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Volume 22, Issue 11
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TAKEO HIGASHINO, MASAMI GOI, EISAKU HAYASHI1974 Volume 22 Issue 11 Pages 2493-2501
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe possible reaction process for the formation of 4, 4'-biquinazoline (II) obtained from the reaction of quinazoline (I) with cyanide ion were discussed and proposed by the scheme shown in Chart 1, which involved benzoin type condensation and oxidation, in successive step. When the mixture of I and aromatic aldehyde treated with cyanide ion, aryl 4-quinazolinyl ketone (IX) was obtained together with II, even if both of the yields were poor. Typically, in the case of o-anisaldehyde and m-chlorobenzaldehyde, 2-methoxyphenyl 4-quinazolinyl ketone (IX-2), 3-chlorophenyl 4-quinazolinyl ketone (IX-6) and α-(2-methoxyphenyl)-4-quinazolinemethanol (VII-2), α-(3-chlorophenyl)-4-quinazolinemethanol (VII-6) were respectively obtained together with II. The reaction with benzaldehydes which was substituted with strongly electron donating (such as dimethylamino and hydroxyl group) or strongly electron attracting group (such as nitro and cyano group) did not give any of the corresponding IX. Especially, in the case of nitrobenzaldehyde, the corresponding dimethyl azodibenzoate (XV) and dimethyl azoxydibenzoate (XVI) were obtained. Although there were the two possible reaction process for the formation of IX, path A and B, which were similar to that of cross benzoin condensation and oxidation in successive step, it might be considered that this cross benzoin type condensation might proceed by path A rather than path B.View full abstractDownload PDF (827K) -
HIDEYO SHINDO, EIICHI NAKAJIMA, NOBUHIRO MIYAKOSHI, EIJI SHIGEHARA1974 Volume 22 Issue 11 Pages 2502-2510
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe distribution, excretion and metabolism of 14C-labeled pancuronium bromide following intraperitoneal administration to rats were investigated by means of wholebody autoradiography and radioassay. The distribution of dimethyl-d-tubocurarine-14C iodide was also investigated in mice for comparison. Pancuronium-14C bromide was found to be accumulated rapidly in the liver, kidney and cartilage tissues such as the sternum, vertebra and trachea and slowly in the bone marrow and spleen, while no accumulation was observed in the muscular tissues and central nervous system. The accumulation in the liver continued for a long period and almost disappeared after 30 days survival. Counting of the liver radioactivity revealed that approximately 8, 2.5, 1.2 and 0.5% of the dose remained in the liver after 1, 6, 20 and 30 days, respectively ; the concentration decreased with half-life of about 11.2 days after an initial decline with half-life of about 1.2 days. It was confirmed that pancuronium bromide is excreted mainly via urine, mostly in the unchanged form. Dimethyl-d-tubocurarine-14C iodide showed a distribution pattern similar to that of pancuronium-14C bromide. The distribution pattern of pancuronium ion was thus quite similar to that of decamethonium ion, except that the latter accumulates in the muscular tissues. This is considered to be related to the fact that decamethonium is a depolarizer at the neuromuscular junctions, while both pancuronium and d-tubocurarine is a competitive depressant. It was also indicated that the extent of accumulation of bis-onium structure in the liver is determined not by the lipophilic character of the molecule, but primarily by the distance separating the two quaternary nitrogens.View full abstractDownload PDF (1323K) -
TAKASHI HIRAOKA1974 Volume 22 Issue 11 Pages 2511-2517
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA determination of microquantity of ethylphenylephrine in plasma of dogs and human volunteers after oral administration of a therapeutic dose was investigated by the radioisotope derivative method using p-toluenesulfonyl [35S] chloride (tosyl [35S] chloride). Tosyl chloride, in a weak alkaline medium containing 33% acetone, reacted with the phenolic hydroxyl and amino group of ethylphenylephrine molecule, producing N-tosylethylphenylephrine tosylate, and reacted with the phenolic hydroxyl group of the drug in a neutral medium, producing ethylphenylephrine tosylate. A linear correlation was found between the amount of ethylphenylephrine (0.0125-0.1μg) added to human plasma and the radioactivity of N-tosylethylphenylephrine tosylate-35S derivative produced from ethylphenylephrine which was extracted from the plasma samples. After the administration of ethylphenylephrine in dogs, about 56-80% of total plasma level was found as unchanged drug in plasma. On the contrary, unchanged ethylphenylephrine was not detected in human plasma after oral administration of the drug. After oral administration of the sustained-release capsule, plasma level was compared with that of the uncoated tablet in man and it was found that increase of plasma level was slower and more durable after administration of the sustained-release capsule than that of the uncoated tablet. Thus, the radioisotope derivative method using tosyl [35S] chloride was useful for determination of a microquantity of ethylphenylephrine or its metabolite in plasma.View full abstractDownload PDF (891K) -
HIDEAKI UMEYAMA1974 Volume 22 Issue 11 Pages 2518-2529
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was shown by Garrett (1957) that the addition of ethanol to water increased the rate of the solvolysis of aspirin. The solvolysis of aspirin derivatives has been studied by many researchers. However, the mechanism was not able to be explained. In this report, the mechanism of the solvolysis of aspirin derivatives were studied from the quantum chemical point of view by using the Complete Neglect of Differential Overlap/2 method. First, the hydrolysis of phenyl acetates as classical general base catalysis were explained theoretically. Secondly, the solvolysis of aspirin derivatives as concerted general base catalysis were explained theoretically. Thirdly, the solvolysis by using the groups concerned with the solvolysis of aspirin were explained theoretically. The reasonable structures of the solvolysis of aspirin derivatives were obtained, and the mechanism of the solvolysis was explained in terms of the presence of water in the monomer state for the transition state. In addition, as the approach to the mechanism of the hydrolysis of acyl-α-chymotrypsin, the explanations similar to those of the solvolysis of aspirin derivatives were applied.View full abstractDownload PDF (1032K) -
MICHIO MATSUI, MASAKO KAWASE, MASASHI OKADA1974 Volume 22 Issue 11 Pages 2530-2537
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-14C-Androstenedione 3-enol glucosiduronate (14C-AEG) was synthesized and its stability was studied by analyzing liberated steroids. Incubation of 14C-AEG with human urine at 37° for 48 hr resulted in 49% hydrolysis. 14C-AEG was fairly stable in neutral and basic media, but rapidly hy rolyzed at acidic pH. 14C-AEG was solvolyzed almost quantitatively with acidic ethyl acetate in the same way as steroid sulfates. By incubation with β-glucuronidase (Ketodase, Helix pomatia, and bacterial β-glucuronidase) at pH 6.2 for 3 hr, 64-71% of 14C-AEG was hydrolyzed. Hydrolysis with Helix pomatia β-glucuronidase was inhibited by D-glucaro-(1→4)-lactone. Analyses of liberated steroids by TLC revealed the formation of artifacts (polar steroids) in all cases so far examined. One of them was identified as 6β-hydroxyandrostenedione.View full abstractDownload PDF (1068K) -
SHUNICHI TSUKIYAMA, AKIRA TAKAMURA1974 Volume 22 Issue 11 Pages 2538-2545
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe object of this paper is to analyze the mechanism for the deformation and breakup ■droplet on mechanical agitation. In this experiment, the droplets which had been subdivided to about 50μ by pre-agitation were still more dispersed in the agitation tank. And the values of activation energy E* and of frequency factor A were calculated. Each average diameter of drop was calculated and the following results were obtained. 1. The value of activation energy was in the range of 5×103-5×104 (erg/cm2), when particle size was about 50μ. 2. The value of frequency factor was in the range of 2×10-3-4×10-2 (1/sec), when particle size was about 50μ.View full abstractDownload PDF (726K) -
YUKIKO TANAKA, YOSHIMASA TANAKA1974 Volume 22 Issue 11 Pages 2546-2551
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe infrared (IR) spectra of bisbenzenesulfonimide, bistoluenesulfonimide and benzenetoluenesulfonimide are reported together with the spectra of the corresponding N-deuterated samples. The isotopic shifts of the bands near 3180 cm-1 and 1400cm-1 of bisarylsulfonimide derivatives give the evidence of the assignment of these bands to the N-H group. The dichroic properties of these bands in bisbenzenesulfonimide suggest that the molecule has the C2 symmetry. On this ground, the symmetric and antisymmetric S-N-S stretching bands are clearly distinguished from each other in the polarized spectra. The IR spectrum of bispentadeuterobenzenesulfonimide has been measured. The effects of the N-deuteration and the ring deuteration on the characteristic frequencies are discussed. The IR spectra of the corresponding N-alkyl-bisarylsulfonimide derivatives are also discussed.View full abstractDownload PDF (654K) -
YOSHIYASU FURUKAWA, OSAMU MIYASHITA, MIKIO HONJO1974 Volume 22 Issue 11 Pages 2552-2556
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyanoacetylene reacted with cytidine 5'-phosphate and adenosine 5'-or 3', 5'-cyclic phosphate at their corresponding base moieties to afford a new type of heterocyclic nucleotides, 2-amino-7-(5-phospho-β-D-ribofuranosyl)-pyrimido [1, 2-c] pyrimidin-5-ium-6(7H)-one (V) and 9-amino-3-(5- or 3, 5-cyclic phospho-β-D-ribofuranosyl)-pyrimido [2, 1-i] purin-6-ium (IX or XIII), respectively.View full abstractDownload PDF (615K) -
YUICHIRO YABE, KOICHI KITAMURA, CHIEKO MIURA, YOSHIHIKO BABA1974 Volume 22 Issue 11 Pages 2557-2564
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight analogues of LH-RH, in which arginine residue in position 8 was modified, were synthesized and evaluated for their LH-RH activity. The results suggest that both the size and basicity of the guanidino group, as well as the length of the methylene chain in Arg8 residue are important factors for generating full hormonal activity.View full abstractDownload PDF (978K) -
SHUN'ICHI TSUKIYAMA, AKIRA TAKAMURA1974 Volume 22 Issue 11 Pages 2565-2572
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe object of this paper is to make several models for the deformation and breakup of droplet by introducing the transition state theory into the process of liquid-liquid dispersion on mechanical agitation. On this experiment, the droplets which had been grown to about 50-60 μ pre-agitation were still more dispersed in the agitation tank, continuously. And a value of maximum shearing velosity was calculated and then a shape of deformed drop was presumed. The droplets were taken by a microscopic photograph method. Then, average diameter was mesured and the following results were obtained. 1. When the mode of deformed drop is assumed as an ellipsoid, it will be considered that a drop about 50μ will burst into two drops at the range of 330 and 530 rpm. 2. A value of maximum shearing velosity in the agitation tank becomes 3.8×103 (1/sec) at 330 rpm and 2.50×104 (1/sec) at 812 rpm, respectively.View full abstractDownload PDF (703K) -
TAKASHI NISHIRAWA, HIROAKI KUBO, MASAYUKI SAITO, SHOHEI YOSHIUE, ZENZO ...1974 Volume 22 Issue 11 Pages 2573-2577
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe presence of a new compound in human urine had been suggested from the gas chromatographic assay for urinary catecholamines. The compound was purified and identified as (±)-δ-(3, 4-dihydroxyphenyl)-γ-valerolactone mainly by the ultraviolet, infrared, mass and nuclear magnetic resonance (NMR) spectra, and chemical functional group tests. The compound was excreted in urine of most men and women, and predominantly in conjugated form.View full abstractDownload PDF (535K) -
MORIO IKEHARA, TAKEO NAGURA, EIKO OHTSUKA1974 Volume 22 Issue 11 Pages 2578-2586
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA triplet AUG analog containing 8, 2'-O-cycloadenosine in the first position was synthesized. Starting from 2'-O-(2, 4, 6-triisopropylbenzenesulfonyl)-8-bromoadenosine (I), 5'-monomethoxytrityl-8, 2'-O-cycloadenosine (IV) was synthesized via 8-oxy derivative (II) by the successive treatment with sodium acetate, monomethoxytrityl chloride and methanolic ammonia. Phosphorylation of compound IV with cyanoethyl phosphate and dicyclohexylcarbodiimide (DCC) at 18-20° for 5 days gave only 3'-cyanoethylphosphate (V) quantitatively. Treatment of V with methanolic ammonia gave 3'-phosphate (VI) in a relatively low yield with concomitant formation of 2', 3'-cyclic phosphate (VII). Compound VI was then condensed with 2'-O-benzoyluridylyl-(3'-5')-N2, 2', 3'-triisobutyrylguanosine (X) using DCC and after purification on a column of diethylaminoethyl (DEAE)-cellulose, 8, 2'-O-cycloadenylyl-(3'-5')-guanosine (XI) was obtained in a yield of 4.1%. Compound XI showed hypochromicity of 7.3% at 257 nm and circular dichroism (CD) spectra taken at 0° and 20° revealed that this trinucleotide exists in a rather freely rotatable, unstacked form both at these temperatures.View full abstractDownload PDF (928K) -
OSAMU HOSHINO, KEIKO OHYAMA, MICHINORI TAGA, BUNSUKE UMEZAWA1974 Volume 22 Issue 11 Pages 2587-2592
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLead tetraacetate oxidation of 1, 2, 3, 4-tetrahydro-6-hydroxy-7-methoxy-2-methylisoquinolines (VIIIa-d) in methylene chloride was found to form readily 4-acetoxy-1, 2, 3, 4-tetrahydro-6-hydroxy-7-methoxy-2-methylisoquinolines (XIVa-d) in moderate yield.View full abstractDownload PDF (827K) -
SHIGEO SENDA, KOSAKU HIROTA1974 Volume 22 Issue 11 Pages 2593-2598
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor investigation of the structure-activity relationship of xanthine derivatives, two new synthetic routes to 9-deazaxanthines have been found. Catalytical reduction of 6-(2-dimethylaminovinyl)-5-nitrouracils (2), which were prepared by condensation of 5-nitro-6-methyluracils (1) with dimethylformamide (DMF)-diethylacetal or DMF-dimethyl sulfate complex, gave the 2, 4-dioxo-1, 2, 3, 4-tetrahydropyrrolo [3, 2-d] pyrimidines (3) and its 6-dimethylamino relatives (4). Heating 5-formylamino-1, 3, 6-trimethyluracil (15a) also gave pyrrolo [3, 2-d] pyrimidine derivative (3a). Diuretic, cardiac, and central nervous system stimulating activities of the 9-deazaxanthines (3, 6, 9) were weeker than those of caffeine.View full abstractDownload PDF (757K) -
KAZUYO TANAKA, MICHIKO HIOKI, HIDEYO SHINDO1974 Volume 22 Issue 11 Pages 2599-2606
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPancurofnium bromide and its deacetylated metabolites were determined in human urine after intravenous administration to five patients by two methods : ion-pair extraction with bromophenol blue for the quaternary nitrogen and hydroxamic acid method for the acetyl group. Succinylcholine which was administered simultaneously was confirmed not to be extracted as the ion-pair complex at all. For the assay of the acetyl group, pancuronium and its metabolites were isolated from the urine as the ion-pair complex followed by column chromatography. The extracts were also subjected to silica gelthin-layer chromatography, wherein pancuronium and its three deacetylated metabolites could be separated while the dye went away to the top of the plate. The results revealed that approximately 20 to 50% of the dose was recovered in the urine during 24 hr period after administration, mostly in the first 3 to 4 hr period, and that pancuronium was excreted mainly as the unchanged form with a slight amount of its mono- and dihydroxy metabolites. The extractability of quaternary ammonium ions with a wide variety of structure as ion-pair complex with bromophenol blue was examined in order to find any relation to the structure. It was revealed that the extractability is determined mainly by two factors, that is, the lipophylic character of the ammonium ion and the steric effect around the cationic head and the value of the sum of π-constants for four groups plus that of Es parameters for three smallest groups can provide an approximate measure for predicting the extractability.View full abstractDownload PDF (922K) -
SHUNICHI TSUKIYAMA, AKIRA TAKAMURA1974 Volume 22 Issue 11 Pages 2607-2613
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn this paper, it is purpose to measure the agitation torque for the breakup of droplet and to require the energy efficiency of agitation in the wide range of particle size from 1μ to 100μ. The values of torque are measured by rotary torque meter adapted to the middle of rotary shaft of agitator. The photographs of drop are taken by a microscopic method. Then, each mean surface volume diameter is calculated and still more energy efficiency of agitation is required. So, the following results are obtained. 1) Agitation torque is proportional to 2.038 power of revolution number. 2) Agitation torque is proportional to 5.188 power of impeller diameter. 3) A relationship of specific interfacial area to agitation torque is shown as next experimental equation.log S=0.3994 log P+0.37575View full abstractDownload PDF (638K) -
HIROSHI AKIMOTO, KYUYA OKAMURA, MINORU YUI, TAKAYUKI SHIOIRI, MASASHI ...1974 Volume 22 Issue 11 Pages 2614-2623
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new approach to the synthesis of optically active indole and isoquinoline alkaloids is described. The key reactions are : (i) the biogenetic-type, asymmetric Pictet-Spengler reaction of optically active α-amino acids (I) with aldehydes (II) (1, 3-asymmetric induction), and (ii) the elimination of the chiral center derived from α-amino acids (1, 3-transfer of asymmetry), shown in Chart 1. To achieve (ii), laboratory simulation of decarboxylative processes of α-amino acids was investigated by oxidative and reductive methods. The former did not give any fruitful results, as shown in Table I. However, the reduction of α-amino nitriles, easily prepared from α-amino acids, by means of sodium borohydride gave the satisfactory result, as shown in Table II. By this new method, two simple indole alkaloids, (S)-(-)-tetrahydroharman (XXIV) and (S)-(-)-1, 2, 3, 4, 6, 7, 12, 12b-octahydroindolo [2, 3-a] quinolizine (XXIX) could be obtained from L-tryptophan in a satisfactory manner.View full abstractDownload PDF (1183K) -
SEIICHI UENO, YOSHINORI TOMINAGA, YOSHIRO MATSUDA, GORO KOBAYASHI1974 Volume 22 Issue 11 Pages 2624-2634
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 1, 3-dioxo- or 1, 4-dioxo-1, 2, 3, 4-tetrahydroisoquinolines (Ia, b, c) with ketenethioacetals (IIa, b, c, d, e, f) gave the corresponding substitution products (IIIa, b, c, d, e, f, IVa, b, V, VI, VII, IX, X) of methylthio group in ketenthioacetal derivatives in a good yield. The application of these reactions afforded pyrano [2, 3-c] isoquinoline and pyrrolo [1, 2-b] isoquinoline derivatives. The reaction of IIIa, b, IVa, or IVb with amines afforded recyclized products, 2-benzopyrano [3, 4-b] pyridine derivatives (XIIIa, b, c, d). The reaction of VII and IX with amines gave amino derivatives (XVIa, b, c) which were the replaced products of methylthio groups of VII and IX. The reaction of X with aminoacetal afforded an aminoacetal derivative (XVII) which was treated with hydrochloric acid to give a cyclized product (XVIII). The reaction of IX or XVIc with ethyl orthoformate or formic acid gave pyrimidine derivatives (XXa, b, XXI).View full abstractDownload PDF (1033K) -
NOBUYOSHI KANENIWA, AKIKO IKEKAWA, HUSAKO HAYASE1974 Volume 22 Issue 11 Pages 2635-2641
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInteraction of iodine with ethylene glycol, diethylene glycol, triethylene glycol and polyethyleneglycols (PEGs) of molecular weight between 2×102 and 1.1×104 in ethanol and in carbon tetrachloride was investigated. Absorbance of an ethanol solution of iodine at 360nm increased by the addition of PEGs. A new peak was observed at 380 nm by the addition of PEGs of molecular weight above 3×102 to the carbon tetrachloride solution of iodine. These findings were considered to be due to formation of iodine in the diatomic state whose interatomic distance was a little prolonged by the interaction between iodine and PEGs. Formation of iodine in the diatomic state whose interatomic distance was a little prolonged was remarkable when the molecular weight of PEG was high and the concentration of PEG was large. It was considered that the interaction force was a very weak "short-range force." From the results of the measurement of solubility of PEGs in carbon tetrachloride, optical rotatory dispersion spectra and viscosities of the solutions of PEGs, it was suggested that a PEG molecule was in spherical conformation in ethanol and that formation of iodine in the diatomic state whose interatomic distance was a little prolonged might be remarkable in the presence of PEG molecules in spherical conformation.View full abstractDownload PDF (756K) -
MINORU MACHIDA, TAKAMITSU SEKINE, YUICHI KANAOKA1974 Volume 22 Issue 11 Pages 2642-2649
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of N-(p-(2-benzimidazolyl) phenyl) maleimide (BIPM) (1) with egg albumin was examined and detailed chemical and spectroscopic analyses of the modified protein were performed. BIPM reacted specifically with thiol groups in egg albumin to give fluorescent adducts in agreement with the empirical rule previously proposed by the authors. The incorporated BIPM exists as a succinamic acid form 3 in the protein. These results are of significance in the use of BIPM as a fluorescent thiol reagent for proteins.View full abstractDownload PDF (857K) -
FUMIKO ABE, SHOJI YAHARA, KIMIKO KUBO, GENICHIRO NONAKA, HIKARU OKABE, ...1974 Volume 22 Issue 11 Pages 2650-2655
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stem bark of Xanthoxylum piperitum DC. was phytochemically examined and five new lignans, viz., xanthoxylol (3), piperitol (5), their γ, γ-dimethylallyl ethers (6, 7) and sanshodiol (8) were isolated besides l-asarinin (1) and l-sesamin (2) and their structures were determined. Phytosterol, γ-fagarine, skimmianine, syringaldehyde, piperonylic acid, menisperine, laurifoline and magnoflorine were also isolated from the same source.View full abstractDownload PDF (832K) -
TOSHIO NAMBARA, SHIGEO IKEGAWA, TSUYAKO ISHIZUKA, JUNICHI GOTO1974 Volume 22 Issue 11 Pages 2656-2661
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to clarify the stereochemistry of hydrogen loss from C-2 and C-4 during microbial transformation of cholesterol into androsta-1, 4-diene-3, 17-dione, the stereospecific syntheses of epimeric 2- and 4-deuteriocholesterols (XIII, XVI, XIX, XXI) have been undertaken. The key intermediates leading to the required substrates, Δ2- and Δ3-5α-cholesten-5-ols (II, VIII), were prepared from cholesterol in several steps. These olefins were converted to the 2α- and 4α-deuterio-3α, 5α-diols (XI, XVII) by treatment with deuteriodiborane. On the other hand trans-diaxial opening of the α-epoxides (III, Vb) with lithium aluminum deuteride provided the 2β-and 4β-deuterio-3, 5α-diols (XIV, XX). Upon dehydration with thionyl chloride and pyridine these labeled products were led to the desired compounds.View full abstractDownload PDF (843K) -
ISAO KITAGAWA, YASUSHI YAMAZOE, HIROTAKA SHIBUYA, REIJI TAKEDA, HIDEKA ...1974 Volume 22 Issue 11 Pages 2662-2674
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a continuation of our study on the biogenetically patterned transformation leading to the natural terpenoids, conversion of an eudesmanolide directing to the related eremophilanolide was investigated and the object was accomplished. After several attempts, treatment of 5α, 6α-epoxy-dihydroalantolactone (15) with HCOOH-acetone (1 : 2) at reflux was found to afford eight products (A-H). Among them, two major products (products A and B) and one minor product (product D), which were obtained in a combined yield of 46%, were elucidated to be the desired eremophilanolides (17, 18, and 23) on the basis of the physicochemical evidence and the chemical conversion of 23 to tetrahydroligularenolide (34). The structure of the product C was assigned 20 on the basis of its physical properties and the chemical derivation. Afterwards, a better reaction condition transforming 15 to give 17 and 18 in a combined 68% yield was found.View full abstractDownload PDF (1408K) -
MAKOTO FUJII, YOSHIYASU TERAO, MINORU SEKIYA1974 Volume 22 Issue 11 Pages 2675-2679
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present paper discloses a decarboxylation reaction of several conjugated unsaturated ketones and nitriles with carboxylic acids such as acetoacetic acid, malonic acid and cyanoacetic acid. In the reaction these carboxylic acids are decarboxylated and introduced at β-carbon of the conjugated unsaturated compounds. Thus there have been provided a effective means of introducing acetonyl, carboxymethyl and cyanomethyl at that position.View full abstractDownload PDF (667K) -
ATSUO NAGAMATSU, TOSHIKO HAYASHIDA1974 Volume 22 Issue 11 Pages 2680-2684
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe syntheses of L-leucyl-L-lysine amide, glycyl-L-lysyl-L-lysine, glycyl-L-lysyl-L-lysine amide, glycyl-L-lysyl-L-arginine and L-lysyl-L-lysyl-L-arginine were described. All dipeptides and dipeptide amides examined were resistant to plasmin, while glycyl-L-lysine amide and L-leucyl-L-lysine amide were cleaved by trypsin although dipeptides were not. Tetrapeptide, glycyl-L-lysyl-L-lysyl-L-arginine, was hydrolyzed by plasmin to glycyl-L-lysine and L-lysyl-L-arginine, as well as by trypsin. L-Lysyl-L-lysyl-L-arginine was cleaved on lysyllysine bond by plasmin, however, no reaction occurred by trypsin. The other hand, L-lysyl-L-lysyl-L-lysine was hydrolyzed by trypsin to L-lysyl-L-lysine and L-lysine, although this tripeptide was not attacked by plasmin. Also glycyl-L-lysyl-L-lysine amide was not to be the substrate for plasmin, while this amide was attacked by trypsin, yielding glycyl-L-lysine and L-lysine amide in addition, to glycyl-L-lysyl-L-lysine, ammonia and L-lysine.View full abstractDownload PDF (652K) -
KOZO ISHIDATE, MICHINAO MIZUGAKI, MITSURU UCHIYAMA1974 Volume 22 Issue 11 Pages 2685-2691
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo fractions containing NADPH-enoyl CoA reductase activities were isolated from crude extracts of Candida albicans. One fraction (Type-I) having larger molecular weight utilizes 5-hydroxyundec-cis-2-enoyl CoA, oct-cis-2-enoyl CoA and oct-trans-2-enoyl CoA as substrates with Km values of 2.5×10-6M, 1.1×10-6M and 5.0×10-7M, respectively, while another fraction (Type-II) having smaller molecular weight utilizes these substrates with Km values of 3.0×10-6M, 5.3×10-5M and 1.0×10-5M, respectively. This indicates that there exist comparable differences between these two in their affinities especially for the latter two substrates. Some characterizations, such as, effects of pH and of heat treatment on the activities of these reductase preparations were also investigated.View full abstractDownload PDF (772K) -
YOSHIHIRO NISHIKAWA, KAZUHIRO OHKI, KATSUO TAKAHASHI, GOICHI KURONO, F ...1974 Volume 22 Issue 11 Pages 2692-2702
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom six species of lichens, a variety of polysaccharide fractions were prepared and their antitumor effects were tested against the sarcoma 180 implanted in mice. These fractions were characterized by chemical and physicochemical methods. The active principle of Lasallia pensylvanica has been determined as GE-3 type glucan (a partially O-acetylated β-(1→6)-glucan). Another highly effective β-glucan, containing (1→3)-and (1→4)-linkages in the ratio 3 : 7, was isolated from Usnea rubescens, and it has been identified with lichenin. In addition, presence of so far unknown heteropolysaccharides with moderate antitumor effect has been suggested in the minor fraction of the lichen. Four Cladonia lichens, i.e.C. crispata, C. mitis, C. rangiferina subsp. grisea, and C. squamosa, were also examined, and it has been revealed that, in all of them, complex heteroglycans consisting chiefly of mannose, galactose, and glucose occur commonly as predominant, cold-water soluble polysaccharides, together with a small amount of α-glucan presumed to be PC-3 type (an α-glucan possessing (1→3)- and (1→4)-linkages alternately). Both the heteroglycan fraction and the glucan fraction of C. squamosa were shown to exert moderate antitumor effect.View full abstractDownload PDF (1241K) -
SEIKI TANADA, KEITO BOKI1974 Volume 22 Issue 11 Pages 2703-2709
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe adsorption of hydrogen sulfide gas on the thirty kinds of adsorbents (ten kinds of silicates, ten kinds of active carbons, and ten kinds of zeolites) was measured gravimetrically using Brunauer, Emmett, Teller (BET) apparatus with spring balance at 30°and 50 mmHg in order to find out the most suitable adsorbent for the hydrogen sulfide gas removal by a dry process. Among the thirty adsorbents, No. 23 (synthetic zeolite F-9) showed the largest amount of adsorption (mg/g). The relations between the amount of H2S adsorbed per unit surface area (mg/m2) and surface properties, the porous structure were investigated through surface pH, acid strength, acidity, basicity, adsorption isotherms, and pore size distribution. The adsorption of hydrogen sulfide gas (mg/m2) on the adsorbents except the active carbons was mainly determined by the porous structure of the adsorbents.View full abstractDownload PDF (703K) -
MASASHI TOMODA, SATOMI NAKATSUKA, NORIKO SATOH1974 Volume 22 Issue 11 Pages 2710-2713
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBletilla-glucomannan, the mucous polysaccharide isolated from Bletilla striata REICHENBACH fil., was found to contain 4.2% of O-acetyl group. The O-acetyl groups were located in position 3 of most of the glucose units. Methylation study provided the evidences that the polysaccharide is mainly composed of β-1→4 linked aldohexopyranose residues having a branched structure with 1→2 branch point at a part of mannose units, and mannose units occupy non-reducing terminal positions in the molecule.View full abstractDownload PDF (597K) -
TAKASHI UESUGI, MARIKO IKEDA, RYOHEI HORI, KOUICHI KATAYAMA, TAKAICHI ...1974 Volume 22 Issue 11 Pages 2714-2722
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the administration of thiamphenicol (TP), the metabolites found in the urine and bile of rat, guinea pig and rabbit, and in the urine of human were unchanged TP, a hydrolysis product of TP, and a conjugate of TP with glucuronic acid. TP glucuronide was isolated from the guinea pig urine and bile, and identified. The urinary and/or biliary excretion of TP metabolites in rat, guinea pig, rabbit and human was also studied by comparison with chloramphenicol (CP). The major route of the excretion of TP in human, rabbit and rat was by way of the kidneys, and the most of the drug was excreted in the unchanged form. In guinea pig, TP was excreted mainly into the bile and the most of the drug excreted was a glucuronide. On the other hand, CP was extensively conjugated and metabolized in all the animals used. In human, rabbit and guinea pig the major route of the excretion of CP was by way of the kidneys, and in rat by way of the bile and the excreted form was mostly a glucuronide.View full abstractDownload PDF (1040K) -
TAKAHARU MIZUTANI, AKIRA MIZUTANI1974 Volume 22 Issue 11 Pages 2723-2725
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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TOMOHIDE TANAKA, HIROSHI NAKAMURA, ZENZO TAMURA1974 Volume 22 Issue 11 Pages 2725-2728
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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TOHRU HINO, MAMORU ENDO, MASAKO NAKAGAWA1974 Volume 22 Issue 11 Pages 2728-2731
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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MASATO SHINODA, YOSHINARI TAKAGI1974 Volume 22 Issue 11 Pages 2732-2734
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (427K) -
TOSHIO KINOSHITA, FUMIO IINUMA, AKIO TSUJI1974 Volume 22 Issue 11 Pages 2735-2738
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (548K) -
KAZUKO OHGI, TAKEKO NISHIMURA, MASACHIKA IRIE1974 Volume 22 Issue 11 Pages 2739-2743
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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YOSHIO UENO, NORIKO SHIMADA1974 Volume 22 Issue 11 Pages 2744-2746
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (441K) -
MITSUGI KOZAWA, KIMIYE BABA, MASAFUMI MINAMI, HARUMI NITTA, KIYOSHI HA ...1974 Volume 22 Issue 11 Pages 2746-2749
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (598K) -
MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, SOJI SUGAI1974 Volume 22 Issue 11 Pages 2752-2754
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (422K) -
MIKIO HORI, TADASHI KATAOKA, HIROSHI SHIMIZU, HEIJI HORI, SOJI SUGAI1974 Volume 22 Issue 11 Pages 2754-2757
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (503K) -
KEN-ICHI HIRAO, OSAMU SETOYAMA, TAKAKO SAITO, OSAMU YONEMITSU1974 Volume 22 Issue 11 Pages 2757-2758
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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TAKAO MURAKAMI, NOBUTOSHI TANAKA, KATSUMI TANAKA, CHIUMING CHEN1974 Volume 22 Issue 11 Pages 2758-2761
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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MASANORI KUROYANAGI, MASAMICHI FUKUOKA, KUNITOSHI YOSHIHIRA, SHINSAKU ...1974 Volume 22 Issue 11 Pages 2762-2764
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (475K) -
MIWAKO MATSUO, HIROYOSHI AWAYA, CHIKATOSHI MASEDA, YOSHINORI TOMINAGA, ...1974 Volume 22 Issue 11 Pages 2765-2766
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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EIICHI YOSHII, YOSHIKO KOBAYASHI, TORU KOIZUMI, TAKIKO ORIBE1974 Volume 22 Issue 11 Pages 2767-2769
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
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TOSHIO KINOSHITA, FUMIO IINUMA, AKIO TSUJI1974 Volume 22 Issue 11 Pages 2769-2770
Published: November 25, 1974
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (361K)
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