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Volume 38, Issue 8
Displaying 1-50 of 66 articles from this issue
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Tetsurou HANDA, Hiroaki KOMATSU, Atsuyuki KAKEE, Koichiro MIYAJIMA1990 Volume 38 Issue 8 Pages 2079-2082
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCosonication of egg yolk lecithin and triolein with apolipoproteins isolated from pig high density lipoprotein (apoHDL) gave us reconstituted high density lipoprotein particles (r-HDLs) of 9 nm in average diameter. They were smaller than microemulsion particles (MEs) composed of the lipids (35 nm). The protein/ egg yolk lecithin ratio in the fractionated r-HDLs was higher in the smaller particles. Binding of a hydrophobic probe, 2-p-toluidinylnaphthalene-6-sulfonate (TNS), to MEs, r-HDLs and apoHDL were evaluated on the basis of Halfman and Nishida's method. The reconstitution of apoHDL into MEs led to a 68% reduction in the binding of TNS and a small increase in the α-helix content as compared with free apoHDL. The binding experiments also showed the condensation of lecithin molecules at the r-HDL surface. The amphipathic helixes of apoHDL are located in the surface monolayer of egg yolk lecithin surrounding the triolein core. The intercalation of the hydrophobic residues of apoHDL between egg yolk lecithin molecules brings about a pronounced curvature of the surface and a decrease in the particle diametri.View full abstractDownload PDF (1114K) -
Kazuo SUZUKI, Rika KOBAYASHI, Kimio FURUHATA, Haruo OGURA1990 Volume 38 Issue 8 Pages 2083-2087
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-O-(5-Acetamido-3, 5-dideoxy-D-glycero-α- and -β-D-galacto-nonulopyranosylonic acid)-(2→6)-O-β-D-galacto-pyranosyl-(1→4)-1-(5-cholesten-3β-yloxy)-β-D-glucopyranose was synthesized under various conditions through a Koenigs-Knorr-like reaction. The stereochemistry of the products was confirmed by analysis of the nuclear magnetic resonance and circular dichroism spectra.View full abstractDownload PDF (719K) -
Kiyoshi KAWAMURA, Tomio OHTA, Genji OTANI1990 Volume 38 Issue 8 Pages 2088-2091
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 2-(2, 3-epoxy)propylphenyl acetate derivatives with catalytic amounts of NaI in organic solvent gave directly the corresponding 3-chromanyl acetate derivatives in good yields (86.6-98.0%). Similar treatment of 2-(2, 3-epoxy)propyl-6-methoxyphenyl N-mesyl-L-phenylalanylate gave a diastereomeric mixture of 8-methoxy-3-chromanyl N-mesyl-L-phenylalanylate, which was fractionated into both diatereomers by silica gel column chromatography. Subsequent hydrolysis of these isomers afforded the enantiomers of 8-methoxy-3-chromanol.View full abstractDownload PDF (748K) -
Kiyoshi KAWAMURA, Tomio OHTA, Genji OTANI1990 Volume 38 Issue 8 Pages 2092-2096
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn efficient synthesis of all four optical isomers of nipradilol has been achieved. Thus, 8-methoxy-3-chromanone was reduced enantioselectively with baker's yeast to afford (3R)-8-methoxy-3-chromanol, which, after derivation to (3R)-8-acyloxy-3-chromanol, was led to (3S)- or (3R)-8-hydroxy-3-chromanyl nitrate (7 or 9) by selecting a reaction with retention (using acetyl nitrate) or inversion (using Bu4N+NO3-) of configuration. Futher, (3S)- and (3R)-8-methoxy-3-chromanol, prepared via chemical resolution of 8-methoxy-3-chromanyl N-mesyl-L-phenylalanylate, were also led to 7 or 9 in the same manner. Using 7 and 9, four optically active glycidyl ether derivatives (11-14) were synthesized by using a novel Me4N+Cl--catalyzed etherification reaction of phenol with (S)- and (R)-epichlorohydrin. Subsequent amination of 11-14 with isopropylamine afforded the four optical isomers of nipradilol.View full abstractDownload PDF (726K) -
Atsuko NOSE, Tadahiro KUDO1990 Volume 38 Issue 8 Pages 2097-2101
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reduction of a variety of functional groups with the nickel(II) chloride-zinc system was investigated. This system reduced aldehydes, ketones, olefins, nitriles, oxime, nitro and heterocyclic compounds under mild conditions in good yields. It is of interest that some cases of reduction of ketones afforded the corresponding olefins and the saturated products, and the reduction of nitriles afforded the corresponding primary alcohols with the primary and secondary amines. The selective reduction of olefin and nitro functionalities in some compounds bearing carbonyl, ester and carboxyl functionalities was observed with this system.View full abstractDownload PDF (698K) -
Chihiro ITO, Toyoko MIZUNO, Shiho TANAHASHI, Hiroshi FURUKAWA, Motohar ...1990 Volume 38 Issue 8 Pages 2102-2107
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBisosthenon (1), a new dimeric coumarin, was isolated from the roots of some Citrus plants (Rutaceae), and the structure was elucidated to be 1, correspoding to a head-to-head dimer of osthenon (4), which was previously obtained from Citrus plants. The photodimerization of 4 gave 1 as well as two other dimeric products, 2 and 3.View full abstractDownload PDF (920K) -
Takashi ITOH, Mamiko OKADA, Kazuhiro NAGATA, Kentaro YAMAGUCHI, Akio O ...1990 Volume 38 Issue 8 Pages 2108-2111
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMonocyclic 1, 2, 3-triazines reacted with electron rich dienophiles to give pyridines and pyridazines. 4, 6-Disubstituted 1, 2, 3-triazine was denitrogenated to the azete intermediate, which afforded isomeric pyridines. 2, 5-Dihydrotriazines were oxidized by m-chloroperbenzoic acid to give 1, 2, 3-triazoles. Ring transformations of other triazine derivatives are also reported.View full abstractDownload PDF (649K) -
Yasuhiro NISHIYAMA, Sigeru NAKAYAMA, Yoshio OKADA, Kyong-Son MIN, Sato ...1990 Volume 38 Issue 8 Pages 2112-2117
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA pentacosapeptide corresponding to the entire amino acid sequence of Agaricus bisporus metallothionein (MT) and related cysteine-containing peptides were prepared by the conventional solution method and their heavy metal-binding properties were examined. The Cu2+- or Cu+-binding activities of various peptides were not greatly dependent on the peptide structure, so far as examined, although the pentacosapeptide, A. bisporus MT, exhibited slightly higher binding activity than the other peptides. On the contrary, the Cd2+-binding activities of these peptides were fairly structure-dependent.View full abstractDownload PDF (941K) -
Hisashi ISHII, Takao SUGIURA(nee HAGIWARA), Yohko AKIYAMA(nee KONDO), ...1990 Volume 38 Issue 8 Pages 2118-2126
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify the mechanism of the abnormal Fischer indolization of 2-methoxyphenylhydrazones the Fischer indolization of ethly pyruvate 2-(2, 6-dimethoxyphenyl)phenylhydrazone (6) was undertaken using ethanolic hydrogen chloride and zinc chloride as an acid catalyst. The cyclization was found to take place predominantly on the 2, 6-dimethoxyphenyl nucleus to give the corresponding indoles, although the yields of indoles formed were low. Some non-indolic by-products were also produced which might give information about the mechanism of Fischer indolization. In particular, the formation of 3, 5-dimethoxy-4-anilinobenzaldehyde (15) suggests that the first cyclization step in Fischer indolization could take place at the para position of phenylhydrazone as a side reaction.View full abstractDownload PDF (1432K) -
Fumiko ABE, Tsuneatsu NAGAO, Hikaru OKABE, Tatsuo YAMAUCHI, Nobuhiro M ...1990 Volume 38 Issue 8 Pages 2127-2129
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSParsonsianine, a 14-membered macrocyclic pyrrolizidine alkaloid, composed of retronecine, (2S, 3R)-2, 3-dihydroxy-2-ethylbutanoic acid and (2R, 3S)-2, 3-dihydroxy-2-isopropylbutanedioic acid, was isolated from the leaves of Parsonsia laevigata and the structure was determined by means of nuclear magnetic resonance and X-ray analysis.View full abstractDownload PDF (483K) -
Rumiko KAMAYA, Yoshiko TANAKA, Rie HIYAMA, Hiroyuki AGETA1990 Volume 38 Issue 8 Pages 2130-2132
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight triterpenoid hydrocarbons were characterized from the fresh leaves of Cheiropleuria bicuspis. They consist of hop-22(29)-ene, neohop-13(18)-ene, fern-7-ene, (18R)-dammara-13(17), 21-diene, eupha-7, 21-diene, 13α(H)-malabaricatriene, γ-polypodatetraene and squalene, all of which have different carbon skeletons, A new triterpenoid alcohol was isolated and established as 1α, 11α, 30-trihydroxyhopane. We also detected friedelin, hydroxyhopane, dryocrassol, lupeol, fernenol, 1α, 11α, 22-trihydroxyhopane, a mixture of sterols and a mixture of fatty acid esters of cycloartanoids, methylsterols and sterols. These findings suggest that Cheiropleuria bicuspis is related to Microsorium (Polypodiaceae), but are nevertheless consistent with the independency of Cheiropleuriaceae.View full abstractDownload PDF (584K) -
Kiyoshi TOMIOKA, Yuichi SHINMI, Kunihiko SHIINA, Makoto NAKAJIMA, Kenj ...1990 Volume 38 Issue 8 Pages 2133-2135
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnantioselective dihydroxylation of E-stilbene afforded (1S, 2S)-1, 2-diphenyl-1, 2-ethanediol in 70% ee by employing a stoichiometric amount of osmium tetroxide-chiral amine 5, prepared from N-methylephedrine and 2-bromopyridine.View full abstractDownload PDF (546K) -
Yoshisuke TSUDA, Yuki SAKAI, Akira NAKAI, Takeshi OHSHIMA, Shinzo HOSO ...1990 Volume 38 Issue 8 Pages 2136-2142
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral 2, 8-dioxo-1, 7-cycloerythrinan drivatives (bearing a 6β-ethoxycarbonyl or 6β-hydrogen substituent) were prepared in good yields from the reported 2, 8-dioxo-7β or 7α-hydroxyerythrinan derivatives by a base-catalyzed intramolecular alkylation of the corresponding O-mesylates, and they were shown to be useful intermediates for synthesizing natural erythrinan alkaloids. The C-1 of these compounds has been suitably protected for further manipulation at C-3 and the cyclopropane ring can be readily cleaved in a reductive or a non-reductive manner to give C-1 methylene or C-1 olefin derivatives. The latter process is discussed in detail with reference to several examples of ionic and radical opening. The reactivity of the carboxylate ester group on the cyclopropane ring bearing an electro-negative substituent was unusually high.View full abstractDownload PDF (1170K) -
Fumiko ABE, Tatsuro YAMAUCHI1990 Volume 38 Issue 8 Pages 2143-2145
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new tetrahydrofuranoid-lignan glycosides, tanegosides A, B and C, were isolated from Trachelospermum liukiuense HATSUSIMA, along with 8 lignan glycosides already known in T. asiaticum, and the structures were elucidated by spectral and chemical methods.View full abstractDownload PDF (566K) -
Tozo FUJII, Tohru SAITO, Shigeji MORI1990 Volume 38 Issue 8 Pages 2146-2150
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first total synthesis of the 8-oxopurine 8, a constituent of the marine sponge Hymeniacidon sanguinea GRANT, has been achieved via two alternative routes starting from 8-bromo-9-methyladenine (11), which is obtainable from 9-methyladenine (10) by bromination. The first route includes methylation of 11 with MeI to give the 1-methylated product 13·HI, conversion of 13·HI into the free base 13, and treatment of 13 with NaOAc in boiling AcOH to produce 8 in 25% overall yield (from 10). The second route includes treatment of 11 with boiling 1 N aqueous NaOH and methylation of the resulting 8-oxo derivative 12 with MeI, affording 8 in 63% overall yield (from 10). The rearranged isomer 15 and the N6 -acetyl derivative 9 have also been synthesized.View full abstractDownload PDF (787K) -
Gen-ichiro NONAKA, Takashi SAKAI, Takashi TANAKA, Kunihide MIHASHI, It ...1990 Volume 38 Issue 8 Pages 2151-2156
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of the C-glycosidic ellagitannins, castalagin, vescalagin, casuarinin and stachyurin, have been revised to 1-4 respectively, on the basis of two-dimensional nuclear Overhauser effect (NOE) spectroscopy and NOE difference spectroscopy. Furthermore, the structures of some related C-glycosidic tannins were re-examined by using similar techniques, and it was concluded that the configuration at the glucose C-1 position in all hitherto known C-glycosidic tannins must be revised.View full abstractDownload PDF (723K) -
Takehiro SANO, Yoshie HORIGUCHI, Suetaka KAMBE, Yoshisuke TSUDA1990 Volume 38 Issue 8 Pages 2157-2161
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotocycloaddition of 5-aryl-4-ethoxycarbonyl-1H-pyrrole-2, 3-dione 1 with isoprene and thermolysis of the resulting exo-vinyl cyclobutanes 6 caused a ring enlargement reaction due to a 1, 3-shift, giving rise to the hydroindoles 9, which were found to be regioisomeric to the hydroindoles 14 obtained as a major cycloadduct by the Diels-Alder reaction of the same addends. Thus, the two-step hydroindole synthesis, i.e., dioxopyrroline-diene photoannulation and thermolysis of the resulting vinyl cyclobutane, has a synthetic value in giving the product with the reverse regiochemistry to that of the Diels-Alder adduct.View full abstractDownload PDF (825K) -
Jer-Huei LIN, Takashi TANAKA, Gen-ichiro NONAKA, Itsuo NISHIOKA, Ih-Sh ...1990 Volume 38 Issue 8 Pages 2162-2171
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTogether with ten hydolyzable tannins and related compounds (1-10), three novel dimeric ellagitannins, excoecarianin (11), and excoecarinins A (13) and B (16), possessing a dehydrohexahydroxydiphenoyl or an elaeocarpusinoyl group, have been isolated from the leaves of Excoecaria kawakamii HAYATA (Euphorbiaceae). The structures of these tannins were established on the basis of spectroscopic and chemical evidence.View full abstractDownload PDF (1209K) -
Jean-Francois LAGORCE, Anne-Catherine JAMBUT-ABSIL, Jacques BUXERAUD, ...1990 Volume 38 Issue 8 Pages 2172-2174
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has been demonstrated spectroscopically that many nitrogen-containing heterocyclic compounds can from charge transfer complexes with iodine. The complexes of morpholine with iodine were shown to be of the n-σ type with a 1 : 1 stoichiometry. A strong donor-acceptor interaction was found (Kc=1261±12 mol-1 at 20°C in CCl4), considerably higher than those of complexes of anomatic compounds with iodine. The high value of the formation constant for this complex indicated that morpholine could serve as a starting point for the synthesis of novel anti-thyroid drugs.View full abstractDownload PDF (465K) -
Akira ANDO, Tetsuro SHINADA, Shinji KINOSHITA, Noriko ARIMURA, Mayumi ...1990 Volume 38 Issue 8 Pages 2175-2178
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of obtaining a porphyrin derivative useful for diagnosis and therapy of cancer, fluorine analogues of protoporphyrin, in which the vinyl group(s) were replaced by difluorovinyl group(s), were synthesized by the reaction of the formylporphyrins with sodium chlorodifluoroacetate in the presence of triphenylphosphine. Some improvements in the reported procedures for the synthesis of formylporphyrins are also described. Preliminary results of biological tests of the products showed that 82, 82-difluoroprotoporphyrin accumulates to gastric cancer more selectively than other fluorine analogues and that 32, 32, 82, 82-tetrafluoroprotoporphyrin is taken up by rat hepatoma cells more readily than the others.View full abstractDownload PDF (634K) -
Yuji NOMOTO, Hiroyuki OBASE, Haruki TAKAI, Masayuki TERANISHI, Joji NA ...1990 Volume 38 Issue 8 Pages 2179-2183
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of phthalazine and 1, 2, 3-benzotriazine derivatives which have heterocyclylpiperidino groups was synthesized and tested for cardiotonic activity in anesthetized dogs. Several 6, 7-dimethoxyphthalazine derivatives showed relatively potent cardiotonic activity comparable to that of amrinone.View full abstractDownload PDF (674K) -
Qian LIU, Shuichi HIRONO, Ikuo MORIGUCHI1990 Volume 38 Issue 8 Pages 2184-2189
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUsing the discriminant analysis method, we completely distinguished 24 calmodulin inhibitors in three groups, as classified by Zimmer et al. The resultant discriminant functions distinguished the three groups in terms of positive potential surface area on the side chain, as well as the total and neutral surface areas on the ring in the inhibitor molecules.Group assignment of additional calmodulin inhibitors from other sources was then estimated according to the discriminant functions. The relationship between structure and inhibitory potency on calmodulin-activated phosphodiesterase for group I inhibitors, together with those estimated, was studied using the adaptive least squares method with several parameters dependent on molecular conformations. A "best conformer" was selected for each inhibitor on the basis of quantitative structure-activity relationship (QSAR). The results of QSAR analysis of group I inhibitors showed that bydrophobicity was important for the ring moiety but not for the side chain. The negative potential surface area of the side chain is necessary for activity. It is desirable for the nitrogen atom in the side chain, which is considered the center of the negative potential area, to be located far from the ring moiety. Thus, the ring moiety and side chain may possibly play different roles in interactions with the receptor system.View full abstractDownload PDF (799K) -
Yoshiro NISHIMURA, Tohru HIROSE, Hidetsugu OKADA, Koh-ichiro SHIBAMORI ...1990 Volume 38 Issue 8 Pages 2190-2196
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of C-7 thio-substituted 1-cyclopropyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids were prepared and tested for their antibacterial activity. Structure-activity relationships associated with the C-5 and C-7 substituents were discussed. Among the C-7 substituents including alkylthio, arylthio, heteroarylthio, and cyclic aminothio groups, a 2-aminoethylthio group was the best for enhancing in vitro antibacterial activity. The C-5 variants increased activity in the order OH<F<H<NH2. Of compounds prepared in this work, 5-amino-7-(2-aminoethyl)thio-1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxo-quinoline-3-carboxylic acid (18) was the most active.View full abstractDownload PDF (883K) -
Hiroki FUJITA, Yusuke SASAKI, Hiroyuki KOHNO, Yasuhiro OHKUBO, Akihiro ...1990 Volume 38 Issue 8 Pages 2197-2200
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNine analogs based on a structure of Tyr-D-Arg-Phe-X (X=alkylamides or alkylhydrazide containing electoron-withdrawing atoms or groups) were newly synthesized and their biological properties were examined by the opioid receptor binding properties of μ-, δ- and κ-receptors, guinea-pig ileum (GPI) assay and analgesic activity in the tail pinch test after subcutaneous administration in mice. Analogs with X=NHCH2CF3, Sar-ol, or NH(CH2)2CN showed potent activities in the GPI and analgesic assays and high affinity for μ-receptor. An analog with X=taurinamide was found to possess 4-fold higher μ-receptor selectivity than that of [D-Ala2, MePhe4, Gly-ol5]enkephalin (DAGO). The receptor binding properties of previously reported analogs [Chem. Pharm. Bull., 33, 1528 (1985); ibid., 33, 4865 (1985); ibid., 36, 4834 (1988)] were also examined for overall discussion of the structure-activity relationships of this series of tripeptide amides.View full abstractDownload PDF (618K) -
Mayumi ITO(nee SOMEYA), Hiroshi SHIMURA, Naoharu WATANABE, Masaharu TA ...1990 Volume 38 Issue 8 Pages 2201-2203
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSuccessive purification of the extract from Canarium album and Euphorbia nematocypha, guided by antihepatotoxic activity in primary cultured rat hepatocytes, led to the isolation of brevifolin (1), hyperin (2), ellagic acid (3) and 3, 3'-di-O-methylellagic acid (4) as hepatoprotective compounds. Compounds 1, 3 and 4 also reduced carbon tetrachloride (CCl4)-induced liver damage in mice. The hapatoprotective activities of 1, 2, 3 and 4 in vitro and in vivo are apparently due to their antioxidative effects, which were exhibited by further studies using 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals and CCl4-induced lipid peroxidation systems.View full abstractDownload PDF (586K) -
Yoshiki MINO, Hideko USAMI, Nagayo OTA, Yoshio TAKEDA, Teruyoshi ICHIH ...1990 Volume 38 Issue 8 Pages 2204-2207
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInorganic constituents of the leaves of several kinds of plants growing on different soil types were investigated using energy-dispersive X-ray fluorescence spectrometry.The results can be summarized as follows : (1) Each plant exhibited a characteristic metals profile, even if they were grown on similar soil types. (2) As we would expect, the metals profile of the plant leaves depends on the inorganic constitution of the soil on which it is grown. However, the degree of the influence of the soil types on the metals profile of the plant differs according to the kind of inorganic element; Ca and Cu are almost indepenent of the soil types, but the Ti and Fe content is dependent upon the soil types. (3) Sr content of plant leaves is closely related to the ratio of Sr to Ca of the soil on which the plants are grown. (4) This information should be helpful in identifying the producing district or original plant of a crude drug by its metals profile.View full abstractDownload PDF (645K) -
Yoshiki MINO, Nagayo OTA1990 Volume 38 Issue 8 Pages 2208-2211
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnergy-dispersive X-ray fluorescence spectrometry following sample decomposition and preconcentration was developed to determine selenium in crude drugs. Samples were decomposed with conc. HNO3 and conc. H2SO4 in a flask with a reflux condenser. Evaporation of HNO3 had to be avoided to prevent serious loss of this element. Selenium was preconcentrated from the digestion liquid by two-step reduction with 4 M HCl and ascorbic acid, the elemental selenium formed was adsorbed on activated carbon and then collected on a Nuclepore membrane filter for direct irradiation in an X-ray spectrometer.This analytical method (detection limit, 0.03 ppm) was used to determine selenium in many kinds of crude drugs. The analytical results indicated vegetable drugs to be low in selenium content : more than 0.5 ppm in only a limited number of samples and less than detection (0.03 ppm) in nearly all the samples. Animal drugs contain selenium at higher levels, Lumbricus and Cantharis being 7.46 and 1.67 ppm, respectively.View full abstractDownload PDF (676K) -
Kyoji YOSHINO, Mitsuaki SANO, Masahiro FUJITA, Isao TOMITA1990 Volume 38 Issue 8 Pages 2212-2215
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of vitamin E (E) deficiency on the formation of aliphatic aldehydes in rat plasma and liver were studied. Three-week-old Wistar male rats were fed either an E supplemented diet (2-ambo-α-tocopheryl acetate 20 mg/kg diet, designated as E supplemented diet group) or an E deficient diet (E deficient diet group). After 8 weeks, n-hexanal and (E)-4-hydroxy-2-nonenal (4-HN) in the plasma of the E deficient diet group were found to be 2.0 and 2.5-fold greater than those of the E supplemented diet group, respectively. The contents of aldehydes such as n-pentanal, n-hexanal, 4-HN in the liver were also significantly higher in the E deficient diet group than in the E supplemented diet group. These results indicate that some aldehydes, arising possible from lipid peroxides, are produced and detected in the plasma and liver of rats under the condition like E deficiency.In this study we further found that the activity of the liver aldehyde dehydrogenase (ALDH, EC 1.2.1.3) was significantly changed; 5 and 8 weeks after the start it was lower in the E deficient diet group when compared to that in the E supplemented diet group. The decrease of enzyme activity was related to the increase of aldehydes such as n-hexanal in the liver.The aldehyde increase in the plasma of the E deficient diet group was thought to raise the injury of cells, namely, a strong hemolysis on erythrocytes prepared from the blood of rats fed the E deficient diet.View full abstractDownload PDF (677K) -
Seiichi MORI, Masayoshi YAMAGUCHI1990 Volume 38 Issue 8 Pages 2216-2218
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of regucalcin, a calcium-binding protein isolated from rat liver cytosol, on cytosolic Ca2+/calmodulin-dependent protein kinase activity was investigated. The increase in cytosolic Ca2+/calmodulin-dependent protein kinase activity with passage of incubation time was clearly prevented by the presence of regucalcin (1.0 μM). An appreciable effect of regucalcin was seen at 0.5 μM. The cytosolic Ca2+/calmodulin-dependent protein kinase activity was fairly increased by increasing concentrations of added Ca2+ (0.25-1.0 mM). This increase was clearly blocked by the presence of regucalcin (1.0 μM). The inhibitory effect of regucalcin on the protein kinase activity was also seen with varying concentrations of calmodulin (2.5-15 μg). In the presence of regucalcin (1.0 μM), trifluoperazin (50 μM), an antagonist of calmodulin, significantly decreased the cytosolic Ca2+/calmodulin-dependent protein kinase activity. These results suggest that regucalcin can regulate the Ca2+-calmodulin effect in liver cytosol.View full abstractDownload PDF (601K) -
Hisami SHINOHARA, Naohito OHNO, Toshiro YADOMAE1990 Volume 38 Issue 8 Pages 2219-2223
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe have demonstrated that hot water extracts of sclerotia of Sclerotinia sclerotiorum IFO 9395 (TSHW) show various immunomodulating activities and mitogenic substance(s) were recovered from the β-1, 3-glucanase resistant-fraction (EDF) (Shinohara et al. Chem. Pharm. Bull., 37, 2174 (1989)). In this paper, we examined whether or not the mitogenic substance(s) were also obtained from the other methods, phosphate buffer extraction. Although the native extracts (3S-M) sterilized with a membranse filter showed a slight mitogenicity to murine splenocytes, 3S-M denatured in boiling water (3S-MB) showed significant activity. Treatment of 3S-M for only 1 min in boiling water or 10 min at 70 °C was sufficient to show significant mitogenic activity. After heat treatment of 3S-M in boiling water for 30 s, the main band corresponding to that of 3S-M was not clearly observed. Instead, new bands appeared at the top of the gel in normal-polyacrylamide gel electrophoresis (normal-PAGE), suggesting that many physicochemical changes occurred during that heat treatment. These findings suggest that heat denaturation of substance(s) from sclerotia was one of the triggering mechanisms expressing mitogenic activity to murine splenocytes.View full abstractDownload PDF (1267K) -
Hiroaki MIZUTA, Yasushi KAWAZOE, Keiichiro HAGA, Kenji OGAWA1990 Volume 38 Issue 8 Pages 2224-2227
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of the amount and the composition of meals on gastric emptying and small intestinal transit times of a suspension were investigated in beagle dogs using acetaminophen and salicylazosulfapyridine as markers.Gastric emptying time was affected both by the amount and the composition of a meal; it was prolonged proportionally to the amount of a solid meal and varied among the 3 kinds of test meals of the same energy content in the following rank order : land>skimmed milk>mashed potatoes.The inter-individual variation of small intestinal transit time in a fed state was smaller than that in a fasted state, whereas the mean transit times in both states were similar. Small intestinal transit time was not affected by the amount of the solid meal. On the other hand, it varied among the 3 kinds of test meals in the following rank order : lard>mashed potatoes>skimmed milk.It is noteworthy that small intestinal transit time in the beagle dog is approximately 2 h shorter than that in humans both in fasted and fed states.View full abstractDownload PDF (599K) -
Yukio SATO, Koichi NAKAJIMAYA, Yasuo SUZUKI1990 Volume 38 Issue 8 Pages 2228-2232
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInteraction of liposomes (phospholipid vesicle) with human erythrocytes was studied by means of a spectroscopic method. Transfer of hemoglobin between liposomes and erythrocytes was observed. This transfer was mediated by a migration of band 3 proteins. In this case, a transfer of band 4.5 also was observed by means of electrophoresis. An interaction of lipid monomers from the liposomes with the erythrocyte membranes seemd to be closely correlated to the transfer of these proteins. It was presumed that this interaction induced some changes in the molecular organization of the cell membranes around band 3, resulting in release of the proteins from the erythrocyte membranes.View full abstractDownload PDF (1005K) -
Satit PUTTIPIPATKHACHORN, Etsuo YONEMOCHI, Toshio OGUCHI, Keiji YAMAMO ...1990 Volume 38 Issue 8 Pages 2233-2236
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of grinding on the dehydration of crystal water of theophylline has been studied. It was observed that the water content of theophylline hydrate decreased with increased grinding time. As the grinding time proceeded, the results of differential scanning calorimetry (DSC) indicated that crystal water of ground theophylline hydrate dehydrated in three steps at ca. 58, 44, and 17°C, respectively. Powder X-ray diffraction study revealed that the crystal lattice of theophylline monohydrate collapsed by grinding, and part of the theophylline molecules subsequently rearranged the collapsed lattice to form theophylline anhydrate. The result of Fourier transformed infrared spectroscopy demonstrated that the hydrogen bonds between crystal water molecules and theophylline molecules were weakened or destroyed to some extent by grinding. It was supposed that crystal water in the ground theophylline hydrate might exist at least in three molecular states of different hydrogen-bonding. From DSC study, it was suggested that the ruptured hydrogen bonds of water molecules in the ground theophylline hydrate were strengthened after storage under 96.5% relative humidity at 30°C.View full abstractDownload PDF (643K) -
Makiko FUJII, Katsuhiro HARADA, Mitsuo MATSUMOTO1990 Volume 38 Issue 8 Pages 2237-2241
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe prepared a phenobarbital (PB) solid dispersion (SD) with phosphatidylcholine (PC). PB was present in an amorphous state in SD if its mole fraction was under 0.75. An infrared (IR) spectra study suggested a hydrogen bond between NH in PB and phosphate in PC, with a raito of about 1 : 1. When the mole fraction of PB was less than 0.50, differential scanning calorimetry (DSC) curves showed endothermic peaks at 57, 90 and 145°C, and an exothermic peak at 60°C. The IR spectrum and X-ray diffraction pattern changed after holding at 70°C, so at this point it is considered that the metastable state of SD changed into a ctable, and extra energy was released. When the mole fraction of PB was high, PB also arranged near hydrophobic group because an endothermic peak was observed at 46-52°C, which was lower than fully hydrated PC.PB is similar to indomethacin (IM) in molecular shape and to phenyton (PHT) in chemical structure. Its DSC curve and IR spectra are similar to PHT, and the limit ratio of its amorphous state is the same as IM. It is considered that the chemical structure is an important factor in its interaction to PC, and also, the molecular shape is important to arrange into PC lattice.View full abstractDownload PDF (761K) -
Daisuke TESHIMA, Akito SUZUKI, Kenji OTSUBO, Shun HIGUCHI, Toshinobu A ...1990 Volume 38 Issue 8 Pages 2242-2245
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe efficacy of both the emetic syrup prepared in the previous report and the United States Pharmacopoeia (USP) ipecac syrup concerning the prevention of drug absorption was investigated in 4 beagle dogs using a randomized and cross-over design. In order to control the intragastric pH of the beagle dogs, the administration of pentagastrin or hydrochloric acid (HCl)-glycine buffer (pH 1.5) was tested. The intragastric pH changed from 7.2 to 1.8 with the intramuscular administration of pentagastrin, but the primary emesis occurred more slowly. On the other hand, the HCl-glycine buffer (pH 1.5) gave the appropriate emesis. Therefore, the HCl-glycine buffer (pH 1.5) was used to control the intragastric pH of the beagle dogs.Acetaminophen (AcA), salicylic acid (SA) and kanamycin (KM) as markers were administered orally after conditioning the intragastric pH at 1.5. The emetic syrup or the USP ipecac syrup was then administered. The recovery rate of AcA and KM from vomit was 42-65%. The emetic syrup and the USP ipecac syrup significantly reduced the absorption of AcA from the calculation of pharmacokinetic parameters compared to the control syrup. It was observed that the absorption of cephaeline (CP) in the emetic syrup was less than that of CP in the USP ipecac syrup.View full abstractDownload PDF (684K) -
Satoru TANI, Tohru TANAKA1990 Volume 38 Issue 8 Pages 2246-2248
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of somatostatin on pepsinogen secretion was investigated in the rat in vivo and in vitro. In the perfused rat stomach, somatostatin inhibited secretagogue-induced acid secretion in dose-dependent manner. However, effects of somatostatin on secretagogue-induced pepsinogen secretion were obscure. To clarify the effects of somatostatin on the chief cells, gastric mucosal cell were isolated by a proteolytic enzyme. Somatostain inhibited carbachol- and cholecystoknin octapeptide-induced pepsinogen secretion from dispersed gastric mucosal cells in a dose-dependent manner. Histamine-induced pepsinogen secretion, which was recovered by culturing, was also inhibited by somatostatin. These results suggest that somatostatin inhibits secretagogue-induced pepsinogen secretion directly.View full abstractDownload PDF (572K) -
Shoko YOKOYAMA, Tadao FUJIE1990 Volume 38 Issue 8 Pages 2249-2252
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe association of 1-octadecanoic acid (C18) in 1, 2-dichloroethane at 40°C has been investigated by measuring the fluorescence spectra and intensities of ammonium 8-anilino-1-naphthalenesulfonate as a probe.As a result, it has been found that C18 begins to associate at a concentration of 1.0-1.2×10-2 mol·dm-3 and that the aggregation number is small and constant in the concentration region above about 4×10-2mol·dm-3.The mechanism for the formation of fatty acid (FA)-thiamine disulfide (TDS) complexes, (FA)6(TDS), was also discussed.View full abstractDownload PDF (680K) -
Osamu MATSUMOTO, Tooru TAGA, Masaaki MATSUSHIMA, Tsuneyuki HIGASHI, Ka ...1990 Volume 38 Issue 8 Pages 2253-2255
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal of bovine trypsin complexed with a potent inhibitor, 4-[4-(N, N-dimethylcarbamoylmethoxycarbonylmethyl)phenoxycarbonyl]guanidinium methanesulfonate (FOY-305) in the novel orthorhombic from with a low molecular packing density was studied by the X-ray diffraction method. Using synchrotron radiation, the intensity data were collected to 1.8 Å resolution. The structure was solved by molecuar replacement methods, and refined to an R-factor=18.0% for 14364 reflection by the restrained least-squares method. The final difference Fourier maps revealed that hydrolyzed inhibitor fragments bind with the protein at multiple sites around the active center of trypsin. The structural feature in the crystalline state probably corresponds to a statistical average of several complexes which would be formed between the inhibitor and trypsin during the binding and releasing process in solution.View full abstractDownload PDF (578K) -
Toyoshi KATAGI, Misako AOKI, Sachiko KATSU, Hiromi KATAOKA, Tomoko HAN ...1990 Volume 38 Issue 8 Pages 2256-2258
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFlavone was reduced with sodium bis(2-methoxyethoxy)aluminum hydride (SMEAH) to 1-(2-hydroxyphenyl)-3-phenylpropanol (A) and 1-phenylindan-1, 3-diol (B). Product yields depended on the molar ratio of SMEAH/flavone. When the molar ratio of SMEAH was from 1 to 2 in relation to flavone, the main product was compound A, but at a ratio of more than 3, the rearranged compound B was predominant.View full abstractDownload PDF (533K) -
Kiyotaka KOYAMA, Sumiko AIDA, Shinsaku NATORI1990 Volume 38 Issue 8 Pages 2259-2261
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEpimerization reactions of bis(naphtho-γ-pyrone) derivatives, ustilaginoidin A (2) and dihydroisoustilaginoidin A (6), were examined by refluxing the compounds in acetic and in p-xylene. The epimerization occurred in acetic acid but not in p-xylene. From the reaction mixture in the case of dihydroisoustilaginoidin A, the starting material and the epimer at the biaryl linkage, dihydroustilaginoidin A (7), were isolated and characterized. The circular dichroism Cotton effects due to chiral exciton coupling of biaryl compound is discussed.View full abstractDownload PDF (521K) -
Jun-ichi SAKAKI, Satoshi KOBAYASHI, Masayuki SATO, Chikara KANEKO1990 Volume 38 Issue 8 Pages 2262-2264
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new general one-pot method for high-yield synthesis of S-alkyl β-ketothioesters by heating of 6-mono- and 5, 6-disubstituted 1, 3-dioxin-4-ones and thiols in an appropriate aprotic solvent is described. This procedure is available for large-scale preparation of a variety of β-ketothioesters.View full abstractDownload PDF (418K) -
Yasuo TAKEUCHI, Tominari CHOSHI, Hideo TOMOZANE, Hirokazu YOSHIDA, Mas ...1990 Volume 38 Issue 8 Pages 2265-2267
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Wittig reaction of benzofuran-2, 3-diones (2), cyclic α-ketoesters, was examined. The reaction of 2 having an electron-donating substituent on the aromatic ring with a stable ylide afforded not 3-alkylidene-2(3H)-benzofuranones (4) but 2-alkylidene-3(2H)-benzofuranones (1) with high regioselectivity.View full abstractDownload PDF (582K) -
Yoshino NISHIGUCHI, Noriko TAGAWA, Fukuko WATANABE, Toshiko KIGUCHI, I ...1990 Volume 38 Issue 8 Pages 2268-2270
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 4-carboxymethylthio derivatives 8 and 13, new haptens of betamethasone (2) and dexamethasone (1), were prepared for application to enzyme immunoassay.View full abstractDownload PDF (591K) -
Kenji SAKAGAMI, Katsuyoshi IWAMATSU, Kunio ATSUMI, Minoru HATANAKA1990 Volume 38 Issue 8 Pages 2271-2273
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthesis and antibacterial activity of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methyl)ethoxyiminoacetamido]-3-(3-hydroxy-4-pyridon-1-yl)-3-cephem-4-carboxylic acid (12) and its related compounds are described. Compound 12 exhibited excellent antibacterial activity against gram-negative bacteria, and its anti-pseudomonal activity was ten to fifteen times greater than that of ceftazidime.View full abstractDownload PDF (527K) -
Hiroshi YOSHINO, Yoshihiro ARAKAWA, Takahiro NAKAZAWA, Takeru KANEKO, ...1990 Volume 38 Issue 8 Pages 2274-2276
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe opioid activities of [MeTyr1]-Dyn(1-7)-NH2, [MeTyr1, D-Leu8]-Dyn(1-8)-NH2, [MeTyr1, D-Leu8]-Dyn(1-9)-NH2, [MeTyr1, D-Leu8]-Dyn(1-10)-NH2, [MeTyr1, D-Leu8]Dyn(1-11)-NH2, and [MeTyr1, D-Leu8, 12]-Dyn(1-13)-NH2 were examined in the bioassays (guinea pig ileum, mouse vas deferens and rabbit vas deferens). Because [MeTyr1, D-Leu8]-Dyn(1-9)-NH2 showed the most potent opioid activity of the peptides tested, the biological activities of two kinds of Dyn(1-9) analogues, [MeTyr1, MeArg7, D-Leu8]-Dyn(1-9)-NHEt and [D-Cys2-Cys5, MeArg7, D-Leu8]-Dyn(1-9)-NH2 were determined and compared with those of [MeTyr1, MeArg7, D-Leu8]-Dyn(1-8)-NHEt and [D-Cys2-Cys5, MeArg7, D-Leu8]-Dyn(1-8)-NHEt in the three bioassays, in the receptor binding assays, and in the mouse tail pinch test after subcutaneous administration. The results suggest that the extension of the C-terminal in the peptide chain of [MeArg7, D-Leu8]-Dyn(1-8)-NH2 analogues by Arg is ineffective for increasing the κ-opioid activities, κ-receptor selectivity and/or analgesic effects of the peptides.View full abstractDownload PDF (589K) -
Takeshi KATO, Yutaka MORITA1990 Volume 38 Issue 8 Pages 2277-2280
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix flavone C-glycosides : 2", 6"-di-O-acetylisoorientin (1), 2", 6"-di-O-acetylorientin (2), 2"-O-acetylisoorientin (3), 2"-O-acetylorientin (4), isoorientin (5) and orientin (6) were identified from the aerial parts of Rumex acetosa L .(Polygonaceae), in addition to two flavonol O-glycosides : avicularin (7) and hyperin (8). Of these, 1-3 were new compounds and 4-7 were isolated for the first time from this species. The structures were established by ultraviolet, fast atom bombardment mass and nuclear magnetic resonance spectral data.View full abstractDownload PDF (595K) -
Feng-E WU, Kazuo KOIKE, Tamotsu NIKAIDO, Kiyoshi ISHII, Taichi OHMOTO, ...1990 Volume 38 Issue 8 Pages 2281-2282
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new steroid, 22, 23-dihydrospinasterol plamitate was isolated from the whole plants of Arenaria kansuensis (Caryophyllaceae) and its structure was determined by chemical and spectroscopic means. 22, 23-Dihydrospinasterol, 22, 23-dihydrospinasterone, ergosterol-5, 8-peroxide, 24-methylene-22, 23-dihydrolanosterol, zeorin, fernenone, β-sitosterol 3β-O-β-D-glucopyranoside, tricin, (+)-isoscoparin and (-)-isoscoparin were also isolated.View full abstractDownload PDF (475K) -
Mineo SHIMIZU, Hisashi SHOGAWA, Takayasu MATSUZAWA, Sakiko YONEZAWA, T ...1990 Volume 38 Issue 8 Pages 2283-2284
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe anti-inflammatory active fraction of the Paraguayan crude drug, "Alhucema, " Lavandula latifolia VILL. afforded four compounds : coumarin (1), 7-methoxycoumarin (2), trans-phytol (3) and caryophyllene oxide (4). 1 showed a weakly inhibitory effect on carrageenin-induced paw edema in rats on topical application and 4 showed an inhibitory effect on histamine-induced contraction in guinea pig ileum.View full abstractDownload PDF (403K) -
Takako FURUKAWA, Yasuhisa FUJIBAYASHI, Masao FUKUNAGA, Akira YOKOYAMA1990 Volume 38 Issue 8 Pages 2285-2286
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo obtain radiogallium labeled immunoglobulin G with a high specific radioactivity for in vitro use, a 67Ga source was purified by extraction from 67Ga-gallium citrate with butyl acetate, and a 67Ga-labeling solution was produced. This solution was then used to label a deferoxamine-immunoglobulin G conjugate. Both a very high specific radioactivity(872±56 MBq/mg) and a high labeling efficiency (94.0%) were achieved.View full abstractDownload PDF (456K) -
Eisuke SATO, Michi YOSHIKAWA, Yuichi KANAOKA1990 Volume 38 Issue 8 Pages 2287-2289
Published: August 25, 1990
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe fluorescence of 9, 10-dioxa-syn-3, 4, 6, 7-tetramethylbimane (bimane) was found to be quenched in the presence of guanosine 5'-monophosphate. By using this phenomenon, the bimane system was used for the fluorophor of substrates for phosphodiesterase I.Bimanes were coupled to 5'-guanylic acid and the resulting compounds were shown to be portent fluorogenic substates for the assay of phosphodiesterase I.View full abstractDownload PDF (468K)