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Volume 37, Issue 10
Displaying 1-50 of 74 articles from this issue
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Daisuke YAMAMOTO, Keita MATSUMOTO, Toshimasa ISHIDA, Masatoshi INOUE, ...1989 Volume 37 Issue 10 Pages 2577-2581
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to elucidate the conformational characteristics of cysteine protease inhibitors contributing to their inhibitory activities, the conformation of E-64 (N-[N-(L-3-trans-carboxyoxiran-2-carbonyl)-L-leucyl]-agmatine), a potent inhibitor of papain, was determined by X-ray crystal structure analysis. The molecules were packed in the crystal through electrostatic forces and hydrogen bonding between the oppositely charged terminal groups and between the amide groups. Two crystallographically independent E-64 molecules both took a flattened and slightly curved structure, which is similar to that of loxistatin, a related cysteine protease inhibitor. Based on the present results, a possible inhibitory mechanism of E-64 is proposed, with reference to the binding mode observed in the crystal structure of papain-substrate analogue complex.View full abstractDownload PDF (732K) -
Shoko YOKOYAMA, Tomoko FUJIWARA, Hiromi TSUCHIYA, Akiko KANEKO, Fumio ...1989 Volume 37 Issue 10 Pages 2582-2586
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe rates of release of thiamine disulfide (TDS) from higher fatty acid-TDS complexes were determined in a JP XI dissolution test apparatus in JP XI disintegration test medium No. 1 (pH 1.2) at various temperatures, and the thermodynamic quantities for the release of TDS from the complexes were estimated. The concentration of TDS was determined spectrophotometrically.The rate of release of TDS from the complexes decreased with increasing carbon number in the fatty acid and increased at higher temperature. The values of free energy change ΔG, entropy change ΔS, and enthalpy change ΔH for the release of TDS from the complexes were all positive. The release of TDS from the complex was found to be an enthalpically controlled reaction.The release of TDS from octadecanoic acid-TDS complex, (SA)6(TDS), was found to be most disadvantageous from the enthalpic viewpoint and most advantageous from the entropic viewpoint as compared with the complexes formed with hexadecanoic acid and tetradecanoic acid. Furthermore, the largest value of activation energy for the release of TDS from (SA)6(TDS) was found to correspond to the largest positive value of free energy change for the release of TDS.View full abstractDownload PDF (636K) -
Kazuhiro OHTANI, Shunso HATONO, Kenji MIZUTANI, Ryoji KASAI, Osamu TAN ...1989 Volume 37 Issue 10 Pages 2587-2591
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom rhizomes of Panax japonicus (Araliaceae), two polysaccharides named tochibanan-A and -B, which show reticuloendothelial-potentiating activity in the carbon clearance test in mice, were isolated. The structure of tochibanan-A (molecular mass : 23000) was elucidated as a linear β-1, 4-D-galactan. Tochibanan-B (molecular mass : 40000) consists of D-galactose (87.1%), L-arabinose, D-glucose and D-galacturonic acid and has a β-D-(1→4)-linked galactopyranosyl backbone possessing GalA-(1→6)-Gal, Ara-(1→5)-Ara, Gal, and Glc side chains. The structure around the branching points and the repeating unit were investigated and a possible structure of tochibanan-B is proposed.View full abstractDownload PDF (743K) -
Nobuo KAWAHARA, Shoichi NAKAJIMA, Mikio YAMAZAKI, Ken-ichi KAWAI1989 Volume 37 Issue 10 Pages 2592-2595
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new epidithiodioxopiperazine derivative, emethallicin A (1), was isolated along with ergosterol from the mycelial extract of the heterothallic fungus, Emericella heterothallica (mating type A). The structure of emethallicin A (1) was established on the basis of chemical and spectroscopic investigations and finally by chemical transformation to apoaranotin (11). Emethallicin A (1) has the same basic skeleton as apoaranotin (11), with C6-C2 carboxylic acid (mandelic and phenylacetic acids) diester moieties, and showed a potent inhibitory activity on histamine release from mast cells.View full abstractDownload PDF (625K) -
Tohru HINO, Ziping LAI, Hiroko SEKI, Ritsuko HARA, Tadao KURAMOCHI, Ma ...1989 Volume 37 Issue 10 Pages 2596-2600
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree marine β-carboline alkaloids, eudistomin H, I, and P (5, 4, and 6), were synthesized. The Bischler-Napieralski reaction of N-(N-benzyloxycarbonylprolyl)tryptamine (11) gave the 3, 4-dihydro-β-carboline (12), which was converted to eudistomin I (5) via 13 on deprotection and dehydrogenation. Compound 13 was obtained directly from N-(N-tert-butoxycarbonylprolyl)tryptamine (17) by means of the Bischler-Napieralski reaction with polyphosphoric ester-dichloroethane. The bromination of 5 with N-bromosuccinimide (NBS)-acetic acid gave eudistomin H (4). Bromination of the 5-methoxypyrrolo[2, 3-b]indole (21) obtained from the 5-hydroxytryptamine (18) gave the 6-bromo derivative (22) which afforded 6-bromo-5-methoxytryptamine (25) on alkaline hydrolysis. The Bischler-Napieralski reaction of the 6-bromo-5-methoxy-N-prolyltryptamine (27) gave the 1-pyrrolinyl-3, 4-dihydro-β-carboline (29). Dehydrogenation of 29 with NBS followed by demethylation with boron tribromide provided eudistomin P (6) via 30.View full abstractDownload PDF (899K) -
Tozo FUJII, Tohru SAITO, Tsuyoshi NAKASAKA1989 Volume 37 Issue 10 Pages 2601-2609
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first syntheses of 3-methyladenosine (3a) and 3-methyl-2'-deoxyadenosine (3b), both in the form of the p-toluenesulfonate salt, have been achieved through two parallel 6-step routes starting from adenosine (5a) and 2'-deoxyadenosine (5b), which are based on the "fission and reclosure" technology for modification of the adenine ring. These 3-methyladenine nucleosides (3a, b·TsOH) were very unstable under not only acidic but also alkaline conditions. At pH 1 and 25°C, 3a·TsOH (half-life 17 min) underwent glycosidic hydrolysis (depurinylation) some thousand times faster than did adenosine (5a) itself. At pH 3.34 and 25°C, the 2-deoxyribosyl analogue 3b·TsOH (half-life 2.7 min) was depurinylated 370 times more rapidly than the ribosyl analogue 3a·TsOH (half-life 1010 min). The glycosidic bond of the imidazole 2-deoxyriboside 11b, an intermediate for the present synthesis of 3b·TsOH, was also hydrolyzed easily at pH 1 and room temperature. In H2O at pH 8.32 and 25°C, 3a·TsOH readily underwent ring opening in the pyrimidine moiety and came to equilibrium with the (N-methylformamido)imidazole derivative 10a, which was further deformylated under more alkaline conditions. The ring opening was ca. 30 times as fast as that of 1-methyladenosine (17). In H2O at pH 8.98 and 25°C, the 2-deoxyribosyl analogue 3b·TsOH underwent not only similar ring opening but also glycosidic hydrolysis competitively. The possible factors responsible for the high reactivity of 3a·TsOH are discussed on the basis of its X-ray crystal structure.View full abstractDownload PDF (1342K) -
Hiroshi KASHIHARA, Hiroshi SUEMUNE, Katsuhiko FUJIMOTO, Kiyoshi SAKAI1989 Volume 37 Issue 10 Pages 2610-2614
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new synthetic route to optically active α, β-, β', γ'-unsaturated alcohols was established. The chiral enones (6 and 8), prepared from dimethyl malate via chiral phosphonates (4 and 5), were diastereoselectively reduced with Zn(BH4)2 to afford the 1, 3-syn derivatives (9 and 11). As an application of this 1, 3-asymmetric induction, the fungitoxic C-18 hydroxy unsaturated fatty acid isolated from stromata of Epichloe typhina was synthesized.View full abstractDownload PDF (750K) -
Masayuki SATO, Kazuhisa TAKAYAMA, Chikara KANEKO1989 Volume 37 Issue 10 Pages 2615-2620
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthesis of 2-spirocyclic 1, 3-dioxin-4-ones and their Diels-Alder reaction with cyclopentadiene are described. The study provides not only a new route to chiral carbocyclic C-nucleoside precursors, but also a new methodology for asymmetric Diels-Alder reactions.View full abstractDownload PDF (857K) -
New Glucosides of a 4-Hydroxy-5-methylcoumarin and a Dihydro-α-pyrone from Gerbera jamesonii hybridaSeiji NAGUMO, Tatsunori TOYONAGA, Takao INOUE, Masahiro NAGAI1989 Volume 37 Issue 10 Pages 2621-2623
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new glucosides, 2, C16H18O9, mp 202-203°C, [α]20D-96.4°(MeOH) and gerberin (5), C12H18O8, [α]19D +11.2°(MeOH), were isolated from the aerial part of Gerbera jamesonii hybrida (Compositae). On methanolysis, 2 yielded 6-hydroxy-4-methoxy-5-methylcoumarin. The tetraacetate of 5 yielded tetraacetylparasorboside on catalytic hydrogenation. The chemical structures of 2 and 5 were established as 4-β-D-glucopyranosyloxy-6-hydroxy-5-methylcoumarin and (6S)-5, 6-dihydro-4-β-D-glucopyranosyloxy-6-methyl-2H-pyran-2-one, respectively. The yield of gerberin (5) was quite high, amounting to about 3.7% based on the weight of the dried plant material.View full abstractDownload PDF (553K) -
Reiko SAIJO, Gen-ichiro NONAKA, Itsuo NISHIOKA1989 Volume 37 Issue 10 Pages 2624-2630
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chemical examination of the leaves of Mallotus repandus (WILLD.) MUELLER-ARG. (Euphorbiaceae) has led to the isolation of four new hydrolyzable tannins, named repandusinin (10), repandusinic acids A (11a) and B (14a) (as monopotassium salts) and mallotinin (15), together with glucogallin (1), eugeniin (2), corilagin (3), punicafolin (4), geraniin (5), furosin (6), mallotinic acid (7), mallotusinic acid (8) and brevifolin carboxylic acid (9). Based on the chemical and spectroscopic evidence, repandusinin was assigned the structure (10) in which brevifolin carboxylic acid is attached to the C-4 position of the glucose moiety in mallotinic acid, while repandusinic acids A and B were characterized as 1-O-galloyl-3, 6-(R)-hexahydroxydiphenoyl-(11a) and 1-O-galloyl-3, 6-(R)-valoneayl-4-O-(4'-dehydrochebuloyl)-β-D-glucoses (14a), respectively. Similarly, mallotinin was found to have the structure (15) possessing a new acid, mallotic acid, linked to the C-2 position of the corilagin moiety.View full abstractDownload PDF (901K) -
Kouki KITAGAWA, Tatsuhiko KAWAMOTO, Shiroh FUTAKI, Shinya KIYAMA, Tada ...1989 Volume 37 Issue 10 Pages 2631-2638
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo enkephalin-containing peptides, peptide E and dynorphin (1-24), were synthesized by conventional solution methods employing a new Trp derivative, Nin-(2, 4, 6-triisopropylphenylsulfonyl)tryptophan [Trp(Tps)]. All protecting groups employed including the Tps group were removed by treatment with 1 M trifluoromethanesulfonic acid (TFMSA)-thioanisole in trifluoroacetic acid (TFA) at the final steps of these syntheses. Subsequent purifications by Sephadex G-25 chromatography, CM-Biogel A ion exchange chromatography, and reversed-phase high-performance liquid chromatography afforded highly purified samples. Both synthetic peptide E and dynorphin (1-24) exhibited high in vitro opioid activity. The usefulness of this new tryptophan derivative for practical peptide synthesis was established through these syntheses of complex Trp-containing peptides.View full abstractDownload PDF (1319K) -
Fumiko ABE, Tatsuo YAMAUCHI, Alfred S. C. WAN1989 Volume 37 Issue 10 Pages 2639-2642
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree normonoterpenoids, cerberidol, epoxycerberidol, and cyclocerberidol, and their β-D-allopyranosides were obtained from the air-dried leaves of Cerbera manghas and C. odollam.View full abstractDownload PDF (574K) -
Chuzo IWATA, Yoshiji TAKEMOTO, Ayatsugu NAKAMURA, Takeshi IMANISHI1989 Volume 37 Issue 10 Pages 2643-2646
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidation of the silyl enol ether of (2RS, 5RS, 10RS)-6, 10-dimethyl-2-pivaloyloxyspiro[4.5]dec-6-en-8-one (5) with triphenyl phosphite ozonide (TPPO) gave stereoselectively the C9-hydroxylated derivative (6a), which was transformed into a spirovetivane phytoalexin, (±)-3-hydroxysolavetivone (1), by a several-step sequence.View full abstractDownload PDF (720K) -
Shinya HARUSAWA, Norio SHIBATA, Naoki YAMAZAKI, Satomi SAKANOUE, Toshi ...1989 Volume 37 Issue 10 Pages 2647-2650
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of azabicyclothionocarbonate (6a) with a catalytic amount of α, α'-azobisisobutyronitrile in refluxing benzene leads to the formation of a new azaspirolactone (8), whose structure ws unambiguously established by an X-ray analysis. A mechanism is proposed for the formation of 8.View full abstractDownload PDF (628K) -
Kimio FURUHATA, Kanki KOMIYAMA, Kazuyoshi TAKEDA, Hiroaki TAKAYANAGI, ...1989 Volume 37 Issue 10 Pages 2651-2654
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 7-O-hydroxy-9a-methoxymitosane sodium salt with glycosyl halide derivatives gave the corresponding 7-O-glycosyl-9a-methoxymitosanes in reasonable yields. A major product, 7-O-(2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranosyl)-9a-methoxymitosane, was isolated from the reaction mixture of 7-O-hydroxy-9a-methoxymitosane sodium salt with 2, 3, 4, 6-tetra-O-acetyl-D-glucopyranosyl bromide, in addition to two minor by-products, bissaccharide derivatives of mitomycin. The structures of glycosyl derivatives of mitomycin were elucidated by analysis of the nuclear magnetic resonance spectra. Field desorption mass spectrometry was also successfully used for the confirmation of these structures. The cytocidal, antibacterial, and antitumor activities of 7-O-glycosyl-9a-methoxymitosanes were also examined.View full abstractDownload PDF (674K) -
Takashi YOSHIDA, Kazufumi YAZAKI, Muhammad Usman MEMON, Izumi MARUYAMA ...1989 Volume 37 Issue 10 Pages 2655-2660
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fruit extract of Alnus sieboldiana, a new hydrolyzable tannin, alnusiin (1), was isolated together with five known tannins : tellimagrandin I (6), pedunculagin (7), casuarinin (9), casuariin (10) and 2, 3-O-(S)-hexahydroxydiphenoyl-D-glucose (11). The structure (1) of alnusiin in which a monolactonized tergalloyl group, a rare component unit, bonds to the glucose residue, was elucidated based on spectral analyses including 1H-13C long-range shift correlation spectroscopy, and chemical methods. Another new hydrolyzable tannin with a related structure, bicornin (21), and six known galloylglucoses as well as six ellagitannins (including oligomers), were isolated from Trapa bicornis fruits and their structures were characterized.View full abstractDownload PDF (860K) -
Kenichi AKAJI, Nobutaka FUJII, Fuminori TOKUNAGA, Toshiyuki MIYATA, Sa ...1989 Volume 37 Issue 10 Pages 2661-2664
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTachyplesin I, a 17-residue peptide amide with two disulfide bridges isolated from an acid extract of horseshoe crab hemocyte debris, was synthesized by the 9-fluorenylmethyloxycarbonyl (Fmoc)-based solid-phase method followed by two steps of deprotection and subsequent air-oxidation. The thioanisole-mediated deprotection with 1 M trifluoromethanesulfonic acid was first employed to cleave the peptide amide from the resin and, at the same time, to deprotect the side chain protecting groups employed, except for the S-Acm (acetamidomethyl) group. The 4 Acm groups attached were next cleaved by silver trifluoromethanesulfonate. In addition, two related peptides, tachyplesin II and polyphemusin I, were similarly synthesized. Synthetic tachyplesin I inhibited the lipopolysaccharide-mediated activation of clotting factor C to the same extent as did the corresponding natural peptide. The relative potencies of synthetic tachyplesin II and synthetic polyphemusin I with respect to natural tachyplesin I (taken as 1) were 2.1 and 0.61, respectively.View full abstractDownload PDF (713K) -
Tsutomu HATANO, Taeko YASUHARA, Takuo OKUDA1989 Volume 37 Issue 10 Pages 2665-2669
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCornusiin D (3), cornusiin E (4) and cornusiin F (5), new dimeric and trimeric hydrolyzable tannins, were isolated from the fruits of Cornus officinalis (Cornaceae), and their structures were established based on the chemical and spectroscopic data. Unusual chemical shifts of valoneoyl protons and anomeric protons of glucose cores in the proton nuclear magnetic resonance spectra of 3 and 4 were correlated with the stereostructures around the valoneoyl groups. Camptothin A (6) and camptothin B (7), dimeric hydrolyzable tannins previously isolated from Camptotheca acuminata, were also isolated from the fruits of Cornus officinalis.View full abstractDownload PDF (776K) -
Masakazu MURATA, Yoshiyasu TERAO, Kazuo ACHIWA, Toshiyuki NISHIO, Kazu ...1989 Volume 37 Issue 10 Pages 2670-2672
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEfficient asymmetric syntheses of glycerol derivatives were achieved by lipase-catalyzed transesterification. 2-O-Substituted glycerol was enzymatically esterified with acetic acid or acetate in an organic medium to afford an optically active monoester. In particular, lipase-catalyzed transesterification with vinyl acetate or phenyl acetate gave high chemical and optical yields.View full abstractDownload PDF (482K) -
Yoshisuke TSUDA, Yukihiro OKUNO, Minoru IWAKI, Kimihiro KANEMITSU1989 Volume 37 Issue 10 Pages 2673-2678
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOne of the hydroxyl groups in glycosides was regio- and stereo-selectively converted to an amino group as follows. A glycoside was regioselectively converted to an oxo-glycoside by bis-tributyltin oxide-bromine oxidation. Oximation of this and reduction of the resulting oxime in a stereoselective manner gave an amino-glycoside in a satisfactory yield.By application of this method, 4-amino-4-deoxy-D-galactose, 4-amino-4-deoxy-L-arabinose, 3-amino-3-deoxy-D-allose, 3-amino-3-deoxy-D-glucose, 3-amino-3-deoxy-D-ribose, 3-amino-3-deoxy-D-xylose, and 2-amino-2-deoxy-D-mannose were synthesized in satisfactory yields from D-xylose or D-glucose as their α- or β-methyl glycosides. The method also provided a practical synthetic route to nojirimycin (5-amino-5-deoxy-D-glucose), a glucosidase-inhibitory antibiotic, from D-glucose.View full abstractDownload PDF (971K) -
Henriette LANDELLE, Daniel LADUREE, Michel CUGNON DE SEVRICOURT, Max R ...1989 Volume 37 Issue 10 Pages 2679-2682
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclization reaction of hydrazine with carbazole-2, 3-methyl dicarboxylates gave 1, 4-dioxo-1, 2, 3, 4-tetrahydropyridazino[4, 5-b]carbazoles. Chlorodehydroxylation provided 1, 4-dichloropyridazino[4, 5-b]carbazoles and nucleophilic substitution gave 1, 4-dialkoxy pyridazino[4, 5-b]carbazoles. These compounds were tested for cytotoxic activity against L1210 leukemia in mice.View full abstractDownload PDF (613K) -
Zhao-Quan WANG, Manabu NODE, Feng-Ming XU, Hui-Ping HU, Kaoru FUJI1989 Volume 37 Issue 10 Pages 2683-2686
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new kaurene-type diterpenoids, rabdoinflexins A (1) and B (2), were isolated from the leaves of Rabdosia inflexa. Their structures including absolute configuration were elucidated on the basis of spectral data and chemical evidence. A chemical conversion into rabdoserrin A (5) from rabdoinflexin A (1) established the absolute configuration of rabdoserrin A.View full abstractDownload PDF (611K) -
Kazuo TSUZUKI, Toshiaki SUNAZUKA, Shogo MARUI, Hajime TOYODA, Satoshi ...1989 Volume 37 Issue 10 Pages 2687-2700
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical modifications of 8, 9-anhydroerythromycin A 6, 9-hemiacetal (1), which showed gastrointestinal motor stimulating (GMS) activity 10 times more potent than that of erythromycin A (EM-A), were undertaken to search for derivatives having stronger GMS activity and no antimicrobial activity; details are described in this and a subsequent paper. Displacement of a methyl group of the dimethylamino group of 1 with an ethyl group and an isopropyl group provided de(N-methyl)-N-ethyl-8, 9-anhydroerythromycin A 6, 9-hemiacetal (55) and de(N-methyl)-N-isopropyl-8, 9-anhydroerythromycin A 6, 9-hemiacetal (58), respectively. They showed significant GMS activity and no antibacterial activity. In particular, the GMS activity of 58 was increased to 248 times that of EM-A. EM-A and the derivatives obtained in this study mimic exogenous motilin in the dog. The name "motilide", meaning a motilin-like macrolide, is proposed for this new family of macrolide compounds.View full abstractDownload PDF (1872K) -
Toshiaki SUNAZUKA, Kazuo TSUZUKI, Shogo MARUI, Hajime TOYODA, Satoshi ...1989 Volume 37 Issue 10 Pages 2701-2709
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of quaternary ammonium derivatives of 8, 9-anhydroerythromycin A 6, 9-hemiacetal (1) and 9, 9-dihydroerythromycin A 6, 9-epoxide (2) has been prepared and tested for antimicrobial activity and gastrointestinal motor stimulating (GMS) activity in the dog (in vivo). The GMS activity is enhanced markedly when small alkyl halides and unsaturated alkyl halides such as allyl bromide and propargyl bromide are added to the dimethylamino group of 1. Among them, N-propargyl-8, 9-anhydroerythromycin A 6, 9-hemiacetal bromide (3) exhibits GMS activity 2890 times stronger than that of erythromycin A and is completely devoid of antimicrobial activity. The potency of 3 is comparable to that of synthetic motilin both in vitro and in vivo.View full abstractDownload PDF (1163K) -
Miguel Fernandez BRANA, Ascension FERNANDEZ, Mercedes GARRIDO, Maria L ...1989 Volume 37 Issue 10 Pages 2710-2712
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of N-substituted 3, 4-diphenyl-1H-pyrrole-2, 5-diones (diphenylmaleimides)(IV) were synthesized and tested for cytostatic activity. Compounds IVa-k were prepared from diphenylmaleic anhydride or its dinitro derivative (V or VI) and the corresponding amine. Compounds IVI-n were obtained by reaction of 3-(p-nitrophenyl)-4-phenyl-1H-pyrrole-2, 5-dione potassium salt with the appropriate chloroalkylamine. Hydrogenation of IVI, n gave the the corresponding cis-3-(p-aminophenyl)-4-phenylsuccinimides (VIIIa, b). The structure-cytostatic activity relationship of these compounds is discussed.View full abstractDownload PDF (556K) -
Shiro YOSHIZAKI, Eiyu YO, Masanao UMEZATO, Naoto NAKAGIRI, Youichi YAB ...1989 Volume 37 Issue 10 Pages 2713-2716
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of procaterol derivatives having a tert-amino group was synthesized. Among them, a morpholino derivative (4a, R1=H, NR2R3=morpholino) showed β-selective and rather potent adrenoceptor stimulant activities in an in vivo assay using anesthetized dogs. On the other hand, a morpholinopropanol analogue (4j, R1=CH3, NR2R3=morpholino) showed 400 times less potent bronchodilator activity than that of 4a. Some of the compounds showed weak bronchodilator activities and weak effects on the heart. It seems that steric hindrance around the nitrogen atom of catecholamines has a significant influence on β-adrenoceptor stimulant activities. Compound 4a also showed anti-allergic action estimated in terms of the inhibition of homologous passive cutaneous anaphlaxis in rats.View full abstractDownload PDF (609K) -
Mitsuo SUGIYAMA, Toshiaki SAKAMOTO, Keiichi TABATA, Hiroshi FUKUMI1989 Volume 37 Issue 10 Pages 2717-2722
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 3-Dihydro-5H-oxazolo[3, 2-a]thieno[3, 2-d]-(2a-d), [3, 4-d]-(2e-h), and [2, 3-d]pyrimidine derivatives (2i, j) were synthesized and evaluated for gastric antisecretory activity. These analogues (2) were prepared stepwise starting from formylthiophenecarbamates (4). The structure-activity relationships of these compounds are discussed.View full abstractDownload PDF (777K) -
Ryuichi IEMURA, Manabu HORI, Tadayuki SAITO, Hiroshi OHTAKA1989 Volume 37 Issue 10 Pages 2723-2726
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of obtaining new H1-antihistaminic agents, transformations of previously reported antihistaminic benzimidazoles were performed on the basis of the concept of bioisosterism. Among the compounds prepared, imidazo[4, 5-b]pyridine (8) and 4(3H)-quinazolinone (11) exhibited significant H1-antihistaminic activity.View full abstractDownload PDF (645K) -
Junichi KITAJIMA, Yasuko TANAKA1989 Volume 37 Issue 10 Pages 2727-2730
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new triterpenoid glycosides were isolated from the leaf blades and the petioles of Schefflera octophylla (Araliaceae). Their structures were characterized as 3α-hydroxylup-20(29)-ene-23, 28-dioic acid 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside and 3-epi-betulinic acid 3-O-β-D-glucopyranoside on the basis of spectral and chemical investigations.View full abstractDownload PDF (705K) -
Takao KONOSHIMA, Mutsuo KOZUKA, Mitsumasa HARUNA, Kazuo ITO, Takeatsu ...1989 Volume 37 Issue 10 Pages 2731-2735
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new triterpenoid saponins (wistariasaponins A, B1, B2 and C) were isolated as methyl ester forms from the knots of Wistaria brachybotrys (Leguminosae), and their structures were characterized as 3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]wistariasapogenol A, 3-O[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl(1→2)-β-D-glucuronopyranosyl]wistariasapogenol B, 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-galactopyranosyl(1→2)-β-D-glucuronopyranosyl]wistariasapogenol B and 3-O-[α-L-rhamnopyranosyl(1→2)-β-D-xylopyranosyl-(1→2)-β-D-glucuronopyranosyl]soyasapogenol B, respectively, on the basis of chemical and physicochemical evidence. The inhibitory effects of these saponins and sapogenols on Epstein-Barr virus activation induced by a tumor promoter were also tested for the primary screening of anti-tumor promoting activities.View full abstractDownload PDF (735K) -
Mitsuhiko NOSE, Sakae AMAGAYA, Yukio OGIHARA1989 Volume 37 Issue 10 Pages 2736-2740
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe corticosterone secretion-inducing activities of saikosaponin a, saikosaponin c and saikosaponin d, isolated from the root of Bupleurum falcatum L., and 27 metabolites formed in the murine alimentary tract were studied in mice. Serum corticosterone was determined by high-performance liquid chromatography (HPLC). Intraperitoneal administration of saikosaponin a and its intestinal metabolite, prosaikogenin F, showed corticosterone secretion-inducing activity at a dose of 0.1 mmol/kg, and maximally increased it at a does of 0.4 mmol/kg. On the other hand, the genuine sapogenin, saikogenin F, was inactive. Saikosaponin b1 and saikosaponin g, gastric metabolites of saikosaponin a, and their intestinal metabolites, prosaikogenin A, prosaikogenin H, saikogenin A and saikogenin H, were also inactive. Serum corticosterone was increased by the administration of saikosaponin d and its intestinal metabolite, prosaikogenin G, at a dose of 0.04 mmol/kg, and it reached the maximal level at the dose of 0.1 mmol/kg. Saikogenin G also showed a slight activity. A gastric metabolite of saikosaponin d, saikosaponin b2, and its intestinal metabolites, prosaikogenin D and saikogenin D, were inactive. In the experiments on saikosaponin c and its metabolites, saikosaponin c was inactive but its intestinal metabolites, especially prosaikogenin E-2, showed activity almost equal to that of saikosaponin a. Saikosaponin h and saikosaponin i, gastric metabolites of saikosaponin c, were also inactive, but their prosaikogenins showed slight activities. When these compounds were orally administered, their corticosterone secretion-inducing activities were similar to those obtained in the intraperitoneal experiment.These results suggest that a proper polar balance between the sugar moiety and the aglycone is important for the corticosterone secretion-inducing activity of saikosaponins and their metabolites.View full abstractDownload PDF (659K) -
Hiromichi MATSUURA, Tsuyoshi USHIROGUCHI, Yoichi ITAKURA, Toru FUWA1989 Volume 37 Issue 10 Pages 2741-2743
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new furostanol glycoside (2), named sativoside-B1, was isolated from garlic, bulbs of Allium sativum L., along with proto-desgalactotigonin (3). The structure of 2 was established to be (25R)-26-O-β-D-glucopyranosyl-22-hydroxy-5α-furostane-3β, 6β, 26-triol 3-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside.From roots of this plant, two new steroidal glycosides, named sativoside-R1 (16) and sativoside-R2 (15) were isolated and their structures were determined to be (25R)-26-O-β-D-glucopyranosyl-22-hydroxy-5α-furostane-3β, 26-diol 3-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (16) and its corresponding spirostanol glycoside (15). Besides these glycosides, three known glycosides, 3, desgalactotigonin (13) and F-gitonin (14) were isolated and identified.In a glycoside fraction of the leaves of A. sativum, steroidal glycosides were not detected by thin layer chromatography analysis.View full abstractDownload PDF (609K) -
Atsushi HIRAOKA, Satoru KOIKE, Setsuko SAKAGUCHI, Yoko MASUDA, Fumiko ...1989 Volume 37 Issue 10 Pages 2744-2746
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour (in total) compounds with inhibitory effects on the activity of bovine serum monoamine oxidase were isolated from the methanol-water extracts of Rhei Rhizoma (Daiou) and Sennae Folium (Senna), and identified as sennosides A, B, E and F. Among them, sennosides A and B were obtained from both Rhei Rhizoma and Sennae Folium, while sennosides E and F were detected only in the former. The 50% inhibitory concentrations of the four sennosides were 17, 9, 24 and 13 μM, respectively, and the type of inihibition by sennosides A and B with respect to allylamine as the substrate was non-competitive.View full abstractDownload PDF (569K) -
Yoshihisa ASADA, Masako IKENO, Takehito UEOKA, Tsutomu FURUYA1989 Volume 37 Issue 10 Pages 2747-2752
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree novel triterpene saponins named desacylmasonosides 1 (1), 2 (2), and 3 (3) have been isolated from the weak alkaline hydrolyzate of the crude saponin obtained from the corms of Crocosmia masonorum. On the basis of spectral and chemical evidence, their structures were characterized as 3-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]-28-O-{2-O-[β-D-apio-D-furanosyl-(1→4)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl]-3-O-(β-D-glucopyranosyl)-β-D-fucopyranosyl}polygalacic acid (1), 3-O-β-D-glucopyranosyl-28-O-{2-O-[β-D-apio-D-furanosyl-(1→4)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl]-3-O-(β-D-glucopyranosyl)-β-D-fucopyranosyl}polygalacic acid (2) and 3-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranosyl]-28-O-{2-O-[β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl]-3-O-(β-D-glucopyranosyl)-β-D-fucopyranosyl}polygalacic acid (3).View full abstractDownload PDF (970K) -
Kenzo YAMANAKA, Hiroshi OHBA, Akira HASEGAWA, Ryoji SAWAMURA, Shoji OK ...1989 Volume 37 Issue 10 Pages 2753-2756
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe genotoxic effects of dimethylarsinic acid (DMAA), one of the main metabolites of inorganic arsenics in mammals, and its further metabolites were investigated using Escherichia coli B tester strains. When H/r30R (wild-type; Exc+Rec+) and Hs30R (uvrA-; Exc-Rec+) cells were incubated with DMAA for 3 h in liquid NB medium, many more revertants appeared in sealed tubes than in the control, but this was not the case in unsealed tubes, suggesting that volatile metabolites of DMAA caused the mutagenesis. By gas chromatography-mass spectrometry (GC-MS), dimethylarsine and trimethylarsine, known to be volatile metabolites in microorganisms, were detected in the gas phase of DMAA-added tester strain cell suspensions in sealed tubes. Among these arsines, dimethylarsine was mutagenic in WP2 (wild-type; Exc+Rec+) and WP2uvrA (uvrA-; Exc-Rec+), while trimethylarsine was not. The mutagenesis induced by dimethylarsine required oxygen gas in the assay system; the number of revertants markedly increased in an oxygen-replaced system and diminished in a nitrogen-replaced one. These results suggest that the reaction product(s) between dimethylarsine and molecular oxygen is responsible for the mutagenesis. The significance of this mutagenesis in the genetoxic action of inorganic arsenics is discussed.View full abstractDownload PDF (609K) -
Hitoshi MANABE, Hideo UTSUMI, Akira HAMADA1989 Volume 37 Issue 10 Pages 2757-2761
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of the host lattice on the antigenicity of glycophorin in membranes was confirmed by complement-dependent immune lysis of liposomes with two rabbit antisera, which were prepared by immunization with either human red blood cells or isolated glycophorin A. The immune lysis by either antiserum depended on the kind of phospholipid in the liposomes. Anti-glycophorin antiserum more strongly recognized glycophorin in egg-lecithin membranes than in dipalmitoyl-lecithin membranes, as did anti-red blood cell antiserum. Cholesterol in the liposomal membranes influenced the antigenicity of glycophorin.The relationship between the state of glycophorin in membranes and recognition by antibody is discussed.View full abstractDownload PDF (742K) -
Yoshiko SONODA, Yoshio SEKIGAWA, Yoshihiro SATO1989 Volume 37 Issue 10 Pages 2762-2765
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMetabolism of 32-oxo-24, 25-dihydrolanosterols (3β-hydroxylanost-8-en-32-al (4, Δ8-CHO) and 3β-hydroxylanost-7-en-32-al (5, Δ7-CHO)) was studied in a reconstituted system consisting of rat liver partially purified cytochrome P-450, which catalyzes lanosterol 14-demethylation (P-45014DM), and reduced nicotineamide adenine dinucleotide phosphate (NADPH)-cytochrome P-450 reductase. The reconstituted system converted Δ8-CHO (4) to 4, 4-dimethyl-5α-cholesta-8, 14-dien-3β-ol (2, 8, 14-Diene), which corresponds to the 14-deformylated product. Δ7-CHO (5), the isomer of Δ8-CHO (4), was not converted to the corresponding 14-deformylated product. The apparent Km value of cytochrome P-45014DM for Δ8-CHO (4) was about 1/20 of that for 24, 25-dihydrolanosterol (1, DHL). The metabolism of Δ8-CHO (4) was inhibited by 7-oxo-24, 25-dihydrolanosterol (6, 7-oxo-DHL), which is a potent inhibitor of cholesterol biosynthesis from lanosterol or DHL (1). However, the metabolism of Δ8-CHO (4) was less inhibited by 7-oxo-DHL (6) than that of DHL (1).View full abstractDownload PDF (590K) -
Takako YOKOZAWA, Hae Young CHUNG, Tae Woong LEE, Hikokichi OURA, Takas ...1989 Volume 37 Issue 10 Pages 2766-2769
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of magnesium lithospermate B isolated from Salviae miltiorrhizae Radix on excretion of urinary arachidonate metabolites was examined in both normal rats and those given adenine. Urinary excretion of prostaglandin E2 (PGE2) and 6-keto-prostaglandin F1α (6-keto-PGF1α) decreased while urinary thromboxane B2 (TXB2) excretion increased markedly with the progression of renal failure. Rats administered magnesium lithospermate B showed an increase of urinary PGE2 excretion at the 6th and 12th days. Excretion of 6-keto-PGF1α also showed a significant increase on the 6th and 12th days in rats with renal failure induced by the administration of adenine. However, these effects were lower than the corresponding values in normal rats. In addition, urinary PGE2 and 6-keto-PGF1α excretions showed no appreciable difference in rats that exhibited progressive renal failure with continuation of the adenine administration period, as shown on the 18th and 24th days. There were no significant changes in TXB2 excretion between the control and magnesium lithospermate B-treated groups throughout the experimental period.View full abstractDownload PDF (655K) -
Tadashi KIHO, Masahiko ITO, Isao YOSHIDA, Katsuyuki NAGAI, Chihiro HAR ...1989 Volume 37 Issue 10 Pages 2770-2772
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA water-insoluble glucan (CI-6P), [α]20D+7.3°(c=0.30, 0.5 M sodium hydroxide), was isolated from the alkaline extract of the insect-body portion of Chan hua (Chinese name)(fungus : Cordyceps cicadae), and its molecular weight was estimated by gel filtration to be ca. 21000. From the results of methylation analysis, periodate oxidation, Smith degradation, enzymic hydrolysis, partial acid hydrolysis, and carbon-13 nuclear magnetic resonance spectroscopy, it was concluded that CI-6P was composed of a backbone of β-(1→3)-linked D-glucopyranosyl residues, and side chains of a single, β-(1→6)-linked D-glucopyranosyl group attached, on average, to every 25th residue of the backbone. CI-6P and its carboxymethylated glucan exhibited antitumor activity against sarcoma 180 in mice.View full abstractDownload PDF (546K) -
Jun KISUGI, Masatoshi YAMAZAKI, Yasuhiro ISHII, Shigeru TANSHO, Koji M ...1989 Volume 37 Issue 10 Pages 2773-2776
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel cytolytic factor, dolabellanin A, was purified to apparent homogeneity from the albumen gland of the sea hare Dolabella auricularia. Purified dolabellanin A was a glycoprotein of 250 kilo daltons containing 4 subunits. The amino acid composition and the N-terminal amino acid sequence of the factor were also determined. The factor is distinct from antineoplastic glycoproteins previously isolated from another sea hare, Aplysia kurodai. These results suggest that dolabellanin A found in the sea hare of the Dolabella species is a new cytolytic factor.View full abstractDownload PDF (625K) -
Shigenori TSUDA, Kazunobu DOHARA, Goro SHINJO1989 Volume 37 Issue 10 Pages 2777-2781
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of formulation factors, particularly the valving system, on the spray characteristics such as spray-droplet size and delivery rate were evaluated using aerosol formulations consisting of kerosene and a mixture of propane/butane. The liquid/propellant ratio was fixed at 60/40 by weight and the pressure of the propellant was 4.8 kg/cm2 (gauge) at 20°C. The spray-droplet size was measured by using the laser-diffraction drop-sizing method. The sizes of the three orifices in the valving system (stem orifice [ST], vapor-phase tap orifice [VT] and actuator orifice [BU]) affected both the spray-droplet size and the delivery rate. The bigger the size of ST and BU and the samaller the size of VT, the greater the delivery rate. The spray-droplet size was affected by the mutual interactions among ST, BU and VT. The spray-droplet size dcreased as the size of VT increased when ST was larger than BU or was not much smaller than BU. The effect of VT to reduce spray-droplet size did not appear when BU was too much larger than ST. When VT was small enough or absent, the smallest spray-droplet size was obtained when the ST/BU ratio was around one. When VT was large, the spray-droplet size decreased as the ST/BU ratio increased. It was concluded that the balance of sizes of the three orifices was very important to obtain the most suitable spray characteristics.View full abstractDownload PDF (654K) -
Eihei FUKUOKA, Midori MAKITA, Yasuo NAKAMURA1989 Volume 37 Issue 10 Pages 2782-2785
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe glassy state of indomethacin was examined by thermomechanical analysis (TMA). The influences of the method of preparation and the measurement conditions of the sample on the TMA curves were investigated. The TMA curves of glassy indomethacin having hemispherical and plane surfaces were examined. Expansion was observed on the TMA curves in the region of glass transition temperature (Tg), which had been confirmed by differential scanning calorimetry. The TMA curves for the sample with the plane surface showed distinct expansion. It was further found that the glass transition shifted to lower temperatures as the heating rate was decreased and the loading increased. The TMA curves of brucine, griseofulvin and phenobarbital were similar to that of indomethacin. The relaxation process of glassy indomethacin below Tg was followed in terms of the variation of mechanical properties of samples.View full abstractDownload PDF (541K) -
Yukio ASO, Sumie YOSHIOKA, Yasushi TAKEDA1989 Volume 37 Issue 10 Pages 2786-2789
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of α-, β-, γ- and dimethyl-β-cyclodextrins (α-, β-, γ- and DM-β-CyDs) and liposomes on epimerization or racemization of etoposide, ethiazide and carbenicillin were examined kinetically. α- and β-CyDs accelerated both epimerization and hydrolysis of carbenicillin. They had no effect on epimerization of etoposide, and did not affect racemization and hydrolysis of ethiazide. DM-β-CyD retarded epimerization of etoposide, hydrolysis of picroetoposide (which is an epimer of etoposide), and racemization and hydrolysis of ethiazide, but had no effect on epimerization and hydrolysis of carbenicillin. γ-CyD retarded epimerization of etoposide and hydrolysis of picroetoposide. On the other hand, γ-CyD accelerated epimerization of carbenicillin. It is suggested that the formation of inclusion complexes between CyDs and etoposide, picroetoposide and ethiazide inhibited the attack of bases such as OH- and buffer components, thereby retarding epimerization, racemization and hydrolysis. On the other hand, α-, β- and γ-CyDs increased the reactivity of carbenicillin through the OH group, accelerating its epimerization and hydrolysis. Liposomes retarded epimerization of etoposide, hydrolysis of picroetoposide and racemization of ethiazide. Liposomes did not affect epimerization and hydrolysis of carbenicillin. These differences in the effect of liposomes on reactivity may be interpreted in terms of the solubility of the drugs.View full abstractDownload PDF (604K) -
Kaname OHARA, Yuri HIRANO, Hisao ISHIDA, Takashi FUJITSU, Takaharu ONO ...1989 Volume 37 Issue 10 Pages 2790-2794
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe characteristics of fever elicited by the cell wall skeleton of Nocardia rubra (N-CWS) and by lipopolysaccharide (LPS) were compared in rabbits, and the possible involvement of the antigenicity of N-CWS was investigated in guinea pigs.In rabbits, fever of more than 0.5°C developed after an intravenous (i.v.) injection of 10 μg/kg or more of N-CWS, and was monophasic with 30-100 μg/kg but biphasic with the highest dose of 300 μg/kg. LPS elicited fever with similar characteristics at doses of 0.01-0.1 μg/kg. With both compounds, the fever was inhibited by indomethacin. Tolerance to N-CWS and LPS appeared after dosing with 30 or 0.1 μg/kg, respectively for 10 d.In guinea pigs sensitized with N-CWS, challenge with 1 or 10 μg/kg of N-CWS 10 d later, which did not induce fever in the nonsensitized animals, caused fever of more than 0.5°C, and delayed-type hypersensitivity (DTH) appeared. N-CWS also elicited fever in nonsensitized guinea pigs bearing N-CWS-sensitized lymphocytes or anti-N-CWS antibody; the fever was higher in the guinea pigs sensitized with the lymphocytes than in those with the anti-N-CWS antibody.In brief, single injections of N-CWS and of LPS elicited fever with similar characteristics, although the potency of N-CWS was weaker. With N-CWS, the fever is proposed to be triggered by the antigenicity of the compound itself, because doses as low as 1 or 10 μg/kg elicited fever along with immunological response in N-CWS-sensitized animals, but not in nonsensitized ones.View full abstractDownload PDF (723K) -
Kaname OHARA, Yuri HIRANO, Hisao ISHIDA, Jo MORI, Akira TENSHO1989 Volume 37 Issue 10 Pages 2795-2798
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTumor necrosis factor (TNF), a cytokine produced in macrophages, also acts as an endogenous pyrogen (EP). To investigate whether TNF has a role in the fever induced by Nocardia rubra cell wall skeleton (N-CWS), the relationship between fever and TNF production was studied in guinea pigs.N-CWS injected i.v. to guinea pigs caused biphasic fever and had L-929 cell-killing activity which resembled that of TNF in the sera 30 min before the first phase of fever appeared. In vitro, L-929 cell-killing activity was demonstrated in the culture supernatant of guinea pig peritoneal macrophages pretreated with N-CWS, and the activity increased dependently on N-CWS concentration or culture duration. When the supernatant of the macrophages was fractionated by gel filtration and each fraction was assayed for fever-inducing and L-929 cell-killing activities, the fraction with the cell-killing activity also induced fever with characteristics similar to that by i.v. injection of N-CWS in guinea pigs.These results suggest that TNF acts as an EP on the fever induced by N-CWS in guinea pigs.View full abstractDownload PDF (616K) -
Yukihiro OZAKI, Setsuko SEKITA, Soekeni SOEDIGDO, Masatoshi HARADA1989 Volume 37 Issue 10 Pages 2799-2802
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe red leaves of Graptophyllum pictum (L.) GRIFF. (G. pictum) are used in Indonesian folk medicine. The present study was carried out to elucidate the antiinflammatory effect of the ethanol extract obtained from this crude drug. The extract was partitioned between ether and water, and then the water-soluble fraction was extracted with 1-butanol. The 1-butanol-soluble fraction was extracted with chloroform-acetone, hot methanol and water, successively, and the hot methanol-soluble fraction (fr.) was chromatographed (frs. I-III). The antiinflammatory activity of these fractions was investigated on carrageenin-induced edema in rats and acetic acid-induced vascular permeability as well as the writhing symptom in mice. The ethanol extract (p.o.) showed an antiinflammatory activity as well as an analgesic activity and these activities shifted to the water-soluble fraction, 1-butanol-soluble fraction, methanol-soluble fraction and fr. II, successively. It was found that fr. II contained flavonoids. These results suggest that these flavonoids are at least partly responsible for the antiinflammatory effect of the ethanol extract of G. pictum.View full abstractDownload PDF (607K) -
Keizo MATSUO, Yoko HASUIKE1989 Volume 37 Issue 10 Pages 2803-2806
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA practical synthetic route for 2-aroyl-4, 4-dimethyl-2-buten-4-olides was developed. 10-Aryl-3a, 9-dihydro-1H, 3H-furo[4, 3-b][1, 5]benzothiazepin-1-ones were synthesized from 2-aroyl-4, 4-dimethyl-2-buten-4-olides and 2-amin-othiophenol in good yields.View full abstractDownload PDF (687K) -
Katashi MATSUMOTO, Hisashi MIYAZAKI, Toshihiko FUJII, Hideki AMEJIMA, ...1989 Volume 37 Issue 10 Pages 2807-2810
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mode of binding of sulfonamides to erythrocyte proteins and possible drug-drug interaction between those compounds in erythrocytes resulting in changes in tissue levels were studied in rats using zonisamide (a novel antiepileptic agent possessing a sulfonamide group), several other sulfonamides and some antiepileptics without a sulfonamide group.In Michaelis-Menten plottings, the sulfonamide was found to be concentrated into erythrocytes in vitro and in vivo in a saturable high-affinity mode and in a linear low-affinity mode at ordinary therapeutic plasma levels through a simple diffusion process. Concentration in erythrocytes was affected by the presence of albumin in the extracellular medium. The cellular sulfonamide was readily replaced by extracellular sulfonamides in vitro. Even in vivo, erythrocyte levels of zonisamide were lowered by administration of other sulfonamides, although the plasma and tissue levels were not significantly changed since the plasma and tissue compartments of zonisamide were large relative to the erythrocyte compartment at ordinary therapeutic dose levels of zonisamide in animals and man. Therefore, disposition of zonisamide was not significantly influenced by other sulfonamides, but it is suggested that drug-drug interaction affecting the tissue levels may occur for a combination of sulfonamides with extremely different affinities for erythrocytes and low therapeutic plasma levels.View full abstractDownload PDF (713K) -
Saburo SHIMABAYASHI, Takayoshi SANNOH, Masayuki NAKAGAKI1989 Volume 37 Issue 10 Pages 2811-2813
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntrinsic viscosity and cloud point of an aqueous solution of polyvinylpyrrolidone (PVP) were measured as a function of the concentration of another added polymer, sodium carboxymethylcellulose (NaCMC) or sodium chondroitin sulfate (Na2Chs). The intrinsic viscosity of PVP decreased with increase in the concentration of NaCMC or Na2Chs owing to the volume effect of the polymer coils. The intrinsic viscosity of NaCMC or Na2Chs decreased more remarkably in the presence of PVP K-90 (M.W.=1.19×106) than in the presence of PVP K-30 (M.W.=4.20×104) because the volume effect of polymer coils of PVP K-90 was stronger than that in the case of PVP K-30. The cloud point of an aqueous solution of PVP decreased with increase in the concentration of another added polymer (Na2Chs or NaCMC) and inorganic salt (Na2CO3) because the polymer coils of PVP shrank and the affinity of PVP for water decreased with increase in the concentrations of these additives.View full abstractDownload PDF (454K) -
Yoshinori KONDO, Ryo WATANABE, Takao SAKAMOTO, Hiroshi YAMANAKA1989 Volume 37 Issue 10 Pages 2814-2816
Published: October 25, 1989
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe arylation of 2-, 4-, and 5-halopyrimidines with aryltributylstannanes in the presence of dichlorobis-(triphenylphosphine)palladium was investigated with successful results. The reaction can be expanded to the synthesis of 2-, 4-, and 5-vinylpyrimidines with generality. The site-selectivity of the reaction for 4, 5-dihalopyrimidines is also described.View full abstractDownload PDF (450K)