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MARTIN A. HAYES, STEPHEN K. WRIGLEY, IAN CHETLAND, ELWOOD E. REYNOLDS, ...
1996 Volume 49 Issue 6 Pages
505-512
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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A series of novel drimane sesquiterpene esters (
1-
6) was isolated from fermentations of
Aspergillus ustus var.
pseudodeflectus and their structures elucidated by spectroscopic methods including the HMQC, HMBC and INADEQUATE NMR experiments. The major component of the fermentation,
1, was (2'
E, 4'
E, 6'
E)-6-(r-carboxy-2', 4', 6'-trien)-9-hydroxydrim-7-ene-l 1, 12-olide. Compounds
1,
2,
3 and
5 exhibited endothelin receptor binding inhibitory activity against rabbit endothelin-A and rat endothelin-B receptors with IC
50 values in the range 20-150μM. These compounds had similar levels of activity in assays for binding to human endothelin A and endothelin B receptors. The isolation of 9, ll-dihydroxy-6-oxodrim-7-ene, 7, a probable biosynthetic precursor to the drimane esters is also reported.
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Production, Isolation, Structural Elucidation, and Biological Properties
SENJI TAKAHASHI, RYUJU HASHIMOTO, KUNIKATSU HAMANO, TOMOO SUZUKI, AKIR ...
1996 Volume 49 Issue 6 Pages
513-518
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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A new melanin biosynthesis inhibitor, melanoxazal, was isolated from the fermentation broth of
Trichoderma sp. ATF-451 by successive purification procedures of carbon adsorption, ethyl acetate extraction and silica gel column chromatography. The inhibitor possesses a novel oxazole-containing structure with molecular formula, C
8H
9NO
3. The structure was determined by means of NMR analyses to be (
E)-4-(2'-formyl-3'-hydroxybuten-r-yl) oxazole, which is related to melanoxadin. Melanoxazal inhibited melanin formation in the larval haemolymph of the silkworm,
Bombyx mori; IC
50 value=30.1 μg/ml. Melanoxazal also showed a strong inhibitory activity against mushroom tyrosinase with IC
50 value=4.2μg/ml.
View full abstract
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YANG CAI, ANDREAS FREDENHAGEN, PAUL HUG, THOMAS MEYER, HEINRICH H. PET ...
1996 Volume 49 Issue 6 Pages
519-526
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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From the Staurosporine producing strain R-19
Streptomyces longisporoflavus various minor metabolites were isolated: They include new compounds with a keto function at carbon 4' of Staurosporine and several metabolites related to TAN-1030A. The new structures were elucidated by spectroscopic methods, mainly
1H NMR and
13C NMR and by comparison with TAN-1030A. The new compounds inhibited protein kinase C with IC
50 values in the micromolar range with the exception of those compounds that are alkylated at the lactam nitrogen.
View full abstract
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I. Taxonomy, Fermentation, Isolation and Biological Properties
CHENG-BIN CUI, HIDEAKI KAKEYA, GEN OKADA, RIE ONOSE, HIROYUKI OSADA
1996 Volume 49 Issue 6 Pages
527-533
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Two novel diketopiperazines named tryprostatins A (
1) and B (
2) and a new natural product belonging to the diketopiperazine series, designated as demethoxyfumitremorgin C (
3), together with four known diketopiperazines, fumitremorgin C (
4), 12, 13-dihydroxyfumitremorgin C (
5), fumitremorgin B (
6) and verruculogen (
7), were isolated from the fermentation broth of
Aspergillus fumigatus BM939 by the combined use of solvent extraction, silica gel column chromatography, preparative TLC and repeated-preparative HPLC. The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4μM (
1), 4.4μM (
2), 0.45μM (
3), 4.1μM (
4), 60.8μKM (
5), 26.1 fiu (
6) and 12.2μM (
7), respectively.
View full abstract
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II. Physico-chemical Properties and Structures
CHENG-BIN CUI, HIDEAKI KAKEYA, HIROYUKI OSADA
1996 Volume 49 Issue 6 Pages
534-540
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Two novel diketopiperazines named tryprostatins A and B and a new natural product belonging to the diketopiperazine series, designated as demethoxyfumitremorgin C, together with four known diketopiperazines, fumitremorgin C, 12, 13-dihydroxyfumitremorgin C, fumitremorgin B and verruculogen, are new M phase inhibitors of the mammalian cell cycle, which were isolated from the secondary metabolites of
Aspergillus fumigatus. The structures of tryprostatins A, B and demethoxyfumitremorgin C were determined mainly by the use of spectroscopic methods especially by detailed analyses of their
1H and
13C NMR spectra with the aid of 2D NMR techniques including pulse field gradient heteronuclear multiple-bond correlation (PFG-HMBC) spectroscopy. Their absolute configurations were determined on the basis of the optical rotational values and CD spectra.
View full abstract
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GREGORY M. BRILL, WARREN M. KATI, DEBRA MONTGOMERY, JAMES P. KARWOWSKI ...
1996 Volume 49 Issue 6 Pages
541-546
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Two novel triterpene sulfates have been isolated from
Fusarium compactum by bioactivitydirected fractionation using an assay which measures the inhibition of proteolytic activity of rhino virus 3C protease on a fluorogenic peptide substrate. The compounds were purified by countercurrent and reverse phase chromatographies. NMR, MS, UV and IR studies revealed two triterpene sulfates, uncommon metabolites of terrestrial fungi.
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I. Taxonomy, Fermentation and Biological Activities
JESSICA A. GORMAN, LI-PING CHANG, JUNIUS CLARK, DONALD R. GUSTAVSON, K ...
1996 Volume 49 Issue 6 Pages
547-552
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Ascosteroside, a novel antifungal compound, was isolated from the culture broth of
Ascotricha amphitricha. This compound is an alpha-linked glycoside of a lanostane type triterpenoid. It is active against yeasts such as
Candida albicans and
Saccharomyces cerevisiae and against filamentous fungi but shows no activity against bacteria. It is not toxic to mammalian cells at concentrations up to ISOμM. In a mouse model, the compound afforded protection comparable to that of ketoconazole.
View full abstract
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II. Isolation and Structure Elucidation
JOHN E. LEET, STELLA HUANG, STEVEN E. KLOHR, KIMBERLY D. MCBRIEN
1996 Volume 49 Issue 6 Pages
553-559
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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The novel antifungal agent ascosteroside (
1) was isolated from cultured broth of
Ascotricha amphitricha (ATCC 74237). The structure based on spectroscopic data was determined to be an α-linked glycoside of a lanostane-type triterpenoid.
View full abstract
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Production, Physico-chemical and Biological Properties
KLAUS GERTH, NORBERT BEDORF, GERHARD HÖFLE, HERBERT IRSCHIK, HANS ...
1996 Volume 49 Issue 6 Pages
560-563
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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An antifungal activity against
Mucor hiemalis was detected in the culture broth of
Sorangium cellulosum (Myxococcales) strain So ce90. The activity was excreted into the supernatant during the log and early stationary phase. When the adsorber resin XAD-16 was added to the culture, the active metabolites were quantitatively bound to the resin. The epothilons showed a high cytotoxicity for animal cells and mimic the biological effects of taxol (BOLLAG
et al., Cancer Res. 55: 2325-2333, 1995).
View full abstract
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TOMIO MORINO, KEI-ICHI SHIMADA, AKIRA MASUDA, NORIYUKI YAMASHITA, MASA ...
1996 Volume 49 Issue 6 Pages
564-568
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Structures of novel immunosuppressants, stevastelin A, B and B3
1) were determined by their spectroscopic and chemical studies. Three stevastelins were shown to be cyclic depsipeptides composed of a fatty acid and three amino acid moieties. The sequence of these moieties was determined to be as 3, 5-dihydroxy-2, 4-dimethylstearylvalylthreonyl (or
O-sulfonylthreonyl in stevastelin A)-
O-acetylserine. Cyclic structures were shown to be formed by ester linkages between the carboxylic group of the
O-acetylserine moiety and the 5-hydroxy group of the fatty acid moiety in stevastelin A and B, and the 3-hydroxy group of the fatty acid moiety in stevastelin B3.
View full abstract
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KEI-ICHI SHIMADA, TOMIO MORINO, AKIRA MASUDA, MASAYA SATO, MASAYUKI KI ...
1996 Volume 49 Issue 6 Pages
569-574
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Stevastelin B, obtained from a culture of a
Penicillium sp. NK374186, is a novel depsipeptide containing three amino acids and 3, 5-dihydroxy-2, 4-dimethylstearic acid. The stereochemistry of the three amino acids was determined by HPLC analysis, and the relative configuration of the 3, 5-dihydroxy-2, 4-dimethylstearic acid was elucidated by chemical conversion and NMR analysis. The absolute stereochemistry of Stevastelin B was determined by synthetic methods.
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ROBIN D. G. COOPER, NANCY J. SNYDER, MARK J. ZWEIFEL, MICHAEL A. STASZ ...
1996 Volume 49 Issue 6 Pages
575-581
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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Reductive alkylation of the A82846 family of glycopeptide antibiotics has the potential of producing seven products.
N-Alkylation of the disaccharide amino function can be accomplished selectively, and offers the greatest increase in antibacterial activity. Products resulting from
N-alkylation of LY264826 (A82846B) provide the most potent derivatives as compared to other members of this class of antibiotics. Two of these derivatives, LY307599 and LY333328 are approximately 500 times more active than vancomycin against vancomycin-resistant enterococci.
View full abstract
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I. Synthesis of 4-O-Alkyl-L-cladinose Analogues via Glycosylation
KEN-ICHI KURIHARA, KEIICHI AJITO, SEIJI SHIBAHARA, TSUNEO ISHIZUKA, OS ...
1996 Volume 49 Issue 6 Pages
582-592
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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The synthesis and biological evaluation of sixteen-membered macrolides possessing a 4-
O-alkyl-α-L-cladinosyl moiety as the neutral sugar are described. The nine novel derivatives have been synthesized by glycosylation with 1-thio sugars. The most active derivative of them showed prolonged antibacterial activity in rat plasma
in vitro and improved pharmacokinetics.
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SUSANNE GRABLEY, RALF THIERICKE, M. ZERLIN, AXEL GÖHRT, SIEGRID P ...
1996 Volume 49 Issue 6 Pages
593-595
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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RANDAL H. CHEN, SHAUN TENNANT, DAVID FROST, MICHAEL J. O'BEIRNE, JAMES ...
1996 Volume 49 Issue 6 Pages
596-598
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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EMIKO MAGOME, KENZO HARIMAYA, SHUICHI GOMI, MASAO KOYAMA, NORIKO CHIBA ...
1996 Volume 49 Issue 6 Pages
599-602
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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HIROSHI NOUDA, HARUKI MATSUMURA, TOMOHARU TANIO, MAKOTO SUNAGAWA
1996 Volume 49 Issue 6 Pages
603-606
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
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ANGELO BORGHI, FRANCA SPREAFICO, GRAZIA BERETTA, PIETRO FERRARI, BETH ...
1996 Volume 49 Issue 6 Pages
607-609
Published: June 25, 1996
Released on J-STAGE: November 21, 2006
JOURNAL
FREE ACCESS