All issues
Volume 34, Issue 3
Displaying 1-50 of 71 articles from this issue
-
NGUYEN HYU DUNG, BERNARD VIOSSAT, JEAN-CHARLES LANCELOT, MAX ROBBA1986 Volume 34 Issue 3 Pages 951-956
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSC8H5O3N3S2 crystallizes in space group P21/c with Dm=1.56 (2) in a mixture of dimethyl-formamide and methyl ethyl ketone. On the other hand, in acetone, the title compound crystallizes in space group C2/c with lattice parameters a-25.66 (4), b=7.360 (5), c=11.05 (8)Å, β=105.0 (3)°; Z=8; Dm=1.70 (2), Dx=1.68Mg·m-3. The molecular structure was investigated by X-ray diffraction analysis of a single crystal; the final R value was 0.04 for 1823 reflections. The molecules related by a center of symmetry lie one above the other along the b axis and these stacks are linked by intermolecular hydrogen bonding between N-H…N of the amidic group and the thiazole ring, respectively.View full abstractDownload PDF (580K) -
MASAYUKI NAKAGAKI, RYOSUKE TAKAGI1986 Volume 34 Issue 3 Pages 957-965
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe theory of asymmetric membrane potential is developed for a membrane system having a large asymmetric membrane charge distribution. The theory suggests that there are two kinds of typical asymmetric membrane potential profiles : 1) the membrane potential shows both a minimum and a maximum depending upon the bulk concentration, and 2) it shows either a minimum or a maximum. A parameter which represents the asymmetry of the distribution of the membrane charge density was introduced into the theory. A collodion membrane asymmetric with respect to the membrane charge density was prepared to experimentally check the validity of the theory. The experimental results were in agreement with the theory.View full abstractDownload PDF (714K) -
KAZUNOBU HARANO, RIE KONDO, MOTOJI MURASE, TOSHIKAZU MATSUOKA, TAKUZO ...1986 Volume 34 Issue 3 Pages 966-974
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the 1, 3-dipolar cycloaddition reaction of 3-methylpyridine N-oxide with phenyl isocyanate, spectroscopic evidence indicates that phenyl isocyanate forms charge-transfer complexes with both pyridine N-oxide and aromatic solvents such as pyridine. In connection with the charge-transfer complex formation, the solvent effect on the site selectivity was investigated. The most prominent solvent effect was observed in the reaction using 3-methylpyridine as a solvent. The equilibrium constants for the interaction of 3-methylpyridine N-oxide with phenyl isocyanate in several solvents were found to be quite large, indicating that the reaction mixtures favor complex formation. The proton nuclear magnetic resonance (1H-NMR) spectra of the mixtures show a high field shift of the methyl signal of 3-methylpyridine N-oxide due to charge-transfer complexation. Based on these results, the structure and role of the complexes are discussed.View full abstractDownload PDF (829K) -
MASAICHIRO MASUI, SEIJIRO HARA, SHIGEKO OZAKI1986 Volume 34 Issue 3 Pages 975-979
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIndirect electrochemical oxidation of amides and N-alkyllactams was performed using N-hydroxyphthalimide as a mediator. A carbonyl group was introduced in good yield at the α-carbon to the nitrogen of the compounds.View full abstractDownload PDF (453K) -
MAKOTO MIYAHARA, MICHIKO MIYAHARA1986 Volume 34 Issue 3 Pages 980-985
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Phenyl-3-(pyridylmethyl)ureas (I) were nitrosated with sodium nitrite under acidic conditions to give two positional isomers, 1-nitroso-1-phenyl-3-(pyridylmethyl)urea (II) and 3-nitroso-1-phenyl-3-(pyridylmethyl)urea (III). The nitrosation was carried out using several nitrosating reagents under various conditions, and each isomer was determined by means of high-performance liquid chromatography. The regioselectivity depended on the medium and reagents used. With gaseous nitrosating reagents in organic solvents at 0°C, I generated mainly III. The combination of sodium nitrite and acid (1 M perchloric acid, 1 M hydrochloric acid or 99% formic acid) gave II predominantly. However, with N2O3, the predominant product was dependent on the pH of the medium. The differences of chemical and antitumor activity of the nitroso isomers were also examined.View full abstractDownload PDF (622K) -
YOSHIO OKADA, NORIYA OHTA, SHIN IGUCHI, YUKO TSUDA, HIDEAKI SASAKI, TO ...1986 Volume 34 Issue 3 Pages 986-998
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA nonacosapeptide corresponding to the N-terminal sequence 1-29 (β-fragment) of human liver metallothionein II (hMT II) was synthesized by the azide coupling of five peptide fragments [1, 2, 4, 6 and 8], followed by HF deprotection and its heavy metal-binding properties were examined. It was revealed that the Cd-binding ability of the synthetic β-fragment as well as synthetic α-fragment corresponding to the C-terminal sequence 30-61 of hMT II was stronger than that of native rat thionein. Moreover, it was found that both the α-and β-fragments bound preferentially to Cu ions rather than Cd ions.View full abstractDownload PDF (1361K) -
KATSUMI FUJIMOTO, YUJI IWANO, KOICHI HIRAI, SHINICHI SUGAWARA1986 Volume 34 Issue 3 Pages 999-1014
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe azetidinone derivative (6), which has an (R)-hydroxyethyl substituent at the C-3 position, was prepared efficiently from 6-aminopenicillanic acid. From the dibromo seco derivative (10), compounds of the same type (16 and 17), but in dl-form, were obtained. Compounds 6 and 16 were reacted with various thiocarboxylic acids to obtain the penem derivatives (23a-n).The minimum inhibitory concentration values of these penems against various microorganisms were, determined, and the structure-activity relationship is discussed.View full abstractDownload PDF (1724K) -
NOBUTOSHI TANAKA, HIDEO SAKAI, TAKAO MURAKAMI, YASUHISA SAIKI, CHIU-MI ...1986 Volume 34 Issue 3 Pages 1015-1022
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new ent-rosane type norditerpenes, ar-maximic acid (I) and ar-maximol (II), were isolated from the fronds of Arachniodes maximowiczii OHWI, and were shown to have the structures of 2-hydroxy-19-nor-ent-rosa-1, 3, 5(10), 15(16)-tetraene 18-oic acid (I) and 2, 18-dihydroxy-19-nor-ent-rosa-1, 3, 5(10), 15(16)-tetraene (II) by chemical, spectroscopic and X-ray crystallographic methods. In addition, six glycosides of acyclic terpenes were isolated, and their structures were elucidated as 3(S)-linalool O-β-D-glucopyranoside (III), 3(S)-linalool O-β-D-(6'-O-β-L-fucopyranosyl)glucopyranoside (IV), 13-hydroxygeranyllinalool 13-O-β-D-(6'-O-β-L-fucopyranosyl)glucopyranoside (V), 13-hydroxygeranyllinalool 3, 13-O-β-D-diglucopyranoside (VI), 13-methoxygeranyllinalool O-β-D-glucopyranoside (VII) and 15-methoxy-3, 7, 11, 15-tetramethylhexadeca-1, 6(E), 10(E), 13(E)-tetraene O-β-D-glucopyranoside (VIII), mainly by spectroscopic methods. Compounds VII and VIII, obtained as an inseparable mixture may be artefacts. Maltol and maltol β-D-glucoside were also isolated.View full abstractDownload PDF (898K) -
AKIO OHSAWA, IKUO WADA, HIROSHI IGETA1986 Volume 34 Issue 3 Pages 1023-1031
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome pyridazinium N-ylides underwent 1, 3-dipolar cycloaddition with perhalocyclopropenes and with a perhalocyclobutene. Thermal decomposition and chemical transformations of the pyrolyzed products afforded various hitherto unknown 2-chloropyrazolo[1, 5-b]pyridazine derivatives.View full abstractDownload PDF (838K) -
MASARU NIITSU, KEIJIRO SAMEJIMA1986 Volume 34 Issue 3 Pages 1032-1038
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinds of linear pentaamines with various combinations of 3 or 4 methylene chain intervals were synthesized. The methods were tentatively classified into two, leading to symmetrical and unsymmetrical pentaamines, all of which were prepared by successive alkylation of secondary amino derivatives of benzylamine with N-(3-bromopropyl or 4-bromobutyl)phthalimide in the presence of KF-Celite, coupled with the purification of the phthaloyl compounds by silica gel column chromatography. Protecting benzyl and phthaloyl groups were removed by usual methods. The carbon-13 unclear magnetic resonance (13C-NMR) spectra of the ten pentaamines were recorded in D2O as fully protonated forms, and a comparative analysis of their spectra allowed the complete assignment of all 13C chemical shifts.View full abstractDownload PDF (760K) -
TAKASHI TANAKA, GEN-ICHIRO NONAKA, ITSUO NISHIOKA1986 Volume 34 Issue 3 Pages 1039-1049
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA chemical examination of the leaves of Terminalia catappa L. (Combretaceae) has led to the isolation and characterization of four new hydrolyzable tannins named terflavins A (1) and B (2), tergallagin (3) and tercatain (4), together with eight known tannins : punicalin (5), punicalagin (6), chebulagic acid (7), geraniin (8), granatin B (9), 1-desgalloyleugeniin (10), corilagin (11) and 2, 3-[(S)-4, 4', 5, 5', 6, 6'-hexahydroxydiphenoyl]-D-glucose (12). Terflavins A (1) and B (2) possess novel structures in which a flavogallonyl (triphenyl) ester group is single bonded to the glucopyranose ring, and are presumed to be biosynthetic precursors of punicalagin (6) and punicalin (5), respectively, while tergallagin (3), which contains a gallagyl (tetraphenyl) group and a unique tergalloyl ester group attached to the glucose moiety, seems to be formed biosynthetically from punicalagin (6).View full abstractDownload PDF (974K) -
NOBUO IKOTA, HIROSHI SAKAI, HISANARI SHIBATA, KENJI KOGA1986 Volume 34 Issue 3 Pages 1050-1055
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMetalation and alkylation of the chiral imines prepared from cyclohexanone and methoxy amines (2b, 4c, 6d, and 7d) derived from D-camphor derivatives provided, after hydrolysis, optically active 2-alkylcyclohexanones (9) in high enantiomeric purities of up to 99.5%.View full abstractDownload PDF (635K) -
MASAHIRO NAGAI, NAOKI KENMOCHI, MASAO FUJITA, NAOKO FURUKAWA, TAKAO IN ...1986 Volume 34 Issue 3 Pages 1056-1060
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo diarylheptanoid glycosides, named aceroside VII (8), C25H34O8, mp 144-145°C, [α]15D -28.4°, and aceroside VIII (9), C30H42O12, [α]15D -64.8° were isolated from the stem bark of Acernikoense MAXIM. (Aceraceae). On acid hydrolysis 8 yielded (-)-centrolobol (10) and glucose, while 9, on partial hydrolysis, gave 8 and apiose. Acerosides VII (8) and VIII (9) were determined to be the 3-O-β-D-glucopyranoside and the 3-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside of (-)-centrolobol (10), respectively, on the basis of carbon-13 nuclear magnetic resonance (13C-NMR) spectral analyses and additional chemical data.The absolute configuration S for (-)-centrolobol (10) has been claimed, but the authors propose its revision to R(-) on the basis of Brewster's empirical rule on the correlation between absolute configuration and optical rotation. The stereochemistries of some compounds related to 10 such as acerogenin A (1) and (-)-centrolobin should also be revised. At the same time, partial revision of the 13C-NMR signal assignments for acerosides III (3) and VI (4) is also necessary.View full abstractDownload PDF (635K) -
YASUMITSU TAMURA, TAKAYUKI YAKURA, YOSHIAKI SHIROUCHI, JUN-ICHI HARUTA1986 Volume 34 Issue 3 Pages 1061-1066
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of α-acylsulfides with phenyl iodosyl bis(trifluoroacetate) (PIFA) resulted in a Pummerer-type reaction to give the same products as obtained by the Pummerer reaction of the α-acylsulfoxides. The Pummerer-type reaction of α-acylsulfides using PIFA was applied to Friedel-Crafts type cyclization of N-phenyl-α-(methylthio)acetanilide (1) and ethyl α-(1-phenethylthio)-acetate (9) to give N-phenyl-3-(methylthio)oxindole (3) and ethyl isothiochroman-1-carboxylate (10), respectively, olefin cyclization of α-(methylthio)acetamides (11, 13 and 15) to give the lactams (12, 14 and 16), and also intermolecular condensation and α-methoxylation of methyl α-(methylthio)acetate (7).View full abstractDownload PDF (596K) -
SACHIKO TSUKAMOTO, KOJI HAYASHI, KOH KANEKO, HIROSHI MITSUHASHI, MOTOO ...1986 Volume 34 Issue 3 Pages 1067-1074
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel disaccharide named wilforibiose (1) was isolated from the acidic hydrolysate of the crude glycoside of Cynanchum wilfordi HEMSLEY. The structure of 1 was deduced on the basis of chemical and spectral evidence, and was confirmed to be β-D-glucopyranose L-olivopyranose 1', 4 : 2', 3-dianhydride by X-ray analysis.View full abstractDownload PDF (717K) -
HIDESHI INOUE, MASAAKI HIROBE1986 Volume 34 Issue 3 Pages 1075-1079
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCupric ion catalytically enhances the autoxidation of L-ascorbic acid. The cleavage of disulfide occurred in the copper(II)/ascorbic acid system and was inhibited by catalase and by scavengers of hydroxyl radical, so that the hydroxyl radical was considered to be formed and to cleave the disulfide. Insulin was denatured by this system, but in this case the inhibitors were less effective. It seems likely that cupric ion was bound to insulin and that locally generated hydroxyl radical caused the damage. Cytokinins, which are plant growth regulators and retard leaf senescence, effectively inhibited the above reactions in the copper(II)/ascorbic acid system.View full abstractDownload PDF (489K) -
NOBUYUKI IMAI, MARI NEMOTO, YOSHIYASU TERAO, KAZUO ACHIWA, MINORU SEKI ...1986 Volume 34 Issue 3 Pages 1080-1088
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sodium hydride-aided reaction of N-(phenylthiomethyl)-α-amino acid esters with α, β-unsaturated carboxylates results in a pyrrolidine-forming 1, 3-dipolar cycloaddition. Thus, a new route to pyrrolidines, pyrrolizidines, and indolizidines has been provided.View full abstractDownload PDF (827K) -
MAKOTO TAKEMURA, KUNIO HIGASHI, HIROYUKI FUJIWARA, MAKOTO SATO, MINORU ...1986 Volume 34 Issue 3 Pages 1089-1093
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new type of thienamycin derivative (2) having a monothioacetal side chain at the C-2 position was prepared by means of a replacement reaction of protected thienamycin sulfoxide (13) with the monothiohemiacetal (16) liberated in situ by the retro-Michael reaction of the masked thiol (12) with 1, 8-diazabicyclo[5.4.0]undec-7-ene.View full abstractDownload PDF (546K) -
TOZO FUJII, TOHRU SAITO, NORIHIKO TERAHARA1986 Volume 34 Issue 3 Pages 1094-1107
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn H2O at near neutrality, the 1-(ω-hydroxyalkyl)adenine derivatives 8a, b·HBr and 8c·HClO4 underwent hydrolytic deamination to give the 1-(ω-hydroxyalkyl)hypoxanthine derivatives 10a-c, in competition with the usual Dimroth rearrangement to produce the N6-(ω-hydroxyalkyl)adenine derivatives 9a-c. The rates of these competitive reactions were measured in H2O at various pH's and ionic strength 1.0 at 40°C, and the relative rate of deamination with respect to Dimroth rearrangement was found to increase as the pH of the reaction medium was decreased. Under similar conditions, the corresponding 1-alkyl analogues 8d-g·HClO4 and the 1-(modified benzyl) analogues 8h, i·HBr underwent only Dimroth rearrangement to afford the N6-isomers 9d-i. In the Dimroth rearrangements of all of the substrates 8a, b, d-i·HX (X=Br or ClO4), attack of hydroxide ion on the protonated species (8a, b, d-i·H+) at the 2-position was faster than that on the neutral species by a factor of 100-640. In the reaction of the protonated species, the 1-(ω-hydroxyalkyl) analogues 8a, b·HBr rearranged faster than the corresponding 1-alkyl analogues 8e, f·HClO4 by a factor of 1.6-2.7. It has been concluded that this rate enhancement is attributable solely to the electron-withdrawing effect, and not to intramolecular participation in catalysis, of the hydroxy group in the 1-substituent chain. In the syntheses of 8a, i·HBr from 9-ethyladenine (6) according to a general 1-alkylation procedure, the 7-alkylated products 13 and 16 were also obtained as by-products in 9% and 6% yields, respectively.View full abstractDownload PDF (1401K) -
KEIJI KUBO, KIYOSHI UKAWA, SEIJI KUZUNA, AKIRA NOHARA1986 Volume 34 Issue 3 Pages 1108-1117
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(3-Carboxy-5-oxo-5H[1]benzopyrano[2, 3-b]pyridin-2-yl)acetic acid derivatives (3 and 4) were found to possess potent antiarthritic activity in the rat adjuvant arthritis model. The mode of action of these compounds differs from that of acidic antiinflammatory drugs. Various modifications in these compounds (e.g., elongation, removal, or substitution of the methylene group of the acetic acid moiety; and substitution of the benzene ring) were made in order to study the structure-activity relationships. However, it was found that the structural requirements for the compounds to show activity are rather severe.View full abstractDownload PDF (970K) -
KAZUO OGAWA, TADAFUMI TERADA, YOSHIYUKI MURANAKA, TOSHIHIRO HAMAKAWA, ...1986 Volume 34 Issue 3 Pages 1118-1127
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMany 1-substituted 2-alkanone derivatives were synthesized and their inhibitory activities toward pancreatic lipase and esterase were examined in order to obtain hypolipidemic agents. 1-Benzenesulfonyloxy-2-pentanone (VI-2a) and 1-(2, 4, 6-trimethylbenzenesulfonyloxy)-2-pentanone (VI-2q) exhibited not only potent and selective esterase inhibitions (IC50 : 9.0×10-7M and 1.0×10-6M, respectively), but also potent hypolipidemic action (90 and 92% reductions of plasma triglyceride, and 53 and 90% reductions of plasma total cholesterol, respectively). A novel working hypothesis is presented to account for the lowering of the plasma lipids level, i.e., that inhibition of esterase and lipase activities in the small intestinal lumen may be responsible for the decrease in the plasma lipids level.View full abstractDownload PDF (1000K) -
KATSUMI ITOH, MASAKUNI KORI, YOSHIYUKI INADA, KOHEI NISHIKAWA, YUTAKA ...1986 Volume 34 Issue 3 Pages 1128-1147
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe design and synthesis of new structural types of angiotensin converting enzyme (ACE) inhibitors, (R)-3-amino-4-oxo-2, 3, 4, 5-tetrahydro-1, 5-benzothiazepine-5-acetic acids (7, 26, 33 and 37) and (S)-3-amino-4-oxo-2, 3, 4, 5-tetrahydro-1, 5-benzoxazepine-5-acetic acids (8 and 27), are described. A number of compounds in these series showed potent ACE inhibitory activity in vitro and in vivo. The structure-activity relationship is also discussed.View full abstractDownload PDF (1547K) -
MARIE LAVAULT, ALAIN FOURNET, HELENE GUINAUDEAU, JEAN BRUNETON1986 Volume 34 Issue 3 Pages 1148-1152
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNine isoquinoline alkaloids belonging to the protoberberine, proaporphine and bisbenzyl-isoquinoline series were isolated from Caryomene olivascens (Menispermaceae). Four compounds are new : (-)-2-norlimacine (4), (-)-caryolivine (6), (+)-1, 2-dehydro-2-norlimacusine (9) and N-formylstepharine (3). The last one is the first N-formyl derivative to be reported in the proaporphine group. Its biogenetic origin is discussed. Structures were established on the basis of 360 MHz (FT) nuclear magnetic resonance measurements and also by chemical correlation in the case of 3.View full abstractDownload PDF (576K) -
HIDEAKI MATSUDA, KENSUKE NAMBA, SEIYA FUKUDA, TADATO TANI, MICHINORI K ...1986 Volume 34 Issue 3 Pages 1153-1157
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe activites of seven ginsenosides isolated from Red Ginseng on blood coagulative and fibrinolytic systems closely related to disseminated intravascular coagulation were investigated in in vitro models and compared with those of standard agents (aspirin, heparin and dextran sulphate).Ginsenoside-Rg2 showed strong inhibitory activity on platelet aggregation induced by three aggregating agents (endotoxin, collagen and arachidonic acid) as compared with aspirin at a concentration of 1.0 mM. Ginsenoside-Ro inhibited the conversion of fibrinogen to fibrin induced by thrombin at concentrations of 0.1 to 1.0 mM. Ginsenoside-Ro, -Rb1, -Rb2, -Rc, -Re, -Rg1 and -Rg2 may promote the action of urokinase in the fibrinolytic system on the basis of its action on plasminogen-containing fibrin plates.View full abstractDownload PDF (531K) -
JING-KAI DING, HIROKO FUJINO(nee KIMATA), RYOJI KASAI, NAOKO FUJIMOTO, ...1986 Volume 34 Issue 3 Pages 1158-1167
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSaponins were isolated from roots of Bupleurum marginatum (Zhuye-Chaihu), B. marginatum var. stenophyllum (Zezhuye-Chaihu) and B. rockii (Lijiang-Chaihu) collected in Yunnan, China, and identified. For the evaluation of these plants as a medicine, quantitative analysis of pharmacologically active saponins, saikosaponins-a (1) and -d (3), in the plants was also conducted in comparison with B. falcatum and B. chinensis.View full abstractDownload PDF (844K) -
TSUKASA HAMADA, MASANA KADOWAKI, YURIKO NAKAMURA, NORIO AWATA1986 Volume 34 Issue 3 Pages 1168-1171
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA gas chromatographic method for the quantitative determination of the new antiallergic agent, 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazole difumarate (KB-2413), in plasma has been developed. This method, which was based on solvent extraction and flexible fusedsilica capillary gas chromatography with a nitrogen-sensitive detector and a moving needle solvent cut sample injector, is simple, sensitive and selective.The detection limit was about 1 ng (as free base)/ml and the calibration curve was linear over the range of 2 to 100 ng/ml. Moreover, the intra- and inter-assay coefficients of variation for the determination of KB-2413 were 3.1-4.0% and 1.5-6.7%, respectively. This assay was applied to the determination of the plasma concentration of KB-2413 base after oral administration to dogs.View full abstractDownload PDF (468K) -
AKIRA TAKADATE, HIROYUKI FUJINO, MASAHIRO OBASA, SHUJIRO GOYA1986 Volume 34 Issue 3 Pages 1172-1175
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSo-Phthalaldehyde (OPA) was found to react with sodium sulfite in borate buffer (pH 9.9) to form a fluorescent product (λex 360nm, λem 424nm), which was stable only in the solution. The fluorescence of the product in alkaline solution was stable for at least 6h. Hydrosulfite and pyrosulfite showed the same degree of fluorescence intensity as sulfite. Other sulfur compounds gave little or no fluorescence. The working curve for sodium sulfite was linear in the range of 0.2-7.0nmol/2ml. The detection limit of sodium sulfite was 0.2nmol/2ml. The presence of metal ions had practically no influence on the fluorescence intensity of the OPA-sodium sulfite system. However, contamination with ammonium ion and amines should be avoided in the determination of sulfite. The fluorescent product seems to be formed through a mechanism different from that of isoindole formation, but its structure has not yet been determined.View full abstractDownload PDF (495K) -
YOSHIMASA ITO, MASAHIRO IWAKI, TARO OGISO, KAZUYUKI HIRANO, MAMORU SUG ...1986 Volume 34 Issue 3 Pages 1176-1183
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method was developed for the determination of liver and pancreas dipeptidase activities in serum by using specific antibody-conjugated paper disks. The immunoreaction between the antibody-conjugated paper disks and the dipeptidases reached a plateau within 7h at 4°C, and no dipeptidase activity was detected in the reaction medium thereagter. The calibration curves obtained by the proposed method passed through the origin and were linear in the ranges of 0-200 ng of liver dipeptidase and 0-37.5 ng of pancreas dipeptidase. The bound enzymes from human liver and pancreas had higher Km values and lower Vmax values toward L-Leu-L-Leu than those of the corresponding free enzymes. However, with L-Ala-L-Ala as a substrate, the Km and Vmax values of the pancreas dipeptidase bound on the paper disk and the free enzyme were almost the same. The recoveries of added liver and pancreas dipeptidases from serum were more than 96%. The proposed method showed a good precision. The normal value of liver dipeptidase activity in serum was 1.62±0.40 I.U./l of serum (mean±S.D.). The activities were elevated in acute hepatitis (18.7±18.2 I.U./l, p<0.001 vs. normal) and liver cancer (12.3±12.9 I.U./l, p<0.001). The normal value of pancreas dipeptidase activity in serum was 0.74±0.99 I.U./l of serum. The activities were remarkably elevated in pancreatic cancer (5.22±2.68 I.U./l, p<0.001) and acute pancreatitis (4.82±2.84 I.U./l, p<0.001). These results suggest that this method may be useful in the clinical diagnosis of hepatic and pancreatic diseases.View full abstractDownload PDF (759K) -
KIMIKO AOKI, MIDORI AOKI, YASUHARU HIRAI, YUKIO KUROIWA1986 Volume 34 Issue 3 Pages 1184-1188
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA competitive enzyme immunoassay for cinobufagin with alkaline phosphatase-labeled cinobufagin and polyethylene glycol as a precipitant was developed. The anti-cinobufagin antisera produced in rabbits by immunization with cinobufagin 3-hemisuccinate-bovine serum albumin conjugate efficiently recognized 14β, 15β-epoxy, 16β-acetoxy and 17β-six-membered unsaturated lactone structures, and therefore showed high affinity for cinobufagin and cinobufotalin. The range of cinobufagin measurable by the enzyme immunoassay was 10-500 pg/tube. Plasma cinobufagin levels of dogs and cats were determined after i.v. and p.o. administrations.View full abstractDownload PDF (558K) -
YOUICHI FUJII, MASANORI TERANISHI, MINEHIRO MIZUKAMI, HARUYO UKARI, MI ...1986 Volume 34 Issue 3 Pages 1189-1194
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA radioimmunoassay method for the quantitative determination of plasma 2-hydroxyestriol has been developed. For the purpose of obtaining antiserum for this compound, 6-oxo-2-hydroxyestriol was converted to its 6-(O-carboxymethyl)oxime derivative and then coupled with bovine serum albumin by means of the mixed anhydride technique. The immunization of rabbits with this conjugate produced anti-2-hydroxyestriol antiserum which showed high affinity and specificity with low cross-reactivities to structurally related estrogens. After extraction of pregnancy plasma with ethyl acetate and purification on a Sephadex LH-20 column, 2-hydroxyestriol was measured by radioimmunoassay. The following mean concentrations were found in pregnancy plasma : 1st trimester (28.4 pg/ml), 2nd trimester (37.7 pg/ml), and 3rd trimester (104.1 pg/ml).View full abstractDownload PDF (720K) -
Chronic Effect of Saikosaponin on Adrenal and Thymus Growth in Normal and Dexamethasone-Treated RatsSUSUMU HIAI, HIROOMI YOKOYAMA1986 Volume 34 Issue 3 Pages 1195-1202
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of repeated intraperitoneal administration of total saikosaponin or saikosaponin d from Bupleuri Radix on the wet weight of the adrenals and thymus, and on the resting level of plasma corticosterone were determined in intact or hypophysectomized rats. Total saikosaponin or saikosaponin d increased the relative weight of the adrenals with respect to the initial body weight, decreased the relative weight of the thymus, and did not affect the resting evening level of plasma corticosterone in normal intact rats. A moderate, but not high, dose of saikosaponin administered with dexamethasone antagonized the atrophic effect of dexamethasone on the adrenals. Moderate and high doses of saikosaponin acted synergistically on dexamethasone-induced atrophy of the thumus, but it did not significantly affect the resting dexamethasone-depressed level of plasma corticosterone. In hypophysectomized rats, a high dose of saikosaponin d did not affect the weight of either the adrenals or the thymus, whereas exogenous adrenocorticotropin markedly increased the adrenal weight but not the thymus weight, and dexamethasone did not decrease the adrenal weight but markedly decreased the thymus weight.View full abstractDownload PDF (853K) -
TATEKI YAMAMOTO, MASAO KOBAYASHI, MASAYOSHI KOBAYASHI1986 Volume 34 Issue 3 Pages 1203-1211
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA substance that stimulates dentinal fluid transport (DFT) through the dentinal tubules in the molar teeth of rats was found in bovine parotid glands. This DFT-stimulating substance was purified by aqueous extraction, isoelectric precipitation, ultrafiltration, gel filtration on Sephadex G-75 and chromatofocusing. By these procedures, 37 mg of purified preparation was obtained from 1 kg of bovine parotid gland. The purified preparation showed a single band on both disc polyacrylamide gel electrophoresis and sodium dodecyl sulfate (SDS)-polyacrylamide gel electrophoresis. A dose of 10 μg of the purified DFT-stimulating substance per kg of body weight was positive in the bioassay for DFT-stimulating activity, as indicated by the migration of a fluorescent dye through the dentinal tubules in the molar teeth of rats.The molecular weight of DFT-stimulating substance was estimated to be 30000 by both gel filtration on Sephadex G-75 and SDS-polyacrylamide gel electrophoresis. The isoelectric point was found to be pH 6.0 by isoelectric focusing. This active substance was composed of a total of 263 amino acid residues per molecule, had a maximum absorption wavelength (λmax) of 280 nm and an extinction coefficient (E1%1cm) at 280 nm of 15.4, contained less than 1% carbohydrate, and appeared to consist of a single polypeptide chain.View full abstractDownload PDF (1145K) -
KIYOMI KIKUGAWA, MASUMI ARAI1986 Volume 34 Issue 3 Pages 1212-1218
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe intermediates of methemoglobin [MetHb] were investigated by the use of an intramolecular cross-linking agent, bis(3, 5-dibromosalicyl)fumarate. The cross-linked Hb A [HbFu], which cannot split into αβ-dimers, was oxidized with potassium ferricyanide, sodium nitrite and seasamol. In every oxidation, cross-linked hemoglobins with 1-met, 2-met, 3-met, and 4-met [MeHbFu] subunits were formed. As the oxidation level increased, the contents of the hemoglobins with higher amounts of met subunits increased. MetHbFu may be produced via the hemoglobins with 1-met→2-met→3-met subunits. The hemoglobins with 1-met and 3-met subunits may each contain two valency asymmetrical hybrids. Whereas analysis by isoelectrofocusing showed that Hb A partially oxidized with potassium ferricyanide contained Hb A, α+2β2, α2β+2 and MetHb, all being symmetrical hybrids, treatment of the oxidized Hb A with the cross-linking agent gave corss-linked hemoglobins with 3-met subunits (valency asymmetrical hybrids) besides those with 2-met and 4-met subunits. In the course of oxidation of native Hb A, unstable valency asymmetrical hybrids may be initially produced but may split into the αβ-dimers which recombine and form stable valency symmetrical hybrids under analysis.View full abstractDownload PDF (780K) -
SETSURO SUGATA, AKIRA KONO, YASUHIRO HARA, YOSHIHARU KARUBE, YOSHIKAZU ...1986 Volume 34 Issue 3 Pages 1219-1222
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA thymidine phosphorylase (TP) preparation was partially purified from human gastric cancer (poorly differentiated adenocarcinoma). The specific activity of the final preparation represented a 379-fold purification of the 7000g supernatant of tissue homogenate. The phosphorolytic activities toward thymidine (dThd), 5'-deoxy-5-fluorouridine (5'-DFUR), and 1-(tetrahydro-2-furanyl)-5-fluorouracil (Tegafur) remained closely in parallel during the whole purification procedure. The results provide evidence in support of the assumption that 5'-DFUR and Tegafur are converted into 5-fluorouracil, an activated form of the antitumor agents, in humn tumor tissues by a TP activity. The values of Km of the TP preparation were 1.68×10-4, 1.72×10-3, 1.33×10-2, and 4.76×10-2M for dThd, 5'-DFUR, Tegafur, and uridine, respectively.View full abstractDownload PDF (455K) -
YOSHIYUKI KIMURA, HIROMICHI OKUDA, TARO NOMURA, TOSHIO FUKAI, SHIGERU ...1986 Volume 34 Issue 3 Pages 1223-1227
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of various flavonoids and related compounds isolated from the root bark of mulberry tree on rat platelet lipoxygenase and cyclooxygenase products formed from [1-14C] arachidonic acid were studied. Morusin was found to inhibit the formations of 12-hydroxy-, 8, 10-heptadecatrienoic acid (HHT) and thromboxane B2 (cyclooxygenase products) more strongly than the formation of 12-hydroxy-5, 8, 10, 14-eicosatetraenoic acid (12-HETE) (12-lipoxygenase product). Oxydihydromorusin and kuwanon C were also found to inhibit the formation of thromboxane B2 more strongly than the formations of HHT and 12-HETE. Mulberrofuran A inhibited the formations of HHT and thromboxane B2, but it increased the formation of 12-HETE. Albanol B and mulberrofuran F did not affect arachidonate metabolism in rat platelet homogenates.View full abstractDownload PDF (526K) -
TOSHIO INAGI, TOYOJIRO MURAMATSU, HIROSHI TERADA1986 Volume 34 Issue 3 Pages 1228-1234
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe interactions of the potent antiinflammatory agent indomethacin with diisopropyl adipate and n-octanol were studied under various conditions. Diisopropyl adipate has been used as a typical additive in preparations for the percutaneous absorption of indomethacin, and n-octanol is known to form hydrogen-bonds with various drugs. The association constants were determined from the change in the partition of indomethacin between n-hexane containing diisopropyl adipate or n-octanol and water. Both the neutral and anionic forms of indomethacin were found to associate with these additives in a 1 : 2 molar ratio, but with different association constants. The association of indomethacin with n-octanol was found to be dependent on pH, but that with diisopropyl adipate was independent on pH. The affinity of indomethacin for diisopropyl adipate was much smaller than that of the neutral form of indomethacin for n-octanol. It was also found, from an analysis of the solubilities of indomethacin in various esters, that the association constants of indomethacin with esters are about the same. The weak, but pH-independent association of indomethacin with diisopropyl adipate is suggested to be important for the induction of percutaneous absorption of indomethacin.View full abstractDownload PDF (640K) -
SHIGEO TANAKA, YASUJI TAKASHIMA, KENJI TSUNODA, MAKOTO TAKAHASHI, HIRO ...1986 Volume 34 Issue 3 Pages 1235-1241
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe physicochemical properties of the solid state of hydrocortisone butyrate propionate (HBP) were determined by thermal analysis of the solid phase. In addition, the solubility of HBP was measured in a wide variety of solvents. The physicochemical properties and solubility of HBP obtained experimentally were compared with those reported for hydrocortisone (HC).The solid phase of HBP showed a lower melting point (122°C) and heat of fusion (4.98kcal/mol) than those of HC. The activity of the solid phase of HBP was significantly higher than that of HC. The solubility parameter of HBP estimated from the solubility in various solvents was 11.2 (cal/ml)1/2. This value is lower than that of HC, which was reported as 12.4 (cal/ml)1/2. Further, the solubility parameter of HBP was closer to that of skin, which was reported as 9.7-10.0 (cal/ml)1/2.Consequently, it is considered that the high release ability from topical preparations and the high percutaneous absorption of HBP are due to the high activity of solid phase and the fact that the solubility parameter is close to that of skin.View full abstractDownload PDF (592K) -
YOSHINOBU NAKAI, KEIJI YAMAMOTO, KATSUHIDE TERADA, TAKESHI UCHIDA, KEI ...1986 Volume 34 Issue 3 Pages 1242-1248
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal structure of the second polymorphic form of the title compound (α-form : Chem. Pharm. Bull., 30, 2629 (1982)) has been determined by X-ray diffraction analysis of a single crystal. The crystal of the β-form, C8H9FN2O3, is monoclinic, space group P21/n, with a=11.891 (5), b=14.556 (2), c=5.062 (1)Å, β=99.05 (2)°, U=865.3 (4)Å3, Mr=200.17, Z=4; Dc=1.54, Dm=1.54 gcm-3, F(000)=416, λ(Mo Kα)=0.7107Å, μ=1.433 cm-1. The structure was solved by the direct method using the MULTAN 78 program. Refinement by the full-matrix least-squares method gave a final R factor of 0.055 (1669 independent reflections). Bond lengths and angles agree well with those of both molecules in the α-form. The molecular conformation is very similar to one of those in the α-form. The cyclic dimer structure of the β-form is different from that of the α-form.View full abstractDownload PDF (545K) -
HIROSHI KIWADA, SAKAE OBARA, HIROKO NISHIWAKI, YURIKO KATO1986 Volume 34 Issue 3 Pages 1249-1256
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUptake of liposomes by perfused rat liver was examined, and the effluent profiles are discussed. Reverse-phase evaporation vesicles (REV, about 0.1-0.2 μm in diameter) were able to pass through the liver without any interaction or interference and there was little uptake by the liver during single perfusion with phosphate-buffered saline. The transit time of REV was shorter than that of inulin simultaneously injected as a flow marker. These results suggest that the uptake of REV by the liver requires opsonization by blood components, and if REV can escape opsonization, they may be able to pass through the liver freely. It is also clear that the distribution volume of the REV is smaller than that of inulin.On the other hand, small unilamellar vesicles (SUV, about 0.06 μm in diameter) showed uptake corresponding to about 0.25 μmol of total lipid without any participation of blood components. This result suggsts that the uptake mechanism of SUV may be different from that of REV, and opsonization may not be essential for the uptake of SUV by the liver. A comparison of the results for REV and SUV suggests that the functional pore size of the fenestration of liver sinusoids is about 0.06 μm, and about half of the SUV prepared in this study could pass through the fenestration and reach the hepatocytes, while the other part of the SUV drained through the liver as did REV.The uptake of SUV by the liver seemed to be limited in capacity, and it was influenced by temperature and inhibited by predosing with liposomes containing sodium azide or cytochalasin B.View full abstractDownload PDF (768K) -
MASAYA MORIMOTO, KENJI YAMASHITA, HIROYOSHI KOYAMA, HITOSHI FUJIMOTO, ...1986 Volume 34 Issue 3 Pages 1257-1263
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bioavailability and pharmacokinetics of molsidomine (SIN-10) from a capsule containing wax-coated beads, were compared with those from a conventional tablet in dogs and monkeys during the formulation study of a sustained release dosage form of SIN-10. Sustained-release capsules (SR capsules) A, B and C contained coated beads with different amounts of wax, and SR capsule D contained 20% immediate release beads and 80% wax-coated beads. In dogs, SR capsules A and B did not satisfactorily prolong the effective plasma concentration. With capsule C, although satisfactory maintenance of effective plasma concentration was obtained, the bioavailability was only to half of that after administration of a conventional tablet. On the other hand, in monkeys, reasonable prolongation of effective plasma concentration (depending upon the amount of wax coating) with satisfactory bioavailability was obtained for each SR capsule. With an SR capsule D, more than 12h duration of effective plasma concentration of molsidomine and control of blood pressure from immediately after administration of the capsule were achieved in monkeys.View full abstractDownload PDF (675K) -
SHIGERU ITAI, SHOZO KOUCHIWA, MASAMI NEMOTO, HIROSHI MURAYAMA, TSUNEJI ...1986 Volume 34 Issue 3 Pages 1264-1274
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of compression pressure and a disintegrant on the dissolution profile of flufenamic acid (FFA) in tablets were evaluated in relation to the time course of the available surface area (S(t)). The ratios of S(t) generated by time t to the total S(t) generated during the dissolution process (F(t)), which it was possible to obtain from dissolution tests on the tablets as well as on granules before compression, were well regreassed to the Weibull distribution and the log-normal distribution. The scale parameter (a) and the shape parameter (b) of the Weibull distribution increased as the compression pressure was increased, and also as the level of disintegrant was decreased. With regard to the regression to the log-normal distribution, the standard deviation (σ) of the S(t)-generated pattern increased as the compression pressure was increased, whereas it was unaffected by the level of disintegrant. By using the probability parameters thus obtained, the S(t)-generation patterns of FFA (200 mg) tablets at various compression pressures were simulated. When the compression pressure was low, and the disintegrant level was high, the patterns had a well-defined peak value, which was consistent with the disintegration time of the tablets.View full abstractDownload PDF (839K) -
TADAKAZU TOKUMURA, YUKI TSUSHIMA, KIMIO TATSUISHI, MASANORI KAYANO, YO ...1986 Volume 34 Issue 3 Pages 1275-1279
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis investigation was aimed at the improvement of the bioavailability of cinnarizine (CN) by administering its β-cyclodextrin (β-CD) complex together with a competing agent. The ability of L-leucine (L-Leu) and L-isoleucine (L-Ileu) to act as competing agents was evaluated by determining the penetration rate of CN, employing a Sartorius absorption simulator. L-Ileu showed a stronger competing action than L-Leu. The bioavailability of CN, upon oral administration of the CN-β-CD inclusion complex, was enhanced by the simultaneous administration of L-Ileu as a competing agent; Cmax was 1.9 and 2.7 times those of CN-β-CD complex alone and CN alone, respectively. L-Leu showed no clear effect on the bioavailability. The in vivo competing effects of L-Leu and L-Ileu appeared to be in agreement with the in vitro evaluations.View full abstractDownload PDF (495K) -
SHIGERU ITAI, MASAMI NEMOTO, SHOZO KOUCHIWA, HIROSHI MURAYAMA, TSUNEJI ...1986 Volume 34 Issue 3 Pages 1280-1288
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe initial rate of increase (Kh) of available surface area (S(t)) of flufenamic acid (FFA) in tablets during the disintegration and deaggregation (dispersion) processes, as well as the rate of decrease (Kd) of S(t) during the subsequent dissolution process, was determined by using two approaches. One was based on the assumption that the increase and decrease are dependent in a first-order manner on S(t) generated at time t. The other was based on the assumption that the initial rate of increase of S(t) is independent of S(t), whereas the subsequent rate of decrease is dependent on the S(t) at time t. By using the S(t) equations developed from these two approaches, the ratio of the S(t) generated by time t to the total S(t) generated during the dissolution process (F(t)) could be expressed as a function of time, which included Kh and Kd as the constants. Furthermore, from the non-linear regression of F(t) data, which it is possible to obtain from a dissolutio study, to these F(t) functions, well-matching Kh and Kd values for the FFA (200 mg) tablets could be obtained. The influence of the level of disintegrant and the compression pressure on Kh and Kd, as well as the results of simulation of the S(t)-generation patterns of FFA (200 mg) tablets are also discussed.View full abstractDownload PDF (716K) -
YOSHIHISA MATSUDA, SACHIYO KAWAGUCHI1986 Volume 34 Issue 3 Pages 1289-1298
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour modifications (monohydrate, hemihydrate, anhydrate, and amorphous form) of oxyphenbutazone were prepared and characterized by the use of X-ray powder diffractometry, thermal analysis, infrared spectrophotometry, and elemental analysis. The physicochemical stability of the amorphous form was quantitatively investigated by X-ray diffractometry at three temperatures (25, 40, and 50°C) and three relative humidity levels (0, 50, and 75%). The amorphous form transformed to the anhydrate at low humidity, while it transformed to either the hemihydrate or the monohydrate at moderate or high humidity. These hydrates also converted to the anhydrate via the amorphous state at low humidity. The anhydrate did not transform under any storage conditions and showed the highest stability. Increase of temperature greatly acdelerated the transformation rate, but the transformation mechanism was not changed.Among the four modifications the dissolution properties of the hydrates were unexpectedly superior to those of the anhydrate or amorphous form.View full abstractDownload PDF (880K) -
AKIRA KUSAI, SEIGO UEDA1986 Volume 34 Issue 3 Pages 1299-1308
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics and mechanisms of the degradation of carboquone (CQ) in methanol were investigated.Eight peaks were observed as degradation products of CQ in high performance liquid chromatography, suggesting that the degradation process of CQ in methanol is rather complicated. However, conducting the reaction in proton-rich methanol and methylate-rich methanol made it clear that CQ is degraded in methanol through a combination of two mechanisms : methanolysis of the aziridine ring, which cleaved to a (2-methoxyethyl)amino group, and substitution of the aziridine ring by methylate. Further, some of the degradation products were obtained in pure form by this procedure.Due to the asymmetric structure of CQ, two kinds of mono aziridinyl-mono methoxyethyl-amino compounds and two kinds of mono aziridinyl-mono methoxy compounds are produced. Kinetic studies of these four compounds and 2, 5-bis(1-aziridinyl)-3, 6-dimethyl-1, 4-benzoquinone made it possible to assign their chemical structures. Their deduced structures were confirmed by mass spectroscopy and proton nuclear magnetic resonance spectroscopy.View full abstractDownload PDF (833K) -
KEN-ICHI SASAKI, MINORU SASAKI, MASAAKI ISHIKAWA, GIICHI TAKAYANAGI1986 Volume 34 Issue 3 Pages 1309-1314
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of lentinan (1 mg/kg/12h×4, i.p.) on the hepatic cytochrome P-450 molecular species and the cytochrome P-450-dependent monooxygenase activities was observed in ddY and C57BL/6 mice treated with phenobarbital (8 or 40 mg/kg/d×2, i.p.) or 3-methylcholanthrene (80 mg/kg, i.p.). The activities of aminopyrine N-demethylase, aniline hydroxylase and biphenyl 4-hydroxylase were elevated by 20-37% by the treatment with phenobarbital, and these increases were unaffected by concurrent administration of phenobarbital and lentinan. The activities of 7-ethoxycoumarin O-deethylase and biphenyl 2-hydroxylase were increased by 74-192% by the treatment with 3-methylcholanthrene, but these increases were depressed by the combination treatment with 3-methylcholanthrene and lentinan. It was found by an sodium dodecyl sulfate-polyacrylamide gel electrophoretic study that the suppression by lentinan of the elevation of cytochrome P-450-dependent monooxygenase activities induced by 3-methylcholanthrene was caused by a decrease in the hepatic microsomal cytochrome P-450 content.View full abstractDownload PDF (747K) -
JUN-ICHI UEDA, AKIRA HANAKI, NAOKO YOSHIDA, TERUMI NAKAJIMA1986 Volume 34 Issue 3 Pages 1315-1318
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA proton nuclear magnetic resonance (1H-NMR) study of the interaction of zinc(II) ion with glycylglycyl-L-histidine (Gly-Gly-His) was carried out. The addition of zinc(II) ion affected the NMR spectrum of Gly-Gly-His above pH 6; the signal of the imidazole C-2 proton underwent line broadening and upfield shift, and that of the methylene proton of glycine at the amino terminal was also shifted upfield. It is suggested that Gly-Gly-His functions as a bidentate ligand, coordinating with the zinc(II) ion through the amino nitrogen and the neighboring peptide oxygen, and that the imidazole nitrogen of the complex is linked intermolecularly to the zinc(II) ion of another peptide complex.View full abstractDownload PDF (455K) -
KOJI YAMAKAWA, KIYOSHI NISHITANI, MITSUGI IIDA, AKIKO MIKAMI1986 Volume 34 Issue 3 Pages 1319-1322
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntroduction of a hydroxyl group at the C-8β position of l-α-santonin (1) was achieved by chemical and microbiological methods. The chemical transformation of 1 was accomplished via the 8β-hydroxy compound (5b) derived from 3, 8-dioxoeudesm-1, 4, 6-triene (4). The enol acetate 7 of the 8β, 12-olide (6) derived from 5b was treated with hydrogen peroxide in formic acid, giving the 6α-hydroxy-8β, 12-olide (8). Compound 8 was converted into 8-epiartemisin (2b) by hydrolysis of the ester group followed by lactonization.The microbiological transformation of 1 into 2b was performed by the use of Aspergillus sp. MIL 5024.View full abstractDownload PDF (552K) -
YASUO TAKEUCHI, KEIKO SAKAGAWA, MASUMI KUBO, MASATOSHI YAMATO1986 Volume 34 Issue 3 Pages 1323-1327
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of sulfides from alcohols and benzoxazoline-2-thione (I) was studied to establish its generality and the mechanism of the reaction. A one-flask synthesis of sulfides from alcohols was developed. According to this procedure, various sulfides were prepared without the use of illsmelling thiols. Moreover, partial sulfenylation of diols to give sulfenyl alcohols was achieved.View full abstractDownload PDF (532K) -
MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, EIJI IMAI, YUKIHARU MATS ...1986 Volume 34 Issue 3 Pages 1328-1332
Published: March 25, 1986
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSXanthinium N7-ylides were generated in situ from 7-substituted 9-methylxanthinium tosylates (2) using n-BuLi in tetrahydrofuran or Et3N in MeCN. The xanthinium N7-ylides (3) generated using Et3N in MeCN reacted with diphenylcyclopropenone to give pyrone derivatives and isocaffeine in good yields. The reactions of 3a-b with dimethyl acetylenedicarboxylate or methyl propiolate (MP) afforded 5-pyrrol-1-yluracils in moderate yields. N7-Methoxycarbonylmethylide (3c) reacted with MP to give a pyrrolopteridine derivative together with a 5-pyrrol-1-yluracil derivative. Furthermore, the dihydropyrrolopurine derivative (7), a primary 1, 3-dipolar cycloaddition product, was detected by nuclear magnetic resonance measurement of the products.View full abstractDownload PDF (586K)