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Saburo SHIMABAYASHI, Hideji TANAKA, Masayuki NAKAGAKI
1989 Volume 37 Issue 9 Pages
2514-2515
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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The solubility product (K
sp) of hydroxyapatite (HAP) in ionic surfactant solutions decreased with an increase in the adsorbed amount of the surface-active ions (dodecylammonium and dodecyl sulfate ions). In the presence of nonionic surfactant (polyoxethylene(10) octylphenyl ether), K
sp was almost constant within the limit of experimental error. It was concluded that the decrease in K
sp is due to the decrease in the chemical potential of HAP through the adsorption of the surface-active ion on HAP, and due to the spontaneous change in the constituent ions of the HAP surface (i.e., surface complex formation) by ion-exchange with the surface-active ion.
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Shigeru OHMIYA, Masayo NOGUCHI, Chin-Yuen CHEN, Isamu MURAKOSHI, Hirot ...
1989 Volume 37 Issue 9 Pages
2516-2518
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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N-Alkyl-2-pyridones reacted on irradiation with aliphatic tert-amines, such as triethylamine and N-methyl-piperidine, by way of addition of an α-C-H bond of the amines to the pyridone nucleus, yielding 4-substituted 3, 4-dihy-dropyridin-2(1H)-ones (4, 5 and 10) and 6-substituted 3, 6-dihydropyridin-2(1H)-ones (3 and 9).
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Setsuo SAITO, Hiroshi UZAWA, Fumi NAGATSUGI
1989 Volume 37 Issue 9 Pages
2519-2522
Published: September 25, 1989
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Coupling reagents were prepared from corresponding benzaldehyde oximes by successive treatment with chlorine and Et
3N; the products were used without purification because of their instability. The reactions of 2, 3, 4, 6-tetra-O-acetyl-1-thio-β-D-glucopyranose (1) with the coupling reagents obtained from benzaldehyde oxime (2a) and phenylacet-aldehyde oxime (2b) gave normal 1, 3-dipolar addition products (3a and 3b, respectively) in good yields. The reactions of 1 with the coupling reagents obtained from p- (2c), m- (2d), and o-methoxybenzaldehyde oxime (2e) gave the 1, 3-addition products chlorinated on the benzene ring; 3c and 3d from 2c, 3e and 3f from 2d, and 3g from 2e. On the other hand, the reactions of 1 with the coupling reagents obtained from p-chloro- (2f) and p-nitrobenzaldehyde oxime (2g) gave no 1, 3-addition product.
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Hiroshi SUEMUNE, Yoshihiro MIYAO, Kiyoshi SAKAI
1989 Volume 37 Issue 9 Pages
2523-2524
Published: September 25, 1989
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The highly functinoalized cyclopentenone (3), obtainable by facile silica-gel-catalyzed air oxidation of the cyclopentenone (2), was converted to the key intermediate for the synthesis of dl-plinol B.
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Kenzo HARIMAYA, Noriko ARAI, Seiichi INAYAMA
1989 Volume 37 Issue 9 Pages
2525-2527
Published: September 25, 1989
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A new pseudoguaianolide named 11βH-dihydro-4-epineopulcehllin (1a) was isolated from the methanol extract of Gaillardia grandiflora. The stereostructure was determined on the basis of spectral evidence, especially proton nuclear magnetic resonance (including the
1H-
1H correlation spectroscopy technique), and was confirmed by the transformation from neopulchellin (2a).
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Kenzo OKADA, Yukiyoshi TAMURA, Masaji YAMAMOTO, Yoshimoto INOUE, Ryoji ...
1989 Volume 37 Issue 9 Pages
2528-2530
Published: September 25, 1989
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The organic extracts of two licorices, known in commerce as Russian and Xinjiang licorices, exhibited potent antimicrobial and antioxidant activity. The bioassay-directed chemical investigation of both licorices revealed glabrene, glabridin, and licochalcones A and B as active principles.
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Mineo SHIMIZU, Syunji HORIE, Satoshi TERASHIMA, Hajime UENO, Toshimits ...
1989 Volume 37 Issue 9 Pages
2531-2532
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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Aldose reductase (AR) inhibitory activity-directed fractionation of the 70% ethanolic extract of Para-parai mi, Phyllanthus niruri, has led to the isolation of three active components, ellagic acid (1), brevifolin carboxylic acid (4) and ethyl brevifolin carboxylate (5). Among them, 1 showed the highest inhibitory activity, being about 6 times more potent than quercitrin, which is a known natural inhibitor of AR.
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Kiyoshi KONISHI, Hirokazu ADACHI, Kiyoshi KITA, Shinzaburo TAKAMIYA, R ...
1989 Volume 37 Issue 9 Pages
2533-2534
Published: September 25, 1989
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The effect of tetragalloylglucose (1, 2, 3, 6-tetra-O-galloyl-β-D-glucose) on purified complex II (succinate-ubiquinone oxidoreductase) of the mitochondorial electron transport system of Ascaris muscle were studied. Both succinate-ubiquinone-1 (Q
1) oxidoreductase, and succinate dehydrogenase measured with 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) in the presence of phenazine methosulfate (PMS) were inhibited by tetragalloylglucose. The inhibitions of both reductase activities of complex II were of competitive type, and the inhibitor constant (K
i) for Ascaris complex II (148nM) was lower than that for rat liver complex II (1.5μM). Thus, Ascaris complex II is much more sensitive to this inhibitor than the mammalian counterpart.
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Tadayori SHIMIZU, Toshiyuki MASUZAWA, Yasutake YANAGIHARA, Hajime ITOH ...
1989 Volume 37 Issue 9 Pages
2535-2536
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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The mitogenicity and lethal toxicity of chemically synthesized lipid A analogs, in which 2, 3-acyloxyacyl-glucosamine-4-phosphate (acyl-GlcN-4P) is linked to a tetraacetyl (Ac
4)-monosaccharide, i.e., Ac
4-glucose (A-211), Ac
4-mannose (A-212), Ac
4-galactose (A-213) or Ac
4-glucosamine (A-214), were compared with those of tetraacetyl-3-deoxy-D-manno-2-octulosonic acid (Ac
4-KDO) linked to acyl-GlcN-4P (A-203). All the compounds ewre capable of increasing incorporation of
3H-thymidine into splenocytes of C57BL/6 mice at doses of 50 and 100 μg/ml, but the mitogenic activity of A-203 at these doses seems to be stronger than those of the analogs. Intravenous injection of A-203, A-211, and A-213 did not exhibit lethal toxicity even at a high dose (50 μg/mouse) in C57BL/6 mice loaded with D-galactosamine hydrochloride. However, A-212 and A-214 showed lethality at the doses of 10 and 50 μg/mouse, respectively. The findings indicate that the biological activity of these compounds is affected by the kind of monosaccharide linked to acyl-GlcN-4P.
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Junzo NAKAMURA, Hideo SHIOTA, Hitoshi SASAKI, Juichiro SHIBASAKI
1989 Volume 37 Issue 9 Pages
2537-2538
Published: September 25, 1989
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The blood concentrations of salicyluric acid and salicylic acid following rectal, intravenous and oral administrations of salicyluric acid (5, 10 and 60 mg/kg, respectively : salicylic acid equivalent) were determined in dogs. After rectal administration, a small amount of sailcyluric acid was absorbed in intact form. The rest was hydrolyzed to salicylic acid, which was subsequently absorbed. The blood concentration of salicylic acid was maintained at 0.4-0.7 μg/ml from 2 to 12h. Following intravenous administration of salicyluric acid, salicyluric acid was detected in the blood but was rapidly eliminated. A trace amount of salicylic acid was detected, suggesting that systemic de-conjugation of glycine was involved. After oral administration of salicyluric acid, salicyluric acid was well absorbed. Salicylic acid was detected at low concentration for 12h. Species difference in the metabolic fate of salicyluric acid in dogs, rabbits, rats and humans reported previously is discussed.
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Ichimaro YAMADA, Hiroaki MIZUTA, Tomoko GODA, Keiichiro HAGA, Kenji OG ...
1989 Volume 37 Issue 9 Pages
2539-2541
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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The gastric pH of fasting beagle dogs was measured by using an ion-selective field effect transistor pH sensor. In addition, a novel procedure to control the gastric pH in fasting beagle dogs was investigated Inter-and intra-day variations in the gastric pH of the dogs were observed. The gastric pH of the dogs could be controlled by a single intravenous administration of omeprazole, an H
+, K
+-adenosine triphosphatase (ATPase) inhibitor (1mg/0.25ml/kg). The pH in the stomach was 6.6±0.2(mean±S.D., n=6) at 1h after the omeprazole treatment, and this level of pH was maintained for a period of at least 3h. Beagle dogs in which the gastric pH has been controlled by omeprazole are considered to be useful as an animal model to be used for the pharmaceutical evaluation of drugs in subjects with a low acidity level.
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Kanji TAKADA, Mamoru OH-HASHI, Yoshihiro FURUYA, Hiroshi YOSHIKAWA, Sh ...
1989 Volume 37 Issue 9 Pages
2542-2544
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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The availability of cyclosporin A (CyA) administered as an enteric solid dispersion preparation of which the composition is CyA : HCO-60
[○!R] : HP-55
[○!R]=1 : 2 : 8 was evaluated in rabbits. The additives are surfactant (polyoxyethy-lated, 60μmol, castor oil derivative, HCO-60
[○!R]) and enteric coating material (hydroxypropylmethyl cellulose phthalate, HP-55
[○!R]), which are generally used as pharmaceutical additives. Both the systemic and lymphatic availabilities of CyA from this solid preparation were measured in rabbits after intrastomach administration, 7mg CyA/kg, and were compared with those from conventional oily solution, Sandimmun
[○!R]. The mean systemic availability of CyA from the solid preparation was 57% which is about 1.5 times greater than that obtained from Sandimmun. THe amounts of CyA transferred into the thoracic lymphatics within 12h from solid dosage form and Sandimmun are 0.62±0.16(S.D.)% and 0.13±0.05% of the administered CyA dose. These results support the usefulness of the new solid dosage form of CyA.
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Fumio UEDA, Tadashi HIGASHI, Yoshikazu AYUKAWA, Tadao FUJIE, Shoko YOK ...
1989 Volume 37 Issue 9 Pages
2545-2546
Published: September 25, 1989
Released on J-STAGE: March 31, 2008
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The hygroscopicity of the complexes composed of thiamine disulfide (TDS) and higher fatty acids and the dissolution of TDS from the complexes were studied. The hygroscopicity of TDS was reduced dramatically by the formation of the (fatty acid)
6(TDS) complexes. Regarding the dissolution of TDS from the complexes, plots of T
50 or T
80 (the time required for 50% or 80% of TDS to dissolve, respectively) against the carbon numbers of the constituent fatty acids showed a zig-zag pattern, and C17 fatty acid gave the longest T
50 and T
80.
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Takeo KAWAGUCHI, Kozo ISHIKAWA, Toshinobu SEKI, Kazuhiko JUNI, Shoji F ...
1989 Volume 37 Issue 9 Pages
2547-2549
Published: September 25, 1989
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N
4-Benzoyl-2', 3'-dideoxy-2', 3'-didehydrocytidine (Bz-DDCN) was synthesized as a novel prodrug of 2', 3'-dideoxy-2', 3'-didehydrocytidine (DDCN), which is a reverse transcriptase inhibitor and is considered to be a potential antiacquired immunodeficiency syndrome agent. Chemical and enzymatic regeneration of DDCN from the prodrug has been investigated in both in vitro and in vivo experiments. Bz-DDCN regenerated DDCN under basic conditions (>pH 8), while cleavage of the N-glycosidic linkage and production of N
4-benzoylcytosine were observed under acidic conditions (>pH 6). DDCN was enzymatically regenerated from the prodrug in the presence of several enzyme preparations, including human plasma. DDCN and Bz-DDCN were intravenously administered to mice and the plasma concentrations of DDCN and the prodrug were measured. Though DDCN levels following direct DDCN administraiton decreased exponentially with a half-life of 14.5min, the plasma levels of DDCN following the prodrug administration were sustained above 2μM for over 3h.
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Hiroki TAKAHATA, Mayumi TAJIMA, Yasunori BANBA, Takefumi MOMOSE
1989 Volume 37 Issue 9 Pages
2550-2552
Published: September 25, 1989
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Mercuric acetate driven cyclization of γ-hydroxy-δ, ε-unsaturated urethanes 1a, b proceeded regio- and stereoselectively to afford cis-2-acetoxymercurymethyl-3-hydroxypyrrolidines 2a, b, respectively. These were transformed into the key intermediates for several biologically active compounds.
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Kazuo IGUCHI, Shuichi SAITOH, Yasuji YAMADA
1989 Volume 37 Issue 9 Pages
2553-2554
Published: September 25, 1989
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Two new sterols, litosterol (2a) and 5, 6-epoxylitosterol (3a), with an oxygen function-ality at the C-19 position were isolated from the Okinawan soft coral Litophyton viridis. The structures were elucidated on the absis of spectroscopic analysis.
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Masayuki YOSHIKAWA, Yoshihiko OKAICHI, Bae Cheon CHA, Isao KITAGAWA
1989 Volume 37 Issue 9 Pages
2555-2557
Published: September 25, 1989
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(-)-Aristeromycin, a carbocyclic nucleoside with various biological activities, was synthesized from D-glucose using a Michael-type addition reaction of N
6-benzoyladenine with a nitro-cyclopentene derivative as its key step.
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Tomoo AOYAMA, Yuji SUZUKI, Hiroshi ICHIKAWA
1989 Volume 37 Issue 9 Pages
2558-2560
Published: September 25, 1989
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Neural networks, which are also called perceptrons or multi-layer networks, were found to be useful tools in decision making. The model study showed that the predictions by the neural network were better than those by the linear learning machine and cluster analysis.
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Nobuko SHIMIZU, Tamiko OHKURA, Hiroyuki AKITA, Takeshi OISHI, Yoichi I ...
1989 Volume 37 Issue 9 Pages
2561-2563
Published: September 25, 1989
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Microbiological asymmetric induction of 4, 9-dimethyl-3, 5-dioxo-Δ
4(10)-octalin, (±)-1 was accomplished with various yeasts. With properly selected microorganisms, (+)-4, (9S)-dimethyl-(5S)-hydroxy- (2) and (-)-4, (9R)-dimethyl-(5S)-hydroxy-3-oxo-Δ
4(10)-octalin (3), (-)-4, (9R)-dimethyl-(3S)-hydroxy- (6) and (+)-4, (9S)-dimethyl-(3S)-hydroxy-5-oxo-Δ
4(10)-octalin (7) were obtained with high optical purity.
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Mitsuaki WATANABE, Mutsuhiro DATE, Kenji KAWANISHI, Masao TSUKAZAKI, S ...
1989 Volume 37 Issue 9 Pages
2564-2566
Published: September 25, 1989
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Aryl tetramethylphosphorodiamidates were effectively lithiated with sec-BuLi at -105°C to give ortho-lithiated species which provide ortho-substituted phosphates by treatment with a variety of electrophiles.
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Shinya HARUSAWA, Toshiko KUROKAWA, Harumi FUJII, Ryuji YONEDA, Takushi ...
1989 Volume 37 Issue 9 Pages
2567-2569
Published: September 25, 1989
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A new synthesis of a 10-membered thiolcarbonate containing a (Z)-double bond and its conversion into (Z)-allylic sulfides are described.
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Hiromu HARADA, Atsushi TSUBAKI, Tetsuhide KAMIJO, Kinji IIZUKA, Yoshia ...
1989 Volume 37 Issue 9 Pages
2570-2572
Published: September 25, 1989
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Cyclohexylnorstatine [(2R, 3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid] (1) and allocyclohexylnorstatine [(2S, 3S)-3-amino-4-cyclohexyl-2-hydroxybutyric acid] (2), designed as key amino acids in renin inhibitors, were synthesized diastereoselectively and simply from Boc-L-phenylalaninol.
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Yasuhide SEKI, Satoshi WATANABE, Sachiko SEKI
1989 Volume 37 Issue 9 Pages
2573-2575
Published: September 25, 1989
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Sulfite is reduced to dithionite under hydrogen atmosphere with periplasmic hydrogenase and cytochrome c
3 from a sulfate-reducing bacterium Desulfovibrio vulgaris Miyazaki K.
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