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SATOSHI OMURA, YASUHARU SASAKI, YUZURU IWAI, HIDEO TAKESHIMA
1995 Volume 48 Issue 7 Pages
535-548
Published: July 25, 1995
Released on J-STAGE: April 19, 2006
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HARUO IKEDA, SATOSHI OMURA
1995 Volume 48 Issue 7 Pages
549-562
Published: July 25, 1995
Released on J-STAGE: April 19, 2006
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HORST KLEINKAUF, HANS VON DÖHREN
1995 Volume 48 Issue 7 Pages
563-567
Published: July 25, 1995
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A. MARTYN AINSWORTH, M. INÊS CHICARELLI-ROBINSON, BRENT R. COPP, ...
1995 Volume 48 Issue 7 Pages
568-573
Published: July 25, 1995
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Xenovulene A, a novel inhibitor of benzodiazepine binding to the GABA-benzodiazepine receptor is produced by submerged fermentation of
Acremonium strictum. It was isolated from the mycelium by solvent extraction and purified by chromatography on Sephadex LH-20 and octadecyl silica. The structure of xenovulene A was determined to be a novel oxygenated sesquiterpene containing a humulene moiety by interpretation of various spectroscopic data, especially from 2D NMR experiments. Xenovulene A inhibited binding of the benzodiazepine, flunitrazepam, with an IC
50 of 40nM in an
in vitro assay using bovine synaptosome membrane preparations.
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KAZUO SHIN-YA, SHINTARO SHIMIZU, TOSHIHIRO KUNIGAMI, KEIKO FURIHATA, K ...
1995 Volume 48 Issue 7 Pages
574-578
Published: July 25, 1995
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A new neuronal cell protecting substance, lavanduquinocin was isolated from
Streptomyces viridochromogenes 2942-SVS3. It consists of a carbazole skeleton with an
ortho quinone function and a cyclolavandulyl moiety. Lavanduquinocin protected neuronal hybridoma N18-RE-105 cells from L-glutamate toxicity with EC
50 value 15.5nM.
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MASAYUKI TAKIZAWA, TSUNEAKI HIDA, TAKASHI HORIGUCHI, AKIKO HIRAMOTO, S ...
1995 Volume 48 Issue 7 Pages
579-588
Published: July 25, 1995
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The microbial lipopeptides, TAN-1511 A, B and C, were isolated from the culture broth of
Streptosporangium amethystogenes subsp.
fukuiense AL-23456. Their structures were elucidated on the basis of their reactions and spectroscopic analyses. These lipopeptides were mixtures of molecules having different lengths of fatty acids.
The metabolites stimulated the proliferation of bone marrow cells from BALB/c female mice at very low concentrations (concentration giving 30% increase: A and B, 0.313 ng/ml; C, 1.25 ng/ml). We confirmed that chemically synthesized TAN-1511 A analogue [(2
R, 6
R)-2-tetradecanoylamino6, 7-bis(hexadecanoyloxy)-4-thiaheptanoyl-Gly-Gly-Gly-Glu-Thr-Thr-OH] stimulated the proliferation of bone marrow cells in a manner similar to that of natural TAN-1511 A. This analogue induced the secretion of both granulocyte colony stimulating factor (G-CSF) and granulocyte-macrophage colony stimulating factor (GM-CSF), and potentiated the generation of Gr-1 positive cells in the bone marrow cell culture. Moreover, it effected the G-CSF mediated restoration of granulocytopoiesis in a murine leukopenia model.
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TSUNEAKI HIDA, KOZO HAYASHI, KOICHI YUKISHIGE, SEIICHI TANIDA, NORIAKI ...
1995 Volume 48 Issue 7 Pages
589-603
Published: July 25, 1995
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TAN-1511 analogues were synthesized and their effects on the proliferation of bone marrow cells were examined. To exert potent activity the following conditions are necessary: the configuration of the 2-amino-6, 7-dihydroxy-4-thiaheptanoic acid moiety must be (2
R, 6
R), long chain acyl groups (C
14 to C
18) must be bound to both hydroxyl groups, the amino group must be free or acylated with the long chain fatty acid (
ca. C
14) and the pep tide moiety must have glutamic acid as a component. Among the synthesized compounds, trisodium (2
R, 6
R)-2-amino-6, 7-bis (hexadecanoyloxy)-4-thiaheptanoyl glycyl glutamyl glutamate, which has improved solubility, was effective in experimental leukocytopenia in mice.
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KAZUO UMEZAWA, SHOJIRO MASUOKA, TAKUHITO OHSE, HIROSHI NAGANAWA, SHINI ...
1995 Volume 48 Issue 7 Pages
604-607
Published: July 25, 1995
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In the course of our screening for inhibitors of abl oncogene function, a culture nitrate of
Streptomyces aculeolatus. induced normal flat morphology in v-abl-expressing NIH3T3 cells. The active substance was isolated through ethyl acetate extraction, silica gel column chromatography, and reverse-phase HPLC. Mass and NMR spectroscopy including HMBC revealed that it had a novel naphthoquinone structure with a monoterpene, and we named it "naphthablin". Naphthablin inhibited Abl-induced morphological transformation in v-abl
ts-NIH3T3 cells at around 30μg/ml, and specifically inhibited RNA synthesis.
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I. Identity of the Producing Organism, Fermentation and Biological Activity
MARIANNA JACKSON, DAVID J. FROST, JAMES P. KARWOWSKI, PATRICK E. HUMPH ...
1995 Volume 48 Issue 7 Pages
608-613
Published: July 25, 1995
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The fusacandins, antifungal agents of the papulacandin class, are produced by a strain of
Fusarium sambucinum. Fermentation yielded 60mg/liter of fusacandin A and minor amounts of fusacandin B. As expected, the fusacandins inhibit (1, 3)-β-glucan synthesis. Fusacandin A is slightly less active than papulacandin B against
Candida albicans and, like papulacandin, loses activity in the presence of serum.
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II. Isolation and Structural Elucidation
JILL E. HOCHLOWSKI, DAVID N. WHITTERN, ALEX BUKO, LISA ALDER, JAMES B. ...
1995 Volume 48 Issue 7 Pages
614-618
Published: July 25, 1995
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Two novel antifungal compounds of the papulacandin class, named fusacandins A and B, have been isolated from
Fusarium sambucinum. Each compound contains two units of galactose and oneof glucose, the latter connected as a C-glycoside to an aromatic moiety. Fusacandin A is esterified at two sites with long-chain, unsaturated fatty acids and fusacandin B at only one site. The structures of the fusacandins were elucidated through analysis of mass spectral and 1-D and 2-D homonuclear and heteronuclear NMR data.
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Echinoserine, a New Member of the Quinoxaline Group, Produced by Streptomyces tendae
SABINE BLUM, HANS-PETER FIEDLER, INGRID GROTH, CHRISTOPH KEMPTER, HOLG ...
1995 Volume 48 Issue 7 Pages
619-625
Published: July 25, 1995
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A new member of the quinoxaline group antibiotics has been detected by HPLC-diode-array screening. The main compound produced by
Streptomyces tendae strain Tü 4031 showed a high degree of similarity in the UV-visible spectral region with echinomycin and their structural similarity was confirmed by structure elucidation using electron tandem mass spectrometry and 2D nuclear magnetic resonance. The new compound, named echinoserine, is a non-cyclic form of echinomycin, but it is not a biosynthetic precursor. Echinoserine is less antibiotically active than echinomycin.
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I. Taxonomy, Production, Isolation, and Preliminary Characterization
KOUICHI TSUCHIYA, SFFINICHI KOBAYASHI, TAKASHI HARADA, TAKASHI KUROKAW ...
1995 Volume 48 Issue 7 Pages
626-629
Published: July 25, 1995
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A novel acaricide, gualamycin, was isolated from the culture broth of
Streptomyces sp. NK11687. It was purified from the filtrate by column chromatographies. Gualamycin showed 100% acaricidal activity at 250 μg/ml against sensitive and resistant mites to Dicofol.
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II. Structural Elucidation
KOUICHI TSUCHIYA, SFFINICHI KOBAYASHI, TAKASHI KUROKAWA, TAIZO NAKAGAW ...
1995 Volume 48 Issue 7 Pages
630-634
Published: July 25, 1995
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A novel acaricide, gualamycin was isolated from the culture broth of
Streptomyces sp. NK11687. The structure of gualamycin was determined to be (2
R, 3
S, 4
S)-2-
O-[4-
O-(2-amino-2-deoxy-β-D-gulopyranosyl)-a-D-galactopyranosyl]-2, 3, 4-trihydroxy-4-[(2
S, 3
S, 4
S, 5
S)-3, 4-dihydroxy-5-hydroxymethylpyrrolidin-2-yl] butanoic acid by FAB-MS,
1H and
13C NMR, COSY, HMQC, HMBC, IR, X-ray crystallographic analyses and synthetic studies.
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DUSICA VUJAKLUA, JULIAN DAVIES
1995 Volume 48 Issue 7 Pages
635-637
Published: July 25, 1995
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We describe a simple and reliable method which allows the direct transfer of shuttle plasmids between
Streptomyces spp. and
E. coli. The method is based on the fact that plasmid DNA molecules can be released or taken up from cells under conditions of electroporation. When a suspension of a plasmid-containing
Streptomyces spp. is mixed with electroporation-competent
E. coli and submitted to an electric pulse, plasmid DNA transfer to the
E. coli recipient takes place. Two different
Streptomyces spp. (
S. lividans TK23, or TK24 and
S. rimosus 554w) were effective donors, and the method was successfully employed to transfer four different bifunctional vectors (pPMSOl, pFD666, pRL270X and pZG5) varying in size from 5.2-14.4kb, to
E. coli. This provides a convenient method for the analysis of Streptomycete transformants.
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KENJI UEDA, KYUNG-MIKIM KIM, TERUHIKO BEPPU, SUEHARU HORINOUCHI
1995 Volume 48 Issue 7 Pages
638-646
Published: July 25, 1995
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A 7.0-kb DNA fragment that conferred redbrown pigment production on
Streptomyces griseus was shotgun-cloned with a multicopy vector pIJ486 from this microorganism. By restriction endonuclease mapping and subcloning, a 1.5-kb fragment which is essential for the production of redbrown pigment was determined. The nucleotide sequence of this region revealed the presence of two open reading frames, ORF1 with 109 amino acids (named RppA) and ORF2 with 262 amino acids (RppB), in addition to a truncated ORF3. The termination codon of
rppA and the initiation codon of
rppB overlapped, sharing one common nucleotide, which strongly suggests that these two genes are cotranscribed. Both
rppA and
rppB were essentially required for the pigmentation. The RppB protein showed great similarity in amino acid sequence to a chalcone synthase, a key enzyme of central importance in the biosynthetic pathway of all classes of flavonoids in plants. Part of RppA showed sequence similarity to the 33kDa phosphoprotein of adenovirus. Nucleotide sequences homologous to
rppA and
rppB were widely distributed in
Streptomyces species, as determined by Southern hybridization. Further nucleotide sequencing of the entire
orf-
3 gene showed that ORF3 with 403 amino acids was a cytochrome P-450 (named P-450
RPP). These data suggested that the cloned fragment contained part of a gene cluster for the biosynthesis of a certain metabolite. Introduction of the subcloned 1.5-kb fragment into
Streptomyces lividans as well as
Escherichia coli also caused production of redbrown pigment, suggesting that RppA and RppB are capable of synthesizing the redbrown pigment from metabolites commonly present in bacteria.
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DAVID E. CANE, GUANGLIN LUO, CHAITAN KHOSLA, CAMILLA M. KAO, LEONARD K ...
1995 Volume 48 Issue 7 Pages
647-651
Published: July 25, 1995
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Feeding of (2
S, 3
R)-[2, 3-
13C
2]-2-methyl-3-hydroxypentanoyl NAC thioester (
1a) to the recombinant organism
Streptomyces coelicolor CH999/pCK7 harboring the complete set of
eryA genes from
Saccharopolyspora erythraea encoding the 6-deoxyerythronolide B synthase (DEBS) resulted in the formation of 6-deoxyerythronolide B (
2a) labeled with
13C at C-12 and C-13, as evidenced by the appearance of a pair of enhanced and coupled doublets in the
13C NMR spectrum. The level of
13C enrichment was 15-20 atom%
13C, as much as 100 times higher than the usually observed efficiency of incorporation of NAC thioesters into polyketide metabolites. Similar incorporation of (2
S, 3
R)-[3-
2H, 3-
13C]-2-methyl-3-hydroxypentanoyl NAC thioester (
1b) gave 6-deoxyerythronolide B (
2b) labeled with both
13C and deuterium at C-13. The intact incorporation of both precursors confirms the normal functioning of the recombinant DEBS proteins in the heterologous host.
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STEVEN J. GOULD, QIBO ZHANG
1995 Volume 48 Issue 7 Pages
652-656
Published: July 25, 1995
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Cytosinine-the nucleoside portion of blasticidin S-and pyridoxal phosphate were incubated with cell-free extracts of
Streptomyces griseochromogenes prepared in D
2O.
2H NMR analysis of recovered cytosinine showed it to contain deuterium enrichments at H-4' and H-2'. No exchange was observed with either boiled extract or from cytosinine and pyridoxal phosphate alone. These results reveal the presence of a tautomerase activity that contributes to the net transamination at C-4' in the conversion of cytosylglucuronic acid to blasticidin S, and its discovery supports the role of cytosinine as a biosynthetic intermediate.
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HLROYUKI NLSHIDA, TATSUO SAKAKIBARA, FUKUMATSU AOKI, TOSHIYUKI SAITO, ...
1995 Volume 48 Issue 7 Pages
657-666
Published: July 25, 1995
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A new rapamycin producing culture was isolated and designated as
Actinoplanes sp. N902-109. The addition of a cytochrome P-450 inhibitor and precursor feeding using this culture, and biotransformation approaches generated new rapamycin analogs with modifications at C-4, C-9, C-16, C-27, C-28 and/or C-39. The immunosuppressive activity of the resulting analogs was established in the mixed lymphocyte reaction assay.
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SYLVIE BOBILLOT, TAMAS BAKOS, PIERRE SARDA, TON THAT THANG, LI MING, A ...
1995 Volume 48 Issue 7 Pages
667-670
Published: July 25, 1995
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20-Homo tylosin, 20-nor tylosin, 20-deoxy-19, 20-didehydro tylosin (6-vinyl tylosin) and 2", 3"-didehydro-3"-deoxy tylosin were prepared by multi-step procedures. 20-Homo tylosin was about twice less active than tylosin while the other coumpounds exhibited very weak antibacterial activity.
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LAWRENCE C. CREEMER, HERBERT A. KIRST, THOMAS R. SHRYOCK, JACK B. CAMP ...
1995 Volume 48 Issue 7 Pages
671-675
Published: July 25, 1995
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A new fluorinated analog of tilmicosin was synthesized by the reductive amination of desmycosin with 3, 5-bis(trifluoromethyl)piperidine. Despite an apparently small change in structure, the fluorinated analog had much less
in vitro antimicrobial activity than tilmicosin and it failed to protect 3-day old chicks against a
Pasteurella multocida challenge at 64mg/kg sc. In a preliminary
in vivo fluorine NMR experiment in a female Sprague-Dawley rat, a
19F NMR signal was detected in the liver one hour after ip administration of the fluorinated compound. Therefore, although this fluorinated derivative had less antimicrobial activity than tilmicosin, it may nevertheless provide a suitable model of tilmicosin for pharmacokinetic studies using
in vivo fluorine NMR.
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JEAN-MARC PARIS, JEAN FRANCOIS, CHRISTIAN MOLHERAT, FRANCA ALBANO, MIR ...
1995 Volume 48 Issue 7 Pages
676-682
Published: July 25, 1995
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Pristinamycin IA was modified in a two-step procedure to give original derivatives possessing a tricyclic nucleus (
8a,
8b,
8c) or a substituted pyrrole ring (
10a,
10b) in place of the natural exocyclic 3-hydroxy-picolinoyl residue. This transformation involved firstly preparation of pyridinium betaines
5 from pristinamycin I
A and secondly a 1-3 dipolar cycloaddition between
5 and
N-substituted maleimides or diethyl ace tylenedicar boxy late. The compounds obtained were evaluated as antibacterial agents alone and in association with pristinamycin II
A.
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ISTVÁN F. PELYVÁS, MÁRIA MÁDI-PUSKÁ ...
1995 Volume 48 Issue 7 Pages
683-695
Published: July 25, 1995
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Novel pseudodisaccharide-type aminocyclitol antibiotic models, built up from D-arabinose, D-ribose, D-glucosamine, L-ristosamine and L-acosamine have been synthesized by the glycosylation of. suitably protected (azido)deoxyinosose aglycones derived by the Ferrier carbocyclic ring transformation of carbohydrate precursors. An alternative approach to related pseudodisaccharides, based on the Ferrier carbocyclization of reducing disaccharides, has also been elaborated. This latter method extends the scope of the Ferrier reaction, by demonstrating that acid-labile 2-deoxydisaccharides can also be readily transformed into the corresponding pseudodisaccharides under the slightly acidic conditions of this ring-transformation.
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NORIKO ARAI, KAZURO SHIOMI, HIROSHI TOMODA, NORIKO TABATA, DA JUN YANG ...
1995 Volume 48 Issue 7 Pages
696-702
Published: July 25, 1995
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New azaphilones named isochromophilones III-VI were isolated from the culture broth of
Penicillium multicolor FO-3216 as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT). Their structures were elucidated by NMR and other spectroscopic analyses. The IC
50 values of isochromophilones III, IV, V and VI for ACAT activity in an enzyme assay using rat liver microsomes were calculated to be 110, 50, 50 and 120μM, respectively.
View full abstract
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I. Screening, Taxonomy, Fermentation, Isolation and Biological Activity
KEIICHI MATSUZAKI, HODAKA IKEDA, ROKURO MASUMA, HARUO TANAKA, SATOSHI ...
1995 Volume 48 Issue 7 Pages
703-707
Published: July 25, 1995
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Isochromophilones I and II, the first novel gp120-CD4 binding inhibitors of microbial origin, were isolated from a cultured broth of a soil fungus designated as
Penidllium multicolor FO-2338. These compounds were obtained as yellow powders from the cultured broth together with the known related compounds sclerotiorin, ochrephilone and rubrorotiorin. Isochromophilones I and II (C
23H
25O
25Cl and C
22H
27O
4Cl, respectively) have an azaphilone skeleton and a chlorine atom. Isochromophilones strongly inhibited gp120-CD4 binding (IC
50: 6.6 and 3.9μM, respectively), but the other related compounds did not. Isochromophilone II inhibited significantly HIV replication in peripheral human lymphocytes at 25 μM.
View full abstract
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II. Structure Elucidation
KEIICHI MATSUZAKI, HARUO TANAKA, SATOSHI OMURA
1995 Volume 48 Issue 7 Pages
708-713
Published: July 25, 1995
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The structures of isochromophilones I and II, new gp!20-CD4 binding inhibitors isolated from a cultured broth of
Penicillium multicolor FO-2338, were elucidated by NMR experiments. Both of compounds have an azaphilone skeleton substituted by a chlorine atom at C-5 and a side chain, 3, 5-dimethyl-l, 3-heptadien at C-3. Additionally, isochromophilone I has a γ-lactone ring, and isochromophilone II has 2-oxopropyl moiety instead of a γ-lactone ring.
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KAZURO SHIOMI, NORIKO ARAI, MAYUMI SHINOSE, YOKO TAKAHASHI, HLROSHI YO ...
1995 Volume 48 Issue 7 Pages
714-719
Published: July 25, 1995
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New antibiotics, phthoxazolins B, C and D were isolated from the fermentation broth of
Streptomyces sp. KO-7888. They are geometrical isomers of 10-hydroxyphthoxazolin A. They showed selective antifungal activity against
Phytophthora parasitica in vitro and modest herbicidal activity in a laboratory test, but the potencies were different among isomers.
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YOSHITAKE TANAKA, MASAKO SUGOH, WEI JI, JUN IWABUCHI, HIROSHI YOSHIDA, ...
1995 Volume 48 Issue 7 Pages
720-724
Published: July 25, 1995
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A new screening method for inhibitors of cellulose biosynthesis is described. This method utilized three microbial strains; a cellulose-containing fungus
Phytophthora, and a cellulose non-containing fungus
Candida, and a bacterial strain of
Acetobacter, a cellulose-producing acetic acid bacterium. The primary screen examined microbial cultures for selective growth inhibition against
Phytophthora with no inhibition against
Candida. The secondary screen tested for herbicidal activity. Thirdly, the active cultures were examined for their inhibition of cellulose biosynthesis by an
Acetobacter strain. A screening trial with this new method led to the discovery of two microbial metabolites named phthoxazolin A and phthoramycin as new inhibitors of cellulose biosynthesis with herbicidal activity.
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TIMM ANKE, ANDREAS WERLE, SYLVIA ZAPF, ROBERT VELTEN, WOLFGANG STEGLIC ...
1995 Volume 48 Issue 7 Pages
725-726
Published: July 25, 1995
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KAZUTOSHI SAKAMOTO, SHIZUE IZUMI, MICHIYO MIYAUCHI, MASAKUNI OKUHARA
1995 Volume 48 Issue 7 Pages
727-729
Published: February 27, 1995
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PAUL A. LARTEY, RAMIN FAGHIH, THOMAS PAGANO, HUGH N. NELLANS, ALBERT P ...
1995 Volume 48 Issue 7 Pages
730-732
Published: July 25, 1995
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HIDEAKI KAKEYA, ISAMU TAKAHASHI, GEN OKADA, KIYOSHI ISONO, HIROYUKI OS ...
1995 Volume 48 Issue 7 Pages
733-735
Published: July 25, 1995
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DIDIER VAN DER PYL, PIERRE CANS, JEAN JACQUES DEBERNARD, FREDERIC HERM ...
1995 Volume 48 Issue 7 Pages
736-737
Published: July 25, 1995
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TAKUYA GOMIBUCHI, MASAHIRO HIRAMA
1995 Volume 48 Issue 7 Pages
738-740
Published: July 25, 1995
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KUNIAKI TATSUTA, MASAYUKI KITAGAWA, TAKAO HORIUCHI, KOUICHI TSUCHIYA, ...
1995 Volume 48 Issue 7 Pages
741-744
Published: July 25, 1995
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SATOSHI OMURA, FUMIYOSHI KUNO, KAZUHIKO OTOGURO, TOSHIAKI SUNAZUKA, KA ...
1995 Volume 48 Issue 7 Pages
745-746
Published: July 25, 1995
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TOHRU NAGAMITSU, TOSHIAKI SUNAZUKA, HEIKE STUMP, RIKA OBATA, SHIHO ARI ...
1995 Volume 48 Issue 7 Pages
747-748
Published: July 25, 1995
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RIKA OBATA, TOSHIAKI SUNAZUKA, LI ZHUORONG, HIROSHI TOMODA, SATOSHI OM ...
1995 Volume 48 Issue 7 Pages
749-750
Published: July 25, 1995
Released on J-STAGE: April 19, 2006
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