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MACHIKO ONO, HINAKO TANAKA, SHINZO TAMURA
1982 Volume 30 Issue 6 Pages
1933-1941
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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1-Ethoxy-3-(p-methylphenylimino)-1-propene (IV) was prepared to elucidate the reaction sequence in the formation of 1-(p-methylphenylamino)-3-(p-methylphenylimino)-1-propene (malonaldehyde dianil of p-toluidine) (III) from β-ethoxyacrolein (I) and p-toluidine. The reaction of I and p-toluidine in benzene solution was followed spectrophotometrically, and evidence was obtained for the existence of IV as an intermediate in the formation of III. Acetic acid acted as an effective catalyst for the formation of β-(p-toluidino) acrolein (II) from I and p-toluidine in benzene solution. β-(p-Nitroanilino) acrolein (VIII) and β-(4-pyridylamino) acrolein 1-oxide (IX) were prepared from I and the corresponding amines under acidic conditions.
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CHOJI KASHIMA, AKIRA KATOH, YUKO YOKOTA, YOSHIMORI OMOTE
1982 Volume 30 Issue 6 Pages
1942-1946
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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1, 4, 6-Trisubstituted 2 (1H)-pyrimidinethiones (Ia-k) underwent Dimroth-type ring transformation with ammonia and primary alkyl amines in the presence of silver perchlorate to afford 2-(N-substituted) aminopyrimidines (IIa, c, d, f, j, k) and pyrimidinium perchlorates (IIIa-c, e-j), respectively. Furthermore, pyrimidinium perchlorates (III) were converted into 2 (1H)-pyrimidinones (IV) in high yields by hydrolysis with concentrated hydrochloric acid.
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HIDECI MIKI
1982 Volume 30 Issue 6 Pages
1947-1951
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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In the reaction of 2, 4 (1H, 3H)-quinazolinedione with phosphoryl chloride in the presence of excess N-methylpyrrolidine, the hydroxy groups at the 2- and 4-position of the quinazoline nucleus were replaced by the N-methyl-4-chlorobutylamino group and chlorine to give 4-chloro-2-(N-methyl-4-chlorobutylamino) quinazoline in good yield. By using this reaction, several new 4-chloro-2-dialkylaminoquinazoline derivatives were obtained from N-alkylcyclic amines and 2, 4 (1H, 3H)-quinazolinedione.
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MUTSUO KOZUKA, TOKUNOSUKE SAWADA, FUMIKO KASAHARA, EIJI MIZUTA, TOSHIO ...
1982 Volume 30 Issue 6 Pages
1952-1963
Published: June 25, 1982
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The structures of seven novel potent granulation-inhibiting principles isolated from the buds of Eucalyptus globulus LABILL., were examined on the basis of physicochemical data, especially of
1H-nuclear magnetic resonance (NMR),
13C-NMR, mass spectrum (MS) and circular dichroism (CD). The structures (but not the complete stereochemistry) of euglobal-Ia
1, -Ia
2, -Ib, -Ic, -IIa, -IIb and -IIc were proposed to be 2-7 and 8, respectively.
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MUTSUO KOZUKA, TOKUNOSUKE SAWADA, EIJI MIZUTA, FUMIKO KASAHARA, TOSHIO ...
1982 Volume 30 Issue 6 Pages
1964-1973
Published: June 25, 1982
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The structures of three novel potent granulation-inhibiting principles, euglobal-III (1), -IVb (2) and -VII (3) were deduced, except for the absolute configurations, on the basis of proton magnetic resonance,
13C-nuclear magnetic resonance and mass spectral evidence.
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MOHAMMED MOHAMMED YOUSIF, SEITARO SAEKI, MASATOMO HAMANA
1982 Volume 30 Issue 6 Pages
1974-1979
Published: June 25, 1982
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Quinoline 1-oxides (1a-e) readily react with 2-phenyl-2-thiazolin-4-one (2) in acetic anhydride at room temperature to afford the corresponding 5-(2-quinolyl) thiazolones (3a-e) in good yields. The reaction of 4-chloroquinoline 1-oxide (1f) gives 4-acetoxy-5-(4-chloro-2-quinolyl)-2-phenylthiazole (4). Hydrolyses of 1a-e with 48% hydrobromic acid under reflux give 2-quinolinemethanethiols as the hydrobromides (6a-e). Similar results were obtained from the reaction of isoquinoline 2-oxide (7), but pyridine 1-oxide was unreactive.
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MASAYUKI KUZUYA, SEIJI ITO, FUMIO MIYAKE, TAKACHIYO OKUDA
1982 Volume 30 Issue 6 Pages
1980-1985
Published: June 25, 1982
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Intramolecular cycloaddition of azaquinonoid-ketene (4) generated from benzotriazinone derivative to N, N-dimethylanilino group afforded "unrearranged" acridone in sharp contrast to a carbon analog series (1). Molecular orbital calculations and conformational studies using a model compound did not show much difference between azaquinonoid-ketene (11) and quinonoid-ketene (12), indicating similar propensity toward the [
π4
a+
π2
a] pathway of 4 in terms of FMO theory. These results led us to suggest the involvement of a concealed process in the transformation of 4 to "unrearranged" acridone (9), i. e., a [
π4
a+
π2
a] cycloaddition at the initial stage, by analogy with the carbon analog (1).
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TOSHIO MIYASE, AKIHIDE OHTSUBO, AKIRA UENO, TADATAKA NORO, MASANORI KU ...
1982 Volume 30 Issue 6 Pages
1986-1991
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Five new pterocarpans, melilotocarpans A (I), B (II), C (III), D (IV) and E (V), have been isolated from Melilotus alba DESR. and their structures have been determined from chemical and spectral data.
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HISASHI ISHII, KAZUO KOYAMA, IHSHENG CHEN, SHENGTEH LU, TSUTOMU ISHIKA ...
1982 Volume 30 Issue 6 Pages
1992-1997
Published: June 25, 1982
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The structure of integriquinolone (1), a new phenolic quinolone which was isolated from Xanthoxylum integrifoliolum (MERR.) MERR. (Fagara integrifoliola MERR.), was established as 6-hydroxy-4-methoxy-1-methyl-2-quinolone by synthesis of ethyl integriquinolone (2), 6-ethoxy-4-methoxy-1-methyl-2-quinolone.
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ORLANDO M. SOEIRO, ANTONIOJ.R.da SILVA, RODERICK A. BARNES
1982 Volume 30 Issue 6 Pages
1998-2002
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Salutarine, the principal alkaloid of Croton salutaris CASAR has been treated with phenyllithium and methyllithium to yield the corresponding salutarinols. treatment of 7-phenylsalutarinol (not isolated) with acid produced the racemic form of 7-phenylthebaine. The mixture of epimeric 7-methylsalutarinols yielded mainly the dehydration product, the 7-methylene derivative of salutarine. A comparison of the
13C-nuclear magnetic resonance spectra of these and other derivatives of salutarine permitted a complete assignment of the chemical shifts.
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YUTAKA YAMAMOTO, AKIHIKO YANAGI
1982 Volume 30 Issue 6 Pages
2003-2010
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Introduction of an acyl group at the α-, β-, and γ-positions of pyridine nuclei was accomplished. 2-Trimethylstannyl-pyridine and -quinoline and 1-trimethylstannyliso-quinoline directly reacted with various acyl chlorides to give the corresponding 2-pyridyl, 2-quinolyl, and 1-isoquinolyl ketones, respectively. Reaction of 3-trimethylstannyl-pyridine, -quinoline, and -isoquinoline with acyl chlorides proceeded smoothly under catalysis by PdCl
2 or PdCl
2 (PPh
3)
2 to afford the corresponding ketones in good yields. Similarly, 4-pyridyl, -quinolyl, and -isoquinolyl ketones were prepared from the corresponding 4-trimethylstannyl derivatives and acyl chlorides.
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TAKAYUKI NAITO, SUSUMU NAKAGAWA, TAKAAKI OKITA, HARUHIRO YAMASHITA, TE ...
1982 Volume 30 Issue 6 Pages
2011-2019
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A series of 2, 9-disubstituted adenine derivatives was prepared and evaluated for bronchodilating activity. 9-(2-Cyclohexenyl), 9-tetrahydropyranyl and 9-benzyl derivatives of 2, 6-dichloropurine were converted to the 2-chloroadenines. Subsequent nucleophilic substitution of the 2-chloro group with alkoxides, mercaptides and amines afforded the desired compounds. 9-Cyclohexyl derivatives were prepared by hydrogenation of the corresponding 9-cyclohexenyl compounds. Bronchodilating activities of the new adenine derivatives were evaluated in a number of biological systems. 9-(2-Cyclohexenyl)- and 9-cyclohexyladenines having an ethoxy, n-propoxy, n-butoxy or n-propylthio group at the 2-position showed potent bronchodilating activity. Reduced activity was observed with lower or higher alkoxy homologs and branched alkoxy congeners. 9-Cyclohexyl-2-n-propoxy-9H-adenine (designated as BB-1502) was selected for further studies in view of its high intrinsic activity and favorable pharmacological profile.
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TAMOTSU NIKAIDO, TAICHI OHMOTO, HIROSHI SAITOH, USHIO SANKAWA, SEIICHI ...
1982 Volume 30 Issue 6 Pages
2020-2024
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Cyclic adenosine monophosphate (AMP) phosphodiesterase inhibitors contained in Polygala tenuifolia WILLD. were identified as saponins and oleic acid. The concentrations of onjisaponins E, F and G required to give 50% inhibition (IC 50) were of the sameor der as that of papaverine. A kinetic study revealed that onjisaponin F acts non-competitively against cyclic AMP phosphodiesterase, like papaverine. Onjisaponin F exhibited a prolongation effect on hexobarbital sleeping time in mice.
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KIMIYE BABA, YOUKO MATSUYAMA, MITSUGI KOZAWA
1982 Volume 30 Issue 6 Pages
2025-2035
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The root of Angelica pubescens MAXIM. (Umbelliferae) afforded seven new coumarins, angelols B-H (2-8), together with a known coumarin, angelol A (formerly simply called angelol). The structures of these coumarins were determined on the basis of spectral and chemical evidence as 6-(1-acyloxy-2, 3-dihydroxy-3-methylbutyl)-7-methoxycoumarins and 6-(2-acyloxy-1, 3-dihydroxy-3-methylbutyl)-7-methoxycoumarins and 6-(2-acyloxy-1, 3-dihydroxy-3-methylbutyl)-7-methoxycoumarins. Furthermore, in the course of this investigation we revised the reported structure of angelol A (1)
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KIMIYE BABA, YOUKO MATSUYAMA, TOSHIMASA ISHIDA, MASATOSHI INOUE, MITSU ...
1982 Volume 30 Issue 6 Pages
2036-2044
Published: June 25, 1982
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The absolute configurations of angelols A-H (1-8) isolated from Angelica pubescens MAXIM. (Umbelliferae) were determined to be as shown in Chart 1 by means of chemical, spectral and X-ray analysis. Furthermore, the stereostructure of angelol B (2) was determined to be as shown in Fig. 1 on the basis of X-ray analysis.
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ISAO KITAGAWA, MOTOMASA KOBAYASHI, YOSHIMASA KYOGOKU
1982 Volume 30 Issue 6 Pages
2045-2050
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Triterpenoidal oligoglycosides contained in the Cuvierian tubules of the Bahamean sea cucumber Actinopyga agassizi SELENKA were shown to consist of a new lanostane-type triterpene tetraglycoside sulfate (24-dehydroechinoside A) (10) and holothurin A (11) in an approximate ratio of 2 : 1. The chemical structure of 24-dehydroechinoside A (10) was elucidated on the basis of chemical and physicochemical evidence.
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TADASHI SASAKI, AKIRA NAKANISHI, MASATOMI OHNO
1982 Volume 30 Issue 6 Pages
2051-2060
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Various silylated heterocycles having amide functionality were treated with 1-adamantyl chloride (1) in the presence of a Lewis acid to give the corresponding N-adamantylated heterocycles. If α-position to the reacting lactim nitrogen was substituted, the reaction no longer occurred, or the adamantylation occurred at the position other than the expected nitrogen. These facts are attributed to a steric blocking effect of the α-substituent. While the same treatment of the thioamide 46 gave the S-adamantylated product, 48 and 51 afforded in contrast the N- and S-adamantylated products, respectively ; this result can be explained in terms of steric effect. Analogously, silylated 2-pyrazolines and triazoles were adamantylated at nitrogen. The reactions of 2-trimethylsilylthiophene, furan and -pyridine with 1 failed to give site-selective monoadamantylation.
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GENICHIRO NONAKA, HIROAKI NISHIMURA, ITSUO NISHIOKA
1982 Volume 30 Issue 6 Pages
2061-2067
Published: June 25, 1982
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Along with gallic acid, ellagic acid, (+)-catechin and procyanidins B-1 and B-3, seven new gallates of phenol glucosides (compounds 1-7) have been isolated from the bark of Quercus stenophylla MAKINO (Fagaceae). On the basis of chemical and spectral evidence, the structures of compounds 1, 2, 4, 5 and 6 have been established respectively as 6"-O-gallate (1), 3"-O-gallate (2), 4', 6"-di-O-gallate (4), 4", 6"-di-O-gallate (5) and 3", 4", 6"-tri-O-gallate (6) of salidroside (p-hydroxyphenethyl alcohol 1-O-β-D-glucopyranoside). Similarly, compounds 3 and 7 have been characterized as 3', 4'-dihydroxyphenethyl alcohol 1-O-β-D-(6"-O-galloyl)-glucopyranoside (3) and 2, 4, 6-trimethoxyphenol 1-O-β-D-(6'-O-galloyl)-glucopyranoside (7), respectively.
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ETSUJI YAMANAKA, NAOKI SAITO, YUKO SUZUKI, SHINICHIRO SAKAI
1982 Volume 30 Issue 6 Pages
2068-2076
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Oxindole alkaloids chosen as starting materials were isopteropodine (1a) pteropodine (1b) isoformosanine (7a) and formosanine (7b). Reduction of the iminoethers prepared from the oxindole alkaloids with Et
3 O^
+B^
-F
4, with NaBH
3 (OAc) or with NaBH
4/SnCl
4·2Et
2O afforded the indoline derivatives (3a, 3b, 9a, 9b). The configuration at C
7 of 3a, b was determined by NMR analysis of the N (a)-acetyl-N (b)-oxides (6a, b). The signals of H-14β were observed at high field (δ0.5-1.0) owing to the shielding effect of the aromatic ring in all A type compounds studied. Oxidative conversion of the indolines to indole alkaloids was achieved by using MnO
2 or Me
2SO/ (COCl)
2/Et
2N as oxidizing agents, and the latter reagent gave better results than the former. Tetrahydroalstonine (11) and akuammigine (12) were obtained from 3a, b, and 19-epiajmalicine (14) and 3-iso-19-epiajmalicine (15) from 9a, b. The A type compounds were more susceptible than the B type compounds to the present reduction and oxidation sequence.
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YUTAKA KAWAZOE, NOBUYA TAMURA, TOMOKO YOSHIMURA
1982 Volume 30 Issue 6 Pages
2077-2086
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The present work provides a simple method for the characterization of alkylating agents by measuring the reaction selectivity toward 4-(p-nitrobenzyl) pyridine (NBP) in acetone containing phosphate buffer, evaluated in terms of the selectivity constant, SNBP, which is defined as log {[H
2O]/[NBP]×N%/(100-N%)}, where N% is the percentage molar fraction of NBP alkylation. S
NBP values were determined for about 40 kinds of halides, methanesulfonates, tosylates, sulfates, phosphates, nitrosoureas, and nitrosoguanidines. SNBP can replace the substrate constant, s, of the Swain-Scott equation, and SNBP's of some of the agents examined here were linearly correlated with the s values.
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TERUMICHI IWATANI, MASATSUGU NAITOH, HIDEO TAKASHINA, SHINICHI NAGAMOR ...
1982 Volume 30 Issue 6 Pages
2087-2093
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A highly sensitive and specific gas chromatographic method for the determination of SA-446 [(2R, 4R)-2-(2-hydroxyphenyl)-3-(3-mercaptopropionyl)-4-thiazolidinecarboxylic acid] in human whole blood and urine was established. The mercapto group of SA-446 was alkylated completely with pentafluorobenzyl bromide (PFBB) and then the remaining hydroxyl and carboxyl groups were methylated with diazomethane. As little as 10 picograms of the derivatized SA-446 is detectable by the electron capture technique. The mean recoveries of SA-446 from whole blood and urine by the present method were 95.5% and 93.5%, respectively. The calibration curves for SA-446 were linear in the concentration ranges of 10ng/ml to 10000ng/ml of whole blood and 0.1μg/ml to 100μg/ml of urine. The standard deviation with this method was below 3.0%. This method is highly sensitive, and a small sample size of 250μl is enough to determine SA-446 in human whole blood and urine.
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NORIKO MOTOHASHI, HARUMI EGUCHI, ITSUHIKO MORI
1982 Volume 30 Issue 6 Pages
2094-2098
Published: June 25, 1982
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Two intermediates involved in the synthesis of melanin from L-tyrosine by mushroom tyrosinase (EC 1.14.18.1) were assayed simultaneously by using L-[ring-
3H] tyrosine and L-[carboxyl-
14C] tyrosine. Tritium ions released from the 3-position of L-[3, 5-
3H] tyrosine or the 6-position of L-[2, 6-
3H] tyrosine were isolated as
3H
2O and employed to determine the quantity of L-dopa or leucodopachrome, respectively (
3H
2O method). 5, 6-Dihydroxyindole formed at the decarboxylation step was estimated from the radioactivity remaining after the evolution of
14CO
2 from L-[carboxyl-
14C] tyrosine (
14CO
2-release method). The lower limits of determination in the
3H
2O and the
14CO
2-release methods were 0.1 pmol and nmol of the intermediates, respectively. The formations of L-dopa, leucodopachrome, and 0.1 5, 6-dihydroxyindole were measured at various concentrations of L-tyrosine by both methods, and dopachrome was determined colorimetrically by measuring the absorbance changes at 475nm. The maximum velocities were estimated from Lineweaver-Burk plots.
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SHINJI OHMORI, SACHIKO MIZUNO, MIKIKO IKEDA, KENZABURO YAO
1982 Volume 30 Issue 6 Pages
2099-2104
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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α-Ketobutyric acid is one of the reaction products formed from cystathionine or homoserine by cystathionase. α-Ketobutyric acid was reacted with pentafluorophenylhydrazine, and the hydrazone was extracted with ethyl ether, reacted with diazomethane, and subjected to gas-liquid chromatography with an electron capture detector. This method provides a specific and sensitive assay for cystathionase and cystathionine in biological samples.
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KAZUYUKI HIRANO, YUICHI IIIZUMI, MAMORU SUGIURA, JUN MIYAZAKI, KAZUMAS ...
1982 Volume 30 Issue 6 Pages
2105-2109
Published: June 25, 1982
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A procedure for the determination of the heat-stable alkaline phosphatase activity in serum was developed by using antibody-conjugated paper disks and inhibition by sodium thiocyanate. The placental alkaline phosphatase adsorbed on a paper disk conjugated with antibody was completely inhibited by 3M sodium thiocyanate, but the activity of intestinal alkaline phosphatase adsorbed on the paper disk was unaffected by 3M sodium thiocyanate. The results obtained by the proposed method showed a good correlation with those obtained by the heat-inactivation method (γ=0.991). These results strongly suggest that the proposed method can be utilized as a routine clinical test for the determination of serum placental-type alkaline phosphatase, i. e., placental, Regan, Nagao and Kasahara isoenzymes, from patients with cancer.
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HIROSHI HOSODA, KEIKO SAITO, YUKO ITO, HIROMITSU YOKOHAMA, KAZUO ISHII ...
1982 Volume 30 Issue 6 Pages
2110-2118
Published: June 25, 1982
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In order to develop specific and sensitive immunoassays, carboxylated derivatives of tetrahydrocortisol and tetrahydrocortisone were synthesized. The preparation of the 3-hemisuccinates (23, 27), 21-hemisuccinates (8, 14), 3-hemiglutarates (24, 28), and 21-hemiglutarates (9, 15) of these corticosteroids was carried out starting from cortisol 21-acetate (1). Tetrahydrocortisol monoglucuronides (36, 38) and tetrahydrocortisone monoglucuronides (37, 39) were also prepared.
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AKIRA TOKUMURA, YASOMI HANDA, YASUKO YOSHIOKA, MINORU HIGASHIMOTO, HIR ...
1982 Volume 30 Issue 6 Pages
2119-2126
Published: June 25, 1982
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The electron impact and chemical ionization mass spectra of lysophosphatidic acids and their dimethyl esters were measured by injection of the compounds into a direct inlet system. Dry powders of lysophosphatidic acids were dehydrated on the probe at 200-250°C and the dehydrated lysophosphatidic acids were subjected to electron impact or interaction with ion plasma of the reactant gas, yielding several characteristic ion peaks containing phosphorus. On the other hand, lysophosphatidic acids injected in the probe as solutions in organic solvents were not dehydrated in this temperature range, but were dephosphorylated at highter probe temperatures. When the dimethyl esters were applied to the probe either as powder or solution, they were converted to the monomethyl esters of dehydrated lysophosphatidic acids on the heated probe, possibly by elimination of methanol from the glycerol backbone and polar phosphate portion. The monomethyl esters were also volatilized and subjected to electron impact and chemical ionization, producing ion peaks corresponding to those observed on analysis of dehydrated lysophosphatidic acids.
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HIROSHI HOSODA, SHINICHI MIYAIRI, NORIHIRO KOBAYASHI, TOSHIO NAMBARA
1982 Volume 30 Issue 6 Pages
2127-2132
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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In order to obtain specific antisera for use in immunoassays of 11-deoxycortisol, new hapten-carrier conjugates were prepared from 4-hemisuccinoyloxy-11-deoxycortisol, 4-(carboxymethylthio)-11-deoxycortisol, 4-(2-carboxyethylthio)-11-deoxycortisol and 4-(2-hemisuccinoyloxyethylthio)-11-deoxycortisol by coupling with bovine serum albumin employing the N-succinimidyl ester method. The specificity of anti-11-deoxycortisol antisera elicited in rabbits by immunization with these antigens was tested by crossreaction studies with closely related steroids and by measuring the amount of 11-deoxycortisol in plasma specimens by means of radioimmunoassay. The results showed that the antisera obtained were reasonably specific and useful for the determination of plasma 11-deoxycortisol levels in metyrapone tests. The assay can be done on methylene chloride extracts of plasma.
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HAJIMU YAMAOTO, IKUKATSU SUZUKI, AKIRA MIZUTANI
1982 Volume 30 Issue 6 Pages
2133-2140
Published: June 25, 1982
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When P-MSY, a component of bovine parotid glands, was injected at a dose of 1μg/head/d, daily for 10 d starting 24 h after the transplantation of ascites Ehrlich carcinoma cells, the solid tumor formed was rejected in 6 of 10 mice, and the tumor inhibition rate was 86.4%. Subcutaneous injection of 1μg/head/d, daily for 7 d before transplantation of sarcoma-180 cells resulted in prolongation of the life span of ascites tumor-bearing mice, the mean survival period being 19.4 d against 14.1 d in the control ; T/C was 138%. Such a life-prolonging effect was not observed when P-MSY was administered after the transplantation of the tumor. Electrophoresis of the serum from mice in which the tumor had been rejected after the administration of P-MSY revealed increased quantities of some protein components. By examinations of delayed-type skin reaction, P-MSY was found to hinder significantly the lowering of cellular immunity in tumor-bearing mice.
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TADANORI MAYUMI, KYOKO OKAMOTO, KAORU YOSHIDA, YUICHI KAWAI, HIROKO KA ...
1982 Volume 30 Issue 6 Pages
2141-2146
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The possible preventive effects of ergothioneine on cadmium-induced teratogenesis were examined. Cd (2 mg/kg) was administered i. p. to mice on day 7 of pregnancy. The treatment group of mice was given i. p. ergothioneine daily at a dose of 80 mg/kg during days 5 to 9, whereas the control group was given saline solution. These mice were subjected to Cesarean section on day 17 of gestation, and the number of dead fetuses, the body weight of living fetuses, and external, skeletal and visceral abnormalities were recorded. On the other hand,
109Cd (50μCi/2 mg Cd/kg) was administered i. p. to other pregnant mice on day 7, and the tissue distribution of the Cd was examined on days 8 and 17 of gestation. The results of the series of experiments were as follows. (1) Administration of ergothioneine alone had no effect on external, skeletal and visceral abnormalities. (2) Of 257 cases, fetuses in 79 cases died or were resorbed after Cd administration. The body weight of living fetuses was significantly reduced, and exencephalia (64%), open eye (31.5%) and marked skeletal malformations of cervical, thoracic and lumbar vertebrae were observed. (3) Ergothioneine very significantly reduced the incidences of exencephalia, open eye and skeletal abnormalities caused by Cd. (4) There were no differences between both groups in the in vivo distribution of
109Cd, or in the form of
109Cd present in the liver, kidney and placenta. These results suggest that ergothioneine inhibits Cd-induced teratogenesis through a mechanism other than causing changes in the maternal distribution of Cd and in Cd transfer to fetuses.
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SHIGEO UKAI, CHIHIRO HARA, TADASHI KIHO
1982 Volume 30 Issue 6 Pages
2147-2154
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A water-soluble β-D-glucan (T-5-N) has been isolated from 1N sodium hydroxide extract of the fruit bodies of Dictyophora indusiata FISCH. T-5-N, [α]
18D+28.7°(c=0.5, H
2O), IR ν
KBrmaxcm
-1 : 890, was homogeneous as judged by ultracentrifugal analysis and Tiselius-type electrophoresis. Structural analyses indicated that T-5-N has a main chain composed of β-1→3 linked D-glucopyranosyl residues, and two single β-1→6 linked D-glucopyranosyl units are attached as side chains, on average, to every seventh sugar residue of the main chain. In addition, a few internal 1→6 linkages and branching points at position 2 of the β-1→3 linked main chain are also present in the molecule.
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MICHINAO MIZUGAKI, TSUNEO UNUMA, TOMOKO NISHIMAKI, TAKAYUKI SHIRAISHI, ...
1982 Volume 30 Issue 6 Pages
2155-2160
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The stereochemical mechanism of the reduction of cis-2-octenoyl-coenzyme A (-CoA) catalyzed by cis-2-enoyl-CoA reductase from E. coli was studied. cis-2-[7, 8-
2H
5] Octenoyl-CoA was incubated with partially purified cis-2-enoyl-CoA reductase in the presence of 4R or 4S-[4-
2H
1] nicotinamide adenine dinucleotide phosphate (NADPH). The octenoyl-CoA was also incubated with the enzyme in the presence of NADPH in
2H
2O. Octanoic acids synthesized were isolated and analyzed by gas chromatography-mass spectrometry (GC-MS) to examine the localization of deuterium atoms in the molecule. The octanoic acids isolated from the incubation mixtures were converted to their CoA esters, and then they were dehydrogenated by the action of acyl-CoA oxidase, which had previously been shown to catalyze the anti-elimination of the pro-2R and pro-3R hydrogens of acyl-CoA. The resulting products, trans-2-octenoyl-CoAs, were converted to methyl esters and their deuterium contents at the C-2 or C-3 position were also analyzed by GC-MS. The results suggested the following stereochemical features of the reaction catalyzed by cis-2-enoyl-CoA reductase. 1) pro-4R Hydrogen of NADPH was incorporated into the C-3 position of octenoyl-CoA. 2) Hydrogen from the medium was introduced into the C-2 position of octenoyl-CoA. 3) The reduction occurred by an anti-addition of hydrogen via a 2-Si, 3-Re attack on the cis-double bond.
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HIROTERU SAYO, MIKIO HOSOKAWA
1982 Volume 30 Issue 6 Pages
2161-2168
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The kinetic mechanism of the ethyl hydroperoxide (EHP)-and cumene hydroperoxide (CHP)-supported oxidations of aminopyrine catalyzed by catalase was investigated by the use of a stopped-flow spectrophotometer. Plots of reciprocal velocity versus the reciprocal concentration of either substrate at several different fixed concentrations of the other substrate converged to common points of intersection on the left side of the ordinate and above or below the abscissa, suggesting a sequential mechanism involving the formation of a ternary complex between catalase, aminopyrine, and EHP or CHP followed by one or more reactions and the subsequent release of the products. Potassium cyanide was a competitive inhibitor with respect to EHP and non-competitive with respect to CHP and aminopyrine. These results, which indicate that neither CHP nor aminopyrine binds directly to the heme iron, support our previous suggestion that the binding group involved in the CHP-supported oxidation of aminopyrine is different from that for the catalatic reaction.
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YORISHIGE IMAMURA, KAZUHIKO ARIMORI, MASANOBU SONODA, HISASHI ICHIBAGA ...
1982 Volume 30 Issue 6 Pages
2169-2173
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Salicylic acid reduced the in situ intestinal absorption of carbutamide, and enhanced the in situ intestinal exsorption of carbutamide. Salicylic acid, however, did not affect the in vitro intestinal absorption of carbutamide. These findings indicate that the displacement of carbutamide from its plasma protein binding sites by salicylic acid can become an important factor affecting the intestinal absorption of carbutamide in intact rabbits. Salicylic acid caused a significant increase in the apparent volume of distribution (V
αβ) and in the total body clearance (Cl
T) of carbutamide. In addition, salicylic acid was found to significantly increase the distribution of carbutamide into the pancreas and into the kidney. These findings may be explained on the basis of the displacement of carbutamide from its plasma protein binding sites by salicylic acid.
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YUSUKE TANIGAWARA, KIYOSHI YAMAOKA, TERUMICHI NAKAGAWA, TOYOZO UNO
1982 Volume 30 Issue 6 Pages
2174-2180
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Carbenicillin phenyl sodium (CFPC) and carbenicillin indanyl sodium (CIPC), which are prodrugs of carbenicillin (CBPC), were orally administered to three volunteers at various doses. The absorptions of these prodrugs were compared by means of moment analysis using urinary excretion data. CFPC showed linear absorption kinetics at 0.5, 1.0, and 1.5 g doses. On the other hand, the urinary recovery after oral administration of CIPC decreased and the mean absorption time (MAT) increased as the dose was increased from 0.5 to 1.5 g. Computer simulations by the Runge-Kutta method confirmed the occurrence of capacity-limited absorption of CIPC.
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HIROSHI FUJIWARA, SUSUMU KAWASHIMA, MASAKO OHHASHI
1982 Volume 30 Issue 6 Pages
2181-2188
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Ampicillin, buffered to pH 8.00, in the presence of benzaldehyde was found to degrade according to pseudo-first-order kinetics at 35°C, and its rate constant was smaller than that of ampicillin alone. This stabilization was assumed to be attributable to the formation of ampicillin-benzaldehyde complex. Therefore, pseudo-first-order rate constants of ampicillin in the presence of various amounts of benzaldehyde were determined. It was concluded that a 1 : 1 molar complex was formed between ampicillin and benzaldehyde, and that the reversible complexation reaction was very fast compared to the degradation reaction of ampicillin or the complex. From the degradation behavior in various concentrations of buffer at the same pH, it was clear that the stability constant of the complex was independent of buffer concentration, and that the degradation of complexed ampicillin was affected by general acidbase catalysis in the same way as that of uncomplexed ampicillin. The complexation was not observed at pH<6.00, while the degradation of ampicillin was inhibited by the addition of benzaldehyde at pH>7.00. The suppresion of the degradation of complexed ampicillin seems to be due to the inhibition of hydroxy ion attack on the β-lactam carbonyl group of the complex. Furthermore, it was shown that only the ampicillin anion (uncharged α-amino group) participates in the complexation, because the stability constant of the complex increased with increase of pH.
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HIDEO TAKENAKA, YOSHIAKI KAWASHIMA, YOSHIHIRO CHIKAMATSU, YUTAKA ANDO
1982 Volume 30 Issue 6 Pages
2189-2195
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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L-Ascorbylmonostearate was microencapsulated by a spray-drying polycondensation method with polymers such as polyvinyl alcohol, carboxymethylcellulose and polyvinylpyrrolidone, and polycondensed trimethylolmelamin trimethylether at 140°C. The particle size (1 to 10 μm) and the density (1.18 to 1.34 g/cm
3) of the microcapsules increased with increasing trimethylolmelamin trimethylether content in the formulations for spray drying. The flow curve of the ointment compounded with the microcapsules under the influence of shear exhibited a thixotropic curve with a spar. The spar value and the hysteresis loop area of the curve increased with the trimethylolmelamin trimethylether content. The amount (percent) of L-ascorbylmonostearate released from the microcapsules subjected to shear stress decreased with increasing content of trimethylolmelamin trimethylether, which might strengthen the microcapsule wall. Addition of a small amount of trimethylolmelamin trimethylether to the microcapsules imparted plastic properties to them, while the addition of an excess made the microcapsules brittle. The L-ascorbyl-monostearate release rate from the microcapsules decreased with increasing trimethylolmelamin trimethylether content in the microcapsules. The drug release rates were correlated linearly with the solubilities of the polymer films prepared on a glass plate from the same formulations as used for spray drying. Polyvinyl alcohol significantly decreased the release rate. The decomposition process of L-ascorbylmonostearate in the microcapsules dispersed in water by air-oxidation followed first-order kinetics. The decomposition rate decreased with increasing trimethylolmelamin trimethylether content in the microcapsules.
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YOSHIO TAKINO, TSUTOMU ODANI, HISAYUKI TANIZAWA, TERUAKI HAYASHI
1982 Volume 30 Issue 6 Pages
2196-2201
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Quantitative analysis of ginsenoside Rg
1, isolated from red ginseng (Panax ginseng C. A. MEYER) and one of the main saponins, was experimented in rats for the studies of the absorption, distribution, excretion and metabolism of ginseng saponins. The analysis procedure was developed as follows. Ginsenoside Rg
1 added to biological samples of rats was adsorbed on a Servachrom XAD-2 resin column after deproteinization with methanol. The adsorbed ginsenoside Rg
1 was eluted with 60% methanol aqueous solution and further subjected to thin-layer chromatography with chloroform-methanol-water (65 : 35 : 10, lower phase) as the developing solvent and 8% vanillin methanol solution/72% H
2SO
4 (1 : 5) as the detecting reagent. As reasonable recoveries and standard deviations were found in this procedure, the concentrations of ginsenoside Rg
1 in samples from rats treated with ginsenoside Rg
1 (100 mg/kg, p. o.) were determined by applying the described method.
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YOSHIKO HIRAI, JUTARO OKADA
1982 Volume 30 Issue 6 Pages
2202-2207
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The stress and strain distributions in a compressed powder bed of potassium chloride lubricated with magnesium stearate were calculated on the basis of the theory of limiting equilibrium states specified by the Mohr criterion for the axially symmetrical problems and of the stress-strain relations. The slopes of yield locus and wall yield locus for the powder bed, which were required for the calculations, were 0.426 and 0.0516, respectively. The calculated results were compared with those for an unlubricated powder bed at P
U (the upper punch pressure)=10.0kg/cm
2. More uniform distributions on the boundary surfaces and within the powder bed appeared in the present lubricated system. The stress distributions became large on the upper and lower punch surfaces as P
U increased. A region of higher stress appeared within the powder bed even at P
U=10.0kg/cm
2, and was clearer at P
U=60.0kg/cm
2.
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NORIFUMI NAKAMURA, YASUO MATSUMURA, MASANORI TAKAOKA, KATSUHIKO ITO, S ...
1982 Volume 30 Issue 6 Pages
2208-2212
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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This study was conducted to determine whether or not high molecular weight renin is present in the mouse kidney. The molecular weight of renin in the cytosol fraction of mouse kidney cortex was approximately 40000 as determined by gel filtration. Renin in this fraction was partially converted into high molecular form (54000) in the presence of sodium tetrathionate or N-ethylmaleimide, which are sulfhydryl group blockers. This high molecular weight renin was converted into regular size renin by acidification and trypsin treatment. In contrast, the molecular weight of renin in the granules was 40000, regardless of the absence or presence of sulfhydryl group blockers. Furthermore, neither change in molecular weight nor change in activity was observed after acidification. These results indicate that regular size renin is stored in the granules and may be converted into high molecular weight renin when it is released from the granules and reacts with some substance in the cytosol fraction of renal cortical tissue.
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HIROSHI KASHIWAGI, SABURO ENOMOTO
1982 Volume 30 Issue 6 Pages
2213-2218
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A new method was found for the homogeneous liquid-phase alkylation of α-, β-, and γ-picolines with either methanol or ethanol. Addition of a catalytic amount of an ammonium halide to a mixture of a picoline and an alcohol resulted in a great increase in the yields of both side-chain-and α-alkylated derivatives of the starting picoline when the reaction was carried out at 320-335°C in an atmosphere of nitrogen. The higher the reaction temperature, the greater the yields of side-chain alkylated derivatives became. In practice, this alkylation gave 2-ethylpyridine and 2, 6-lutidine from α-picoline with methanol, 3-ethylpyridine and 2, 5-lutidine from β-picoline with methanol, 4-ethylpyridine and 2, 4-lutidine from γ-picoline with methanol, 2-propylpyridine and 2-ethyl-6-methyl-pyridine from α-picoline with ethanol, 2-ethyl-5-methylpyridine from β-picoline with ethanol, and 4-propylpyridine and 2-ethyl-4-methylpyridine from γ-picoline with ethanol.
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JUZIRO NISHIJO, KUMIKO OHNO, KEIKO NISHIMURA
1982 Volume 30 Issue 6 Pages
2219-2222
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Complexation of theophylline with 4 amines having a benzene moiety was studied in water and in absolute ethanol. Theophylline forms a solid complex with benzylamine in a molar ratio of 1 : 1 from both solvents. However, no solid complex is formed between theophylline and aromatic amines, such as aniline, N-methylaniline, and N, N-dimethyl-aniline. the physico-chemical properties of the complex formed were studied by powder X-ray diffractometry, differential thermogravimetric analysis (DTA-TG), differential scanning calorimeter (DSC) and infrared spectroscopy. The DTA-TG thermograms of the solid complex obtained at a heating rate of 2.5°C/min in air showed that deamination occurred in the temperature range of 53-90°C to yield anhydrous theophylline with two endothermic peaks, a large endothermic peak followed by a broad but small endothermic peak. The reaction was first-order, and the activation energy of determination 29 kcal/mol. The heat of reaction for solid complex formation was estimated to be 21.3 kcal/mol. Hydrogen bonding was the major attractive force between the components of the complex.
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MINEO SANEYOSHI, JUNICHI TOHYAMA, CHIKAO NAKAYAMA
1982 Volume 30 Issue 6 Pages
2223-2227
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The pyrimidine 3'-deoxyriboside 5'-triphosphates, pyrimidine counterparts of cordycepin 5'-triphosphate, (1) were conveniently synthesized from cordycepin as potential deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase inhibitors. For the synthesis of 3'-deoxycytidine, p-chlororobenzoylation of 1 followed by acetolysis afforded an anomeric mixture of 1-O-acetyl-2, 5-di-O-p-chlorobenzoyl-3-deoxy-D-ribofuranose (3) in good yield. Condensation of 2, 4-bis-trimethylsilyl-N
4-acylcytosine (4a, b) with 3 in the presence of stannic chloride gave fully acylated 3'-deoxycytidine (5) in excellent yield. The protecting group was removed to give 3'-deoxycytidine (6), which on phosphorylation gave 3'-deoxycytidine 5'-monophosphate (7), a key intermediate in the present study. Deamination of 7 with nitrous acid afforded 3'-deoxycytidine-5'-monophosphate (8). Additionally, 2, 4-bis-trimethylsilyloxy-5-methyl-or ethylpyrimidine (4c, d) was coupled with 3 in a similar manner to give fully acylated 5-methyl-(5c) or 5-ethyl-3'-deoxyuridine (5d). The 5'-monophosphates were converted to the corresponding 5'-triphosphates by the phosphoroimidazolidate method.
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HIROSHI TOKUNAGA, TOSHIO KIMURA, JIRO KAWAMURA
1982 Volume 30 Issue 6 Pages
2228-2231
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A fluorometric method for the determination of cortisol (CS) in serum was established. The keto-alcohol side-chain of CS was converted to keto-aldehyde with cupric acetate, and the product was reacted with pyrrole. The relationship between the fluorescence intensity and the concentration of CS was linear in the range of 0-50 ng. This method was applied to the determination of human serum CS and the analytical data were compared with those obtained by radioimmunoassay. The regression equation for the results of the two method was y=1.29x-0.44, and the coefficient of correlation for 14 samples with CS in the range of 6.78-14.56 μg/dl was 0.967. This method gave reliable results with high specificity and sensitivity.
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YOSHIO OKAWA, KAZUHIKO HASHIMOTO, TATSUJI MATSUMOTO, SHIGEO SUZUKI, MA ...
1982 Volume 30 Issue 6 Pages
2232-2237
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A cell wall fraction of Streptoverticillium cinnamoneum, a non-pathogenic strain of Streptomycetaceae, was obtained by centrifugation of sonicated mycelia. After treatment with proteases, deoxyribonuclease, ribonuclease, and organic solvent mixture, the cell wall specimen (P-CW) was found to consist of homogeneous fibrous material when examined under an electron microscope. The survival of mice in the infection-protection assay against the Staphylococcus aureus βH 248 strain, 1.5×10
9 cells/mouse, was increased by treatment with 50mg/kg of P-CW as compared with the control group. Remarkable elevation of serum lysozyme and carbon clearance activities was observed in mice treated with the same dose of P-CW.
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HIROKO MIYOSHI, NOBUKO NAGAKANE, MARI UEMAE, KAZUO NEGISHI, HIKOYA HAY ...
1982 Volume 30 Issue 6 Pages
2238-2240
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A synergistic action of sodium bisulfite and dimethylsulfoxide on bacteriophage lambda was found. A combination of 1M sodium bisulfite, pH5, and 3% dimethylsulfoxide showed a strong phage-inactivating effect, whereas 1M sodium bisulfite alone or 3% dimethylsulfoxide alone was without effect. It was shown that both bisulfite and dimethylsulfoxide must be present simultaneously in the incubation mixture to achieve the inactivation. The phages that had been treated with a mixture of bisulfite and dimethylsulfoxide were shown to have lost their ability to transfer the viral deoxyribonucleic acid (DNA) to the host bacteria. It was also observed that a DNA sample isolated from the treated phages was fully active in transfection assay. From these results, it was concluded that the target of the reagents was the coat protein of the phage.
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KAZUYUKI KIZUKI, HIROSHI MORIYA
1982 Volume 30 Issue 6 Pages
2241-2244
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A new potent kinin-inactivating enzyme was purified from a kind of Japanese mushroom, Psalliota hortensis (Tsukuritake, in Japanese), by means of water extraction, ammonium sulfate fractionation, DEAE-Sephadex A-50 chromatography and Sephadex G-100 gel filtration. The final enzyme preparation had an activity of 2284 kininase U/E
280, which is the highest known among kininases derived from plants. This enzyme cleaved Gly
4-Phe
5 and Phe
5-Ser
6 bonds of the bradykinin molecule. Its molecular weight was estimated to be 6.7×10
4 and the optimum pH for the degradation of bradykinin was 8.0. The enzymatic activity of this enzyme was inhibited by mercurials, diisopropyl-fluorophosphate (DFP) and a high concentration of ethylenediaminetetraacetic acid (EDTA), but tosyllysine chloromethyl ketone (TLCK), tosylphenylalanine chloromethyl ketone (TPCK), iodoacetic acid, Trasylol and sodium tetrathionate had no detectable effect.
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MASAHARU UENO, TAKASHI NAKASAKI, ISAMU HORIKOSHI, NOBUO SAKURAGAWA
1982 Volume 30 Issue 6 Pages
2245-2247
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The oral administration of heparin alone or entrapped in liposomes was investigated. The prolongation of clotting time (a-PTT) was observed after administration of heparin and attributed to an increase of heparin activity in the blood as a result of effective absorption from the intestine. The increase of heparin activity was promoted by entrapping heparin in liposomes, but not by mere addition of empty liposomes.
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YASUNORI MORIMOTO, YOICHI ADACHI
1982 Volume 30 Issue 6 Pages
2248-2251
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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Liposomes composed of dipalmitoylphosphatidylcholine (DPPC) labeled with L-α-[dipalmitoyl-1-
14C]-phosphatidylcholine ([
14C]-DPPC) and cholesterol (molar ratio 7 : 2) were injected into rats intratracheally. The lungs took up about 90% of administered [
14C]-DPPC and 50% of liposomal DPPC was retained for over 24 h. In contrast, uptake by the liver and kidney after intravenous administration was high and uptake by the lung was negligible. Uptake of [
14C]-DPPC by lung lamellar bodies was higher than that by other lung subcellular fractions (mitochondria, microsomes and soluble fractions). From the results of histochemical investigation, it was found that the liposomes were taken up uniformly by the lung.
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Hideaki Umeyama, Setsuko Nakagawa
1982 Volume 30 Issue 6 Pages
2252-2254
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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The charge state of the His 57-Asp 102 couple in β-trypsin in the acid pH range was studied using the ab initio molecular orbital method. The result was in agreement with the NMR experiments which do not support the charge relay hypothesis proposed by Blow et al. It is remarkable that the charge state of His 57-Asp 102 couple is greatly affected by the environment around the catalytic triad.
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Genichiro Nonaka, Takashi Tanaka, Meiko Nita, Itsuo Nishioka
1982 Volume 30 Issue 6 Pages
2255-2257
Published: June 25, 1982
Released on J-STAGE: March 31, 2008
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A new hydrolyzable tannin, sanguiin H-6, has been isolated from the underground parts of Sanguisorba officinalis L. (rosaceae), and on the basis of spectroscopic data and partial hydrolysis study has been shown to have a novel dimeric structure containing sanguiin H-2 and pedunculagin moieties.
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