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Volume 90, Issue 9
Displaying 1-24 of 24 articles from this issue
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KATSUHIDE MATOBA, TAKAO YAMAZAKI1970 Volume 90 Issue 9 Pages 1061-1068
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS3-Alkoxy-5, 5-dimethyl-2-cyclohexenones were reduced to trans-3-alkoxy-5, 5-dimethyl-cyclohexanols over Raney-nickel in ethanol in over 90% yield. In the case of 2-methyl-3-ethoxy-5, 5-dimethyl-2-cyclohexenone and 2-butyl-3-methoxy-2-cyclopentenone, a large amount of the starting materials was recovered. On the other hand, two methyl vinylogous esters of 2-methyl-4-hydroxy-1, 3-cyclopentanedione were reduced to the corresponding tetrahydro compounds and demethoxy perhydro compounds.View full abstractDownload PDF (779K) -
AKITADA NAKAMURA, SHOZO KAMIYA1970 Volume 90 Issue 9 Pages 1069-1075
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSNuclear magnetic resonance (NMR) spectra of 1-hydroxy-2, 3, 5, 10-tetrahydro-1H-pyra-zolo[1, 2-b]phthalazine-5, 10-diones (Ia-d) and their 2-bromo derivatives (IVa-d) were determined in order to elucidate stereospecificity in this type of ring-chain tautomerism. The vicinal coupling constants of trans and quasi-equatorially situated protons (J-trans-eq.) are 0-2.70 cps, J-cis 4.50-9.90 cps, and J-trans-ax. 7.35 -12.00 cps. From the magnitude of J vic. it was concluded that Ib (Ic) having a CH3(C8H5) group at the 3-position, exists predominantly as V(VI) with an envelope conformation in which the CH3(C6H5) group and the OH group are present as cis and quasi-axial. This stereospecific, intra-molecular addition of the lactam-NH to the aldehyde-CO function could be explained by a steric repulsion between the CH3(C6H5) group and the lactam-CO group at the 5-position.View full abstractDownload PDF (645K) -
SEIGO FUKUSHIMA, YUKIO AKAHORI, IKUNORI SAKAMOTO, KAZUKO NORO(SHIMIZU) ...1970 Volume 90 Issue 9 Pages 1076-1080
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSCatalytic reduction of 2-methyl-4-phenyl-3H-1, 5-benzodiazepine (IV) gave 2-methyl-4-phenyl-2, 3, 4, 5-tetrahydro-1H-1, 5-benzodiazepine (V) which was assumed to be a mixture of two kinds from nuclear magnetic resonance data but was not separated by various means. Similar reduction of 2, 4-diphenyl-3H-1, 5-benzodiazepine (VI) gave two kinds of tetrahydro compound which were assumed to be a cis and trans isomers from their nuclear magnetic resonance spectra. On the other hand, reduction of 2-oxo-4-phenyl-2, 3-dihydro-1H-1, 5-benzodiazepine (X) with lithium aluminum hydride also gave 2-phenyl-2, 3, 4, 5-tetrahydro-1H-1, 5-benzodiazepine (XI). These tetrahydrobenzodiazepines are new compounds.View full abstractDownload PDF (532K) -
MUNEHARU OGAWA, SUEO HISADA, ISAO INAGAKI1970 Volume 90 Issue 9 Pages 1081-1087
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA natural flavan glucoside, koaburanin, was isolated from the leaves of Enkianthus nudipes (HONDA) OHWI. This compounds was found to be (2R)-5, 7-dihydroxyflavan-7-glucoside on the basis of chemical and spectroscopic evidences. This is apparently the first time that this flavan glucoside was obtained from a natural source having a heterocyclic structure without an oxygen atom.View full abstractDownload PDF (824K) -
MASAYUKI NAKAGAKI, NORIAKI FUNASAKI, MISAO NISHINO1970 Volume 90 Issue 9 Pages 1088-1094
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSurface pressure-area and specific water evaporation resistance -surface pressure curves were obtained for the monolayers of aluminum stearates of various composition. The pressure-area curves varied with time at which the monolayers were spread after the dissolution of aluminum stearates in benzene or chloroform. Both curves, however, became nearly constant and identical when they were measured two days after the dissolution. The mono-and 1.5-soaps were unstable liquid-condensed films, while the diand 2.5-soaps were solid-condensed films. The stability of these monolayers decreased in the order of 2.5>di>1.5>mono, following the decrease of hydrophobic character of these compounds from which monolayers were formed. Specific evaporation resistance was measured as a function of surface pressure by the desiccant method. Specific resistance of monolayer of aluminum distearate, which was spread from either benzene or chloroform, was identical. Specific resistance of monolayer of the 1.5-soap was greater than the value calculated by mixture rule as a mixture of the monosoap and the disoap, while that of the 2.5-soap was smaller than that as a mixture of disoap and stearic acid. These deviations were explained on the basis of the intermolecular interaction.View full abstractDownload PDF (772K) -
EIGO TAKABATAKE1970 Volume 90 Issue 9 Pages 1095-1099
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe effect of N-ethylmaleimide (NEM) on the epinephrine-induced activation of phosphorylase in diaphragm and that of lipolysis in epididymal fat pad in male rats was examined. When the isolated diaphragm was preincubated with NEW, 1 mM, epinephrine could not activate the phosphorylase. The activation of phosphorylase b kinase was also inhibited by the preincubation with NEM. The partially purified phosphorylase b kinase preparation was more rapidly inactivated by NEM than phosphorylase b crystals. The activation of lipolysis by in vitro epinephrine in adipose tissue or isolated fat cells was blocked by NEM or SH-blocking agents. The effect of ACTH was also inhibited by NEM. The inhibitory effect of NEM was not restored by the addition of glutathione 10 seconds after the fat cells were contacted with NEM. Thus, NEM probably changes the quality of tissue to block the action of epinephrine.View full abstractDownload PDF (603K) -
MARI SAKUMA, SHIGEMI AWATAGUCHI, YOSHISHIGE SATO1970 Volume 90 Issue 9 Pages 1100-1106
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSWhole body autobacteriography was proposed as an experimental method to follow distribution and localization of pathogenic microbes in experimentally infected animals. In the present studies, experimental staphylococcosis in mice was studied by this method. Mice were infected with Smith -diffuse strain of Staphylococcus aureus by intravenous or intraperitoneal route. Whole body sections of 40 μ in thickness were obtained in sterile condition with a cold microtome at various intervals after infection. These sections were immediately (or after freeze drying) placed on agar plates and incubated at 37°over-night. The sections were then treated with triphenyltetrazolium chloride for vital staining. The autobacteriograms after intravenous infection demonstrated a rapid disappearance of the microbes from the blood stream and their accumulation in the spleen, liver and lung. They also revealed the extensive staphylococcal multiplication in the kidney, causing abscess 24 hours later. These informations do not conflict with the results obtained by usual microbiological techniques. The distribution and localization of staphylococci in mice infected intraperitoneally were also evaluated by autobacteriography when mice were treated with tetracycline or penicillin immediately after infection. The advantages of this method are discussed.View full abstractDownload PDF (3651K) -
Studies on Change of Apparent Density of Pharmaceutical Powders by Means of adding Lubricant PowdersYASUO MIYAKE, CHIKAE SADAKATA, KIMIO TATSUISHI, SHYOJI TOYOSHIMA1970 Volume 90 Issue 9 Pages 1107-1112
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSGenerally, lubricants are added into pharmaceutical powders in order to improve their fluidity, packing property and others. The present experiment was carried out to eluci-date the mechanism of such lubricant actions. The state of lubricated powders was followed by measuring apparent density of the powders, and by observing them with an electron microscope. 1) Lubricating mechanism of talc, or synthetic aluminum silicate is a diffusion phenomenon or diffusion-adhesion phenomenon of the lubricant particles to particles of pharmaceutical powder. In the case of calcium stearate, the lubricating mechanism is considered to consist of two phenomena; diffusion-adhesion phenomenon and trasformation-coating phenomenon of calcium stearate particles to particles of pharmaceutical powder. Namely, at the first state of lubricant-mixing, the diffusion-adhesion mainly occured, and after that, with increase of cumulative revolution number of the mixer, the transformation-coating phenomenon of calcium stearate adhered to particle surface of pharmaceutical powder occurred. 2) In the operation of mixing and lubricating pharmaceutical powder with calcium stearate in V-type mixer, the relationship between changing rate of apparent density of the powder and cumulative revolution number of the mixer is exponential and fits well the experimental equation 2.View full abstractDownload PDF (1126K) -
MASAITI YASUE, NORIHISA KAWAMURA, JINSAKU SAKAKIBARA1970 Volume 90 Issue 9 Pages 1113-1117
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn a previous work, a new compound, innovanoside, was extracted from the leaves of Evodiopanax innovans and the structure was concluded as maltol glucoside 6-cis-p-coumarate, which was converted by alkali to isoinnovanoside, maltol glucoside 6-trans-p-coumarate. The methyl ether of isoinnovanoside was synthesized from maltol glucoside via 2, 3, 4-tris(trimethyl)silyl ether and its p-methoxy-trans-cinnamate. Both the synthesized and natural isoinnovanoside methyl ether consumed two moles of sodium periodate but innovanoside methyl ether consumed only one mole of periodate. Thus the position or the acid group in innovanoside must be 2 or 4 in sugar moiety. Since acylmigration from 4-to 6-position by alkali is well known, the structure of innovanoside should be revised as maltol glucoside 4-cis-p-coumarate. From the water-soluble part of the methanol extract of the leaves scyllitol, quinic acid, and syringin were also isolated.View full abstractDownload PDF (638K) -
MASAYUKI NAKAGAKI, HIROSHI KISHIMOTO, KOICHIRO HIRANO1970 Volume 90 Issue 9 Pages 1118-1125
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSurface chemical properties of disodium and dipotassium monocetyl phosphates (CPNa2 and CPK2, respectively) were studied mainly by the measurement of surface tension of their aqueous solution with variously added alkali (NaOH, KOH). The theory of Gibbs' adsorption was examined for the case of uni-bivalent-type CP-salts in the presence of a uni-univalent electrolyte, and the surface excess concentration (r) and the area/molecule (A) of CP-salts in adsorbed monolayers were calculated. It was thereby found that r of CPNa2 is larger than that of CPK2, and that the cmc and the surface tension at cmc (γcmc) of CPNa2 are smaller than those of CPK2. The difference of surface chemical properties between CPNa2 and CPK2 is attributed to the lower water solubility of CPNa2 than CPK2, which would result in easier adsorption and micelle formation. Counter-ion dependence of r was similar not to dodecyl sulfate but to stearic acid.View full abstractDownload PDF (807K) -
HIROSHI IMAMURA, EIICHI MATSUI, YASUYUKI KATO, TETSUYA FURUTA1970 Volume 90 Issue 9 Pages 1126-1134
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDistribution of 35S-labeled 2-amino-3-ethoxycarbonyl-6-benzyl-4, 5, 6, 7-tetrahydrothieno-[2, 3-c]pyridine (35S-Y-3642) in mice and rats was investigated. When this compound was given to mice, the highest tissue level of radioactivity was observed at after 30 minutes and radioactivity was highly distributed in the liver, brawn fat, Harderian gland, bile, gastrointestinal tract, and urine. 35S-Y-3642 was mainly distributed without debenzylation in mouse tissues with the exception of the lung, and more than 80% of radioactivity in the brain and brawn fat was found to be in unchanged form. When this compound was given to rats, tissue level of radioactivity increased slowly and was highly distributed in the liver, kidney, peripheral fat, lung, adrenals, and spleen. Almost all of radioactivity in the peripheral fat was identified as unchanged form, but most of radioactivity in other tissues of rats was debenzylated metabolites of 35S-Y-3642. These results revealed that 35S-Y-3642 absorbed from the administration sites was incorporated in the adipose tissue and then re-mobilized to other tissues, and that the debenzylated metabolites contributed to the anti-inflammatory actions of the original compound in rats. Binding with serum protein of 35S-Y-3642 and its radioactive metabolites was relativelv low and no remarkable accumulation of these compounds was observed in the carrageenin-induced edema of rats.View full abstractDownload PDF (1936K) -
HIDEAKI SHIRAI, TAMOTSU YASHIRO, TAIKI AOYAMA1970 Volume 90 Issue 9 Pages 1135-1139
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFor the purpose of testing the biological activity, spiro[4-hydroxycycloalkane-1, 4'-2', 3'-dihydro-6'-methoxy-2'-methyl1'H-isoquinoline]derivatives (IV and V) were synthesized by cyclization of 1-(m-methoxyphenyl)-4-hydroxycyclohexanemethylamine (XIII) or 1-(m-methoxyphenyl)-4-hydroxycycloheptanemethylamine (XX) under the conditions of Eschweiler-Clarke reaction. Spiro [4-hydroxycycloalkane-1, 4'-2', 3'-dihydro-6'-hydroxy-1'H-isoquinoline] derivatives (XII and XXII) were prepared by demethylation of IV or V with boron tribromide in dry dichloromethane.View full abstractDownload PDF (534K) -
SUMU MATSUEDA, YOSHIHIRO OTAKI1970 Volume 90 Issue 9 Pages 1140-1143
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA number of sesquiterpenelactones were isolated from mature plants of Artemisia feddei Lev. et Van. And Ar. douglasiana Bess. The majority of these lactones were found to be acetyl derivative has been reported to be present in young plants of the same species.View full abstractDownload PDF (498K) -
KAZUO ITO, HITOSHI TANAKA, TORU ITO, HIROSHI FURUKAWA1970 Volume 90 Issue 9 Pages 1144-1149
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSOur previous report described nuclear magnetic resonance spectra of 1-phenethyl-and 1-styryl-1, 2, 3, 4-tetrahydroisoquinoline derivatives. In the present series of work, these compounds (VII, VIII, XIII) were synthesized by the so-called Dobrovsky reaction and Bischler-Napieralsky reaction, followed by reduction with sodium borohydride and the application of formaldehyde and sodium borohydride. In order to assign aromatic protons at 5- and 8-positions of the isoquinoline ring in 7-hydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives, deuterium exchange reaction of aromatic proton was utilized but the corresponding deuterium compound of 1-styryl-6-methoxy-1, 2, 3, 4-tetrahydro-7-isoquinolinol (Vb') could not be obtained. This compound (Vb') was found to undergo isomerisation with alkali to XIV.View full abstractDownload PDF (589K) -
SHIGETAKA YOSHINA, AKIRA TANAKA, GANG-NAN YANG, HSING-CHIEN HSIU1970 Volume 90 Issue 9 Pages 1150-1155
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS2-Phenylfuran, 2-(nitrophenyl)furans, and 2-(nitrophenyl)furfurals were synthesized from aniline or nitroanilines and furan or furfural by the Meerwein reaction. The Wittig reaction of 2-(4-nitrophenyl)furfural and benzyltriphenylphosphonium chloride afforded two kinds of 5-(4-nitrophenyl)-2-(furylvinyl)benzene which were considered to be stereoisomers. This point was confirmed by various spectral measurements. Schiff bases were also prepared from 2-(nitrophenyl)furfurals.View full abstractDownload PDF (590K) -
EIICHI MATSUI, YASUYUKI KATO, TETSUYA FURUTA, HIROSHI IMAMURA1970 Volume 90 Issue 9 Pages 1156-1159
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn the previous experiments, it was proved that the orally administered 2-amino-3-ethoxycarbonyl-6-benzyl-4, 5, 6, 7-tetrahydrothieno[2, 3-c]pyridine (Y-3642) was debenzylated in rats and mice to 2-amino-3-ethoxycarbonyl-4, 5, 6, 7-tetrahydrothieno[2, 3-c]-pyridine (debenzyl-Y-3642). Benzyl moiety of Y-3642 was excreted as hippuric acid into urine. The same examination was made in men. Y-3642HC1 in a dose corresponding to 100 mg of Y-3642 was given orally to men and its metabolites in the urine were examined by thin-layer chromatography. Debenzyl-Y-3642, unchanged Y-3642, hippuric acid, and several unknown metabolites were detected. Quantitative studies on the metabolites showed a tendency for hippuric acid to increase in the urine. Y-3642 was found in unchanged form at about 0.6% of the administered dose in the urine by the dilution method using 14C-Y-3642. This result suggests that the metabolic fate of Y-3642 in men is quite similar to that in rats and mice.View full abstractDownload PDF (495K) -
MOTOMU SATO, TAKASHI TATSUNO, HISAYUKI MATSUO1970 Volume 90 Issue 9 Pages 1160-1163
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn relation to the racemization reaction of α-amino acid in nonaqueous acetic acid, the rate constants for the racemization of five neutral amino acids [Chemical formula] were kinetically investigated in glacial acetic acid and compared. Susceptibility of the tested amino acids to the acetic acid-induced racemization was found to decrease in the order of Ala>Leu>Phe>But>Val. This order, except Phe, was similar to the tendency observed in usual base-catalyzed racemization. The present results, combined with those reported in previous papers, 1, 5)suggest that acetate anion probably played a base-catalyst role in the present racemization reaction. In the case of Phe, however, another factor such as phenonium ion participation may be involved.View full abstractDownload PDF (495K) -
KAZUO ITO, HIROSHI FURUKAWA, MITSUOMASA HARUNA, MICHIE SATO1970 Volume 90 Issue 9 Pages 1163-1165
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe alkaloidal components of the seeds of a crude drug "Batore" (Aristolochiaceae) were examined and a phenolic aporphine alkaloid, asimilobine (IV) was isolated and characterized.View full abstractDownload PDF (423K) -
JUN-ICHI KUNITOMO, YOSHIKO NAGAI, YASUKO OKAMOTO, HIROSHI FURUKAWA1970 Volume 90 Issue 9 Pages 1165-1169
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSTertiary alkaloids in the leaves of domestic Nelumbo nucifera GAERTN. (Japanese name "Hasu") were examined and anonaine (V), pronuciferine (VI), N-nornuciferine (VII), liriodenine (IX), and D-methylcoclaurine (X) were newly isolated besides the known roemerine (I), nuciferine (II), O-norruciferine (III), and dl-armepavine (IV).3a)View full abstractDownload PDF (613K) -
KAZUO ITO, HIROSHI FURUKAWA, HITOSHI TANAKA, SHIGEKO KATO1970 Volume 90 Issue 9 Pages 1169-1172
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe proton magnetic resonance spectra of 1-phenethyl-and 1-styryl-1, 2, 3, 4-tetrahydroisoquinoline derivatives were examined and correlations of the chemical shifts with stereochemistry of the molecule were discussed.View full abstractDownload PDF (480K) -
MASAITI YASUE, JINSAKU SAKAKIBARA, NORIHISA KAWAMURA, KATSUYA SAWADA1970 Volume 90 Issue 9 Pages 1172-1174
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSHigher aliphatic hydrocarbons, alcohols, fatty acids, and their methyl esters were isolated from the leaves of Evodiopanax innovans NAKAI. A small amount of stigmasterol was suggested as one of the constituents.View full abstractDownload PDF (446K) -
MASAITI YASUE, JINSAKU SAKAKIBARA, TOYO KAIYA1970 Volume 90 Issue 9 Pages 1174-1177
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDried flowers of Lyonia ovalifolia var. elliptica were successively extracted with benzene, acetone, and methanol. From the benzene extract were isolated hydrocarbons, alcohols, oleanolic acid, maslinic acid, and a new compound, which is now under investigation. From the acetone extract were isolated glucose, fructose, quercetin, hyperoside (quercetin 3-galactoside), an unidentified flavonoid, β-sitosterol, ursolic acid, and maslinic aicd. Sucrose was detected from the methanol extract.View full abstractDownload PDF (505K) -
MASAO TOMITA, YASUKO OKAMOTO, YOSHIKO NAGAI, KEIKO KITAYAMA, HIROKO YA ...1970 Volume 90 Issue 9 Pages 1178-1181
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBase A, base B, and a new base, dauricoline, a tertiary phenolic biscoclaurine -type base, were newly isolated from the rhizome of Menispermum dauricum DC. (Japanese name "Kohmori-kazura"), besides the known dauricine (II) and daurinoline (I). Dauricoline occurs as a pale yellow powder and its methylation with diazomethane gives O-methyldauricine (IV). O, O, O-Triethyldauricoline (V), obtained by ethylation with diazoethane, undergoes cleavage with metallic sodium in liquid ammonia and forms D-(-)-1-(2-ethoxybenzyl)-6-ethoxy-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (VI) as the nonphenolic base and D-(-)-1-(p-hydroxybenzyl)-6-ethoxy-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (VII) as the phenolic base. Based on these results, the structure of dauricoline was found to be expressed by formula III.View full abstractDownload PDF (550K) -
MASAO TOMITA, YASUKO OKAMOTO, YOSHIKO NAGAI, SHIGEKO TANAKA, TOSHIE HA ...1970 Volume 90 Issue 9 Pages 1182-1186
Published: September 25, 1970
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFrom the rhizome of the Russian Menispermum dahuricum DC., the structurally known stepharine (VIII), acutumidine (V), magnoflorine (IX), and a new biscoclaurine-type base, dauricinoline, were newly isolated besides dauricine (I), sinomenine (VII), acutumine (IV), and menisperine (VI) already reported in literature. The new base, dauricinoline, occurs as a pale yellow powder and its methylation with diazomethane gives O-methyl-dauricine (X). The O, O-diethyl compound (XI), obtained by ethylation with diazoethane, undergoes fission by metallic sodium in liquid ammonia and produces D-(-)-1-(p-ethoxybenzyl)-6-ethoxy-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (XII) as the nonphenolic base and D-(-)-armepavine (XIII) as the phenolic base. From these results, the structure of dauricinoline was proved to be expressed by the formula XIV.View full abstractDownload PDF (628K)
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