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Volume 29, Issue 8
Displaying 1-44 of 44 articles from this issue
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MASARU KIDO, KAZUYUKI NAKAGAWA, TAKAJI FUJIWARA, KENICHI TOMITA1981 Volume 29 Issue 8 Pages 2109-2115
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal structure of carteolol hydrochloride (C16H24N2O3·HCl), a novel β-adrenergic blocking agent, was determined by X-ray diffraction analysis. The crystal is monoclinic and the space group is P 21/n with Z=4. The cell dimensions are a=7.873 (4), b=26.435 (19), c=8.549 (7) A, and β=105.67 (6)°. The structure was solved by a direct method using the MULTAN program and refined by a block-diagonal least-squares method to give a final R-value of 0.054. Cl- anion forms two hydrogen bonds with the cationic amino group and one with the hydroxy group. The amino and hydroxy groups are relatively close together, but no intramolecular hydrogen bond is formed. The C (3)-C (4) bond distance of the 3, 4-dihydro-2-quinolone ring, 1.397 A, is rather shorter than a normal single bond distance but it seems probable that the bond is actually single and that the C (3) and C (4) atoms deviate from the least-squares ring plane by 0.42 A and 0.30 A, respectively, to opposite sides.View full abstractDownload PDF (647K) -
SABURO SHIMABAYASHI, CHIZUKO TAMURA, MASAYUKI NAKAGAKI1981 Volume 29 Issue 8 Pages 2116-2122
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe order of affinity of various metal ions for synthetic hydroxyapatite (HAP) in water was determined by measuring the sedimentation volume, mean particle diameter, suspension pH, and the amounts of metal chloride adsorbed and of cetylpyridinium chloride adsorbed on HAP in competition with metal ions. Direct chemical analysis of divalent alkaline earth cations showed that the binding affinity to HAP is in the order Ca2+>Ba2+>Mg2+, in accordance with that deduced from the other experimental results ; Ca2+ presumably has the highest affinity because it is the parent ion of HAP. By comparing the effects of mono-and divalent cations, it was concluded that the order of binding affinity of monovalent alkali metal cations is Na+>K+>Li+ ; Na+ presumably has the highest affinity because its crystal ion radius is almost the same as that of Ca2+. It was also shown that these ions bind electrostatically by at least two type of mechanism, ionexchange with Ca2+ on HAP and specific adsorption on HAP. It was assumed that the binding sites are Ca2+-defects or dislocations on HAP, and that adsorbate ions are dehydrated when they are adsorbed. Some properties of biological mineralization can be explained on the basis of the results presented here.View full abstractDownload PDF (762K) -
YOSHISUKE TSUDA, MIYUKI KANEDA, NAOMI YASUFUKU, YUKIKO SHIMIZU1981 Volume 29 Issue 8 Pages 2123-2134
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Lycopodium inundatum, Lycopodiaceae, seven new triterpenoid-glycosides (inundoside-A, -B, -D1, -D2, -E, -F, and -G) were isolated together with α-onocerin and serratenediol. Their structures were elucidated as serratenediol 3-α-L-arabinopyranoside (A), its 21-acetate (B), its 4'-O-p-coumaroyl ester (D1), its 21-O-acetyl and 4'-O-p-coumaroyl ester (D2), 21-episerratenediol 3-α-L-arabinopyranoside (E), and its 4'-O-p-coumaroyl ester (F) by chemical and spectroscopic means. The previously reported tohogenolglycoside (inundoside-C) thus must by tohogenol 3-α-L-arabinopyranoside. The other glycoside, inundoside-G, obtained only as a tetraacetate, is suggested to be serratenediol 3-α-L-arabinopyranoside 2'-or 3'-O-p-coumaroyl ester on the basis of spectroscopic evidence.View full abstractDownload PDF (1185K) -
MICHIHIRO YAMAMOTO, HISAO YAMAMOTO1981 Volume 29 Issue 8 Pages 2135-2156
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 5-chloro-2-trichloroacetamidobenzophenone (2a) with several primary alkylamines in DMSO gave high yields of 3-substituted 6-chloro-3, 4-dihydro-4-phenyl-4-trichloromethyl-2(1H)-quinazolinones 6, which were found to be formed by base-catalyzed and/or thermal cyclization and simultaneous rearrangement of the isomeric 5-chloro-2-trichloroacetamidobenzophenone alkylimines 5. Both compounds 5 and 6 were obtained when the reaction was effected in benzene. Treatment of the compound 2a with bulky amines such as isopropylamine and cyclohexylamine gave, under similar conditions, the corresponding benzophenone imines 5d and 5e exclusively, and these could be transformed into the quinazolinones 6d and 6e, respectively, on heating in pyridine or HMPT. The reaction of N-substituted trichloroacetamidobenzophenones 2m and 3n with N-(2-aminoethyl) morpholine as well as ammonia in DMSO yielded the 1-alkylaminobenzophenone imines 4m-o, which on treatment with trichloroacetyl chloride were readily cyclized to give the corresponding 1-substituted 4-trichloromethylquinazolinones 6m-o. The trichloromethyl group of the 1-unsubstituted quinazolinones 6 was easily displaced by a nucleophile such as hydride, alkoxide or hydroxide under base catalysis to give the 3, 4-dihydro-2 (1H)-quinazolinone derivative 9, 10 or 11 almost quantitatively, whereas the 1, 3-disubstituted quinazolinone 6o was not affected. The sodium borohydride reduction of the methylimine 5a at room temperature mainly afforded the trichloroacetamidobenzhydrylamine 8a, which underwent thermal cyclization to the quinazolinone 9a via split of chloroform. In contrast, the reaction of 5-chloro-2-trifluoroacetamidobenzophenone (2p) with some primary alkylamines in DMSO produced the trifluoroacetamidobenzophenone alkylimines 5p-r, which on treatment with sodium borohydride could be converted only to 3-substituted 6-chloro-3, 4-dihydro-4-phenyl-2-trifluoromethylquinazolines 15. These procedures were successfully utilized in syntheses of the imidazo [1, 2-c] quinazolinone 16, oxazolo [3, 2-c] quinazolinones 17t and 17v, and 1, 3-oxazino [3, 2-c] quinazolinone 17u.View full abstractDownload PDF (2176K) -
EIYU YO, KAZUYUKI NAKAGAWA, YO HOSHINO1981 Volume 29 Issue 8 Pages 2157-2160
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe optical isomers of 8-acetonlloxy-5-[3-(3, 4-dimethoxyphenethylamino)-2-hydroxypropoxy]-3, 4-dihydrocarbostyril were prepared from the optically active epichlorhydrin, and their β-adrenergic blocking activities were examined. The (S) (-)-isomer was shown to be about 200 times more potent on atrial and 100 times more potent on tracheal preparations, and was also about 3 times more β1-selective than the (R) (+)-isomer.View full abstractDownload PDF (517K) -
MICHIAKI TOMINAGA, EIYU YO, MASAAKI OSAKI, YOSHIAKI MANABE, KAZUYUKI N ...1981 Volume 29 Issue 8 Pages 2161-2165
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5, 8-Dihydroxy-3, 4-dihydrocarbostyril, a key intermediate for the synthesis of β1-selective 8-acetonyloxy-5-[3-(3, 4-dimethoxyphenethylamino)-2-hydroxypropoxy]-3, 4-dihydrocarbostyril hydrochloride (opc-1427) was prepared from 2, 5-dimethoxyaniline.View full abstractDownload PDF (584K) -
MICHIAKI TOMINAGA, HITOSHI TONE, KAZUYUKI NAKAGAWA, KAORUKO TAKADA, YO ...1981 Volume 29 Issue 8 Pages 2166-2181
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMany 5-(3-amino-2-hydroxypropoxy)-8-alkoxy and acyloxy-3, 4-dihydrocarbostyrils and 5-(3-amino-2-hydroxypropoxy)-8-alkoxycarbostyrils were synthesized from 5, 8-dihydroxy-3, 4-dihydrocarbostyril, and their β-adrenergic blocking activities were examincd. Among them, 8-acetonyloxy-5-[3-(3, 4-dimethoxyphenethylamino)-2-hydroxypropoxy]-3, 4-dihydrocarbostyril hydrochloride hydrate (IVh) was found to have potent β1-selective adrenergic blocking activity.View full abstractDownload PDF (1349K) -
KIMIYE BABA, MITSUGI KOZAWA, KIYOSHI HATA, TOSHIMASA ISHIDA, MASATOSHI ...1981 Volume 29 Issue 8 Pages 2182-2187
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo yellow pigments, I and II were isolated from the rhizomes of Cimicifuga dahurica MAXIM. (Ranunculaceae) and were elucidated as geometric isomers, (E)-3-(3'-methyl-2'-butenylidene)-2-indolinone and (Z)-3-(3'-methyl-2'-butenylidene)-2-indolinone, by chemical and spectral studies and by X-ray diffraction analysis, respectively. On standing, and ethanolic solution of II gave a colorless substance, which was regarded as a product of dimerization.View full abstractDownload PDF (629K) -
Studies on Nucleoside Analogs. XXI. : A Convenient Synthesis of 1, 2, 4-Triazole-5-thione GlycosidesHARUO OGURA, HIROSHI TAKAHASHI, OSAMU SATO1981 Volume 29 Issue 8 Pages 2188-2192
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of glycosyl isothiocyanates (1a-c) with acyl or aroyl hydrazine, followed by treatment with Ac2O-H3PO4, afforded 1, 2, 4-triazole-5-thione glycosides (20a, 21a-c, 22a) in fair yields. Attempts to prepare 1, 2, 4-triazole glycoside analogs with acetic anhydride or sodium methoxide failed. The reaction of glycosyl-2-(phenyl-or pyrid-2-ylhydrazine) thiocarboxamides (6a, 7a) with phosgene in pyridine or triethylamine gave thiadiazole-5-thiones (8a, 9a) instead of 1, 2, 4-triazole glycosides.View full abstractDownload PDF (634K) -
TETSUO MIYADERA, TADASHI HATA, CHIHIRO TAMURA, RYUJI TACHIKAWA1981 Volume 29 Issue 8 Pages 2193-2198
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxazolidone-fused benzodiazepine derivative (1) was prepared by treatment of chlordiazepoxide (2) with sodium hydride and ethyl chloroformate followed by the N-oxide rearrangement of the resultant carbamate (3) with acetic anhydride. The first reaction was found to be accompanied by a multi-step rearrangement of the initially formed 3 as a side reaction giving rise to the indolenine derivative (4). The structure of 4 was determined by X-ray crystallographic analysis.View full abstractDownload PDF (593K) -
SEIICHI UESUGI, HIROKO MIKI, MORIO IKEHARA1981 Volume 29 Issue 8 Pages 2199-2204
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS^<13>C nuclear magnetic resonance spectra of various 2'-substituted 2'-deoxyadenosines are presented. The relative substituent chemical shifts of each sugar carbon are analyzed in terms of a substituent electronegativity parameter and compared with the data for substituted cyclohexanes. The relative substituent chemical shifts of C2' and C4' are controlled mainly by the inductive effect of the substituent. Those of C1' and C3' cannot be interpreted by inductive effect only. Some effect which is perturbed by the presence of a cis-substituent seems to be operating. A good linear correlation was observed between the substituent chemical shift of C2' and the N conformer population in the furanose puckering equilibrium.View full abstractDownload PDF (666K) -
KATSUHIRO IMAKI, SHIGERU SAKUYAMA, TAKANORI OKADA, MASAAKI TODA, MASAK ...1981 Volume 29 Issue 8 Pages 2210-2214
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-[3-Mercaptoalkanoyl] pyroglutamic acids and 1-[3-mercaptoalkanoyl]-4-hetero (oxa, thia and aza) pyroglutamic acids were prepared and their inhibitory activities against angiotensin-converting enzyme (ACE) were examined. (2S)-1-[(2S)-3-Mercapto-2-methylpropanoyl] pyroglutamic acid 2 was found to be the most potent orally active inhibitor of ACE of rabbit lung among the derivatives synthesized in the present study and appeared to have great potential for use as an oral antihypertensive agent.View full abstractDownload PDF (635K) -
TSUNEHIKO FUKUDA, SHIGERU KOBAYASHI, HIDEFUMI YUKIMASA, ISUKE IMADA, M ...1981 Volume 29 Issue 8 Pages 2215-2221
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-(2, 3-Dimethoxy-5-methyl-1, 4-benzoquinon-6-yl) propanoic acid, 10-(2, 3-dimethoxy-5-methyl-1, 4-benzoquinon-6-yl) decanoic acid, 6-(2, 3, 5-trimethyl-1, 4-benzoquinon-6-yl)-hexanoic acid, 9-(2-methyl-1, 4-naphthoquinon-3-yl) nonanoic acid were coupled to Nacetyl-6-O-aminoacylmuramyl-α-aminoisobutyryl-D-isoglutamines by the active ester method. The aminoacyl residues used were Gly, β-Ala, L-Pro, L-Leu, D-Leu, Ahx and Aud. Most of the resulting derivatives showed more potent adjuvant activity than N-acetyl-muramyl-L-alanyl-D-isoglutamine, an active constituent of mycobacterial cell wall peptidoglycan, for the induction of delayed-type hypersensitivity. The strength of the activity was affected by the combination of quinonyl acids and linking amino acids, and the present study indicated that the incorporation of an ω-(2, 3-dimethoxy-5-methyl-1, 4-benzoquinon-6-yl) alkanoyl moiety through Leu was most favorable.View full abstractDownload PDF (745K) -
YOSHIMASA KOBAYASHI, TADAHIRO TAKEDA, YUKIO OGIHARA1981 Volume 29 Issue 8 Pages 2222-2229
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new triglycosides of oleanane-type triterpenes, rotundioside E (3) and F (1), isolated from the leaves of Bupleurum rotundifolium L. were identified as 16α, 28-dihydroxyoleana-11, 13 (18)-dien-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (3) and 13β, 28-epoxy-16α-hydroxyoleana-11-en-3β-yl α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-β-D-fucopyranoside (1), respectively, on the basis of chemical and spectroscopic evidence.View full abstractDownload PDF (831K) -
YOSHIMASA KOBAYASHI, YUKIO OGIHARA1981 Volume 29 Issue 8 Pages 2230-2236
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new triterpenoids, rotundiogenin C (7), and rotundiogenin F (14), isolated from the leaves of Bupleurum rotundifolium L. (Umbelliferae), were identified as oleana-11, 13-(18)-diene-3β, 16α, 21α, 28-tetraol, and oleana-9, 12-diene-3β, 16α, 21α, 28-tetraol, respectively, on the basis of spectroscopic evidence and chemical correlations.View full abstractDownload PDF (772K) -
HIROAKI SAWAI, MASAJI OHNO1981 Volume 29 Issue 8 Pages 2237-2245
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOligouridylates up to the pentamer were obtained by the polymerization of uridine-5'-phosphorimidazolide in aqueous solution using Pb2+ ion catalyst. The resulting oligouridylates were fully characterized by sequential enzyme and alkaline digestions. The internucleotide linkages of the oligomers were mainly 2'-5'. The yields of the 2'-5'linked dimer, trimer, tetramer and pentamer were 14.2, 6.0, 2.0 and 0.4%, respectively.View full abstractDownload PDF (748K) -
YASUMASA HAMADA, NOBUHARU KATO, YUKO KAKAMU, TAKAYUKI SHIOIRI1981 Volume 29 Issue 8 Pages 2246-2250
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe use of easily recoverable tri-n-butylphosphoniummethylated polystyrene resin (phosphonium resin catalyst) under triphasic reaction conditions was proposed in Williamson's alkyl aryl ether synthesis. O-Methylation of 2-tert-butyl-5-methylphenol with methyl chloride was easily carried out in the presence of the phosphonium resin catalyst under basic conditions to give 2-tert-butyl-5-methylphenyl methyl ether in excellent yield. A few other phenols were also O-alkylated under similar triphasic reaction conditions to give alkyl aryl ethers.View full abstractDownload PDF (632K) -
JUNICHI KUNITOMO, MEGUMI OSHIKATA, YOSHIKO MURAKAMI1981 Volume 29 Issue 8 Pages 2251-2253
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of two unknown alkaloids (tentatively named Base A and Base D in a previous paper) from Stephania sasakii HAYATA (Menispermaceae) were established as 4-hydroxycrebanine (1), a new 4-hydroxyaporphine alkaloid, and (R)-roemeroline (3), respectively.View full abstractDownload PDF (472K) -
YUTAKA HIRANO, NOBUO IKEKAWA, YOKO TANAKA, HECTOR F. DELUCA1981 Volume 29 Issue 8 Pages 2254-2260
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBisnorcholenal 3-tetrahydropyranyl ether (1), obtained from bisnorcholenic acid in 3 steps, was coupled with lithium acetylide derived from 2-methyl-3-butyn-2-ol tetrahydropyranyl ether to give in 74% yield a 1 : 1 mixture of the cholest-5-ene-3β, 22, 25-trihydroxy-23-yne 3, 25-bis (tetrahydropyranyl) ethers, 2a and 2b. After resolution of the C-22 epimers and determination of their conflgurations, both isomers were converted to 22, 25-dihydroxycholesterol 3, 22-diacetates, 5a and 5b, and to 25-hydroxy-22-methoxycholesterol 3-acetate, 8a and 8b. These compounds were converted to (22R)-and (22S)-22, 25-dihydroxyvitamin D3, 12a and 12b, and to 25-hydroxy-22-methoxyvitamin D3, 14a and 14b, through the corresponding cholest-5, 7-diene-3β, 22, 25-triol 3, 22-diacetates (9a and 9b) and cholest-5, 7-diene-22-methoxy-3β, 25-diol 3-acetates (10a and 10b). According to preliminary biological testes, 22, 25-(OH)2D3 and 22-CH3O-25-OH-D3 have neither vitamin D activity nor antivitamin D activity.View full abstractDownload PDF (843K) -
YOICHI NAKATANI, GUY OURISSON, JEANPAUL BECK1981 Volume 29 Issue 8 Pages 2261-2269
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour chlorophyll derivatives (pheophytins) were isolated from silkworm excreta by column and thin-layer chromatography and their structures were elucidated by spectroscopy. Among them, two substances, 132-hydroxy (132-R, S) pheophytin a and pheophytin b, have in vitro cytostatic activity against hepatoma tissue culture (HTC) cells. The methyl ester derivatives of pheophorbides showed cytotoxic effects towards the tumor cells under illumination. This can be explained by photodynamic destruction of HTC cells by singlet oxygen, as has already been shown in the case of hematoporphyrin. The observation that natural pheophytins have cytostatic effects even in the dark suggests that there is another biological mechanism for the action of these chlorophyll derivatives.View full abstractDownload PDF (812K) -
TSUKASA TAKAMURA, TAKU CHIBA, SETSUZO TEJIMA1981 Volume 29 Issue 8 Pages 2270-2276
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 1, 6-anhydro-2, 2', 3, 4'-tetra-O-benzyl-β-lactose (1, 1 mol eq.) with the acetylated oxazoline of N-acetyllactosamine (2, 5 mol eq.) gave the derivatives of 6'-Nacetyllactosaminyllactose (3, 24.5%) and lacto-N-neohexaose (8, 53.5%). The protecting groups of 3 and 8 were removed by means of the following series of reactions to provide the corresponding tetrasaccharide (7) and hexasaccharide (12), respectively : debenzylation followed by acetylation, acetolysis, and de-O-acetylation. 13C-nuclear magnetic resonance spectral data for the 1, 6-anhydro-β-derivatives of 7 and 12 are presented.View full abstractDownload PDF (787K) -
MASASHI TOMODA, NORIKO SHIMIZU, HIROMI SUZUKI, TOMOKO TAKASU1981 Volume 29 Issue 8 Pages 2277-2282
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA representative mucilage, named Althaea-mucilage OL, has been isolated from the leaves of Althaea officinalis L. The final Preparation was homogeneous as determined by ultracentrifugal analysis, cellulose acetate membrane electrophoresis, and gel chromatography. Its water solution gave an intrinsic viscosity value of 49.0. It was mainly composed of partially acetylated acidic polysaccharide, and its molecular weight was estimated to be about 1800000. The polysaccharide was composed of L-rhamnose : D-galacturonic acid : D-glucuronic acid in the molar ratio of 1.5 : 1.1 : 1.0. Analysis of component sugars, together with reduction and methylation, and partial degradation studies made it possible to deduce the structural features of the polysaccharide moiety in the mucilage.View full abstractDownload PDF (739K) -
TOSHIYUKI SAKANO, SACHIKO MASUDA, TAMEYUKI AMANO1981 Volume 29 Issue 8 Pages 2283-2289
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFluorescamine derivatives of butylamine, benzylamine, p-anisidine, p-toluidine, aniline, p-chloroaniline, sulfanilamide, sulfamethoxazole and N1-acetylsulfamethoxazole were isolated and various characteristics of the fluorophoric derivatives were investigated, i.e., the effects of solvents, substituent groups, and pH, as well as hydrogen bonding in organic solvents, conversion to non-fluorescent lactones, and thin-layer chromatography behavior.View full abstractDownload PDF (678K) -
TOSHIYUKI SAKANO, SACHIKO MASUDA, TAMEYUKI AMANO1981 Volume 29 Issue 8 Pages 2290-2295
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA high-performance liquid chromatographic method for the determination of diaveridine (Dv) and sulfaquinoxaline (Sq) in hen's egg, chicken plasma, liver, kidney, heart, spleen, muscle, gizzard, skin and fat was developed using a C18 reversed-phase column and simple mobile phases. The pretreatments of Dv and Sq in such biological materials were classified into six groups. Detection limits were 0.02-0.04 ppm for Dv and 0.01-0.03 ppm for Sq. Average recoveries of Dv and Sq from egg and plasma were above 77%, and those from all other tissues ranged from 53 to 78%. The method was applied for residue analysis of Dv and Sq in egg yolk and albumen.View full abstractDownload PDF (643K) -
YASUMASA KIDO, ZENZO TAMURA1981 Volume 29 Issue 8 Pages 2296-2302
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn improved method for the Millon reaction using cupric ion together with mercuric ion is presented for the determination of tyrosine. Blue-violet coloration in the present method is based on the mercuration and nitrosation of tyrosine, according to the conventional Millon reaction, followed by the chelate formation of nitrosotyrosine with cupric ion. This method is more sensitive than the conventional reaction, and the colored substance is more stable than that formed by the conventional reaction, and the colored substance is more stable than that formed by the conventional method. The colored substance was identified as bis (4-methyl-2-nitrosophenolato) copper (II) by isolating it from the reaction mixture of 2-chloromercrui-4-methylphenol (an intermediate of the conventional Millon reaction of p-cresol), hydrogen nitrite and cupric ion. Millon-positive substances in urine were successfully determined by the present method by pretreating the sample with mercuric acetate.View full abstractDownload PDF (668K) -
TAKAYASU KITAGAWA, KUMIKO IWAKURA, EIZO HIRAI1981 Volume 29 Issue 8 Pages 2303-2307
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA fluorometric method for the determination of isouron (1) was established by modifying Dombrowski's method. Isouron was hydrolyzed to 3-amino-5-tert-butylisoxazole (2) followed by diazo coupling with 2, 6-diaminopyridine (DAP), and the resulting azo derivative (3) was oxidized to a fluorescent triazole (4). A simple nitrosation method was developed in order to overcome the interference by the strongly fluorescent reagent DAP. The oxidation yield of 3 to 4 was improved by employing the neutral condition. A linear relationship between the fluorescence intensity and isouron concentration was obtained in the range of 0.1-0.4 μg/ml. Isouron could be determined with a coefficient of variation of 2-3% (ten determinations), overall recovery of 85-90%, and quantitation limit of 40 ng/ml.View full abstractDownload PDF (572K) -
YOSHIYUKI KIMURA, MICHINORI KUBO, TADATO TANI, SHIGERU ARICHI, HIROJI ...1981 Volume 29 Issue 8 Pages 2308-2312
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of Scutellariae Radix ("Ogon"in Japanese) and its flavone components on lipid metabolism in the rat were investigated. Wogonin inhibited deposition of liver triglyceride and increased serum HDL-cholesterol level in rats fed on corn oil-cholestcrolsodium cholate mixture. Skullcapflavone II reduced the serum total cholesterol level and liver triglyceride content, and increased serum HDL-cholesterol. Baicalein and baicalin reduced the serum free fatty acid and triglyceride levels and liver triglyceride content. In addition to the in vivo experiments, the effects of flavone components of Ogon on lipid metabolism in fat cells isolated from epididymal adipose tissue of rats were examined. Wogonin and baicalein selectively inhibited adrenaline-induced lipolysis, and baicalein and baicalin selectively activated ACTH-induced lipolysis in fat cells. Skullcapflavone II inhibited adrenaline-and ACTH-induced lipolysis and lipogenesis from glucose in fat cells.View full abstractDownload PDF (584K) -
YOSHIHIRO SATO, TAIKO ODA, HAZIME SAITO1981 Volume 29 Issue 8 Pages 2313-2321
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo elueidate the stereochemical course of the microbial transformation of (+)-dehydrogriseofulvin (DGF) by Streptomyces species, (+)-[5'-2H] DGF, which was obtained by dehydrogenation of (+)-[5'α, 5'β-2H] epigriseofulvin, was incubated with S. cinereo-crocatus. The structure of the product was identified as (+)-[5'α-2H] griseofulvin (GF) by 2H nuclear magnetic resonance spectroscopy. The results of incubations of (-)-and (+)-DGF with eight Streptomyces species (S. cinereocrocatus, S. roseochromogenus, S. bikiniensis, S. griseinus, S. durhamensis, S. californicus, S. fimbriatus, and S. cinereoruber) showed that (-)-and (+)-DGF were isomerized to each other and converted to (+)-GF as the main product, although some (-)-GF was also formed depending on the microorganisms used. In particular, incubation of (+)-DGF with S. cinereoruber yielded (-)-GF as the main product. In addition, (±)-DGF was transformed by S. cinereocrocatus to the naturally occurring (+)-GF in 48% yield. The enantiomer ratios of DGF and GF obtained by microbial transformation were calculated from the [α]D values of corresponding enantiomer mixtures.View full abstractDownload PDF (1049K) -
TAKASHI ABIKO, IKUKO ONODERA, HIROSHI SEKINO1981 Volume 29 Issue 8 Pages 2322-2329
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn octadecapeptide, H-Arg-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-Gln-Thr-Leu-Thr-Ala-Val-Lys-Arg-OH, corresponding to the C-terminal portion of thymopoietin II was synthesized using protecting groups removable by hydrogen fluoride treatment. The in vitro addition of the synthetic octadecapeptide was able to restore the low E-rosette forming capacity of cells in a rheumatoid arthritis patient to normal levels. The in vitro effects of pentapeptide (positions 32-36), nonapeptide (positions 33-41) and decapeptide (positions 32-41) fragments of thymopoietin on the low E-rosette forming capacity of cells of a rheumatoid arthritis patient were also compared with that of the synthetic octadecapeptide. The relative potency of the pentapeptide was 10.56 and that of the decapeptide was 25.43 based on the octadecapeptide (100.00) as a standard, but the nonapeptide was ineffective.View full abstractDownload PDF (901K) -
TOSHIO INAGI, TOYOJIRO MURAMATSU, HIDETAKA NAGAI, HIROSHI TERADA1981 Volume 29 Issue 8 Pages 2330-2337
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo examine the fundamental process of the transfer of indomethacin (LND) to the biological membrane, the partition coefficient between n-octanol and water was measured at various pH values or in the presence of various cations by the shaking-flask method at 25°C. The apparent partition coefficient decreased with increase in pH and the true partition coefficient of unionized IND was determined to be 1.20×104, while that of ionized IND was 1.72×10-1. The IND anion was found to be readily transferred to the hydrophobic region by forming ion-pair complexes with cations in the aqueous phase. The ion-pair complex of IND with the ammonium ion was transferred to the organic phase more readily than that with the sodium or potassiumion. In this study, a method for quantitative analysis of the ion-pair partition of an unstable drug at alkaline pH was established under conditions where more than two cationic species were present.View full abstractDownload PDF (693K) -
KATSUHIKO SHIMA, CHIKAKO MATSUSAKA, MASAKO HIROSE, TETSUO NOGUCHI, TAK ...1981 Volume 29 Issue 8 Pages 2338-2344
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe characteristics of insomethacin (ID) gel ointment were compared with those of conventional types of ointments. 1) The percutaneous abserption of ID from a 50% alcoholic solution occurred by a simple diffusion process, sincc the percentage of absorbed ID did not depend on the concentration of ID. 2) The in vitro release of ID from the gel ointment was greater than that from conventional ointments. 3) The gel ointment had greater volatility and the concentration of ID in the gel base doubled in 4 hours under the conditions of 75% relative humidity at 25°C. 4) Reflecting the results of in vitro studies, the absorption of ID from the gelointment into rat skin and muscle was greater than that from conventional types of ointments. 5) From the time course of muscle ID levels, little lag time of ID transfer through the skin was apparent.View full abstractDownload PDF (655K) -
YUKIHISA KURONO, NAOKO OHTA, TOSHIHISA YOTSUYANAGI, KEN IKEDA1981 Volume 29 Issue 8 Pages 2345-2350
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactivities of the two esterase-like active sites on human serum albumin (HSA) towards p-nitrophenyl acetate (NPA) were evaluated in pH 7.4 phosphate buffer (μ=0.2) and at 25°C. Clofibric acid (CA) was used to distinguish between the two sites, the primarily reactive site (R site) being inhibited by CA and the secondarily reactive site (T site) not. The kinetic parameters for the two sites were determined. The dissociation constant between CA and the R site of HSA determined kinetically was consistent with the reciprocal of the binding constant obtained from the equilibrium dialysis experiment. The contribution of the T site to the sverall activities of HSA was estimated from the specificity constants (the ratio of the catalytic rate constant to the dissociation constant) and was 11.1%.View full abstractDownload PDF (610K) -
TSUTAO KURECHI, KIYOMI KIKUGAWA, SHUJI AOSHIMA1981 Volume 29 Issue 8 Pages 2351-2358
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSesamol (I) was transformed into a fluorescent product (II) and a violet-colored product (IV) by mild oxidation with hydrogen peroxide catalyzed by horseradish peroxidase. The product (II) was elucidated to be 2, 2'-dihydroxy-4, 5 ; 4', 5'-bis (methylenedioxy) biphenyl and the structure of IV was assumed to be the highly conjugated quinoid form of II. The product (II) was transformed into IV by hydrogen peroxide-peroxidase treatment and was regenerated from IV by treatment with reductants. Systems containing II, hydrogen peroxide and peroxidase may provide a new, versatile chromogenic determination method for hydrogen peroxide or peroxidase. Determination of hydrogen peroxide at around 10 μM and peroxidase at around 0.1 nM was possible. Oxidations of I by other means were performed and the results were compared with those obtained with hydrogen peroxide-peroxidase.View full abstractDownload PDF (888K) -
HITOSHI UNO, MIKIO KUROKAWA, YOSHINOBU MASUDA1981 Volume 29 Issue 8 Pages 2359-2361
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome 2-sulfamoylmethylbenzoxazole derivatives were synthesized from 2-bromomethylbenzoxazole by reaction with sodium bisulfite, followd by chlorination and amination. Among them, 2-sulfamoylmethylbenzoxazole (5a) showed the strongest anticonvulsant activity, which was compared with that of 3-sulfamoylmethyl-1, 2-benzisoxazole (I).View full abstractDownload PDF (423K) -
TETSUZO KATO, NOBUYA KATAGIRI, RENZO SATO1981 Volume 29 Issue 8 Pages 2361-2366
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Ethoxycarbonyl-5-oxo-4-oxaspiro [2.3] hexane (3), on treatment with sodio methyl acetoacetate in THF, was transformed into 3-hydroxy-4-ethoxycarbonyl-2-cyclopenten-1-one (5) in 82% yield. Reaction of compound 3 with malononitrile (4a) in the presence of sodium hydride in THF gave the cyclopentenone 5 and 2-amino-3-cyano-6-ethoxycarbonylethyl-4-pyrone (6) in 49% and 24% yields, respectively. Similarly, reaction of compound 3 with ethyl cyanoacetate (4b) afforded compound 5 and 2-amino-3-ethoxycarbonyl-6-(2-ethoxycarbonylethyl)-4-pyrone (7) in 63% and 19% yields, respectively. Reaction of 1-dimethylphosphono-1-methyl-5-oxo-4-oxaspiro [2.3] hexane (1c) with 4a and 4b under similar conditions gave 2-amino-3-cyano-6-(2-dimethylphosphonopropyl)-4-pyrone (10) and 2-amino-3-ethoxycarbonyl-6-(2-dimethylphosphonopropyl)-4-pyrone (11) in 58% and 63% yields, respectively.View full abstractDownload PDF (619K) -
MICHIKO MIYAHARA, MAKOTO MIYAHARA, SHOZO KAMIYA, AKIHIKO MAEKAWA1981 Volume 29 Issue 8 Pages 2366-2369
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Oxazolidones (Ia→f) were not effective against rat ascites hepatoma AH13 or mouse lymphoid leukemia, L1210. However, among 3-nitroso-2-oxazolidones (IIa→f), compounds IIa, IIb, IIc and IId were active against AH13, and compounds IIa, IIb and IIf were active against L1210. Cyclic N-nitrosocarbamates and N-nitrosoureas showed greater antitumor effects than the corresponding acyclic N-nitroso compounds. Since the reaction of compounds IIa→f with 4-(p-nitrobenzyl) pyridine gave a purple color, their antitumor mechanism presumably involves alkylation ; but there was no correlation between the antitumor activities and the color intensities.View full abstractDownload PDF (501K) -
MASAYOSHI YAMAGUCHI, MASATSUGU KURA, SHOJI OKADA1981 Volume 29 Issue 8 Pages 2370-2374
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe changes of enzyme activities in subcellular fractions of rat liver were investigated after a single oral administration of zinc sulfate (20 mg Zn/100 g body weight). Zinc contents in the fractions of plasma membrane, nuclei, mitochondria, microsomes and cytosol were significantly increased 3 h after zinc administration. On the other hand, a significant decrease of the microsomal glucose-6-phosphatase activity and a remarkable elevation of the mitochondrial succinate dehydrogenase activity were caused by zinc administration, while the activities of the plasma membrane Ca2+-adenosine triphosphatase (ATPase), nuclear ribonucleic acid (RNA) polymerase and cytosolic acid phosphatase were not significantly altered. At the lowest dose (5 mg Zn/100 g) used in this experiment, the microsomal glucose-6-phosphatase activity was not significantly decreased, while the mitochondrial succinate dehydrogenase activity was markedly increased. Also, activation of succinate dehydrogenase in the liver mitochondria was observed at 12 h after zinc administration (10 mg Zn/100 g). The present study indicates that zinc taken up by the liver cells accumulates in the mitochondria and the metal may have an effect on the mitochondrial functions.View full abstractDownload PDF (617K) -
HIRONORI YOSHITOMI, SHIGERU GOTO1981 Volume 29 Issue 8 Pages 2374-2379
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe binding of tolbutamide, a representative sulfonylurea-related drug, to bovine serum albumin (BSA) modified completely or partially with three chemicals (p-chloromercuribenzoic acid, p-aminophenylmercuric acetate and p-hydroxynitrobenzyl bromide) was investigated by means of an equilibrium dialysis method. Scatchard plots of the data indicated that : (1) free sulfhydryl groups in the BSA molecule are not important binding sites for tolbutamide, (2) two tryptophan residues in the BSA molecule form a hydrophobic region, (3) one of the two tryptophan residues in the BSA molecule may be related to the binding of tolbutamide. These results are discussed in relation to the mechanisms responsible for the binding of sulfonylurea-related compounds to serum albumin.View full abstractDownload PDF (615K) -
TAKAKO WATANABE1981 Volume 29 Issue 8 Pages 2379-2382
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe distribution of histamine N-methyltransferase (HMT, EC 2. 1. 1. 8) activity was studied in various tissues of the guinea-pig and rat. The properties of HMT in rat kidney were shown to differ from those of HMT in the brain and kidney of guinea-pig and the brain of rat. Quinacrine, a potent HMT inhibitor, inhibited the activity of HMT by 50% at concentrations of about 10-5 M in rat kidney and about 10-7 M in other tissues.View full abstractDownload PDF (451K) -
HIDEJI ITOKAWA, MAKOTO MORITA, SUSUMU MIHASHI1981 Volume 29 Issue 8 Pages 2383-2385
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new and two known diarylheptanoids were isolated from the rhizomes of Alpinia officinarum HANCE (Zingiberaceae). The structure of the new compounds was determined to be 1, 7-diphenylhept-4-en-3-one (1) and 7-(4"-hydroxy-3"-methoxyphenyl)-1-phenylhept-4-en-3-one (3) on the basis of the spectral data and chemical correlation.View full abstractDownload PDF (416K) -
YOSHIKAZU MATSUSHIMA, YOSHIHARU KARUBE, TATSUO MAEDA, MASATO OHYA, AKI ...1981 Volume 29 Issue 8 Pages 2385-2387
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTumor tissues were clearly visualized in scintigrams of mice bearing Ehrlich ascites tumor a few hours after the administration of ethylenediamine-N, N-diacetic acid labeled with 99mTc.View full abstractDownload PDF (475K) -
ISAO KITAGAWA, MOTOMASA KOBAYASHI, TATSUYA INAMOTO, TOHRU YASUZAWA, YO ...1981 Volume 29 Issue 8 Pages 2387-2391
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical structures are reported for six antifungal lanostane-type triterpene-oligoglycosides from the Okinawan sea cucumber Stichopus chloronotus (BRANDT). The compounds are : stichlorosides A1 (9), B1 (15), C1 (20) [having stichlorogenol (3) as the aglycone] and A2 (10), B2 (16), C 2 (21) [dehydrostichlorogenol (4) as the aglycone].View full abstractDownload PDF (526K) -
HARUYOSHI KODAIRA, MASAYUKI ISHIKAWA, YASUO KOMODA, TERUMI NAKAJIMA1981 Volume 29 Issue 8 Pages 2391-2393
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe methanol extract of the bark of Fraxinus japonica BLUME was fractionated with the guidance of inhibitory activity on rabbit platelet aggregation induced by arachidonic acid. The following active principles were identified : 3-methoxy-4-hydroxyphenylethanol (I) (which also exists in the animal body as a dopamine metabolite), p-hydroxyphenylethanol (II), 2, 6-dimethoxy-p-benzoquinone (III), compounds (IV), (V), and esculetin.View full abstractDownload PDF (440K) -
SACHIKO YAMADA, KEIKO NAKAYAMA, HIROAKI TAKAYAMA1981 Volume 29 Issue 8 Pages 2393-2396
Published: August 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStereochemical configurations of biologically prepared 25-hydroxyvitamin D3 26, 23-lactone (calcidiol lactone) at C-23 and C-25 are determined to be S and R, respectively, by comparison of its high performance LC retention time with those of (23S, 25R)-and (23R, 25S)-25-hydroxyvitamin D3 26, 23-lactone which have been synthesized stereoselectively starting from C-22 steroid aldehyde and (R)-or (S)-citramalic acid.View full abstractDownload PDF (476K)
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