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KAZUHIKO KUBOTA, SHIGEHARU KONO, TADAKO KOREEDA
1969Volume 89Issue 4 Pages
441-445
Published: April 25, 1969
Released on J-STAGE: May 30, 2008
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We examined eleven newly synthesized derivatives of basic theophylline as for their pharmaclogical effects on cardiovascular system. Many of these compounds increased the blood flows of renal, femoral and internal carotid arteries of the dog and some of them had stronger effects than theophylline, but one derivative produced a decrease of the renal artery blood flow. Four of these derivatives had inhibitory effects on isolated heart and one of the diamine type was suggested to have histamine releasing action. As a rule, the introduction of polar basic group in theophylline seemed to result in affording smaller effects to cardiovascular system.
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KAZUHIKO KUBOTA, SHIGEHARU KONO, TADAKO KOREEDA
1969Volume 89Issue 4 Pages
446-449
Published: April 25, 1969
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Antihistaminic effects in guinea-pig tracheal smooth muscle and acute toxicity of basic theophylline derivatives were examined. The compounds which have polar substituents generally showed lower toxicities and stronger antihistaminic activities, and several of them gave broader safety margins than theophylline. Histamine releasing action of a derivative containing piperazine group was tested by using mast cells and rat paw edema.
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JUN TOKUSAWA, MUMIO ISHIBASHI
1969Volume 89Issue 4 Pages
450-453
Published: April 25, 1969
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A conventional coulometric titration method for the determination of a small amount of sulfamethoxypyrazine was examined. Sulfamethoxypyrazine was brominated quantitatively with electrolytically generated bromine, in an aqueous hydrochloric acidpotassium bromide medium. The end point was detected by a potentiometer, sulfamethoxypyrazine in a freshly prepared sample solution reacted approximately with four atoms of bromine, while that contained in the solutions allowed to stand for about a month at 20° or heated in 3M hydrochloric acid reacted with six atoms of bromine to produce 3, 5-dibromosulfanylamide. This coulometric titration was simple and rapid, and the results were precise as compared with those obtained by the diazotization volumetric assay.
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MOTOO NAGASAWA, TAKAO MURAKAMI, KEIKO IKEDA, YOICHI HISADA
1969Volume 89Issue 4 Pages
454-459
Published: April 25, 1969
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Essential oils from the buds of Magnolia salicifolia, M. kobus, and M. kobus var, borealis. and of Chinese and domestic crude drug, Xin-yi, the dried buds of Magnolia were analyzed by thin-layer chromatography, infrared absorption spectra, and gas chromatography. 1) The essential oil of M. salicifolia has a more complex composition than that of M. kobus, and contains a large quantity of aromatic compounds such as safrol, methyleugenol, and trans-asaron. The essential oil of M. kobus consists of terpene compounds such as limonene, cineol, and camphor. 2) Chemo-types differing in the main components of essential oil were found in three individuals of M. salicifolia and two of M. kobus. Both indicated distinct geographical distribution.
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TETSUZO KATO, HIROSHI YAMANAKA, JUNSHI KAWAMATA
1969Volume 89Issue 4 Pages
460-463
Published: April 25, 1969
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Reaction of β-aminocrotonamide (I) with monoch1oroacetic anhydride affords β-(monochloroacetamido)crotonamide (IIa), which on heating in tetralin changes into 2-chloromethyl-6-methyl-4(3H)-pyrimidinone(IIIa). Reduction of IIIa gives 2, 6-dimethyl-4(3H)-pyrimidinone (VII). Similarly, 2-dichloromethyl-6-methyl-4(3H)-pyrimidinone (IIIb) and 2-trichloromethyl-6-methyl-4(3H)-pyrimidinone (IIIc) are obtained from β-(dichloroacetamido)crotonamide (IIb) and β-(trichloroacetamido)crotonamide (IIc) by a similar treatment as above. The reaction of cyanoacetyl chloride with β-aminocrotonamide (I) affords β-(cyanoacetamido)crotonamide (IId), which, however, dose not change into 2-cyanomethyl-6-methyl-4(3H)-pyrimidinone (IIId).
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KIYOSHI HARADA, ICHIMONJI SAITO, HIROSHI MIURA, KAZUICHI SUZUKI, ISAMU ...
1969Volume 89Issue 4 Pages
464-468
Published: April 25, 1969
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The effects of thiamine hydrochloride and its decomposed solution on the stabilities of cobalamins under anaerobic conditions were investigated, and the latter one was confirmed to hasten the degradation of cobalamins more strongly than the former one. Among the various decomposed compounds of thiamine hydrochloride, pyrimidine moieties showed no effect, mercaptopropyl alcohol and thiazole moiety showed little effect, but formic acid showed a strong effect on the degradation of hydroxocobalamin. The other organic acids such as acetic, propionic and butyric acid had no effect on the degradation of hydroxocobalamin. In addition, the reaction between formic acid and hydroxocobalamin was observed in detail, and the following results were obtained. (1) Hydroxocobalamin was strongly degradated between pH 5 and pH 7 at low temperatures by formic acid. (2) The brownish yellow degradated solution of hydroxocobalamin had an absorption maximum at 460mμ, but the B
12r, the reduced form of vitamin B
12, was not found in it. (3) Formic acid was also decomposed when it accelerated the decomposition of hydroxocobalamin. From these observations we may suppose that formic acid was decarboxylated by the cobalt of hydroxocobalamin.
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HARUO OGURA, TSUNEO ITOH, MASARU OGIWARA, TAKASHI OKAMOTO
1969Volume 89Issue 4 Pages
469-474
Published: April 25, 1969
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Reaction of 2-mercaptobenzothiazole with α-halogenoaldehyde acetals and α-halogenoketones respectively afforded β-(2-benzothiazolylthio) acetals and -ketones whose treatment with conc. sulfuric acid or polyphosphoric acid effected ring fission to form thiazolo-[2, 3-b]benzothiazolium salts. This method was also used for the synthesis of 2H-[1, 3]-thiazino [2, 3-b] benzothiazolium salts.
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ITSUO MORI
1969Volume 89Issue 4 Pages
475-481
Published: April 25, 1969
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3', 4', 5, ' 6'-Tetrahydroxyfluoran derivatives, substituted with 3, 4, 5, 6-tetrachloro and carboxyl, and their esters were synthesized and their possible use as organic reagents was examined. These derivatives, unlike the non-substituted compounds, did not show any fluorescence and had greater solubility in organic solvents. Added to these advantages, they showed sensitive coloraton with Bi
3+, Sb
3+, Th
4+, Sn
4+, and Pb
2+ions. Of these derivatives, the methyl ester of 3, 4, 5, 6-tetrachloro-3', 4', 5', 6'-tetrahydroxyfluoran was especially suited for chelate titration of bismuth, and the coloration tone was much more bright than that using 3', 4', 5', 6'-tetrahydroxyfluoran. This compound can also be used for absorption spectral determination of bismuth and antimony, it being possible to determine bismuth at 620mμ in a range of 0-10 μg/ml, and antimony at 590mμ in a range of 0.4-3.0μg/ml.
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HIROSHI UEKI, YUKIHO KUBOTA, YOSOJI ITO
1969Volume 89Issue 4 Pages
482-491
Published: April 25, 1969
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A high-molecular parotin -active substance, E-3, was isolated by zone electrophoresis, using Pevikon as the supporting agent, from the fraction possessing a parotin-like activity obtained from the Pronase digest of saliva-parotin-A. This E -3 contained 31.33% of amino acid residue, rich in the content of proline and glutamic acid. The N-terminal amino acid was not detected by the DNP method, while C-terminal was proved to be serine by hydrazine decomposition. E-3 contains sugars consisting of 30.16% of hexose residue and 11.25% of hexosamine residue, and does not contain uronic and sialic acids. E-3 also contains 26.80% of lipid which was assumed to be a glycolipid from its qualitative estimation. Isoelectric point measured by electrophoresis on cellulose acetate was at pH.4.4, and the molecular weight of E-3 measured by the Archibald method was 55000, agreeing with the value calculated from the content of amino acid residue.
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HIROSHI UEKI
1969Volume 89Issue 4 Pages
492-495
Published: April 25, 1969
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The high-molecular parotin-active substance, E-3, purified from saliva-parotin-A, was tested for correlation with its dose and hypocalcemic and leucocytosis-promoting activities in a rabbit. Although a stric linear relationship was not found, the minimum effective dose for these activities was 1.0μg/kg. The minimum effective dose of E-3 for citrate-lowering activity in rabbit serum of 5μg/kg and there was a linear relation between this activity and logarithm of the dose. Since the time required for these biological activities to appear varied markedly with each and since there was a difference in their minimum effective dose, it was assumed that there is no linear relationship among these activities.
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SEISHI TSUCHIYA, YASUO SUZUKI, SEIICHI OKUI
1969Volume 89Issue 4 Pages
496-500
Published: April 25, 1969
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There are histochemical evidences that some of esterases including cholinesterases are localized at the basement of taste buds of vallate papilla of rat tongue and foliate papilla of rabbit tongue. The present article reports the separation of esterases in taste papilla by polyacrylamide-gel thin-layer electrophoresis using α-naphthyl acetate as substrate and fast blue BB salt as coupler. For extraction of tissue esterases, presence of 0.5% Triton-X-100 seems to be desirable and its presence had no effect on the electrophoretic mobility. This fact suggests that some enzymes are firmly bound to the membrane and solubilized by surface active agents. It has been possible to separate ten active bands from rat vallate papilla and eleven active bands from rabbit foliate papilla by the technique described. Of these esterases, two active bands which have lower electrophoretic mobility and detected only after Triton-X-100 treatment were found to exhibit cholinesterase activity.
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SEISHI TSUCHIYA, YASUO SUZUKI, SEIICHI OKUI
1969Volume 89Issue 4 Pages
501-505
Published: April 25, 1969
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In a previous paper, a complex zymogram pattern of the esterases of the vallate papilla of rat tongue and foliate papilla of rabbit tongue was observed in homogenates containing Triton-X-100. The present work was carried out in order to classify these esterases according to their distinctive features in regard to the substrate specificity and its susceptibility to inhibitors. The ten esterases found in rat vallate papilla were classified into two cholinesterases, four arylesterases, three aliesterases, and one unidentified esterase. The unidentified esterase, which migrates towards the anodic side past the gel center, was characteristic of the rat vallate papilla, it was sensitive to eserine in high concentration, and insensitive to organophosphorus insecticides. These characters of the enzyme agree with the characteristics of the "eserine-sensitive noncholinesterase" which has been found in the nerve endings. Two cholinesterases, four arylesterases, and five aliesterases were separated from rabbit foliate papilla. The fact that the taste papilla was rich in cholinesterases and contained multiple forms of esterases suggests that these enzymes might have a certain role in the mechanisms of inducing the taste sensation.
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KATSUHIDE MATOBA, KATSUMI YOSHII, MITSUKO YOSHIOKA, TAKAO YAMAZAKI, YO ...
1969Volume 89Issue 4 Pages
506-509
Published: April 25, 1969
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Acutumine acetate (I) is reduced to II with an excess of lithium aluminium hydride in ether followed by decomposition of aluminium complex with ammonium chloride and water. It is well known that vinylogous esters of six membered rings are reduced to α, β-unsaturated ketones with lithium aluminium hydride. Our experimentals showed that a vinylogous ester (XIII) of five membered rings is reduced to an allyl alcohol (XIV) in quantitative yield under the conditions described in the reduction of I.
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TEISUKE OKANO, HITOSHI MATSUMOTO
1969Volume 89Issue 4 Pages
510-516
Published: April 25, 1969
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The fluorescence spectra of isoquinoline derivatives were measured in a variety of solvents and were examined from the view-point of solvent and external heavy atom effects. Isoquinoline (I), 1-isoquinolinecarbonitrile (II), 1-chloroisoquinoline (III), and 1-diacetylaminoisoquinoline (IV) gave greater fluorescence intensities in hydroxylic solvents than in non-hydroxylic solvents, whereas no alterations due to solvents were found in the fluorescence intensities of 1-aminoisoquinoline (V), 1-dimethylaminoisoquinoline (VI), 1-methoxyisoquinoline (VII), 3-aminoisoquino1ine (VIII), and isocarbostyril (XI). El-Sayed's theory was employed to elucidate the mechanism of these solvent effects, and it was presumed that the increase in fluorescence intensity exhibited by the former group cornpounds in hydroxylic solvents may be attributed to the reversal of
1(π-π
*) and and
3(n-π
*) levels caused by hydrogen bonding between the solute and sovent. The fluorescence of ethanolic solutions of V, 1-amino-3-chloroisoquino1ine (IX), 3-amino-1-chloroisoquinoline (X), 3-aminoisocarbostyril (XII), and 3-amino-2-methylisocarbostyril(XIII) was quenched by the addition of carbon tetrachloride as well as of carbon tetrabromide ; it was presumed that spin-orbit coupling takes place between the excited singlet state and excited triplet state in the presence of external heavy atoms.
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TADAO IDA, SHOJI TAKAHASHI, ISAMU UTSUMI
1969Volume 89Issue 4 Pages
517-523
Published: April 25, 1969
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Several polymeric food dyes were synthesized and examined for their stabilities to light, oxidation, reduction and acute toxicity. Amino or hydroxyl group of food dyes were methacrylated and then polymerized by the use of IBN as catalyst. The polymeric food dyes thus obtained were more stable as for their physical and chemical properties compared with the corresponding food dyes. Especially acute toxicity was improved by polymerization.
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TADAO IDA, TOSHIO WATANABE, SHOJI TAKAHASHI, ISAMU UTSUMI
1969Volume 89Issue 4 Pages
524-530
Published: April 25, 1969
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Various polymeric azodyes were synthesized accoriding to the following method : m-aminostyrene, o-, m- and p-aminomethacryl anilides and m- and p-aminophenolmeth-acrylates were diazotized and then coupled with β-naphthol and H-acid. Theazodyes thus obtained were polymerized with IBN. They were examined as for their stabilities to light, heat, oxidation and reduction, dying property and acute toxicity. According to the results, we have found that polymeric azodyes were more suitable for food dyes than the monomeric ones.
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TOZABURO KURIHARA, HIDEO TAKEDA, HIDEO ITO, KEIKO SAGAWA
1969Volume 89Issue 4 Pages
531-537
Published: April 25, 1969
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For the purpose of studying the relation of the antibiotic activity of cyclic peptide Colistin, and its partial peptides, and in order to prepare pharmacological active short peptides, fifteen dipeptides and five tripeptides containing L-α, γ-diaminobutyric acid (a component of colistin) and analogous L-lysine with -N
α or N
ω-acylated with 6-methyl-octanoic acid or with analogous saturated or unsaturated acid, were synthesized. The peptide condensation was carried out by DCCD or azide method. On the other hand, acylation of amino group was made by the acid chloride method or with acid and DCCD method.
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KIYOKAZU TAKAISHI, YOSHIKO TORII
1969Volume 89Issue 4 Pages
538-543
Published: April 25, 1969
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Chinese medicine makes great use of decoction, i.e. using the crude drugs in the form of an aqueous solution. However, there are many effective principles in these crude drugs that are insoluble in water. These water-insoluble or sparingly soluble components are considered to form a conjugate with water-soluble carbohydrates of high molecular weight (starch, pectin, mucin) which are usual components in crude drugs and thereby increasing their water solubility. Gelatinized starch in solution combines with phenol and bases to form a complex and the solubility of phenol and salts is increased. These complexes interfere with starch-iodine coloration reaction and hydrolysis of starch by amylase. In Gegen Tang the acqueous decoction of arrow root, the gelatized arrow root starch combines with ephedrine of Ma-huang (ephedra herb) in aqueous solution and the solubility of ephedridrine is increased, indicating a characteristic of decoction of crude drugs.
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KEITO BOKI, SABURO ENOMOTO
1969Volume 89Issue 4 Pages
544-548
Published: April 25, 1969
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Methods for the manufacture of cyanoaceticacid methyl ester via cyano-substitution of the chloroaceticacid methyl ester have been hitherto studied by many investigators, but good results have not yet been obtained. The authors have first made clear that the difficulties can be attributed to the impurities existing among the starting material and the product, and then have found a method which gives a good yield by removing these impurities before fractionating the product solution : the foreign compounds are eliminated by a column separation, of which carriers are basic and neutral alumina made in Woelm company. On the other hand, inspecting the structure and the physical properties of these aluminas, it was accounted for that their peculiarities depend not so much on their porous character as their solid base strength.
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KIYOSHI HATA, KIYONORI SANO
1969Volume 89Issue 4 Pages
549-557
Published: April 25, 1969
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The ether extract of the root of Angelica decursiva FR. et SAV. (Umbelliferae) gave two new crystalline coumarins, decursin (I), C
19H
20O
5, mp 110-111°, [a]
15D+172.9°and decursidin (II), C
24H
26O
7, mp 60-62°, [a]
23D-44.8°, and a new non-crystalline coumarin (III), C
24H
28O
7, [a]
D 0°, in addition to known coumarins, nodakenetin and umbelliferone. The structures of I and II were established as 3'-senecioyloxy-3', 4'-dihydroxanthyletin and 3', 4'-disenecioyloxy-3', 4'-dihydroxanthyletin, respectively. The coumarin III was shown to be the angeloylisovaleroyl diester of 3', 4'-dihydroxy-3', 4'-dihydroxanthyletin. The stereochemistry of these coumarins and the location of the acyl groups in III are under investigation.
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JUTARO OKADA, YOSHIAKI KAWASHIMA
1969Volume 89Issue 4 Pages
558-564
Published: April 25, 1969
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In this paper, the extraction of berberine from Phellodendri Cortex was studied. The barks were cut to various sizes (1-1), treated with ether prior to extraction, or untreated, and then, were extracted in water or in methanol. As the result of analysis of extraction rate, the mechanism of extraction consists of washing, diffusional and capillary extraction in both cases of water and methanol, and in the latter case, the capillary extraction has a rather little effect on total extraction. The treatment with ether has little effect on extraction, the choice of solvents is the main factor.
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TAKEHISA CHIBA
1969Volume 89Issue 4 Pages
565-571
Published: April 25, 1969
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SH and S-S compounds were administered to rabbits and variation in the plasma insulin level was assayed by the diaphragm method and by radio-immunological measurements. Plasma insulin was separated into free and bound insulins according to the method of Antoniades and others, and it was found that bound insulin can also be measured by the radio-immunological method. Loading of normal rabbit with glucose results in the increase of free insulin and lowering of bound insulin, accompanying the increase of blood sugar. Administration of adrenalin decreases both free and bound insulin. These facts indicate that variation in the plasma insulin level differs according to the rise in blood sugar from anti-insulin agent and more loading with sugar. Administration of an SH compound to normal rabbit results in the increase of free insulin about 120 minutes later, with slight fall in bound insulin. However, administration of SH compound to alloxan-diabetes rabbit resulted in a two fold increase of free insulin as assayed by the radio-immunological measurement. A corresponding decrease was seen in bound insulin. The first increase of free insulin appeared shortly after the administration (10-20 min) and this peak was not found in normal rabbits. The second increase, occurring 60-120 minutes later, was found also in normal animals. Some SH and S-S compounds are considered to play a part in the control of the Kinetic equilibrium of free and found plasma insulin.
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TAKEHISA CHIBA
1969Volume 89Issue 4 Pages
572-578
Published: April 25, 1969
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Effect of SH and S-S compounds on the liberation of insulin from rat pancreas was examined. (1) Addition of SH or S-S compounds does not affect liberation when glucose was given in an amount of 2 mg/ml of the reaction medium, but with 4 mg/ml of glucose, SH compounds accelerate the liberation and S-S compounds do not. The same tendency is observed in the liberation of insulin from the pancreas of a rat preliminarily given SH or S-S compounds. (2) p-Chloromercuribenzoate (PCMB) interferes with liberation and this interference does not disappear even by addition of SH compounds after pretreatment with PCMB. (3) Addition of insulin to the reaction solution inhibits the liberation. This fact suggests that liberation of insulin from the pancreas is regulated not only by glucose but also by insulin.
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YOSHIRO MASADA, KEIJI HASHIMOTO, TAKEHISA INOUE, HIDEO YOSHIDA, IWAO F ...
1969Volume 89Issue 4 Pages
579-582
Published: April 25, 1969
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Direct coupling of mass spectrometer and gas chromatograph (GC-MS) has been applied to the analysis of fatty acid composition in adrenal lipid of rabbits (normal and diabetes). Isomers of linolenoic and arachidonoic acids were identified. These isomers were found to be 6, 9, 12-octadecatrienoic acid and 8, 11, 14, 17-eicosatetraenoic acid by GC-MS. Heptadecanoic and heptadecenoic acids were also identified by GC-MS.
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TETSUJI KAMETANI, KAZUYA YAMAKI, KUNIO OGASAWARA
1969Volume 89Issue 4 Pages
583-585
Published: April 25, 1969
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Claisen condensation of acetophenone with γ-butyrolactone in the presence of sodium ethoxide afforded 1-hydroxy-6-phenylhexane-4, 6-dione (III), which was treated with 80% hydrazine hydrate to give 3-phenyl-5-(3-hydroxypropyl)pyrazole (IV). Cyclization of IV with phosphoryl chloride or 48% hydrobromic acid gave 3-phenyl-1, 5-trimethylenepyrazole (II), one of the isomers of withasomnine.
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TETSUJI KAMETANI, TSUNEKAZU TERUI, KEIICHIRO FUKUMOTO
1969Volume 89Issue 4 Pages
586-588
Published: April 25, 1969
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1-(m-Chlorophenylpropyl) -6, 7-dimethoxy -1, 2, 3, 4-tetrahydro-isoquinoline (III) was synthesized in order to examine whether this compound would be effective as a muscle relaxant or not. 3-Chlorobutyric acid (IX), which was obtained from m-chlorophenyl-propionic acid (IV) via 3-chlorophenylpropanol (VI), the corresponding chloride (VII) and cyanide (VIII), was converted into the amide (XI) and the Bischler-Napieralski reaction of XI, followed by reduction of its product, gave 1, 2, 3, 4-tetrahydroisoquinoline (III). Further, the reaction of 1, 2, 3, 4-tetrahydroisoquinoline (III) with sodium amide in liquid ammonia was also investigated.
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TOSHIAKI TOMIMATSU
1969Volume 89Issue 4 Pages
589-590
Published: April 25, 1969
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Bupleurum longiradiatum TURCZ. is often used as a substitute for the crude drug 'Saiko, ' the radix of Bupleurum falcatum L., or mixed in it. No detailed studies have been made on the components of B. longiradiatum and, therefore, examinations were made on the components in its root. Sucrose and α-spinasterol were obtained in 1.28% and 0.00064% yield (against the dried root), isolated as crystals, and identified. Sucrose was not detected in the root of B. falcatum when subjected to the same treatment as that of B. longiradiatum.
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TAKEO TAKAHASHI
1969Volume 89Issue 4 Pages
591-594
Published: April 25, 1969
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9-Substituted adenines (VI) were synthesized with high yield from 4-amimo-5-nitro-6-substituted pyrimidines (III) under conditions that reduction of nitro group and cyclization was performed on a single process using hydrosulfite as the reducing agent. The overall yield from 4, 6-dichloro-5 -nitropyrimidine (I) was about 25-51%. 9-Ethyl-1-methyladenine and 9-benzyl-1-methyladenine were synthesized in addition.
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YUZO NAGASE, USHIHO MATSUMOTO, KENJI SHIMADA
1969Volume 89Issue 4 Pages
595-597
Published: April 25, 1969
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The presence of a polymorphism phenomenon in a crystalline d-biotin was observed by infrared spectroscopy (IR) and X-ray diffractometry. By these measurements, d-biotin rectystallized from water (α type) and 80% ethanol (β type) revealed different IR spectra and diffraction powder patterns. These two kinds of crystals were different as for their crystalline form, and slightly as for their melting point. Elementary analysis showed the absence of water or solvent of crystallization in each type, respectively. It was found that d-biotin obtained by dissolution in methanol and evaporation of the solvent was a mixture of α and β type. The thermal conversion to a type isomorph was shown by heating the β type d-biotin at 200°, 1 hr.
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