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Volume 36, Issue 5
Displaying 1-49 of 49 articles from this issue
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HIROSHI HARA, MASATOSHI MURAKATA, OSAMU HOSHINO, BUNSUKE UMEZAWA, YOIC ...1988 Volume 36 Issue 5 Pages 1627-1637
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid treatment of the p-quinol acetate (1) and a variety of phenols gave the coupling compounds. A mechanistic consideration of the reaction is also presented.View full abstractDownload PDF (1015K) -
CHUZO IWATA, TAKAFUMI FUSAKA, NAOYOSHI MAEZAKI, SHIZUO NAKAMURA, YASUT ...1988 Volume 36 Issue 5 Pages 1638-1645
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metal-ammonia reduction of the cyclopenta[c]benzofuran derivative (2b) afforded a mixture of 4-epi-β-acorenol (5), a disubstituted olefin (8) as the main product, and a perhydro compound (9). Compound 8 was converted to 5 via the exo-diene (15). Dehydration of 5 afforded the 4-epi-β-acoradiene (6), selective reduction of which gave the monoolefin (7), and then the allylic oxidation of 7 gave (±)-acorenone (3) in good yield.View full abstractDownload PDF (811K) -
MASAYUKI AGETA, GEN-ICHIRO NONAKA, ITSUO NISHIOKA1988 Volume 36 Issue 5 Pages 1646-1663
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new class of ellagitannins, castanopsinins A-H (1, 6, 25, 27, 32, 42, 47 and 51), containing a triterpenoid glycoside core, have been isolated from the leaves of Castanopsis cuspidata var. sieboldii NAKAI (Fagaceae). On the basis of spectroscopic and chemical data these compounds have been characterized as 3, 23-(R)-(1), 24-O-galloyl-3, 23-(R)-(6), 2, 3-(R)-(25), 3, 23-(S)-(27), 3, 24-(S)-(32), 24-O-galloyl-3, 23-(S)- (42), 3'-O-galloyl-23, 24-(R)- (47) and 24, 3'-di-O-galloyl-3, 23-(R)-hexahydroxydiphenoyl (51) 2α, 3β, 23, 24-tetrahydroxyolean(urs)-12-en-28-oic acid 28O-β-D-glucopyranosides. In addition, separation of structural isomers consisting of a mixture of oleanane- and ursane-type triterpenoids was successfully achieved.View full abstractDownload PDF (1517K) -
TAKAO SAKAMOTO, EISAKU KATOH, YOSHINORI KONDO, HIROSHI YAMANAKA1988 Volume 36 Issue 5 Pages 1664-1668
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe cross-coupling of 3-iodo- and 3-bromopyridine with the carbanions derived from ethyl cyanoacetate and malononitrile in the presence of tetrakis(triphenylphosphine)palladium in 1, 2-dimethoxyethane gave ethyl α-cyanopyridine-3-acetate and 3-pyridinemalononitrile in moderate yields. This palladium-catalyzed cross-coupling proceeded smoothly with halopyrimidines, haloquinolines, haloisoquinolines, and also bromobenzene.View full abstractDownload PDF (494K) -
SYUICHI FURUYA, KIYOSHI OMURA, YOSHIYASU FURUKAWA1988 Volume 36 Issue 5 Pages 1669-1675
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When 6 was treated with acid, a novel ring transformation occurred to give methyl (6-ethoxycarbonyl-3, 4-dihydro-4-oxopyrimidin-5-yl)acetates (12).View full abstractDownload PDF (792K) -
FUMIO HASHIMOTO, GEN-ICHIRO NONAKA, ITSUO NISHIOKA1988 Volume 36 Issue 5 Pages 1676-1684
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical examination of the aqueous acetone extract of commercial oolong tea has led to the isolation of four new theasinensins D-G, and a new type of dimeric flavan-3-ol named oolong-theanin, together with previously reported theasinensins A, B, and C. On the basis of chemical and spectroscopic evidence, theasinensins D and E were characterized as atropisomers (4 and 5) of theasinensins A (1) and C (3), respectively, while theasinensins F and G were shown to be B, B'-linked bisflavanoids (6 and 7) consisting of (-)-epicatechin 3-O-gallate and (-)-epigallocatechin 3-O-gallate units, in which the biphenyl bonds possess S- and R-chiralities, respectively. Similarly, oolongtheanin was characterized as a novel metabolite (8), probably derived from theasinensins by oxidation of one of the B-rings.View full abstractDownload PDF (860K) -
JINSAKU SAKAKIBARA, SHIN-ICHI NAGAI, TEPPEI AKIYAMA, NORIICHI ODA, TAI ...1988 Volume 36 Issue 5 Pages 1685-1691
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBenzofuro[2, 3-d]pyridazin-4(3H)-one (1) was converted into 4-chloro-(3) and 4-ethoxy-benzofuro [2, 3-d]pyridazine (4). Reaction of 1 with phosphorus pentasulfide provided benzofuro-[2, 3-d]pyridazine-4-thione (2), which underwent S-methylation to give the 4-thiomethyl derivative (5). Hydrazinolysis of 2 or 3 proceeded efficiently to give the corresponding 4-hydrazino compound (6). Compound 6 was cyclized with nitrous acid to afford benzofuro[2, 3-d]tetrazolo[1, 5-b]-pyridazine (7), which was alternatively prepared from 3 or 4 with sodium azide.3-Substituted benzofuro[2, 3-d][1, 2, 4]triazolo[4, 3-b]pyridazines (8-12) were prepared by cyclization of 6. Refluxing 6 with ethyl pyruvate in ethanol followed by cyclization in acetic acid provided a novel 4H- benzofuro[2', 3' : 4, 5]pyridazino[3, 2-c][1, 2, 4]triazin-4-one (14).View full abstractDownload PDF (775K) -
HIROSHI TOMISAWA, HIROTO NAKANO, HIROSHI HONGO1988 Volume 36 Issue 5 Pages 1692-1697
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Diels-Alder reaction of 2-methylene-1, 2-dihydropyridines (Ia-f) with dienophiles such as maleic anhydride, maleimide, and N-phenylmaleimide proceeded in a stereoselective manner to give the endo-adducts (IIIa-i). This reaction provides a simple synthetic method for isoquinuclidines having a carbon side-chain at the 3-position.View full abstractDownload PDF (663K) -
MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, MASAHIRO KATAOKA, AKIHIK ...1988 Volume 36 Issue 5 Pages 1698-1706
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Cyanoisothiochromans 4 were synthesized by the intramolecular Pummerer reaction of cyanomethyl phenethyl sulfoxides 3 with trifluoroacetic anhydride. Alkylation of the isothiochromans 4 afforded isothiochromanium salts 5 which consist of cis- and trans-isomers. 1-Cyano-2-methyl-3, 4-dihydro-1H-2-thionianaphthalen-1-ides 6 were prepared by deprotonation of 5 with triethylamine or sodium hydride. Thermal reaction of the ylide 6a in benzene or N, N-dimethylform-amide gave the 1, 2-rearranged product 7 accompanied with the dimers 8, whereas the reaction in acetonitrile gave the dimers E-8 (8-I) (31.6%) and Z-8 (8-II) (22.6%) as the major products. The geometrical structures of 8 were determined by infrared (IR) and Raman spectroscopy. The dimers 8 were formed at room temperature by treatment with tetracyanoethylene or 7, 7, 8, 8-tetracyano-quinodimethane. Unexpected products, 1-benzylated isothiochromans 10, were obtained upon heating 6a in toluene and its derivatives. A reaction mechanism involving the benzyl radicals was postulated for this novel solvent-uptake reaction.View full abstractDownload PDF (976K) -
NAOKI NODA, MASATOSHI NISHI, KAZUMOTO MIYAHARA, TOSHIO KAWASAKI1988 Volume 36 Issue 5 Pages 1707-1713
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo resin glycosides, muricatins VII (1) and VIII (2) were isolated from the seeds of Ipomoea muricata (L.) JACQ. (Convolvulaceae). They were respectively characterized as 11R-jalapinolic acid 11-O-(4-O-(3R-hydroxy-2R-methylbutyryl))-β-D-fucopyranosyl-(1→4)-(2-O-(2S-methylbutyryl))-α-L-rhamnopyranosyl-(1→2)-β-D-quinovopyranosyl(qui')-(1→2)-β-D-quinovopyranosyl-1, 3(qui')-olide and 11R-jalapinolic acid 11-O-(α-L-rhamnopyranosyl-(1→2))-β-D-quinovopyranosyl(qui'')-(1→3)-β-D-quinovopyranosyl-(1→2)-β-D-quinovopyranosyl-1, 2(qui'')-olide on the basis of chemical and spectral data. Muricatic acid C previously obtained was also characterized as the glycosidic acid of 2.View full abstractDownload PDF (732K) -
YOSHIFUMI MAKI, KAORU SHIMADA, MAGOICHI SAKO, YUKIO KITADE, KOSAKU HIR ...1988 Volume 36 Issue 5 Pages 1714-1720
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIrradiation of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone (2) (Emorfazone) with ultraviolet (UV)-visible light in the presence of 1, 3, 7, 9-tetrabutyl-2, 4, 6, 8(1H, 3H, 7H, 9H)-pyrimido-[5, 4-g]pteridinetetrone 5-oxide (1a), followed by chromatography of the reaction mixture, resulted in the isolation of 5-(2, 3-dihydro-1, 4-oxazin-4-yl)-4-ethoxy-2-methyl-3(2H)-pyridazinone (3), 4-ethoxy-5-(2-hydroxyethylamino)-2-methyl-3(2H)-pyridazinone (4), 4-ethoxycarbonyl-2-methyl-4-morpholino-3(2H)-pyrazolone (5), 4, 4'-bi[4-ethoxycarbonyl-2-methyl-3(2H)-pyrazolone] (6) and 1, 3, 7, 9-tetrabutyl-2, 4, 6, 8(1H, 3H, 7H, 9H)-pyrimido[5, 4-g]pteridinetetrone (1b). The product 3 is produced as a result of photochemical dehydrogenation of 2 by 1a. The formation of the morpholine-ring-opening product 4, one of the metabolites of 2, was proved to occur via the autoxidation of 3 and subsequent stepwise ring cleavage in the presence of oxygen and moisture. The formation of the novel ring-contracted product 5 involves oxygen-atom transfer from 1a to 2 in an excited state. The dimer 6 was shown to be a secondary product formed by further photolysis of 5.View full abstractDownload PDF (816K) -
SHOETSU KONNO, MATAICHI SAGI, ETSUKO TAKAHARU, SATOSHI FUJIMURA, KAZUH ...1988 Volume 36 Issue 5 Pages 1721-1726
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Methyl-5, 6-diphenyl-1, 2, 4-triazne (1) was treated with chlorine to give 3-trichloromethyl-5, 6-diphenyl-1, 2, 4-triazine (2) as a sole product. On treatment with an excess (4.5 mol eq) of triphenylphosphine, 2 was transformed into α-(5, 6-diphenyl-1, 2, 4-triazin-3-yl)methylenetriphenyl-phosphorane (3) in improved yield. The condensation of 3 with various aldehydes afforded 3-alkenyl-5, 6-diphenyl-1, 2, 4-triazines (6).The application of this method to the 5-position and 6-position of 1, 2, 4-triazine was also investigated.View full abstractDownload PDF (633K) -
KUNIO HIROI, KUNITAKA MAKINO1988 Volume 36 Issue 5 Pages 1727-1737
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUpon treatment with a zero-valent palladium catalyst, tetrakis(triphenylphosphine)palladium, in tetrahydrofuran under mild conditions allylic p-toluenesulfinates underwent α- or γ-rearrangements of the sulfonyl group via ionic intermediates to give allylic sulfones. The regiochemistry of the rearrangement depends on the character of the intermediary allylic cationic carbons generated and the steric hindrance involved therein.View full abstractDownload PDF (1117K) -
HITOSHI TANAKA, MASAYA ISHIHARA, KAZUHIKO ICHINO, KAZUO ITO1988 Volume 36 Issue 5 Pages 1738-1743
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCompound 8 was reacted with 7 in the presence of potassium tert-butoxide to give the condensation product (9), which was reduced with lithium borohydride to afford a mixture of alcohols (10a, b). The alcohols underwent cyclization with concentrated hydrochloric acid to furnish propacin (1). Its regioisomer (3) was also synthesized from the condensation product (13) through a similar route.View full abstractDownload PDF (692K) -
KUNIO HIROI, KUNITAKA MAKINO1988 Volume 36 Issue 5 Pages 1744-1749
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of allylic (±)-p-toluenesulfinate with tetrakis(triphenylphosphine)palladium in the presence of chiral phosphine ligands resulted in allylic sulfinate-sulfone rearrangements to give the corresponding optically active allylic sulfones in high optical yields. The palldium-catalyzed reactions of readily obtainable allylic acetates with sodium p-toluenesulfinate in the presence of chiral phosphine ligands provide a new method for preparation of optically active allylic sulfones with high enantiomeric excess.View full abstractDownload PDF (606K) -
IKUO FUJII, MASAKO KOREYUKI, KEN KANEMATSU1988 Volume 36 Issue 5 Pages 1750-1757
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of O-allyl S-alkyl dithiocarbonates of codeine and isocodeine were examined under thermal and catalytic conditions. Heating of a xylene solution of xanthates (3, 4, and 5) gave the corresponding S-allyl S-alkyl dithiocarbonates (6, 7, and 8) via [3, 3] sigmatropic rearrangement in high yields, overcoming the difficulty of attack on the hindered α-face. On the other hand, in the case of isocodeine, the formation of xanthates followed by the rearrangement took place without heating to afford the dithiocarbonates (9, 10, and 11). Furthermore, compound 10 rearranged with extrusion of COS to give the sulfide (14). The reactions of 3, 6, and 9 with phosphine-palladium (0) complex and a Lewis acid as catalysts were also examined. When 3 or 6 was treated with (Ph3P)4Pd, elimination reaction proceeded to give 6-demethoxythebaine (17). The reactions of 6 and 9 with TiCl4 yielded the corresponding cyclic dithiocarbonates 18 and 19.View full abstractDownload PDF (866K) -
MASATOSHI YAMATO, KUNIKO HASHIGAKI, SHIGETAKA ISHIKAWA, SUSUMU HITOMI, ...1988 Volume 36 Issue 5 Pages 1758-1765
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-benzyl-2-(isochroman-1-yl)-1-methylethylamine (6f), prepared by the reaction of 1-ethoxy-isochroman (4) and acetone followed by reductive amination, was found to possess inhibitory activity against aspirin-induced ulcer but did not exhibit gastric antisecretory activity. Structural modification of 6f was undertaken and the structure-activity relationships of the derivatives are discussed.View full abstractDownload PDF (856K) -
KOICHI KAWASAKI, MITSUKO MAEDA, JOE WATANABE, HIROSHI KANETO1988 Volume 36 Issue 5 Pages 1766-1771
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLeu-enkephalin analogues containing a ureylene bond instead of an amide bond were synthesized. The ureylene bond was formed by a coupling reaction of the isocyanate derived from the corresponding azide by Curtius rearrangement reaction. Three analogues, each of which has a ureylene bond at the Tyr-Gly or Gly-Gly or Phe-Leu amide bond, were prepared. The ureylene bond resisted enzymatic hydrolysis, but the biological activities of the synthetic peptides on guinea pig ileum and mouse was deferens were low compared with those of Leu-enkephalin.View full abstractDownload PDF (609K) -
CHIKAKO SHIMIZU, KIYOSHI IKEDA, KAZUO ACHIWA1988 Volume 36 Issue 5 Pages 1772-1778
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe syntheses of novel tetraacetylsialyl- and sialyl-(α2-6)-D-glucosamine-4-phosphate analogues of lipid A containing sialic acid in place of 3-deoxy-D-mannno-2-octulosonic acid (KDO) are described. Preliminary examination of the biological activity revealed that two synthetic disaccharides possessed weak mitogenic activities.View full abstractDownload PDF (752K) -
KEIJI WADA, SEIKOU ISHIGAKI, KAORI UEDA, YUTAKA TAKE, KEIKO SASAKI, MA ...1988 Volume 36 Issue 5 Pages 1779-1782
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA toxic substance, 4-O-methylpyridoxine, responsible for "gin-nan food poisoning" was isolated from seeds of Ginkgo biloba L. (Ginkgoaceae). It is proposed that the toxic principle causes food poisoning through not only antagonizing vitamin B6 in the body but also inhibiting the formation of 4-aminobutyric acid from glutamate in the brain.View full abstractDownload PDF (467K) -
KOTARO IDAKA, YASUAKI HIRAI, JUNZO SHOJI1988 Volume 36 Issue 5 Pages 1783-1790
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe constituents of the leaves of Sabal causiarum BECC. have been investigated. Vitexin, methyl proto-deltonin, methyl proto-causiaroside I(=26-O-β-D-glucopyranosyl 22-O-methyl-25(R)-furost-5-en-3β, 26-diol 3-O-[α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→4)][α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranoside) and causiaroside II(=3β, 16β-dihydroxypregn-5-en-20-one 3-O-[α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosy(1→4)][α-L-rhamnopyranosyl(1→2)]-β-D-glucopyranosyl 16-O-[δ-(β-D-glucopyranosyloxy)-γ-methyl]-valerate) were isolated and identified. This is the first isolation and characterization of the latter two compounds from a natural source, and these results are interesting from the standpoint of the biogenesis of the steroidal glycosides of the Palmae plants.View full abstractDownload PDF (817K) -
CHIEN-CHIH CHEN, YU-LIN HUANG, YUH-PAN CHEN, HONG-YEN HSU, YUEH-HSIUNG ...1988 Volume 36 Issue 5 Pages 1791-1795
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new neolignans, fargesone A (I), fargesone B (II) and fargesone C (III), together with two known compounds, denudatin B (IV) and syringin (V), have been isolated from the flower buds of Magnolia fargesii, and their structures determined.View full abstractDownload PDF (506K) -
FUMIYUKI KIUCHI, YOSHISUKE TSUDA, KAORU KONDO, HIROYUKI YOSHIMURA, ITS ...1988 Volume 36 Issue 5 Pages 1796-1802
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTannins, both condensed and hydrolyzable, wre found to cause bursting of the second-stage larvae of dog roundworm (Toxocara canis), when combined with an appropriate larvicidal compound such as decanoic acid or tetradecanol. This bursting activity of tannins increased with increase of the degree of condensation for condensed tannins and with increase of the proportion of phenolic moieties for hydrolyzable tannins. since tannins are not larvicidal by themselves, the appearance of this bursting activity requires the coexistence of larvicides. The activity was strongly induced by larvicides with a polar functional group such as an acid or an alcohol, but weakly induced by those with a less polar group such as an amide. Tannins were also found to enhance the killing activity of acidic larvicides. These facts suggested the practical effectiveness of the combination of tannins and an appropriate anthelminitic for the treatment of parasitic diseases.View full abstractDownload PDF (709K) -
NORIAKI KOBAYASHI, EIJI TERADA, YOSHINORI SAKURAI, HIROKAZU SUZUKI, AK ...1988 Volume 36 Issue 5 Pages 1803-1807
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA solid-phase enzyme immunoassay to detect antibodies by the measurement of guinea pig C3 bound to antigen-antibody complex has been developed. Briefly, antibodies in heat-inactivated sera are reacted with antigens coated on the surface of microtiter plates. Guinea pig C3 is bound to the antigen-antibody complexes, and then the amount of C3 is measured using horseradish peroxidase-labeled anti-C3.When this enzyme immunoassay was applied to the diagnosis of Mycoplasma pulmonis infection in rats, high sensitivity and specificity were observed : 95% or more of 20 sera from M. pulmonis-infected rats confirmed by cultivation were positive regardless of the antigen strains used, while no positive reaction was detected in 20 normal rat sera. In the complement fixation test, only 12 were positive out of the above-mentioned 20 positive sera, despite the use of the solid-phase antigen which gave the maximal binding.The present assay is simple, highly sensitive and specific, and is considered to be a useful tool for the diagnosis of M. pulmonis infection in rats.View full abstractDownload PDF (516K) -
HIROSHI HOSODA, REIKO TSUKAMOTO, KOHICHI SHORIKEN, WATARU TAKASAKI, TO ...1988 Volume 36 Issue 5 Pages 1808-1813
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe use of 3, 3', 5, 5'-tetramethylbenzidine (TMB) as a chromogen in a testosterone enzyme immunoassay system with a glucose oxidase label is described. Glucose oxidase activity was measured with glucose, peroxidase and TMB in acetate-citric acid buffers ; the optimum pH value was found to be 4.2. The glucose oxidase-labeled antigen was prepared by the N-succinimidyl ester method. In the competitive enzyme immunoassay, the bound and free enzyme-labeled antigens were separated by a double antibody method. A dose-response curve with a high sensitivity was obtained by the use of a minimum amount of the label at an appropriate dilution of anti-testosterone antiserum (Ka=2×1010M-1). The amount of testosterone needed to displace 50% of the bound lab el was 24 pg. The sensitivity was higher than that of the assay system using 2, 2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid), ABTS.View full abstractDownload PDF (647K) -
TOSHIO MAZUDA, WILLIAM-L. GYURE1988 Volume 36 Issue 5 Pages 1814-1818
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy combining the theophylline inhibition assay for placential isoenzyme analysis with the lectin precipitation procedure for bone isoenzyme detection, a new more complete method for alkaline phosphatase isoenzyme analysis was devised. Moreover, the method employs common clinical laboratory instruments and is easy to perform.After an examination of the method and its verification by electrophoretic methods with commercial control samples and clinical samples, a careful study was performed to determine the normal ranges. These results were then used as guidelines for placing patients in clinical categories. Verification of these categories by other clinical data on the patients confirmed the validity of the method.View full abstractDownload PDF (666K) -
IKUKO HISHIDA, HIROAKI NANBA, HISATORA KURODA1988 Volume 36 Issue 5 Pages 1819-1827
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe acid-insoluble, alkali-soluble, hot-water-extractable polymer (a polysaccharide containing approximately 30% of protein; D-fraction) obtained from the fruit bodies of Grifola frondosa (maitake) exhibited antitumor activities against allogenic and syngeneic tumors on oral administration to mice. Winn assay conducted to examine the tumor growth-suppressing effect revealed a complete inhibition of the tumor by the oral administration of D-fraction. This fact indicates that stimulation of the immune response system triggered by the tumor-bearing state is activated by D-fraction. Consequently, the activity of D-fraction on cells associated with immune response was examined. The cytolytic activity and interleukin-1 productivity of macrophages or T cells which exhibit antigen-specific cytotoxicity were enhanced. D-fraction was found to potentiate the delayed-type hypersensitivity response which is associated with tumor growth suppression.View full abstractDownload PDF (879K) -
KEIKO UNNO, HIROKI BUSUJIMA, SHIGEKI SHIMBA, KUSUO NARITA, SHOJI OKADA1988 Volume 36 Issue 5 Pages 1828-1833
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of deuterium oxide (D2O) was examined on the cell growth of photoautotrophically growing Chlorella ellipsoidea. The growth rate was inversely proportional to the concentration of D2O in the medium up to 60 mol%. The growth in D2O medium at concentrations higher than 60 mol% was highly inhibited. However, the cells pre-cultured in 60 mol% D2O medium became able to grow even in practically 100 mol% D2O medium. Deuterium (D) was incorporated into cells proportionally to the concentration of D2O in the medium. The D/H ratio in the cells was lower than that of the cultivation medium. Chlorella cells cultured in practically 100 mol% D2O medium contained ca. 70 mol% D. Of the D incorporated into cells, about 20% was easily exchangeable with H, and the remaining 80% was unexchangeable.View full abstractDownload PDF (564K) -
YUKIO ASO, SUMIE YOSHIOKA, TOSHIO SHIBAZAKI, MITSURU UCHIYAMA1988 Volume 36 Issue 5 Pages 1834-1840
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetics of racemization of oxazepam was examined by an high-performance liquid chromatographic (HPLC) method modified for simultaneous determination of each enantiomer of oxazepam and oxazepam acetate by using a chiral stationary phase in order to clarify the factors affecting the racemization rate. The racemization of oxazepam is too fast to allow the isolation of optically active oxazepam. Optically active oxazepam acetate, which was stable enough in configuration to be isolated by HPLC, could be utilized to determine the racemization rate of oxazepam as follows. In the strongly alkaline pH region, the hydrolysis rate of oxazepam acetate was larger than the racemization rate of oxazepam, and more than 93% enantiomeric purity of oxazepam in solution was obtained on hydrolysis of optically active oxazepam acetate at pH 14 and 0°C. The racemization rates of oxazepam were determined over the pH range from 0.5 to 13.5 at a constant ionic strength of 0.5. The dependence of the racemization rates on the pH, ionic strength and dielectric constant of the reaction mixture suggests that the racemization of oxazepam can be ascribed to spontaneous reaction of neutral oxazepam species in the neutral pH region and to hydroxide ion-catalyzed reaction of neutral oxazepam or to spontaneous reaction of dissociated oxazepam species in the basic pH region.View full abstractDownload PDF (705K) -
HIROSHI KIWADA, IWAO NAKAJIMA, HIROSHI MATSUURA, MITSUKO TSUJI, YURIKO ...1988 Volume 36 Issue 5 Pages 1841-1846
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLong-chain alkyl glycosides form liposome-like vesicles. However, they are unstable in plasma and thus are unsuitable as drug carriers. The mechanisms causing the instability of palmitoyl glucoside vesicles (Glu-liposomes) in plasma were investigated in this study. They very rapidly released about 70% of their aqueous content at the start of incubation with fresh rat plasma at 37°C. On the other hand, phosphatidylcholine liposomes (PC-liposomes) released about 30% of their content, though the release pattern was very similar. Two components were suspected to b involved in destabilizing the Glu-liposomes in plasma from a plasma dilution experiment, and their effects seemed to depend on the type or size of the vesicles. The activity disappeared on pre-heating of the plasma at 56°C for 30 min in the case of PC-liposomes, but not Glu-liposomes, and about 35% of the contents of the latter was still released on incubation even with pre-heated plasma. This result indicates that the activity destabilizing glycoside vesicles in plasma was composed of two factors, one heat-stable and the other heat-labile. The heat-stable one was consumed by incubation with empty glycoside vesicles, regardless of the sugar moiety or size of vesicles, but not by PC-liposomes. Therefore, the heat-stable factor seemed to be specific to vesicles covered with sugar moieties. By fractionation of plasma protein by the salting-out technique, the activity was found in the albumin fraction.View full abstractDownload PDF (690K) -
TOSHIKIRO KIMURA, AKIRA KOBAYASHI, MIYOKO KOBAYASHI, KANAE NUMATA, YUK ...1988 Volume 36 Issue 5 Pages 1847-1856
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe intestinal absorption of drugs was investigated in rats with glycerol-induced renal failure by an in situ loop method. Drugs examined were poorly-absorbable drugs (sulfanilic acid, procainamide ethobromide, cefazolin and sulfaguanidine), well-absorbable drugs (sulfisoxazole, quinine, salicyclic acid and impramine), actively-transported drugs (cefadroxil and cyclacillin) and water-soluble, high-molecular-weight compounds (polyethylene glycol (PEG) 1000, PEG 1500 and fluorescein isothiocyanate-conjugated dextran with a molecular weight of 4000). The absorption of all the low-molecular-weight drugs was significantly increased in the renal failure group, regardless of the absorption characteristics. The enhancement of membrane permeability was also observed by an in vitro cannulated everted sac method. The investigation of membrane permeability to high-molecular-weight compounds with PEG 1000 and 1500 showed that the enhancement of membrane permeability in the renal failure state was limited to molecules whose molecular weights were lower than about 1000. Furthermore, the enhancement of membrane permeability was seen in the brush border membrane vesicles prepared from the small intestine of rats with renal failure, although lipid fluidity, as assessed by steady-state fluorescence polarization techniques using 1, 6-diphenyl-1, 3, 5-hexatriene as a probe was not changed in brush border membranes of the diseased rat. On the other hand, a reduction of thickness of the unstirred water layer adjacent to the membrane was observed. Examination by transmission electron microscopy revealed blebs at the tip of microvilli and the thickness of the glycocalyx was reduced. Possible mechanisms of the increase in drug absorption are discussed separately for poorly-absorbable and well-absorbable drugs.View full abstractDownload PDF (1267K) -
MASAO KIGUCHI, JUN-ICHI SUDO1988 Volume 36 Issue 5 Pages 1857-1864
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe nephrotoxic effects of cephaloridine on the renal concentration capacity were examined in rats that had received a single intravenous injection of cephaloridine (100 or 500 mg/kg body weight). An increase in urinary volume and a decrease in urinary osmotic pressure were observed continuously from the first to the sixth day in the 500 mg/kg group, but not in the 100 mg/kg group. In addition, rises in plasma levels of arginine-vasopressin were observed in the 100 and 500 mg/kg groups. Furthermore, responsiveness to exogenous arginine-vasopressin was investigated in the cephaloridine-administered rats under ethanol anesthesia. The injection of arginine-vasopressin caused relatively slight responses, in terms of the urine flow and urinary osmolality, in the cephaloridine-administered group in comparison to the control group. these findings indicate that cephaloridine induces a vasopressin-resistant polyuria, and strongly suggest that cephaloridine does damage the collecting tubules in the kidney.View full abstractDownload PDF (820K) -
HIDENOBU OHMORI, HATSUO MAEDA, CHIHIRO UEDA, MASAICHIRO MASUI1988 Volume 36 Issue 5 Pages 1865-1868
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclic voltammetry of Ph3P (1) in MeCN at a glassy carbon electrode showed two closely located anodic peaks. The first anodic peak corresponds to the oxidation of 1 to give Ph3P=O and Ph3PH+ (2), where water contaminating the medium is the source of the oxygen and the porton. The second peak, which was depressed by an increase in voltage sweep rate, is suggested to involve the oxidation of 1 preceded by a slow deprotonation of 2 formed at the first anodic peak.View full abstractDownload PDF (467K) -
HIROSHI HARA, MASATOSHI MURAKATA, OSAMU HOSHINO, BUNSUKE UMEZAWA, TSUT ...1988 Volume 36 Issue 5 Pages 1869-1871
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 8, 8a-epoxy-1, 2, 3, 4, 4a, 7, 8, 8a-octahydro-4a-hydroxy-6-methoxy-2-methyliso-quinolin-7-one (6), derived from the p-quinol acetate (1), with phenols gave the bistetrahydroisoquinolines (10-13).View full abstractDownload PDF (416K) -
KIMIO FURUHATA, SHINGO SATO, MOTOAKI GOTO, HIROAKI TAKAYANAGI, HARUO O ...1988 Volume 36 Issue 5 Pages 1872-1876
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of N-acetyl-2, 3-dehydro-2-deoxyneuraminic acid has been established by means of X-ray crystal structure analysis. The ring system was determined to have a 4H5(D) conformation.View full abstractDownload PDF (491K) -
HIROSHI TAKAHASHI, SHAOSHUN LI, YOSHIHIRO HARIGAYA, MASAYUKI ONDA1988 Volume 36 Issue 5 Pages 1877-1881
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo enantiomeric chalcone epoxides 2a and 2b are synthesized under phase-transfer conditions using 1-benzylquinidinium chloride and 1-benzylquininium chloride as catalysts, respectively Stereoselective cyclization of 2a and 2b, followed by methylation and preparative high performance liquid chromatography gives pure (+)-aromadendrin trimethyl ether (4a) and its enantiomer 4b. Reduction of pure 4a and 4b with NaBH4. affords four pure flavan-3, 4-diol trimethyl ethers, 5a, 6a, 5b, and 6b.View full abstractDownload PDF (553K) -
HIROSHI TOMISAWA, REIKO FUJITA, HIDEKI KATO, KAZUHIKO HAYASAKA, TAIKI ...1988 Volume 36 Issue 5 Pages 1882-1885
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Diels-Alder reactions of 4-cyano, 4-methoxycarbonyl-, and 4-acetyl-2(1H)-pyridones (I, II, and IV) with 1, 3-butadiene derivatives (III and V) were carried out to give 4a-substituted tetrahydro-1(2H)-isoquinolone derivatives (VI-IX, XV, XIX, and XX).View full abstractDownload PDF (513K) -
YOSHIO TAKEDA, TERUYOSHI ICHIHARA, YOSHIHISA TAKAISHI, TETSURO FUJITA1988 Volume 36 Issue 5 Pages 1886-1889
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDerivatives of kamebakaurin and kamebacetal A with an aldehyde function at C-20 undergo an intramolecular hydride rearrangement (crossed Cannizzaro reaction) under mild basic conditions. The mechanism is discussed.View full abstractDownload PDF (490K) -
TAKAO SAKAMOTO, MASAYUKI AN-NAKA, YOSHINORI KONDO, TOMIO ARAKI, HIROSH ...1988 Volume 36 Issue 5 Pages 1890-1894
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour kinds of pyranopyridinones were synthesized from pyridinecarbonitriles containing a chlorine or bromine substituent at the adjacent position to the cyano group by the palladium-catalyzed cross-coupling reaction with terminal acetylenes followed by intramolecular cyclization with polyphosphoric acid.View full abstractDownload PDF (475K) -
KENJIRO SUZUKI, MASAHIDE NOJI, TAZUKO TASHIRO, YOSHINORI KIDANI1988 Volume 36 Issue 5 Pages 1895-1898
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral Pt(II) complexes of riboflavin (RF) and flavin mononucleotide (FMN) with 1, 2-cyclohexanediamine (dach) or 2-(aminomethyl)cyclohexylamine (amcha) isomers were prepared. The coordination sites of RF or FMN to Pt(II) ions were determined to be N(5) and O(6) with resultant chelate ring formation.Antitumor activities of the dach or amcha Pt(II) complexes were tested against murine leukemia L1210 and all of them were antitumor-active. Pt(FMN)(trans-l-dach) exhibited the higher activity with a T/C% value of 326, with 4 cured mice out of 6. These results justify further testing.View full abstractDownload PDF (477K) -
TAKEO KAWAGUCHI, MINEO SANEYOSHI1988 Volume 36 Issue 5 Pages 1899-1901
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInhibition constants (Ki) of pyrimidine acyclonucleosides and several normal pyrimidine metabolites for the phosphorolytic degradation of 5-fluoro-2'-deoxyuridine (FUdR) in rat and beagle tissue homogenates (liver and small intestine) were measured. Acyclothymidine (AcycTdR) showed the lowest Ki value for all the homogenates. The Ki/Km values of AcycTdR and acyclouridine (AcycUdR) depended on the homogenates, and the values (Ki/Km) in the rat liver homogenate were higher than those in all other homogenates.View full abstractDownload PDF (388K) -
HIROSHI NISHIYA, KATSUMI ISHIWATA, KAZUO KOMATSU, OKITSUGU NAKATA, KEN ...1988 Volume 36 Issue 5 Pages 1902-1904
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo potent inhibitors of platelet aggregation were isolated from the chloroform extract of jyuyaku (Houttuyniae herb), a traditional medicine in Japan and China, by a combination of high-performance liquid chromatography and other techniques. These compounds were identified as cis- and trans-N-(4-hydroxystyryl)benzamide by proton nuclear magnetic resonance spectrometry.View full abstractDownload PDF (407K) -
HIDETAKA YUKI, YUTARO AZUMA, NORIO MAEDA, HIDEKI KAWASAKI1988 Volume 36 Issue 5 Pages 1905-1908
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sensitive method for the determination of eicosapentaenoic acid (EPA) in human serum and the detection of some other fatty acids was developed. Fatty acids were labeled with N-(4-aminobutyl)-N-ethyl-isoluminol (ABEI), and separated by reversed-phase high-performance liquid chromatography. The eluate was mixed with 0.2 μM microperoxidase solution and 90 mM hydrogen peroxide solution successively, and the chemiluminescence was detected in a flow cell placed in front of a photomultiplier. The calibration curve of EPA was linear in the range of 2 pmol to 2 nmol. The recovery of EPA added to human serum was nearly 100%, and the detection limit was 200 fmol. Eleven fatty acids were detected in human serum samples by this method.View full abstractDownload PDF (453K) -
SATOSHI MUTO, HIROMICHI MINEMURA, HIDETAKA YUKI1988 Volume 36 Issue 5 Pages 1909-1913
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of lymphokines and interferon-γ on human monocyte chemiluminescence was studied by measuring the phorbol myristate acetate-induced luminol-dependent chemiluminescence. When human peripheral blood monocytes were incubated with lymphokines (culture supernatants of concanavalin A-stimulated human leukocytes), their ability to generate chemiluminescence increased rapidly, reaching a maximal level at about 4 h, and then decreased on further incubation. Similar results were obtained in experiments using a commercially available human interferon-γ in place of crude lymphokines. The increasing effect of interferon-γ on monocyte chemiluminescence was dose-dependent in the range of 0.1-102 U/ml. These results show that the monocyte chemiluminescence may be clinically useful as a simple and rapid method for the determination of human interferon-γ.View full abstractDownload PDF (561K) -
SHUN HIGUCHI, EIJI YUKAWA, TOSHINOBU AOYAMA1988 Volume 36 Issue 5 Pages 1914-1918
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe predictive performance of the Bayesian weighted least-squares method (BWLS), viz., the Bayesian method, was evaluated and compared with that of the ordinary weighted nonlinear least-squares method (OWLS) in a simulation study. Phenytoin was selected as a model drug for a one-compartment nonlinear model (Michaelis-Menten model). The patient population for the phenytoin study (Km : 3.9±2.1 μg/ml, Vmax : 6.78±1.27 mg/kg/d) was generated by using a random number generator.When estimating the parameters by the Bayesian method, the Vmax estimate was more precise than the Km : Vmax could be estimated with a 15% and 10% prediction error with one and two observations, respectively, as opposed to 30% and 20% for Km. It was also inferred that the predictive performance of the one- and two-observation BWLSs was a slightly better than or equal to that of the three-observation OWLS but did not approach that of the four-observation OWLS.The present simulation study indicated that the Bayesian method could provide reliable estimations of Michaelis-Menten parameters such as Km and Vmax and clinically acceptable predictions for the steady-state serum concentration with at least one observation (the root mean squared error, 3.4 μg/ml; 95% confidence interval, 1.4-4.6 μg/ml), if appropriate population pharmacokinetic parameters (i.e., means and variances) were available.View full abstractDownload PDF (605K) -
SEIKI TANADA, SHOZO TSUTSUI, KEITO BOKI, TAKEO NAKAMURA1988 Volume 36 Issue 5 Pages 1919-1921
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe adsorption characteristics of ammonia on several kinds of plasma-treated activated carbon (PT-AC) prepared under different treatment conditions were investigated from the adsorption isotherms, characteristic energy, and isosteric differential heats of adsorption. The amount of acid functional groups of the Pt-ACs was increased by 8-70% compared to that of raw activated carbon (R-AC) by plasma treatment. The amount of acid functional groups on the Pt-ACs increased with increase in oxygen pressure, reached a maximum at a pressure of 1.0 Torr and then decreased. The adsorption capacity, the characteristic energy, and the isosteric differential heats of adsorption for ammonia of No. 4 (treated at 1.5 Torr) were the greatest among the PT-ACs and R-AC. From the characteristic energy and heat of adsorption, it appeared that the acid functional groups were formed by the oxygen plasma treatment into micropores and supermicropores of activated carbon. it is concluded that the treatment conditions of No. 4 produced a characteristic adsorbent material having the greatest adsorption capacity for ammonia among the PT-ACs.View full abstractDownload PDF (375K) -
Sachiko Inui, Tomoko Otawa, Hiroko Nakae, Shozo Asada1988 Volume 36 Issue 5 Pages 1922-1925
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn interconversion model which incorporated a first-pass metabolism was applied to the disposition kinetics of 4-acetaminobenzaldehyde (AB) and its reversible metabolite, 4-acetaminobenzylalcohol (ABA) in the rat. The rates of available fraction of AB, FH1, and of the sequential available fraction of ABA, FH2, were estimated by application of the computer multi-lines fitting technique.View full abstractDownload PDF (399K) -
Ryuji Monden, Akihiko Manaka, Toshio Kasama, Eiichi Kotani, Seisho Tob ...1988 Volume 36 Issue 5 Pages 1926-1929
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxygenation of methyl O-acetyl-α-cyclohexyl-α-phenylglycolate (4c) with the reagent system Fe(MeCN)2+6-H2O2-Ac2O, a model enzyme system for mono-oxygenase, was investigated in connection with the metabolism of the drug oxybutynin hydrochloride (1) in humans and dogs. Among the oxygenation products 5d, 7, 8, and 9, 5d, 7, and 8 correspond to the mammalian metabolites of 1 except for the stereo-chemistry in 7 and 8. This suggests implications regarding the mechanism of the mammalian metabolism of the drug.View full abstractDownload PDF (388K) -
Akimasa Shibukawa, Terumichi Nakagawa, Mamoru Miyake, Hisashi Tanaka1988 Volume 36 Issue 5 Pages 1930-1933
Published: May 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProtein binding of warfarin with bovine serum albumin (BSA) was analyzed by HPLC with an internal-surface reversed-phase (ISRP) silica column. When a relatively large volume (2100 μl) of the sample solution containing warfarin and BSA was applied directly to the ISRP column, two distinct peaks appeared separately from the protein peak. one of these had a short retention time and was ascribable to warfarin released from the strong-binding sites on BSA molecules during the process of chromatography. The other peak had a long retention time and was due to the sum of free warfarin and that released from weak-binding sites. The separation profiles of these peaks were investigated with varying injection volumes and mobile phase conditions. The binding constants for the strong site and the weak site were determined from the area of these warfarin peaks. The results were comparable to the reported values.View full abstractDownload PDF (416K)
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