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Volume 29, Issue 9
Displaying 1-50 of 55 articles from this issue
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HIDEKO KAWAKI, TATSUYA TAKAGI, HIDEAKI FUJIWARA, YOSHIO SASAKI1981 Volume 29 Issue 9 Pages 2397-2402
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAssociation between Eu (dpm)3 and 4-substituted acetophenones or aliphatic ketones has been investigated by measurement of the concentration dependence of 1H chemical shifts. The stoichiometry was found to be 1 : 1 by the Job method, and both the equilibrium constant K1 and the bound chemical shift Δ1 were estimated. K1 values of 4-substituted acetophenones were found to be governed predominantly by the electronic effect, whereas those of symmetrical ketones are controlled by the difference of the standard entropy ΔS° but those of nonsymmetrical ketones are not. These results can be interpreted in terms of the coordination populations of Eu (dpm)3 on the two sites of the carbonyl oxygen. The populations were obtained independently from the ratio of the geometrical factor (3cos2θ-1)/γ3 and from ΔS°, and the results were consistent with each other.View full abstractDownload PDF (531K) -
MASAZO ISHINO, TAKEICHI SAKAGUCHI, ISAO MORIMOTO, TOMOAKI OKITSU1981 Volume 29 Issue 9 Pages 2403-2407
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe protonation sites of adenine N-3 derivatives in dimethyl sulfoxide (DMSO)-d6 were investigated on the basis of proton nuclear magnetic resonance (PMR) and carbon-13 nuclear magnetic resonance (13C NMR) spectral measurements. The spectra of the protonated and non-protonated adenine N-3 derivatives showed that, upon protonation : 1) the chemical shift of the H-8 proton moved further downfield than that of the H-2 proton, and 2) the signal of NH2 protons was split into a doublet at 30°C and showed a broad line at 70°C, and 3) the signal of the C-5 carbon moved further upfield than that of the C-4 carbon. The findings indicate that adenine N-3 derivatives are protonated at the N-7 site.View full abstractDownload PDF (579K) -
MORIO IKEHARA, JUNKO IMURA1981 Volume 29 Issue 9 Pages 2408-2412
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2'-Deoxy-2'-fluoroguanylyl-(3'-5')-uridine (GfpU) was synthesized as a non-hydrolyzable substrate analog of ribonuclease T1. 2'-Deoxy-2'-fluoroguanosine was derivatized to the N2-isobutyryl-5'-monomethoxytrityl compound and condensed with 2', 3'-di-O-acetyluridine 5'-monophosphate by the use of dicyclohexylcarbodiimide to obtain GfpU. For structural elucidation of the dinucleoside monophosphate, 2'-deoxy-2'-fluoroguanosine 3'-monophosphate was also synthesized. The conformation of GfpU was found to take a right-handed, weakly stacked form as deduced by ultraviolet, circular dichroism, and nuclear magnetic resonance (NMR) spectroscopy.View full abstractDownload PDF (609K) -
TOMOKO SHOMURA, SAWAKO SOMEYA, SHINJIRO MURATA, KOSHIRO UMEMURA, MOTOH ...1981 Volume 29 Issue 9 Pages 2413-2419
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of several metabolites of 9, 3"-diacetylmidecamycin were studied by means of nuclear magnetic resonance (NMR) and mass spectroscopy. It was shown that these metabolites are a pair of 14-hydroxylated compounds which differ in the stereochemistry at carbon-14 of the macrocyclic lactone ring, and the corresponding 9-de-acetylated products.View full abstractDownload PDF (641K) -
KENICHI YAKUSHIJIN, MASAMICHI KOZUKA, TAKAYUKI MORISHITA, HIROSHI FURU ...1981 Volume 29 Issue 9 Pages 2420-2430
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the ring transformation of 2-furylcarbamates (2) to 5-hydroxy-3-pyrrolin-2-ones (3) by irradiation in the presence of oxygen, there is an equilibrium between N-carbobenzyloxy-5-hydroxy-5-phenyl-3-pyrrolin-2-one (3-A) and cis-γ-ketoamide (3-B) ; this equilibrium was studied by nuclear magnetic resonance spectroscopy. The presence of electron-withdrawing groups in the benzene ring selectively stabilized the hydroxypyrrolinone tautomer, while that of electron-releasing groups had the opposite effect. These results indicate that the ring-chain tautomerism depends on the electronic and/or steric factors of substituents on the benzene ring.View full abstractDownload PDF (887K) -
SEIICHI SAKUMA, JUNZO SHOJI1981 Volume 29 Issue 9 Pages 2431-2441
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven triterpenoidal saponins, onjisaponins A, B, C, D, E, F, and G, were isolated from the roots of Polygala tenuifolia WILLDENOW. Among these saponins, the structures of onjisaponins G (1) and F (2) were determined on the basis of spectral and chemical evidence as presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-{[β-D-apio-D-furanosyl (1→3)]-[β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside and presenegenin-(3)-β-D-glucopyranosido-(28)-2-O-{[β-D-apio-D-furanosyl-(1→3)] [α-L-arabinopyranosyl (1→3)-β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl}-4-O-(3', 4', 5'-trimethoxycinnamoyl)-β-D-fucopyranoside, respectively.View full abstractDownload PDF (1276K) -
KATSUHIDE MATOBA, KENICHI ITOH, KAKUYA KONDO, TAKAO YAMAZAKI, MASANORI ...1981 Volume 29 Issue 9 Pages 2442-2450
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-(2-Furfurylidene) acetylquinoxaline (Ia) and its 3-methyl analog (Ib) were cyclized to pyrrolo [1, 2-α] quinoxaline ring systems (IIa and IIb) by hydrochloric acid treatment. 2-(4-Methoxybenzylidene) acetylpyridine could be cyclized directly to the 2, 3-dihydroindolizine ring system (V) by treatment with perchloric acid. 2-Arylideneacetyl-3-methyl-quinoxalines (IX) also were cyclized to the corresponding pyrrolo [1, 2-α] quinoxaline systems by hydrochloric acid or perchloric acid. The cyclization of 2-(2-furfurylidene)-acetylquinoline (XI) was performed by using acetic anhydride in the presence of a catalytic amount of trifluoroacetic acid. 2-(2-Furfurylidene) acetylpyrazine (XIII) was cyclized easily by hydrochloric acid treatment. The structures of the adducts of these cyclic products with dimethyl acetylenedicarboxylate are discussed.View full abstractDownload PDF (1028K) -
TOSHIHIRO NOHARA, YOSHIKI KASHIWADA, KOTARO MURAKAMI, TOSHIAKI TOMIMAT ...1981 Volume 29 Issue 9 Pages 2451-2459
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of cinncassiol D1 (1), cinncassiol D1 glucoside (2), cinncassiol D2 (3), cinncassiol D2 glucoside (4) and cinncassiol D3 (5), isolated from the fraction exhibiting anti-complement activity of the water extractive of Cinnamomi Cortex ("Toko Keihi"), have been characterized by means of chemical, spectral and X-ray analyses. They are novel pentacyclic diterpenes with a new skeleton.View full abstractDownload PDF (904K) -
YASUMITSU TAMURA, CHING LING CHEN, MASANOBU FUJITA, HIROSHI KIYOKAWA, ...1981 Volume 29 Issue 9 Pages 2460-2464
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 7-aza analog (1·HCl) of 5-(3-tert-butylamino-2-hydroxy) propoxy-3, 4-dihydrocarbostyril·hydrochloride (2·HCl, carteolol·HCl) was prepared as part of a search for new adrenergic receptor antagonists. Thermal treatment of 1-acetyl-3-benzylamino-5-oxo-3, 4-dehydropiperidine (3), derived from N-acetylpiperidine-3, 5-dione (4a) by treatment with acryloyl chloride, gave 7-acetyl-1-benzyl-2, 5-dioxo-1, 2, 3, 4, 5, 6, 7, 8-octahydro-1, 7-naphthyridine (7). Dehydrogenation of 7 on 5% palladium carbon, and subsequent reductive debenzylation with liquid ammonia and sodium gave 5-hydroxy-1, 2, 3, 4-tetrahydro-2-oxo-1, 7-naphthyridine (5). Alkylation of 5 with epichlorohydrin, treatment with alkali and amination with tert-butylamine gave 5-(3-tert-butylamino-2-hydroxy)-propoxy-1, 2, 3, 4-tetrahydro-2-oxo-1, 7-naphthyridine·hydrochloride (1·HCl) in 45% overall yield from 5.View full abstractDownload PDF (591K) -
HAJIME KATAYAMA, NORIYUKI TAKATSU1981 Volume 29 Issue 9 Pages 2465-2477
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAmino (N)-Claisen rearrangement of quaternary aniline derivatives with ortho substituents was investigated in relation to that of corresponding tertiary anilines. N-Allylated anilinium compounds 1 with a freely rotating ortho substituent such as a methyl or methoxy group yielded mostly the deallylated products 4 along with minor amounts of rearrangement products 2 and 3. The corresponding tertiary anilines yielded ortho rearrangement products 6 together with para ones 7. The quaternary N-Claisen rearangement of N-allylated 1, 2, 3, 4-tetrahydroquinolinium salts 14 and indolinium salts 22 in which the ortho substituents are locked in rings afforded the ortho rearrangement products 15 and 23, respectively in good yields. N-Claisen rearrangement of the corresponding aromatic tertiary amines 18 also took place in good yield. The above rearrangements could be rationalized on the basis of mechanistic considerations.View full abstractDownload PDF (1410K) -
Synthesis and Stereochemistry of the Metabolites of 2α-Cyano-4α, 5α-epoxy-17β-hydroxyandrostan-3-oneYUJI MORI, MAKOTO TSUBOI, MAKOTO SUZUKI1981 Volume 29 Issue 9 Pages 2478-2484
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe preparation of the metabolites of 2α-cyano-4α, 5α-epoxy-17β-hydroxyandrostan-3-one (trilostane) is described, including a novel oxidation with pyridinium chlorochromate. Pyridinium chlorochromate oxidation of trilostane gave the α, β-unsaturated cyanoketone (2), which was hydrogenated to yield metabolite M-1 (3). The compound 3 was converted to the cyano-acetates (11), (12), and (13) and their stereochemistries were established by nuclear magnetic resonance analysis. The cyano-acetate (11) was transformed into M-3 triacetate via M-2 diacetate by successive enol acetylation, epoxidation, acid-catalyzed rearrangement, reduction, and acetylation. The metabolites M-2 and M-3 were established to have the structures 2α-cyano-3α, 16α-dihydroxy-4α, 5α-epoxyandrostan-17-one and 2α-cyano-4α, 5α-epoxy-3α, 16α, -17β-trihydroxyandrostane, respectively.View full abstractDownload PDF (805K) -
TAKAO SAKAMOTO, TAKEJI SAKASAI, HIROSHI YAMANAKA1981 Volume 29 Issue 9 Pages 2485-2490
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidation of 2, 4-dimethylquinoline and its 1-oxide with an equimolecular amount of selenium dioxide in boiling dioxane afforded 4-methylquinoline-2-carbaldehyde and its 1-oxide, respectively. This oxidation was applicable to the selective preparation of pyrimidine-4-carbaldehydes from dimethylpyrimidines. In case of pyrimidine derivatives, the presence of an N-oxide group facilitated the oxidation, but the isolated yields of the pyrimidinecarbaldehyde N-oxides were unsatisfactory, because of their instability.View full abstractDownload PDF (690K) -
KOOHEI NOZAWA, MIKIKO YAMADA, YOSHIKO TSUDA, KENICHI KAWAI, SHOICHI NA ...1981 Volume 29 Issue 9 Pages 2491-2495
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious 3-arylisocoumarins (5, 6, 8, 10, 11, and 12) were simply prepared in high yields by heating homophthalic acids (1-4) with aromatic acyl chlorides. 8-Hydroxy-3-phenylisocoumarin (17) and 8-acetoxy-3-phenylisocoumarin (18), and 8-hydroxy-3-(p-methoxyphenyl) isocoumarin (19) were obtained by alkaline hydrolysis of 10 and 11, respectively, followed by treatment with acetic anhydride. 3, 4-Dihydro-8-hydroxy-3-phenyl-isocoumarin (24) was prepared from 10 by alkaline hydrolysis followed by reduction with sodium borohydride then heating with acetic anhydride. 3-(p-Hydroxyphenyl)-isocoumarin (7), 8-hydroxy-3-(p-hydroxyphenyl) isocoumarin (9), 5-chloro-8-hydroxy-6-methoxy-3-phenylisocoumarin (13), and 3, 4-dihydro-3-(p-hydroxyphenyl) isocoumarin (23) were prepared by demethylation of 6, 8, 12 and 22, respectively. All the prepared isocoumarins and some other isocoumarin derivatives (25-30) were examined in vitro for antifungal activity. The structure-activity relationships are discussed.View full abstractDownload PDF (582K) -
YOSHIHARU ISHIKAWA, YASUO KUREBAYASHI, KUNIO SUZUKI, YOSHIYASU TERAO, ...1981 Volume 29 Issue 9 Pages 2496-2502
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present paper describes novel rearrangements of α-N-alkylamido-substituted sulfides and sulfones promoted by strong bases such as NaH, lithium diisopropylamide and butyllithium, where the alkyl group linked to the sulfur migrates to the amide carbonyl carbon to give the corresponding ketones. The reactions are established as intramolecular rearrangements, and the mechanism is discussed.View full abstractDownload PDF (662K) -
TOZO FUJII, TAKASHI HIRAGA, MASASHI OHBA1981 Volume 29 Issue 9 Pages 2503-2508
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the oxidation of 3-substituted 1-methylpyridinium salts (type III) with potassium ferricyanide and KOH at 32°C, the isopropyl and the tert-butyl group at the 3-position were found to orient oxidation to both the 2-(type IV) and the 6-position (type V) in ratios of 71 : 29 and 14 : 86, respectively. In the oxidation of the 1-methyl-3-tert-butyl-pyridinium salt (IIIl), replacement of the 1-methyl group by an aralkyl group along the series benzyl, phenethyl, and 3, 4-dimethoxyphenethyl decreased the extent of the 2-pyridone formation along the series.View full abstractDownload PDF (675K) -
KENJI TSUJIHARA, MASAKATSU OZEKI, TAMIO MORIKAWA, YOSHIHISA ARAI1981 Volume 29 Issue 9 Pages 2509-2515
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(2-Chloroethyl)-3, 3-disubstituted-1-nitrosoureas (5a-m), a new class of nitrosoureas, were synthesized and tested for antitumor activities against leukemia L1210 and Ehrlich ascites carcinoma. The nitrosoureas (5e-k) having a hydroxyl group at the β-position of the substituents showed remarkable antitumor activities. In particular, 1-(2-chloroethyl)-3, 3-bis (2-hydroxyethyl)-1-nitrosourea (5k) had excellent activities and showed 5 and 16 times greater therapeutic ratios than 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea against leukemia L1210 and Ehrlich ascites carcinoma, respectively. These nitrosoureas (5e-k) appear to be activated nonenzymatically by attack of the hydroxyl group on the carbonyl group to give the oxazolidinones (6) and chloroethyl diazohydroxide (7) without generation of the isocyanates (8).View full abstractDownload PDF (827K) -
CHOJI KASHIMA, AKIRA KATOH, YUKO YOKOTA, YOSHIMORI OMOTE1981 Volume 29 Issue 9 Pages 2516-2519
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 4, 6-Trisubstituted 2 (1H)-pyrimidinones (Ia-e) underwent ring transformation with hydroxylamine to afford 3, 5-disubstituted isoxazoles (IIa-e) in high yields. On the other hand, 2 (1H)-pyrimidinethiones (IIIa, b, f-k) underwent ring transformation to give mainly a new type of N-substituted 2-aminopyrimidine 1-oxides (IVa, b, f-k) as well as isoxazoles. The reaction of pyrimidinium salts (VII, VIII and IX) with hydroxylamine is also discussed.View full abstractDownload PDF (506K) -
TAKUSHI KURIHARA, KEIKO NASU1981 Volume 29 Issue 9 Pages 2520-2525
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNucleophilic additions of phenol analogs, indoles, and enamines of cyclohexanone to 6, 7-dicarbethoxypyrazolo [1, 5-α] pyrimidine-3-carbonitrile (1) in the presence of boron trifluoride etherate are described. For example, though phenol or o-cresol (having no substituent at the para-position) reacted with 1 to give cyclohexadienylidene derivatives (3, 4), p-cresol or p-methoxyphenol gave the spiro {benzofuran-3 (2H), 7'(4'H)-pyrazolo-[1, 5-α] pyrimidine} compounds (6, 7) upon reaction with 1. Indoles reacted with 1 to give the 7-indolyl derivatives (11, 12). When 1 was treated with enamines of cyclohexanone in the presence of a slight excess of boron trifluoride etherate, 7-(2-amino-1-cyclohexenyl) pyrazolo [1, 5-α] pyrimidines (13, 14) were obtained as their boron trifluoride complexes in good yields.View full abstractDownload PDF (677K) -
HIROKI TAKAHATA, AKIRA TOMOGUCHI, TAKAO YAMAZAKI1981 Volume 29 Issue 9 Pages 2526-2530
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of a cyclic β-aminoester such as 2-ethoxycarbonylmethylpiperidine (5) with the lactim thioethers 1b and 1c gave a 10-membered cyclic diamide (7) and an 11-membered ring compound (9), respectively. On the other hand, though acyclic β-aminoesters (6) reacted with 1 to afford methyl 3-methylthiopropionate (11), N-alkyl 3-methylthiopropionamide (12), lactams (13), and amidines (14), no cyclic diamide was obtained.View full abstractDownload PDF (536K) -
TOHRU KIKUCHI, TOSHIO YOKOI, TETSURO SHINGU, MINEO NIWA1981 Volume 29 Issue 9 Pages 2531-2539
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo novel-type triterpenes, pachysandienol-A and -B, were isolated from Pachysandra terminalis SIEB. et ZUCC., and were proved to have the structures Ia and IIa, respectively, by means of chemical and spectroscopic studies. Ia and IIa are the first examples among natural products of 28-nor-16-methyl-friedelane derivatives.View full abstractDownload PDF (851K) -
ISAO KITAGAWA, HIROTAKA SHIBUYA, HIROMICHI FUJIOKA, AKIHARU KAJIWARA, ...1981 Volume 29 Issue 9 Pages 2540-2547
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a series of studies on the transformation of terpenoids, four 1, 2, 2-trimethyl-cyclopentane derivatives, i.e., (+)-(1S, 3S)-3-acetoxymethyl-1, 2, 2-trimethyl-1-vinylcyclopentane (5), (+)-(1S, 3S)-3-acetoxymethyl-1-(3'-hydroxypropenyl)-1, 2, 2-trimethylcyclopentane (7), (+)-(1R, 3S, 1'S)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-1, 2, 2-trimethylcyclopentane (8), and (+)-(1R, 3S, 1'R)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-1, 2, 2-trimethylcyclopentane (9), were synthesized from d-camphor (1) via d-camphoric acid (2). All four compounds (5, 7, 8, 9) retain the C-4 configuration of d-camphor at their C-3 positions.View full abstractDownload PDF (940K) -
ISAO KITAGAWA, HIROTAKA SHIBUYA, HIROMICHI FUJIOKA, AKIHARU KAJIWARA, ...1981 Volume 29 Issue 9 Pages 2548-2556
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour 1, 2, 2-trimethylcyclopentane derivatives, (+)-(1S, 3S)-3-acetoxymethyl-1, 2, 2-trimethyl-1-vinylcyclopentane (3), (+)-(1S, 3S)-3-acetoxymethyl-1-(3'-hydroxypropenyl)-1, 2, 2-trimethylcyclopentane (4), (+)-(1R, 3S, 1'S)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-1, 2, 2-trimethylcyclopentane (5), and (+)-(1R, 3S, 1'R)-3-acetoxymethyl-1-(1', 2'-epoxyethyl)-1, 2, 2-trimethylcyclopentane (6), which were synthesized from d-camphor (1), were subjected to acid treatment. It was found that i) treatment of 3 with 2, 4, 4, 6-tetrabromocyclohexa-2, 5-dienone yielded a cyclohexane derivative (7) which was formed via a ringenlargement reaction sequence, ii) BF3-etherate treatment of 5 furnished three cyclopentane derivatives (14, 15, 16), among which 14 and 15 possess a 2-oxa-bicyclo [3.3.0]-octane skeleton produced through successive migrations of methyl groups, and iii) BF3-etherate or titanium tetrachloride treatment of 6 resulted in a ring-enlargement reaction giving 19 and 20, or 21.View full abstractDownload PDF (955K) -
YOSHIHIRO HARIGAYA, KOKO YOTSUMOTO, SEIKO TAKAMATSU, HIROKO YAMAGUCHI, ...1981 Volume 29 Issue 9 Pages 2557-2564
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe naphthoquinone epoxide (4), derived from the naphthoquinone (1), is reduced with sodium borohydride under mild conditions to yield the cis-epoxy ketol (5) exclusively. The configuration of the 4-hydroxyl group in 5 is deduced on the basis of the intramolecular hydrogen-bonding observed in the infrared spectrum. Further reduction of 5 with sodium borohydride gives the cis-epoxyhydroxy lactone (7) as a main product, which is stereoselectively converted into the 10b-hydroxychelidonine (17) and 4b-epichelidonine analogs (19) by the following procedures : aminolysis with methylamine (7→13), reduction with lithium aluminum hydride (13→14), hydrogenolysis over a palladium catalyst (14→17), dehydration with mesyl chloride (17→18) and reduction with lithium aluminum hydride/aluminum chloride (18→19). The stereostructures for these compounds are deduced from the infrared and proton magnetic resonance data.View full abstractDownload PDF (917K) -
KIMIYE BABA, KIYOSHI HATA, YOSHIYUKI KIMURA, YOUKO MATSUYAMA, MITSUGI ...1981 Volume 29 Issue 9 Pages 2565-2570
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dried roots of Angelica japonica A. GRAY (Umbelliferae) afforded three new chromones (VI, VIII and IX) together with six known chromones (I-V and VII) and fourteen known coumarins (X-XXIII) which were identified by comparison with authentic samples. The structure of VI, VIII and IX were established as (3S)-2, 2-dimethyl-3, 5-dihydroxy-8-hydroxymethyl-3, 4-dihydro-2H, 6H-benzo [1, 2-b : 5, 4-b'] dipyran-6-one, (3S)-2, 2-dimethyl-3-β-D-glucosyloxy-5-hydroxy-8-methyl-3, 4-dihydro-2H, 6H-benzo [1, 2-b : 5, 4-b'] dipyran-6-one (sec-O-glucosylhamaudol) and (2S)-2-(1-hydroxy-1-methylethyl)-4-methoxy-7-β-D-glucosyloxymethyl-2, 3-dihydro-5H-furo [3, 2-g] [1] benzopyran-5-one (prim-O-glucosylcimifugin).View full abstractDownload PDF (809K) -
ISAO KITAGAWA, MASAYUKI YOSHIKAWA, TOSHIYUKI KAMIGAUCHI, KIYOHARU SHIR ...1981 Volume 29 Issue 9 Pages 2571-2581
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConversions of uronic acids [e.g. methyl 2, 3, 4-tri-O-methyl-β-D-glucopyranosiduronic acid (1), D-glucuronic acid (9), and D-galacturonic acid (17)] into the corresponding aminocyclitols [e.g. 6b, 7b, 8b ; 14b, c, 15b, c, 16b, c ; 18b] have been accomplished by means of initial electrolytic decarboxylation and subsequent treatment with alkaline nitromethane, followed by catalytic reduction, and acetylation. The conversion method has also been applied to neutral sugar [e.g. D-mannose (19)] to affording L-neo-aminocyclitol hexaacetate (22b) and also to two glucuronide-saponins [sakuraso-saponin (23) and desacyl-jegosaponin (27)] to afford aminocyclitol-oligoglycosides (26a, 28a). The present electrolytic conversion is noteworthy since prior protection of hydroxyl groups in the starting uronic acids is not necessary.View full abstractDownload PDF (1207K) -
MASAYUKI YOSHIKAWA, TOSHIYUKI KAMIGAUCHI, YOSHIHARU IKEDA, ISAO KITAGA ...1981 Volume 29 Issue 9 Pages 2582-2586
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThrough a short series of reactions (catalytic oxidation, electrolytic decarboxylation, cyclization with alkaline nitromethane, and reduction), a conversion of N-acetyl-D-glucosamine (1) into hexaacetyl-streptamine (6) has been accomplished without previous protection of the hydroxyl groups in the starting compound (1), although the overall yield was not fully satisfactory. The conversion may represent a new and widely applicable means for the synthesis of diaminocyclitols from amino-sugars. A β-methoxyethoxymethyl ether function was unaffected during the anodic oxidation.View full abstractDownload PDF (685K) -
HARUAKI YAJIMA, YOSHIHARU MINAMITAKE, SUSUMU FUNAKOSHI, KENICHI AKAJI, ...1981 Volume 29 Issue 9 Pages 2587-2591
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA tridecapeptide corresponding to the entire amino acid sequence of chicken neurotensin was synthesized by applying a new deprotecting procedure with trifluoromethanesulfonic acid-thioanisole in combination with a new arginine derivative, Arg (mesitylene-2-sulfonyl). The synthetic avian neurotensin was found to be as active as synthetic bovine neurotensin in terms of contractile activity in isolated guinea-pig ileum and hypotensive effects in rats.View full abstractDownload PDF (675K) -
MITSUHIRO WAKIMASU, CHIEKO KITADA, MASAHIKO FUJINO1981 Volume 29 Issue 9 Pages 2592-2597
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe syntheses of a tridecapeptide corresponding to the amino acid sequence of dynorphin [1-13], H-Tyr-Gly-Gly-Phe-Leu-Arg-Arg-Ile-Arg-Pro-Lys-Leu-Lys-OH, and related truncated peptides, [4-13], [8-11], and [8-13], using the 4-methoxy-2, 6-dimethylbenzenesulfonyl (Mds) group for the protection of the guanidino function of arginine, are described. To synthesize dynorphin [1-13], three fragments, 1-3, 4-10, and 11-13, were prepared and used as building blocks for the final construction of the amino acid sequence of this peptide. Final deprotection of the fully protected peptide was achieved by treatment with trifluoroacetic acid-thioanisole at 50°C for 2 h and the purification of this synthetic peptide was effected by column chromatography on CM-cellulose. Other truncated peptides, [4-13], [8-11], and [8-13], were synthesized in the same manner as described for dynorphin [1-13]. The applicability of the Mds protecting group for the synthesis of arginine-containing peptides was confirmed.View full abstractDownload PDF (766K) -
HIROTERU SAYO, KOICHI MORI, TAKASHI MICHIDA1981 Volume 29 Issue 9 Pages 2598-2603
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnodic oxidation of 4'-substituted 2-nitrobenzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-H (1c), 4'-Cl (1d), 4'-COOEt (le), 4'-COCH3 (1f), 4'-NO2 (1g)) and 4'-ethoxycarbonyl-N-methyl-2-nitrobenzenesulfenanilide (1h) was investigated by cyclic voltammetry and controlled potential electrolysis at a glassy-carbon or a reticulated vitreous carbon anode in acetonitrile containing 1% trifluoroacetic acid (TFA) or 1% pyridine. The peak potentials of 1a-g in acetonitrile containing TFA were 0.23-0.55 V more positive than those in acetonitrile containing pyridine. On the other hand, the peak potential of 1h was not affected by addition of TFA or pyridine. This suggests that 1a-g partially dissociate into the sulfenamide anions in the presence of pyridine. Electrolysis of 1a, 1b, and 1d in the presence of TFA gave the corresponding 2, 7-disubstituted phenazines in higher yields than that in the absence of TFA. Although electrolysis of 1e and 1f did not give the corresponding phenazines in the absence of TFA, in the presence of TFA it did. Electrolysis of 1c and 1g did not give the corresponding phenazines in the presence or absence of TFA. Electrolysis of 1a-d in the presence of pyridine gave the corresponding pyridinated sulfenanilides, and that of 1e and 1f gave the corresponding 4, 4'-disubstituted azobenzenes. Electrolysis of 1g gave p-nitroaniline both in the absence and presence of pyridine. The variation of yields of the phenazines and species of the products was explained in terms of the extent of dissociation of the dication intermediate, which in turn depends on the 4'-substituent. The nitrenium ions and nitrenes are suggested to be intermediates in the formation of the corresponding phenazines and the primary amines, respectively. The azobenzenes are considered to be oxidation products of the primary amines.View full abstractDownload PDF (671K) -
YOSHIHIRO SATO, YOSHIKO SONODA1981 Volume 29 Issue 9 Pages 2604-2609
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCholesterol biosynthesis was examined in rat hepatic subcellular preparations (S-10) incubated with [24-3H]-lanosterol in the presence of twelve synthetic lanosterol analogs with unnatural side chains (1-12), 20-iso-24-dihydrolanosterol, 25-hydroxy-24-dihydrolanosterol, 25-hydroxycholesterol and cyclolaudenol. Cholesterol biosynthesis from 18μM [24-3H]-lanosterol was inhibited by 40μM lanosterol analogs. Among the analogs studied, 27-nordihydrolanosterol was most active in depressing cholesterol biosynthesis from lanosterol. The structure-activity relationship of lanosterol analogs and related compounds is discussed.View full abstractDownload PDF (617K) -
YOSHIYUKI KIMURA, MICHINORI KUBO, TADATO TANI, SHIGERU ARICHI, HIROMIC ...1981 Volume 29 Issue 9 Pages 2610-2617
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was found that the flavonoid components (wogonin, baicalein and baicalin) isolated from Scutellariae Radix (ogon in Japanese) inhibited lipid peroxidation in intact rat liver stimulated by the intraperitoneal administration of FeCl2-ascorbic acid-adenosine 5'-diphosphate (ADP) mixture. Various flavonoids of ogon also inhibited lipid peroxidation stimulated by FeCl2-ascorbic acid and nicotinamide adenine dinucleotide phosphate (NADPH)-ADP mixture in rat liver homogenate. Furthermore, it was found that baicalin, the major flavonoid component of ogon, reduced the increase of serum glutamic oxaloacetic transaminase (GOT) and glutamic pyruvic transaminase (GPT) levels in rats orally given an oxygen-bubbled rapeseed-corn-soybean oil mixture.View full abstractDownload PDF (774K) -
TOYOYASU KUWAE, SHIGEKI FUKASAWA, MUNETSUGU KURATA1981 Volume 29 Issue 9 Pages 2618-2623
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of Photobacterium phosphoreum PJ-1 from a luminous marine fish on the immune response of ddY mice to sheep erythrocytes (SRBC) were examined. Simultaneous intravenous injection of P.phosphoreum PJ-1 and SRBC markedly enhanced the formations of the splenic direct and indirect plaque-forming cells (PFC) against SRBC on day 7 after the immunization. The anti-SRBC hemolysin titers in sera were also markedly enhanced by the simultaneous administration of P.phosphoreum PJ-1 and SRBC, and this effect of the organism on hemolytic response to SRBC was still observed on day 34 after the immunization. The injection of P.phosphoreum PJ-1 one day after and 14 days before the immunization also significantly enhanced the splenic direct and indirect PFC responses to SRBC. In addition, the administration of P. phosphoreum PJ-1 one day before the immunization significantly enhanced only the splenic direct PFC response to SRBC. These results show that the marine bacterium P. phosphoreum PJ-1 is available as an adjuvant for studies on the immune responses to SRBC in ddY mice.View full abstractDownload PDF (522K) -
SHINJI SOEDA, ATSUO NAGAMATSU1981 Volume 29 Issue 9 Pages 2624-2630
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA procedure was developed for the purification of a tissue plasminogen activator from hog kidney. It involves six consecutive steps : (1) extraction of the tissue plasminogen activator from acetone-dried hog kidney with 0.3M potassium acetate buffer, pH 4.2 ; (2) ammonium sulfate precipitation ; (3) hydrophobic chromatography on n-butyl-Sepharose ; (4) affinity chromatography on concanavalin A-Sepharose ; (5) gel filtration on hydrophilic vinylmonomer (Toyopearl HW-55) ; (6) affinity chromatography on fibrin-Sepharose. The purified tissue plasminogen activator had an activity of 13000 IU per mg of protein as assessed by plasminogen activation and had no direct fibrinolytic activity. The apparent molecular weight of the purified tissue plasminogen activator was 60000 as estimated by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Carbohydrate analyses of the purified plasminogen activator preparation showed it to contain 54.0 μg of sialic acid and 175.0μg of hexose per mg of protein. As assessed by plasmin-catalyzed hydrolysis of D-Val-Leu-Lys-pNA, the functional activity of the purified tissue plasmigogen activator was markedly stimulated by addition of fibrin, whereas the interaction with fibrin had a slightly stimulating effect on the activity of human urokinase. Treatment with concanavalin A or glycosidases resulted in 75% or 70% loss of activity of tissue plasminogen activator, respectively, but had no effect on human urokinase.View full abstractDownload PDF (789K) -
YUTAKA KAWAZOE, MASANARI KATO, KAZUHIKO TAKAHASHI1981 Volume 29 Issue 9 Pages 2631-2638
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe treatment of E. coli B H/r 30R (wild-type) cells with alkyl isocyanates or isothiocyanates decreased the mutability of the cells under ultraviolet irradiation to an appreciable extent, whereas Hs30R (uvrA-) cells were not affected by treatment with these compounds. It is speculated that these compounds delayed the cell division, thus giving the irradiated cells a greater chance to carry out excision repair by prolonging the lag period before entering the S-phase for deoxyribonucleic acid synthesis.View full abstractDownload PDF (733K) -
TOSHIHIRO FUJII, MICHIYO KUMASAKA, YOSHIYUKI KONDO, AKIRA HACHIMORI, K ...1981 Volume 29 Issue 9 Pages 2639-2645
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTubulin from porcine brain inhibited not only the Mg-ATPase activity but also the Mg-GTPase activity of actomyosin from rabbit skeletal muscle. The inhibitory effect of tubulin on GTPase, however, was weak and a large amount of tubulin was necessary for half-maximum inhibition as compared with ATPase inhibition by tubulin. Although tubulin inhibited GTP hydrolysis by actomyosin at higher concentrations of GTP, it was found that tubulin conversely accelerated the hydrolysis of GTP at low concentrations of substrate (<0.3mM). The Km value for GTP fell from 2.5×10-3 to 1.1×10-3M upon adding tubulin. Since tubulin slightly activated myosin Mg-GTPase activity, it might block the site of actin activation. The inhibition did not seem to be competitive, because excess actin did not completely eliminate the GTPase inhibition by tubulin. The addition of KCl (at 50-100 mM) activated the GTPase activity of actomyosin, but this activation was not observed when tubulin was present. Further addition of KCl (at 200-400 mM) decreased the GTPase activity both in the presence and absence of tubulin, although the GTPase activity in the presence of tubulin was higher than that in the absence of tubulin. The extent of inhibition of GTPase by tubulin was not significantly affected by the presence of colchicine or vinblastine.View full abstractDownload PDF (748K) -
YUJI MORI, MAKOTO TSUBOI, MAKOTO SUZUKI, AKIRA SAITO, HARUO OHNISHI1981 Volume 29 Issue 9 Pages 2646-2652
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolic fate of 2α-cyano-4α, 5α-epoxy-17β-hydroxyandrostan-3-one (trilostane) in rats was studied. Five metabolites were isolated by successive column chromatography on XAD-2, LH-20, and silica gel, and they were characterized by gas chromatographymass spectrometry, nuclear magnetic resonance spectroscopy, and infrared spectroscopy. Unchanged trilostane and three metabolites, 2α-cyano-4α, 5α-epoxyandrostane-3, 17-dione (M-1), 2α-cyano-3α, 16α-dihydroxy-4α, 5α-epoxyandrostan-17-one (M-2), and 2α-cyano-4α, 5α-epoxyandrostane-3α, 16α, 17β-triol (M-3) were identified by comparison with authentic samples. Structures were tentatively assigned to the other two metabolites (M-4 and M-5). In rats given trilostane orally, unconjugated metabolites were predominantly excreted in the urine, whereas conjugated ones were excreted in the bile. On the basis of the data on biliary and urinary excretions and plasma level, the metabolic pathway of trilostane is proposed.View full abstractDownload PDF (668K) -
HIDEO TAKENAKA, YOSHIAKI KAWASHIMA, JUN HISHIDA1981 Volume 29 Issue 9 Pages 2653-2660
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe tensile strength of a powder bed of calcium carbonate moistened with aqueous solutions of surface-active agents was measured in air and in carbon tetrachloride by a diametrical compression method. The cohesive force at the point of contact of particles was determined by means of the Rumpf equation. The cohesive force determined by the diametrical compression method was much stronger than that obtained by the traction table method in air. This finding suggests that the area of contact played an important role in determining the cohesive force. When the liquid saturation ratio was less than 20%, i.e. in the pendular region, the cohesive force increased with increasing saturation ratio in both air and liquid. The cohesive force also depended on the interfacial tension of the moistening liquid, the action of which was slightly different in liquid and in air. The cohesive force was drastically decreased by rendering the particles hydrophobic. It is suggested that the cohesive force at the point of contact in the pendular region can be represented qualitatively by equation (7) in the text. H=ψf (γ) f (S) f (θ, β) (7) In the funicular region, where the liquid saturation ratio was larger than 20%, the cohesive force decreased with increasing saturation ratio. This might be due to the action of agglomerates formed in the powder bed. It was also found that the cohesive force increased with increasing interfacial tension of the moistening liquid.View full abstractDownload PDF (774K) -
HIROYUKI YOSHINO, MASAO KOBAYASHI, MASAYOSHI SAMEJIMA1981 Volume 29 Issue 9 Pages 2661-2669
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe degree of polymorphic transition of semisynthetic fatty suppository bases was estimated by means of X-ray diffraction measurements. IR values, defined as the relative intensities of two characteristic diffraction peaks of unstable A-form and stable B-form were useful for this purpose. Storage experiments using Witepsol H-15 suppositories containing 1% Brilliant Blue were performed. During storage, the changes of melting point, softening time and drug release rate were measured and compared with IR. Each of these properties showed a correlation with IR value irrespective of storage temperature or period. With lapse of time, the IR values commonly fell to a minimum in the earlier period, subsequently increased to a maximum and then remained constant. This change depended markedly on the storage temperature, so we attempted to predict the IR change using two rate parameters. One was the half-transition time t1/2 and the other was the shift factor Ar calculated by the reduced variable method. On plotting these rate parameters against 1/T, good linear relations were obtained, and the activation energies were 98 kcal and 108 kcal for t1/2 and Ar respectively. Using these values, prediction of the physical stability of the suppository seems to be possible. It was also shown that this IR method is applicable to other commercial fatty vehicles.View full abstractDownload PDF (850K) -
ICHIRO YOKOE, KYOKO HIGUCHI, YOSHIAKI SHIRATAKI, MANKI KOMATSU1981 Volume 29 Issue 9 Pages 2670-2674
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIrradiation of 2-styryl-4H-chromen-4-ones (1) with a high pressure Hg lamp at room temperature under air gave benzo [α] xanthones (2). The cyclization of methoxy-substituted styrylchromones occurred at the para position relative to the OMe group on the styryl ring, whereas 2-[β-(2-naphthyl) vinyl] chromone (3) cyclized at the α-position of the naphthalene ring.View full abstractDownload PDF (504K) -
TOYOMI SATO, AKIRA OKADA, KEIJI SEKIGUCHI, YASUYUKI TSUDA1981 Volume 29 Issue 9 Pages 2675-2682
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe noncrystalline solid form 9, 3"-diacetylmidecamycin (MOM), a new macrolide antibiotic obtained by chemical modification of midecamycin, was prepared by spraydrying and the difference in physico-chemical properties between the crystalline and noncrystalline forms was investigated. In differential scanning calorimetry (DSC) measurements, the noncrystalline solid always showed two DSC peaks in the curves ; one exothermic and the other endothermic. These are attributable to crystallization and melting, respectively. The apparent solubility of the noncrystalline solid could be determined in 0.2% hydroxypropylmethylcellulose solution but not in water and was much greater than that of the crystalline solid. When the residue during solubility measurements in water was monitored periodically by X-ray diffractometry, the noncrystalline solid was found to convert gradually to the less soluble crystalline form ; that is, the former was metastable in aqueous suspension. The conversion rate was distinctly temperature-dependent and the higher the temperature, the faster the crystallization occurred. Also, it was confirmed that the solubility of both the crystalline and the noncrystalline solid increased as the temperature was decreased. From the slopes of the van't Hoff plots, the heat of solution was estimated to be -10.9 kcal/mol for the crystalline solid and -7.3 kcal/mol for the noncrystalline solid. In addition, the appearance and the surface area of the noncrystalline solid obtained by spray-drying were examined by electron microscopy and by BET gas adsorption analysis. The spray-drying procedure increased the specific surface area to about four times that of the original crystals. It is considered that the noncrystalline MOM should have a better bioavailability than the crystalline form in vivo.View full abstractDownload PDF (975K) -
ATSUKO NODA, HIROSHI NODA, MASAO MINEMOTO, KIYOSHI ZAITSU, YOSUKE OHKU ...1981 Volume 29 Issue 9 Pages 2683-2685
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTetrazolo [5, 1-α] phthalazine (Tetra-P) was detected in the urine of a patient on hydralazine treatment. Tetra-P is a new type of monoamine oxidase (MAO) inhibitor.View full abstractDownload PDF (405K) -
YOSHIKI KASHIWADA, TOSHIHIRO NOHARA, TOSHIAKI TOMIMATSU, ITSUO NISHIOK ...1981 Volume 29 Issue 9 Pages 2686-2688
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of three novel diterpenes, cinncassiol C1 glucoside (1), cinncassiol C2 (2) and cinncassiol C3 (3), which had been isolated from the fraction exhibiting anticomplement activity of the water extractive of Cinnamomi Cortex, were characterized.View full abstractDownload PDF (474K) -
KOOHEI NOZAWA, MIKIKO YAMADA, YOSHIKO TSUDA, KENICHI KAWAI, SHOICHI NA ...1981 Volume 29 Issue 9 Pages 2689-2691
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious natural 8-hydroxyisocoumarin derivatives, i.e., oosponol (1), oospolactone (2), d-phyllodulcin (d-4) and dl-hydrangenol (dl-5), were examined for antifungal activity. Several derivatives of d-4 and dl-5 were also examined. It is very interesting that d-phyllodulcin, a sweetening component of Hydrangea serrata SERINGE var. thunbergii (Japanese name amacha), was found to possess antifungal activity.View full abstractDownload PDF (424K) -
TOZO FUJII, TAKASHI HIRAGA, MASASHI OHBA1981 Volume 29 Issue 9 Pages 2691-2695
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(3, 4-Dimethoxyphenyl)-2-(3-tert-butylpiperidino) ethanol (7) was prepared from 3-tert-butylpyridine (5) through the quaternary salt 6. The mercuric acetate-EDTA oxidation of 7 produced the 6-piperidone 10 and the 2-piperidone 13 in a ratio of 98 : 2. The former piperidone was chemically correlated with the known 6-pyridone 8 through the lactam 9, and 9 was converted into the benzoquinolizidine 11 by cyclization and reduction of the resulting iminium salt 12.View full abstractDownload PDF (656K) -
TAKAO KONOSHIMA, YASUHIRO UMEGAKI, TOKUNOSUKE SAWADA1981 Volume 29 Issue 9 Pages 2695-2699
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo triterpenoid saponins, gleditsia saponins E (GS-E) and G (GS-G), were isolated from legumes of Gleditsia japonica cv. 'Saponifera' (Leguminosae). These saponins contain monoterpene ester moieties. The desmonoterpenyl compounds, GS-E' (C69H112O34) and GS-G' (C64H104O30), were obtained from them by alkaline hydrolysis with K2CO3 and both were identified as echinocystic acid 3, 28-O-bisdesmoside on the basis of physical data and degradation products.View full abstractDownload PDF (657K) -
KATSUHIRO IMAKI, HARUKI NIWA, SHIGERU SAKUYAMA, TAKANORI OKADA, MASAAK ...1981 Volume 29 Issue 9 Pages 2699-2701
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyroglutamic acid reacted with acyl chloride in the presence of triethylamine in acetonitrile, yielding N-acylpyroglutamic acid without epimerization by way of mixed anhydride formation followed by intramolecular N-acylation.View full abstractDownload PDF (414K) -
MASAYOSHI YAMAGUCHI, MASAHIKO KOUMURA, SHOJI OKADA1981 Volume 29 Issue 9 Pages 2702-2705
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe movement of subcellular calcium in the liver was investigated after a single intraperitoneal administration of calcium chloride to bile duct-ligated rats. The hepatic mitochondrial and microsomal calcium levels significantly increased 10 min after the administration of calcium (4.0 and 15.0 mg Ca/100g body weight) to sham-operated rats, and began to decrease 30 and 60 min after that time. However, those reduction were clearly prevented by ligation of the bile duct. The administration of calcium (15.0 mg Ca/100g) to bile duct-ligated rats induced a marked accumulation of calcium in the mitochondria as compared with the microsomes. Meanwhile, the cytosolic calcium was not significantly increased by the administration of calcium (4.0 and 15.0 mg Ca/100 g). The present results suggest that the cytosolic calcium taken up by the liver cells is largely regulated by accumulation into the mitochondria and transportation into the biliary duct of rat liver.View full abstractDownload PDF (540K) -
YUKIYASU TOYODA, TADAO TAGUCHI, ICHITOMO MIWA, JUN OKUDA1981 Volume 29 Issue 9 Pages 2705-2710
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antibodies against purified rat and hog kidney mutarotases (type II) were prepared by injecting each of the purified mutarotases into rabbits and were found to quantitatively precipitate the enzyme activities of rat and hog kidney mutarotases, respectively. Immunological cross-reactivity among four forms of both rat and hog kidney mutarotases and among mutarotases from the kidney, liver, and small intestine of 5 species of animals, rat, hog, mouse, beef, and rabbit, was examined by using these antibodies. It was shown that the four forms of mutarotase in rat kidney as well as those in hog kidney were immunologically identical and that the kidney, liver, and small intestine of each species contain very similar enzymes, though there were clear differences between the enzymes from different species.View full abstractDownload PDF (942K) -
HARUHISA UEDA, TSUNEJI NAGAI1981 Volume 29 Issue 9 Pages 2710-2714
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA structural study of the inclusion compound of tolbutamide with β-cyclodextrin (β-CD) in the solid state was attempted by means of carbon-13 high resolution solid-state nuclear magnetic resonance (NMR) experiments. The change in chemical shift of tolbutamide suggested that the phenyl moiety of the drug molecule was included in the cavity of β-CD in the solid state. This view was also supported by the change of the C-H out-of-plane vibration of the phenyl moiety of tolbutamide in the Raman spectrum. The solid-state NMR technique appears to be useful for studies on the nature of inclusion compounds of drug molecules with β-CD.View full abstractDownload PDF (589K) -
SHOZO MIYAZAKI, KUNIAKI ISHII, TANEKAZU NADAI1981 Volume 29 Issue 9 Pages 2714-2717
Published: September 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthylene-vinyl acetate (EVA) copolymer was evaluated as a carrier for controlled release of prednisolone. The vinyl acetate content of EVA copolymer varied from 8 to 33% w/w. Increase in vinyl acetate comonomer content of EVA copolymer matrix brought about an increase in the release rate. The release rate could be controlled by modifying the ethylene-vinyl acetate ratio in the polymer matrix. Fabrication parameters such as matrix coating and drug content also significantly affected the release kinetics. Matrices composed of EVA copolymer could be useful vehicles for the controlled release of the corticosteroid.View full abstractDownload PDF (513K)