YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Volume 97, Issue 1
Displaying 1-23 of 23 articles from this issue
  • MASARU KIDO, HIDEO MORI, SONOMITSU MASUDA, HIDEAKI KOHRI, KAZUYUKI NAK ...
    1977 Volume 97 Issue 1 Pages 1-4
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    It was found that 5-(3-tert-butylamino-2-hydroxypropoxy)-3, 4-dihydrocarbostyil hydrochloride (OPC-1085) fluoresced strongly when irradiated in HCl solution and that this fluorescent substance was 5-(3-tert-butylamino-2-hydroxypropoxy)carbostyril (dehydro-OPC-1085) by a spectroscotic methods. OPC-1085 can be determined by applying this fluorescence phenomenon. The determination of OPC-1085 in plasma was performed according to the following method. OPC-1085 was extracted from plasma with chloroform. The chloroform solution was divided into two equal parts, to each of which 1N HCl or 1N HBr solution was added. Each acid solution was irradiated by a tungsten lamp for 80 min. Difference in fluorescence intensity of the two solutions was measured at 460 nm, excited at 310 nm, since the fluorescence reaction is not observed in the HBr solution. The minimum determinable concentration was 0.1μg/ml in plasma.
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  • YOSIO SUZUKI
    1977 Volume 97 Issue 1 Pages 5-13
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Many novel amide derivatives of higher fatty acids were synthesized to study the relationship between chemical structure and the serum cholesterol-lowering activity in mice. In a series of cyclohexylamides of higher fatty acids, the cholesterol-lowering activity was enhanced with increasing number of carbon atoms and number of unsaturated double bonds. Introduction of substituents into the cyclohexyl ring of N-cyclohexyllinoleamide did not increase the cholesterollowering activity, while significant improvement of the activity was observed by introduction of a methyl group or a chlorine atom into the phenyl ring of N-phenyllinoleamide. In all the substituted groups tested except the acetyl group, derivatives substituted at 2-position in the N-cyclohexyl-and N-phenyl-linoleamides showed a higher activity than these substituted in other positions. As a result, N-(2-methyl-6-chlorophenyl) linoleamide was found to be the most potent agent in the present study.
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  • SHIGEO TANAKA, CHIEKO HOSHINO, YASUMASA IKESHIRO, MAMORU TABATA, MASAO ...
    1977 Volume 97 Issue 1 Pages 14-17
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    The crude drug Toki used in Japan is classified largely into "Yamato Toki" and "Hokkai Toki", which are prepared from the roots of Angelica acutiloba var. acutiloba KITAGAWA and A. acutiloba KITAGAWA var. vugiyamae HIKINO, respectively. Anti-nociceptive effect of these crude drugs of Toki was assayed by the acetic acid-induced writhing test on mice. The results of the experiments have shown that the aqueous extract of Yamato Toki was about 3 times as effective as that of Hokkai Toki. The anti-nociceptive effect of the root extracts prepared from different varieties of Toki cultivated under similar conditions in the field at Kyoto were also tested by the same method. The aqueous extract of "Ibuki Toki" (A. acutiloba var. iwatensis HIKINO) was found to be as effective as that of Yamato Toki. A quantitative analysis on choline, which is known as one of the anti-nociceptive principles in the Toki extract, has indicated that the aqueous root extract of Ibuki Toki contains more choline than those of other Japanese varieties of Toki. In comparison with the Japanese varieties, the data obtained from "Kara Toki" (A. sinensis DIELS) and "Kankoku Toki" (A. gigas NAKAI) are also presented regarding anti-nociceptive activity and choline content.
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  • KAZUO KIGASAWA, KAZUMI OHKUBO, TOSHITAKA KOHAGISAWA, HIROAKI SHIMIZU, ...
    1977 Volume 97 Issue 1 Pages 18-23
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Caffeine (I) and theobromine (II) reacted with pyridine in the presence of hypochlorous acid to give N-(8-xanthinyl)pyridinium salt, which were characterised as the triiodides (IIIa and IIIc) and monoiodides (IIIb and IIId). Treatment of N-(8-caffeinyl)pyridinium iodide (IIIb) with sodium hydroxide afforded sodium 5-(8-caffeinyl)imino-1, 3-pentadien-1-olate (IV). This experiment clarified the mechanism for the color reaction of caffeine by hypochlorous acid-pyridine method.
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  • TOSHIHARU OHGOH, SATORU TANAKA, MASATOSHI FUJIMOTO, AKIFUMI KITAHARA
    1977 Volume 97 Issue 1 Pages 24-30
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Pharmacological screening with rats and mice was carried out on novel 6, 6, 8-tricyclic compounds, dibenz[b, g] [1, 5]oxazocine, dibenzo[b, g] [1, 5]thiazocine, and dimers with a 16-membered ring, especially for their central nerve action, using chlorpromazine, chlorprothixene, and imipramine as the reference compounds. Several of the compounds showed a relatively strong central nerve suppression, and a considerable number of the compounds had an anti reserpine activity. The central action of these compounds, however, was much weaker than that of the reference compounds. Some compounds were found to show a strong anti tremorine activity. Structure-activity correlation was not clear but substitution of a chlorine atom in the 3-position of the dibenz [b, g] [1, 5] oxazocine ring resulted in fortification of the central nerve suppression.
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  • TOSHIHARU OHGOH, SATORU TANAKA, MASATOSHI FUJIMOTO
    1977 Volume 97 Issue 1 Pages 31-35
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Pharmacological screening was carried out on newly synthesized dibenzo[b, g][1, 5]thiazocine dioxide derivatives, chiefly for their central nerve action. In the observation of general behavior of rats and mice, these compounds hardly showed a tendency for central nerve suppression, and showed no effect on the grooming to tactile stimuli and acetic acid induced writhing. Anti reserpine activity was seen in a considerable number of the compounds but this activity was fairly weak. Anti tremorine action was seen in a number of these compounds, ED50 values of anti tremorine tremor effect of six compounds with strong activity were measured and the values were compared with those of other anti-parkinsonism drugs. Three compounds with especially strong activity were submitted to LD50 measurements.
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  • KEIJI SEKIGUCHI, MOTOHARU IWATSURU
    1977 Volume 97 Issue 1 Pages 36-40
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    The dual-wavelength spectrophotometer was employed to determine the protein-binding quantity between bovine serum albumin (BSA) and Acid Violet 6B (AV, C.I. 42640) which was used as a model compound. With the aid of a double-beam spectrophotometer, the two wavelengths (542 and 599 nm) were chosen on a basis of the magnitude of the absorbance change due to protein binding. The Beer's law held at 542 nm. Linearity was recognized between the AV concentrations and their absorbances, though the Beer's law did not hold at 599 nm. Therefore, the proportionality was observed between the AV concentrations and the absorbances measured with the dual-wavelength spectrophotometer by resetting the origin to the point of intersection of the two concentration-absorbance lines stated above. The double reciprocal plots were constructed from BSA concentrations and absorbances measured by the dual-wavelength mode, and the assumed absorbances of bound dye were read off by extrapolations. The amount of bound dye was estimated from the extrapolated values, and Scatchard's plots were made. From the linear part of the curves, the number of binding site(s) n and the binding constant K were determined to be 0.9-0.4 and 7.5×106 to 13×106M-1 respectively, depending on BSA concentration.
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  • CHIYO MATSUBARA, KIYOKO TAKAMURA
    1977 Volume 97 Issue 1 Pages 41-45
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    The formation of mixed ligand complexes in Ti(IV)-Xylenol Orange(XO)-H2O2, Ti-(IV)-Chromazurol S(CAS)-H2O2, Ti(IV)-ethylenediaminetetraacetic acid (EDTA)-H2O2, and Co(II)-EDTA-H2O2 systems was studied by spectrophotometry. In Ti(IV)-XO-H2O2 system, the constant absorbance (λmax 562 nm) was obtained under the condition of [XO]/[Ti(IV)]≥1 in the pH 2-4 region. When [CAS]/[Ti(IV)] ratios were within 3-6, Ti(IV)-CAS-H2O2 system gaved distinct maximum at 557 nm in the pH range of 4.5-5.2. The absorption spectra of Ti(IV)-EDTA-H2O2 (pH 1-8) and Co(II)-EDTA-H2O2 (containing≥0.01N NaOH) systems exhibited maxima at 365 and 580 nm, respectively. In all cases, the absorbance at λmax was stable and proportional to the concentration of H2O2. The conditions for the colorimetric determination of H2O2 using M-Y reagents (M=meta1 ion, Y=chelating agent) were examined in detail. The reagents were found to be applicable to the determination of H2O2 in the following concentration ranges : Ti(IV)-XO reagent, 3×10-6 to 1×10-4M H2O2; Ti(IV)-CAS reagent, 2×10-6 to 5×10-5M H2O2; Ti(IV)-EDTA reagent, 1×10-5 to 2×10-3M H2O2 and Co(II)-EDTA reagent, 5×10-4 to 1×10-2M H2O2. Ti(IV)-XO and Ti(IV)-CAS reagents may be significant for the determination of traces of H2O2. Co(II)-EDTA reagent may be useful for the detection of H2O2, because of the intense violet coloration by the formation of Co(II)-EDTA-H2O2 complex.
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  • MASAHARU UENO, MASAAKI MIYATA, HIROSHI KISHIMOTO, YOSHIMASA KYOGOKU
    1977 Volume 97 Issue 1 Pages 46-51
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    The complex formation of tetranactin with Na, K, Rb, and Cs thiocyanates in methanol and acetone-d6 was examined by infrared and 1H-nuclear magnetic resonance spectra measurements. The equilibrium constants of complex formation were obtained from the analysis of the spectra and were compared with each other with respect to the kind of cation and solvent. The ion-selectivity of tetranactin was explained mainly by the difference among ionic species with respect to the changes of ionic solvation and tetranactin conformation due to complex formation.
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  • SEIGO FUKUSHIMA, AKIRA UENO, KAZUKO NORO, KIKUE IWAGAYA, TADATAKA NORO ...
    1977 Volume 97 Issue 1 Pages 52-57
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Four new pyrimido-1, 4-diazepine derivatives, 2, 4, 6, 8-tetramethyl-3H-pyrimido[4, 5-b]-[1, 4]diazepine-7, 9(6H, 8H)-dione (IV), 2, 4-diphenyl-6, 8-dimethyl-3H-pyrimido[4, 5-b][1, 4]-diazepine-7, 9(6H, 8H)-dione(VII), 4-phenyl-2, 6, 8-trimethyl-3H- pyrimido[4, 5-b][1, 4]-diazepine-7, 9(6H, 8H)-dione(X), and 2-phenyl-4, 6, 8-trimethyl-3H-pyrimido[4, 5-b][1, 4]-diazepine-7, 9(6H, 8H)-dione(XI), were synthesized. When 5, 6-diamino-1, 3-dimethyluracil(I) was heated in butanol with acetylacetone, dibenzoylmethane, or benzoylacetone, 4-(6-amino-1, 3-dimethyl-2, 4-dioxo-1, 2, 3, 4-tetrahydro-5-pyrimidylamino)-3-penten-2-one (III), 1, 3-diphenyl-3-(6-amino-1, 3-dimethyl-2, 4-dioxo-1, 2, 3, 4-tetrahydro-5-pyrimidylamino)-2-propen-1-one(V), or 1-phenyl-3-(6-amino-1, 3-dimethyl-2, 4-dioxo-1, 2, 3, 4-tetrahydro-5-pyrimidylamino)-2-buten-1-one (IX) were obtained, respectively, under elimination of water. Heating of I with acetylacetone, dibenzoylmethane or benzoylacetone in polyphosphoric acid afforded IV, VII, or X, were and in the case of heating I with benzoylacetone, XI was obtained in a poor yield besides X. IV, VII, and X were also obtained by heating III, V, and IX in polyphosphoric acid.
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  • SADAO UCHIYAMA, ZENZO TAMURA
    1977 Volume 97 Issue 1 Pages 58-64
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    By the addition of acetaldehyde into the reaction system, the fluorescence determination of dulcin3) was improved by enhancing the fluorescence intensity five times. By the use of a similar reaction system, a new qualitative test of dulcin by a thin-layer chromatographic method was developed, in which the detection limit was 20 times lower than that of the conventional one. In addition, aniline derivatives, especially p-anisidine and p-phenetidine, were detected with a high sensitivity by the present method.
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  • TAKEICHI SAKAGUCHI, TADAO FUJITA
    1977 Volume 97 Issue 1 Pages 65-69
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Mercury, cadmium, and zinc complexes of cytosine and isocytosine were synthesized from methanol solution. The coordination site of the ligands was examined by means of infrared, proton magnetic resonance, and mass spectroscopic analyses. Based on these data, it was concluded that metals were coordinated at N(3), N(1), or NH2 of cytosine and isocytosine, and that composition of the comp1exes was either a 1 : 1 or 2 : 1 ratio of the ligand to the metal.
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  • YASUHIRO YAMANE, NOBUYUKI YAMAJI, TADASHI OGASHIWA, MOTOICHI MIYAZAKI
    1977 Volume 97 Issue 1 Pages 70-75
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Decarboxylation of oxalacetic acid by metal chelates was investigated, using copper-(II) and manganese(II) as metals and seven amino acids, glycine, alanine, threonine, serine, glutamic acid, lysine, and histidine as ligands. All of the amino acids used here were of L form. When the concentration ratio of copper to the ligand was 1 : 1, all copper-amino acid systems showed more enhanced decarboxylation activity than that of copper(II) ion alone. In copper-amino acid, a linear relation was observed between pKa of the amino acid and the decarboxylation rate of oxalacetic acid ; as pKa values of both carboxyl and amino groups of the ligand became smaller, decarboxylation of oxalacetic acid became faster. Among the copper-amino acid systems, copper-histidine exhibited the fastest reaction rate, and, therefore, histamine and imidazole were also examined as the ligand in order to interpret the activity of histidine. Catalytic activity of manganese-amino acid was smaller than that of the corresponding copper-amino acid and the former did not show a clear relation observed in the latter. For copper-amino acid, a similar mode of the reaction was observed between decarboxylation of oxalacetic acid and hydrolysis of diisopropylphosphofluoridate.
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  • YASUHIRO YAMANE, NOBUYUKI YAMAJI, TADASHI OGASHIWA, MOTOICHI MIYAZAKI
    1977 Volume 97 Issue 1 Pages 76-81
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Effect of the metal-peptide systems on decarboxylation of oxa1acetic acid was examined, using copper(II), manganese(II), and nickel(II) as metals, and as peptide ligands, glycyl-glycine glycyl-alanine, glycyl-leucine, glycyl-threonine, glycyl-tyrosine, alanyl-glycine, leucyl-glycine, alanyl-alanine, histidyl-histidine, glycyl-glycyl-glycine, and glycyl-g1ycyl-g1ycy1-glycine. Among the metal-dipeptide systems, the fastest decarboxylation was observed when copper or manganese to His-His ratio was 1 : 1. None of the nickel-dipeptide systems decarboxylated oxalacetic acid faster than nickel(II) ion did. Decarboxylation studies were carried out at the rate of metal to ligand of 1 : 1, using copper(II), nickel(II), and manganese(II) as metals, and amino acid, di-, tri-, and tetra-peptide as ligands. The reaction rate for copper ligand decreased in the order of Gly>Gly-Gly>Gly-Gly-Gly=Gly-Gly-Gly-Gly for nickel-ligand in the order of Gly>Gly-Gly=Gly-Gly-Gly=Gly-Gly-Gly-Gly, and for manganese-ligand, in the order of Gly<Gly-Gly<Gly-Gly-Gly=Gly-Gly-Gly-Gly.
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  • HIDEO NAGANO, CHITOSE TODA
    1977 Volume 97 Issue 1 Pages 82-86
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    2'-Butylthiothiamine (II), 2'-butylthiamine (III), 4-amino-2-butylthio-5-hydroxy-methylpyrimidine (V), and 4-amino-2-butyl-5-hydroxymethylpyrimidine (VI) were synthesized and their inhibitory effect on the growth of thiamine-requiring Kloeckera apiculata and Lactobacillus fermenti was compared with thiamine antagonists such as 2'-methylthiothiamine (I) and 4-amino-5-hydroxymethyl-2-methylpyrimidine (IV). Effectiveness of these compounds as an inhibitor for Kl. apiculata decreased in the order of I, III, II, IV, V, and VI, and that for L. fermenti in the order of II, I, IV, V, and VI. III did not show any inhibitory effect on the growth of L. fermenti. The inhibition of thiamine derivatives, but not of pyrimidine derivatives, was recovered by thiamine, Effect of these compounds were examined on the growth of Lactobacillus arabinosus, which does not require thiamine for its growth. I, III, and VI did not show any inhibitory effect, but II and V which have a butylthio group in their structure showed an inhibitory effect, suggesting that there are some differences between I and II in their inhibitory effect on the growth of microorganisms.
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  • CHIAKI TANI, KIYOSHI TAGAHARA
    1977 Volume 97 Issue 1 Pages 87-92
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    (±)-Stylopine[N-14CH3] methochloride, L-methionine[S-14C] or DL-methionine-[S-13C] was administered by the cotton wick method to Corydalis incisa PERS in May and corynoline (1) was isolated. L-Methionine[S-14C] and DL-methionine[S-13C] were incorporated into corynoline (1) The positions labeled in corynoline (1) were determined to be the methylenedioxy, C-methyl and N-methyl groups by the degradation reaction and 1H-NMR spectrum.
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  • CHIAKI TANI, KIYOSHI TAGAHARA
    1977 Volume 97 Issue 1 Pages 93-102
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Protopine[13-3H2] (8b) and α- and β-tetrahydrocoptisine[N-13CH2] methochloride (10a and 10b) were administered to Papaver rhoeas L. in May by the cotton-wick method, and rhoeadine (9) was isolated. Radioactivity from 8b and 10a was incorporated into rhoeadine. The labeled position in 9 was determined by the degradation reaction and from 13C-nuclear magnetic resonance spectrometry.
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  • HIROMASA NAKAMOTO, YUKI IWASAKI, HARUHISA KIZU
    1977 Volume 97 Issue 1 Pages 103-105
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    From the aqueous extract (MTF-101) of Puerariae radix, daidzin (daidzein-7-glucoside) was isolated in 0.14% yield. The hypothermic effect of daidzin on rats and its spasmolytic effect on mice were examined in comparison with those of daidzein. Neither daidzin nor daidzein showed a hypothermic effect in a dose of 30 mg/kg s.c. on rats. Daidzein showed about 1/3 spasmolytic effect of papaverine on the small intestine of mice but daidzin showed no spasmolytic effect.
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  • YOSHINOBU AKADA, SADAKO KAWANO, TATSUHITO KONDO, TOSHIO SATO, YAICHIRO ...
    1977 Volume 97 Issue 1 Pages 106-108
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    A rapid estimation method utilizing high-speed liquid chromatography is described for determination of ascorbic acid 2-sulfate (AsS). Separation can be achieved within 6 min employing a 1-m column packed with Zipax SAX using 0.0005 M Na2B4O7-0.05 M NaClO4 (93 : 7, v/v) (pH 7.0) solution as an eluant in a Du Pont LC 830 liquid chromatograph. Typical chromatogram obtained by this method are shown. Precision in this method was found to be less than ±2.0% with the relation Y=0.31X+0.07 and a relative coefficient of 0.999. The limit of detection was 40 ng. AsS from human urine was examined by this analytical method. The peak component was identified by ultraviolet absorption spectra and thin-layer chromatography as AsS.
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  • SHUZO TAKAGI, MASAE YAMAKI, KYOKO MASUDA, MARIKO KUBOTA, JUNKO MINAMI
    1977 Volume 97 Issue 1 Pages 109-111
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    From the flowers of Prunus persica BATSCH., kaempferol-3-rhamnoside, quercitrin, multiflorin A and B were isolated and also multinoside A, which have already been obtained from Rosa multiflora THUNB., and in addition, chlorogenic acid was isolated and identified with an authentic sample. The purgative activity of extracts of Prunus persica is stronger than that of Rosa multiflora and probably depends on multiflorin A and other factors, which are discussed in detail.
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  • YUKIHO KUBOTA, SHOZO SHOJI, KUNIO MOTOHARA
    1977 Volume 97 Issue 1 Pages 111-115
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    A prolidase was separated from germinating soybean(Glycine Max. AKIYOSHI) in a highly purified form by using ammonium sulfate precipitation, DEAE-cellulose chromatography, and Sephadex gel filtration. The enzyme liberated glycine from Gly-Pro and G1y-Sar. The specific activity of purified prolidase was 1.65 units/mg of protein for G1y-Pro. The enzyme did not possess Gly-Gly dipeptidase, Gly-Gly-Gly tripeptidase, aminopeptidase, carboxypeptidase, or endopeptidase activity. It had a pH optimum at 7.0 for Gly-Pro and exhibited maximum activity at 40° when incubated for 120 min. The values of s20, w and D20, w were 5.5 S and 6.6×10-7 cm2/sec, respectively, and the molecular weight was calculated to be 78000 from these values.
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  • ATSUKO NOSE, TADAHIRO KUDO
    1977 Volume 97 Issue 1 Pages 116-120
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    Azoxybenzene(II), azobenzene(III), and aniline(IV) were formed by the reaction of nitrobenzene(I) with sodium borohydride at 180-200° in the absence of a solvent. In this reaction, increasing concentration of sodium borohydride increased the yield of IV and decreased that of II. Similarly, reduction of o-nitrotoluene(V), m-nitrotoluene(VI), p-nitrotoluene(VII), p-methoxynitrobenzene(VIII), and p-chloronitrobenzene(IX) gave the corresponding amine and azo derivatives. In order to clarify this reaction mechanism, the same reaction of reduced derivatives, such as nitrosobenzene(XX), N-phenylhydroxylamine (XXI), hydrazobenzene(XXII), and III, was examined and all these derivatives gave IV, but its yield was poor in the reduction of III.
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  • MITSUO MIYAZAWA, HIROMU KAMEOKA
    1977 Volume 97 Issue 1 Pages 120-122
    Published: January 25, 1977
    Released on J-STAGE: May 30, 2008
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    The essential oil of Eupatorium japonica THUNB. collected in Osaka was examined. The yield of flower oil was about 0.71%, oil of the stem was 0.03%, and that of the leaf was 0.66%. The essential oils were separated into individual components by a combination of chemical method and preparative gas chromatography or elution chromatography. Forty-three compounds in the oils were characterized.
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