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Part I. Formation of Volatile Components during Black Tea Manufacture
Ryoyasu SAIJO, Yoshio KUWABARA
1967 Volume 31 Issue 4 Pages
389-396
Published: 1967
Released on J-STAGE: November 27, 2008
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The volatile components extracted from fresh tea leaf, fermented leaf and black tea were analysed by gas chromatography.
Quantitative difference in the composition of essential oils was observed between fresh leaf and manufactured black tea; the former was rich in alcohols, whereas the latter in aldehydes and acids.
During fermentation process the following components mainly brought about changes:
n-capronaldehyde (4.1 times after fermentation for 3hrs.),
trans-2-hexen-l-al (13.2 times) and
cis-3-hexenoic acid (1.2 times) increased, but
n-hexylalcohol (0.7 time),
cis-3-hexen-l-ol (0.7 time) and methylsalicylate (0.8 time) decreased.
These changes during fermentation were scarcely carried out in nitrogen atmosphere.
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Part III. Synthesis of Certain Substituted Phenyl α-L-Rhamnosides
Shintaro KAMIYA, Sachiko ESAKI, Misao HAMA
1967 Volume 31 Issue 4 Pages
397-401
Published: 1967
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In order to investigate the substrate-specificity of α-L-rhamnosidase induced in Aspergillus species, the titled compounds were synthesized employing the various kinds of methods.
One is the Helferich reaction by using the sirupy L-rhamnose teteraacetate and appro-priate phenols in the presence of
p-toluenesulphonic acid or zinc chloride etc. The other method is Königs-Knorr reaction by using triacetyl α-L-rhamnosyl bromide and appropriate phenols in the presence of mercuric salts. The excellent result was obtained by the former method than the latter one. Deacetylation of the resulting esters (MeOH-NaOMe) gave the titled compounds.
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Part IV Synthesis of Naringin and Neohesperidin
Shintaro KAMIYA, Sachiko ESAKI, Misao HAMA
1967 Volume 31 Issue 4 Pages
402-409
Published: 1967
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Naturally occurring flavanone-7-neohesperidoside, naringin and neohesperidin contained in citrus peels were synthesized. β-Neohesperidose heptaacetate was treated with hydrogen bromide in acetic acid, giving hexaacetyl α-neohesperidosyl bromide. The latter compound coupled with phloroacetophenone in the presence of silver carbonate in quinoline yielded phloroacetophenone-4-neohesperidoside after deacetylation.
Condensation of phloroacetophenone-4-neohesperidoside with
p-hydroxybenzaldehyde and isovanilline respectively in the presence of strong alkali afforded the corresponding chalcone-neohesperidosides, which were converted by ring closure to naringin and neohesperidin respectively.
Furthermore, the reactivity among phloroacetophenone-4-glycosides, namely β-D-gluco-side, β-D-xyloside, and β-neohesperidoside and fifteen kinds of substituted benzaldehydes was investigated. Phloroacetophenone-4-β-D-glucoside reacted with
p-hydroxybenzaldehyde, p-anisaldehyde isovanillin and protocatechualdehyde. In the case of phloroacetophenone-4-β-D-xyloside the same result was obtained except the case of protocatechualdehyde.
In the case of phloroacetophenone-4-neohesperidoside reacted only with p-hydroxybenz-aldehyde and isovanillin.
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Part II. Comparative Study of Hydrolysis Rate and Ovicidal Activity
Shuichi ISHIDA, Mitsuo IDA
1967 Volume 31 Issue 4 Pages
410-416
Published: 1967
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Formation of a sulfonium-like intermediate was assumed in the hydrolysis of the 2-bromoethylthiobenzenes. A linear free energy relationship was found between the hydrolysis rate of a certain substituted 2-bromoethylthiobenzene and the molar fraction of water in the solvent. The effect of the substituent on the rate constant was attributed not only to the activation energy but also to the entropy change of activation. The negative ρ-value in the formation of the sulfonium-like intermediate in aqueous solution was comparable with that obtained in the ρ-
o-π analysis for ovicidal activity of the compounds.
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Part III. Comparative Study of Rate of Alkylating Reaction and Ovicidal Activity
Shuichi ISHIDA, Osamu YAMADA
1967 Volume 31 Issue 4 Pages
417-421
Published: 1967
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For the reaction of the substituted 2-bromoethylthiobenzenes with highly excess amount of 4-(
p-nitrobenzyl)-pyridine, the ρ-value was found to be negative, which means that the formation of the sulfonium-like intermediate is a rate determining step. Whichever might be more important, the hydrolysis or alkylation, as to the ovicidal action of the compounds, the formation of the sulfonium-like intermediate, could be considered to be an essential step.
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Yorinao INOUE, Kôzô ISHIZUKA, Shingo MITSUI
1967 Volume 31 Issue 4 Pages
422-427
Published: 1967
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In order to elucidate the mode of action of some herbicides, effect of several anilide type herbicides on the respiration of yeast cells was studied. The results obtained were as follows: 1) DCPA (3, 4-dichloropropionanilide) and DCMU (3-(3, 4-dichlorophenyl)-l, l-dimethylurea), the powerful inhibitors of the Hill reaction in photosynthesis, inhibited the oxygen uptake of yeast cells at low concentrations. 2) DCPA and DCMU inhibited the enzymic reduction of cytochrome-c by the yeast cell-free preparation, but not the reduction of dye. 3) The oxidation of cytochrome-b was inhibited in the yeast cells treated with DCPA or DCMU.
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Fuji UCHINO, Yoshiaki KURONO, Shinji DOI
1967 Volume 31 Issue 4 Pages
428-434
Published: 1967
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A crystalline acid protease produced by a strain of
Acrocylindrium in a submerged culture was prepared by treatment with acetone (60%), salting out with ammonium sulfate (saturated) and, after chromatography on Duolite CS-10l column, dialysis against distilled water. This preparation was homogeneous on sedimentation analysis, starch-gel electro-phoresis and gel filtration with Sephadex G-75. The optimum pH was 2.0 for milk casein digestion and the pH stability was for 2.0_??_5.0 at 30°C for one day. The crystalline enzyme was completely stable below 50°C, but lost the activity at 70°C in ten minutes. The acid protease was almost equal to pepsin on specific activity when milk casein solution (pH 2.0) was used as substrate.
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Yoshiyuki TAKASAKI
1967 Volume 31 Issue 4 Pages
435-440
Published: 1967
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The equilibrium constant of the isomerization reaction between D-mannose and D-fructose which is catalyzed by a mannose isomerase from
Streptomyces aerocolorigenes was obtained by using three methods over the temperature range from 1 to 40°C.
It was found that the equilibrium constant was scarcely dependent on temperature,
ΔH, the heat of the formation of D-fructose from D-mannose, being approximately zero.
The standard free energy change,
ΔG, and the standard entropy change,
ΔS, of the reaction were calculated from the equilibrium constants at various temperatures and
ΔH. The values of
ΔG and
ΔS at 25°C were -650 cal/mole and +2.2 cal/deg.mole, respectively.
By combining these thermodynamic data with those obtained for the isomerization reaction between D-glucose and D-fructose reported in the previous paper,
ΔH,
ΔG and
ΔS for the isomerization between D-mannose and D-glucose were indirectly obtained to be +2220 cal/mole, +830 cal/mole and +4.6 cal/deg. mole at 25°C, respectively.
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Part I. Lipid Composition of Streptomyces sioyaensis and its Comparison with those of Various Strains of Actinomycetales
Akira KIMURA, Jun'ichi KAWANAMI, Hideo OTSUKA
1967 Volume 31 Issue 4 Pages
441-447
Published: 1967
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Three ninhydrin-positive lipids of
Streptomyces sioyaensis were found. These lipids were called substance A, B and C, tentatively. Study on the distribution of these lipids in
Actinomycetales has shown that substance A was common in all of the strains tested, and that substance B was found in the limited strains. The substance C was characteristic only in
Streptomyces sioyaensis.
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Zen-ichiro HAMAUZU, Daizo YONEZAWA, Hiromu SHIMOMURA
1967 Volume 31 Issue 4 Pages
448-451
Published: 1967
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Albumin preparations from four kinds of wheat flour (Durum, Manitoba No. 2, Western White and Norin No. 26) were analyzed by immunoelectrophoresis. Seven to eleven components were detected for each preparation. They were classified and designated on the basis of the electrophoretic mobility (
R) and the character of precipitin lines formed by antigen-antibody reactions.
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Part II. The Structure of Cocculolidine
Kojiro WADA, Shingo MARUMO, Katsura MUNAKATA
1967 Volume 31 Issue 4 Pages
452-460
Published: 1967
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An insecticidal alkaloid, cocculolidine was extracted from fresh leaves of
Cocculus trilobus DC. Von Braun reaction and a novel acid catalyzed degradation showed that this alkaloid had the same skeleton with those of erythrina alkaloids. Structure (I) was finally assigned to cocculolidine, being identified as a new lactone erythrina alkaloid con-taining α, β-unsaturated-γ-lactone. The mass spectra of I and dihydro-β-erythroidine were also discussed.
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Part II. Tocored as a Precursor of Color Reversion of Soybean Oil
Mamoru KOMODA, Noriji ONUKI, Ichiro HARADA
1967 Volume 31 Issue 4 Pages
461-469
Published: 1967
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Tocored as a precursor of color reversion of soybean oil has been isolated and identi-fied. We have found that the moisture of raw soybeans is closely related to the tocored content in crude oil and the yield of tocored is maximum when the moisture of soybeans is 15_??_18%. It seemed that tocored in crude oil were completely removed by the refining processes, but 30% of it remained in the colorless form in refined and deodorized oil and turned into tocored during storage or on heating the oil to a higher temperature. Tocopherols are relatively stable in refined oil and are not oxidized to tocored under a milder condition, such as the oxidation with air. Neither tocopherol nor tocored but “tocored in colorless form” is really the precursor of color reversion in soybean oil.
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Mikio SATO, Hajime TAKAHASHI
1967 Volume 31 Issue 4 Pages
470-474
Published: 1967
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Crude cell-free extracts from
Cellulomonas flmi contain cellobiose phosphorylase which cleaves cellobiose into glucose and glucose- l-phosphate in the presence of inorganic phosphate. With the aid of this enzyme, two samples of C
14-cellobiose labeled in reducing or non-reducing glucosyl moiety were prepared from uniformly labeled C
14-glucose or C
14-glucose-1-phosphate as substrate, respectively. The labeled preparations have been shown to be radiochemically pure. Analyses of the anaerobic fermentation products from C
14-cellobiose by resting cell suspensions showed that both glucose moieties were fermented almost equivalently. However, relatively small differences in specific activities of the products revealed that significantly larger amounts of formic acid and smaller amounts of acetic acid were produced from the reducing glucose moiety than from the other half of the molecule. Succinic and lactic acids appeared to be produced almost equally from both moieties.
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Part II. Chemical Properties of Various Fractions of “Ghosts”
Tsutomu YAMAGUCHI, Norihiro TSUKAKOSHI, Gakuzo TAMURA, Kei ARIMA
1967 Volume 31 Issue 4 Pages
475-480
Published: 1967
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The components of fractions obtained by dialyzing and differential centrifuging the “Ghost” of
Bacillus megaterium were analyzed in detail. The compositions of amino acids in the main fractions (Fraction 2 and 3) of the “Ghosts”, were estimated. Fraction 2 was rich in non-polar amino acids, while Fraction 3 was scanty of them. Most of the fatty acids in Fraction 2 were 12-methyl tetradecanoic acid, while in Fraction 3 many kinds of fatty acid were detected.
As for the localization of enzymes, the three enzymes, glucose oxidase, succinic dehydrogenase and reduced nicotinamide-adenine dinucleotide oxidase, which were present in the original “Ghosts”, were mostly observed in Fraction 2, and a very little amount of them was found in the other fractions. Further, Fraction 2 could be dissolved in formic acid and dialysis of the solution brought about reaggregation to form membrane-like structure in the presence of Ca or Mg ion.
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Keiji HARASHIMA, Nobuo TSUCHIDA, Teruo TANAKA, Junsaku NAGATSU
1967 Volume 31 Issue 4 Pages
481-489
Published: 1967
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A water-insoluble red antibiotic pigment was isolated from mycelia of a strain of
Streptomyces. It was found that the pigment is a new C
25-prodigiosin-analogue and the authors propose to designate it prodigiosin-25 C. The chemical structure (XI) has been deduced from visible absorption spectra, NMR spectra, mass spectra and analysis of degradation products of the pigment.
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Part IV. Identification of α- and γ-Glutamylaspartic Acid
Yoshinori ISHIKAWA, Shizuko HASEGAWA, Takanori KASAI, Yataro OBATA
1967 Volume 31 Issue 4 Pages
490-493
Published: 1967
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α- and γ-Glutamylaspartic acids were detected in acidic fraction of soybean seedling.
RF values of both peptides were consistent with those of authentic samples with several solvent systems.
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Part I. Isolation of Callicarpone and its Toxicity to Fish
Kazuyoshi KAWAZU, Makoto INABA, Tetsuo MITSUI
1967 Volume 31 Issue 4 Pages
494-497
Published: 1967
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A fish-killing component, which was named callicarpone, C
20H
28O
4, m. p. 111°C, [α]
23°D-188° (chloroform) was isolated from the leaf of
Callicarpa candicans and was found to have conjugated carbonyl groups, double bond and one hydroxyl group. The toxicity to fish was evaluated to be as strong as rotenone and ten times stronger than sodium pent achlorophenoxide.
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Part II. Structure of Callicarpone
Kazuyoshi KAWAZU, Makoto INABA, Tetsuo MITSUI
1967 Volume 31 Issue 4 Pages
498-506
Published: 1967
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It was deduced from the spectral data of callicarpone (I), the tetraol (IV), the chloro-hydrin (VII) and the anhydro-diacetyl derivative (II) that I was_??_tricarbocyclic diterpene having an ene-l, 4-dione and an α-hydroxy-isopropyl attached to an oxide ring. The struc-ture of the rearranged product obtained by treatment with sodium carbonate was established to be IX by converting it to 11-methoxy-ferruginol methyl ether. As this rearrangement was assumed to be initiated by proton abstraction by base, the structure I was required for callicarpone to explain the formation of IX.
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Eiji ICHISHIMA, Fumihiko YOSHIDA
1967 Volume 31 Issue 4 Pages
507-510
Published: 1967
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Kiyoshi NAKAYAMA, Hiroshi HAGINO
1967 Volume 31 Issue 4 Pages
511-512
Published: 1967
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