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CHIKARA SHINOHARA, KEIJI HASUMI, WATARU HATSUMI, AKIRA ENDO
1996 Volume 49 Issue 10 Pages
961-966
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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A novel triprenyl phenol, designated staplabin, has been isolated from a culture of
Stachybotrys microspora IFO 30018 by solvent extraction and successive chromatographic fractionation using silica gel, Sephadex LH-20 and silica ODS columns. By a combination of spectroscopic analyses, the structure of staplabin is proposed to be 5-(2-(5, 7-dihydroxy-8-methyl-8-(4, 8-dimethyl-3, 7-nonadienyl)-3-oxo-7, 8-dihydro-6
H-pyrano[2, 3-e][1, 3]dihydroisoindolyl)pentanoic acid. Staplabin stimulated the binding of plasminogen, the zymogen of the fibrinolytic serine protease plasmin, to both fibrin and U937 cells. Binding was elevated 2-fold at a concentration of 0.3-0.5mM.
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ROBERT R. WEST, JEFFREY VAN NESS, ANNE-MARIE VARMING, BIRGITTE RASSING ...
1996 Volume 49 Issue 10 Pages
967-973
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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A novel inhibitor of platelet-activating factor (PAF) acetyltransferase, an essential enzyme in the remodeling pathway of platelet-activating factor synthesis, was identified by a high throughput screen of natural product extracts of microbial origin. The compound, ZG-1494α, was isolated from an ethyl acetate extract of a culture broth of
Penicillium rubrum through bioassay guided fractionation. The structure of ZG-1494α was determined by spectroscopic methods. A key feature of the structure, which is relatively rare among natural products, is the 5-hydroxy-3-pyrrolin-2-one moiety. A
13C-
13C INADEQUATE was utilized to unambiguously determine the regiochemistry of this molecule.
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I. Taxonomy, Fermentation, Isolation and Biological Activities
YOICHI HAYAKAWA, KIN-YA SOHDA, KEIKO FURIHATA, TOMOHISA KUZUYAMA, KAZU ...
1996 Volume 49 Issue 10 Pages
974-979
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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The retinoblastoma protein (pRB) is inactivated in a wide variety of human cancers. In the course of our screening for antitumor antibiotics by using pRB-inactivated cells, an actinomycete identified as
Streptomyces tanashiensis was found to produce four new active substances, leptofuranins A, B, C and D. The leptofuranins arrested the growth of normal cells and induced apoptotic cell death against tumor cells and cells transformed with the adenovirus E1A gene.
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II. Physicochemical Properties and Structure Elucidation
YOICHI HAYAKAWA, KIN-YA SOHDA, HARUO SETO
1996 Volume 49 Issue 10 Pages
980-984
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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The structures of new antitumor antibiotics, leptofuranins A, B, C and D were elucidated to be as shown in Fig. 1 by NMR spectral analysis including a variety of two-dimensional techniques. The leptofuranins are novel leptomycin-related substances containing a tetrahydrofuran ring. Leptofuranins C and D were revealed to be in tautomeric isomerism and their relative stereochemistries were analyzed by NOESY experiments.
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Taxonomy, Isolation, Physico-chemical Properties, Structure and Biological Properties
A. MIKAMI, T. OKAZAKI, N. SAKAI, T. ICHIHARA, K. HANADA, K. MIZOUE
1996 Volume 49 Issue 10 Pages
985-989
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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During our screening program of natural products from fungal metabolites for drugs effective against tumor cell lines, we discovered a new isopatulin derivative, pintulin, from the fermentation broth of
Penicillium vulpinum F-4148. Pintulin shows weak activity against tumor cell lines, compared to that of adriamycin.
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JINGFANG QIAN-CUTRONE, STELLA HUANG, LI-PING CHANG, DOLORES M. PIRNIK, ...
1996 Volume 49 Issue 10 Pages
990-997
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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During the screening of the natural products for their ability to inhibit the binding of REV (regulation of virion expression) protein to [
33P] labeled RRE (REV responsive element) RNA, two novel fungal metabolites, harziphilone and fleephilone, were isolated from the butanol - methanol (1:1) extract of the fermentation broth of
Trichoderma harzianum by bioassay guided fractionation. The structures of these two new compounds were established by spectroscopic methods. Harziphilone and fleephilone showed inhibitory activity against the binding of REV-protein to RRE RNA with IC50 values of 2.0μM and 7.6μM, respectively. However both compounds did not protect CEM-SS cells from acute HIV infection at concentration levels up to 200μg/ml using an XTT dye reduction assay. In addition, harziphilone demonstrated cytotoxicity at 38μM against the murine tumor cell line M-109.
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CHORYU CHEN, NOBUTAKA IMAMURA, MIYUKI NISHIJIMA, KYOKO ADACHI, MIHO SA ...
1996 Volume 49 Issue 10 Pages
998-1005
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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Novel antimicroalgal substances halymecins A (
1), B (
2) and C (
3) were isolated from the fermentation broth of a
Fusarium sp. and halymecins D (
4) and E (
5) from an
Acremonium sp. The structures of these halymecins, Fig. 1, were determined based on extensive 2D NMR studies as well as mass spectral data. These chemical structures are conjugates of di- and trihydroxydecanoic acid. Halymecin A showed antimicroalgal activity against
Skeletonema costatum.
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M. S. Kuo, V. H. WILEY, J. I. CIALDELLA, D. A. YUREK, H. A. WHALEY, V. ...
1996 Volume 49 Issue 10 Pages
1006-1013
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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This report describes the results of a biosynthesis study of marcfortine A (MA). We report here that MA is derived from methionine, tryptophan, lysine and two isoprene units, the latter two being derived from acetic acid. From the
13C enrichment pattern of the pipecolic acid moeity we further conclude that this unit is derived from lysine
via α-ketoglutarate. Therefore, we have accounted for the biogenesis of every carbon atom of MA and established the biosynthetic pathway for the pipecolic acid moiety of MA.
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JUSTIN BRYANS, PETER CHARLTON, INÊS CHICARELLI-ROBINSON, MARK CO ...
1996 Volume 49 Issue 10 Pages
1014-1021
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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Two diketopiperazines, XR334 (
1) and the novel compound XR330 (
2), were isolated from the lyophilised biomass of an unidentified
Streptomyces sp. Their structures were elucidated on the basis of spectroscopic studies and confirmed by chemical synthesis. Both compounds inhibited plasminogen activator inhibitor-1 activity in an amidolytic assay of tissue plasminogen activator mediated plasmin generation. Compound 1 also enhanced fibrinolysis
ex vivo and protected against thrombus formation in the rat. These diketopiperazines represent the first low molecular weight inhibitors of plasminogen activator inhibitor-1, a physiological regulator of fibrinolysis
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VIII. Endopeptidase Inhibitory Activity of Non-peptidyl Poststatin Analogues
MAKOTO TSUDA, YASUHIKO MURAOKA, MACHIKO NAGAI, TAKAAKI AOYAGI, TOMIO T ...
1996 Volume 49 Issue 10 Pages
1022-1030
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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Non-peptidyl poststatin analogues, (S)-N-substituted-2-[2-1-acylpyrrolidinyl)]-2-oxoacetamides were synthesized and examined for their inhibitory activity against prolyl endopeptidase and cathepsin B
in vitro. Many compounds showed stronger activity than natural poststatin, a pentapeptide. Among them, (S)-N-cyclohexyl-2-oxo-2-[2-(1-(3-phenoxybenzoyl)pyrrolidinyl)]acetamide (
22) and (S)-N-cyclohexyl-2-[2-(1-(2-naphthoyl)pyrrolidinyl)]-2-oxoacetamide (
19) indicated IC
50 value of 5.8 and 8.2ng/ml for prolyl endopeptidase inhibition respectively. None of these compounds possess significant inhibitory activities against cathepsin B, a cysteine protease. These results indicate that these compounds are more selective inhibitors against prolyl endopeptidase than is natural poststatin.
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MAKOTO TSUDA, YASUHIKO MURAOKA, TOMIO TAKEUCHI, RYUICHI SEKIZAWA, KAZU ...
1996 Volume 49 Issue 10 Pages
1031-1035
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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(2S, 3R)-3-Amino-2-hydroxyoctanoic acid was synthesized by Curtius rearrangement of an azide derivative of (S)-malic acid. Total syntheses of valinoctin A and its analogues were achieved by a coupling of (2S, 3R)-3-amino-2-hydroxyoctanoic acid moiety with L-valine or several other amino acids moieties. 2S configuration of 3-amino-2-hydroxyoctanoic acid moiety was found to be important for the inhibitory activity and the L-valine moiety of valinoctin A was exchangeable with other L-amino acids.
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CYRILLE GRANDJEAN, GABOR LUKACS
1996 Volume 49 Issue 10 Pages
1036-1043
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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9-
O-Glycosyloxime derivatives of erythromycin A have been synthesized and their
in vitro antibacterial activity compared with that of erythromycin A (
1). This new class of macrolide antibiotics showed reduced antibacterial spectrum. However, some derivatives were as or more active than erythromycin A (
1) against strains, responsible for respiratory track infections, such as
Haemophilus influenzae,
Moraxella catarrhalis or
Streptococcus pneumoniae.
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STEVEN A. FISH, ERIC CUNDLIFFE
1996 Volume 49 Issue 10 Pages
1044-1048
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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The effects of tylosin-related macrolide antibiotics were examined in cell-free protein synthesis (using a coupled transcription-translation system derived from
Streptomyces lividans) and against whole cells of that organism. Anti-ribosomal potency was determined primarily by the number and nature of the glycosyl substituents, and was not significantly influenced by lactone ring oxidation or sugar methylation. In contrast, uptake of the drugs into
S. lividans was influenced, either positively or negatively, by each of these structural parameters. The presence of
erm type I or
erm type II resistance genes in
S. lividans markedly affected the resistance phenotype and studies involving ribosomes from such strains revealed differences in macrolide activity that were not otherwise apparent.
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TOMIO MORINO, KEI-ICHI SHIMADA, AKIRA MASUDA, MASAKAZU NISHIMOTO, SEII ...
1996 Volume 49 Issue 10 Pages
1049-1051
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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AKIRA URAKAWA, TORU SASAKI, KEN-ICHIRO YOSHIDA, TOSHIO OTANI, YU LEI, ...
1996 Volume 49 Issue 10 Pages
1052-1055
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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YOSHITAKE TANAKA, KEIICHI MATSUZAKI, CHONG-LIN ZHONG, HIROSHI YOSHIDA, ...
1996 Volume 49 Issue 10 Pages
1056-1059
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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Proposal for Biosynthetic Intermediates of K-252a
YANG CAI, ANDREAS FREDENHAGEN, PAUL HUG, HEINRICH H. PETER
1996 Volume 49 Issue 10 Pages
1060-1062
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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JUN KOHNO, NORIAKI KAMEDA, MAKI NISHIO, AKIO KINUMAKI, SABURO KOMATSUB ...
1996 Volume 49 Issue 10 Pages
1063-1065
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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GORJANA LAZAREVSKI, GABRIJELA KOBREHEL, BISERKA METELKO, HELMUT DUDDEC ...
1996 Volume 49 Issue 10 Pages
1066-1069
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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RINTARO YAMADA, MINORU SETO, YASUHARU SASAKI, TOSHIAKI SUNAZUKA, YOSHI ...
1996 Volume 49 Issue 10 Pages
1070-1072
Published: October 25, 1996
Released on J-STAGE: November 21, 2006
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