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Volume 31, Issue 7
Displaying 1-49 of 49 articles from this issue
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HIROSHI TAKAHASHI, YUJI SUZUKI, TOSHIHIKO HORI1983 Volume 31 Issue 7 Pages 2183-2191
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically pure (1S, 1'S)-1-aryl-N-2'-hydroxy-1'-isopropylethyl-1-phenylmethylamines (2a-c) were synthesized by the asymmetric reaction of (E)-(S)-N-(2-hydroxy-1-isopropylethyl) arylmethylideneamines (1a-c) with phenyllithium. On the other hand, optically pure (1R, 1'S)-configuration compounds (4a-c) were synthesized from (E)-(S)-N-(2-hydroxy-1-isopropylethyl) phenylmethylideneamine (3) and aryllithiums. Other optically pure compounds, (1R, 1'R)- and (1S, 1'R)-amines (2b and 4b), were also synthesized. The absolute configurations of these chiral amines were determined by using circular dichroism spectroscopy and X-ray analysis.View full abstractDownload PDF (767K) -
HIROKO SHIMOMURA, YUTAKA SASHIDA, KAZUNORI OGAWA, YOICHI IITAKA1983 Volume 31 Issue 7 Pages 2192-2199
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new bitter principles, ajugamarin, dihydroajugamarin, and ajugamarin chlorohydrin, which belong to the neo-clerodane group of diterpenoids, have been isolated from the leaves of Ajuga nipponensis. The structures of these compounds were established by chemical and spectroscopic means. The absolute structure of ajugamarin was determined by the X-ray analysis of ajugamarin p-bromobenzoate. Ajugamarin chlorohydrin may have been formed by addition of hydrogen chloride to ajugamarin during the isolation procedure.View full abstractDownload PDF (829K) -
TAISUKE MATSUO, HIROTOMO MASUYA, TOHRU SUGAWARA, YASUHIKO KAWANO, NORI ...1983 Volume 31 Issue 7 Pages 2200-2208
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a key intermediate for the synthesis of sulfazecin derivatives, 3-amino-3-methoxy-2-azetidinone (24 or 26) was synthesized from penicillins, and various new compounds, including sulfazecin, were synthesized by acylation and sulfonation of 24 or 26. Some of these compounds (33, 36) showed higher antibacterial activity than the corresponding 3-demethoxy derivatives against a β-lactamase-producing strain of Escherichia coli.View full abstractDownload PDF (949K) -
EMI OKUYAMA, MIKIO YAMAZAKI1983 Volume 31 Issue 7 Pages 2209-2219
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCompound B1 (tentative name), isolated from Tetragonia tetragonoides as a principle with anti-ulcerogenic activity, was determined to be a mixture of geometrical isomers of 1-O-β-D-glucopyranosyl-2-N-2'-hydroxypalmitoyl-sphinga-4, 8-dienine on the basis of chemical and spectral evidence. By repeated chromatography, compound B1 was separated into compounds B1-a (major) and B1-b (minor), which were found to be the 4-trans-8-trans and 4-trans-8-cis isomers, respectively. Several cerebrosides and glycolipids from various biological sources were examined for protective activity against the ulcer formation in mice under restraint and water immersion condition.View full abstractDownload PDF (983K) -
HAJIME KATAYAMA, YOSHIO TACHIKAWA, NORIYUKI TAKATSU, AKIRA KATO1983 Volume 31 Issue 7 Pages 2220-2233
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of mono- and dimethylation of the allyl group upon tertiary and quaternary amino-Claisen rearrangements were investigated with 1, 2, 3, 4-tetrahydroquinoline as the framework for the rearrangement. The introduction of γ-methyl onto the allyl group accelerated the rearrangement and increased the yield of para rearrangement product. The introduction of two γ-methyls on the allyl group resulted in complex reactions, of which the major ones were para rearrangement and deprenylation. Two reaction pathways, sigmatropic and dissociative, were observed. The reaction conditions used strongly influenced the products pattern. The presence of a 6-methoxy group retarded the reaction but did not have a major effect upon the reaction pattern. Tertiary and quaternary N-Claisen rearrangements are effective for the migration of allyl and crotyl groups but seem not to be very useful for the migration of the prenyl group.View full abstractDownload PDF (1452K) -
KENICHI OZAKI, YOSHIHISA YAMADA, TOYONARI OINE1983 Volume 31 Issue 7 Pages 2234-2243
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of 2-(substituted-amino) benzamide (1) with ethyl chloroformylformate (2), ethyl chloroformylacetate (3), and ethyl 2-chloroformylpropionate (4) gave 1-substituted 4 (1H)-quinazolinones (5, 6, and 7, respectively) having an ethoxycarbonyl group on the substituent at position 2. 2-Ethoxycarbonyl-1-methyl-4 (1H)-quinazolinone (5b) was converted to the carboxylic acid 14, the hydroxamic acid 16, the amide 18, and the nitrile 19. The nitrile 19 was allowed to react with various nucleophiles to give 1-methyl-4 (1H)-quinazolinones (17, 20, 21, and 22) having a substituted heteroatom at position 2. The reaction of 19 with sodium azide gave 1, 2-dihydro-4-hydroxy-1-methyl-2-(5H-tetrazol-5-ylidene)-quinazoline (25) which is the 1, 3-dipolar addition product to the cyano group. The intramolecular ring closures of 5, 6, and 7 having an alkoxycarbonylalkyl or chloroalkyl group at position 1 proceeded by using an appropriate base or heating to give the corresponding pyrrolo- or pyrido [1, 2a] quinazolinones (27, 28, 29, 31, and 32).View full abstractDownload PDF (1057K) -
TAKASHI NAKAGAWA, KOJI HAYASHI, HIROSHI MITSUHASHI1983 Volume 31 Issue 7 Pages 2244-2253
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe glycosides of the Chinese crude drug"Pai-ch'ien"("Bai-qian") were further investigated. Column chromatography of the polar portion of the crude glycosides of this drug gave three new glycosides named glaucoside-H (1), -I (2), and -J (3), and their structures were characterized on the bases of spectroscopic evidence and hydrolytic degradative studies. The structure of a new disaccharide named glaucobiose (12), formed by hydrolyses of 1, 2, and 3, was also characterized as 4-O-β-D-glucopyranosyl-L-cymaropyranose. Compounds 1 and 2 were found to correspond to 4'''-O-β-D-glucopyranosyl derivatives of glaucoside-C (4) and glaucoside-B (5) previously reported, respectively. Compound 3 is a glycoside having glaucogenin-B as the aglycone, and its sugar moiety corresponds to that of the 4'''-O-β-D-glucopyranosyl derivative of glaucoside-D (7) previously reported.View full abstractDownload PDF (1083K) -
TETSUO SEKIYA, HIDETOSHI HIRANUMA, TOSHIJI KANAYAMA, SHUNSUKE HATA, SH ...1983 Volume 31 Issue 7 Pages 2254-2261
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of our studies on pyrimidine derivatives, 27 4-alkyl-2-(1-piperazinyl)-5, 6-polymethylenepyrimidines and structurally related derivatives were synthesized, and their hypoglycemic activities were examined in mice treated with 2-deoxy-D-glucose. Most of the derivatives showed higher activity at a dose of 30 mg/kg p.o. than tolbutamide at a dose of 100 mg/kg p.o. The structure-activity relationships are discussed.View full abstractDownload PDF (778K) -
HARUYOSHI KODAIRA, MASAYUKI ISHIKAWA, YASUO KOMODA, TERUMI NAKAJIMA1983 Volume 31 Issue 7 Pages 2262-2268
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe methanol extract of the bark of Fraxinus japonica BLUME was fractionated, and by following the inhibitory activities on rat hind paw edema induced by carrageenin and on rabbit platelet aggregation induced by arachidonic acid, the following active principles were isolated and identified : 2-(3-methoxy-4-hydroxyphenyl) ethanol (I) (which also exists in animals and man as a dopamine metabolite), 2-(p-hydroxyphenyl) ethanol (II), 2, 6-dimethoxy-p-benzoquinone (III), compounds IV, V, and esculetin.View full abstractDownload PDF (842K) -
YOSHINOBU TAGAWA, NORIKO HONJO, YOSHINOBU GOTO, TAKUO CHIBA, TETSUZO K ...1983 Volume 31 Issue 7 Pages 2269-2274
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of methyl 1-oxido-2-pyridyl ketone oximes, E- (IE) and Z-forms (IZ), with tosyl chloride in the presence of NaOH were investigated to compare the reactivity of the N-oxide with that of the oxime group in the same molecule. In the reaction of IE, neighboring group participation of the N-oxide group apparently occurred, and 3-methyl-2-tosyloxy-2H-[1, 2, 5]-oxadiazolo [2, 3-a] pyridine (III) was obtained. The mechanism of the formation of III is discussed. The hydrogenation of III with H2/Pd-C afforded two 1, 2, 5-oxadiazole derivatives (IV and V) ; the hydrogenation conditions were examined in detail.View full abstractDownload PDF (589K) -
MASAFUMI SHIRAIWA, TAKAO SAKAMOTO, HIROSHI YAMANAKA1983 Volume 31 Issue 7 Pages 2275-2280
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 3-bromo-1-methoxyisoquinoline with propargyl alcohol in the presence of dichlorobis (triphenylphosphine) palladium and cuprous iodide gave 3-(1-methoxy-3-isoquinolyl) propargyl alcohol in good yield. Cyclization of 3-(1-methoxy-3-isoquinolyl) propanol obtained by the catalytic reduction of the propargyl alcohol, afforded a 1, 2, 3, 5-tetrahydropyrrolo [1, 2-b] isoquinoline derivative. The synthesis of a pyrrolo [3, 2, 1-de] phenanthridine derivative was accomplished by the introduction of an acrylic acid moiety into the pyrrolo [1, 2-b] isoquinoline and subsequent reduction and cyclization of the resulting ethyl pyrrolo [1, 2-b] isoquinoline-10-acrylate.View full abstractDownload PDF (777K) -
HIROMICHI MATSUURA, RYOJI KASAI, OSAMU TANAKA, YUHICHIRO SARUWATARI, T ...1983 Volume 31 Issue 7 Pages 2281-2287
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new saponins, named notoginsenosides-R3 (11), -R4 (12), and -R6 (13) were isolated from Sanchi-Ginseng, roots of Panax notoginseng. The structures of these saponins were established as 20 (S)-protopanaxatriol 6-O-β-D-glucopyranosyl-20-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranoside (11), 20 (S)-protopanaxadiol 3- [O-β-D-glucopyranosyl (1→2)-β-D-glucopyranosyl]-20-O-β-D-xylopyranosyl (1→6)-β-D-glucopyranosyl (1→6)-β-D-glucopyranoside (12), and 20 (S)-protopanaxatriol 6-O-β-D-glucopyranosyl-20-O-α-D-glucopyranosyl (1→6)-β-D-glucopyranoside (13), respectively. Besides these saponins, two known saponins, 20-O-glucoginsenoside-Rf (9) and gypenoside XVII (10), were also isolated and identified. From corms of this plant, ginsenosides-Rb1 (1), -Rb2 (26), -Rd (2), -Re (3), -Rg1 (4), and notoginsenoside-R1 (5) were isolated in relatively high yields.View full abstractDownload PDF (716K) -
NOBUYA KATAGIRI, AKEMI KOSHIHARA, SHUGO ATSUUMI, TETSUZO KATO1983 Volume 31 Issue 7 Pages 2288-2295
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of β-aminocrotonamide with N-acylated amino acid esters in the presence of sodium methoxide gave 2-acylaminoalkyl-6-methylpyrimidin-4 (3H)-ones, some of which, on treatment with polyphosphoric acid (PPA), were transformed into imidazo [1, 5-a] pyrimidines and imidazo [4, 5-b] pyridines.View full abstractDownload PDF (709K) -
TOHRU KIKUCHI, SATOKO MATSUDA, YOKO KUBO, TSUNEO NAMBA1983 Volume 31 Issue 7 Pages 2296-2301
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new iridoid glucosides, 8-O-(p-coumaroyl)-harpagide, 6'-O-(p-coumaroyl)-procumbide and procumboside, have been isolated from the roots of Harpagophytum procumbens DC., together with three known iridoid glucosides, harpagide, harpagoside, and procumbide. Procumboside is a novel iridoid glucoside having an ether linkage between C-3 and C-6.View full abstractDownload PDF (647K) -
SEIJI NAGUMO, MASAHIRO NAGAI, TAKAO INOUE1983 Volume 31 Issue 7 Pages 2302-2307
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo bitter principles, glucosyl pertate (I), [α]D -48.6°, and glucosyl 3α-hydroxypertate (II), [α]D -10.9°, were isolated from the leaves of Pertya glabrescens SCH. BIP. (Compositae). On acid hdrolysis, I and II yielded new sesquiterpene acids, pertic acid (IV), C15H18O4, mp152-153°C (dec.), [α]D -72.7°, and 3α-hydroxypertic acid (XI), C15H<18>O5, mp 250-252°C (dec.), [α]D +1.6°, as their genins, respectively. These genins were chemically correlated with pertilide (VI). The chemical structures of I and II were established as β-D-glucopyranosyl [1 (10) Z, 4E]-(7R, 8S)-germacra-1 (10), 4, 11 (13)-trien-12, 8-olide-14-oate (I) and β-D-glucopyranosyl [1 (10) Z, 4E]-(3R, 7R, 8S)-3-hydroxygermacra-1 (10), 4, 11 (13)-trien-12, 8-olide-14-oate (II).View full abstractDownload PDF (725K) -
CHUZO IWATA, KAZUYUKI MIYASHITA, YASUO KOGA, YASUTAKA SHINOO, MINORU Y ...1983 Volume 31 Issue 7 Pages 2308-2312
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Chamigrene (1) and a bromochamigrene derivative, 9-(Z)-bromomethylidene-1, 5, 5-trimethylspiro [5, 5] undeca-1, 7-dien-3-one (2a) were synthesized via a useful synthon in the synthesis of chamigrene-type sesquiterpenes, i.e., 1, 5, 5-trimethylspiro [5, 5] undeca-7, 10-dien-3-one (5), which had been obtained by the copper (II) chloride-catalyzed decomposition of the phenolic α-diazoketone 4.View full abstractDownload PDF (600K) -
SHIGERU OZASA, YASUHIRO FUJIOKA, HIROMI HASHINO, NAOKO KIMURA, EIICHI ...1983 Volume 31 Issue 7 Pages 2313-2320
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix polyphenyls, including four new compounds, 5', 5''-di (2-biphenylyl)-2, 2'''-diphenyl-m-quaterphenyl (3), 2, 5', 2''-triphenyl-m-terphenyl (4), 3, 5-di (2-biphenylyl)-o-terphenyl (5), and 5''-(3-biphenylyl)-m-quinquephenyl (6), were synthesized by the Ullmann coupling reaction of iodo compounds. Proton magnetic resonance spectral studies indicated that the characteristic spectral features of the polyphenyls containing 1, 3, 5-trisubstituted ring system (s) were fully compatible with their conformational aspects deduced from stereomodels. Ultraviolet spectral data indicated that the dihedral angle of the pivot bond of the branched ring in the polyphenyls in solution is very similar to that of biphenyl.View full abstractDownload PDF (841K) -
ISAO KITAGAWA, MOTOMASA KOBAYASHI, KANEYUKI KITANAKA, MASARU KIDO, YOS ...1983 Volume 31 Issue 7 Pages 2321-2328
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree peptide-like yellow compounds (1, 2, 3) containing a guanidine moiety, one of which (named hymenialdisine, 2) is a monobrominated derivative, and six 3β-hydroxymethyl-A-norsterane derivatives [purified as the acetates : 4a, 5a, 6a, 7a (a mixture of two compounds), and 8a] were isolated from the Okinawan marine sponge Hymeniacidon aldis and their structures were elucidated on the basis of physicochemical evidence including the X-ray crystallographic analysis of 2.View full abstractDownload PDF (714K) -
AKIO MIYAKE, KATSUMI ITOH, NORIO TADA, MASAO TANABE, MINORU HIRATA, YO ...1983 Volume 31 Issue 7 Pages 2329-2348
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESStrans-6-Hydroxy-2-(1-methyl-3-phenylpropyl) amino-1, 2, 3, 4-tetrahydronaphthalen-1-ol (8a), trans-6-hydroxy-2-(1-methyl-2-phenoxyethyl) amino-1, 2, 3, 4-tetrahydronaphthalen-1-ol (8b) and trans-1, 6-dihydroxy-2-(1-methyl-3-phenylpropyl) amino-1, 2, 3, 4-tetrahydronaphthalene-5-carboxamide (9a) were synthesized as a part of our search for useful cardiovascular agents. 2-(N-Substituted amino)-6-alkoxy-1, 2, 3, 4-tetrahydronaphthalen-1-ols (10-31) having various substituents at the 5-, 6- and 7-positions of the naphthalene ring were prepared by a five-step sequence of reactions starting from 3, 4-dihydro-1 (2H)-naphthalenone derivatives (36). Furthermore 2-(N-substituted amino)-1-indanol derivatives (33) and 6-(N-substituted amino)-2-hydroxy-6, 7, 8, 9-tetrahydro-5H-benzocyclohepten-5-ols (34, 35) were obtained by the reductive alkylation of the corresponding amino alcohols with carbonyl compounds. These N-substituted amino alcohols (8-35) were tested for vasodilating activity in anesthetized dogs and for β-blocking activity using isolated guinea pig atrial preparations.View full abstractDownload PDF (1452K) -
KOUKI KITAGAWA, NOBUYUKI KAWAI, YOSHIAKI KISO, TADASHI AKITA, KIYOSHI ...1983 Volume 31 Issue 7 Pages 2349-2352
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA newly isolated bovine brain pentapeptide, Thr-Ser-Lys-Tyr-Arg (neo-kyotorphin), which contains the Tyr-Arg (kyotorphin) unit at its carboxyl terminal portion, was synthesized by using the TFMSA-TFA-thioanisole deprotecting procedure. The synthetic peptide exhibited dosedependent analgesic activity in mice at a level approximately equal to that of Leu-enkephalin.View full abstractDownload PDF (542K) -
HIDEJI ITOKAWA, KAZUHIKO MIHARA, KOICHI TAKEYA1983 Volume 31 Issue 7 Pages 2353-2358
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Radix Rubiae (dried roots of Rubia cordifolia), mollugin, 1-hydroxy-2-methyl-9, 10-anthraquinone, alizarin, 1, 3-dihydroxy-2-ethoxymethyl-9, 10-anthraquinone, lucidin primeveroside, ruberythric acid and three new anthraquinones, 2-methyl-1, 3, 6-trihydroxy-9, 10-anthraquinone, 2-methyl-1, 3, 6-trihydroxy-9, 10-anthraquinone 3-O-(6'-O-acetyl)-α-rhamnosyl-(1→2)-β-glucoside and 2-methyl-1, 3, 6-trihydroxy-9, 10-anthraquinone 3-O-α-rhamnosyl (1→2)-β-glucoside, were isolated. The new anthraquinone glycosides were also obtained from the roots of R. akane, as the main chemical constituents of anthraquinone glycosides. The structures were established by various chemical and spectroscopic methods.View full abstractDownload PDF (724K) -
KAZUHIKO SAGARA, TOSHIYUKI OSHIMA, TETSUO MISAKI1983 Volume 31 Issue 7 Pages 2359-2365
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new, simple and rapid analytical method using ion-pair high-performance liquid chromatography was developed for simultaneous determination of norephedrine, pseudoephedrine, ephedrine and methylephedrine in Ephedrae Herba and oriental pharmaceutical preparations. A reversed-phase system consisting of an ODS chemically bonded silica gel column and a mixture of water, acetonitrile, sodium dodecyl sulfate and phosphoric acid (65 : 35 : 0.5 : 0.1) as the mobile phase was used. The four components extracted with the mobile phase could be completely separated within 15 min. The detection limits for the four components were 20 ng at a signal-to-noise ratio of 3 : 1.View full abstractDownload PDF (575K) -
HIROMITSU KAGEYAMA, YOUICHI OKUMURA, TETSUO ADACHI, YOSHIMASA ITO, KAZ ...1983 Volume 31 Issue 7 Pages 2366-2370
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method for the determination of urinary kallikrein activity was developed. A polystyrene bead coated with anti-human urinary kallikrein antibody was used, with prolyl-phenylalanyl-arginyl-4-methylcoumaryl-7-amide as a substrate. The proposed method is simpler, more accurate, and more specific to urinary kallikrein than the conventional method. Coefficients of variation for within-day precision and for day-to-day precision were 9.1% (n=20) and 14.4% (n=7), respectively, and recovery was 102±2.5% (n=10). The enzyme activities in urine from patients with renal failure and hypertension were lower than those in urine from normal subjects, but the activity in urine from patients with nephrotic syndrome was higher.View full abstractDownload PDF (585K) -
MACHIKO MATSUBARA, HISATORA KURODA1983 Volume 31 Issue 7 Pages 2371-2377
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structure of the polysaccharide which functions as an endogenous substrate in germinating conidia of Cochliobolus miyabeanus was studied. When the germinating conidia were extracted with 1 N NaOH, 30% KOH and 4 N acetic acid successively, the acetic acid-extractable polysaccharide (I) was the only one that decreased after the completion of germ-tube formation. Gas liquid chromatograms of the acid or enzymic hydrolysates of I and the infrared and nuclear magnetic resonance spectra of the methylated I indicated that I is composed of only β-linked glucose (β-glucan). I consists of 129 β-linked glucosyl residues which are composed of β-1, 3- and β-1, 6-linked glucosyl residues in the ratio of 5 : 2, and β-glucosyl branched units connected through C6 or C3 of the main chain glucan and non-reducing termini exist in the ratio of one residue to seven glycosyl residues.View full abstractDownload PDF (777K) -
SHINYA SHIBUTANI, TETSURO NAGASAWA, HIKOKICHI OURA, GENICHIRO NONAKA, ...1983 Volume 31 Issue 7 Pages 2378-2385
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of rhatannin (condensed tannin) purified from Rhei Rhizoma on urea nitrogen and amino acid concentrations and on the activities of various enzymes concerned with the urea cycle and amino acid metabolism in the rat were investigated. Rhatannin significantly reduced the blood urea nitrogen (BUN) concentration by 16-31% at 4-8 h after intraperitoneal administration. The reduction of BUN concentration was proportional to that of urea nitrogen concentration in the liver. The activities of five urea cycle enzymes were not affected by the administration of rhatannin. On the other hand, the concentrations of eleven amino acids (Gln, Ala, Gly, Ser, Glu, Lys, Met, Pro, Orn, Cit, Arg) in the plasma were decreased. In addition, the concentrations of three amino acids (Gln, Glu, Asp) in the liver were decreased and the Gly concentration was increased. The glutamine synthetase activity in the liver was significantly increased by 52-57% at 2-4 h, while glutamate oxaloacetate transaminase, glutamate pyruvate transaminase, glutamate dehydrogenase, and glutaminase activities were not altered. Ammonia concentration in the hepatic vein was reduced at 4-8 h prior to the reduction of ammonia concentration in the portal vein.View full abstractDownload PDF (785K) -
HIROMITSU KAGEYAMA, YOUICHI OKUMURA, TETSUO ADACHI, YOSHIMASA ITO, KAZ ...1983 Volume 31 Issue 7 Pages 2386-2394
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHuman urinary and pancreatic kallikreins were purified by immunoadsorbent column chromatography. The obtained enzymes each showed a single protein band on sodium dodecyl sulfate (SDS) polyacrylamide gel electrophoresis. The properties of the two kallikreins were compared. By both gel filtration and SDS polyacrylamide gel electrophoresis, the molecular weights of urinary and pancreatic kallikreins were estimated to be 42000±3000 and 55000±3000, respectively. The isoelectric point, pH stability and optimum pH of the two enzymes were very similar, and both enzymes were inhibited by serine protease inhibitors such as diisopropyl fluorophosphate, phenylmethyl sulfonylfluoride, aprotinin and α1-proteinase inhibitor. Both kallikreins were stable up to 56°C for 80 min at pH 8.0. Urinary and pancreatic kallikreins gave a fused precipitin line against anti-human urinary kallikrein antibody or anti-human pancreatic kallikrein antibody. The comparisons of enzymic and immunological properties thus suggested that human glandular kallikreins, at least urinary and pancreatic kallikreins, are very similar.View full abstractDownload PDF (965K) -
TSUYOSHI TANIMOTO, HIDEO FUKUDA, JIRO KAWAMURA1983 Volume 31 Issue 7 Pages 2395-2403
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour aldose reductases, designated here as aldose reductases Ia, Ib, IIa and IIb, have been purified to homogeneity from rabbit lens by a combination of several procedures such as ammonium sulfate precipitation, gel filtration, dye-affinity chromatography and chromatofocusing. The molecular weights of the four aldose reductases were estimated to be 33000 by Sephadex G-100 gel filtration, and to be 37000 by SDS-polyacrylamide gel electrophoresis. These enzymes had an identical pH optimum of 5.6. Substrate specificity studies showed that the four enzymes were capable of reducing various aldehydes and aldoses. However, D-hexoses (D-glucose and Dgalactose) were poor substrates for aldose reductases IIa and IIb. Aldose reductases Ia and Ib used both reduced nicotinamide adenine dinucleotide (NADH) and reduced nicotinamide adenine dinucleotide phosphate (NADPH) as coenzymes, but aldose reductases IIa and IIb used NADPH specifically. Very high substrate concentrations were required to demonstrate the reaction in the reverse direction with these aldose reductases. Aldose reductases Ia and Ib were activated by sulfate ion, but aldose reductases IIa and IIb were not, and they were all inhibited remarkably by phenobarbital (1 mM). On the basis of the above results, aldose reductases Ia and Ib could be classified as aldose reductase (alditol : NADP+ oxidoreductase, EC 1.1.1.21).View full abstractDownload PDF (890K) -
TARO OGISO, MASAHIRO IWAKI, MAYUMI YAMAMOTO1983 Volume 31 Issue 7 Pages 2404-2415
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hemolytic action of benzyl alcohol and its possible effect on human erythrocyte membrane have been studied. The alcohol showed a severe hemolytic action above 90-100 mM. The cells exposed to the alcohol at prelytic concentrations showed increased osmotic and heat fragility. Benzyl alcohol treatment induced a slight dissolution of the components ; phospholipids were dissolved relatively more than proteins and cholesterol. Spectrin was partly released from the membrane during incubation with the alcohol above 110 mM. Use of the spin labeling technique showed that the lipid chains became much more mobile as a result of the alcohol treatment ; the apparent rotational correlation time, tc, for probes I (12, 3) and I (1, 14) and the order parameter for I (12, 3) gradually decreased with increasing alcohol concentrations. Glucose-6-phosphate dehydrogenase activity was strongly and non-competitively inhibited by the alcohol, probably due to the extensive elution of this enzyme from the membrane. Reduced nicotinamide adenine dinucleotide (NADH) : (acceptor) oxidoreductase and Na+, K- and Mg2+-adenosine triphosphatase activities were also significantly lowered above 100-110 mM, while acetylcholine esterase activity was not significatnly inhibited. These results indicate that the alcohol above 100 mM strongly perturbs the lipid environment and membrane structure, due to greatly increased fluidity of the lipid bilayer and disordering of the lipid-protein interactions.View full abstractDownload PDF (1445K) -
KEIJI FUJIOKA, YUJI KUROSAKI, SHIGEJI SATO, TETSUO NOGUCHI, TAKESHI NO ...1983 Volume 31 Issue 7 Pages 2416-2423
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSComplexes of bencyclane fumarate (Ben) with cyclodextrins (CDs) were newly prepared and their characteristics were studied from a pharmaceutical viewpoint. The results of differential scanning calorimetry (DSC), X-ray diffractometry and thin-layer chromatography (TLC) were consistent with the formation of inclusion complexes. Water solubility of Ben-CDs were 2- to 8-fold lager than that of Ben. The stability of Ben in acidic media (pH 1.2) was considerably improved by complex formation with β-CD or γ-CD. Apparent first-order rate constants [h-1] of hydrolysis of Ben were 6.5×10-2, 5.5×10-2, 1.0×10-2 and 1.7×10-2 for Ben, Ben-α-CD, Ben-β-CD and Ben-γ-CD, respectively. The intrinsic bitter taste of Ben was significantly reduced by inclusion complexation with CDs. Thus, there are clear pharmaceutical advantages of Ben-CD compared with Ben. In addition, a novel animal test method, which is helpful for studying astringent bitter-tasting drugs, is proposed.View full abstractDownload PDF (786K) -
MASAKAZU MIZOBE, SABURO MATSUDA, TAKASHI YONEYAMA, KEIICHI KOHNO1983 Volume 31 Issue 7 Pages 2424-2431
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bioavailability of two scarcely soluble hypolipidemic compounds, 1-O-[p-(myristyloxy)-α-methylcinnamoyl] glycerol (LK-903) and its free acid (LK-A : the parent compound), was evaluated in beagle dogs by determining plasma levels by means of thin-layer chromatography (TLC) scanning densitometry. Following oral administration of LK-903, the main chemical species in plasma were acylated forms in which natural fatty acid (s) was incorporated, while unchanged and hydrolyzed forms represented minor fractions. LK-A showed very poor bioavailability in solid formulations, but exhibited plasma levels comparable to those obtained with LK-903 in solubilized formulations. Intravenous ingestion of LK-903 or LK-A resulted in no detectable transformation to the acylated forms, whereas administration of authentic sample of mono- or diacylated LK-903 produced considerable amounts of LK-903 and LK-A in the plasma, indicating the occurrence of hydrolysis in the systemic circulation. On the basis of these findings, the mechanisms of intestinal absorption were supposed to resemble that of fat absorption, in which solubilization by bile acids and transacylation in the intestinal mucosa may play important roles. In relation to these absorption mechanisms, it is possible to compare the effect of chemical modification with the glyceride moiety with that of pharmaceutical modification of the dosage form for the parent compound.View full abstractDownload PDF (706K) -
TETSUO SEKIYA, SHUNSUKE HATA, SHUNICHI YAMADA1983 Volume 31 Issue 7 Pages 2432-2437
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStructure-activity studies of 36 hypoglycemic 4-amino-2-(1-piperazinyl)-5, 6-polymethylenepyrimidine derivatives were performed by the adaptive least-squares method. In the analysis, the activity was classified into four groups. The best recognition was obtained with the following equation : L=-0.00286MW+0.241pKa+0.741 (I-4)+2.099 (I-5)+0.358 (I-6)-0.602. The number of misclassified compounds was 5, and the Spearman rank correlation coefficient was 0.921. In the equation, MW is molecular weight, and pKa stands for the basicity of the piperazinyl group. The indicator variables I-4, I-5, and I-6 are assigned a value of 1 when the 4-acylated 1-piperazinyl group (not including 4-acryloyl-1-piperazinyl group), 4-acryloyl-1-piperazinyl group and any group having an >NCH2CH2O- structure are present, respectively. From the equation, it was concluded that the 2-(1-piperazinyl) pyrimidine moiety is an essential structure for the activity, and the basicity of the 1-piperazinyl group is also important. The structure-activity relationships are analyzed and discussed in detail.View full abstractDownload PDF (545K) -
MINEZO OTSUKA, TADAO KUROZUMI, SATOSHI FURUUCHI, SATOSHI USUKI, KEISHI ...1983 Volume 31 Issue 7 Pages 2438-2450
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolism of afloqualone (6-amino-2-fluoromethyl-3-(o-tolyl)-4 (3H)-quinazolinone, AFQ) was studied in rats. AFQ was extensively metabolized by rats after oral administration of 3H-AFQ. Thirteen unconjugated and three conjugated metabolites were isolated from the 24-h urine. Their chemical structures were identified or characterized by infrared (IR), nuclear magnetic resonance (NMR) and mass spectrometry in comparison with synthetic samples. One of the major metabolic pathways of AFQ was acetylation at the 6-amino group followed by hydroxylation of the methyl carbons of the acetyl and 2'-methyl groups. Another important metabolic pathway was the formation of sulfur-containing metabolites in which the fluorine atom at the 2-position of AFQ is replaced by a methylsulfinyl or methylsulfonyl group. These metabolites may be formed via the mercapturic acid conjugate (s) of AFQ. Five metabolites were detected in plasma 1 h after oral administration. They were the N-acetylated and hydroxylated metabolites ; the sulfur-containing metabolites found in the urine were not detected in plasma.View full abstractDownload PDF (1170K) -
KENICHI SASAKI, SHINOBU FURUSAWA, KEIKO MONMA, GIICHI TAKAYANAGI1983 Volume 31 Issue 7 Pages 2451-2458
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of chlordiazepoxide, diazepam and oxazepam administration on the antitumor activity, acute toxicity and metabolism of tegafur were investigated in mice and compared with those in the case of 5-fluorouracil (5-FU). Tegafur was administered 24 h after the final injection of chlordiazepoxide, diazepam or oxazepam (100 mg kg-1·d-1 for 3d, i.p.). The pretreatment with these drugs increased the antitumor activity of tegafur against the solid form of Sarcoma 180 and the acute toxicity. In chlordiazepoxide-, diazepam- or oxazepam-treated mice, after the administration of tegafur, the level of tegafur in the plasma was lower than that in untreated mice and a large amount of 5-FU was released. A low level of 5-FU in the plasma after the administration of 5-FU was also observed in chlordiazepoxide-, diazepam- or oxazepam-treated mice. In the liver and kidneys of chlordiazepoxide-, diazepam-, or oxazepam-treated mice, the level of 5-FU after the administration of tegafur was higher. On the other hand, chlordiazepoxide, diazepam or oxazepam significantly enhanced the activities of hepatic drug-metabolizing enzymes. It can therefore be presumed that the antitumor activity of tegafur was enhanced by chlordiazepoxide, diazepam or oxazepam as a result of promotion of the conversion of tegafur to 5-FU, mainly via the induction of hepatic drug-metabolizing activities.View full abstractDownload PDF (808K) -
SHOJI KOJIMA, MASAMI HIRAI, MORIO KIYOZUMI, YUMIKO SASAWA, MITSUO NAKA ...1983 Volume 31 Issue 7 Pages 2459-2465
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolic fate of manganese after the oral administration of excessive manganese chloride in rats was studied. After a single oral administration of manganese chloride (100 mg Mn/kg), the manganese levels in most tissues temporarily increased and then rapidly decreased to the control values within 24-48 h ; however, the manganese levels in the pancreas, brain, and bone were considerably higher than the control values even at 48 h after the administration. The tissue levels of manganese in rats given a single oral administration of 200 or 400mg Mn/kg were markedly higher than those after 100mg/kg and remained much higher than the control and 100 mg Mn/kg values at 24 h after the administration. The increase in the tissue retention of manganese at such high doses was found to be due to a decrease in the biliary excretion of manganese, which is the major excretion route of the metal. On the other hand, when manganese (100mg Mn/kg) was given every other day for three months, little tissue accumulation of manganese was observed in rats.View full abstractDownload PDF (705K) -
MASAHIKO IKEKITA, KAZUYUKI KIZUKI, HIROSHI MORIYA1983 Volume 31 Issue 7 Pages 2466-2472
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe immunological properties of various forms of pancreatic kallikreins, i.e., kallikreins A and B, and asialo-kallikreins A and B, submaxillary kallikrein, renal kallikrein and intestinal kallikrein from hog were studied by immunodiffusion and immunoelectrophoresis techniques to investigate their immunological relationships. The immunological assay showed that there is cross-reaction among the various forms of hog pancreatic kallikreins and other hog glandular kallikreins (submaxillary, renal and intestinal kallikreins) but there is no cross-reaction with either pancreatic kallikreins of other species (dog, rat and human) or human urinary kallikrein (HUK) against rabbit anti-hog pancreatic kallikrein A serum and anti-B serum. The only significant differences observed were in the electrophoretic mobilities of the various forms of hog pancreatic kallikreins and other hog glandular kallikreins under the same conditions of immunoelectrophoresis. In the case of hog pancreatic kallikreins A and B, it could be assumed that the different electrophoretic mobilities of these heterogeneous forms are not mainly due to differences in the amounts of sialic acid residues of these kallikreins. Rabbit anti-HUK serum recognized human glandular kallikreins (pancreatic, salivary and urinary kallikreins), but this antiserum did not react completely with hog pancreatic kallikrein. The implications of this are discussed.View full abstractDownload PDF (1453K) -
MITSURU FURUKAWA, KIMIMASA KAWANABE, ATSUKO YOSHIMI, TADASHI OKAWARA, ...1983 Volume 31 Issue 7 Pages 2473-2479
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSArylbiguanide (1) and 2-guanidinobenzimidazole (2) were reacted with diethyl azodicarboxylate (3) to give dihydro-s-triazine (6) and dihydrobenzimidazo [1, 2-a]-s-triazine (9), respectively. The reactions of 1 and 2 with dimethyl acetylenedicarboxylate (4) in alcohol provided the corresponding imidazolinylideneacetylguanidines (10 and 12), which were converted to alkyl imidazolidinylideneacetates (11 and 13) by alcoholysis. The compounds 10 and 12 underwent acid-catalyzed ring conversion to pyrimidine compounds (15 and 16).View full abstractDownload PDF (621K) -
TAKUO CHIBA, HIROTOSHI SATO, TETSUZO KATO1983 Volume 31 Issue 7 Pages 2480-2483
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of ethyl 4-bromoacetoacetate (1) with 2-cyanoethene-1, 1-dithiol derivatives (prepared from carbon disulfide and active methylene compounds such as ethyl cyanoacetate and malononitrile in the presence of sodium hydride) gave 2-substituted 4-hydroxy-1, 3-dithiolane-4-acetates, 2a and 2b. On the other hand, reaction of 1 with 2-cyano-1-methylthioethene-1-thiol derivatives (prepared from 2-cyanoethene-1, 1-dithiol derivatives and methyl iodide) gave 4-substituted 3-amino-5-methylthiothiophene-2-(3-oxo) propionates, 5a and 5b.View full abstractDownload PDF (493K) -
TAKUZO HISANO, MASANOBU TASAKI, KONOSUKE TSUMOTO, TOSHIKAZU MATSUOKA, ...1983 Volume 31 Issue 7 Pages 2484-2490
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of N1-(substituted phenyl) pyridinecarboxamidines was synthesized by the condensation of substituted anilines with cyanopyridines in the presence of aluminum chloride or sodium amide and these compounds were evaluated for antiinflammatory activity by the carrageenin-induced rat paw edema assay. In the synthesis of N1-alkoxyphenyl pyridinecarboxamidines, it was found that o-alkoxyanilines reacted with aluminum chloride to afford o-aminophenol, while m- and p-alkoxyanilines were scarcely dealkylated. Sodium amide was successfully used for the condensation of o-alkoxyanilines with cyanopyridines. Among several active derivatives, N1-(2, 4-dichlorophenyl) pyridinecarboxamidine and N1-(4-chlorophenyl)-pyridinecarboxamidine exhibited significant antiinflammatory activities.View full abstractDownload PDF (660K) -
HIDEJI ITOKAWA, RITSUO AIYAMA, AKIRA IKUTA1983 Volume 31 Issue 7 Pages 2491-2496
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of correlating pungency with substituent groups on one benzene ring, various analogues of yakuchinones were synthesized by means of the Claisen-Schmidt reaction. Their pungencies were assessed by direct comparison of the threshold concentrations obtained in taste experiments. The presence of a phenolic hydroxyl group was indispensable for high pungency, while that of a 1, 2-double bond of the heptanone part tended to decrease the pungency.View full abstractDownload PDF (629K) -
YOSHIYUKI KIMURA, HIROMICHI OKUDA, TAKUO OKUDA, TAKASHI YOSHIDA, TSUTO ...1983 Volume 31 Issue 7 Pages 2497-2500
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of various tannins and related compounds on the adrenaline-induced lipolysis in fat cells isolated from rats were investigated. Hydrolyzable tannins such as geraniin, corilagin, tellimagrandin I, mallotusinic acid, chebulinic acid, alnusiin and pedunculagin inhibited the adrenaline-induced lipolysis. Condensed tannins such as Ss-tannin 1 and RSF-tannin H showed weak inhibitory effects on the adrenaline-induced lipolysis. Based on these results, the relationship between the structures and physiological actions of these tannins is discussed.View full abstractDownload PDF (470K) -
YOSHIYUKI KIMURA, HIROMICHI OKUDA, TAKUO OKUDA, TAKASHI YOSHIDA, TSUTO ...1983 Volume 31 Issue 7 Pages 2501-2506
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of various tannins and related compounds on the actions of adrenocorticotropic hormone (ACTH) and insulin in fat cells isolated from rats were investigated. Hydrolyzable tannins such as geraniin, mallotusinic acid, chebulinic acid and chebulagic acid enhanced the ACTH-induced lipolysis at the concentration of 20 μg/ml or 5 μg/ml. On the other hand, these hydrolyzable tannins had no effect on the insulin-stimulated lipogenesis from glucose. Condensed tannins such as Ss-tannin 1 and RSF-tannin H showed weak inhibitory effects on the ACTH-induced lipolysis, while they enhanced the insulin-stimulated lipogenesis from glucose. Based on these results, the relationship between the structures and physiological actions of these tannins is discussed.View full abstractDownload PDF (627K) -
YOICHI SAWAYANAGI, NAOKI NAMBU, TSUNEJI NAGAI1983 Volume 31 Issue 7 Pages 2507-2509
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith a view to an application of chitin and chitosan to pharmaceutical preparations, the dissolution behavior of ground mixtures of prednisolone with chitin and chitosan was investigated. Ground mixtures of prednisolone with chitin and chitosan were prepared by cogrinding in a ball mill. The X-ray diffraction patterns and results of differential scanning calorimetry suggested that the size of crystals of prednisolone was decreased in the ground mixtures. The dissolution rate of prednisolone from the ground mixtures was significantly greater than that from the physical mixture or from intact prednisolone powder. These results indicate that chitin and chitosan can improve the dissolution properties of prednisolone.View full abstractDownload PDF (369K) -
HIROYUKI IMAIZUMI, NAOKI NAMBU, TSUNEJI NAGAI1983 Volume 31 Issue 7 Pages 2510-2512
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolid dispersion of indomethacin (IMC) in polyvinylpolypyrrolidone (PVPP), in which IMC is in an amorphous state, was prepared from an acetone solution of IMC containing PVPP in suspension, and the stability of the amorphous state of IMC dispersed in PVPP was investigated at various temperature and humidity levels in comparison with that of simple amorphous IMC. The crystallization process of IMC was investigated by powder X-ray diffractometry and differential scanning calorimetry. Without moisture, IMC dispersed in PVPP remained in the amorphous state for 6, 2 and 1 months at 40, 50, and 60°C, respectively. Simple amorphous IMC was readily converted to form I at 20, 30, 40, and 50°C in the absence of moisture. On the other hand, at relative humidity levels of 100 and 89%, IMC dispersed in PVPP was converted to form II in 7 and 28 d, respectively, at 30°C. The amorphous state of IMC was thus stabilized against heat and moisture in the solid dispersion in PVPP. This result suggests that fast-dissolving pharmaceutical preparations of IMC providing high bioavailability could be obtained by using solid dispersions in PVPP.View full abstractDownload PDF (350K) -
Stability of Solid Dosage Forms. II. Hydrolysis of Meclofenoxate Hydrochloride in Commercial TabletsSUMIE YOSHIOKA, TOSHIO SHIBAZAKI, AKIRA EJIMA1983 Volume 31 Issue 7 Pages 2513-2517
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics of hydrolysis of meclofenoxate hydrochloride (MF-HCl) in commercial tablets were studied in comparison with those of the pure solid. MF-HCl in tablets was found to be decomposed by water vapor in the same way as the pure solid. At a humidity above the critical relative humidity (CRH) of the system, the degradation ratio, x could be correlated to time by the equation x=ktn where k and n are parameters. At humidities below the CRH, on the other hand, the degradation did not conform to this equation because of the fast decomposition at the initial stage. The stability of several commercial MF-HCl tablets was studied, and some excipients such as magnesium carbonate were found to reduce the stability of the drug.View full abstractDownload PDF (525K) -
OSAMI MAKAYA, HIROSHI IRIE, JUICHIRO SHIBASAKI1983 Volume 31 Issue 7 Pages 2518-2519
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn improved synthesis of N-(butylaminocarbonyl)-4-hydroxymethyl-benzenesulfonamide, one of the metabolites of tolbutamide, and its transformation to the formyl derivative are described.View full abstractDownload PDF (357K) -
Mikio Hori, Tadashi Kataoka, Hiroshi Shimizu, Eiji Imai, Yoshinari Suz ...1983 Volume 31 Issue 7 Pages 2520-2522
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAgonistic and antagonistic properties of novel tetracyclic benzomorphans (1-4) were evaluated in vivo and in vitro opioid receptor interaction tests. Seven-membered derivatives (1, 3) showed synergism with morphine analgesia. Six-membered derivatives (2, 4) demonstrated antagonist opioid characters.View full abstractDownload PDF (386K) -
Kenichiro Nakashima, Kyoko Nakamura, Shuzo Akiyama, Taiji Ando1983 Volume 31 Issue 7 Pages 2523-2525
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA convenient method for a sensitive colorimetric determination of malondialdehyde (MDA) with 1, 3-diphenyl-2-thiobarbituric acid could be developed to apply to the determination of lipoperoxides in both rat liver and rat plasma. A linear relationship was obtained in the range of 0.12-6.25 nmol/ml of MDA. The molar absorption coefficient determined from the calibration curve was fairly large [ε=1.85×105 mol-1 dm3 cm-1]. MDA was found to be 200 nmol/g wet tissue and 1.25 nmol/ml plasma of rat.View full abstractDownload PDF (371K) -
Yasushi Okamoto, Kazunobu Harano, Masami Yasuda, Eiji Osawa, Ken Kanem ...1983 Volume 31 Issue 7 Pages 2526-2529
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe cage triketone 2 revealed different reactivities toward the thermal condition according to the substituents : the cyclobutane ring cleavage for alkyl substituents and the decarbonylation for methoxycarbonyl ones. The X-ray crystallographic study for the derivative of 2b showed a significantly long (1.635 (7) Å) C (Ph)-C (Ph) σ bond. The reaction mechanisms are discussed in terms of frontier molecular orbital (FMO) theory combined with the results of molecular mechanics and semiempirical MNDO molecular calculations.View full abstractDownload PDF (437K) -
Kazuo Masuda, Kenji Shiojima, Hiroyuki Ageta1983 Volume 31 Issue 7 Pages 2530-2533
Published: July 25, 1983
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe presence of six tetracyclic triterpenoid hydrocarbons, bacchara-12, 21-diene (1), lemmaphylla-7, 21-diene (2), shiona-3, 21-diene (3), dammara-18 (28), 21-diene (4), tirucalla-7, 21-diene (5) and eupha-7, 21-diene (6) was proved in the fresh whole plants of Lemmaphyllum microphyllum var. obovatum.View full abstractDownload PDF (459K)
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