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DA-JUN YANG, HIROSHI TOMODA, NORIKO TABATA, ROKURO MASUMA, SATOSHI OMU ...
1996 Volume 49 Issue 3 Pages
223-229
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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New isochromophilones VII and VIII were isolated from the culture broth of
Penidllium sp. FO-4164. The structures were elucidated as 6
H-2-benzopyran-6, 8(7
H)-dione, 5-chloro-3-(3', 5'-dimethyl-1', 3'-heptadienyl)-1, 7, 8a-trihydro-7, 8a-dihydroxy-7-methyl-7-acetate for isochromophilone VII and 6
H-2-benzopyran-6-one, 5-chloro-3-(3', 5'-dimethyl-1', 3'-heptadienyl)-1, 7, 8, 8a-tetrahydro-7, 8-dihydroxy-7-methyl-8-acetate for isochromophilone VIII. Isochromophilones VII and VIII inhibited diacylglycerol acyltransferase activity with IC50 values of 20.0 and 127 μM and acyl-CoA: cholesterol acyltransferase activity with IC50 values of 24.5 and 47.0 μM, respectively.
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THEODOR FEHR, JEAN-JACQUES SANGLIER, WALTER SCHULER, LILIANE GSCHWIND, ...
1996 Volume 49 Issue 3 Pages
230-233
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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5 novel ascomycin-like compounds, antascomicins A, B, C, D and E were isolated from a strain of
Micromonospora. The antascomicins bind strongly to the FK506-binding protein FKBP12 and antagonize the immunosuppressive activity of FK506 and rapamycin. The strain description, fermentation, structure elucidation and biological activity of these compounds are described.
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GLENN A. WARR, JUDITH A. VEITCH, ANN W. WALSH, GRACE A. HESLER, DOLORE ...
1996 Volume 49 Issue 3 Pages
234-240
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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A fungal metabolite, BMS-182123, which inhibited bacterial endotoxin-induced production of tumor necrosis factor (TNF-α) in murine macrophages and human peripheral blood monocytes (
in vitro), was isolated from the culture broth of
Penicillium chrysogenum strain V39673. The effective BMS-182123 concentration (IC50) resulting in 50% inhibition of lipopolysaccharide-induced TNF-α production in murine macrophages and human monocytes was 600 ng/ml and 4.0 μg/ml, respectively. BMS-182123 suppressed the lipopolysaccahride-induced TNF-α promoter activity and did not affect the stability of posttranscriptional mRNA. Addition of hydrophobic resin, Amberlite XAD-8 (1%), to the fermentation enhanced the production of BMS-182123 by 5.5 fold. A total of 577 mg pure BMS-182123 was recovered from a 250-liter fermentation supplemented with 1 % Amberlite XAD-8.
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I. Taxonomy, Production, Isolation and Biological Activities
KAZUTOSHI SHINDO, MICHIKO MATSUOKA, HIROYUKI KAWAI
1996 Volume 49 Issue 3 Pages
241-243
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Novel antitumor antibiotics cochleamycins A, A2, B and B2 (Fig. 1) were isolated from the culture broth of
Streptomyces sp. DTI36. They were purified by column chromatography on silica gel, reversed phase HPLC and then isolated as colorless powder. Cochleamycins showed growth inhibition against tumor cells
in vitro.
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II. Physico-chemical Properties and Structure Determination
KAZUTOSHI SHINDO, HIROSHI IIJIMA, HIROYUKI KAWAI
1996 Volume 49 Issue 3 Pages
244-248
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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The structure of cochleamycins A, A2, B and B2 (Fig. 1), novel antitumor antibiotics, were elucidated by NMR spectral analysis. Cochleamycins were found to possess novel carbocyclic skeletons.
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III. Biosyntheses of Cochleamycins: Incorporation of 13C-and 2H-Labeled Compounds into Cochleamycins
KAZUTOSHI SHINDO, MASAYUKI SAKAKIBARA, HIROYUKI KAWAI, HARUO SETO
1996 Volume 49 Issue 3 Pages
249-252
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Biosynthetic studies using
13C- and
2H-labeled compounds revealed that the carbon skeletons of Cochleamycins A and B were derived from eight acetic acid units and one propionic acid unit with the introduction of an acetoxy group at C-10, which was replaced by an isobutyryl residue derived from valine in Cochleamycins A2 and B2.
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I. The Producing Organism and Biological Activity
RUSSELL B. LINGHAM, AMY H. M. Hsu, JULIE A. O'BRIEN, JANET M. SIGMUND, ...
1996 Volume 49 Issue 3 Pages
253-259
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Quinoxapeptm A and B are novel chromodepsipeptides which were isolated from a nocardioform actinomycete with indeterminant morphology. Quinoxapeptins A and B are potent inhibitors of HIV-1 and HIV-2 reverse transcriptase and almost equally active against two single mutants forms as well as a double mutant form of HIV-1 reverse transcriptase. Quinoxapeptin A and B are specific inhibitors of HIV-1 and HIV-2 reverse transcriptase because they did not inhibit human DNA polymerase α, β, γ and δ. Quinoxapeptin A and B are structurally similar to luzopeptin A which was also active against HIV-1 and HIV-2 reverse transcriptase.
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I. Production, Isolation, Physico-chemical Properties and Structure Elucidation
GIORGIO LAMPIS, DELIA DEIDDA, CARLO MAULLU, SABRINA PETRUZZELLI, RAFFA ...
1996 Volume 49 Issue 3 Pages
260-262
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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An original compound, named karalicin, was isolated from a fermentation broth of the
Pseudomonas fluorescens/
putida strain SS-3 (CCM 4430). Production, physico-chemical properties and structure elucidation are described.
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II. Biological Properties
GIORGIO LAMPIS, DELIA DEIDDA, CARLO MAULLU, SABRINA PETRUZZELLI, RAFFA ...
1996 Volume 49 Issue 3 Pages
263-266
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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The biological activities of karalicin, a new product from the
Pseudomonas fluorescens/
putida strain SS-3 (CCM 4430) are described.
It shows a weak, but specific and irreversible, antiviral activity on Herpes simplex viruses. It also presents some inhibitory activity on different species of yeasts.
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NORIKO TABATA, HIROSHI TOMODA, YUZURU IWAI, SATOSHI OMURA
1996 Volume 49 Issue 3 Pages
267-271
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Xanthoquinodin B3, a new component of anticoccidial xanthoquinodins, which was detected in the culture broth of
Humicola sp. FO-888, was isolated by heat treatment of the xanthoquinodins complex. Structural elucidation indicated that Xanthoquinodin B3 has the same heterodimer of xanthone- and anthraquinone-derived monomers as other xanthoquinodins. Schizont formation of monensin-resistant
Eimeria tenella in BHK-21 cells was inhibited by Xanthoquinodin B3 at concentrations greater than 0.035μM.
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GEOFF H. BAKER, SIMON E. BLANCHFLOWER, RODERICK J. J. DORGAN, JEREMY R ...
1996 Volume 49 Issue 3 Pages
272-280
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Ten novel α and β class milbemycins have been isolated and characterized from the
Streptomyces sp. E225, which has previously been shown to produce four related milbemycins. Some of the metabolites contain new structural features including, VM48641 which possesses an α-methoxyl substituent at C-27, and VM48642 which contains a furan ring at the terminus of the C-26 side chain. Several of these new compounds were shown to possess potent anthelmintic activity. An analysis of NMR chemical shift trends in this series of metabolites is presented.
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III. Optical Resolution of 3-Amino-2-hydroxyvaleric Acid and Absolute Configuration of Poststatin
MAKOTO TSUDA, YASUHIKO MURAOKA, MACHIKO NAGAI, TAKAAKI AOYAGI, TOMIO T ...
1996 Volume 49 Issue 3 Pages
281-286
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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3-Amino-2-hydroxyvaleric acid was prepared, and separated into its diastereomers. The relative stereochemistry was determined by
1H NMR in their oxazolidone derivatives. The
threo-isomer was resolved by (
S)-1-(1-naphthyl)ethylamine in the
N-(
p-methoxybenzyloxycarbonyl) derivative. The absolute configuration of (-)-
threo-3-(
p-methoxybenzyloxycarbonyl)amino-2-hydroxyvaleric acid was confirmed to be 2
R, 3
S. The absolute configuration of 3-amino-2-oxovaleric acid in poststatin was confirmed to be
S by comparison of the four stereoisomers of methyl
N,
O-bis(3, 5-dinitrobenzoyl)-3-amino-2-hydroxyvalerate derived from 3-amino-2-hydroxyvaleric acid and that derived from 3-amino-2-oxovaleryl moiety of poststatin by means of HPLC with chiral column.
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IV. The Chemical Synthesis of Poststatin
MAKOTO TSUDA, YASUHIKO MURAOKA, MACHIKO NAGAI, TOMIO TAKEUCHI, TAKAAKI ...
1996 Volume 49 Issue 3 Pages
287-291
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Total synthesis of poststatin was achieved by both liquid phase and solid phase methods. In both methods, the (2
R, 3
S)-3-amino-2-hydroxyvaleric acid moiety was incorporated into protected pentapeptides, and was oxidized to (
S)-3-amino-2-oxovaleric acid (postine). Deprotection of the oxidized pentapeptides gave a specimen identical with natural poststatin in physico-chemical properties and prolyl endopeptidase inhibitory activity.
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IV. Structure Elucidation of Pyripyropenes M to R
HIROSHI TOMODA, NORIKO TABATA, DA-JUN YANG, ICHIJI NAMATAME, HARUO TAN ...
1996 Volume 49 Issue 3 Pages
292-298
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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Six new pyripyropenes, M to R, were isolated from the ethyl acetate extracts of the jar fermentation broth of
Aspergillus fumigatus FO-1289-2501. Structural elucidation indicated that all the pyripyropenes have the same pyridino-α-pyrone sesquiterpene core as pyripyropenes A to L. Among them pyripyropene M showed the most potent inhibition against acyl-CoA: cholesterol acyltransferase activity with an IC
50 value of 3.80μM in rat liver microsomes, but pyripyropenes N to R showed moderate inhibitory activity (IC
50 11.0-78.0μM).
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III. Structural Elucidation
JOHN E. LEET, DANIEL R. SCHROEDER, JERZY GOLIK, JAMES A. MATSON, TERRE ...
1996 Volume 49 Issue 3 Pages
299-311
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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The structure of the antitumor antibiotic himastatin was determined using a combination of spectroscopic and chemical degradation techniques. Himastatin is a unique dimeric cyclohexadepsipeptide joined through a biphenyl linkage between two oxidized tryptophan units. The gross structure of the dimer was established through degradative ozonolysis. Himastatin consists of D-valine, D-threonine, L-leucine, L-α-hydroxyisovaleric acid, (3
R, 5
R)-5-hydroxypiperazic acid, and (2
R, 3a
R, 8a
R)-3a-hydroxyhexahydropyrrolo[2, 3
b]indole 2-carboxylic acid subunits.
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TOSHIHIRO KUNIGAMI, KAZUO SHIN-YA, KAZUO FURIHATA, KEIKO FURIHATA, YOI ...
1996 Volume 49 Issue 3 Pages
312-313
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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KOICHIRO TORIGOE, NAOMI WAKASUGI, NAMI SAKAIZUMI, TAKASHI IKEJIMA, HAJ ...
1996 Volume 49 Issue 3 Pages
314-317
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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XIAO-MEI HUANG, DOUGLAS M. REAMER, LAURA H. MILLER, HOWARD E. GRACEY, ...
1996 Volume 49 Issue 3 Pages
318-320
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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TAKAHIKO SATOH, YOSHIO NISHIMURA, SHINICHI KONDO, TOMIO TAKEUCHI, MASA ...
1996 Volume 49 Issue 3 Pages
321-325
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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TOSHIO TSUCHIDA, MAYA UMEKITA, NAOKO KINOSHITA, HIRONOBU IINUMA, HIKAR ...
1996 Volume 49 Issue 3 Pages
326-328
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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FRANK VANMIDDLESWORTH, JIM MILLIGAN, KEN BARTIZAL, CLAUDE DUFRESNE, JA ...
1996 Volume 49 Issue 3 Pages
329-331
Published: March 25, 1996
Released on J-STAGE: November 21, 2006
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