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FUSAO TOMITA, TATSUYA TAMAOKI, MAKOTO MORIMOTO, KAZUHISA FUJIMOTO
1981 年 34 巻 12 号 p.
1519-1524
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
A group of antitumor antibiotics with a novel skeleton, trioxacarcins, was discovered in culture broths of actinomycete strain DO-45. The producing organism was subsequently determined to be a new strain and named
Streptomyces bottropensis DO-45. The antibiotics are active against Gram-positive bacteria and experimental murine tumors such as sarcoma 180 and leukemia P388.
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II. ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND MODE OF ACTION
TATSUYA TAMAOKI, KUNIKATSU SHIRAHATA, TAKAO IIDA, FUSAO TOMITA
1981 年 34 巻 12 号 p.
1525-1530
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Novel antitumor antibiotics, trioxacarcin complex, were isolated from the fermentation broth of
Streptomyces bottropensis DO-45 by the use of non-ionic porous resin and silica gel chromatography. The purified components (trioxacarcins A, B and C) were characterized as new antibiotics by their physico-chemical properties and chromatographic behaviors. The mode of action of trioxacarcin A against
Bacillus subtilis was found to be through the of DNA synthesis.
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I. ISOLATION, CHARACTERIZATION AND BIOLOGICAL PROPERTIES
BEATEE WERSMEYER-WENK, HANS ZÄHNER, BERND KRONE, AXEL ZEECK
1981 年 34 巻 12 号 p.
1531-1537
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Novel antitumor antibiotics, trioxacarcin complex, were isolated from the fermentation broth of
Streptomyces bottropensis DO-45 by the use of non-ionic porous resin and silica gel chromatography. The purified components (trioxacarcins A, B and C) were characterized as new antibiotics by their physico-chemical properties and chromatographic behaviors. The mode of action of trioxacarcin A against
Bacillus subtilis was found to be through the of DNA synthesis.
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II. CHEMICAL STRUCTURE AND DERIVATIVES
BERND KRONE, ANKE HINRICHS, AXEL ZEECK, AXEL ZEECK
1981 年 34 巻 12 号 p.
1538-1543
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Evidence is put forward, which describes the structure of haloquinone as 3-acetyl-1, 8-dihydroxy-2-methyl-9, 10-phenanthrenequinone (1a).
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D. M. BALITZ, F. A. O'HERRON, J. BUSH, D. M. VYAS, D. E. NETTLETON, R. ...
1981 年 34 巻 12 号 p.
1544-1555
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
The isolation and structure elucidation of gilvocarcins V, M and E from
Streptomyces anandii is reported. Solvent extraction and high performance liquid chromatography were employed along with NMR and X-ray crystallographic analysis. Gilvocarcins V and M showed antimicrobial activity while only gilvocarcin V demonstrated potential as an antitumor agent.
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NOBUAKI KITAHARA, AKIRA ENDO
1981 年 34 巻 12 号 p.
1556-1561
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Xanthocillin X monomethyl ether, known as an antiviral antibiotic, was isolated as a potent inhibitor of
ichotomomyces cejpii. The compound inhibited prostaglandin synthesis from
14C-arachidonic acid in rabbit kidney microsomes by 50% at a concentration of 0.2 μM, while prostaglandin synthesis by microsomes of ram seminal vesicle was inhibited by 50% at 20 μM. The inhibition by xanthocillin X monomethyl ether was reversible. Of the enzymatic steps involved in the synthesis of prostaglandins and thromboxanes tested, conversion of arachidonic acid into prostaglandin H
2 was specifically inhibited by xanthocillin X monomethyl ether. Anti-inflammatory activity of this antibiotic on carrageenan-induced oedema in the rat foot was, however, not detectable.
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NOBUAKI KITAHARA, AKIRA ENDO, KOHEI FURUYA, SHUJI TAKAHASHI
1981 年 34 巻 12 号 p.
1562-1568
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Two potent inhibitors of prostaglandin biosynthesis, thielavin A (C
31H
34O
10) and B(C
29H
30O
10), were isolated from cultures of
Thielavia terricola. Both of these compounds were shown to be structurally related to depsides, thus consisting of three hydroxybenzoic acid groups. Concentrations required for 50% inhibition of the conversion of
14C-arachidonic acid into prostaglandins F
2α, plus E
2 by microsomes of ram seminal vesicles were 12 μM for thielavin A and 9 μM for thielavin B, respectively. Of the enzymatic steps involved in prostaglandin synthesis, thielavin A specifically inhibited the conversion of arachidonic acid into prostaglandin H
2, while prostaglandin E
2 synthesis from the endoperoxide was the most sensitive to thielavin B.
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MASAO KOYAMA, YOSHIO KODAMA, TAKASHI TSURUOKA, NORIO EZAKI, TOMIZO NIW ...
1981 年 34 巻 12 号 p.
1569-1576
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Pyrrolomycin A, a new antifungal antibiotic produced by an actinomycete, has a molecular formula C
4H
2N
202Cl2. Its structure was determined to be 2, 3-dichloro-4-nitropyrrole by spectroscopic analysis and synthetic studies. Structure-activity relationships among the analogs of pyrrolomycin A are discussed.
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HIDEO SAKAKIBARA, TATSURO FUJIWARA, MINORU AIZAWA, SATOSHI OMURA
1981 年 34 巻 12 号 p.
1577-1580
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
9-
epi-Leucomycin A
5 has been obtained from leucomycin A
5 (I) by the following reaction sequence. Leucomycin A5 (I) was treated with Collins reagent (CrO3-pyridine) in the presence of water (13%) to provide 9-dehydroleucomycin A5 (II) in 95% yield. The formyl group was internally protected by the reaction of II with acetic anhydride-K2CO3 to afford 18, 2'-di-
O -acetyl-9-dehydroleucomycin A
5-3, 18-hemiacetal (III). Sodium borohydride reaction of II provided a 1: 1 mixture of natural I and its 9-epimer, 9-
epi-leucomycin A5 (IV), which were separated by silica gel chromatography. It was observed that the antimicrobial activities of both enantiomers were virtually identical with some test strains but that of IV is reduced in comparison with I in some bacteria such as
Staphylococcus epidermidis sp-al-1 and
Streptococcus pyogenes N. Y. 5.
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KAZUO NAKAHAMA, MOTOWO IZAWA, MITSUKO ASAI, MAKOTO KIDA, TOYOKAZU KISH ...
1981 年 34 巻 12 号 p.
1581-1586
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Bacteria, actinomycetes, yeasts, and fungi were screened for their ability to modify the structure of ansamitocins, a group of antitumor ansamycin antibiotics. Many strains, mostly actinomycetes, were found to convert ansamitocin P-3 to one or more products. These products, compounds A, B, C, and D, were prepared using
Bacillus megaterium IFO 12108,
Streptomyces coelicolor IFO 3807,
Streptomyces castaneus IFO 13670 and
Streptomyces minutiscleroticus IFO 13361, and were identified as 20-
O-demethylansamitocin P-3, maytansinol, 15-hydroxyansamitocin P-3 and
N-demethylansamitocin P-3, respectively. Other maytansinoids also underwent these microbial conversions.
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MOTOWO IZAWA, KAZUO NAKAHAMA, FUMIKO KASAHARA, MITSUKO ASAI, TOYOKAZU ...
1981 年 34 巻 12 号 p.
1587-1590
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Ansamitocins were converted into 20-
O-demethyl derivatives by bacteria. The structures of these products were elucidated from their physicochemical properties and from the chemical conversion to ansamitocins with diazomethane.
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MOTOWO IZAWA, YOSHIKAZU WADA, FUMIKO KASAHARA, MITSUKO ASAI, TOYOKAZU ...
1981 年 34 巻 12 号 p.
1591-1595
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Ansamitocin P-3 was converted into 15-hydroxyansamitocin P-3 (PHO-3), C
32H
43ClN
20
10, and 15-
epi-15-hydroxyansamitocin P-3 (
epi-PHO-3), C
32H43ClN2010, by actinomycetes. PHO-3 was identical to deacetylmaytanbutacine and epi-PHO-3 was a new compound. The configuration at C15 was elucidated as R for PHO-3 and S for epi-PHO-3 on the basis of their physicochemical properties and X-ray analysis of epi-PHO-3.
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YASUE MATSUZAWA, TOSHIKAZU OKI, TOMIO TAKEUCHI, HAMAO UMEZAWA
1981 年 34 巻 12 号 p.
1596-1607
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
The effects of 92 anthracycline compounds on the growth and DNA, RNA and protein synthesis of L1210 leukemia cells were studied in relationships to their structures and antitumor activity. The following structure-activity relationships were observed: 1) The hydroxyl groups at C-1, C-2, C-4, C-6 and C-11 on aglycones have significant relationships to the
in vitro potency. Compounds lacking the hydroxyl group at C-6 (an anthracycline containing α
2-rhodomycinone) or containing the methoxyl group at C-6 (6-
O-methylaclacinomycin A) are lower in their cytotoxicity and RNA and DNA synthesis-inhibiting activity than those containing the C-6 hydroxyl group. The hydroxyl group at C-2 did not influence the
in vitro potency, but the hydroxyl group at C-1 and/or C-11 enhanced the potency. The activity which prolongs the life span of L1210-bearing mice was decreased by an hydroxyl group at C-1 or C-11, although the effective doses were lowered. In compounds which are different at C-4,
in vitro potency increased in the following series: deoxy>hydroxy>methoxy. 2) The side chain at C-9 in aklavinone- and daunomycinone-glycosides produced slight influence on cytotoxicity and on the activity which inhibits RNA and DNA synthesis in intact cells. Ethyl, isopropyl and acetonyl derivatives at C-9 had an equal potency. The methyl derivative had the least activity. 3) A 10-carbomethoxy group in the
S-configuration decreased the inhibitory activity on RNA synthesis. The removal of this group at C-10 resulted in a marked reduction in cytotoxicity and in the activity which inhibits nucleic acid synthesis. 4) The amino function either on the aglycone or on the sugar moiety was essential for
in vitro activity. Compounds having an alkylamino group at C-3' were more potent
in vitro than those with a primary amino group, although these groups produced different effects in
in vivo activity, depending on each anthracycline. 5) Disaccharides and trisaccharides were more potent
in vitro than monosaccharides. This was reflected in the ratios for the IC
50 values of DNA and RNA synthesis. The ratio of the concentration to inhibit DNA synthesis to that for RNA synthesis was 1-4 in monosaccharides (group I), while in trisaccharides (group II). the ratio was 7-10. In disaccharides the ratio was 5-6. The length of the sugar chain did not correlate with
in vivo antitumor activity.
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HENRYK CHMARA, BARBARA WOYNAROWSKA, EDWARD BOROWSKI
1981 年 34 巻 12 号 p.
1608-1612
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
Tetaine induced the lysis of
Escherichia coli cells. Several di- and tripeptides were found to protect this cells against tetaine action. Certain peptides are able to diminish the inhibition by tetaine of diaminopimelic acid incorporation into peptidoglycan and the extent of this corresponds to the protection of the cells against the tetaine-induced lysis. The data indicate that tetaine enters
E. coli cells predominantly by dipeptide permease and in part by one or more oligopeptide permease system. A number of di- and tripeptides diminished the inhibitory effect of tetaine on the incorporation of lysine into peptidoglycan of
Staphylococcus aureus Oxford. In contrast to
E. coil, tetaine seems to be transported into
S. aureus by a single transport system.
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NOBUYOSHI SHIMADA, KAZUSHI MORIMOTO, HIROSHI NAGANAWA, TOMOHISA TAKITA ...
1981 年 34 巻 12 号 p.
1613-1614
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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KAZUSHI MORIMOTO, NOBUYOSHI SHIMADA, HIROSHI NAGANAWA, TOMOHISA TAKITA ...
1981 年 34 巻 12 号 p.
1615-1618
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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TOMIO TAKEUCHI, HIRONOBU IINUMA, SETSUKO KUNIMOTO, TORU MASUDA, MASAAK ...
1981 年 34 巻 12 号 p.
1619-1621
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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HAMAO UMEZAWA, SHINICHI KONDO, HIRONOBU IINUMA, SETSUKO KUNIMOTO, YOKO ...
1981 年 34 巻 12 号 p.
1622-1624
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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SHINICHI KONDO, HIROYUKI IWASAWA, DAISHIRO IKEDA, YOSHIHISA UMEDA, YOK ...
1981 年 34 巻 12 号 p.
1625-1627
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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YOKO IKEDA, SHINICHI KONDO, TSUTOMU SAWA, MASAMI TSUCHIYA, DAISHIRO IK ...
1981 年 34 巻 12 号 p.
1628-1630
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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KLAUS ECKARDT, WOLFGANG IHN, DIETER TRESSELT, DIETRICH KREBS
1981 年 34 巻 12 号 p.
1631-1632
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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SATOSHI OMURA, YUZURU IWAI, YOKO TAKAHASHI, KAZUKO KOJIMA, KAZUHIKO OT ...
1981 年 34 巻 12 号 p.
1633-1634
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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HAMAO UMEZAWA, TSUYOSHI MIYASAKA, HIROYUKI IWASAWA, DAISHIRO IKEDA, SH ...
1981 年 34 巻 12 号 p.
1635-1640
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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3-METHYLENE SUBSTITUENT EFFECT ON STRUCTURE-REACTIVITY RELATIONSHIP OF CEPHALOSPORINS STUDIED BY CARBON-13 NMR SPECTROSCOPY
JUNKO NISHIKAWA, KAZUO TORI
1981 年 34 巻 12 号 p.
1641-1644
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー
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7-ACYLAMINO SUBSTITUENT EFFECT ON STRUCTURE-REACTIVITY RELATIONSHIP OF CEPHALOSPORINS STUDIED BY CARBON-13 NMR SPECTROSCOPY
JUNKO NISHIKAWA, KAZUO TORI
1981 年 34 巻 12 号 p.
1645-1648
発行日: 1981年
公開日: 2006/04/12
ジャーナル
フリー