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Volume 31, Issue 11
Displaying 1-50 of 64 articles from this issue
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TOYOHISA TSUKAMOTO, SHUSHI MORITA, JUTARO OKADA1983 Volume 31 Issue 11 Pages 3785-3795
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidation of D-glucose on immobilized enzyme catalyst was carried out in a trickle-bed reactor operated in a single-pass or batch-recycle manner. The catalyst, with β-D-glucose oxidase and catalase both immobilized on activated carbon, was prepared by the carbodiimide method. The experiments were performed at atmospheric pressure, 25°C and pH=5.5 (in 0.1M acetate buffer). The rate equation for this enzymatic reaction and the mass balance equations in the reactor are proposed. The experimental results were well explained by these equations. The important factors which influence the global rate of reaction are the liquid-solid contacting efficiency, the mass transfer of oxygen in the liquid (gas-liquid, liquid-solid and intraparticle) and the mutarotation of D-glucose. The batch-recycle trickle-bed reactor with low conversions per pass was found to be preferable.View full abstractDownload PDF (912K) -
JUNICHI ODO, YUTAKA SAITO, YOSHIMASA TANAKA1983 Volume 31 Issue 11 Pages 3796-3801
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe infrared spectra of bis (L-and DL-phenylalaninato) copper (II) and their N-deuterated analogues have been recorded in the region between 4000 and 200cm-1. The vibrational assignments of the Cu-ligand stretching vibrations have been made by means of the metal isotope technique, 63Cu and 65Cu substitution. Three bands of trans-bis (L-phenylalaninato) copper at 400, 380, and 339cm-1 shift appreciably on 63Cu-65Cu substitution. The blue isomer of bis (DL-phenylalaninato) copper also shows three copper isotope-sensitive bands at 380, 340, and 328cm-1, analogous to those of trans-bis (D-alaninato)-and (L-phenylalaninato) copper. However, the blue-violet isomer of the DL complex shows only two sensitive bands at 370 and 322cm-1, as in the case of cis-bis (D-alaninato) copper. Frequency shifts on N-deuteration suggest that one of the Cu-N stretching vibrations is at higher frequency than the Cu-O stretching vibrations for bis (L-phenylalaninato) copper, but this frequency order is reversed for the two isomers of bis (DL-phenylalaninato) copper, but this frequency order is reversed for the two isomers of bis (DL-phenylalaninato) copper.View full abstractDownload PDF (616K) -
JUNICHI ODO, MASAAKI NISHIO, YUTAKA SAITO, YOSHIMASA TANAKA, KATSUNOSU ...1983 Volume 31 Issue 11 Pages 3802-3810
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe infrared spectra of bis (L-serinato) copper (II) and -zinc (II) and their isotopic complexes containing metal and hydrogen isotopes have been measured in the region between 4000 and 200cm-1. By referring to the isotope shifts, four bands of the Cu complex at 375, 327, 307, and 255cm-1 have been assigned to the Cu-OOC and the Cu-NH2 stretching vibrations. Two bands of the Zn complex at 230 and 295cm-1 have been assigned to Zn-OOC and Zn-NH2 stretching vibrations, respectively. By comparing the Cu complex with the Zn complex, the vibrations of two anisostructural serinates included in the Zn complex have been distinguished from each other. The structural difference between the two serinates was clearly reflected in the COO deformation vibrations. The Raman measurement for a single crystal of the Zn complex revealed rather small factor group splittings. A normal coordinate analysis for the Zn complex was carried out by using a complete molecular conformation and an intermolecular force field. The result is consistent with the empirical assignments and the experimental isotope shifts.View full abstractDownload PDF (815K) -
KAZUE SATOH, TADASHI MIYASAKA1983 Volume 31 Issue 11 Pages 3811-3818
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of oxazolo [3, 2-b] pyridazinium perchlorates (I) with hydroxylamine hydrochloride and potassium hydroxide in N, N-dimethylformamide afforded 2-(2, 3-dihydro-3-hydroxyimino-2-pyridazinyl) ethanones (II) and 2-(2, 3-dihydro-3-hydroxyimino-2-pyridazinyl) ethanone oximes (III), from both of which imidazo [1, 2-b] pyridazine 1-oxides (IV) were synthesized by heating in meneral acid. The N-oxides were characterized by converting them into the corresponding imidazopyridazines by deoxygenation.View full abstractDownload PDF (701K) -
ITSUO YOSHIZAWA, SHINJI ITOH, KYOKO NAGATA, NORIO KAWAHARA1983 Volume 31 Issue 11 Pages 3819-3828
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to elucidate the mechanism of D-homoannulation of pregnanediol 20-sulfate, solvolysis of [13C-20]-5β-pregnane-3α, 20α-diol disulfate (3) in refluxing 3N hydrochloric acid was investigated. The resulting D-homosteroids, 17α-methyl-D-homo-5β-androstane-3α, 17aβ-diol (8) and 17α-methyl-17aβ-chloro-D-homo-5β-androstan-3α-ol (10), contained a quantitative amount of 13C only at C-17, indicating that the ring-enlargement reaction of the 20α-ol sulfate proceeded with stereospecific migration of the C16-C17 bond. The same result was obtained from isomeric [13C-20]-5β-pregnane-3α, 20β-diol disulfate (6). Based on these results, the D-homoannulation of pregnanediol 20-sulfate was concluded to proceed by a stepwise mechanism through the C-20 carbocation. The stereochemistry of this Wagner-Meerwein type rearrangement reaction is also discussed.View full abstractDownload PDF (917K) -
KENICHI HARADA, SUSUMU ITO, MAKOTO SUZUKI, TAKASHI IWASHITA1983 Volume 31 Issue 11 Pages 3829-3843
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSporaviridin is a basic and water-soluble antibiotic produced by Streptosporangium viridogriseum. During separation and purification of N-acetylsporaviridin, we found that this derivative was hydrolyzed by aqueous ammonia used as the eluent for column chromatography to yield glycosidic compounds containing an aglycone and three pentasaccharides, designated as viridopentaoses A, B and C. The purfication of these compounds was performed as shown in Chart 2. They were concluded to be novel heteropentasaccharides (1A, 1B and 1C) containing two or three amino sugars, on the basis of chemical degradations and spectroscopic studies.View full abstractDownload PDF (1491K) -
KENICHI HARADA, SUSUMU ITO, MAKOTO SUZUKI1983 Volume 31 Issue 11 Pages 3844-3854
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe significant features of the carbon-13 nuclear magnetic resonance spectra of viridopentaoses (1A, 1B and 1C), constituent pentasaccharides of N-acetylsporaviridin, and their degradation products (2-9) are discussed. The glycosidation shift was successfully applied to characterize the glycosidic linkages up to the tetrasaccharide level, whereas anomalous behavior was found in the pentasaccharides.View full abstractDownload PDF (805K) -
KENICHI HARADA, SUSUMU ITO, NAOHITO TAKEDA, MAKOTO SUZUKI1983 Volume 31 Issue 11 Pages 3855-3864
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSequence determination of permethylated viridopentaoses and their degradation products was performed by chemical ionization mass spectrometry (CIMS) using isobutane and ammonia as reagent gases. The CI mass spectra show MH+ or (M+NH4)+ ions in the molecular ion region. Fragmentation involving carbon-carbon bond fission rarely occurs. As a major fragmentation, the glycosidic linkage is cleaved between the glycosidic oxygen atom and the anomeric carbon atom. Resulting fragment ions in the isobutane spectra can be classified into oxonium and protonated (with methyl or hydrogen transfer) ions, whereas fragment ions in the ammonia spectra can be divided into oxonium (occasionally with attachment of an ammonia molecule) and ammonium adduct (with methyl or hydrogen transfer) ions. These results are shown to be useful for sequencing unknown oligosaccharides.View full abstractDownload PDF (754K) -
TOSHIKO SATAKE, TAKAO MURAKAMI, YASUHISA SAIKI, CHIUMING CHEN1983 Volume 31 Issue 11 Pages 3865-3871
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new diterpene glycosides (V, VII and IX) were isolated from Lindsaea javanensis, together with lindsaea acid, 2β, 16α-dihydroxy-ent-kaurane 2-O-β-D-glucopyranoside and 16α, 17, 19-trihydroxy-ent-kaurane 19-O-β-D-glucopyranoside. The structures of the new compounds were elucidated by spectroscopic methods as 16α, 19-dihydroxy-ent-kaurane 19-O-β-D-glucopyranoside, 12β, 16α, 17, 19-tetrahydroxy-ent-kaurane 19-O-β-D-glucopyranoside and 12β, 16α, 19-trihydroxy-ent-kaurane 19-O-β-D-glucopyranoside, respectively. From L. japonica, ocoumaric acid was isolated, while lindsaea acid and 2, 6-dimethoxybenzoquinone were isolated from Tapeinidium pinnatum.View full abstractDownload PDF (767K) -
JUNICHI YAMASHITA, MITSUGI YASUMOTO, SADAO HASHIMOTO1983 Volume 31 Issue 11 Pages 3872-3877
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mechanism of the condensation of 5-fluorouracil and 2-acetoxytetrahydrofuran (3), giving 1-(tetrahydro-2-furyl)-5-fluorouracil, was studied. An equilibrium between 2-acetoxytetrahydrofuran (3) and 2, 3-dihydrofuran (4) was observed at 120-170°C in dimethylformamide. It was found by the use of 1, 3-dideuterio-5-fluorouracil that the condensation of 5-fluorouracil with 3 occurred both by direct substitution and by the formation of 4 from 3 followed by addition of the uracil to it. The contribution of the latter path increased with increase of the reaction temperature.View full abstractDownload PDF (532K) -
MASASHI TOMODA, NORIKO SHIMIZU, SHIMIZU KAZUTO, TAKAE ISHII, MOTOKO OG ...1983 Volume 31 Issue 11 Pages 3878-3882
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA mucilage, named Lycoris-S-glucomannan, was isolated from the bulbs of Lycoris squamigera MAXIM. The final preparation was homogeneous as determined by ultracentrifugal analysis, glass-fiber electrophoresis, and gel chromatography. It was mainly composed of D-mannose and D-glucose in the molar ratio of 7 : 2, and its molecular weight was estimated to be about 1800000. O-Acetyl groups were identified in the glucomannan and their content amounted to 16.7%. They were located at positions 2, 6 of about half of the D-mannose units. Methylation, periodate oxidation, and partial acid hydrolysis studies showed that the glucomannan is mainly composed of β-1→4 linked aldohexopyranose residues, and that it contains about twenty aldohexose units per three non-reducing groups on average. D-Mannose units occupy all branching points linked through position 3, while both D-mannose and D-glucose units occupy non-reducing terminal positions.View full abstractDownload PDF (720K) -
MASAO HATTORI, WOLFGANG PFLEIDERER1983 Volume 31 Issue 11 Pages 3883-3890
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPoly-2-methyladenylic acid (poly (m2A)), poly-2-ethyladenylic acid (poly (e2A)) and poly-2-isopropyladenylic acid (poly (iso-pr2A)), which are polyadenylic acid (poly (A)) analogues bearing alkyl groups at the C (2)-position of the adenine moiety, form 1 : 1 complexes with polyxanthylic acid (poly (X)) under the same conditions where poly (A) forms both 1 : 1 and 1 : 2 complexes. In contrast to the base pairing between poly (A) and poly (X), these poly-2-alkyladenylic acids cannot, for steric resons, form normal Watson-Crick type complexes involving the amino group and the N (1)-atom, but coordinate instead with the N (7)-position. Relative rates of complex formation between poly-2-alkyladenylic acids and poly (X) vary with the nature of the alkyl substituents. The half-times for the complex formation were determined for the poly (m2A)-poly (X), poly (e2A)-poly (X) and poly (iso-pr2A)-poly (X) systems as 10min, ∼7h and ∼9h, respectively. In the presence of 0.1M Na+, pH7.0, the poly (m2A)·poly (X) complex does not dissociate below 95°C, but the poly (e2A)·poly (X) and poly (iso-pr2A)·poly (X) complexes show cooperative dissociation at Tms of 84.2 and 69.7°C, respectively. The ultraviolet and circular dichromic spectra of the complexes are also presented and compared with those of poly (A)·poly (X).View full abstractDownload PDF (784K) -
YUICHI HASHIMOTO, TAKAYOSHI ISHIZAKI, KOICHI SHUDO, TOSHIHIKO OKAMOTO1983 Volume 31 Issue 11 Pages 3891-3896
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Acetoxy-2H-1, 4-benzoxazin-3 (4H)-one (3) undergoes rearrangement or nucleophilic attack to give 2-, 5-, 6-, and 7-substituted derivatives of the benzoxazinone according to the reaction conditions. The formation of 5- and 7-substituted products was interpreted in terms of nucleophilic attack on the cation (14) formed by the heterolysis of the N-O bond of 3. For the formation of 6-substituted derivatives of the benzoxazinone, participation of the oxygen atom at position 1 of the benzoxazinone (that is, formation of an oxonium ion, 18) is important. A possible mechanism for the formation of 2-substituted products also involves an oxonium ion (19). These novel aspects of acetoxybenzoxazinone chemistry may contribute to an understanding of the mechanism of the actions of the prohibitins in cereal plants.View full abstractDownload PDF (679K) -
YOSHIHISA KURASAWA, YUJIRO MORITAKI, TERUMI EBUKURO, ATSUSHI TAKADA1983 Volume 31 Issue 11 Pages 3897-3901
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious 3-(1, 3, 4-oxadiazol-2-yl) methylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines (4a, 4b, 5a, 5b, and 6) were prepared from 3-methoxycarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxaline (1) via 3-hydrazinocarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxaline (2) and 3-(substituted hydrazino) carbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxalines (3a and 3b). Compound 3a was also cyclized to 1, 2-dihydro-2-oxo-3-(5-oxo-3-pyrazolin-4-yl) quinoxaline (7).View full abstractDownload PDF (521K) -
SHIGEHISA KYOSAKA, SANAE MURATA, MITSUYA TANAKA1983 Volume 31 Issue 11 Pages 3902-3905
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe rates of hydrolysis of substituted phenyl α-and β-D-mannopyranosides were measured in acidic and alkaline solutions. In 0.11N hydrochloric acid solution, the α-mannosides were hydrolyzed faster than the corresponding β-anomers. The rates of hydrolysis for the α-mannosides were unaffected by substitution in the phenyl group (Hammett reaction constant ρ=-0.07±0.065 (S. D.)), and those for the β-mannosides were slightly enhanced by the introduction of electron-releasing substituents (ρ=-0.25±0.082). In sodium hydroxide solution, the α-mannosides liberated their aglycones, phenols, much faster than the corresponding β-anomers and the rates were enhanced by the introduction of electron-withdrawing substituents (ρ=+2.7±0.14 for the α-, +3.1±0.46 for the β-mannosides, each in 3.93N NaOH). Phenyl α-mannoside was hydrolyzed much faster than phenyl β-glucoside, though both have trans-1, 2 configuration, indicating the importance of a 1, 2-diaxial orientation for the reaction.View full abstractDownload PDF (534K) -
GENICHIRO NONAKA, OSAMU KAWAHARA, ITSUO NISHIOKA1983 Volume 31 Issue 11 Pages 3906-3914
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlong with four dimeric proanthocyanidin gallates, viz. prodelphinidin B-2 3'-O-gallate (IV) and procyanidins B-2 3, 3'-di-O-gallate (V), B-2 3'-O-gallate (VI) and B-4 3'-O-gallate (VII), two novel dimeric flavan-3-ol gallates (VIII and IX) named theasinensins A and B, in which two flavan units are linked at the B-ring, have been isolated from fresh green tea leaves, and their structures have been established on the basis of spectroscopic evidence in conjunction with enzymatic hydrolyses with tannase. Three new monomeric acylated flavan-3-ols have also been isolated, and their structures were similarly characterized as (-)-epigallocatechin 3-O-p-coumaroate (I), (-)-epigallocatechin 3, 3'-di-O-gallate (II) and (-)-epigallocatechin 3, 4'-di-O-gallate (III). In addition, the occurrence of the known (-)-epicatechin 3-O-gallate (X), (-)-epigallocatechin 3-O-gallate (XI), (+)-catechin (XII), (-)-epicatechin (XIII), (-)-epigallocatechin (XIV) and (-)-epicatechin 3-O-(3-O-methyl)-gallate (XV) in green tea leaves was confirmed.View full abstractDownload PDF (863K) -
TAKESHI KATO, TOSHINORI HATTORI, KIYOHISA KAWAI, YOICHI SAWA1983 Volume 31 Issue 11 Pages 3915-3923
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of our search for synthetic non-narcotic analgesics, 2-(substituted) aminomethyl-3-benzyl-5, 5-dimethylcyclohexanones (3) were prepared by the Mannich reaction of 5, 5-dimethylcyclohexanones (2) with secondary amine hydrochlorides. In this reaction, 6-(substituted)-aminomethylcyclohexanones (4) were also obtained as by-products. Reduction of 3 gave the corresponding 2-(substituted) aminomethyl-3-benzylcyclohexanols (5 and 6). The configurations of compounds 3, 5 and 6 were determined to be 2, 3-trans, 1, 2-cis-2, 3-trans, and 1, 2-trans-2, 3-trans, respectively, by analysis of the nuclear magnetic resonance spectral data. Among the tested compounds, 2, 3-trans-3-benzyl-and 3-(3-methoxybenzyl)-2-dimethylaminomethyl-5, 5-dimethylcyclohexanones (3a and 3c) were almost as potent as codeine phosphate as regards analgesic activity determined by the phenylquinone writhing method.View full abstractDownload PDF (850K) -
TAMIO MORIKAWA, KENJI TSUJIHARA, MIKIO TAKEDA, YOSHIHISA ARAI1983 Volume 31 Issue 11 Pages 3924-3930
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of eight 3, 3-disubstituted nitrosoureas (IVa-h) having the nitrosoureido group at the C-6 position of methyl glucopyranoside or methyl 2-acetamido-2-deoxy-glucopyranoside was prepared and tested for antitumor activities. Heating of the 6-O-p-tolylsulfonyl derivatives (I and II) with various alkylamines followed by reaction with 2-chloroethyl isocyanate gave the corresponding ureas (IIIa-h), which were nitrosated with nitrogen tetroxide to give IVa-h in high yields. The nitrosoureas (IVa-h) were significantly less active than the other positional isomers with respect to the nitrosoureido group prepared previously. Compounds IVa-h appear to be activated by a γ hydroxyl group at the C-4 position. The rate of activation, however, proved to be much slower than those of the C-1 or C-3 positional isomers having a β hydroxyl group. The structure-activity relationships of the positional isomers are discussed in the light of this difference in the rate of activation.View full abstractDownload PDF (680K) -
MASAHITO OCHIAI, KENZO SUMI, EIICHI FUJITA1983 Volume 31 Issue 11 Pages 3931-3938
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-(Trimethylsilylmethyl) cyclopropyl ketones were smoothly cleaved with boron trifluorideacetic acid complex under mild reaction conditions with the assistance of the trimethylsilyl group to give γ, δ-enones in good yields. The major effect of the trimethylsilyl group in the ring opening of the cyclopropyl ketones was unambiguously confirmed in the dicyclopropyl ketone 15 : one of its two cyclopropyl rings, which has a trimethylsilylmethyl group, was selectively cleaved. Furthermore, the reaction was applied to the formal total synthesis of cis-jasmone.View full abstractDownload PDF (832K) -
KAZUO ACHIWA, TADASHI MOTOYAMA, MINORU SEKIYA1983 Volume 31 Issue 11 Pages 3939-3945
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDipolar cycloaddition of an intermediary N-acyltrimethylsilylmethyliminium salt formed from N-(benzylidene) trimethylsilylmethylamine and acyl chloride to conjugated alkenes or alkines gave N-acylpyrrolidines or N-acyl-2, 5-dihydropyrroles, respectively. The stereochemistry of all the products was established.View full abstractDownload PDF (601K) -
MASATOSHI YAMATO, YASUO TAKEUCHI, KYOKO HATTORI, KUNIKO HASHIGAKI1983 Volume 31 Issue 11 Pages 3946-3950
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA one-pot synthesis of 2-alkoxybenzoxazole (I) from benzoxazoline-2-thione (II) was achieved. Treatment of benzoxazoline-2-thione with methyl iodide followed by an alcohol at room temperature in the presence of sodium hydride gave I. The reaction involves the intermediate of 2-(methylthio) benzoxazole (IIIa), followed by substitution of the methylthio group by an alkoxide anion. The general applicability of this method is discussed.View full abstractDownload PDF (553K) -
TAKEO HIGASHINO, YASUHIKO MATSUSHITA, MASUMI TAKEMOTO, EISAKU HAYASHI1983 Volume 31 Issue 11 Pages 3951-3958
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen a mixture of 4-aroyl-1-phenyl-1 H-pyrazolo [3, 4-d] pyrimidines (3) and sodium hydroxide in dimethyl sulfoxide (DMSO) was stirred for 1h at room temperature, migration of the aryl group to the 4-position occurred, i. e., the benzilic acid rearrangement, resulting in the formation of 4-aryl-4, 5-dihydro-1-phenyl-1H-pyrazolo [3, 4-d] pyrimidine-4-carboxylic acids (4). Potassium ferricyanide oxidized the carboxylic acids (4) to the corresponding 4-aryl-1-phenyl-1H-pyrazolo [3, 4-d] pyrimidines (5) with elimination of carbon dioxide. Reaction of 5 with sodium hydroxide in DMSO caused ring fission of the pyrazole portion, to give the corresponding 6-anilino-4-aryl-5-pyrimidinecarbonitriles (11).View full abstractDownload PDF (671K) -
KOSAKU HIROTA, KAZUO MARUHASHI, TETSUJI ASAO, NORIHIKO KITAMURA, YOSHI ...1983 Volume 31 Issue 11 Pages 3959-3966
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThermolysis and photolysis of 6-azido-1, 3-dimethyluracils possessing certain substituents (formyl, benzoyl, hydrazonomethyl, phenyl, and benzyl groups) at the 5-position provided new methods for the preparation of fused pyrimidines. Irradiation and heating of 5-formyl-and 5-benzoyl-6-azidouracils (3 and 7) led to the formation of isoxazolo [3, 4-d] pyrimidines (4 and 8). 2-(Substituted amino) pyrazolo [3, 4-d] pyrimidines (14) were conveniently prepared by the reaction of 6-chloro-5-hydrazonomethyl-1, 3-dimethyluracils (12) with sodium azide, followed by thermolysis of the resulting 6-azides. Upon thermolysis and photolysis of 5-phenyl-and 5-benzyl-6-azidouracils (16 and 19), pyrimido [4, 5-b] indole (17) and pyrimido [4, 5-b] quinoline (10) were obtained, respectively. Cyclization of 3 using triethyl phosphite and triphenylphosphine resulted in the formation of a new ring system, pyrimido [4, 5-d] [1, 2, 3] triazine (5).View full abstractDownload PDF (768K) -
YOSHIO TAKEUCHI, MUTSUMI FURUMURA, EIICHI YOSHII1983 Volume 31 Issue 11 Pages 3967-3970
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4, 6-Dideoxy-3, 5-O-isopropylidene-2-O-(methoxymethyl)-DL-glucitol (3) was conveniently prepared from (±)-parasorbic acid (4). Resolution of the racemate 3 into the D-and L-isomers, each of which serves as a synthetic building block for the sugar moiety of naturally occurring (-)-griseusin A (2) or its enantiomer (1), was effected by high-performance liquid chromatography of its benzoate (12) on a column packed with (+)-poly (triphenylmethylmethacrylate) on macroporous silica gel [Chiralpak OT (+)[O!R]].View full abstractDownload PDF (555K) -
SHINICHI YOSHIMURA, HIROMI NARITA, KOJI HAYASHI, HIROSHI MITSUHASHI1983 Volume 31 Issue 11 Pages 3971-3983
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven new glycosides were isolated from the stem of Dregea volubilis (L.) BENTH. The structures of dregeosides Ap1 (1), Ao1 (2), Aa1 (3), A11 (4), C11 (5), Ka1 (6), and Ka1 (7) were deduced on the basis of chemical and spectral evidence as drevogenin A 3-O-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, drevogenin A 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, drevogenin A 3-O-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, drevogenin A 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, drevogenin C 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, drebyssogenin K2 3-O-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, and drebyssogenin K2 3-O-3-O-methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside, respectively. Among them, 1 and 2 were active against Ehrlich carcinoma (solid type), and the latter was also active against melanoma B-16.View full abstractDownload PDF (1161K) -
TADATAKA NORO, YASUSHI ODA, TOSHIO MIYASE, AKIRA UENO, SEIGO FUKUSHIMA1983 Volume 31 Issue 11 Pages 3984-3987
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSXanthine oxidase (XO) inhibitors were isolated from the flowers and buds of Daphne genkwa SIEB. et ZUCC. (Thymelaeaceae) and were identified as genkwanin (1), apigenin (2), luteolin 7-methyl ether (3) and luteolin (4). Compounds 2 and 4 showed particularly strong inhibitory activity against XO. The modes of inhibition by 2 and 4 with respect to xanthine as a substrate were of mixed type. This is the first report of isolation of 3 and 4 from these flowers and buds.View full abstractDownload PDF (516K) -
HIROSHI TOKUNAGA, TOSHIO KIMURA, JIRO KAWAMURA1983 Volume 31 Issue 11 Pages 3988-3993
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high-performance liquid chromatographic method for the determination of ergometrine maleate (EM) and methylergometrine maleate (MM) in pharmaceutical preparations was established. EM and MM were extracted with dichloromethane from injections and tablets in the presence of sodium chloride and amonia solution. After evaporation of the dichloromethane, the residue was dissolved in water. Then EM and MM were determined by high-performance liquid chromatography on a LiChrosorb RP-18 column using a mixture of acetonitrile and 50mM acetate buffer (pH 3.5) containing 1.5mM triethylamine. In comparing the analytical data obtained by this method with those by the colorimetric method, both data were in excellent agreement except in the case of MM tablets, which contained related compounds. EM in the solution prepared according to the content uniformity test for EM tablets in JP X was determined by both methods. The average values of the contents in 10 tablets were 96.0% by the colorimetric method and 80.8% by the HPLC method. The degradation of EM took place during shaking for the extraction of EM and could not be detected by the colorimetric method.View full abstractDownload PDF (610K) -
AKIHUMI MOCHIIKE, IKUNORI SAKAMOTO, NOBUHIKO HOSHITA1983 Volume 31 Issue 11 Pages 3994-4000
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix types of octadecachloroquaterphenyls (ODCQPs) were prepared by chlorination of the corresponding quaterphenyls (QPs), and the QP skeletons of polychlorinated quaterphenyls (PCQs) in the blood of "Yusho"patients were investigated. The results are as follows : (1) The six types of ODCQPs showed characteristic mass spectra. (2) PCQs in the blood of Yusho patients were found to be a mixture of six types of PCQ isomers by gas chromatography and mass spectrometry. (3) The ratios of six types of PCQ isomers in the Kanechlor 400 used as the thermotransfer medium and in the blood of Yusho patients were different.View full abstractDownload PDF (616K) -
HIROSHI HOSODA, HIROMITSU YOKOHAMA, KAZUO ISHII, YUKO ITO, TOSHIO NAMB ...1983 Volume 31 Issue 11 Pages 4001-4007
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of developing immunoassays of tetrahydro-11-deoxycortisol or its glucuronides, various haptenic derivatives were synthesized. The 3-hemisuccinate (15), 21-hemisuccinate (8), 3-hemiglutarate (16), 21-hemiglutarate (9) and glucuronides (19, 23, 25) of tetrahydro-11-deoxycortisol were prepared starting from 11-deoxycortisol 21-acetate (1). Then, antisera were elicited in two rabbits by immunization with the conjugate of tetrahydro-11-deoxycortisol 3-glucuronide (19) with bovine serum albumin. It was found that the antisera had binding affinities to enzyme-labeled antigens prepared from 15, 16 and 19 ; the binding was inhibited by the glucuronide (19) in the enzyme immunoassay procedure.View full abstractDownload PDF (832K) -
SHIGERU YOSHIDA, KAYOKO ODA, SHINGO HIROSE, TATSUMORI TAKEDA1983 Volume 31 Issue 11 Pages 4008-4015
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe describe a new flow injection system with a stream-switching valve for continuous monitoring of the isoenzyme activities of creatine phosphokinase (EC 2.7.3.2) after liquid chromatographic separation. Serum, injected into a mini-column (15mm×2mm) of DEAE-Sepharose, was eluted stepwise with Tris-buffered sodium chloride (30, 145 and 300mM). The separated isoenzymes were subsequently mixed with the enzyme reagents and immediately passed to the fluorescence detector to measure serum background before the beginning of the enzyme reactions. After the first measurement of background fluorescence, the mixture, which was passed to the delay coil by the stream-switching valve, underwent a series of enzyme reactions, ultimately resulting in the formation of fluorescent nicotinamide adenine dinucleotide, reduced form (NADH). The fluorescence intensity of NADH was measured again with the same detector. Isoenzyme activity was determined by subtracting the area of serum background from the area of fluorescent NADH. A major advantage of this detection system is the ability to carry out continuous monitoring of the isoenzyme activities with removal of the serum background. Fluorometric detection of the separated isoenzymes permits sensitive and unambiguous detection of three isoenzymes.View full abstractDownload PDF (780K) -
YOSHIKAZU FUJITA, ITSUO MORI, SHOKO KITANO1983 Volume 31 Issue 11 Pages 4016-4021
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple and rapid spectrophotometric method for the determination of minocycline was established using zirconium (IV), o-hydroxyhydroquinonephthalein and fluoride ions in the presence of sodium dodecyl sulfate. This method could be used to determine 5-40μg/10ml of minocycline ; the Sandell sensitivity was estimated to be 0.0067μg/cm2 at 515nm. This method was applied to the determination of minocycline hydrochloride in pharmaceutical preparations, and the recovery of minocycline added to human urine was studied.View full abstractDownload PDF (552K) -
TOSHIO OKANO, SONOKO MASUDA, MASAKO ISHIMINE, JUNKO MURAI, YUKAKO YAMA ...1983 Volume 31 Issue 11 Pages 4022-4028
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 25-hydroxyvitamin D3 [25 (OH)D3] binding proteins from rat lymph and plasma were isolated and purified by sequential use of gel filtration, affinity and ion exchange chromatographies. The properties of both proteins were examined by high-performance liquid chromatography [HPLC], electrophoretic and immunological methods. The results were as follows. (1) On HPLC analysis using a gel permeation column, the proteins showed the same retention times. (2) On disc and sodium dodecyl sulfate disc gel electrophoresis, they showed the same isoelectric points. (4) On immunoelectrophoresis against rat whole antiserum obtained from rabbit, they showed immunological identity. These results strongly suggest that the 25 (OH)D3 binding proteins from rat lymph and plasma are the same protein.View full abstractDownload PDF (911K) -
YOSHINOBU FUKUMORI, TOMOAKI FUKUDA, YUKO YAMAMOTO, YASUE SHIGITANI, YO ...1983 Volume 31 Issue 11 Pages 4029-4039
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree erythromycin solids were characterized. In differential scanning calorimetry (DSC), the anhydrate exhibited only a melting endotherm at 193°C. The dihydrate was desolvated at temperatures between 59 and 105°C and liquefied at 124-130°C. The dehydration product remained crystalline up to 124°C (polarizing microscopic observation). When the dihydrate was heated at 135°C and cooled to room temperature, an amorphous solid having a glass transition temperature of 106°C was produced. The monohydrate reported by Allen et al. was found in this study to be a desolvation product of the chloroform solvate. The aqueous solubilities for the dihydrate and the anhydrate were determined by a conventional method, while that for the amorphous solid was estimated by measuring the dissolution rate by means of a rotating disk method. The temperature dependence of solubility for each form was such that the solubility increased with decrease in temperature. The heats of solution increased with temperature and the plots against temperature for the three forms could be fitted to a straight line. The slope of the plot appeared to be identical among the three forms. This result suggested that the above peculiar temperature dependence of solubility might result from some intermolecular interaction in the aqueous solution.View full abstractDownload PDF (1032K) -
YASUJI TAKASHIMA, SHIGEO TANAKA, HIROSHI YOSHIZAWA1983 Volume 31 Issue 11 Pages 4040-4047
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe distribution of fluocinolone acetonide (FA) in various creams and the release rate of FA from these creams were examined and the results were compared with the observed human vasoconstrictor activity of these creams. The creams were prepared by using various concentrations of surfactants and FA. The distribution of FA in the creams was examined by ultracentrifugation and ultrafiltration methods. The partition coefficients to the oil phase and surfactant phase were also measured. Then, the distribution of FA in the cream was calculated theoretically and these values were compared with the experimental data. From the results for creams containing various concentrations of FA, the distribution of FA in cream is considered to depend simply on a distribution law. As the amount of polysorbate 80 in the cream was increased, the FA release rate and vasoconstrictor activity decreased. The reason was considered to be that FA was trapped in the surfactant phase, and so the free FA concentration in the aqueous phase decreased. In order to enhance the efficacy of the drug, therefore, it is necessary to select correct amounts and kinds of surfactants and to increase the free FA concentration in the aqueous phase.View full abstractDownload PDF (673K) -
SHOJI FUKUSHIMA, KAZUHIKO JUNI, MASAHIRO NAKANO1983 Volume 31 Issue 11 Pages 4048-4056
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWater-in-oil-in-water (W/O/W) type double emulsions were prepared by two-step emulsification procedures. The structures of W/O/W type double emulsions and the release characteristics of cytarabine and 5-fluorouracil (5-FU) from W/O/W type double emulsions were studied. W/O/W type double emulsions were ruptured within 24h when sorbitan monooleate (SO-10) or sorbitan sesquioleate (SO-15) was used as a lipophilic emulsifier. On the other hand, W/O/W type double emulsions prepared in a hydrogenated castor oil (HCO-10) in peanut oil were still intact after 24h. Therefore, the release characteristics of drugs were studied in HCO-10 in peanut oil. The release of cytarabine from W/O/W type double emulsions was very prolonged. The release of cytarabine was enhanced with increase in the volume of inner aqueous phase or increase in the concentration of HCO-10. The concentration of cytarabine and the concentration of a hydrophilic emulsifier (HCO-60), however, had little effect on the release of cytarabine. Whereas the release of 5-FU from W/O/W type double emulsions was as fast as from a simple solution, the release was very prolonged when the pH value of the inner aqueous phase was adjusted to 10.0. These results show the utility of W/O/W type double emulsions for sustained release preparations and raise the possibility of control of drug release from W/O/W type double emulsions.View full abstractDownload PDF (1448K) -
AKIRA TSUJI, EMI NAKASHIMA, KAZUNORI NISHIDE, YOSHIHARU DEGUCHI, SHOIC ...1983 Volume 31 Issue 11 Pages 4057-4069
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA quantitative study on the pH-dependency of the degradation, solubility, and dissolution of fatrizine and cefadroxil was carried out at 35 or 37°C, and at an ionic strength of 0.5. The gradation rates of cefatrizine were determined by high-performance liquid chromatography. At constant pH and temperature, the degradation followed pseudo first-order kinetics. The shape of the rate constant-pH profile resembled those for cefadroxil and other aminocephalosporins. In and acidic medium below pH 4, cefatrizine was reasonably stable with a half-life of 14d at 35°C. At neutral pH, cefatrizine was degraded with a half-life of about 6h at 35°C via intramolecular reaction by the nucleophilic attack of the α-amino group on the β-lactam moiety. The intramolecular reaction rate was very similar to that of cephaloglycin, but ten times faster than those for cefadroxil, cephalexin, and cefradine under the same conditions. Both aminocephalosporins exhibited similar U-shaped solubility curves against pH. Their minimum solubilities were 4.6×10-2M, close to that of cephalexin monohydrate. The dissolution rate constants from a rotating disk were determined and interpreted successfully in terms of the dissociation equilibrium reaction and the diffusion kinetic model. Temperature effects on the degradation rate, solubility, and the dissolution rate were also examined.View full abstractDownload PDF (1139K) -
HIROSHI YOSHIKAWA, KANJI TAKADA, SHOZO MURANISHI1983 Volume 31 Issue 11 Pages 4070-4076
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe requirement of complex formation for the selective transfer of bleomycin from the large intestine of rat by a bifunctional delivery system was investigated. The delivery system developed by us is a combination of macromolecular dextran sulfate, mean molecular weight (MW), 500000, as a lymphotropic carrier forming an ionic complex with bleomycin, and lipid-surfactant mixed micelles as an absorption promoter. Co-existence of the bifunctional delivery system (bleomycin dextran sulfate complex+mixed micelles) with saline resulted in the dissociation of the complex. Administration of this system with saline into the lumen of the large intestine showed no selective rise of lymph level of bleomycin compared with the blood level, and pretreatment with dextran sulfate into the lumen did not increase the lymphatic transfer of bleomycin. Lower molecular weight dextran sulfate (MW, 5000) formed a complex with bleomycin, like macromolecular dextran sulfate (MW, 500000). However, administration of this complex with mixed micelles failed to selectively enhance the lymphatic transfer of bleomycin. Co-administration of bleomycin with other macromolecules (dextran or diethylaminoethyl dextran, MW, 500000) that do not form a complex with bleomycin also failed to selectively increase the lymphatic transfer of bleomycin. These findings suggest that the complex formation of bleomycin with a macromolecule over a certain molecular weight is required for the selective transfer of bleomycin into the lymphatics from the large intestine by a bifunctional delivery system.View full abstractDownload PDF (715K) -
JUN IMAI, MASAHIRO HAYASHI, SHOJI AWAZU, MANABU HANANO1983 Volume 31 Issue 11 Pages 4077-4082
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe solubilization dl-α-tocopherol (VE) into micellar solutions of bile components and non-ionic polysorbate 80 (PS-80) was studied. Dihydroxy conjugated bile salt showed a higher saturation ratio than trihydroxy conjugated bile salt. The mixed micelles of bile salt with egg lecithin (PC) solubilized more VE than the bile salt alone. PS-80 micelles showed a saturation ratio approximately 20 times higher than those of bile salts. When PC was included in PS-80micellar solution, the solubility of VE decreased with increasing PC content. The order of micellar size of bile salts and PS-80 solubilizing VE, as measured by gel filtration, was sodium taurocholate, sodium taurodeoxycholate and PS-80.View full abstractDownload PDF (579K) -
HITOSHI SASAKI, MARI FUKUMOTO, MITSURU HASHIDA, TOSHIKIRO KIMURA, HITO ...1983 Volume 31 Issue 11 Pages 4083-4090
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive alkoxycarbonyl derivatives of mitomycin C possessing various lipophilic pro-moieties including benzyloxycarbonyl, propyloxycarbonyl, pentyloxycarbonyl, nonyloxycarbonyl, and cholesteryloxycarbonyl groups were synthesized and their physicochemical and biological characteristics were examined. All compounds showed increases of octanol/water partition coefficients, lipophilic indexes (k'o) in HPLC, and lipid solubilities to various degrees depending on their pro-moiety structure. They showed only slight antimicrobial activities against Escherichia coli B, but all the compounds except for cholesteryloxycarbonyl mitomycin C showed significant activity in vivo against a L1210 leukemia system at a relatively low dose range. These derivatives showed enzyme-mediated conversion to the parent compound in rat plasma and liver homogenate, while they were chemically stable in neutral aqueous media. Essentially no bioactivation was observed for cholesteryloxycarbonyl mitomycin C. Species differences were observed in these bioactivation phenomena. These results suggested the potential utility of the derivatives as lipophilic prodrugs.View full abstractDownload PDF (789K) -
YUJI TANAKA, TSUNETOMO TAKEI1983 Volume 31 Issue 11 Pages 4091-4099
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLung surfactants were extracted either by lavage or by mincing method from lungs of calves, oxen, dogs and rabbits, and were purified in parallel. These lung surfactants were modified by adding some components in which they were apparently deficient ; the contents of disaturated phosphatidylcholine, fatty acids and triacylglycerols were adjusted to 47, 7 and 7%, respectively. The native and modified lung surfactants were examined with respect to their surface properties in vitro and their lung pressure-volume characteristics in vivo. No obvious differences were found in the chemical components of the lung surfactants from different mammalian species and of those prepared by the different extraction methods. Although there were no distinct differences in the phosphatidylcholine contents of the lung surfactants among the mammalian species, the content in the samples obtained by the lavage method was slightly higher than that in samples obtained by the mincing method. Although all the native lung surfactants spread spontaneously and were rapidly adsorbed, they did not show good surface activities in vitro or good lung pressure-volume characteristics in vivo. In contrast, all the modified lung surfactants showed good surface properties in vitro and also gave normal lung pressure-volume characteristics to premature rabbit fetuses in vivo irrespective of the mammalian species from which the native surfactants had been derived or of the extraction method used.View full abstractDownload PDF (932K) -
YUJI TANAKA, TSUNETOMO TAKEI, YOSAKU KANAZAWA1983 Volume 31 Issue 11 Pages 4100-4109
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe relations between the kinds of fatty acids and triacylglycerols present and the properties of lung surfactants were examined with modified lung surfactants. Palmitic acid-tripalmitoylglycerol, stearic acid-tristearoylglycerol and mixtures of fatty acids-triacylglycerols gave good surface activities with the lung surfactant, but oleic acid-trioleoylglycerol did not give good surface activity in vitro. Lung surfactants modified with palmitic acid-tripalmitoylglycerol, stearic acid-tristearoylglycerols and the mixtures restored the initial lung pressure-volume characteristics to the excised lung after these characteristics had been lost as a result of lavage in situ. Fatty acids gave better surface activities with the lung surfactant than triacylgycerols. The lung surfactants modified with palmitic acid, stearic acid and a mixture of fatty acids showed better surface activities in vitro and gave better lung pressure-volume characteristics in situ than those with oleic acid and triacylglycerols. The protein contained in the bovine lung surfactant was a lipoprotein in which the molar ratio of phopsholipids to protein was about 100 : 1. The molecular weight of the protein was 35000 and was reduced to 10000 by pretreatment with 2-mercaptoethanol after the removal of the phospholipids from the lipoprotein. This protein contained a large proportion of nonpolar amino acids. The lipoprotein showed spontaneous spreading with 1, 2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and with mixtures of DPPC and palmitic acid or tripalmitoylglycerol. The lipoprotein also enlarged the areas of the hysteresis loops of DPPC and the mixtures.View full abstractDownload PDF (940K) -
YUJI TANAKA, TSUNETOMO TAKEI, KAZUO MASUDA1983 Volume 31 Issue 11 Pages 4110-4115
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCorrelations between surface activities in vitro and lung pressure-volume characteristics in situ or in vivo were examined with modified lung surfactants. Correlations were found between the value of the minimum surface tension and lung pressure-volume characteristics in situ or in vivo. The surface tension in compression at 60% surface area was also correlated with the lung pressure-volume characteristics in situ and in vivo. Correlations between chemical components in the lung surfactant and its activities in vitro, in situ and in vivo were also examined. The content of disaturated phosphatidylcholine was correlated to the value of the minimum surface tension, the spreading rate and pressure-volume characteristics in situ and in vivo. These results showed that the following in vitro criteria are essential for a lung surfactant to give normal pressure-volume characteristics to the mammalian lung in situ and in vivo ; 1) a minimum surface tension of 10 dyn/cm or less, 2) a surface tension of 13 dyn/cm or less in compression at 60% surface area, 3) spontaneous spreading. Furthermore, we found that the content of disaturated phosphatidylcholine in the lung surfactant is an important determinant in relation to the above criteria.View full abstractDownload PDF (627K) -
KUNIO SEKI, TAKEHIKO YAMASHITA, JUNICHI ISEGAWA, MINORU FUKUDA, HIROSH ...1983 Volume 31 Issue 11 Pages 4116-4126
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of nicotinic acid-ethanolamine derivatives was synthesized and evaluated pharmacologically and biochemically in mice and rats. Many compounds showed considerable hypolipidemic activity in two models : hypercholesterolemic mice and hypertriglyceridemic rats. The results clarified some structure-activity relationships ; there was an increase in efficacy resulting from the introduction of alkyl or aryl groups on the nitrogen of the ethanolamine part. Furthermore, it was clearly shown that coupling of ethanolamines with nicotinic acid (NA) resulted in a marked decrease in toxicity. Among the compounds tested, 2-(N-isopropyl-N-nicotinoylamino) ethyl nicotinate (20) was found to possess more favorable pharmacological and toxicological profiles than NA. Studies on 20 indicated that its hypolipidemic effect might be attributable to NA released by hydrolysis in vivo of the ester linkage. After administration of 20, the maximum serum level of free NA was approximately 4 times lower and the persistence of NA level in the serum was longer than that of the NA-treated group.View full abstractDownload PDF (852K) -
MASARU KOBAYASHI, HIROSHI MITSUHASHI1983 Volume 31 Issue 11 Pages 4127-4129
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(24S)-24-Methyl-5α-cholestane-3β, 5, 6β, 25ζ, 26-pentol (1) was isolated from the soft coral Sarcophyton glaucum. The structure of 1 was confirmed by the spectroscopic data and by the synthesis of a C-25 isomeric mixture of 1 starting from codisterol acetate (5a), which is one of the main components in the 3β-monohydroxysterol fraction of S. glaucum.View full abstractDownload PDF (454K) -
TOKUO ITOH, TOYOAKI ISHIKURA, YOSHIHISA MIZUNO1983 Volume 31 Issue 11 Pages 4130-4134
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was shown that the remarkable discrepancy among reported proton nuclear magnetic resonance (1H NMR) spectra of 3-deazaadenosine obtained under comparable conditions is actually a reflection of a difference in molecular species, one being neutral and another being cationic, by carefully measuring the 1H NMR spectra of 3-deazaadenosine and its hydrochloride as well as 3-deazaadenine derivatives, whose preparation is also described.View full abstractDownload PDF (524K) -
TAKESHI IMANISHI, MAKOTO INOUE, MIYOJI HANAOKA1983 Volume 31 Issue 11 Pages 4135-4138
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compound (6) was prepared from ethyl 3-hydroxy-1, 2, 3, 6-tetrahydropyridine-1-carboxylate (2) via a regioselective hydroxylation at the C-4 position of the olefin (7) by utilizing an iodolactonization reaction.View full abstractDownload PDF (479K) -
HISAYUKI TANIZAWA, YASUYUKI SAZUKA, AKIKO KOMATSU, SHIZUO TODA, YOSHIO ...1983 Volume 31 Issue 11 Pages 4139-4143
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThough many methods are available for the efficacy testing of antioxidants, a satisfactory method has not been established yet, because the conventional methods require a long experimental time, considerable technical skill, or large and expensive apparatus. We have established a new method based on the air-oxidation of linoleic acid, one of the essential fatty acids, by air bubbling (2h incubation at 60°C with 500ml/min air flow rate). Good reproducibility and low variation were obtained by this method. Six tested antioxidants (ascorbic acid, ascorbyl stearate, butyl hydroxyanisole, dibutyl hydroxytoluene, propyl gallate, α-toco-pherol) inhibited the oxidation of linoleic acid proportionally to their added concentration. The relative efficacies of the six antioxidants were broadly in agreement with expection.View full abstractDownload PDF (501K) -
KAZUYO NISHIHARA, YUKINAO KOHDA, ZENZO TAMURA1983 Volume 31 Issue 11 Pages 4144-4146
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high-performance liquid chromatographic (HPLC) method for the determination of sultopride in serum and saliva was developed. The limit of detection of sultopride using 0.5ml sample volume was 0.04μg/ml in serum and saliva. The recoveries of sultopride added to serum and saliva (2μg/ml) were 99.6±3% and 99.8±3% (mean±S. D., n=5), respectively. The coefficients of variation of within-run assays for 3 levels of sultopride in serum were less than 4%. There was good agreement between the serum sultopride concentration determined by radioimmunoassay and that determined by HPLC (y=0.961x+0.008, r=0.995).View full abstractDownload PDF (360K) -
MUNETAKA NOKUBO, MIIKO TSUCHIYA1983 Volume 31 Issue 11 Pages 4147-4151
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe specific activity of hepatic microsomal 3-hydroxy-3-methylglutaryl coenzyme A reductase (HMG-CoA reductase) was examined at noon and at midnight in rats of both sexes pretreated with phenobarbital, spironolactone, or diazepam. In female rats, phenobarbital pretreatment significantly increased the activity of the enzyme at midnight, but the activity at noon remained unaltered. In male rats, the activity was unchanged by phenobarbital pretreatment both at noon and at midnight, while in castrated rats, the activity was increased significantly at midnight by pretreatment with phenobarbital. Spironolactone pretreatment decreased the activity at midnight but increased the activity at noon in both sexes. In adrenalectomized male rats, the activity in rats pretreated with spironolactone was unchanged both at noon and at midnight, compared with untreated adrenalectomized rats. Diazepam pretreatment increased the activity at noon and kept it unchanged at midnight in both sexes. It is suggested that the effect of these drugs on HMG-CoA reductase should be carefully examined in view of the variability of the effect between day and night as well as the sex-dependent differences in rats.View full abstractDownload PDF (540K) -
MASAHIDE YASUDA, YOSHIHIDE OKAMURA, MASAHIKO YOSHIKAWA, TOSHIYUKI TAKE ...1983 Volume 31 Issue 11 Pages 4152-4156
Published: November 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to determine the effects of diet containing three calcium (Ca) levels (none, 0.8 or 2.4%) on rats, the Ca, magnesium and phosphorus contents, fatty acid composition in tissues as well as their growth were examined. In the groups fed with Ca-free and 2.4% Ca diet the growth of rats was suppressed compared with that of a control group (0.8% Ca). In both groups the relative weight of brain with respect to the body weight increased and in the group fed with 2.4% Ca diet, the weight of kidney increased both relatively and absolutely. Ca content in all tissues except the kidney of female rats decreased to various extents in the group fed with Ca-free diet. In the group fed with 2.4% Ca diet, the Ca content increased markedly only in the kidney. In the group fed with 2.4% Ca diet, magnesium content decreased only in bone, and phosphorus content was not affected by any dietary Ca level. Fatty acid compositions of the heart, liver and kidney changed as dietary Ca levels were varied, but no change was observed in the brain. Namely, in the group fed with 2.4% Ca diet, oleic and eicosatrienoic acids increased, but linoleic and arachidonic acids decreased. On the other hand, consistent changes of composition in the Ca-free diet group were not observed in any individual tissue of either sex. From these results, it was concluded that the growth of rats was suppressed in the groups fed not only with Ca-free but also high Ca level diets and that the mineral content and fatty acid composition in various tissues changed as the dietary Ca level was varied.View full abstractDownload PDF (528K)