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SHINICHIRO TOKI, KATSUAHIKO ANDO, MAYUNI YOSHIDA, YUZURU MATSUDA
1994 Volume 47 Issue 11 Pages
1175-1181
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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A novel compound, PS-990, which induces differentiation of neuroblastoma cells, was isolated from the culture broth of a fungus,
Acremonuim sp. KY12702. PS-990 inhibited brain calcium/calmodulin-dependent cyclic nucleotide phosphodiesterase with an IC
50 value of 3μg/ml, and markedly induced neurite extension of mouse neuroblastoma, Neuro2A, at concentrations ranging from 10 to 30μg/ml.
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COLIN J. BAROW, DAVID M. SEDLOCK, HAO H. SUN, RAYMOND COOPER, AMANDA M ...
1994 Volume 47 Issue 11 Pages
1182-1187
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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WIN 66306 (
1a), a cyclic peptide containing a novel amino acid, was isolated as a neurokinin antagonist from an
Aspergillus species, labelled SC230. Conditions that maximized the production of
1a were developed, leading also to production of the related compound WIN 68577 (
2) and rosellichalasin (
3). Both
2 and
3 were more active in the rat NK1 than in the human NK1 receptor binding assay, while
1a was more active at the human receptor with an inhibitor affinity constant of 7 μm.
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WOLFGANG WEBER, PETER SCHU, TIMM ANKE, ROBERT VELTEN, WOLFGANG STEGLIC ...
1994 Volume 47 Issue 11 Pages
1188-1194
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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A new salicylic acid derivative, caloporoside, was isolated from fermentations of
Caloporus dichrous. Its structure was elucidated by a combination of chemical and spectroscopic methods. Caloporoside exhibits weak antibacterial and antifungal activities and is a quite selective inhibitor of phospholipase C isolated from pig brain (
Ki 12, 3μm).
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M. ESTELA ALVAREZ, DAVID R. HOUCK, CAROLE B. WHITE, JAMES E. BROWNELL, ...
1994 Volume 47 Issue 11 Pages
1195-1201
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Two new peptides, a diketopiperazine of
N-methyltyrosine (
1) and a tetrapeptide containing
N-methyltyrosine (
2), were isolated from an actinomycete strain
Streptomyces griseujs. These compounds inhibit the enzyme calpain in the micromolar range and were characterized on the basis of spectroscopic analysis, amino acid analysis and sequencing. The structure of the tetrapeptide
N-methyltyrosyl-
N-methyltyrosyl-leucyl-alanine (
2), was also confirmed by total synthesis.
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YASUNORI FUNABASHI, TAKASHI HORIGUCHI, SHIGEMI IINUMA, SEIICHI TANIDA, ...
1994 Volume 47 Issue 11 Pages
1202-1218
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Fungal metabolites with an
epi-oligothiadiketopiperazine structure, TAN-1496 A, C and E, were isolated from the culture broth of
Microsphaeropsis sp. FL-16144. Their molecular formulas were determined to be C
22H
28N
2O
9S
2, C
22H
28N
2O
9S
3 and C
22H
28N
2O
9S
4, respectively. Structures were determined by comparing the NMR data with those of known diketopiperazine antibiotics, sirodesmins. These metabolites inhibited the relaxation of supercoiled pBR322 DNA by calf thymus topoisomerase I but did not affect the decatenation of kinetoplast DNA by calf thymus topoisomerase II at concentration up to 500μM. They strongly suppressed the growth of various murine and human tumor cells and induced apoptosis. Moreover, various derivatives were synthesized to investigate the relationship of their functional groups and biological activities.
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KEN ISHIGAMI, YOICHI HAYAKAWA, HARUO SETO
1994 Volume 47 Issue 11 Pages
1219-1225
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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In the course of our screening for antitumor antibiotics which show biological activities by generating active oxygen in tumor cells,
Micromonospora sp. JY16 was found to produce a new anthracycline antibiotic designated cororubicin. The structure of cororubicin was elucidated as shown in Fig. 5 on the basis of NMR spectral analysis. Cororubicin generated superoxide radicals in tumor cells and showed cytotoxicity, which was reduced by addition of an antioxidative agent, dithiothreitol (DTT).
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MITSUKO SEKI-ASANO, TADAYASU OKAZAKI, MICHIO YAMAGISHI, NORIYOSHI SAKA ...
1994 Volume 47 Issue 11 Pages
1226-1233
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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New 18-membered macrolides FD-891 and FD-892 were discovered from the fermentation broth of
Streptomyces graminofaciens A-8890 isolated from a soil sample collected at Yamanashi prefecture, Jpan. They induce morophological changes of HL-60 cells at low concentration below IC
5Os and have cytocidal activity against
in vitro tumor cell lines. FD-891 showed 2-7 times stronger activity than doxorubicin whereas FD-892 was 20 - 100 fold weaker than FD-891 and doxorubicin.
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MITSUKO SEKI-ASANO, YUKIKO TSUCHIDA, KAZUNORI HANADA, KAZUTOSHI MIZOUE
1994 Volume 47 Issue 11 Pages
1234-1241
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Structures of FD-891 and FD-892 were determined by extensive NMR spectral analysis as shown in Fig. 1. They belong to such 18-membered macrolides as concanamycins and virusto-mycin.
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PHYSICO-CHEMICAL PROPERTIES AND STRUCTURES
CHIKA TAKAHASHI, ATSUSHI NUMATA, EIKO MATSUMURA, KATSUHIKO MINOURA, HI ...
1994 Volume 47 Issue 11 Pages
1242-1249
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Leptosins I and J, belonging to a series of epipolythiodioxopiperazines, have been isolated from the mycelium of a strain of
Leptosphaeria sp. OUPS-4 attached to the marine alga
Sargasssum tortile. Their relative stereostructures have been elucidated by chemical and spectral evidence. These compounds exhibited significant cytotoxic activity against cultured P388 cells.
View full abstract
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I. ISOLATION AND STRUCTURE DETERMINATION
WEIDONG DING, DAVID R. WILLIAMS, PETER NORTHCOTE, MARSHALL M. SIEGEL, ...
1994 Volume 47 Issue 11 Pages
1250-1257
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Pyrroindomycins A and B were isolated from fermentations of culture LL-42D005, a strain of
Streptomyces rugosporus. Pyrroindomycins possess potent antimicrobial activities against methicillin-resistant
Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococci. Their structures have been determined by using 1- and 2-D NMR, mass spectroscopy and chemical degradations. Pyrroindomycins are the first natural products that contain the highly unsaturated pyrroloindole moiety.
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II. BIOLOGICAL ACTIVITIES
MAYA P. SINGH, PETER J. PETERSEN, NILDA V. JACOBUS, MARY JO MROCZENSKI ...
1994 Volume 47 Issue 11 Pages
1258-1265
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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The pyrroindomycins, a complex of novel antibiotics identified in fermentation broths of "
Streptomyces rugosporus" LL-42D005, demonstrated excellent
in vitro activity against Gram-positive bacteria. The semisynthetic diacetyl derivative of pyrroindomycin B (pyrroindomycin B-Ac
2) was bactericidal for exponential-phase cells, but not for stationary-phase cells. This compound also exhibited marginal protection against a lethal
Staphylococcus aureus challenge in mice. The poor
in vivo activity of this antibiotic complex may be related to binding to blood components, as suggested by elevated MICs observed in blood-containing media. Incorporation of radiolabeled precursors into DNA, RNA, and protein was inhibited in an exponential-phase culture of
Bacillus subtilis within ten minutes of exposure to pyrroindomycin B-Ac
2. Microscopic examinations of drug-treated cells revealed lysis within the same ten minute period. These data are consistent with an effect of pyrroindomycin B-Ac
2 on the integrity of the bacterial membrane.
View full abstract
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I. TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL AND BIOLOGICAL PROPERTIES
RYUICHI SAWA, YOSHIKAZU TAKAHASHI, SAKIKO ITOH, KAZUO SHIMANAKA, NAOKO ...
1994 Volume 47 Issue 11 Pages
1266-1272
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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A new antibiotic, aldecalmycin, has been discovered in the culture broth of
Streptomyces sp. MJ147-72F6. Aldecalmycin was purified by solvent extraction, Diaion HP-20 chromatography, silica gel chromatography, Sephadex LH-20 chromatography, HPLC and centrifugal partition chromatography. The
1H and
13C NMR spectra of aldecalmycin showed the presence of keto-enol tautomers. Aldecalmycin is equipotent in inhibiting the growth of sensitive and methicillin-resistant
Staphylococcus aureus (MRSA).
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II. STRUCTURE ELUCIDATION BY NMR STUDIES
RYUICHII SAWA, YOSHIKAZU TAKAHASHI, TSUTOMU SAWA, HIROSHI NAGANAWA, TO ...
1994 Volume 47 Issue 11 Pages
1273-1279
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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A new antibiotic, aldecalmycin (
1) was isolated from the culture broth of
Streptomyces sp. MJ147-72F6. The
1H and
13C NMR spectra of
1 were complicated due to the presence of a β-ketoaldehyde moiety. Therefore,
1 was converted into an ethylene ketal derivative (
2) and into a dihydroaldecalmycin (
3). These derivatives gave assignable NMR spectra. The planar structure was elucidated by using
1H-
1H COSY, 2D-HOHAHA,
1H-
13C COSY and HMBC spectra of
2. The conformation of the decalin ring was elucidated by using 1D-HOHAHA, NOE difference and NOESY spectra of
3. The geometry of double bond in the side chain was determined by NOE difference and NOESY spectra of
3.
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III. DETERMINATION OF ABSOLUTE CONFIGURATION
RYUICHI SAWA, YOSHIKAZU TAKAHASHI, HIKAMURA NAKAMURA, KAZUO T. NAKAMUR ...
1994 Volume 47 Issue 11 Pages
1280-1283
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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The planar structure of aldecalmycin (
1) had been determined in the previous paper, together with the conformations of the substituted
trans decalin ring having one double bond and the sugar; β-glucopyranoside type. The absolute configuration of
1 was a following problem to be solved. X-Ray crystallographic analysis of crystalline 4', 6'-
O-benzylidenedihydroaldecalmycin (
4) revealed the relative configuration. On the other hand, the stereoisomerism of the sugar was determined to be d by the optical rotation value of tetra-
O-acetyl-α-methylglucopyranoside derived from
1. These results established the absolute configuration of
1.
View full abstract
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I. PRODUCING ORGANISM, FERMENTATION, ISOLATION, AND BIOLOGICAL ACTIVITIES
MARC STADLER, HEIDRUN ANKE, OLOV STERNER
1994 Volume 47 Issue 11 Pages
1284-1289
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Six new bisabolane type sesquiterpenoids, cheimonophyllons A (
1), B (
2), C (
3), D (
4), E (
5), and cheimonophyllal (
6) were isolated from the culture fluid of the basidiomycete,
Cheimonophyllum candidissimum. The compounds exhibited nematicidal, weak antifungal and antibacterial as well as cytotoxic activities. The main product, cheimonophyllon A (
1) (C
15H
22O
4), was also active in the Ames mutagenicity test.
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T. S. CHEN, B. PETUCH, J. MACCONNELL, R. WHITE, G. DEZENY, B. ARISON, ...
1994 Volume 47 Issue 11 Pages
1290-1294
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Zaragozic acid A analogues are produced by an unidentified sterile fungus when it is exogenously supplied with 2-thiophenecarboxylic acid, 3-thiophenecarboxylic acid, 2-furoic acid, 2-fluorobenzoic acid, 3-fluorobenzoic acid, or 4-fluorobenzoic acid. The analogues carry 2-thiophenyl, 3-thiophenyl, 2-furyl,
o-fluorophenyl,
m-fluorophenyl, or
p-fluorophenyl group, respectively, at C-6' of the C-1 alkyl side chain replacing the phenyl group of natural zaragozic acid A. All the new analogues of zaragozic acid A possess picomolar inhibitory activity against squalene synthase
in vitro.
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S. CHAND, I. LUSUNZI, D. A. VEAL, L. R. WILLIAMS, P. KARUSO
1994 Volume 47 Issue 11 Pages
1295-1304
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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A spectrophotometric method has been developed for the rapid measurement of the antimicrobial activity of natural products, including crude extracts or pure materials. The assay depends on the measurement of non-specific esterase activity using fluorescein diacetate (FDA) hydrolysis in broth cultures of microbes after they have been treated with test compounds. The assay is accurate, reproducible and economical in both time and materials. The speed and economy of the method make it suitable for the rapid screening of many samples and the bioassay directed purification of antimicrobial substances. The assay can also be used with a wide variety of micro-organisms since most micro-organisms are FDA positive. Applications are described in the fields of marine natural products chemistry and essential oils research.
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MASARU KAMISHOHARA, HIROYUKI KAWAI, ATSUO ODAGAWA, TOSHIYUKI ISOE, JUN ...
1994 Volume 47 Issue 11 Pages
1305-1311
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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The antitumor activity of spicamycin analogue SPM VIII against human stomach, breast, lung, colon and esophageal cancers was compared to that of mitomycin C (MMC) in the human tumornude mice xenograft model. Comparative studies of SPM VIII given iv at 6mg/kg/day daily for 5 days and MMC given iv at 6.7mg/kg on day 1 revealed that the antitumor spectrum of SPM VIII showed a different pattern from that of MMC and that SPM VIII caused tumor mass reductions in more tumors than did MMC in colon cancers (4/12 versus 1/11). In addition to this study, a comparative study of SPM VIII given iv at 12mg/kg/day 8 times at 3- or 4-day intervals and 5'-deoxy-5-fluorouridine (5'-DFUR) given po at 185mg/kg/day 5 days per week for 4 weeks showed that SPM VIII had the highest effect on SC-9 human stomach cancer and COL-1 human colon cancer among the 3 compounds, resulting in a significant reduction of tumor mass. Although other pharmacological studies are in progress, these results suggest that SPM VIII might be a novel antitumor compound effective for human cancers including cancer of the digestive organs.
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THEIR SYNTHESIS AND ANTITUMOR ACTIVITY
HITOSHI ARAI, YUTAKA KANDA, TADASHI ASHIZAWA, MAKOTO MORIMOTO, KATSUSH ...
1994 Volume 47 Issue 11 Pages
1312-1321
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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A series of mitomycin derivatives
1-
3 having unique condensed-ring structures was synthesized and evaluated for their anticellular and antitumor activity. These compounds were synthesized by the Michael addition of 1, 3-dicarbonyl compounds to 6-demethyl-7, 7-(ethylenedioxy)-6, 7-dihydro-6-methylenemitosanes (
4-
6, and
14) and the subsequent cyclization. For the preparation of
1, the allyloxycarbonyl (Aloe) group was employable for the protection of the aziridine (1a-
N-H), since the deprotection proceeded without decomposition of the substrates under the mild conditions with Pd(0) and HCO
2H-NEt
3. Among these structurally unique derivatives, compounds
1a,
1b,
1d and
1e were quite potent against HeLa S
3 human tumor cells and sarcoma 180 solid tumor in mice.
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FRED E. BUTTON, STEPHEN J. NELSON
1994 Volume 47 Issue 11 Pages
1322-1327
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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Anthelmintic cyclodepsipeptide PF1022A has been prepared in eleven steps from
N-Boc-
N-methyl-L-leucine, benzyl 3-phenyl-D-lactate and benzyl D-lactate.
View full abstract
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YUE-ZHONG SHU, MAREDITH ARCURI, MICHAEL R. KOZLOWSKI, RICHARD R. WANG, ...
1994 Volume 47 Issue 11 Pages
1328-1332
Published: November 25, 1994
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BEOM TAB KIM, JAE YONG LEE, YOUN YOUNG LEE, OK YUN KIM, JEONG HO CHU, ...
1994 Volume 47 Issue 11 Pages
1333-1336
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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MAKOTO SUNAGAWA, AKIRA SASAKI, HIROSHI YAMAGA, HISATOSHI SHINAGAWA, YO ...
1994 Volume 47 Issue 11 Pages
1337-1340
Published: November 25, 1994
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TOMIO MORINO, AKIRA MASUDA, MASATOSHI YAMADA, MASAKAZU NISHIMOTO, TAKA ...
1994 Volume 47 Issue 11 Pages
1341-1343
Published: November 25, 1994
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YOICHI HAYAKAWA, KEN ISHIGAMI, KAZUO SHIN-YA, HARUO SETO
1994 Volume 47 Issue 11 Pages
1344-1347
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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DAWIT ABATE, WOLF-RAINER ABRAHAM
1994 Volume 47 Issue 11 Pages
1348-1350
Published: November 25, 1994
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RYUICHI SAWA, YOSHIKAZU TAKAHASHI, MASA HAMADA, TSUTOMU SAWA, HIROSHI ...
1994 Volume 47 Issue 11 Pages
1351-1353
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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MAKOTO SUNAGAWA, AKIRA SASAKI, HIROSHI YAMAGA, HISATOSHI SHINAGAWA, MA ...
1994 Volume 47 Issue 11 Pages
1354-1358
Published: November 25, 1994
Released on J-STAGE: April 19, 2006
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