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Volume 94, Issue 7
Displaying 1-19 of 19 articles from this issue
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SHIGEO BABA, MASANOBU HORIE1974 Volume 94 Issue 7 Pages 779-782
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBasic studies were made on the applicability of a drug labeled with deuterium in the benzene ring for the metabolic study in man. After oral administration of l-ephedrine [arom. U-3H, α-14C] or l-ephedrine[p-3H, α-14C] to a rat or incubation with rabbit liver slices, the metabolites were separated and purified to a constant 3H/14C ratio. The percentage retention of tritium in each metabolite was calculated. Significant isotope effect of tritium was observed at the synthetic step where a propionyl group was introduced by the Friedel-Crafts reaction. Neither noticeable tritium loss nor isotope effect was observed in the formation of metabolites which were produced by the metabolic changes on the side-chain moiety of the substrate. This result supports the expected applicability. A near compete NIH shift of the label was observed during hydroxylation reactions. Percentage retention of tritium (over 90% in each case) was found with p-hydroxyephedrine. 3H/14C ratios of the glucuronide of p-hydroxyephedrine and p-hydroxyephedrine regenerated from the glucuronide were found to possess a significantly 1ower3H/14C ratio.View full abstractDownload PDF (605K) -
SHIGEO BABA, KUNIO KAWAI1974 Volume 94 Issue 7 Pages 783-787
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAs a fundamental study on the applicability of a drug labeled with deuterium on benzene ring for the human metabolic studies, l-ephedrine [arom.-2H5] was synthesized by a reaction sequence starting with benzene [arom.-2H6]. Infrared (IR), nuclear magnetic resonance (NMR), and mass spectra of l-ephedrine [arom.-2H5] and propiophenone [arom.-2H5] were compared with those of the corresponding nonlabeled compounds. The bands at 700 and 750 cm-1, which appear characteristically in monosubstituted benzene derivatives, disappear completely in the IR spectra of deuterated compounds, and absorptions for the aromatic C-H (3000-3100 cm-1) and aromatic C=C (1600 cm-1 shifted completely to 2280 cm-1 and 1560 cm-1 respectively.The signal for aromatic proton in NMR spectrum is completely lacking in the deuterated samples. From these data, it was concluded that l-ephedrine [arom.-2H5] obtained here does not contain a perceptible amount of hydrogen on its benzene ring. Comparison of mass spectra of deuterated compounds with that of nonlabeled compounds, suggests that an intramolecular exchange reaction between deuterium on the benzene ring and hydrogen on the side chain does occur during the fragmentation process to a small but significant extent.View full abstractDownload PDF (678K) -
EIICHI FUJITA, MANABU NODE, YOSHIMITSU NAGAO, TETSURO FUJITA1974 Volume 94 Issue 7 Pages 788-795
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBiogenetic consideration on 30 Isodon diterpenoids, structures of which had been elucidated, led to their systematic classification. Discussion on their biogenesis is presented.View full abstractDownload PDF (744K) -
HIROSHI OTSUKA, MAKOTO TSUKUI, TOSHIRO MATSUOKA, MINORU GOTO, HAJIME F ...1974 Volume 94 Issue 7 Pages 796-801
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe fertile egg method of D'arcy, et al. was found to be suitable for anti-inflammatory screening of extracts of natural sources. The suitable primary incubation period and implantation period were 9 and 4 days, respectively. Certain dose of steroidal anti-inflammatory drugs, e.g., 6.3 μg/disc of dexamethazone, significantly inhibited the granulation tissue formation of chorio-allantoic membrane in the established method. Non-steroidal drugs, such as phenylbutazone, showed inhibitory action at 500 μg/disc. This screening method was applied to aqueous methanolic (1 : 1) extracts from more than a thousand crude drugs and plants and 62 extracts were found to be active at 800 μg/disc. It was found that berberine-containing plants, e.g., coptis rhizome, were strongly active even in a dose of 400 μg/disc.View full abstractDownload PDF (717K) -
TSUTOMU IRIKURA, YOSHIO NAGATSU, SHIGEO BABA, HISAO SONE1974 Volume 94 Issue 7 Pages 802-810
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn order to study the metabolic fate of 1-butyryl-4-cinnamylpiperazine hydrochloride (BCP), a new analgesic drug, 1-butyryl-4-cinnamyl [γ-14C] piperazine hydrochloride (BCP-14C) was administered subcutaneously to the rat at a dose of 20 mg/kg. The highest concentration of 14C-activity in blood was found 20 min after administration of BCP-14C. About 27% and 49% of the administered 14C-activity were excreted in the 24 hr urine and feces, respectively. The distribution of BCP-14C in the rat was detected by the wholebody autoradiogram and the 14C-activity of each tissue was determined by a liquid scintillation counter. Major metabolites in the urine were BCP, 1-butyryl-4-(4'-hydroxy) cinnamylpiperazine (p-OH-BCP), 4-hydroxycinnamylpiperazine (p-OH-CP), benzoic acid, and hippuric acid. On the other hand, p-OH-BCP, p-OH-CP, and their conjugates were the major metabolites in the bile. These results suggested that the major metabolic pathway of BCP in the rat was the para-hydroxylation. The 14C-activity in the liver (66.6%) was identified as BCP, p-OH-BCP, cinnamylpiperazine, p-OH-CP, and cinnamic acid. In the brain, 0.84% of the administered 14C-activity was found at 20 min after the administation and almost all of the 14C-activity (94.5%) originated from unchanged BCP.View full abstractDownload PDF (1339K) -
AKIRA KUDO, HIDEO MATSUKI, TSUNETO KURIYAMA1974 Volume 94 Issue 7 Pages 811-816
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSN-Methyl-N, N-bis(3-methylsulfony1oxypropyl) amine hydrochloride (No.838) and N, N-bis (3-methylsulfonyloxypropyl) amine hydrochloride (No.864) decomposed easily in the absence of water. This decomposition resulted from the exchange reaction between sulfonate residue and chloride ion. Acid moieties of No.838 and No.864 were converted from HCl to various organic acids with the intention of increasing their stability. Among the compounds prepared, the salts of 4, 4'-biphenyldisulfonic acid (838-D) and of p-toluenesulfonic acid (864-T) were stable enough for the formulation of oral tablets, which were able to be stored for a long time.View full abstractDownload PDF (700K) -
AKIRA TENSHO, IWAO SHIMIZU, TADAOMI TAKENAWA, HIROYUKI KIKUCHI, TSUNES ...1974 Volume 94 Issue 7 Pages 817-825
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSStudies were made on the experimental conditions for the rapid dietary induction of aortic lipidosis in rats and results obtained showed that the strain of the animal as well as the type of fat in diet was a very important factor for the early development of the lesion. Gross aortic lipidosis was produced regularly after 4 weeks in Sprague-Dawley rats by feeding a semi-synthetic diet containing 3% cholesterol, 1% cholic acid, 0.3% thiouracil, 21% hydrogenated fat, 30% lactose, and 40% casein. Densitometric determinations of gross aorta stained with Sudan made quantitative assessment of the severity and extent of the lesions possible. In all these experiments no significant correlation exsisted between the degree of vasular lipidosis and the serum of liver lipid levels. Histopathological examinations of the aorta revealed some accumulation of lipid-filled foam cells in the subendothelial space, disintegration of the internal elastic lamella, and lipid deposits in smooth muscle cells in the media. Corticosteroid hormones significantly suppressed the development of short-term aortic lipidosis, while they elevated serum cholesterol levels compared with that of control.View full abstractDownload PDF (1129K) -
SHIGEO BABA, KUNIO KAWAI, YASUO SHIDA1974 Volume 94 Issue 7 Pages 826-832
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSMass spectral problems on the applicability of a drug labeled with deuterium on the benzene ring for the metabolic studies in man were investigated using benzoic acid [arom.-2H5] and hippuric acid [arom.-2H5]. By comparing the mass spectra of deuterated compounds with those of unlabeled analogues, an intramolecular exchange reaction between deuterium on the benzene ring and hydrogen on the side chain was recognized slightly in the phenyl ion and remarkably in the benzoyl ion from the deuterated benzoic acid. However, such an exchange reaction was not observed in any ion from the deuterated hippuric acid. Deuterium radical from the M-CO2+ of labeled hippuric acid was lost during the fragmentation. Moreover, an isotope effect of a few percent was obsirved in the production of the phenyl ion and the C4H3+ ion by examination of the mass spectrum of an equimolar mixture of nonlabeled and labeled compounds. From these results, the molecular ion and the benzoyl ion of benzoic acid, and the benzoyl ion of hippuric acid were chosen as the main peak for quantitative analysis. By comparing the total peak height in the region of the ±1 mass unit of the main peak from deuterated compound with those from protiated counterpart, the former diluted in the order of 100-fold amount of the latter was determined with a precision within 3%.View full abstractDownload PDF (891K) -
YASUHIKO NAKAMURA, AKINOBU OTSUKA, MASAYUKI NAKAGAKI1974 Volume 94 Issue 7 Pages 833-838
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe flocculation-deflocculation behavior of sulfathiazole, α-alumina, and graphite in the solutions of dodecylamine hydrochloride (DAHCl) and of sodium dodecyl sulfate (SDS) was studied by means of sedimentation measurements, All of these powders showed flocculation in a very low concentration of each surfactant, suggesting that surfactant molecules were adsorbed nearly vertically with their ionic groups attached to the solid surfaces and, hence, the surfaces were rendered hydrophobic. With an increase in surfactant concentration, the deflocculating effect appeared to occur. It is likely therefore that in the second layer, the ionic groups were directed toward the solution. This view was supported by wettability measurements. Adsorption and electrokinetic measurements were also carried out in order to check the above concept and to investigate the mechanism of the interaction between solid surfaces and surfactant ions, in detail. The ζ-potential of all the samples in pure water was negative, while that of graphite was very small, and the addition of DAHCl changed the sign of ζ-potential. Sulfathiazole and alumina adsorbed SDS as well as DAHCl in spite of the same sign, although the amount of adsorption was found to be less than that of DAHCl. It would seem then that a small number of positive sites was also present on the surface of these solids. Graphite showed a high adsorption activity and the saturation amount for each surfactant exceeded to a large extent the monolayer capacity calculated from the surface area of the powder and the limiting area per a surfactant molecule at the air-water interface.View full abstractDownload PDF (1133K) -
CHIKATOSHI MASEDA, MASAKATSU SONE, YOSHINORI TOMINAGA, REIKO NATSUKI, ...1974 Volume 94 Issue 7 Pages 839-843
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIndo1izine derivatives (II and V) were synthesized by the reaction of α-bismethyl-thiomethylene-2-pyridineacetonitrile (I) and dimethyl N-(2-pyridyl)-dithiocarbimidate (III) with α-haloketone compound, ethyl γ-bromocrotonate. Reaction of I with nitromethane afforded 1-cyano-2-methylthio-3--nitrosoindolizine (VIII). Dimethyl 1-carbamoyl-2-methyl thiocycl [3, 2, 2] azine-3, 4-dicarboxylate (XI) was obtained from the indolizine derivative (IX) and dimethyl acetylenedicarboxylate.View full abstractDownload PDF (643K) -
CHIAKI TANI, NAOTAKA NAGAKURA, SHIN HATTORI, MUH-TSUEN KAO1974 Volume 94 Issue 7 Pages 844-851
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAlkaloidal and neutral substances of Formosan Corydalis koidzumiana OHWI were examined. Protopine, α-allocryptopine, dl-tetrahydropalmatine, d-corydaline, d-stylopine, l-scoulerine, l-capaurine, l-isocorypalmine, l-cheilanthifoline, d-corybulbine, sanguinarine, oxysanguinarine, dihydrosanguinarine, L-(+)-reticuline, sinoacutine, pallidine, and 10-nonacosanol were isolated from the whole herb of this plant.View full abstractDownload PDF (1035K) -
GOUKI FUKATA, YUICHI KAWAZOE, TANEZO TAGUCHI1974 Volume 94 Issue 7 Pages 852-857
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSHydroquinone was recently found to act as an excellent catalyst in the Gomberg-Bachmann reaction but the action was limited to the reaction of 4-diazo-3, 5-dimethyl-pyrazole with an aromatic hydrocarbon. Therefore, application of this catalyst to the same reaction of common diazonium salts was examined and it was found that hydroquinone was effective in the reaction of p-nitrobenzenediazonium tetrafluoroborate with benzene and nitrobenzene, in the presence of a base which the reaction requires theoretically. It was found that, among the bases used, 3, 5-dimethylpyrazole not only satisfied the theoretical demand of the reaction but also manifested a catalytic action.View full abstractDownload PDF (771K) -
YOSUKE SAWADA, HYOZO TANIYAMA1974 Volume 94 Issue 7 Pages 858-864
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAmino acid derivatives of Racemomycin-A, one of streptothricin group antibiotics, were prepared. Eleven kinds of amino acid were introduced into the amino group in ε-position of the β-lysine moiety of Racemomycin-A by the active esteriftcation method. All the derivatives prepared had an antibacterial activity but less than that of the original antibiotic. Acute toxicity of the derivatives with neutral and acidic amino acid was less than that of the original antibiotic and that of the basic amino derivatives was much lower than that of Racemomycin-C. In all the derivatives, however, prolonged toxicity remained.View full abstractDownload PDF (768K) -
KI-KOCK SUK, AYA NITTA, MASAO KONOSHIMA1974 Volume 94 Issue 7 Pages 865-871
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAlthough Cnidium officinale MAKINO is given as the origin of the crude drug Chuanxion (Senkyu) in Japanese Pharmacopoeiae Ed. VIII, its true origin still remains a doubt. Accordingly histological examination was made on unripe and ripe fruits of several genera related to Chuanxion growing in East Asia, and the present artic1e deals only with Angelica fruit. Characters of this fruit are as follows : vascular bundles are generally located near the bases of each rib, tracheids are arranged right angle to the ribs, and the phloem is on the outer side of xylem in semicirc1e in unripe fruits, fibers and thick-walled cells appear in xylem, so that the phloem is separated to both sides of xylem in mature fruits.View full abstractDownload PDF (1144K) -
NAOKATA MORITA, MINEO SHIMIZU, MUNEHISA ARISAWA, MITSUKO KOSHI, YOSHIH ...1974 Volume 94 Issue 7 Pages 872-874
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSChrysoeriol (I), hyperin (II), and quercitrin (III) were isolited from the leaves of Eurya japonica THUNB. and E. emarginata MAKINO. Chrysoerio1 and betulic acid (IV), were isolated from the bark of E.japonica THUNB.View full abstractDownload PDF (539K) -
NAOKATA MORITA, MINEO SHIMIZU, MUNEHISA ARISAWA, SUSUMU KITANAKA1974 Volume 94 Issue 7 Pages 875-877
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFrom the standpoint of chemotaxonomy, components of the flavonoid in the leaves of Salix plants were examined. The leaves of Salix matsudana KOIDZ.f.tortuosa REHD. afforded chrysoeriol 7-glucuronide as yellow crystals, mp 272-274, and luteolin 7-glucuronide as yellow microneedles, mp 242-244°. Yellow needles, mp 239-240°, were isolated from the leaves of Salix gilgiana SEEMEN and identified as luteolin 7-glucoside by direct comparison.View full abstractDownload PDF (511K) -
EISAKU HAYASHI, SHIN-ICHI SUZUKI1974 Volume 94 Issue 7 Pages 878-881
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSApplication of ketode to 2-quinoxalinecarbonitrile 4-Oxide (I) in benzene, in the presence of sodium amide, results in the substitution of-CN group of I with ketone carbanion and rearrangement of the oxygen in N→O group to the adjacent ring-carbon to form 3-substituted 2(1H)-quinoxalinone derivative. This was found to be true in the case of acetophenone (IIa), propiophenone (IIb), cyclohexanone (IIc), acetone (IId), and diethyl ketone (IIe). For example, the reaction of I with IIa gave 2-(3, 4-dihydro-3-oxo-2-quinoxalinyl) acetophenone (IIIa). In the case of methyl ethyl ketone (IIf), two .kinds of a product was obtained, 1-(3, 4-dihydro-3-oxo-2-quinoxalinyl)-2-butanone (IIIf) and 3-ethyl-2(1H)-quinoxalinone (IV), which was probably formed via 3-(3, 4-dihydro-3-oxo-2-quinoxalinyl)-2-butanone (IIIf'). Reaction of I with methyl propyl ketone (IIg) afforded 1-(IIIg) and 3-(3, 4-dihydro-3-oxo-2-quinoxalinyl)-2-pentanone (IIIg'), but the reaction with methyl isopropyl ketone (IIh) gave on1y one product, 1-(3, 4-dihydro-3-oxo-2-quinolinyl)-3-methyl-2-butanone (IIIh). In both these cases, 2-quinoxalinecarboxamide 4-oxide (V) was formed as a by-product.View full abstractDownload PDF (602K) -
MITSUYO OKAZAKI, YOSHIAKI ISHIZAKI, YOSHIAKI TANAHASHI, HIROSHI HIROTA ...1974 Volume 94 Issue 7 Pages 881-884
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFrom the roots of "San-shion" (Ligularia species), five volatile components (LA-LE) have been isolated. LA, LC, LD, and LE were found to be identical with cyperene, liguloxide, p-cymene, and limonene, respectively. The identity of LB (C15H26O), a tricyclic sesquiterpene ether, with ogarukaya-ether A has recently been shown by Fujita, et al.View full abstractDownload PDF (653K) -
TETSUZO KATO, YUTAKA YAMAMOTO, SHIRO TAKEDA1974 Volume 94 Issue 7 Pages 884-887
Published: July 25, 1974
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe reaction of ketene acetals (Ia-e) with ketene Was studied. Ketene diethylacetal (Ia) reacted with ketene to give 2, 2-diethoxy-4-methyleneoxetane (IIa). Heating of IIa gave acetylketene diethylacetal (Va). Reaction of methylketene diethyladetal (Ib) with ketene afforded 3, 3-diethoxy-2-methylcyclobutan-1-one (IIIb), besides acetylmethylketene diethylacetal (Vb). Phenylketene diethylacetal (Ic) was converted to acetylphenylketene diethylacetal (Vc) by reaction with ketene. Chloroketene diethylacetal (Id) afforded acetylchloroketene diethylacetal (Vd) and chloroacetylketene diethylacetal (VId). On treatment with diluted acid, Va-d and VId were hydrolyzed to give acetoacetate derivatives (VIIa-d, VIIId). VIIa-d reacted with aniline to give imino ether derivatives (IXa-d) in a good yield.View full abstractDownload PDF (564K)
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