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YUKIO MORI, KAZUMI TOYOSHI, SHIGEO BABA, YASUJI KASUYA
1976 Volume 24 Issue 10 Pages
2279-2285
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The metabolic pattern of 3'-methyl-4-dimethylaminoazobenzene (3'-Me-DAB) in the rat liver through the course of hepatic carcinogenesis by 3'-Me-DAB and the relationship between the hepatic activity for 3'-Me-DAB metabolism and species difference observed in the carcinogenic activity of the dye were investigated. The hepatic activity for 3'-Me-DAB metabolism with the liver of rats, mice, and hamsters fed a diet containing 3'-Me-DAB was measured by the tracer technique. By the repeated administration of 3'-Me-DAB, the hepatic azo-reduction activity of hamsters was depressed but their N-demethylation activity was conversely promoted throughout the observation period. Consequently, the total conversion of 3'-Me-DAB to metabolites in the liver of hamsters fed the dye remained almost the same as that of the control. In the rat liver, the most sensitive organ for carcinogenesis, 3'-Me-DAB administration had a marked effect on 3'-Me-DAB-metabolizing activity, and the azo-reduction activity was significantly depressed by the feeding of 3'-Me-DAB diet already from 6 hr later throughout the experimental period. In contrast, the N-demethylation reaction of 3'-Me-DAB to 3'-methyl-4-methylaminoazobenzene, a proximate carcinogen, was enhanced in the rat and mouse liver by their treatment only at the early period when the formation of protein-bound dye in the liver rose to a maximum peak by 3'-Me-DAB administration. In the rat hepatic tumors formed by the administration of 3'-Me-DAB for 3-4 months, all the activities for 3'-Me-DAB metabolism were notably decreased. Thus, it was found that the hepatic activities for 3'-Me-DAB metabolism were specifically affected by 3'-Me-DAB administration in all the three species, in which 3'-Me-DAB is carcinogenic or not.
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MAMORU SUGIURA, MUTSUKO SUZUKI, MASAO ISHIKAWA, MASANORI SASAKI
1976 Volume 24 Issue 10 Pages
2286-2293
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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To utilize aminopeptidase from Aspergillus japonica as a digestive enzyme preparation, the properties of the crude enzyme were examined from pharmaceutical aspects. The enzyme was most active at pH 8.0 and 50°, and was stable in a pH range of 5.5 to 8.5 and below 50°. The enzyme was activated by Co
2+, but was strongly inhibited by some metal ions, ophenanthroline, and N-bromosuccinimide. Hydrolytic cross-reaction between the enzyme and various proteases was carried out using casein as a substrate. The hydrolysis ratio (60%) was 2-fold greater than that by only the individual proteases. Therefore, the enzyme is considered to be useful for digesting a protein, together with other proteases. From the examination of the stability of the enzyme powder and that of the enzyme to various pharmaceutical factors, the enzyme was found to be highly stable to diluents, binders, and wetting agents at a high concentration, and was also stable to low first pressure in tabletting. From these results, it is suggested that this aminopeptidase can be satisfactorily utilized as a digestive enzyme preparation.
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HIROAKI TSUKATANI, SADAJI YAMADA, AKIRA TOKUMURA, TSUMORU MIYAMOTO, KE ...
1976 Volume 24 Issue 10 Pages
2294-2300
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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A depressor substance was found in acetone extract of bovine brain, greatly purified with the use of various chromatographic techniques, and tentatively named as D-I. It caused a sharp fall in arterial blood pressure of anesthetized cats with intravenous injections of 10 μg level of purified sample per kg animal body weight on a weight basis. Its hypotensive activity was not affected by previous treatment of cats with atropine, diphenhydramine, or hexamethonium. In the enzymic assay with the use of prostaglandin dehydrogenase (PGDH), neither prostaglandin E (PGE) nor prostaglandin F (PGF) compound was found. In the test of an incubation with a proteinase (nagase), the depressor activity was recovered almost completely. This depressor substance is definitely distinguishable from other depressor compounds and relatively resemble to lysolecithin, in the comparison of its attitude on TLC or in the course of purification process.
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MICHIYA KIMURA, AKIHARU FUJINO, KATSUHIKO YAMAZAKI, TAKUJI SAWAYA
1976 Volume 24 Issue 10 Pages
2301-2304
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Reactions with the simple aerobic hydroxylating system at moderate temperature were studied on the aqueous solutions of two varieties of bile acid. Ferrous sulfate was added to a buffered solution (pH 6.5-6.7) of nordeoxycholic acid which was bubbled with molecular oxygen, as reported. The structures of the methylated products were elucidated as methyl 24-nor-3α, 12α, 15α-trihydroxy-5β-cholan-23-oate and methyl 24-nor-3α, 12α-dihydroxy-15-oxo-5β, 14β-cholan-23-oate. Oxygen function was introduced also stereospecifically at C
15 and in an α-configuration when taurodeoxycholic acid was treated with the same hydroxylating system.
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TADAHIRO SAWAYAMA, HIROAKI KINUGASA, HARUKI NISHIMURA
1976 Volume 24 Issue 10 Pages
2305-2311
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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It was proved that an alkaline-hydrolysis product of isatylidene-3-rhodanine (I) was not 1, 2-dihydro-3-mercapto-2-oxocinchoninic acid (III) reported by Granacher, but isatylidene-3-mercaptoacetic acid (II). On the basis of this assignment, some structures of its derivatives incorrectly reported were revised. Moreover, the configurations of II and its derivatives are discussed.
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MIKIO TAKEDA, GORO TSUKAMOTO, KATSUYUKI NOGUCHI, SEIICHI SAITO, SEIICH ...
1976 Volume 24 Issue 10 Pages
2312-2316
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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As part of studies on the structure-activity relationships of azabicycloalkane antagonistanalgetics, the title compound (II), a five membered alicyclic analog of I (a good mixture of analgetic and antagonist properties), was synthesized. The phenols (XII and XIII) with a bridged 3-phenylpyrrolidine moiety similar to that of I were found to be analgetically inactive. Thus, a shape of the alicyclic ring may also play an important role on the analgetic effectiveness of these derivatives. Interestingly, however, XII and XIII displayed apparent properties of narcotic antagonism on the order of I and pentazocine, the result suggesting that the structural requisite for the antagonist activity in these derivatives, differing from those for analgesia, may be a N-methylphenylethanamine chain.
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CHIKAKO TAKAHASHI, SETSUKO SEKITA, KUNITOSHI YOSHIHIRA, SHINSAKU NATOR ...
1976 Volume 24 Issue 10 Pages
2317-2321
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The structure of the compound B (xanthoascin) was proved to be 1-(4-hydroxyphenyl)-4-(2, 2-dimethyl-6-chromanyl)-2, 3-diisocyano-1, 3-butadiene (3) by chemical and physical methods.
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KAZUO NITTA, HIROSHI OGAWA, TAKAYUKI ITO, MASAHARU KOJIMA, MINORU MAED ...
1976 Volume 24 Issue 10 Pages
2322-2326
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Distribution studies in male Wistar rats of pure 19-iodocholesterol-
131I (CL-19-
131I) and 6β-iodomethyl-19-norcholest-5-(10)-en-3β-ol-
131I (NCL-6-
131l) were performed. The uptake of NCL-6-
131I in the rat adrenal gland was ten times greater than that of CL-19-
131I. The ratios for adrenal-to-liver in the concentration of NCL-6-
131I were always higher than those of CL-19-
131I. Therefore, NCL-6-
131I seems to be a better adrenal-scanning agent than CL-19-
131I.
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HIDEYO SHINDO, EIICHI NAKAJIMA, EIJI SHIGEHARA
1976 Volume 24 Issue 10 Pages
2327-2334
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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A technique which was designated as"whole-body adsorption autoradiography"was applied to find binding characteristics of bis- and mono-quaternary ammonium ions by rat various tissues. Rat freeze-dried whole-body sections were incubated in an aqueous solution of
14C-labeled deca-, hexa- and dimethonium and tetraethyl- and cetyltrimethylammonium. After rinsing and being freeze-dried, the adsorption of radioactivity was detected by autoradiography. It was found that bisonium ions are highly adsorbed in the cartilage tissues of vertebra, sternum and trachea, wherein a similar high accumulation occurs in vivo, and appreciably adsorbed in the thymus, salivary gland and bone marrow. These adsorptions were interpreted as being due to an ionic bonding of the bis-quaternary ammonium cations to the sulfate and phosphate anions of the chondroitin sulfate and cellular desoxyribonucleic acid (DNA), respectively, probably by forming a bridged structure, with an aid of Alcian Blue staining of the rat whole-body sections (whole-body histochemistry). Close relations between the in vitro adsorption characteristics and the in vivo distribution patterns are pointed out and discussed. It was thus concluded that a physico-chemical binding of a drug molecule to the tissue macromolecules plays an important role in determining the in vivo distribution pattern in animal body and that a combined use of this method with conventional wholebody autoradiography provides a useful tool in establishing the drug distribution characteristics and their interpretation.
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FAKHRELDINS. GHAZY, TOSHIKIRO KIMURA, SHOZO MURANISHI, HITOSHI SEZAKI
1976 Volume 24 Issue 10 Pages
2335-2339
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Studies of the influence of riboflavine (RF) and flavine mononucleotide (FMN) photolysates on the intestinal membrane and its constituents have been pursued. The absorption experiments were carried out using in situ recirculation technique. It was found that the uptake of bromphenol blue (BPB) by the isolated intestinal epithelial cells was increased. Pretreatment experiments showed that, a period of 15 min was required for the hyperabsorptive state of the intestine to return back to its normal function. Histological studies of small intestinal mucosa could not demonstrate any detectable change. D-glucose absorption was not affected by the photolysates of riboflavine. NMR studies and liposome experiments revealed an interaction between the intermediate products of photolysis and egg phosphatidylcholine (PC). TLC and thiobarbituric acid test disclosed formation of lipid peroxides. A decrease in the surface tension was also occurred. From these data it was assumed that the intermediate products of photolyses attacked the double bonds of the unsaturated fatty acid side chain of PC molecules followed by cleavage and splitting of short chain fatty acids, consequently, change in permeability of the intestinal membrane due to disorganization of phospholipid moecules could be expected.
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TERUHISA HIRAYAMA, FUKUJIRO FUJIKAWA, ITIRO YOSIOKA, ISAO KITAGAWA
1976 Volume 24 Issue 10 Pages
2340-2344
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Following the thin-layer chromatographic examinations of the acetone extractive of two lichens : Manegazzia asahinae (YAS. ex ZAHLBR.) SANT. and M. terebrata (HOFFM.) Mass, which have been disclosed to contain the same kinds of metabolites, a new depsidone named menegazziaic acid (4) has been isolated from M. terebrata in addition to stictic acid (1), atranorin (2), constictic acid (3), and chloroatranorin (5) The structure of menegazziaic acid has been established as 4, in which the formyl function at C-3 of stictic acid (1) is replaced by a hydroxyl, on the basis of chemical and physicochemical evidence including the chemical conversion of menegazziaic acid to stictic acid (1).
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MASAHIRO NAKANO, AKIRA KUCHIKI, TAKAICHI ARITA
1976 Volume 24 Issue 10 Pages
2345-2349
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Permeabilities of acetaminophen, bucolome (5-n-butyl-1-cyclohexyl-2, 4, 6-trioxo-perhydropyrimidine), salicylic acid, aminopyrine, sulfamethizole, sulfisomidine, and p-aminobenzoic acid through a collagen membrane were measured at different pH values. The effect of pH of the media on permeation of acetaminophen, an unionizable drug in the pH range studied, was minor. Drugs in molecular form permeated faster than those in ionic form. Amphoteric drugs in cationic form permeated slower than those in corresponding anionic form. Little effect of charges of the drug molecules was observed on drug permeation through a cellophane membrane.
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RENJI AIKAWA, MASAHIRO NAKANO, TAKAICHI ARITA
1976 Volume 24 Issue 10 Pages
2350-2355
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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An intensively fluorescent product was formed in alkaline solution by hydrolysis of cephalexin at elevated temperature. The fluorescent product gave excitation and emission maxima at 355 and 435 nm, respectively. It was readily extracted into ethyl acetate and a acetone-chloroform mixture from an acidic solution and then extracted back into an alkaline solution. Using this new method, urinary excretion behaviors in human volunteers after oral administration of cephalexin capsule were investigated.
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KAZUHISA FUNAKOSHI, YOSHIYUKI KUCHINO, HIROMICHI SHIGYO, HIROTSUNE SON ...
1976 Volume 24 Issue 10 Pages
2356-2363
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Detailed examination of the reaction of quinoline 1-oxide (1) with methacrylonitrile in the presence of acetic anhydride and the re-examination of the reaction of 1 with acetic anhydride have revealed that there is another reaction sequence leading to polyquinolylmethanes, [tri-(2-quinolyl) methane (5), N-(2-quinolyl)-2-(2-quinolylmethylene)-1, 2-dihydroquinoline (11) and N-(2-quinolyl)-2-[di-(2-quinolyl) methylene]-1, 2-dihydroquinoline (6)], besides the formation of carbostyril in the latter reaction. Reactions of 1 with acetic anhydride in the presence of quinaldine, di-(2-quinolyl)-methane (9), cyanoacetic acid, malonic acid and phenylacetic acid were also examined in connection with the exploration of the mechanism of the above reaction, and the possible mechanism has been proposed.
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NORIKO MOTOHASHI, ITSUHIKO MORI, YUKIO SUGIURA
1976 Volume 24 Issue 10 Pages
2364-2368
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Concurrent redox and complexation reactions between copper (II) and ergothioneine (ESH) have been investigated by means of optical, electron spin resonance (ESR) and nuclear magnetic resonance (NMR) spectra. An equimolar mixture of Cu (II) with ESH gave rise to a green complex. This complex showed an asymmetric peak at 675 nm assigned to d-d transition of Cu (II). The ESR spin Hamiltonian parameters (g⫽=2.246, g⊥=2.068, and A⫽=158G) of the green complex were typical for the Cu (II) complex of sulfur coordination. In the presence of two molar or excess ESH to Cu (II), an yellow Cu (I) complex was formed. The result of
13C-NMR measurements supports that ESH also coordinates to Cu (I) ion through the thiolate sulfur in the yellow complex.
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HARUO KANAZAWA, SUSUMU ISHIMITSU, MASUMI SAKANE, KOJ KAWAMATA, RYOICHI ...
1976 Volume 24 Issue 10 Pages
2369-2372
Published: October 25, 1976
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1) The present research has been planned to clarify the importance of tryptophan residues in chymopapain A by means of N-Bromosuccinimide (NBS) oxidation. 2) About four tryptophan residues were oxidized and the first oxidizable tryptophan residue was important for enzyme activity. 3) The rate of oxidation by NBS increased with the decrease of pH. 4) SH group and histidine residues in chymopapain A were not affected by NBS. 5) These results indicate that the first oxidizable tryptophan residue is responsible for the loss of enzyme activity by NBS oxidation.
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YOSHIHISA KURASAWA, ATSUSHI TAKADA, TAKEO UEDA
1976 Volume 24 Issue 10 Pages
2373-2376
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The color reaction of cholesterol with trichloroacetic acid and hydrochloric acid (TCA-HCl) (1 : 1) was carried out in the presence of oxygen and/or hydrogen peroxide at a room temperature, and 3, 5-cholestadiene, 3, 3'-bis (3, 5-cholestadiene), cholesteryl chloride and cholesteryl trichloroacetate were isolated from the colored reaction mixture. From the observation of the absorption spectra, it was inferred that the absorption maximum at 560 or 563 nm should be ascribed to the carbocation formed by the protonation of 3, 3'-bis (3, 5-cholestadiene) in TCA-HCl (1 : 1). It was found that the dimerization was the main oxidative reaction in the present investigation, although it was suggested by many investigators that the formation of the monomeric cholestapolyenes should be the primary oxidation in the Liebermann-Burchard and the Zak reactions. From the result that the chlorinated steroids other than cholesteryl chloride were not acquired, it was assumed that cholesteryl chloride should be produced through the intermediate resulting from the dehydration of cholesterol in the acidic solution, and that 3, 3'-bis (3, 5-cholestadiene) also should be formed through this intermediate by an oxidative mechanism.
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SEIJI MITSUI, SHINSAKU KOBAYASHI, HITOSHI NAGAHORI, AKIRA OGISO
1976 Volume 24 Issue 10 Pages
2377-2382
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The potent anti-ulcer principles, 1'-acetoxychavicol acetate (1) and 1'-acetoxyeugenol acetate (2), were isolated from seeds of Alpinia galanga WILD., and established by chemical syntheses. Besides, three sesquiterpenes, caryophyllene oxide (10), caryophyllenol-I (11) and caryophyllenol-II (13), along with n-pentadecane, n-7-heptadecene and fatty acid methyl esters, were also isolated.
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HIROSHI KOBAYASHI, TSOCHIN PENG, MASASHI FUJIKAWA, SHOZO MURANISHI, HI ...
1976 Volume 24 Issue 10 Pages
2383-2390
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The mechanism of the inhibition caused by polysorbate 80 on the intramuscular absorption of water-soluble drugs was studied. It was found that the absorption pattern of isonicotinamide was different from that of polysorbate 80. The inhibition of the absorption requires the existence of polysorbate 80 at the site of injection. Histological studies showed that there is no correlation between the inhibition in absorption and the local effect of polysorbate 80 which was found to cause some inflammation at the site of injection. The influence of polysorbate 80 on the capillary permeability was investigated. This was done by intravenous pre-administration of polysorbate 80, sympatholytic agent or conjugated estrogen. No difference in the intramuscular absorption of the tested drugs in the presence or absence of polysorbate 80, whether the animals were pretreated or not, could be demonstrated. Therefore, the inhibition in the intramuscular absorption of these drugs could not be attributed to a direct nor indirect effect of polysorbate 80 on the capillary walls. It was suggested that the permeation of drug through the intercellular spaces of muscle fibers and connective tissues is the more dominant process.
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AKIRA MIZUTANI, AKIRA OKANO, YOSHIAKI ISOBE, TAKAHARU MIZUTANI, YOSHIH ...
1976 Volume 24 Issue 10 Pages
2391-2399
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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A hypocalcemic protein was isolated for the first time from porcine parotid gland by the procedures of aqueous extraction, precipitation at pH 4.8, ammonium sulfate fractionation, chromatography on DEAE-cellulose, and repeated gel filtration on Sephadex G-200. The purified protein lowered the serum-calcium concentration in albino rabbits by 12.5±1.3% at a dose of 20μg/kg body weight 4-6 hr after the injection. The purified protein was found to be homogeneous, being a single band by polyacrylamide gel electrophoresis and by analytical ultracentrifugation. The molecular weight of the porcine hypocalcemic protein was determined to be 52000 by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. Amino acid analysis revealed that the protein was rich in aspartic and glutamic acids and in leucine, and that the ratio of acidic/basic amino acid residues was 2.13, and the ratio of histidine/lysine was 3.07 in this protein. The latter ratio is characteristic, since the ratio is below 1.00 in many proteins. The chemical properties of the porcine parotid hypocalcemic protein were slightly different from that of the bovine parotid hypocalcemic protein, although they were similar in biological effect.
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MICHIKO IIJIMA, TOKUHIKO HIGASHI, SYUICHI SANADA, JUNZO SHOJI
1976 Volume 24 Issue 10 Pages
2400-2405
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The effect of ginsenosides purified from Ginseng (the roots of Panax ginseng C. A. MEYER) on nuclear ribonucleic acid (RNA) synthesis was investigated. Four hours after intraperitoneal injection of each of the ginsenosides (-Rb
1, -Rc, and -Rg
1) at a dose of 5 mg per 100 g body weight, incorporation of
3H-orotic acid into nuclear RNA of rat liver was determined. The ginsenosides showed different activities : Rb
1 increased and Rc decreased the incorporation, and Rg
1 did not affect it. Furthermore, the effect of ginsenoside-Rb
1 and -Rc on RNA polymerase activity was investigated 3 hr after the intraperitoneal administration. Rb
1 enhanced and Rc repressed the enzyme activity, the results being consistent with those on the incorporation study. Both purified ginsenosides did not show any effect on RNA polymerase activity when added in vitro.
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JUTARO OKADA, AKIRA FUJIMOTO, KOICHI NAKANO, NORIO MASAKI, HISAO IIZUK ...
1976 Volume 24 Issue 10 Pages
2406-2408
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Of several photoproducts of 1, 2-cyclohexanedione, the structure of the crystalline compound (IIb) with a molecular formula C
12H
18O
5 was established as perhydro-4a, 9a-epoxydibenzo-p-dioxin-5a, 10a-diol by means of an X-ray crystallographic analysis. In addition, the formation process of this compound was also discussed.
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OSAMU IWAMOTO, KUNIO SUZUKI, YOSHIYASU TERAO, MINORU SEKIYA
1976 Volume 24 Issue 10 Pages
2409-2412
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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It has been found that a decarboxylation reaction of propiolic acid proceeds with N-benzylideneaniline to give 2-phenylquinoline. Extention of this reaction furnishes generality for a convenient synthesis of 2-phenylquinoline derivatives. A plausible reaction path involving 3-anilino-3-phenyl-1-propyne intermediate is proposed.
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HIROYUKI KURODA, SHOZO NAKAZAWA, KEN KATAGIRI, OSAMU SHIRATORI, MUTSUO ...
1976 Volume 24 Issue 10 Pages
2413-2420
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Twenty-three kinds of bisbenzylisoquinoline alkaloids including tetrandrine, isotetrandrine, and berbamine were studied on various biological activities. We made comparisons in biological activities, for examples, on bacterial cells, blood cells, tumor cells, and in the whole mouse, in order to obtain better suggestion concerning the correlation between activity and chemical structure. From the results of the present investigation, it is suggested that at the present stage a definite structure-activity relationship, as reported by Kupchan, et al., is hardly delineated, though certain structure requirements for the manifestation of the antitumor activities were noticed.
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MITSUAKI WATANABE, MITSUKI BABA, TOSHIO KINOSHITA, SUNAO FURUKAWA
1976 Volume 24 Issue 10 Pages
2421-2427
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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HIROSHI OGAWA, MINORU KUBOTA, HARUAKI YAJIMA
1976 Volume 24 Issue 10 Pages
2428-2434
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The protected octadecapeptide corresponding to positions 26 through 43 of porcine gastric inhibitory polypeptide was synthesized by a conventional method. In this deprotected peptide, any significant inhibitory effect against the gastric acid secretion stimulated by histamine hydrochloride was not noted in heidenhein pouch dogs.
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MINORU KUBOTA, HIROSHI OGAWA, HARUAKI YAJIMA
1976 Volume 24 Issue 10 Pages
2435-2446
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The octacosapeptide amide corresponding to positions 1 through 28 of porcine gastric inhibitory polypeptide (GIP) was synthesized in a conventional manner. This peptide fragment of GIP exhibited no suppression of gastric acid secretion stimulated by tetragastrin in Heihenhein pouch dogs.
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HIROSHI OGAWA, MINORU KUBOTA, HARUAKI YAJIMA, TAKAYOSHI TOBE, MASAKI F ...
1976 Volume 24 Issue 10 Pages
2447-2456
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The tritetracontapeptide corresponding to the entire amino acid sequence of porcine gastric inhibitory polypeptide (GIP) was synthesized starting with the C-terminal octadecapeptide, the synthesis of which was previously reported. The hydrogen fluoride procedure was employed to remove all protecting groups employed at the final stage of the synthesis. Trichloroethyloxycarbonylhydrazine was used to prepare alternatively the nonacosapeptide, a cyanogen bromide fragment of GIP, H-(GIP 15-43)-OH. Synthetic GIP suppressed gastric acid secretion stimulated by histamine as well as tetragastrin in Heidenhein pouch dogs. H-(GIP 15-43)-OH exhibited approximately one quarter of the activity of the whole molecule. Association of the insulin release activity in GIP was synthetically confirmed.
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HIDEO SETO, KOJI HAYASHI, HIROSHI MITSUHASHI
1976 Volume 24 Issue 10 Pages
2457-2460
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The configuration at C-20 of tomentogenin and utendin was determined as s by means of the circular dichroism experiment of 20-O-o-nitrobenzoyl derivatives. From these results, the absolute configurations of tomentogenin and utendin were determined as 5α-pregnan-3β, 12β, 14β, 17β, 20α-pentol and pregn-5-ene-3β, 12β, 14β, 17β, 20α-pentol, respectively.
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TETSUO KATO, NORIICHI ODA, ISOO ITO
1976 Volume 24 Issue 10 Pages
2461-2469
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Attempts to prepare oxazolo [4, 5-d] pyrimidines by the reaction of 2, 4-diamino-5-hydroxy-6-methylpyrimidine (I) with aromatic carboxylates. The products were carbinolamines which were converted to oxazolo [4, 5-d] pyrimidines. Also, the application of the Salol reaction of I gave 5-amino-2-(2, 4-diamino-6-methylpyrimidin-5-yl)oxy-2-o-hydroxyphenyl-7-methyl-3H-oxazolo [4, 5-d] pyrimidine (XI) which was an unusual product in this reaction.
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ISAO KITAGAWA, YUJI IKENISHI, MASAYUKI YOSHIKAWA, ITIRO YOSIOKA
1976 Volume 24 Issue 10 Pages
2470-2479
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Sakuraso-saponin (3), a pentaglycoside of protoprimulagenin A (1), has been isolated from the root of Primula sieboldi E. MORREN (Primulaceae, Japanese name : sakuraso). Complete acid hydrolysis of sakuraso-saponin (3) furnished primulagenin A (2), glucose, galactose, rhamnose, and glucuronic acid, while the ultraviolet irradiation of sakuraso-saponin liberated the genuine aglycone protoprimulagenin A (1) in a good yield. On the bases of the chemical and physicochemical investigations of the prosapogenols : PS-1 (4), PS-2 (5), PS-3 (6), and PS-4 (7), and a pentaglycoside PS-5 (8), in addition to those of sakuraso-saponin (3), the full structure of sakuraso-saponin has been established as 3-O-{4-O-[α-L-rhamnopyranosyl (1→2)-α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→4)]-2-O-β-D-glucopyranosyl (1→2)-β-D-glucuronopyranosyl}-protoprimulagenin A (3), which is a first structure determination of the primulaceous saponins.
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YOSUKE SAWADA, HIROSHI SAKAMOTO, TETSUZO KUBO, HYOZO TANIYAMA
1976 Volume 24 Issue 10 Pages
2480-2485
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The production of the antibiotic, racemomycin-A, was found to be inhibited in the presence of glucose in the medium, although glucose was the best carbon source for Streptomyces lavendulae ISP 5069. The repression by 1% glucose was gradually restorde by the addition of Pharmamedia or amino acid mixture. A severe repression by glucose was also observed at the rapid phase of antibiotic production. On the repression, racemomycin-A produced was incorporated into the mycelium. Xylose and mannitol were weakly repressed on racemomycin-A formation, and maltose caused a mild stimulation of the formation. The production of streptothricin antibiotics in all organisms tested was inhibited by glucose.
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TOSHIO NAMBARA, SHIGEO IKEGAWA, HIDEKI ISHIDA
1976 Volume 24 Issue 10 Pages
2486-2493
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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In order to clarify the stereochemistry at C-4 in enzymatic saturation of Δ
4-3-ketoste-roids synthesis of 4-deuterated testosterone and androst-4-ene-3, 17-dione (XVIII, XIX) has been undertaken. The key intermediate leading to the required substrate, 4α-d
1-5α-androstane-3β, 4β, 17β-triol 3, 17-bis (dimethyl-tert-butylsilyl) ether (XVI), was prepared by stereospecific reduction with lithium aluminum deuteride from 3β, 17β-dihydroxy-5α-androstan-4-one disilyl ether (XIII), which was readily obtainable from androst-4-ene-3β, 17β-diol disilyl ether (XI) by hydroboration, followed by oxidation with chromium trioxide-pyridine complex. Dehydration of XVI with phosphorus oxychloride in pyridine provided the Δ
4 olefine (XVIIb) which on chromium trioxide oxidation was led to the desired compounds. Reductive dehalogenation of 4-bromotestosterone silyl ether (II) with lithium aluminum deuteride and subsequent oxidation with chromium trioxide-pyridine complex afforded 4-d
1-testosterone silyl ether (VII) in which the deuterium incorporation, however, proved to be unsatisfactory.
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OSAMU MATSUDA, MINORU SEKIYA
1976 Volume 24 Issue 10 Pages
2494-2499
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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We have now found that reactions of N-dialkylaminomethyl-dialkylamines and -imide, and O-dialkylaminomethyl ethers with N-(1-cyclohexen-1-yl) dialkylamines result in electrophilic substitution at α and α'positions of the enamine to give N-(2-dialkylaminomethyl-6-methylene-1-cyclohexen-1-yl) dialkylamines. Features and generalization of the reactions are described.
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TETSUJI KAMETANI, YOSHIRO HIRAI, KEIICHIRO FUKUMOTO
1976 Volume 24 Issue 10 Pages
2500-2503
Published: October 25, 1976
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Birch reduction of 16-carboxy-15, 16, 17, 18, 19, 20-hexadehydro-17-methoxyyohimbane (XII), followed by esterification with diazomethane, gave 15, 17, 18, 20-tetradehydro-17-meth-oxy-16-methoxycarbonylyohimbane (XIII), which was converted into 15, 16-dehydroyohimbinone (II). This was correlated with yohimbine (IV) by the present authors.
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KENICHI INUI, MACHIKO SHINTOMI, RYOHEI HORI, HITOSHI SEZAKI
1976 Volume 24 Issue 10 Pages
2504-2508
Published: October 25, 1976
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The effects of long-chain fatty acids solubilized by sodium taurocholate on the absorption of various water-soluble drugs from the rat small intestine were investigated using the in situ perfusion technique. The addition of 20 mM sodium taurocholate alone or together with lower concentration of oleic acid increased the absorption of poorly absorbable procaine amide, while with higher concentration of oleic acid decreased the absorption of the drug. The addition of oleic acid and monolein significantly increased the formation of micellar complex of well absorbable 2-allyloxy-4-chloro-N-(2-diethylaminoethyl) benzamide hydrochloride (A. C. D. B.) and inhibited the absorption of it, compared to those produced by 20 mM sodium taurocholate alone. The results suggested that the effects of long-chain fatty acids on the intestinal absorption of drugs in the presence of sodium taurocholate were mediated via two mechanisms : modification of the permeability of the membrane and micellar complexation of the drug.
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SEITARO SAEKI, AYAKO YAMASHITA, YASUHIRO MORINAKA, MASATOMO HAMANA
1976 Volume 24 Issue 10 Pages
2509-2516
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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In order to introduce 2-pyridyl group into the 9 position of 1, 1-disubstituted quinolizidine, N-benzoyloxypyridinium chloride (1) was treated with 9-dehydro-1-oxoquinolizidine (3), dehydro-1-ethoxycarbonyl-1-hydroxyquinolizidine (13) and 9-dehydro-1, 1-ethylenedioxyquinolizidine (16) in dichloromethane, followed by reduction of the reactants with sodium borohydride in anhyd. ethanol. Although reactions with 3 and 13 gave no satisfactory result, that with 16 afforded the expected 1, 1-ethylenedioxy-9-(2-pyridyl)-quinolizidine (18) in 17% yield together with dehydro-1, 1-ethylenedioxy-x-(2-pyridyl)-quinolizidine (19). Other observations encountered in reactions of 1 with 3 or 13 as well as in transformation of 2 into 13 and 16 were also described in some detail.
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NORIYOSHI INUKAI, HIDENORI IWAMOTO, NORIAKI NAGANO, ISAO YANAGISAWA, T ...
1976 Volume 24 Issue 10 Pages
2517-2520
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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4-Alkoxymethyl-5-chloro-5-cyano-2-norbornene (III) was produced by the Diels-Alder reaction using 5-alkoxymethyl-cyclopentadiene and α-chloroacrylonitrile in the presence of aqueous cupric boronfluoride. III was hydrolyzed to 4-alkoxymethyl-2-norbornen-5-one (V). When V was oxidized with m-chloroperbenzoic acid, the products were varied by differences of the reaction conditions. (3β-Methoxymethyl-3α-hydroxy-4-cyclopenten-1α-yl)-acetic acid lactone (IXa) was produced by the oxidation of 4-meth-oxymethyl-2-norbornen-5-one (Va) with m-chloroperbenzoic acid in the presence of aqueous sodium bicarbonate. IXa which was very unstable was easily rearranged to 5-meth-oxymethyl-3, 3aβ, 4, 6aβ-tetrahydro-2H-cyclopenta [b] furan-2-one (Xa).
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YOSHITAKA ITATANI, SHINGO YASUDA, MIYOJI HANAOKA, YOSHIO ARATA
1976 Volume 24 Issue 10 Pages
2521-2524
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The
13C nuclear magnetic resonance (
13C-NMR) spectra of the piperidine-type Nuphar alkaloids and their derivatives (I-V) were recorded with complete assignments. Two methyl groups of C-10 and C-11 in I and II were shown to be magnetically nonequivalent. The
13C-NMR spectroscopy was demonstrated to be more useful than
1H-NMR spectroscopy in studies on magnetic nonequivalence of dimethyl groups associated with molecular asymmetry. The shift values for some carbons caused by the introduction of the double bond, the hydroxyl group, and the acetyl group were examined.
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TETSUJI KAMETANI, CHISAE OHTSUKA, HIDEO NEMOTO, KEIICHIRO FUKUMOTO
1976 Volume 24 Issue 10 Pages
2525-2531
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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A new synthetic method for the tetrahydro-8-methylprotoberberines, coralydine (VIb) and O-methylcorytenchirine (VIa), was described. 3, 4-Dimethoxyacetophenone (IX) was converted into 4, 5-dimethoxy-2-methylbenzocyclobutene-1-carboxylic acid (XVII) by our method, which was condensed with homoveratrylamine to give N-(3, 4-dimethoxy-phenethyl)-4, 5-dimethoxy-2-methylbenzocyclobutene-1-carboxamide (XVIII). Thermolysis of the resulting 3, 4-dihydroisoquinoline hydrochloride (XXIII), which was obtained by Bischler-Napieralski reaction of XVIII, in bromobenzene followed by sodium borohydride reduction gave VIa and VIb.
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MASANORI SAKAMOTO, KYOKO MIYAZAWA, YOSHIO TOMIMATSU
1976 Volume 24 Issue 10 Pages
2532-2540
Published: October 25, 1976
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Reaction of diphenylketene (I) with azadienes (II-IX), having -C=N-C=N- multiple bond system between carbon-nitrogen double bond in heterocycles and their side-chain carbon-nitrogen double bond, gave the 1, 4-cycloadducts (XI-XVIII), respectively. Hydrogenolysis of the 1, 4-cycloadducts (XIb, XIIb, and XVIb), with lithium aluminum hydride in tetrahydrofuran gave the 1-propanol derivatives (XIX, XXI, and XXII), respectively. On the other hand, reaction of I with 3-(p-anisylideneamino)-5-phenylisoxazole (Xb) and 2-benzylideneaminopyridine (XXIV) respectively afforded 1-[3-(5-phenylisoxazolyl)]-3, 3-diphenyl-4-(p-anisyl)-2-azetidinone (XXIII) and 1-(2-pyridyl)-3, 3, 4-triphenyl-2-azetidinone (XXV).
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REIMEI MOROI, KEIICHI TOMITA, MITSUJI SANO
1976 Volume 24 Issue 10 Pages
2541-2548
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The structure of DJ-1461 in solution was determined by using lanthanide shift reagents. The position of the lanthanide ion and the protons of DJ-1461 in the complex were determined using the McConnell-Robertson equation. The shifts induced by lanthanide shift reagents agreed well with the calculated values, on the assumption that their origin is of pseudocontact nature. The europium ion-N
2 bond length was as long as 3.2 Å (phthalazine N
2 is set at the origin of the right handed polar co-ordinates system). It was found that the side chain of the DJ-1461 has an anti form towards the C=N bond, and the two double bonds S-cis configuration.
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TETSUZO KATO, TAKUO CHIBA, MOHSEN DANESHTALAB
1976 Volume 24 Issue 10 Pages
2549-2552
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Reaction of diketene with 5-phenyltetrazole (I) gave rise to 2-acetonyl-5-phenyl-1, 3, 4-oxadiazole (VII), and 3-(5-phenyl-1, 3, 4-oxadiazol-2-yl)-2, 6-dimethyl-4-pyrone (VIII). On the other hand, when this reaction was carried out in acetic acid with reflux, 2-methyl-5-phenyl-1, 3, 4-oxadiazole (IX) and 1, 1-diacetyl-2-benzoylhydrazine (X) were obtained. Reaction of diketene with 5-aminotetrazole (III) resulted in the formation of 7-methyltetrazolo [1, 5-a] pyrimidin-5 (8H)-one (XI).
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SHIGERU KOBAYASHI, HIDEKI ISHIKAWA, MASARU KIHARA, TETSURO SHING, SHOJ ...
1976 Volume 24 Issue 10 Pages
2553-2555
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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The bulbs of Crinum asiaticum L. var. japonicum BAKER (Amaryllidaceae) were found to contain N-demethylgalanthamine (II) as well as lycorine (III) and crinamine (IV). This is the first time that II has been isolated directly, as an single base, from a member of the Amaryllidaceae.
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SUSUMU ISHIMITSU, SADAKI FUJIMOTO, AKIRA OHARA
1976 Volume 24 Issue 10 Pages
2556-2558
Published: October 25, 1976
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A method for separatory determination of the isomers of hydroxyphenylalanine by liquid chromatography was established. The chromatographic conditions were as follows : Column, glass column (0.9×50cm) packed with Hitachi #2612 ion-exchange resin ; mobile phase, 0.2M citrate buffer (pH 2.80) and 0.2M citrate buffer (pH 3.90) ; flow rate, 1.0 ml/min ; temperature change from 30°to 55°at 3.25 hr ; buffer change at 1.5 hr ; detector, ultraviolet and visible detector.
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KANAME KOYAMA, HIDEHIKO WATANABE, HIROKI KAWATANI, JUN IWAI, HARUAKI Y ...
1976 Volume 24 Issue 10 Pages
2558-2563
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Succeeding to the syntheses of porcine and bovine corticotropin (ACTHs), human ACTH was alternatively synthesized by the conventional method. The synthetic peptide exhibited the in vivo steroidogenetic activity of 153.1 IU/mg.
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TETSUJI KAMETANI, KAZUO KIGASAWA, MINEHARU HIIRAGI, NAGATOSHI WAGATSUM ...
1976 Volume 24 Issue 10 Pages
2563-2566
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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Optical resolution of (+)-N-cyclopropylmethyl-3-hydroxy-9-azamorphinan (I) was successfully effected with (+)-O, O-dibenzoyltartaric acid or (2R : 3R)-2'-nitrotartranilic acid as the resolution agent. The optically active compounds thus obtained were tested for their analgesic activity and antagonistic effect of morphine analgesia.
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NORIYOSHI INUKAI, HIDENORI IWAMOTO, ISAO YANAGISAWA, NORIAKI NAGANO, T ...
1976 Volume 24 Issue 10 Pages
2566-2567
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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d-(2β-Benzyloxymethyl-3α-hydroxy-4-cyclopenten-1α-yl) acetic acid (d-II) which was a very important key intermediate for the synthesis of prostaglandins by a Corey's method was obtained by resolution of dl-II using L-arginine in a mixture of water and acetone.
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YASUMITSU TAMURA, HIRONORI HAYASHI, MASAZUMI IKEDA
1976 Volume 24 Issue 10 Pages
2568-2571
Published: October 25, 1976
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Reaction of 4-amino-1-methyl-1H-1, 2, 4-triazolium iodide with dimethyl acetylenedicarboxylate or methyl propiolate in the presence of alkali followed by heating with water gave methyl 1H-pyrazole-4-carboxylates in low yields, and reaction of 4-acylimino-1-methyl-1H-1, 2, 4-triazolium betaines with methyl propiolate afforded 5-substituted 1-methyl-1H-1, 2, 4-triazoles.
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HIROSHI MIYAZAKI, HIDEO ABUKI
1976 Volume 24 Issue 10 Pages
2572-2574
Published: October 25, 1976
Released on J-STAGE: March 31, 2008
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To investigate the pharmacokinetics of d-chlorpheniramine (d-CPA) and its l-isomer, d-CPA-d
6 and l-CPA-d
0 were administered orally and simultaneously to healthy adult volunteers. Both isomers in the serum were measured by chemical ionization-mass fragmentography using dl-CPA-d
13 as an internal standard. The concentration of d-isomer was higher than that of l-isomer and the ratio (d/l) of both isomers was 1.9-3.1, and the biological half-lives of d- and l-isomer were 24 hr and 15 hr, respectively.
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