YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Volume 103, Issue 6
Displaying 1-16 of 16 articles from this issue
  • EMIKO TOMITORI, TOSHIHIKO OKAMOTO, TATSUO IDO
    1983 Volume 103 Issue 6 Pages 601-606
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    Reaction of 6-nitroquinoline (1) with potassium cyanide in methanol was analyzed. The major products were 5-cyano-6-methoxyquinoline (2) and 1-aminoisoxazolo[4, 3-f]-quinoline (3). An acidic product, 4-oxo-3, 4-dihydro-1, 2, 3-triazino[4, 5-f]quinoline (8) was isolated. The structure of 8 was confirmed by synthesis from 6-aminoquinoline-5-carboxamide. Compound 8 was confirmed by synthesis from 6-aminoquinoline-5-carboxamide. Compound 8 could be prepared from 3 and hydroxylamine in alkaline solution : this suggested that NO- was eliminated from the primary intermediate, 5-cyano-6-nitrosoquinoline, by nucleophilic attack of methoxide anion perticipates. This also explains the formation of the major product, 2. The formation of the isoxazole derivative (3) is interpreted by the nucleophilic perticipation of cyanide anion. The mechanism proposed satisfies the observation obtained by isotope experiments.
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  • TSUYOSHI TOMIMORI, YUKINORI MIYAICHI, YOSHITAKA IMOTO, HARUHISA KIZU, ...
    1983 Volume 103 Issue 6 Pages 607-611
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    From the root of Scutellaria baicalensis GEORGI, two new flavonoids, III and IV, were isolated, together with 5-hydroxy-7, 8-dimethoxyflavone (I), norwogonin (II) and dihydrobaicalin (V). The structures of III and IV were established as 5, 7, 2'-trihydroxy-6-methoxyflavone and 5, 2'-dihydroxy-6, 7, 8-trimethoxyflavone, respectively.
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  • ISAO KITAGAWA, MASAYUKI YOSHIKAWA, MINORU YOSHIHARA, TERUAKI HAYASHI, ...
    1983 Volume 103 Issue 6 Pages 612-622
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    During the studies on the chemical characterization of crude drug precession, the constituents of Ginseng Radix Rubra were investigated by comparing with those of Ginseng Radix. Panaxynol (4), ginsenosides Ro, Rb1, Rb2, Rc, Rd, Re, Rf, Rg1, Rg2 (11), Rg3 (10a), and Rh1 (9) were identified as common constituents of both Ginseng, whereas panaxytriol (1), ginsenoside Rh2 (8), 20 (R)-ginsenoside Rh1 (9a), 20 (S)-ginsenoside Rg3 (10), and 20 (R)-ginsenoside Rg2 (11a) were elucidated as characteristic constituents of Ginseng Radix Rubra. It was also found that Ginseng Radix Rubra contained larger quantities of ginsenosides Rh1 (9), Rg3 (10a), and Rg2 (11) than Ginseng Radix. The less polar constituents of Ginseng Radix Rubra were shown to significantly differ from those of various samples of Ginseng Radix by means of the thin layer chromatographyprofile analysis.
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  • ETSUO OISHI, HIROMI WATANABE, EISAKU HAYASHI
    1983 Volume 103 Issue 6 Pages 623-630
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    5, 8-Dichloropyrido[2, 3-d]pyridazine (I), in benzene in the presence of sodium amide, reacted with active methylene compounds ; ethyl cyanoacetate (IIa), ethyl acetoacetate (IIb), diethyl malonate (IIc), malononitrile (IId), phenylacetonitrile (IIe), to afford 5-substituted (R1)-8-chloropyrido[2, 3-d]pyridazine (III) or 8-substituted (R2)-5-chloropyrido[2, 3-d]pyridazine (IV) ; IIIa (R1=NC-C^^^〓H-CO2C2H5), IVa (R2=NC-C^^^〓H-CO2C2H5), IVb' (R2=-CH2CO2C2H5), IVc (R2=-CH(CO2C2H5)2), IIId (R1=-CH(CN)2), IVe (R2=NC-C^^^〓H-Ph). Compound I, in toluene in the presence of sodium hydride, also reacted with acetophenone (IIf), propiophenone (IIg) to afford 2-(5-chloro-8-pyrido[2, 3-d]pyridazinyl) acetophenone (VII), 2, 2'-(5, 8-pyrido[2, 3-d]pyridazinediyl) di-(1-phenylethanone) (VIII) ; 2-(5-chloro-8-pyrido[2, 3-d]pyridazinyl) propiophenone (XV) respectively. However, reaction of I with acetone (IIh), diethyl ketone (IIi) gave no 5 or 8-substituted pyrido[2, 3-d]-pyridazine der., but a mixture of structure-unknown products.
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  • ETSUO OISHI, KATSUMI NAKAMURA, EISAKU HAYASHI
    1983 Volume 103 Issue 6 Pages 631-643
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    Chemical properties of 5-phenylpyrido[2, 3-d]pyridazine 7-oxide (II), obtained in the reaction of 5-phenylpyrido[2, 3-d]pyridazine (I) with m-chloroperbenzoic acid, were studied. Compound II reacted with nucleophiles to give 5-phenyl-8-substituted (R1)-pyrido[2, 3-d]pyridazine or 5-phenyl-8-substituted (R2)-pyrido[2, 3-d]pyridazine 7-oxide. Nucleophiles[Products] ; phosphoryl chloride, sulfuryl chloride, tosyl chloride and potassium carbonate [XVIII (R1=-C1)], benzoyl chloride and potassium cyanide [III (R1=-CN)], sodium hydroxide [XVII (R1=-OH) and I], methylmagnesium iodide, ethyl-(isopropyl) magnesium bromide [IVa, b, c (R2=-CH3, -C2H5, -CH(CH3)2], acetophenone [IVa, in the presence of NaOH ; IVa and VI (R1=-CH2COPh), in the presence of CH3ONa], ethyl cyanoacetate [IX (R1=NC-C^^^〓H-CO2C2H5), in Ac2O ; X (R1=NC-C^^^〓H-CO2CH3) and XI (R1=-OCH3), in the presence of CH3ONa]. Application of Reissert-Henze reaction to IVb gave α-methyl-5-phenyl-8-pyrido[2, 3-d]pyridazinylmethyl benzoate (VII). Reaction of II and dimethyl acethylenedicarboxylate afforded three products (XIIa, b, c), which showed the same molecular formula (C19H15NO5). The structures of XIIa and XIIb were presumed to be methyl 6-methoxycarbonyl-α-oxo-5-phenyl-6H-cyclopenta[b]pyridine-6-ethanoate (XIIa), methyl 5-phenylpyrido[3, 2-c]oxepine-7, 8-dicarboxylate (XIIb), respectively. It is considered that these products are formed by the liberation of nitrogen from 1, 3-dipolar cycloadducts. In these reactions, the poor yield of the expected product was accompanied in majority of cases with viscous substance with unknown structure.
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  • TAKAYUKI ITO, HIROSHI OGAWA, MINORU MAEDA, MASAHARU KOJIMA
    1983 Volume 103 Issue 6 Pages 644-649
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    Attempts to improve adrenal imaging with 131I-6β-iodomethyl-19-norcholest-5 (10)-en-3β-ol (NCL-6-131I) were made. Various NCL-6-131Is with higher specific activity than those used clinically were prepared. An increase in specific activity of NCL-6-131I had no significant effect on the rat adrenal uptake, but caused an increase in the liver concentration of radioactivity. Lipid extraction and radiochromatographic analysis showed the presence of unchanged NCL-6-131I in the liver, but in the adrenal the esterified form of NCL-6-131I was predominant. Autoradiochromatogram of faeces extract indicated the presence of a radioactive spot with an Rf value slightly lower than that of NCL-6-131I. Effects of N-(4-hydroxyphenyl) salicylamide and ursodeoxycholic acid on rat biodistribution of NCL-6-131I were also examined. No significant effect on the adrenal uptake and adrenal-liver ratio of NCL-6-131I was observed in either case.
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  • TOSHIYUKI SANO, MASATOSHI SYOYAMA
    1983 Volume 103 Issue 6 Pages 650-654
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    Cartap could be determined colorimetrically and fluorometrically by use of ion pair extraction with calcon, which was used for fluorometric reagent of aluminium ion. Cartap (S, S'-[2-(dimethylamino) trimethylene]-bis (thiocarbamate)) was hydrolyzed to nereistoxin, and then 0.5 ml of 0.2% calcon and 4 ml of dichloromethane was added to 1 ml of the nereistoxin solution in acidic medium. The mixture was shaked mechanically for 1 min, followed by separation and centrifugation of the extracted solution. The solution showed max. absorbance at 530 nm, and that obeyed Beer's law in the range of 1 to 20μg/ml. Then, the solution was made to be fluorescence one by the addition of aluminium ion in acidic medium. Samples including lower content of cartap could be determined by the measurement of fluorescence intensity.
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  • YUKIHO KUBOTA, SHOZO SHOJI, TAKAYUKI FUNAKOSHI, KAZUHIRO SHIONAGA, HIR ...
    1983 Volume 103 Issue 6 Pages 655-661
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    An esterase was separated from the exocarp of Citrus natsudaidai HAYATA in a highly purified from. The enzyme hydrolyzes p-nitrophenyl esters of fatty acids, phenyl acetate, and tosylarginine methyl ester at varing rates. Of the substrates tested, p-nitrophenyl acetate, for which the specific activity was determined to be 18.60 units per mg of protein, was most rapidly hydrolyzed. The esterase was free from carboxypeptidase and other proteolytic activities. The esterase had a pH optimum at pH 5.5 for p-nitrophenyl acetate. It was strongly inhibited by HgCl2. The other metal ions or inorganic anions tested showed no significant effect on the enzymatic activity. The values of s20, w and D20, w were 1.8 S and 4.5×10-7cm2/s, respectively, and the molecular weight was calculated to be 40000 from these values. The enzyme was composed of 323 amino acid residues : Trp2, Lys21, His9, Arg10, Hyp23, Asp24, Thr18, Ser35, Glu22, Pro20, Gly40, Ala22, Cys(half)2, Val18, Met3, Ile12, Leu17, Tyr14, Phe11.
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  • SHIGERU AONUMA, YASUHIRO KOHAMA, TOSHITAKE MAKINO, KUNIHIRO HATTORI
    1983 Volume 103 Issue 6 Pages 662-666
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    The effect of an atrial peptide, Gly-Pro-4Hyp-Gly-Ala-Gly (AAP), on several druginduced arrhythmias in anesthetized dogs, rats and mice was investigated together with its effect on the related functions. AAP (10 mg/kg, i.v.) significantly reversed the persistent arrhythmias consisting of atrio-ventricular (A-V) block, ectopic beat and/or ventricular tachycardia induced by aconitine pretreatment, to normal sinus rhythm for a while, and evidently prevented development of ventricular fibrillation in dogs and rats. AAP (10, 25 mg/kg, i.v.) significantly prolonged the time until onset of A-V block or ectopic beat and the time until onset of ventricular tachycardia induced by aconitine infusion in mice. This peptide (10 mg/kg, i.v.) significantly prolonged the onset time of A-V block or ectopic beat induced by CaCl2 infusion and the time until ventricular fibrillation induced by ouabain infusion in mice, and significantly shortened the duration of arrhythmia induced by ADP in rats, but did not affect the mouse epinephrine-induced arrhythmia. The peptide (25 mg/kg, i.v.) was found to prolong significantly the QTc interval and to have no effect on the PQ interval, heart rate, respiratory rate and blood pressure in dogs. AAP (1 g/kg. i.v., i.p. and p.o.) did not show the acute toxicity in mice. AAP was a chemically new type of antiarrhythmic substance with very little side effect and low toxicity, possessing the action intensity almost equal to quinidine.
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  • HIDEO NAKAMURA, SATORU MOTOYOSHI, YASUHIRO SETO, CHIEKO IMAZU, TOSHIAK ...
    1983 Volume 103 Issue 6 Pages 667-674
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    Therapeutic effect of etofenamate gel (5% etofenamate), applied topically, on traumatic edema and mode of its anti-edema action were investigated in rats. Plasma flufenamic acid levels were 5.73 and 0.173μg/ml 2.5 h after oral administration of etofenamate (diethylene glycol ester of flufenamic acid, 8.5 mg/kg) and after topical application of etofenamate gel (33 mg/paw) equipotent to the oral etofenamate, respectively. Etofenamate gel (25 mg/paw) showed a significant therapeutic effect against traumatic edema of the hind paw, when the gel was applied to the inflamed paw 2 h after bruising but not to the non-inflamed paw. Vehicle gel lacked the activity. Etofenamate gel (25 mg/paw) inhibited both the early and delayed phases of hind paw edema produced by the mixed phlogistics (histamine, serotonin, kaolin, carrageenin), but vehicle gel inhibited only the early phase mediated by histamine and serotonin. Hind paw edema induced by carrageenin (1 mg) was potentiated by the concomitant administration of arachidonic acid (100μg) or PGE2 (1μg). Etofenamate gel (25 mg/paw) did not modify the edema produced by the combination of carrageenin and PGE2, but reduced the arachidonic acid potentiation of carrageenin-induced edema. Vehicle gel did not reduce the edema. From these results, it was suggested that etofenamate gel, applied topically, produced locally therapeutic activity against traumatic edema, and mode of its antiedema action was discussed.
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  • MITSURU NAKAYAMA, TOKUNARU HORIE, CHUNNAN LIN, MUNEHISA ARISAWA, MINEO ...
    1983 Volume 103 Issue 6 Pages 675-678
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    5, 7-Dihydroxy-4', 8-dimethoxyflavone (1) was synthesized for the structural confirmation of cirsitakaogenin. However, it was not identical with the natural pigment but it was found that cirsitakaogenin and cirsitakaoside should be read as cirsimaritin (3) and cirsimarin (4), respectively.
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  • TADAYUKI KURAISHI, YOJI MITADERA, TAKAO MURAKAMI, NOBUTOSHI TANAKA, YA ...
    1983 Volume 103 Issue 6 Pages 679-682
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    From the fronds of Dicranopteris dichotoma (THUMB.) BERNH. protocathechuic acid, shikimic acid and two unknown glycosides, which were shown to be p-β-rutinosyloxystyrene (I) and 1-(1-hydroxyethyl)-4-β-rutinosyloxybenzene (II) mainly by spectroscopic methods, were isolated besides the already detected flavonoids (afzelin and quercitrin). The yield of shikimic acid referred to the dry fronds amounted to 3%. From the fronds of Microlepia obtusiloba HAYATA an unknown glycoside was isolated and identified as p-β-D-allosyloxystyrene (III) by spectroscopic methods.
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  • TAKUO KOSUGE, HARUO NUKAYA, TOSUKE YAMAMOTO, KUNIRO TSUJI
    1983 Volume 103 Issue 6 Pages 683-685
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    Two cardiac principles were isolated from nekombu (the basal part of the blade of a laminariaceous seaweed). Fatty acids of C14, C16 and C18 were found to stimulate the isolated frog heart, while histamine dihydroiodate to accelerate the isolated guinea pig atrium. Histamine and iodine contents of nekombu were 501 mg/kg and 3200 mg/kg, respectively, indicating that 36% of the total iodine present in nekombu is in the salt form of histamine. It was also found that a small amount of histamine improves the taste of glutamic acid.
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  • TADAMASA TERAI, MASAAKI KATAI, HARUO MEGURI
    1983 Volume 103 Issue 6 Pages 686-689
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
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    A spectrophotometric method has been established for the determination of grayanotoxin (G)-I, G-II and G-III, toxic diterpenoids of Leucothoe grayana MAXIM., by using a color reaction with vanillin in perchloric acid. This method has been applied to the determination of these grayanoid compounds contained in toxic honey.
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  • YOSHIYUKI HIRAKAWA, KIYOSHI HARADA
    1983 Volume 103 Issue 6 Pages 690-695
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    In the previous paper, a new technique for particle size reduction of oxolinic acid (OA), a slightly soluble model drug having an acidic group in a molecule, by the crystallization through the neutralization of its alkaline solution in the presence of certain surfactant or polymer was described. The wet sieving method by the use of polycarbonate membrane filter for the evaluation of size reduction effect was also described. Various factors affecting the size reduction of OA were investigated in this paper. The results obtained were as follows ; manners of participation in various factors affecting the size reduction varied with OA concentration at crystallization, and in the case of 5 w/v% OA concentration, the influences of addition rate of hydrochloric acid solution, stirring rate, reaction temperature and concentration of hydrochloric acid were relatively low. Size reduction effects of various surfactants and polymers were investigated. All of them were effective, though differences were recognized in the extent of size reduction. It has been found that the establishment of optimal conditions to obtain the finest particles is enabled and moreover, there is a possibility to prepare the particle that have an optional particle size by regulating the various factors.
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  • AINA LAO, YASUO FUJIMOTO, TAKASHI TATSUNO
    1983 Volume 103 Issue 6 Pages 696-699
    Published: June 25, 1983
    Released on J-STAGE: May 30, 2008
    JOURNAL FREE ACCESS
    From Artemisia rubripes NAKAI (Compositae) collected in China were isolated ten compounds, eupatilin, 4'-demethyleupatilin, cirsilineol, dammaradienyl acetate, bauerenyl acetate, cycloartenyl acetate, cycloart-23-en-3β, 25-diol, cycloart-25-en-3β, 24-diol, trisnorcycloartanoloic acid acetate and caffeic acid. The isolation of trisnorcycloartanoloic acid acetate from a natural source is the first example.
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