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KIYOSHI TAKIURA, KAZUAKI KATAOKA, YOSHIO SASAKI
1977 Volume 25 Issue 10 Pages
2477-2481
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Cryptotanshinone was isolated from tanshinone III as a Fe (III) complex. The cryptotanshinone-Fe (III) complex was obtained by mixing anhydrous FeCl
3 with cryptotanshinone in glacial acetic acid, and it decomposed to its original components on addition of water. Elemental analysis and measurements of the molar conductance, molecular weight and infrared and far-infrared spectra of this complex suggested that it is an equimolar complex [Fe (cryptotanshinone) Cl
3] in which cryptotanshinone is a bidentate ligand of the o-quinone type. This complex exhibited an absorption maximum at 560 nm in benzene, and was shown to have a 1 : 1 composition by the continuous variation, slope ratio and molar ratio methods. Similar complexes of related compounds were also 1 : 1. The apparent stability constants of these complexes, measured by molar ratio method, were compared ; results suggested that the ether oxygen of cryptotanshinone contributes to the stability of this complex.
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MASAKATSU KANEKO, MISAKO KIMURA, TAKUZO NISHIMURA, BUNJI SHIMIZU
1977 Volume 25 Issue 10 Pages
2482-2489
Published: October 25, 1977
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9-(β-D-Arabinofuranosyl) adenine (Ara-A) was synthesized from adenosine 5'-monophosphate in 30% yield via 8, 2'-O-cycloadenosine as an intermediate. Various 8-substitutedamino Ara-A derivatives were obtained by aminolysis of 8, 2'-O-cycloadenosine and N
6-substituted Ara-A derivatives were also obtained by reaction of 6-chloro-9-(β-D-arabinofuranosyl) purine with amines. In vitro antiviral activities of the N
6- or 8-substituted Ara-A were determined by the degree of cytopathic effect inhibition.
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YOSHINOBU NAKAI, EIHEI FUKUOKA, SHINICHIRO NAKAJIMA, KEIJI YAMAMOTO
1977 Volume 25 Issue 10 Pages
2490-2496
Published: October 25, 1977
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Nitrogen gas adsorption isotherms are obtained on intact, 8 and 32 hours ground microcrystalline cellulose. Before the determination of adsorption isotherms, each specimen is dispersed into water, then the water is changed to ethanol, ethanol to n-pentane, and the n-pentane is evaporated in vacuo. Specific surface area is determined from the nitrogen gas adsorption method as 79, 153 and 250 m
2/g for each sample, using B.E.T. equation. This result shows that the effective surface available to water molecules is equivalent to that available to nitrogen molecules. Pore size distribution was determined from both nitrogen gas desorption isotherms and X-ray small angle scattering. Significant change in pore size distribution by grinding is not observed. The effective surface area of microcrystalline cellulose is composed of pores which range in diameter is up to 300 Å, and relatively small pores, up to 100 Å, play an important role. Recrystallization of amorphous cellulose is observed to be caused by the solvent displacement, to the same crystal form as cellulose II. The possible relation of these observations to the fine structure of ground microcrystalline cellulose is discussed.
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MASAHIRO INAGAKI
1977 Volume 25 Issue 10 Pages
2497-2503
Published: October 25, 1977
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The relationship of racemic structure to resolution by preferential crystallization was discussed on the ternary phase diagrams of systems containing optical isomers and a solvent. From these discussions, it was concluded that the resolution by this method is applicable only to racemic mixtures, and that racemic compounds and also racemic solid solutions can not be resolved. In addition, we reexamined the resolution of 3, 3-diethyl-5-methyl-2, 4-dioxopiperidine reported to be resolved by this method in spite of the formation of a racemic solid solution, and found it impossible to resolve this compound by preferential crystallization.
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HIDEO MATSUMARU, SEISHI TSUCHIYA, TOSHIHARU HOSONO
1977 Volume 25 Issue 10 Pages
2504-2509
Published: October 25, 1977
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The ajmaline-PVP coprecipitates were prepared for the purpose of increasing the solubility of ajmaline. The dissolution rate of 1 : 5 w/w coprecipitate was approximately 130-fold enhanced compared with ajmaline. In nuclear magnetic resonance (NMR) spectrum of ajmaline, the signal of C (21)-proton was shifted to lower magnetic field by polyvinylpyrrolidone (PVP), and 2-pyrrolidone showed the same effect on ajmaline, while NMR spectrum of 17, 21-diacetylajmaline was not affected by PVP. On addition of PVP, the λ
max of ajmaline shifted to shorter wavelength in chloroform, but ultraviolet (UV) spectra of diacetylajmaline were not affected. By 2-piperidine, the shift of C (21)-proton signal of ajmaline in NMR spectra could not be detected. From these results, C (21)-hydroxyl groups of ajmaline were considered to form weak hydrogen bond to carbonyl groups of pyrrolidone rings of PVP. The coprecipitate and the physical mixture of PVP and diacetylajmaline, in which the interaction could not be detected as far as spectroscopic investigation was concerned, were also prepared. The dissolution rate of diacetylajmaline was enhanced in the coprecipitate and slightly in the physical mixture compared with that of diacetylajmaline alone. From the solubility study and the equilibrium dialysis study, it was suggested that one PVP molecule interacts with two or three molecules of ajmaline or diacetylajmaline in aqueous solution. The dissolution characteristics of ajmaline-PVP coprecipitate were discussed in comparison with diacetylajmaline-PVP coprecipitate.
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SHINZO KANO, TSUTOMU YOKOMATSU, TOSHIHIRO ONO, YOKO TAKAHAGI, SHIROSHI ...
1977 Volume 25 Issue 10 Pages
2510-2515
Published: October 25, 1977
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The reaction of 1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-1-(3, 4-methylenedioxyphenyl)-2, 2-dimethylisoquinolinium iodide (3) with dimsylsodium afforded the 1-methyl-1-phenylisoquinoline (4) and the N, N-dimethyldiphenylmethylamine (5). Similar reaction using the berbine methiodide (8), (16), (17) yielded the corresponding ochotensine type 1-spirobenzylisoquinolines (9), (14), and (15), respectively. The homoberbine (20) also gave the 1-spiroisoquinoline (22), however, the reaction of the homoberbine (23) with dimsylsodium yielded the tetrahydro-13, 14-trans-dibenz [c, g] azacycloundecine (28).
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NORIKO MOTOHASHI, ITSUHIKO MORI, YUKIO SUGIURA, HISASHI TANAKA
1977 Volume 25 Issue 10 Pages
2516-2523
Published: October 25, 1977
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The radioprotective effect of ergothioneine, 2-mercaptoimidazole, and 2-mercapto-1-methylimidazole, containing mercaptoimidazole ring as thione form, has been compared with that of the aminothiols such as cysteine and cysteamine. Irradiation of the brown metmyoglobin only causes the formation of the bright red myoglobin which has ferryl structure. The conversion is inhibited by the addition of a 10- and 30-fold molar excess of ergothioneine and cysteine to metmyoglobin, respectively. The addition of cysteine exceeding the radioprotective concentration forms the green color sulfmyoglobin, which is an abnormal blood pigment. Ergothioneine allows the spectral change of metmyoglobin only by γ-irradiation in the addition of a 1000-fold molar excess, but no sulfmyoglobin forms. The spectrum in the presence of ergothioneine shows simply the formation of oxymyoglobin. The mechanism for the formation of ferrylmyoglobin, oxymyoglobin and sulfmyoglobin is also discussed.
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KAZUYUKI HIRANO, MAMORU SUGIURA, KAZUMASA MIKI, SHIRO IINO, HIROSHI SU ...
1977 Volume 25 Issue 10 Pages
2524-2529
Published: October 25, 1977
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Human alkaline phosphatases from placenta and intestine with molecular weight of 130000 and 170000, respectively, are composed of two subunits with molecular weights of approximately 65000 and 86000, respectively. These two enzymes were shown to have distinct different amino acid compositions and they are glycoprotein. Isozyme about human alkaline phosphatase was also discussed.
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MITSUO NAKAGAWA, HAYAO KOBAYASHI, SHOJI KOJIMA, ATSUKO UEMURA, MITSURU ...
1977 Volume 25 Issue 10 Pages
2530-2534
Published: October 25, 1977
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The inhibitory actions of organophosphate pesticides on cholinesterase and lecithincholesterol acyltransferase in human plasma and acetone powder of human plasma were compared in vitro. Acetone powder of human plasma as well as native human plasma was able to use as an enzyme source of the esterification of cholesterol in sonicated dispersion of lecithin and cholesterol mixture. The acyltransferase in acetone powder of human plasma was inhibited approximately 55, 60 and 97% by the addition of 1×10
-3M sumithion, dimethyldichlorovinylphosphate (DDVP) and diisopropylfluorophosphate (DFP), respectively. On the other hand, even though human plasma preincubated with 1×10
-3M sumithion, DDVP or DFP for 60 min at 37° and then extracted with cold acetone, the decreased acyltransferase activity was not recovered. In addition, the decreased acyltransferase activities in human plasma with 1×10
-3M DDVP and acetone powder prepared from human plasma preincubated with 1×10
-3M DDVP were not recovered by the addition of 1×10
-5M or 1×10
-3M 2-pyridine aldoxime methiodide (PAM). Human plasma cholinesterase was also inhibited at concentrations of DDVP ranging from 1×10
-7M to 1×10
-5M in vitro. In particular, the cholinesterase was completely inhibited by the addition of 1×10
-5M DDVP. However, cholinesterase activity in acetone powder prepared from human plasma preincubated with 1×10
-3M DDVP exhibited approximately 8-15% of that in acetone powder prepared from human plasma preincubated without DDVP. The decreased cholinesterase activities in human plasma with 1×10
-7-10
-5M DDVP and in acetone powder prepared from human plasma preincubated with 1×10
-3M DDVP were recovered by the addition of 1×10
-3M PAM. These results suggest that the inhibitory action of organophosphate pesticides on the acyltransferase in human plasma may be different from that on plasma cholinesterase.
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KOJI YAMAKAWA, TSUYOSHI SATOH
1977 Volume 25 Issue 10 Pages
2535-2544
Published: October 25, 1977
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The total synthesis of (±)-ligularone (3) via diene adduct (17) is described. 3, 5-Dimethylbenzofuran-4, 7-quinone (14) was prepared starting from resorcinol. A mixture of 14 and diene (16) was refluxed in benzene for 48 hr to afford the desired adduct (17) in 70% yield. Treatment of 17 with silica gel gave 10-epimer (20). 20 was reduced with NaBH
4 followed by treatment of aq-AcOH to give 3, 6-dioxo-9β-ol (21) and 9α-ol (22). Dehydration of 21 and 22 gave 23 which was epimerized to give 4β-methyl compound (24), in low yield. Catalytic reduction of 24 gave furanoeremophilan-3, 6-dione (28). 28 was also synthesized by catalytic reduction of 23 followed by acid-epimerization of the resulting diketone (30), in good yield. Stereochemistry of diketone (28) and (30) are discussed by nuclear magnetic resonance (NMR) spectrometry. Desulfurization of thioketal of 28 followed by catalytic reduction of the resulting product afforded (±)-ligularone (3). The infrared and NMR of (±)-(3) were identical with those of natural ligularone. Furanoeremophilan-3, 6, 9-trione (36) was synthesized from diene adduct (17) and (20) via (34) and (35) in good yield, respectively.
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HIROSHI HOSODA, KOUWA YAMASHITA, SHIGEO IKEGAWA, TOSHIO NAMBARA
1977 Volume 25 Issue 10 Pages
2545-2553
Published: October 25, 1977
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Derivatization of a hydroxyl group into the tert-butyldimethylsilyl ether was shown to be useful for selective blockage of coordination of the substrate with the lanthanide shift reagent in
1H nuclear magnetic resonance spectroscopy. This method was conveniently applied to confirmation of the labeled position with deuterium in the dioxygenated steroids.
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MIKIO YAMAZAKI, HARUHIRO FUJIMOTO, EMI OKUYAMA
1977 Volume 25 Issue 10 Pages
2554-2560
Published: October 25, 1977
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Structures of tryptoquivaline C and D, isolated from Aspergillus fumigatus were determined as I and II. The stereostructure of I was determined by direct comparison of I with tryptoquivaline which structure was determined by X-ray analysis already. Stereostructure of II was determined by comparison of its spectral data with that of I and from the result that compound A (VIa or b) was obtained on oxidation of both I and II. Since L-(+)-alanine was obtained by hydrolysis of a reduction product from II, S-configuration was proposed on the stereochemistry of C-15 in II.
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JUN WATANABE, RYUICHIRO FUJITA
1977 Volume 25 Issue 10 Pages
2561-2567
Published: October 25, 1977
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In order to estimate the extent of gastrointestinal absorption of methylene blue (MB) in dogs and to search for more contributory route of excretion than urine, elimination of MB was investigated after oral and intravenous administration at a dose of 15 mg/kg in mongrel dogs. After oral administration, total MB, which was the sum of unchanged MB and leucomethylene blue (LMB), was recovered from urine and feces with averages of 3.9 and 44.3% of the dose, respectively. When MB was intravenously injected at the same dose, total urinary and fecal recoveries were 6.6 and 19.9%, respectively. Therefore, it was assumed that about 60-70% of orally administered MB should have been absorbed from the gastrointestinal tracts of dogs. In anesthetized dogs, total biliary recovery was about 7 times greater than that from urine after intravenous administration of MB to dogs. On the basis of these results, it was concluded that total urinary recovery should not be taken as an index of gastrointestinal absorption after oral administration of MB to dogs, and that there would not be a great species difference in gastrointestinal absorption of MB between man and the dog. A few metabolites other than LMB were found in urine and feces of dogs, though quantitative analysis was not carried out.
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YOSHIHARU KARUBE, YOSHIKAZU MATSUSHIMA
1977 Volume 25 Issue 10 Pages
2568-2575
Published: October 25, 1977
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Schiff bases of 3-hydroxy-4-formylpyridine (1), pyridoxal (PL), pyridoxal-5'-phosphate (PLP), and related aldehydes with methyl valinate, n-butylamine, and various amino acids and their derivatives were prepared and their absorption spectra in various solvents and in acidic, neutral and alkaline methanol were measured. From the spectral analyses, the longest π bands of the eight possible molecular species of the Schiff base of 1 involved in acid-base equilibrium were determined as follows ; anion, 368 nm ; enolimine, 325 nm ; ketoenamine, 420 nm ; species with a phenolate and a pyridinium groups, 385 nm ; species with a protonated azomethine and a phenol group, 365 nm ; ketoenamine with a pyridinium group, 425 nm ; enolimine with a pyridinium group, 330 nm ; fully protonated species, 365 nm. Equilibria between equally protonated species were dependent on media and on the amine part. The wavelengths of the π bands were affected by media and slightly by the amine part. Corresponding species of Schiff bases of PL and PLP have the π band at the longer wavelength side of less than 10 nm. Infrared and proton magnetic resonance data of the Schiff bases are presented.
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MASUO MORISAKI, SUSUMU SATO, NOBUO IKEKAWA
1977 Volume 25 Issue 10 Pages
2576-2583
Published: October 25, 1977
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The four stereoisomers of 20, 22-dihydroxycholesterol 9, 10, 17 and 19 were synthesized from pregnenolone. Vinylation of the 3, 5-cyclo derivative 1 of pregnenolone gave the [20S]-carbinol 2, which was then oxidized with m-chloroperbenzoic acid to afford the [22S]-22, 23-epoxide 3 and its [22R]-isomer 4 (7 : 2). Reaction of 3 and 4 with i-Bu
2CuLi followed by acid treatment yielded 20R, 22S-dihydroxycholesterol 9 and its 20R, 22R-isomer 10, respectively. The latter triol 10 was more effectively prepared by a Grignard reaction on the [20S]-20-formyl-carbinol 14, which was derived from pregnenolone THP ether 12, through the 1, 3-dithiane derivative 13. Oxidation of 20-dehydrocholesterol acetate 16 with OsO
4 gave stereoselectively the 20S, 22S-glycol 17 (R=Ac). Treatment 17 (R=Ac) with N-chlorosuccinimide-dimethylsulfide followed by reduction with LiAlH
4 afforded 20S, 22R-dihydroxycholesterol 19 together with the 20S, 22S-isomer 17 (R=H) (3 : 2). Acid-catalyzed epoxide opening reactions of 20, 22-epoxycholesterols were also discussed.
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TAKESHI HARA, HITOSHI FUJIMORI, YASUTAKA KAYAMA, TOSHIRO MORI, KAZUHIK ...
1977 Volume 25 Issue 10 Pages
2584-2592
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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A series of 6-phenyl-4H-imidazo [1, 2-α] [1, 5] benzodiazepin-5 (6H)-ones (1) was synthesized starting from 2-nitrodiphenylamines (9) and was evaluated for CNS activity. Bromoacetylation of 9 to N-bromoacetyl-2-nitrodiphenylamines (10) and subsequent treatment of 10 with sodium cyanide gave N-cyanoacetyl-2-nitrodiphenylamines (11) which were also prepared directly from 9 by cyanoacetylation. The reduction of the nitro group of 11 to give 2-amino-N-cyanoacetyldiphenylamines (12) followed by cyclization of 12 with HCl afforded 4-amino-1-phenyl-2H-1, 3-dihydro-1, 5-benzodiazepin-2-ones (13). Treatment of 13 with propargylamine in the presence of p-toluenesulfonic acid or with α-bromoketone gave 1. Some of 1 were also synthesized by treatment of 13 with α-aminoaldehyde acetal to the amidine derivatives 14 followed by their cyclization in formic acid. Although the ED
50 for the antipentetrazole activity of 8-chloro-2-ethyl-6-phenyl-4H-imidazo [1, 2-α] [1, 5] benzodiazepin-5 (6H)-one (1h) was 5.5 mg/kg, the ratio of antipentetrazole to muscle relaxant activity and that of taming to muscle relaxant activity of 1h were fairly large compared with those of diazepam.
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NORIKI KIRIYAMA, KEIICHI NITTA, YOSHIAKI SAKAGUCHI, YASUHISA TAGUCHI, ...
1977 Volume 25 Issue 10 Pages
2593-2601
Published: October 25, 1977
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A new type metabolite (I) was isolated from Aspergillus terreus var. africanus IFO 8835 together with terrein, 3, 6-dihydroxytoluquinone, emodin, questin, sulochrin, dihydroerdin, geodin, asterric acid, and aspulvinone D. The structure of I was determined as α-oxo-β-(p-hydroxyphenyl)-γ-(p-hydroxy-m-3, 3-dimethylallylbenzyl)-γ-methoxycarbonyl-γ-butyro-lactone by chemical and physical experimental data. Compound I was biosynthesized by intact condensation of two phenylpropanoids between carbons 2 and 3'.
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MAMORU SUZUKI, KAZUO MATSUMOTO, MUNEJI MIYOSHI, NAOTO YONEDA, RYUICHI ...
1977 Volume 25 Issue 10 Pages
2602-2607
Published: October 25, 1977
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3-Amino-4-hydroxyquinolin-2 (1H)-one compounds (aminocarbostyrils) were synthesized by a reaction of methyl isocyanoacetate with isatoic anhydrides in the presence of 1, 8-diazabicyclo [5, 4, 0] undec-7-ene (DBU), followed by hydrolysis with HCl. The alkylation of oxazolo [4, 5-c] quinolin-4 (5H)-ones which are the intermediates of the aminocarbostyrils and the acylation of aminocarbostyrils were also investigated. Furthermore, a variety of the quinolin-2 (1H)-one analogs showed antiallergic activity.
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KOZO TAKAYAMA, NAOKI NAMBU, TSUNEJI NAGAI
1977 Volume 25 Issue 10 Pages
2608-2612
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The interaction of sulfonamides with 18-crown-6 (1, 4, 7, 10, 13, 16-hexaoxacyclooctadecane) was studied, observing the effect on the solubility of sulfonamides in organic solvents. In benzene solution, sulfamonomethoxine and sulfamethoxazole formed the respective crystalline complexes with 18-crown-6. The stability constant K for sulfamonomethoxine/18-crown-6 system was particularly large in comparison with the other systems. In chloroform solution, however, the solid complex was not obtained in any systems. K values in chloroform were smaller than those in benzene. Furthermore, when the complex formation of sulfamethomidine with 18-crown-6 was investigated in various dielectric constants of solvents, K value decreased with the increase in polarity of the solvent. These results indicated that the hydrogen bonding might be a primary force of the formation of these complexes. Additionally, the complex formation in solid phase was confirmed in sulfamonomethoxine/18-crown-6 and sulfamethoxazole/18-crown-6 systems by powder X-ray diffractometry and differential scanning calorimetry. From infra-red and nuclear magnetic resonance spectra, it was suggested that 4-amino group of sulfonamide might interact with the oxygen of ether ring of 18-crown-6.
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KENJI SUZUKI, NOBUYOSHI ENDO, YUSUKE SASAKI
1977 Volume 25 Issue 10 Pages
2613-2616
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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For the synthesis of peptide containing glutamic acid residue (s) by solid phase peptide synthesis, γ-phenacyl or γ-nitrobenzyl ester group, which is stable to anhydrous hydrogen fluoride (HF), was used as γ-carboxyl protecting group of glutamic acid to minimize the side reactions. The protected peptide resins were treated with HF-anisole mixture followed by deprotection of the γ-carboxyl protecting group under mild conditions. This strategy gave a satisfactory result without detectable side reactions in the preparations of two model dipeptides, H-Ala-Glu-OH and H-Asn-Glu-OH, by solid phase peptide synthesis.
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AKIRA TAKAMURA, SHUNICHI NORO, SHIGEKI ANDO, MASUMI KOISHI
1977 Volume 25 Issue 10 Pages
2617-2623
Published: October 25, 1977
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In this study, one of the purpose is the comparison of the capabilities of machines as emulsifying equipments. The other purpose is to evaluate the stability of emulsion prepared above equipments, from the changes of turbidities in the course of time. The Flow Jet Mixer, the Agitator, and the Colloid-Mill were used as emulsifying equipments. Mixtures of n-C
7H
16 and CCl
4 were employed as the dispersed phase. Each sample of emulsion was quickly photographed under an optical microscope, in succession, the mean length diameter and the particle size distribution were calculated. Furthermore, the shear velocity du/dx could be calculated at three emulsifying equipments. The following results were obtained : (1) The size distribution curves of emulsions prepared by Colloid-Mill and Flow Jet Mixer had a sharper and narrower shape. (2) The values of shear velocity were 6.37×10
5 at Agitator, 1.94×10
6 at Flow Jet Mixer, and 5.70×10
6 (1/sec) at Colloid-Mill, respectively, when the concentration of dispersed phase was kept at 3.55% (v/v).
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KIYOMI KIKUGAWA, HIDEO SUEHIRO, AKIJI AOKI
1977 Volume 25 Issue 10 Pages
2624-2637
Published: October 25, 1977
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A series of S-substituted 2-thioadenosines (IV) were prepared by treatment of 2-thioadenosine (III) with a requisite halide in NaOH-H
2O, NaOH-H
2O-EtOH, Na/dimeth-ylformamide, NaOMe/dimethylformamide or NaH/dimethylformamide. N-Substituted 2-aminoadenosines (V) were obtained by treatment of 2-chloroadenosine (II) with a requisite amine. Compounds (IV and V) and N-oxide derivatives of them were tested as inhibitors of adenosine 5'-diphosphate- and collagen-induced rabbit platelet aggregation. 2-Cycloalkyl- or 2-polycycloalkylthioadenosines (IV
7-9), water-soluble 2-piperazino-ethylthioadenosines (IV
16-19) and 2-thioadenosine N-oxide (X
2) were found effective. Most of them showed long lasting activity during the incubation with rabbit plasma. Compounds (IV
7-9) were also inhibitory against human platelet aggregation.
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ISAO KITAGAWA, HIROTAKA SHIBUYA, MACHIKO KAWAI
1977 Volume 25 Issue 10 Pages
2638-2643
Published: October 25, 1977
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Biogenetic-type conversions of an eudesmane-type sesquiterpene alantolactone (4) to several furanoeremophilanes (10a, 10b, 12a, 12b) including naturally occurring 6-acetoxy-1, 10-epoxy-euryopsin (12b) have been accomplished. The conversions constitute the formal total syntheses of these furanoeremophilanes via the biogenetic-type angular methyl migration of the eudesmane-type precursor. It has been also demonstrated that the biogenetic-type transformation starting from the eudesmane-type 5α, 6α-epoxide may be a useful process in the synthetic pathway of eremophilane-type sesquiterpene.
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AKIRA TAKAMURA, SHUNICHI NORO, SHIGEKI ANDO, MASUMI KOISHI
1977 Volume 25 Issue 10 Pages
2644-2649
Published: October 25, 1977
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The object of this paper is to be determined the calculation equation between the turbidity and the specific interfacial area of dispersion for emulsion systems. The emulsion was prepared by the Flow Jet Mixer. The droplet size distributions were concurrently measured by the turbidimetric method and the microscopic method. Distilled water and mixtures of n-C
7H
16 and CCl
4 were used as continuous phase and the dispersed phase, respectively, in absence of emulsion agent. Hence, the following results were obtained. 1) The relationship between the turbidity, I, and the concentration of dispersed phase, C, were as following. log I=1.321 log C+β where β was the intercept. 2) As same as presented in term 1), the relation between the specific interfacial area, S, and the concentration of dispersed phase were represented by, S=-2046 log C+β' Consequently, where β' was the intercept. 3) Combining above two equations, the next calibration equation could be established for these emulsion systems. S=4505+log (I
1590/C
2046)
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HIROSHI HOSODA, KOUWA YAMASHITA, KYOICHI TADANO, TOSHIO NAMBARA
1977 Volume 25 Issue 10 Pages
2650-2656
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The preparation of 15α-hydroxytestosterone (5) and 15α-hydroxyandrostenedione (11) was carried out employing 17β-tert-butyldimethylsilyloxy-6β-methoxy-3α, 5-cyclo-5α-androstan-15α-ol (1) as a key intermediate. In a similar fashion the 15α-hydroxylated 5α-androstane derivatives (20, 22, 26) were also synthesized. The utilization of tertbutyldimethylsilylation for protecting the hydroxyl group in the preparation of the desired compounds has been demonstrated.
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KANAME MORITA, MANABU HANANO, YUICHI SUGIYAMA, SHOJI AWAZU
1977 Volume 25 Issue 10 Pages
2657-2668
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The pharmacokinetics of riboflavin-5'-phosphate (FMN) and the metabolite riboflavin (FR) in the rat was studied with measurement of the plasma levels after the injection into femoral and portal vein of the FMN dose of 1 and 10 mol. Area under the curve (AUC) of FR plasma level vs. time after FMN injection into portal vein was found to be larger than the case of femoral vein. This route dependency of AUC in active metabolite was successfully explained from viewpoint of the compartment theory of linear pharmacokinetics. The AUC of FR was also varied by the dose of FMN. This dose dependency was analyzed to be the decrease in total clearance of FR with increasing FMN dose. The model dependent rate constants in FMN and FR pharmacokinetics did not vary with the dose and route but the distribution volume of FR did. The per cent of FR excreted in bile and urine in 24 hours after injection of FMN did not vary with the dose and route of FMN injection.
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TATSUYA TAKANO, MASAO SATO
1977 Volume 25 Issue 10 Pages
2669-2675
Published: October 25, 1977
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Oleate-rich cholesteryl ester (CE) in serum and arterial wall increased after cholesterol administration. Concentration of oleic acid in CE increased further, after removal of cholesterol diet. This paper suggested that CE hydrolytic enzymes as well as synthetic enzymes might involve in the accumulation of oleate-rich CE in serum and arterial wall.
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MASAKATSU OHZEKI, TOMISHIGE MIZOGUCHI, KENJI KOGA, SHUNICHI YAMADA
1977 Volume 25 Issue 10 Pages
2676-2680
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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A new stereoselective synthesis of methyl α-L-amicetoside (11), methyl α-L-mycaminoside (14) and methyl α-L-oleandroside (17) starting from L-alanine is described. It is shown that methyl 2, 3, 6-trideoxy-α-L-hex-2-enopyranosid-4-ulose (8) is readily accessible from L-alanine in optically pure state and is a potential intermediate for the synthesis of various kinds of 6-deoxy-L-hexoses.
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KIYOSHI TOMIOKA, KENJI KOGA, SHUNICHI YAMADA
1977 Volume 25 Issue 10 Pages
2681-2688
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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A first biogenetic-type asymmetric synthesis of natural (+)-maritidine from L-tyrosine is described. Phenolic oxidative coupline of monophenol (10b) with thallium (III) trifluoroacetate afforded the corresponding spiro dienone (11b) in 66.5% yield. Asymmetric cyclization of dienone (14) was found to occur highly selectively to give one diastereomer (15) preferentially. Removal of the carboxamide group in 15 was effected by reductive decyanization of the intermediate amino nitrile (18) by sodium in liquid ammonia to (+)-epimaritidine (19), which was epimerized to the objective (+)-maritidine by the known method.
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KIYOSHI TOMIOKA, KENJI KOGA, SHUNICHI YAMADA
1977 Volume 25 Issue 10 Pages
2689-2691
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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An alternate method for reductive decyanization of α-amino nitriles to the corresponding amines was exploited using sodium in liquid ammonia. This method eliminated the limitation encountered in the reaction with sodium borohydride. Using this new process, optically active α-amino nitrile (8) was decyanized to 9 without racemization.
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TETSUZO KATO, HITOSHI KIMURA
1977 Volume 25 Issue 10 Pages
2692-2696
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Acylation of ethyl 4-bromo-3-hydroxybutanoate (I) with acetic anhydride, benzoyl chloride, diketene, and phenyl isocyanate gave rise to ethyl 3-acetoxy-4-bromobutanoate (IIa), ethyl 3-benzoyloxy-4-bromobutanoate (IIb), ethyl 3-acetoacetoxy-4-bromobutanoate (IIc), and ethyl 4-bromo-3-(N-phenylcarbamoyloxy) butanoate (IId), respectively. Reaction of IIa with sodium ethoxide in abs. ethanol gave ethyl 4-hydroxycrotonate (III) and ethyl 4-bromocrotonate (IV). The similar reaction of IIb afforded IV and 4-benzoyloxycrotonate (Vb). Similarly, IIc was converted to III, 4-acetoacetoxycrotonate (Vc), and 3-acetyl-4-ethoxycarbonylmethyltetrahydrofuran-2-one (VI). On the other hand, reaction of IId under the same condition did not give the acyl migrated product such as ethyl 4-N-phenylcarbamoyloxycrotonate (Vd) but afforded ethyl 4-anilinocrotonate (VIII).
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TETSUZO KATO, TAKUO CHIBA, SHIGERU TANAKA, TOSHIKI SASAKI
1977 Volume 25 Issue 10 Pages
2697-2701
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Reaction of isoquinolinium bis (ethoxycarbonyl) methylide (I) with ethyl acetoacetate gave ethyl 1-acetyl-2-hydroxypyrrolo [2, 1-α] isoquinoline-3-carboxylate (IV), ethyl 2-methylpyrrolo [2, 1-α] isoquinoline-3-carboxylate (V), diethyl 2-methylpyrrolo [2, 1-α] isoquinoline-1, 3-dicarboxylate (VII), and ethyl 2-ethoxycarbonylmethylpyrrolo [2, 1-α]-isoquinoline-3-carboxylate. Similar reaction of isoquinolinium cyano (ethoxycarbonyl)-methylide (II) with ethyl acetoacetate gave 3-cyano-2-methylpyrrolo [2, 1-α] isoquinoline (IX) and ethyl-3-cyano-2-methylpyrrolo [2, 1-α] isoquinoline-1-carboxylate (X) besides compound VIII. Similarly, reaction of pyridinium bis (ethoxycarbonyl) methylide (XI) with ethyl acetoacetate gave ethyl 1-acetyl-2-hydroxyindolizine-3-carboxylate (XIII).
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MORIO IKEHARA, WONGYL LIMN, TOSHIKAZU FUKUI
1977 Volume 25 Issue 10 Pages
2702-2707
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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8-Methyladenosine (X) was synthesized by two ways starting from 2', 3'-O-isopropylidene-2-methylthioinosine (I). The compound (I) was methylated with t-butyl hydroperoxide in acidic media in the presence of ferrous ion to give 8-methyl compound (II) in a yield of 46%. Raney nickel dethiolation of II and acetylation at 5'-OH followed by chlorination using SOCl
2/DMF gave 6-chloro-8-methylpurine derivative (V). The compound (V) was treated with liq. NH
3 and deprotected with trifluoroacetic acid to give 8-methyladenosine (X). Alternatively II was acetylated at 5'-OH, chlorinated with Vilsmeyer-Haack reagent and treated with liq. NH
3 to give 2', 3'-O-isopropylidene-2-methylthio-8-methyladenosine (IX). The compound (IX) was deacetonized and dethiolated with Raney nickel to give X. The physical properties of X was elucidated by ultraviolet, circular dichroism and nuclear magnetic resonance spectra. A syn type conformation was assigned to 8-methyladenosine.
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MASAHIKO TSUBOI, MASAFUMI MINAMI, GENICHIRO NONAKA, ITSUO NISHIOKA
1977 Volume 25 Issue 10 Pages
2708-2712
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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From the Japanese rhubarb, "Shinshu Daio, " two new naphthalene glycosides, I, mp 150-152°, [α] D-119.0°, C
20H
24O
9·H
2O and II, [α] D-102.0°, C
22H
24O
12·3 1/2H
2O were isolated together with 6-hydroxymusizin 8-O-β-D-glucopyranoside which was found to be identical with the one isolated from aphid, Aphis nerii. By the chemical and spectral evidences, the structures of I and II were characterized to be torachrysone 8-O-β-D-glucopyranoside and torachrysone 8-O-β-D-(6'-O-oxalyl)-glucopyranoside, respectively.
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KATSUHIKO NAGAHARA, ATSUSHI TAKADA
1977 Volume 25 Issue 10 Pages
2713-2717
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Treatment of isatoic anhydrides with hydrazine hydrate gave 1, 2-bis-(o-aminobenzoyl)-hydrazines (IIa-c). The reaction of IIa, b with ethoxymethylenemalononitrile, ethyl ethoxymethylenecyanoacetate or triethyl orthoformate afforded new 3, 3'-bisquinazoline-4, 4'-diones (IIIa, b and IVa-d) in good yields. On the other hand, the reaction of IIa-c with polyphosphoric acid furnished 2, 5-diaryl-1, 3, 4-oxadiazole derivatives in high yields.
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ISAO KITAGAWA, HIROTAKA SHIBUYA, HIROMICHI FUJIOKA
1977 Volume 25 Issue 10 Pages
2718-2730
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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In continuing studies on the elucidation of essential factors for the favorable biogenetictype angular methyl migration starting from 5α, 6α-epoxy-eudesman-8β, 12-olide (1) leading to several eremophilanolides, four related eudesmane-type 5, 6-epoxides (4, 5, 6, 7) have been prepared and treated under four different acid conditions. Based on the product analyses, it has been demonstrated that the following three factors seem to be important for the biogenetic-type 10-methyl migration of 1 giving eremophilane-type derivatives : i) the presence of 5α, 6α-epoxide function, ii) the spatial interaction between 10-methyl and 4β-methyl which would bring about distortion of the ring A, and iii) the presence of cis-γ-lactone moiety attached to C-7 and C-8.
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YUICHIRO YABE, AKIRA MORITA, CHIEKO MIURA, SHINSAKU KOBAYASHI, YOSHIHI ...
1977 Volume 25 Issue 10 Pages
2731-2734
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Three analogues of tetragastrin, in which the tryptophan residue was substituted by 3-(1-naphthyl)-L-alanine, 3-(2-naphthyl)-L-alanine or 1, 2, 3, 4-tetrahydro-β-carboline-3-carboxylic acid, were synthesized and evaluated for their gastric juice stimulating activity. The results suggest that the indolyl NH function in the tryptophan residue plays an important role and that the role of the tryptophan residue in an interaction between tetragastrin and its receptor is different from that in the case of luteinizing hormonereleasing hormone.
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TETSUJI KAMETANI, TERUMI HIGA, CHUVAN LOC, MASATAKA IHARA, KEIICHIRO F ...
1977 Volume 25 Issue 10 Pages
2735-2738
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Condensation of salicylic acid chloride (VI) with 3, 4-dihydro-β-carboline (VII) gave 6, 7, 8, 13b-tetrahydro-5-oxo-5H-β-carbolino [1, 2-b] [1, 3] benzoxazine (X), which was also synthesised by a reaction of VI with N-formyltryptamine (VIII). The same reaction of VI with isoquinoline (XIV) and 3, 4-dihydro-6, 7-dimethoxy-1-methylisoquinoline (XVI) afforded the corresponding benzoxazinones (XV and XVII), respectively.
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MINORU MACHIDA, MIKIKO I. MACHIDA, YUICHI KANAOKA
1977 Volume 25 Issue 10 Pages
2739-2743
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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p-Substituted phenylmaleimides were synthesized and their hydrolytic rates were measured by dual-wavelength method. Hammett plot for the hydrolysis of p-substituted phenylmaleimide yields a straight line of p=0.35 with relative coefficiency r=0.99. The half-life times of a series of maleimide derivatives including the practical fluorescent thiol reagents such as N-[p-(2-benzimidazolyl) phenyl] maleimide, N-(1-anilinonaphthyl-4)-maleimide and N-(7-dimethylamino-4-methyl-3-coumarinyl) maleimide were compared and their stabilities in aqueons media were discussed.
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FUMIKO ABE, TATSUO YAMAUCHI
1977 Volume 25 Issue 10 Pages
2744-2748
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Cardenolides in the seeds, bark, and leaves of Cerbera manghas L. were investigated. From the seeds, tanghinigenin glycosides were isolated along with known digitoxigenin glycosides, cerberin, neriifolin, thevetin B, and 2'-O-acetyl thevetin B. From the barks of root and stem, gentiobiosyl thevetoside, glucosyl thevetoside, and thevetoside of tanghinigenin and 17βH-tanghinigenin were obtained. The cardenolides in the air-dried leaves were found to vary with seasons. 17βH-neriifolin is major and preferable to neriifolin in July, while 17βH-deacetyltanghinin and deacetyltanghinin present in the leaves of Feb.
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TAKASHI TSUCHIYA, HEIHACHIRO ARAI, HIROSHI HASEGAWA, HIROSHI IGETA
1977 Volume 25 Issue 10 Pages
2749-2754
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The photo-sensitized oxygenation of 1, 2-diazepines (1 and 12) and azepine (17) results in the formation of the corresponding relatively stable epidioxides (2, 13, and 18). The dioxides (2) react with potassium hydroxide to give the epoxy-ketones (10) and with methanol to give the solvent adducts (11), probably via the intermediates (8 and 9). Treatment of 13 with alumina gives the hydroxy-epoxide (15), which is converted to the epoxy-diazepinone (16) by an alkali treatment. However, a similar treatment of 18 with bases gives only N-ethoxycarbonylaniline (19) and does not give any other characterized products.
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TAKEFUMI MOMOSE, KENICHI KANAI, TAKESHI NAKAMURA, YUKIKO KUNI
1977 Volume 25 Issue 10 Pages
2755-2760
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The photocyclization of 2, 3-dibenzylidenebutyrolactones (5) was investigated in association with the possible biogenetic pathway to natural naphthalide lignans in which 1-phenyl-2, 3-naphthalide types predominate over 4-phenyl-2, 3-naphthalide ones. The butyrolactones (5) were prepared via Stobbe condensation of benzylidenesuccinates (6) followed by the selective reduction of the resulting half esters (7) to hydroxy acids (8) and subsequent lactonization. and their cis, cis-configuration was assigned on the basis of comparative proton magnetic resonance (
1H-NMR) data. Irradiation of 5 afforded selectively β-apolignans (11) of the 1-phenyl-2, 3-naphthalide types irrespectively of the ring substituents, and none of the 4-phenyl-2, 3-naphthalide types was formed in the reaction.
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FUMINORI MASUGI, HIDEYUKI SANMA, TETSUYA NAKAMURA
1977 Volume 25 Issue 10 Pages
2761-2762
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The determination of the activity of succinate dehydrogenase-coenzyme Q reductase of leucocytes mitochondria has been studied by using 2, 6-dichlorophenolindophenol as an indicator. It was found that contaminating hemoglobin, disturbed the accurate estimation of the enzyme activity in the method previously reported. An improved assay method is presented.
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ODILE SIFFERT, MONIQUE PASQUET
1977 Volume 25 Issue 10 Pages
2763-2767
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Several new peptides of the general structure Pro-Leu-X-Pro have been synthesized, by the well-known procedures with proline in L- or D-form and with either glycine or sarcosine in the position of X-. These peptides act as competitive inhibitors of collagenase from Achromobacter iophagus.
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MASAYOSHI YAMAGUCHI, TAKEO YAMAMOTO
1977 Volume 25 Issue 10 Pages
2767-2769
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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A single intraperitoneal administration of insulin to intact and thyroparathyroidectomized rats caused a significant decrease of serum calcium at 10mU/100g body weight of the hormone, while it did not show any drop in serum glucose. Administration of 100mU/100g of insulin produced a significant decrease of both calcium and glucose in serum. The time course of serum calcium response to insulin is mimiced that of calcitonin with single injections. The present results indicate that insulin has a hypocalcemic effect in rats.
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TSUTOMU MIMURA, NORIO MUTO, HIROSHI TSUJIBO, NOBORU ONISHI, SHIGERU AO ...
1977 Volume 25 Issue 10 Pages
2770-2774
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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The inhibitory substance against gastric ulceration in pylorus-ligated rats was purified through extraction with 5% acetic acid-50% ethanol, fractionation with ethanol, isoelectric precipitation, DEAE-cellulose column chromatography, and gel filtration on Sephadex G-100 column from isoelectric precipitate if the 72 hr culture filtrate of Bacillus subtilis H IAM 1521, and it was named gastric ulcer inhibitory substance (GUIS). This substance reduced ulceration in pylorus-ligated rats by 84.2% at the dose of 5.0mg/kg, it also significantly repressed aspirin-induced gastric lesions under pylorus ligation at the same dose, but its activity was weak in stress-induced ulceration. It markedly decreased gastric juice volume, acidity, and peptic activity in pylorus-ligated rats when administered intraperitoneally at 5.0 mg/kg. This substance was a glycoprotein which showed homogenous patterns in various kinds of electrophoresis, and its isoelectric point was pH 4.5.
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TERUAKI TSUJIKAWA, YASUSHI NAKAGAWA, KAZUO TSUKAMURA, KATSUTADA MASUDA
1977 Volume 25 Issue 10 Pages
2775-2778
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Oudenone, a tyrosine hydroxylase inhibitor, and related analogues were obtained upon heating a mixture of 1, 3-cyclopentanediones and 2, 2-diethoxytetrahydrofurans.
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TOSHIO WATANABE, SADAMU KATAYAMA, YOSHIHIKO NAKASHITA, MASASHIGE YAMAU ...
1977 Volume 25 Issue 10 Pages
2778-2781
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Cycloalkenochromones (IV) were prepared from salicylaldehyde methoxymethyl ether and cycloalkanones via aldol condensation.
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ZENICHI HORII, EMIKO YONEDA, TETSUAKI TANAKA, CHUZO IWATA
1977 Volume 25 Issue 10 Pages
2782-2784
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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Ligularol and furanoeremophilane were converted into 6β-hydroxyeremophilenolide and eremophilenolide via photochemical oxidation
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YASAYOSHI YAMAGUCHI, TAKEO YAMAMOTO
1977 Volume 25 Issue 10 Pages
2785-2787
Published: October 25, 1977
Released on J-STAGE: March 31, 2008
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A single intraperitoneal injection of calcium chloride solution (2.0 mg Ca
2+/100 g body weight) markedly increased both calcium and glucose levels in serum of rats. The increase of both calcium and glucose levels in serum produced by the injection of calcium was significantly inhibited by prior administration of insulin (0.1 U/100 g). In contrary, the level of serum glucose elevated by the injection of calcium was not lowered by the simultaneous administration of insulin and calcitonin (80 MRC mU/100 g), while the serum calcium level was decreased additively. The administration of calcitonin alone to rats caused an increase in serum glucose and a decrease in serum levels. These results suggest that calcitonin has an insulin inhibitory effects not mediated through hypocalcemia in rats.
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