hypoxylon oceanicum (LL-15G256) were found to have potent antifungal activity. Isolation and purification of the antifungal agents provided two classes of compounds, macrocyclic polylactones and the lipodepsipeptides 15G256γ (1), 15G256δ (2) and 15G256ε (3). The isolation and structure elucidation of the lipodepsipeptides, all containing D-glutamate, L-serine, and the rare amino acid β-ketotryptohan, are described in this paper.
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III. Biological Properties of 15G256γ
DAVID ALBAUGH, GUIDO ALBERT, PATRICIA BRADFORD, VAN COTTER, JAMES FROY ...
1998 年 51 巻 3 号 p.
317-322
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
15G256γ is a cyclic lipopeptide antifungal agent discovered in a mechanism of action screen for cell wall acting antifungal agents. The compound shows moderate activity in both greenhouse tests against plant disease caused by pathogenic fungi and in
in vitro tests against human fungal pathogens. Microscopic examination of treated fungi suggests that the compound acts by the inhibition of cell wall biosynthesis. However,
in vitro inhibition of
Neurospora crassa glucan and chitin synthase were only observed at high drug concentrations suggesting that 15G256γ may act on a novel cell wall target.
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I. Taxonomy, Fermentation, Isolation, Physico-chemical Properties and Biological Activities
SHINOBU KOBAYASHI, SHIGETADA HIDAKA, YOSHIHIRO KAWAMURA, MAMORU OZAKI, ...
1998 年 51 巻 3 号 p.
323-327
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
A Gram-negative bacterium was found to produce a new zinc-containing antibiotics, micacocidin A and related compounds containing Cu or Fe, micacocidin B and C, respectively. These antibiotics were isolated by column chromatography on silica gel, and then separated by preparative TLC and HPLC. These new antibiotics exhibited an excellent activity against
Mycoplasma species. The producing bacterium was characterized and ascribed to the genus
Pseudomonas.
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II. Structure Elucidation
SHINOBU KOBAYASHI, HIROSHI NAKAI, YUJI IKENISHI, WEI-YIN SUN, MAMORU O ...
1998 年 51 巻 3 号 p.
328-332
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
Metal-containing novel heterocyclic antibiotics, micacocidin A (1), B (2), and C (3) have been isolated from the culture filtrate of
Pseudomonas sp. No. 57-250. The structure and absolute configuration of micacocidin A, an octahedral Zn
2+ complex, was determined by X-ray crystallographic analysis. And then, the structures of the two congeners, micacocidin B (Cu
2+ complex) and C (Fe
3+ complex) were investigated by employing one dimensional and two dimensional homonuclear and heteronuclear NMR spectroscopies and mass spectrometry.
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M. A. FAROOQ BIABANI, MATTHIAS BAAKE, BARBARA LOVISETTO, HARTMUT LAATS ...
1998 年 51 巻 3 号 p.
333-340
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
2-[Methyl-(3-phenylpropionyl)amino]-benzoic acid (1e) was isolated from a culture of marine
Streptomyces sp. strain B7747. Analogous compounds have potential importance as phytotoxic substances, hence compound 1e and the analogues 1a∼1d and 1f∼3a were synthesised. Antimicroalgal activity of the anthranilamide analogues showed that esters 1b, 1f and 2b were more active than the free acids. The minimum inhibitory concentration (MIC) against
Chlorella vulgaris,
Chlorella sorokiniana,
Chlorella salina and
Scenedesmus subspicatus ranged from 20 to 107 μg/ml. All anthranilamides were inactive against
Staphylococcus aureus,
Escherichia coli, and
Mucor miehei.
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SOUICHI IKENO, TOMOHIRO TSUJI, KENJI HIGASHIDE, NAOKO KINOSHITA, MASA ...
1998 年 51 巻 3 号 p.
341-352
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
A 7.6 kb P
stI-K
pnI DNA fragment including a sequence highly similar to kasugamycin acetyltransferase gene (
kac) was isolated from
Streptomyces kasugaensis M338-M1 and sequenced. Nine open reading frames (ORFs), designated as ORF A, B, C, D, E, F, G, H and I, were recognized in this region, although ORF A was incomplete. ORF G runs in the opposite direction to the others. The amino acid sequence deduced from ORF H showed 98% similarity to that of the kasugamycin acetyltransferase from
S. kasugaensis MB273-C4, another kasugamycin (KSM) producer. Transformation of
E. coli JM109 with ORF H made the strain highly resistant to KSM. The deduced amino acid sequences of the ORF A, C and D products were similar, respectively, to glucosyltransferase I from
E. coli (26%), β-alanine: pyruvate transaminase from
Pseudomonas putida (32%) and dTDP-D-glucose 4, 6-dehydratase (StrE) from
Streptomyces griseus (37%). The
strE-like ORF (ORF D) seems to be the gene responsible for formation of the 6-deoxy structure of the kasugamine moiety. ORF A and ORF C are also likely to have roles in KSM biosynthesis. Taken together, our analyses strongly suggest that this DNA region includes at least a part of the gene cluster of KSM biosynthesis.
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TORU KUROME, KAZUTOH TAKESAKO, IKUNOSHIN KATO, TAKASHI TSURUO
1998 年 51 巻 3 号 p.
353-358
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
Cyclic depsipeptide antibiotic aureobasidin A (AbA) and its analogs were tested for the inhibitory activity of P-glycoprotein in multidrug resistant cancer cells as well as for the antifungal activity. Some analogs with lower antifungal activity than AbA showed higher inhibition of P-glycoproteins indicating difference of the structure-activity relationships between the two activities. Among AbA analogs tested, [D-β-hydroxy-methylvalyl
9]-AbA newly prepared by chemical synthesis, which had much lower antifungal activity than AbA, showed 10-fold higher inhibitory activity of P-glycoprotein than AbA.
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TORU KUROME, TETSUYA INOUE, KAZUTOH TAKESAKO, IKUNOSHIN KATO, KAORU IN ...
1998 年 51 巻 3 号 p.
359-367
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
The syntheses of aureobasidin A (AbA) derivatives with alkyl chains and their
in vitro structure-biological activity relationships are discussed. The analogs replaced at positions 6, 7, or 8 of AbA with either L-glutamic acid, δ-hydroxy-L-norvaline, or δ-hydroxy-
N-methyl-L-norvaline are prepared. The γ-carboxyl or δ-hydroxyl group of these new amino acids was coupled with acids, alcohols, or amines with alkyl chains. While the analogs having L-glutamic acid residue at positions 6 or 8 showed weak activity, esterification of the γ-carboxyl group with benzyl or shorter alkyl (C
4 or C
6) alcohols, significantly enhanced the activities. Introduction of longer alkyl (C
14) chain to the same amino acids residues at positions 6, 7, or 8 resulted in total loss of antifungal activity. Among the lipophilic analogs in [L-Glu
6] derivatives, the C
6 alcohol ester showed the strongest antifungal activity against
Candida spp. so far tested. None of the derivatives showed activity against
Cryptococcus neoformans.
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CLAUDIA CHRISTNER, GERHARD KÜLLERTZ, GUNTER FISCHER, MARION ZERLI ...
1998 年 51 巻 3 号 p.
368-371
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
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II. Structure Elucidation
TETSUO AKIYAMA, RYUICHI SAWA, HIROSHI NAGANAWA, YASUHIKO MURAOKA, TAKA ...
1998 年 51 巻 3 号 p.
372-373
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
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II: 2-Alkyl and 2-Arylthiomethyl Derivatives
HIDENORI AZAMI, KEIJI MATSUDA, HIDEO TSUTSUMI, TOSHIAKI KAMIMURA, MASA ...
1998 年 51 巻 3 号 p.
374-377
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
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JAE-HOON KANG, SEUNG-WOO YU, SEUNG-YOUNG LEE, KEE-WON KIM
1998 年 51 巻 3 号 p.
378-380
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
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BJÖRN BIEBER, JÖRG NÜSKE, MICHAEL RITZAU, UDO GRÄF ...
1998 年 51 巻 3 号 p.
381-382
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー
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KUNIAKI TATSUTA, TORU YAMAZAKI, TAKUJI YOSHIMOTO
1998 年 51 巻 3 号 p.
383-386
発行日: 1998/03/25
公開日: 2009/01/27
ジャーナル
フリー