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TERUMI NAKAJIMA, TADASHI YASUHARA, VITTORIO ERSPAMER, GUILIANAFALCONIE ...
1980 Volume 28 Issue 3 Pages
689-695
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Biologically active peptides of the tachykinin and bombesin families occurring in the skin of the Australian leptodectylid frog Uperoleia rugosa were isolated in pure forms and their structures were determined. Uperolein-like peptide 1 was identified, as expected, as authentic uperolein ; uperolein-like peptide 2 was found to have the sequence Pyr-Ala-Asp-Pro-Lys-Thr-Phe-Tyr-Gly-Leu-Met-NH
2 and may be considered a Lys
5, Thr
6-physalaemin. Bombesin-like peptide 1, in its turn, was identified as Glu(OEt)
2-litorin, and bombesin-like peptide 2 as authentic litorin. Uperolein and litorin had previously been identified in Uperoleia rugosa and Litoria aurea, respectively ; the other two peptides are new. Glu(OEt)
2-litorin and Lys
5, Thr
6-physalaemin appear to have biological activities very similar to those of Glu(OMe)
2-litorin and physalaemin (or uperolein), respectively.
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AKIRA TAKAMURA, SHUNICHI NORO, TOMOKO MINOWA, MASUMI KOISHI
1980 Volume 28 Issue 3 Pages
696-701
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Using soya sterol (chemical composition by weight : β-sitosterol 56% ; campesterol 28% ; stigmasterol 4% ; sterol hydrocarbons and cholesterol 6% ; triterpene alcohols, keto-steroids and other steroid-like constituents 6%) and Span 85 as emulsifiers, with liquid paraffin as the dispersed phase in water, the effect of soya sterol and Span 85 on emulsion stability was evaluated in terms of the following five physicochemical parameters : (1) particle size, (2) degree of dispersion, (3) separation rate of dispersed droplets, (4) rheology of emulsion products, (5) sedimentation rate of dispersed droplets. An agitator and a homogenizer were used to produce the emulsions. The following results were obtained. (1) The particle size of emulsions prepared with soya sterol was larger than that with Span 85, and consequently, soya sterol is a less effective emulsifier than Span 85. (2) Nevertheless, soya sterol has stronger stabilizing action on emulsions than Span 85, and this effect become especially marked when emulsification was carried out with a homogenizer at a high shear rate.
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KENICHI OZAKI, YOSHIHISA YAMADA, TOYONARI OINE
1980 Volume 28 Issue 3 Pages
702-707
Published: March 25, 1980
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1-Phenyl-4(1H)-quinazolinones having various substituents at C-2 were synthesized and some of their reactions were examined. 1-Phenyl-2-substituted-4(1H)) quinazolinones (3) were synthesized in good yield by the reaction of 2-phenylaminobenzamide (1) with excess acid chloride under mild reaction conditions. The 2-chloroalkyl derivatives (3b-d) react with nucleophiles in a characteristic manner depending on the length of the alkyl chain. Treatment of the 2-chloromethyl derivative (3b) with nucleophiles gave 2-(substituted-methyl)-4(1H)-quinazolinones (4). Reaction of 2-chloroethyl derivative (3c) with morpholine or alcohols gave 2-(β-substituted-ethyl) derivatives (5-7) through the intermediate (8), which was identified by isolation. Allowing a chloroform solution of the 2-(γ-chloropropyl) derivative (3d) to stand afforded the 4-oxoquinazolinium salt (9a) quantitatively.
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MUNEKAZU IINUMA, SHIN MATSUURA, KOUSUKE KUSUDA
1980 Volume 28 Issue 3 Pages
708-716
Published: March 25, 1980
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The
13C-NMR spectra of 61 flavone derivatives were measured in dimethyl sulfoxide. By consideration of the chemical shifts of skeletal carbons, the parameters (α and β values) and correction factor (ο value) necessary for calculating their carbon shifts were deduced. The skeletal carbons of polysubstituted flavones and flavonols could easily be assigned by the use of these values and SCS of OMe or OH. The
13C-NMR spectra were confirmed to give useful information that could not be obtained from other spectral data. The data were applied for the structure elucidation of unknown polysubstituted flavones.
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MUNEKAZU IINUMA, SHIN MATSUURA, KAZUAKI KUROGOCHI, TSUGIO TANAKA
1980 Volume 28 Issue 3 Pages
717-722
Published: March 25, 1980
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Thirteen kinds of flavones, including two new flavones, were isolated from the fruit peel of Citrus reticulata BLANCO (Rutaceae) on the basis of thorough examination of the components in the chloroform extract of the peel. The structures of these flavones were confirmed by analysis of the spectral data and by structural conversion or total synthesis. β-Sitosterol, limonin, hesperidin, ferulic acid, and 5, 5'-oxydimethylene-bis(2-furaldehyde) were also isolated as components other than flavones. The multisubstituted flavones obtained were examined by gas-liquid chromatography, and may provide a good marker for chemotaxonomical studies of Citrus species.
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MASATOSHI YAMATO, TADATAKA ISHIKAWA, TOMOHISA NAGAMATSU, SHIN YOSHIKAW ...
1980 Volume 28 Issue 3 Pages
723-729
Published: March 25, 1980
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The reduction of 3, 4-dihydroisocoumarins (1, 3, 6, 11a, 11b, and 12b) having a hydroxyl group or acetoxyl group at the C
(8)-position adjacent to the lactone carbonyl group with lithium aluminum hydride gave novel products, 1, 8-dihydroxyisochromans (10a, 13, and 16a), in addition to 8-hydroxyisochromans (2, 8, and 14) and 2-(3-hydroxy-2-hydroxymethylphenyl)-ethanols (4, 9, and 15). The isochromans and 2-(2-hydroxymethylphenyl)-ethanols are known reduction products of 3, 4-dihydroisocoumarins lacking a C
(8)-hydroxyl group. In addition, 13 was obtained selectively in 50% yield by reduction of the magnesium chelate of 11a with lithium aluminum hydride. Similarly, 8-hydroxy-3-phenylisocoumarin (23a) and 8-acetoxy-3-phenylisocoumarin (23b) both gave 2-formyl-3-hydroxybenzyl phenyl ketone (24). Based on these results, a mechanism for the reduction of 8-hydroxy-3, 4-dihydroisocoumarins is proposed, as shown in Chart 3.
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TAKAO HAYAKAWA, TSUYOSHI TANIMOTO, JIRO KAWAMURA
1980 Volume 28 Issue 3 Pages
730-736
Published: March 25, 1980
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Kinetic measurements were made to investigate the interaction of 20β-hydroxysteroid dehydrogenase and a series of steroids with C-17 and/or C-21 hydroxyl groups, and the role of the region around C-17 and C-21 on the interaction of the reacting 20-oxo group with the catalytic site of the enzyme was considered. Substitution of a hydroxyl group for hydrogen at C-21 of 17-deoxy-steroid derivatives caused a significant decrease in the apparent V
max value (to about one-sixth to one-ninth), but a slight increase in the apparent K
m value (about 1.1- to 1.8-fold). The same change at C-21 of 17-hydroxy-steroid derivatives caused little or no decrease in the apparent V
max value, but an increase in the apparent K
m (about 1.4- to 1.8-fold) occurred which was similar to that with 17-deoxy-steroid derivatives. In 21-deoxy-11-deoxy-steroid derivatives, a 17α-hydroxyl substituent had little effect on the apparent K
m value (about 0.8- to 1.1-fold) and produced a slight decrease in the apparent V
max value (to about three-quarters to two-fifths). Introduction of a 17α-hydroxyl group into 21-deoxy-11-oxo-steroid derivatives led to a significant decrease in the apparent K
m value (to about one-seventh) and a moderate decrease in the apparent V
max value (to about five-sixths to one-half). Introduction of a 17α-hydroxyl group into 21-hydroxy-steroid derivatives caused the apparent V
max value to increase by about 1.8- to 11-fold, but caused little or no decrease in the apparent K
m value. These results suggest that the hydroxyl group at the 21- or 17α-position directly restricted the conformation and the orientation of the 20-oxo group towards the catalytic site of the enzyme and influenced the hydrogen transfer stage in the catalytic process, and also that, of the substituents at the 21- and 17α-positions, the latter may preferentially affect the reaction efficiency of the 20-oxo group. The presence of an oxo group at C-11 had an indirect influence on the effects of the substituents at the 21- and 17α-positions. The optimum orientation of the 20-oxo group for the catalytic reaction may occur in 21-deoxy-17-deoxy-11-deoxy-steroid derivatives. In an ideal ternary complex, the 20-oxo group of the steroid may project towards the β-face of the steroid ring and the conformation between the 20-oxo group and α-hydrogen of C-17 is nearly staggered, while that between C-21 and the α-hydrogen of C-17, looking along the C-17 to C-20 axis, is in a skew form ; the 20-oxo group is orientated rather far from the methyl group at the β-position of C-13 and more towards the β-chain of C-16.
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KUNIAKI TERATO, JUNKO OGINO, SHIZUKO OHYA, KAZUYO NOGUCHI, TSUNEO NAKA ...
1980 Volume 28 Issue 3 Pages
737-744
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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An assay method for secretin in crude preparations containing unknown amounts of pancreozymin has been developed, using rats. For several hours after urethan injection there was a marked fall in the volume of pancreatic juice correlated with the decrease of protein output of rat pancreas stimulated with secretin-pancreozymin mixture, then both reached steady-state levels. In this condition, where the sensitivity to pancreozymin was reduced, the pancreatic response was linearly related to the logarithm of the dose of crude or partially purified secretin in the ranges of 0.05-0.4 and 0.5-4.0 Crick, Harper and Raper (CHR) units, respectively. Within this range, the activity of crude secretin could be determined by four- and threepoint assay procedures with an error of 10 percent or less. The validity of the assay values for the crude preparations using the three-point design was confirmed by the recovery of secretin activity as highly purified secretin (free from pancreozymin) from the crude materials.
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HIDEAKI UMEYAMA, SETSUKO NAKAGAWA, TOMOKO NOMOTO, IKUO MORIGUCHI
1980 Volume 28 Issue 3 Pages
745-754
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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The inclusion complex of NH
4+ with tetranactin increases the fluxes of ions across thin lipid membranes. When NH
4+ is inserted into the ionophore of tetranactin, the conformation changes greatly ; this structural change is called an "induced fit." When the conformation change of tetranactin is induced by the approach of NH
4+, the four ether oxygens of the tetrahydrofuran rings and the four carbonyl oxygens of the ester groups function to include NH
4+ in the molecule. The ether oxygens rotate inwards to hold NH
4+ inside tetranactin, and the carbonyl oxygens rotate inwards to prevent NH
4+ from escaping. The four ether oxygens form linear hydrogen bonds with NH
4+. Although the four carbonyl oxygens approach NH
4+ at distances similar to those of the four ether oxygens, the carbonyl oxygens do not form linear hydrogen bonds with NH
4+. In order to clarify the induced fit mechanism of the ionophore, in this paper, the inclusion complex of NH
4+ with tetranactin was studied with regard to the arrangement of NH
4+ in the tetranactin molecule from a quantum-chemical point of view. Since tetranactin is too large for double zeta ab initio SCF calculations, functional groups which have large contributions to the insertion of NH
4+ were selected as a model for the tetranactin ; the model consisted of four HCHO molecules and four H
2O molecules. The model was in good accord with the actual result, and thus appears to be appropriate. Tetranactin is composed of four homonactinic acid moieties, and the interaction energy between each of them and NH
4+ is significant for the arrangement of NH
4+. The interaction energy between NH
4+ and the four ether groups was -73.2 kcal/mol, and the interaction energy between NH
4+ and the four carbonyl groups was -39.4 kcal/mol. The interaction energy between NH
4+ and the ether groups was thus about 1.9 times larger than that between NH
4+ and the ester groups. The interaction energy between NH
4+ and the eight ether and ester groups was -109.0 kcal/mol. From the results of geometry optimizations, the interaction energy between NH
4+ and CH
3OCH
3 was larger than that between NH
4+ and HCOOH by 5.8 kcal/mol due to the electrostatic interaction energy. Therefore, even though the four carbonyl groups may move to accommodate NH
4+ in tetranactin, the four ether groups of tetranactin will interact more strongly with NH
4+ than the four carbonyl groups, and NH
4+ will orient to the ether groups. Moreover, when perturbation of the ionophore by the rotation of NH
4+ is neglected, the rotational inhibition energy of NH
4+ in tetranactin was calculated to be 9.8 kcal/mol ; thus, NH
4+ is expected to orient to the four ether oxygens.
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KAZUMASA HIRAUCHI, AKIKO FUJISHITA
1980 Volume 28 Issue 3 Pages
755-760
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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4-Homosulfanilamide was found to react with 2-chloro-5-nitropyridine to form 5-nitro-2-(p-sulfamoylbenzylamino)pyridine, which was strongly phosphorescent in ethanol containing 0.1% (v/v) dimethyl sulfoxide. This observation was used as the basis for a procedure to determine micro amounts of 4-homosulfanilamide, and the method was also applied to the determination of 4-homosulfanilamide added to the rat plasma. A linear relationship between the phosphorescence intensity and the amine concentration was observed in the range of 4×10
-7-2×10
-5M.
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NORIO SUZUKI
1980 Volume 28 Issue 3 Pages
761-768
Published: March 25, 1980
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In order to search for compounds with higher activity than thiazolo [5, 4-b], imidazo-[4, 5-b] and triazolo [4, 5-b] [1, 8] naphthyridine derivatives against Ps. aeruginosa, we synthesized some heterocyclic condensed 1, 8-naphthyridine derivatives by using bifunctional 6, 7-disubstituted 1, 8-naphthyridine as a starting material. Thiadiazolo [5, 4-b] and oxazolo [5, 4-b] [1, 8] naphthyridine derivatives (3) and (5) were prepared by hydrolysis of the 6-amino-7-chloro-3-ester (1) with sodium hydroxide or sodium hydrosulfide, followed by cyclization with acetic anhydride or sodium nitrite. Pyrazolo [3, 4-b] and isothiazolo [5, 4-b] [1, 8] naphthyridine derivatives (12) and (14) were synthesized by ring cyclization of the 7-chloro-6-formyl-3-ester (10) with methyl hydrazine or ethanolic ammonia in the presence of sulfur, followed by hydrolysis. Thieno and furo [2, 3-b] [1, 8] naphthyridine derivatives (20) and (31) were prepared through a series of reaction steps, e.g. diazotization, reduction of the nitrile ester (7) or (24), ring cyclization by means of ethyl mercaptoacetate or ethyl bromomalonate, hydrolysis and decarboxylation. The compounds obtained were tested for antimicrobial activities in vitro. 8-Ethyl-5, 8-dihydro-5-oxothieno [2, 3-b] [1, 8] naphthyridine-6-carboxylic acid (20) exhibited the highest activities among these compounds against many gram-negative bacteria, including Ps. aeruginosa, and against gram-positive bacteria.
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AKIRA TAKAMIZAWA, HIROSHI HARADA
1980 Volume 28 Issue 3 Pages
769-778
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Hydrogen peroxide oxidation of 4-(4-amino-2-methylpyrimidin-5-yl) methyl-6-(2-hydroxyethyl)-2-(2-methoxyphenyl)-4-methyl-2, 3-dihydro-4H-1, 4-thiazin-3-one (1c) gave N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[1-(2-oxido-1, 2-oxathiolan-3-yliden)ethyl] (2-methoxyphenyl)oxalamide (3b) and 2-oxido-1, 2-oxathiolane-3-spiro-3'-[1'-(4-amino-2-methylpyrimidin-5-yl)methyl-4'-hydroxy-2'-methylene-4'-(2-methoxyphenyl)-tetrahydropyrrol-5'-one] (6). The former product (3b) was transformed into another product (6) under oxidative reaction conditions and 6 led to the known 1-(4-amino-2-methylpyrimidin-5-yl)methyl-4-hydroxy-3-(2-hydroxyethyl)-4-(2-methoxyphenyl)-2-methyl-Δ
2-pyrrolin-5-one (4) and 2-aza-2-(4-amino-2-methylpyrimidin-5-yl)methyl-4-hydroxy-4-(2-methoxyphenyl)-1-methyl-8-oxabicyclo [3.3.0] octan-3-one (5) on acid or alkali treatment. On the other hand, an oxalamide (3d) having a 2-anisyl substituent was recovered under the same reaction conditions. The same reaction with 2-aryl-4-benzyl-2, 3-dihydro-4H-1, 4-benzothiazin-3-ones (12a-c) afforded 2-aryl-4-benzyl-2-hydroxy-2, 3-dihydro-4H-1, 4-benzothiazin-3-ones (13a-c), bis-(2-aryloxalylaminophenyl)-1, 1'-disulfide (14a-b) and 2-aryl-4-benzyl-3-oxo-2, 3-dihydro-4H-1, 4-benzothiazine-1, 1-dioxide (15a-c), while 4-benzyl-2-methyl-2, 3-dihydro-4H-1, 4-benzothiazine-1, 3-dioxide (16b) was mainly obtained in the oxidation of the 2-methyl derivative (12d), which was converted into 4-benzyl-2-hydroxy-2-methyl-2, 3-dihydro-4H-1, 4-benzothiazin-3-oxide (13d) via a Pummerer-type rearrangement. The reaction mechanism is discussed.
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TOHORU TATSUHARA, FUMIE TABUCHI
1980 Volume 28 Issue 3 Pages
779-782
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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An analytical method for meclofenoxate and its degradation products was established by high performance liquid chromatography. The chromatographic conditions were as follows : column, μ-bondapak C
18 ; mobile phase, MeOH-0.1% ammonium carbonate of pH 3.1 ; flow rate, 2.0 ml/min ; spectrophotometric detection at 227 nm. The mobile phase was found to be suitable for use as an extracting solvent for pharmaceutical preparations, since it caused almost no degradation of the sample, which has been reported to be very susceptible to hydrolysis.
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AKIHIKO ISHIDA, SHIGEYOSHI SAIJO, JUNICHI HIMIZU
1980 Volume 28 Issue 3 Pages
783-788
Published: March 25, 1980
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The decarboxylation of various 1-substituted-3, 7-dioxabicyclo[3.3.0]octane-2, 8-diones (2b-j) was in vestigated. On treatment with potassium acetate in aqueous pyridine under reflux, all the compounds (2b-j) examined were decarboxylated in high yields to give the corresponding trans-3-hydroxymethyl-4-butanolides (3b-j). The synthesis of 10-oxa-11-deoxyprostaglandin E
2 (1a) from the compounds 3i and 3j is also described. The Moffatt oxidation of 3i and the Wittig reaction of the resulting aldehyde (6a) with dimethyl 2-oxoheptylphosphonate gave an enone (7a), which was converted into 10-oxa-11-deoxyprostaglandin E
2 methyl ester (8a) and the C
15-epimer (9a) by NaBH
4 reduction. Hydrolysis and subsequent relactonization of 8a gave 1a in 88% yield. A similar treatment of 9a gave 1b in 87% yield. Using a similar sequence of reactions, 1a and 1b were also prepared from the nitrile analog 3j via 8b and 9b.
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MOTOWO IZAWA, KONOMI HAIBARA, MITSUKO ASAI
1980 Volume 28 Issue 3 Pages
789-794
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Ansamitocins and related compounds were isolated from the culture broth of Nocardia sp. 1) The total amount of the antibiotics, after extraction with ethyl acetate from the culture broth, was determined by high-performance liquid chromatography on a μ Porasil column with a solvent mixture of methylene chloride-methanol (20 : 1). 2) Each component in the mixture was quantitatively analyzed on a μ Bondapak column with 69% aqueous methanol. 3) Preparative separation of up to 5 g per cartridge column was carried out in good yield (90%) using a PrepLC/system 500 (Waters) and a column packing of Kieselgel 60 (E. Merck). The purities of the ASM obtained were above 95%.
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TOSHIO KINOSHITA, TADANORI ONOUE, MITSUAKI WATANABE, SUNAO FURUKAWA
1980 Volume 28 Issue 3 Pages
795-804
Published: March 25, 1980
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The reaction of dimethylsulfonium acetylcarbamoylmethylide (Ia) with quinoline 1-oxide in the presence of acetyl chloride in N, N-dimethylformamide gave 6-methyl-5-methylthio-2-[2(1H)-quinolylidene]methyl-1, 3-oxazin-4-one (IIIa) and 6-methyl-5-methylthio-2-[2(1H))quinolylidene-2-quinolyl]methyl-1, 3-oxazin-4-one (IVa). The structures of IIIa and IVa were established by chemical and spectral analysis. This is a new type of reaction of stable sulfur ylides.
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NORIAKI FUNASAKI, AKIRA MURATA
1980 Volume 28 Issue 3 Pages
805-814
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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The first-order rate constants for the alkaline hydrolysis of ethyl benzoate and ethyl p-nitro- and p-aminobenzoates (benzocaine), catalyzed by CTAB, a cationic surfactant, were measured at 25°in the presence of sodium hydroxide and sodium bromide. Although the alkaline hydrolysis of esters is generally accelerated by cationic micelles, that of the three benzoates tended to be inhibited by CTAB micelles under the following conditions : (i) at high CTAB concentrations, (ii) at high concentrations of sodium hydroxide, (iii) at high concentrations of an added salt (including buffer components), (iv) at high ester concentrations, and (v) for compounds possessing a small value of the Hammett substituent constant. These effects were explained quantitatively on the basis of a theory in which the total counterion concentration is assumed to remain constant regardless of the concentrations of CTAB, sodium bromide, and sodium hydroxide, and in which the association constant for a CTAB micelle and an ester, the degree of counterion binding to CTAB micelles, the ion-exchange constant, and a relative rate constant are taken as parameters.
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YUKIO KUBOTA, SAKIKO NAKAJIMA, TAKASHI SONOBE, HIROITSU KAWATA, YOSHIN ...
1980 Volume 28 Issue 3 Pages
815-823
Published: March 25, 1980
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The aims of the present investigation were to compare the dissolution properties of dimemorfan phosphate and dimemorfan and to control the dissolution of dimemorfan species, which are pharmacologically equivalent, by using suitable mixtures of dimemorfan phosphate and dimemorfan. The solubility of dimemorfan was studied in solutions of various pH values. It was almost constant at low pH, reached a maximum at pH 6.6, and decreased significantly with further increase of pH. Dissolution rates were determined in solutions of various pH values. Dissolution rate of dimemorfan phosphate increased gradually with increase of pH of the dissolution medium, whereas that of dimemorfan decreased. It is suggested that in the case of dimemorfan dissolution, the pH value of the saturated layer is influenced profoundly by the nature of the dimemorfan species, though the effect is small in the case of dimemorfan phosphate because of the existence of phosphate ions in the compound. Based on an analysis of the dissolution properties of dimemorfan species in solutions of different pH values, a method for controlling the release of dimemorfan species was established by the use of mixtures of dimemorfan and dimemorfan phosphate.
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MASASHI TOMODA, NORIKO SATOH, KAZUYO SHIMADA
1980 Volume 28 Issue 3 Pages
824-830
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Partial acid hydrolysis of Althaea-mucilage O, a representative mucous polysaccharide isolated from the roots of Althaea officinalis L., led to the isolation of five oligosaccharides. Analysis of their components, as well as reduction and methylation, and partial degradation studies showed that these oligosaccharides are O-α-(D-galactopyranosyluronic acid)-(1→2)-L-rhamnopyranose, O-β-(D-glucopyranosyluronic acid)-(1→3)-O-α-(D-galactopyranosyluronic acid)-(1→2)-L-rhamnopyranose, and the hexasaccharide, the nonasaccharide, and the dodecasaccharide composed of a repeating unit having the structure of the trisaccharide through position 4 of the D-galacturonic acid residue. The polysaccharide was also subjected to chromium trioxide oxidation, and to controlled Smith degradation. The configuration and the mode of branching were determined. The structural features of the mucilage are discussed.
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SHINGO YASUDA, MIYOJI HANAOKA, YOSHIO ARATA
1980 Volume 28 Issue 3 Pages
831-836
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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A new stereoselective synthesis of (±)-7-epideoxynupharidine (1), the most stable quinolizidine-type Nuphar alkaloid, is described. Condensation of 2-ethyl-5-methylpyridine (5) with acetonitrile, followed by ketalization, gave the ketal (13), which was hydrogenated to afford the piperidine (14). Deketalization of 14 afforded the aminoketone (15). Condensation of 15 with 3-furylaldehyde afforded four quinolizidin-2-ones (8, 16, 17, and 18) in 14, 45, 1, and 3% yields, respectively. The cis-quinolizidines (16 and 18) were isomerized to the trans-quinolizidines (8 and 17, respectively). Wolff-Kishner reduction of 8 afforded (±)-7-epideoxynupharidine (1) (45%) and (±)-1-epi-7-epideoxynupharidine (2) (15%). Similar reduction of 17 provided (±)-deoxynupharidine (3) (33%) and (±)-1-epideoxynupharidine (4) (14%).
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KEIKO MURAKOSO, YOKO TSUMURA, KEIKO NAKAO, SHOHEI KAGAWA, AKIRA MATSUO ...
1980 Volume 28 Issue 3 Pages
837-842
Published: March 25, 1980
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The effect of alloxan on cultured rat pancreatic endocrine cells was investigated by following changes in the incorporation of D-[U-
14C]glucose into proteins (chloroform/methanol-insoluble fraction) and lipids (chloroform/methanol-soluble fraction). Cultured cells exposed to either alloxan or alloxan plus D-glucose anomers (16.7 mM) at 37°for 5 min were incubated in a medium containing D-[U-
14C]glucose at 37°for 60 min. Alloxan at concentrations of 1.25 and 6.25 mM produced inhibitory effects on incorporation into proteins but had no effect on incorporation into lipids. Incorporation into both proteins and lipids was inhibited by 31.2 mM alloxan. The combination of 1.25 mM alloxan plus 16.7 mM D-glucose anomers synergistically reinforced the inhibitory effect of alloxan on the incorporation of labeled glucose into proteins and lipids. In addition, the action of alloxan was more effective in the presence of the β anomer than the α anomer. SDS-polyacrylamide gel electrophoresis of cells labeled with D-[U-
14C]glucose indicated the involvement of cell components having molecular weights of more than 200000, 120000, 52000 and 20000. In conclusion, the present data indicate that alloxan inhibits the incorporation of D-[U-
14C]glucose into proteins and lipids in cultured pancreatic endocrine cells and that the β anomer of D-glucose reinforces the action of alloxan to a greater extent than the α anomer.
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TAKAYASU KITAGAWA, YOKO ADACHI, EIZO HIRAI
1980 Volume 28 Issue 3 Pages
843-849
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Ion pair extraction of a basic drug (trimethoprim) with sulfonphthaleins (BTB, BCG and BPB) was examined on the basis of equation (1). [numerical formula] The molar ratio, Q, of the extracted ion pair (Q=[BH
+IH
-]
org/(C
B-[BH
+IH
-]
org)) was represented as a function of the hydrogen ion activity ((α
H)
W) and the concentration of the sulfonphthalein monoanion ([IH
-]
W). The extraction constant, K
ex, of the equilibrium (2) was estimated from equation (1). [numerical formula] The log K
ex values of TMP-BTB were found to be 5.26, 7.08 and 8.10 in benzene-H
2O, 1, 2-dichloroethane-H
2O and CHCl
3-H
2O systems, respectively. The log K
ex values of TMP-BCG and TMP-BPB in the 1, 2-dichloroethane-H
2O system were found to be 5.89 and 4.95, respectively. The effect of pH on the ion pair extraction is discussed in terms of equation (1). The pH values suitable for the assay of TMP with BTB by means of ion pair extraction were found to be in the range of 4 to 6.
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SANSEI NISHIBE, MARIKO CHIBA, AKIYO SAKUSHIMA, SUEO HISADA, SAKAE YAMA ...
1980 Volume 28 Issue 3 Pages
850-860
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Attempts were made to introduce an alcoholic hydroxyl group stereospecifically at the C-5 or C-6 position of 2, 3-dibenzylbutyrolactone lignans with lead tetraacetate and osmic acid as oxidizing agents. 5-Acetoxyarctigenin monoacetate (III) was obtained from arctigenin monoacetate (II), 5-acetoxyisoarctigenin monoacetate (XIII) from isoarctigenin monoacetate (XII) and 5-acetoxytrachelogenin diacetate (XXIII) from trachelogenin diacetate (XXII) by oxidation with lead tetraacetate in acetic acid. 6-Hydroxyisomethyltrachelogenin (XXXII) was obtained from 3-(3, 4-dimethoxybenzyl)-2-(3, 4-dimethoxybenzylidene) butyrolactone (XXXI) by oxidation with osmic acid. The
13C-NMR spectra of these oxidation products and analogs are discussed with regard to the differences of the chemical shifts resulting from changes in the substituents and the stereochemistry of the 2, 3-dibenzylbutyrolactone skeleton.
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MIKIO YAMAZAKI, KUMIKO SUZUKI, HARUHIRO FUJIMOTO, TOSHIYUKI AKIYAMA, U ...
1980 Volume 28 Issue 3 Pages
861-865
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Fumitremorgin B (2), isolated from Aspergillus fumigatus together with fumitremorgin A (1), caused severe tremors and convulsion in experimental animals. The structure of fumitremorgin B was determined from the spectral data. The stereochemistry, including the absolute configuration, was determined by X-ray analysis and comparison of the ORD of proline obtained from this compound with that of authentic L-(-)-proline.
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MASAYUKI ONDA, HIROKO YAMAGUCHI, YOSHIHIRO HARIGAYA
1980 Volume 28 Issue 3 Pages
866-870
Published: March 25, 1980
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Photolysis of dihydroisoquinoline (2) in the presence of nitrosobenzene gives the epoxyimine (10), sodium borohydride reduction of which affords the aniline (14). Reaction of the dehydro compound (17) derived from 14 with performic acid followed by hydrolysis provides the diol (20). Hydrogenolysis of 20 over a palladium catalyst affords the corynoline analog (7). All compounds are formed under strictly stereoselective control.
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HIDEKO KAWAKI, YUKO OKAZAKI, HIDEAKI FUJIWARA, YOSHIO SASAKI
1980 Volume 28 Issue 3 Pages
871-875
Published: March 25, 1980
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The enthalpy and entropy of the association between tris(dipivalomethanato)europium and pyridine bases or aliphatic alcohols were determined in CCl
4. The parameters of the pyridine bases are comparable with those for the reactions of pyridine base+MeI reported Brown et al. This supports the validity of our results and suggests that the two systems have analogous modes of interaction in solution. The K
1 and Δ
1 values of the pyridine base+Eu(DPM)
3 series depend on ΔH and ΔS. For aliphatic alcohols, on the other hand, there is a clear correlation between K
1 and steric factors.
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AKIRA MATSUDA, KAORI NIIZUMA, TOHRU UEDA
1980 Volume 28 Issue 3 Pages
876-881
Published: March 25, 1980
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Treatment of 2', 3'-O-isopropylidene-5'-oxo-8, 5'-cycloadenosine with dimethyloxosulfonium methylide followed by hydrogenation afforded the diastereomeric pairs of 5'-methyl-5'-deoxy-8, 5'-cycloadenosine and 5'-hydroxymethyl-5'-deoxy-8, 5'-cycloadenosine. The configurations at the 5'-positions of these 8, 5'-cycloadenosines were determined by nuclear magnetic resonance (NMR) measurements. The Wittig reactions of the 5'-oxo-8, 5'-cycloadenosine with methoxymethylenetriphenylphosphorane, methylthiomethylenetriphenylphosphorane, and ethyl (dimethylsulfuranylidene) acetate afforded the corresponding 5'-substituted derivatives. The action of ethoxycarbonylmethylenetriphenylphosphorane with the 5'-oxo-8, 5'-cycloadenosine afforded the 5'-ethoxycarbonylmethylene-8, 5'-cycloadenosine, which was converted to 5'-hydroxyethyl-5'-deoxy-8, 5'-cycloadenosine by reduction with LiBH
4 followed by deacetonation. The 5'(R)- and 5'(S)-diastereomers of the 5'-hydroxyethyl derivative were separated and identified by NMR analysis. The circular dichroism (CD) spectra of the 5'-substituted-8, 5'-cycloadenosines showed that the diastereomers having the substituent at the trans-gauche position around the C
4'-C
5' bond gave strong negative CD bonds, whereas the diastereomers with the 5'-substitutent at the gauche-trans position exhibited positive bands.
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HARUAKI YAJIMA, JUN KANAKI, SUSUMU FUNAKOSHI, YUKO HIRAI, TERUMI NAKAJ ...
1980 Volume 28 Issue 3 Pages
882-886
Published: March 25, 1980
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The tetradecapeptide amide venom, mastoparan X, isolated from the Japanese hornet (Vespa xanthoptera), was synthesized by the methanesulfonic acid deprotecting procedure, employing m-cresol as a cation scavenger.
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CHIEKO KITADA, YASUKO ASHIDA, YOSHITAKA MAKI, MASAHIKO FUJINO, YUKO HI ...
1980 Volume 28 Issue 3 Pages
887-892
Published: March 25, 1980
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Granuliberin-R and various fragment peptides were synthesized and their histaminereleasing activities were examined. The relative potencies of granuliberin-R, H-Phe-Gly-Phe-Leu-Pro-Ile-Tyr-Arg-Arg-Pro-Ala-Ser-NH
2, as liberators of histamine from mast cells are very similar to those of substance P and bradykinin. Studies on the histamine-releasing activity of various fragment peptides of granuliberin-R showed that a 4-amino acid central sequence, -Ile-Tyr-Arg-Arg-, is the minimum requirement for the releasing action of this frog skin peptide.
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MASANORI YONAHA, YUKO OHBAYASHI, NAHOKO NOTO, EMIKO ITOH, MITSURU UCHI ...
1980 Volume 28 Issue 3 Pages
893-899
Published: March 25, 1980
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The effects of heavy metals, especially chromium, on lipid peroxidation in rat liver microsomes were studied. Lipid peroxidation was determined as thiobarbituric acidreacting materials. At lower concentrations in the range of 1-100μM, both hexavalent and trivalent chromium inhibited lipid peroxidation induced by ascorbate or NADPH in microsomes. In the presence of ascorbate, the inhibitions decreased on treatment with sulfhydryl reagents and were partly overcome by the addition of tartaric acid. It is suggested that chromium, presumably in the trivalent form, may bind with sulfhydryl groups of protein, resulting in the inhibition of lipid peroxidation. In the presence of NADPH, hexavalent chromium showed very potent inhibition. Hexavalent and trivalent chromium did not inhibit the electron-transport system in microsomes. The hexavalent form may act as a radical scavenger, since it strongly inhibited carbon tetrachloride-stimulated lipid peroxidation, could reduce 2, 2'-diphenyl-β-picrylhydrazyl to some extent in the presence of a reducing agent such as ethanol, and inhibited NADPH-induced peroxidation markedly in the presence of sulfhydryl compounds. Above 1 mM, hexavalent chromium caused lipid peroxide formation in microsomes, apparently not associated with iron, while trivalent chromium showed an inhibitory effect.
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SHUNJI NARUTO, OSAMU YONEMITSU
1980 Volume 28 Issue 3 Pages
900-909
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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On irradiation in 50% aqueous ethanol, the N-chloroacetyl derivatives of seven isomeric indolylethylamines gave the corresponding azocinoindole derivatives through photocyclization at the ortho and peri positions. Quantum yields for product formation with 2537 Å light showed the relative reactivity at each position of the indole ring to be in the order 3>6, 4>7, 2>5>1. In order to identify the reactive intermediary species and to establish the mechanism of the photocyclizations, frontier electron densities of several species of indole were calculated by CNDO/2 and INDO. The quantum yields for product formation from 1-substituted indole derivatives correlated fairly well (correlation coefficient r=0.82) with the singly occupied molecular orbitals (SOMO) electron densities (ED) of the 1-methylindole radical cation, but there was a better correlation (r=0.90) between the quantum yields for product formation from 1-unsubstituted compounds and the SOMO-ED of the indole-1-radical. These results show that the mechanism of the photocyclization of N-chloroacetylindolylethylamines involves both indole radical cations and indole-1-radicals as reactive intermediary species.
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HIDENOBU OHMORI, SHIRO NAKAI, MASAHIRO SEKIGUCHI, MASAICHIRO MASUI
1980 Volume 28 Issue 3 Pages
910-915
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Controlled potential electrolysis of triphenylphosphine in acetonitrile containing various primary alcohols and dialkyldisulfides resulted in the formation of the corresponding alkoxy and alkylthio triphenylphosphonium salts, [Ph
3P
+-X] [ClO
4-]. Compounds with X=OMe, OEt, OPr
n, SMe, SEt, and SPr
n were isolated. The alkoxy derivatives reacted with imidazole and thiophenol under mild conditions to give the corresponding N- and S-alkylated products quantitatively.
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SHUNJI SAKAMOTO, KEIJIRO SAMEJIMA
1980 Volume 28 Issue 3 Pages
916-919
Published: March 25, 1980
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Anti-2, 3-trimethylene-4-quinazolone antibody was prepared from the sera of two rabbits immunized with an antigen which was a conjugate of 6-(β-carboxypropionyl)-amino-2, 3-trimethylene-4-quinazolone and bovine serum albumin in a molar ratio of approximately 20 to 1. Specific affinity of the antibody for 2, 3-trimethylene-4-quinazolone was confirmed by comparison of the affinities for thirteen structurally related compounds.
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YOSHISUKE TSUDA, TETSUJI NUNOZAWA, KEIICHI NITTA, YUZURU YAMAMOTO
1980 Volume 28 Issue 3 Pages
920-925
Published: March 25, 1980
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The structures, including stereochemistries, of two fungal metabolites, terremutin hydrate and (-)-terredionol, were shown to be [4R, 5s, 6S]-4, 5, 6-trihydroxy-2-methylcyclohexane-1, 3-dione (III) and [4R, 6R]-(-)-4, 6-dihydroxy-2-methylcyclohexane-1, 3-dione (IV) by correlating them with xylitol and [2R, 4R]-(-)-pentane-1, 2, 4, 5-tetrol, respectively.
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KOUKI KITAGAWA, KUNIAKI KITADE, YOSHIAKI KISO, TADASHI AKITA, SUSUMU F ...
1980 Volume 28 Issue 3 Pages
926-931
Published: March 25, 1980
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The chemical behavior of N
im-p-methoxybenzenesulfonylhistidine, His (MBS), was examined. This new N
im-protecting group was removable by HF or N-hydroxybenzotriazole, like the N
im-Tos group, but was more acid-stable than the Tos group with methanesulfonic acid or HBr. The N
im-MBS group was stable to treatment with trifluoroacetic acid in the presence of anisole, but was found to be cleaved smoothly by the same acid in the presence of dimethylsulfide at room temperature within an hour. The N
im-Tos group was also removable under similar conditions, but at a somewhat lower rate.
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KIKUKO KAYASUGA-MIKADO, TERUKO HASHIMOTO, TOMOE NEGISHI, KAZUO NEGISHI ...
1980 Volume 28 Issue 3 Pages
932-938
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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Bromoacetaldehyde reacted with adenosine 5'-phosphate and cytidine more rapidly than chloroacetaldehyde to give 1, N
6-ethenoadenosine 5'-phosphate and 3, N
4-ethenocytidine, respectively. The pH-dependence of the rates of these reactions was similar to that of the chloroacetaldehyde modifications reported in the literature ; i.e. the reactions proceed smoothly in the pH range of 5 to 7. When applied to polynucleotides, bromoacetaldehyde reacted with adenine and cytosine residues located in single-stranded regions but not with those in double-stranded regions. Guanosine 5'-phosphate reacted with bromoacetaldehyde at pH 7 but only very slowly at pH 5. Bromoacetaldehyde may be useful as a more reactive subtitute for chloroacetaldehyde. Bromoacetaldehyde showed little mutagenic activity when assayed on Salmonella typhymurium TA 100.
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SUSUMU SHIBUYA, TOHRU UEDA
1980 Volume 28 Issue 3 Pages
939-946
Published: March 25, 1980
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The synthesis of S- and N-cyclouridines, which are "anti"-fixed cyclonucleosides, is described. Bromination of S
2, 2'-cyclo-2-thiouridine afforded the 5-bromo derivative. Cleavage of the S
2, 2'-cyclo linkage of the 5-bromo derivative with methoxide resulted in the formation of S
6, 2'-cyclo-2-O-methyluridine by intramolecular conversion of the S
2, 2'-linkage to an S
6, 2'-linkage, and this was further converted to the corresponding S
6, 2'-cyclo derivatives of uridine, isocytidine and 2-thouridine. Similarly, 2', 3'-O-isopropylidene-S
2, 5'-cyclo-2-thiouridine was converted to the 2', 3'-O-isopropylidene-S
6, 5'-cyclo derivatives of uridine, isocytidine, and 2-thiouridine. 6-Methylaminouridine was cyclized by treatment with diphenyl carbonate to N
6, 2'-cyclo-6-methylaminouridine. Cyclization with triphenylphosphine and diethyl azodicarboxylate gave the N
6, 5'-cyclo derivative of 6-methylaminouridine.
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YASUYUKI TSUDA, MOTOKO KANKE, ISAO MIYACHI, KAORU MAENO, KEIJI SEKIGUC ...
1980 Volume 28 Issue 3 Pages
947-955
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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It was confirmed that chloramphenicol and chloramphenicol palmitate form NH
3 adducts with combining ratios of 1 : 2 (chloramphenicol : NH
3), and 1 : 2 and 1 : 1 (chloramphenicol palmitate : NH
3). The thermal and physico-chemical properties of their NH
3 adducts and the recovered chemicals were investigated by differential scanning calorimetry, infrared spectroscopy, X-ray diffractometry, and scanning electron microscopy. Elimination of NH
3 from the adducts of chloramphenicol and chloramphenicol palmitate proceeded readily at normal temperatures and pressure to yield very fine particles of the original chemicals. Further, the effect of repeating the process of sorption and desorption of NH
3 on particle size was investigated in the case of chloramphenicol palmitate by the gas adsorption method. Two or more repetitions of the process produced a significant increase in specific surface area.
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SYOICHI SHIROTAKE
1980 Volume 28 Issue 3 Pages
956-963
Published: March 25, 1980
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New 2 : 1 cytosine-CaCl
2 and 1 : 1 cytosine-CaCl
2 complexes were obtained from 70% ethanol and water solutions, respectively. The infrared and proton magnetic resonance spectra of the complexes were characterized in comparison with those of many cytosinemetal complexes. On the basis of these data, it is suggested that calcium coordinates with the N (3) and C (2)=O sites of cytosine in the cytosine-CaCl
2 complexes.
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ATSUSHI NUMATA, KAZUKO HOKIMOTO, HIDEO YAMAGUCHI
1980 Volume 28 Issue 3 Pages
964-965
Published: March 25, 1980
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C-Glycosylflavones were isolated from leaf material of Lespedeza cuneata. Isovitexin, isoorientin, vicenin-2 and lucenin-2 were identified.
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FUJIO KAMETANI, YASUKO SUMI, IKUKO KONO
1980 Volume 28 Issue 3 Pages
966-968
Published: March 25, 1980
Released on J-STAGE: March 31, 2008
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To evaluate the substituent effect, the binding of p-toluenesulfonyl-n-alkylureas to bovine serum albumin was studied by equilibrium dialysis and fluorescence titration. The binding constants obtained by fluorescence titration were nearly equal to the geometric means of the primary and secondary binding constants obtained by equilibrium dialysis. The binding constants of p-toluenesulfonyl-n-butylurea were about ten times greater than those of the other compounds tested.
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YURIKO KATO, MAYUMI KOHKETSU
1980 Volume 28 Issue 3 Pages
968-972
Published: March 25, 1980
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A method for the microcrystallization of amobarbital was developed. This method consists of the following procedures : (1) dissolution of amobarbital (J.P. IX) in a hot solvent such as a glycol or glycol derivative, (2) pouring this solution into cold water (3°) while stirring to precipitate microcrystals, and (3) collection and drying of the precipitated microcrystals. The crystalline properties of the pulverized crystals of amobarbital were also studied. The degree of pulverization of amobarbital by recrystallization from glycols and their derivatives decreased with increase in the number of carbon atoms in the hydrophobic chain of these solvents. Examination of pulverized amobarbital was carried out by IR, X-ray diffraction, and DSC-TG, and two kinds of polymorphs were detected.
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IKUKATSU SUZUKI
1980 Volume 28 Issue 3 Pages
973-975
Published: March 25, 1980
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A protein, P-MSY, with immuno-competence promoting activity as well as antitumor activity has been isolated from bovine parotid glands. To help identify and characterize this protein, the amino-terminal and carboxylterminal amino acids were determined by Edman degradation and carboxypeptidase digestion. The amino-terminal was Ser-His- and the carboxyl-terminal was -Leu-His.
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MITSURU FURUKAWA, TADASHI OKAWARA, YOSHIHIDE NOGUCHI, MASUMI NISHIKAWA ...
1980 Volume 28 Issue 3 Pages
976-978
Published: March 25, 1980
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The dimers (2a-c) of active methylene compounds were readily synthesized by heating the corresponding α-sulfinyl compounds (1a-c) in carbon tetrachloride or tetrahydrofuran in 14-90% yields.
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EMAKO SUZUKI, MINORU IIYOSHI, MASASHI OKADA
1980 Volume 28 Issue 3 Pages
979-983
Published: March 25, 1980
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Nuclear magnetic resonance spectral data for a series of N-alkyl-N-(hydroxy- and oxoalkyl) nitrosamines are presented. The (Z)- and (E)-conformers of these N-nitrosamines were separated by high-pressure liquid chromatography and thin-layer chromatography.
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HIROKI TAKAHATA, HIDEO OKAJIMA, MASANORI NAGATA, TAKAO YAMAZAKI
1980 Volume 28 Issue 3 Pages
984-988
Published: March 25, 1980
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Reductive condensation of the amine (5) with the acid (2), followed by reduction of the carbonyl group and pyridine ring gave the cis-seco-8, 10-diazasteroid (12). Reductive cyclization of 12 with lithium aluminum hydride afforded two configurational isomers (14a, b) of 8, 10-diaza-estran. The stereochemistry of both isomers is discussed.
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SANGWON KIM, KEISHIRO NAGAO, ISOTAKA YOSHIMURA, YUTAKA OZAKI
1980 Volume 28 Issue 3 Pages
989-992
Published: March 25, 1980
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cis- and trans-2, 3-Epoxycycloheptanols were prepared stereospecifically from cyclohept-2-en-1-ol (1). Oxidation of 1 with tert-butyl hydroperoxide in the presence of a molybdenum catalyst gave the cis isomer (2) in high yield. The trans isomer (3) was obtained via the bromohydrin (4). The structure of 4 is discussed.
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SUSUMU ISHIMITSU, SADAKI FUJIMOTO, AKIRA OHARA
1980 Volume 28 Issue 3 Pages
992-994
Published: March 25, 1980
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A sensitive high-performance liquid chromatographic technique for the quantitative analysis of the isomers of hydroxyphenylalanine has been developed. The chromatographic conditions were as follows : stainless steel column (2.1×500 mm) packed with Hitachi #3011-C resin ; mobile phase, a mixture of equal volumes of 0.025 M sodium acetate and 0.05 M acetic acid ; flow rate, 0.8 ml/min ; temperature, 45° ; detection, fluorimetric detector. This procedure was found to be suitable for the analysis of 3, 4-dihydroxyphenylalanine, p-tyrosine, m-tyrosine, o-tyrosine, and phenylalanine.
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EIICHI KIMURA, TAKASHI YATSUNAMI
1980 Volume 28 Issue 3 Pages
994-997
Published: March 25, 1980
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Some cyclic derivatives of spermine and spermidine, 1, 5, 8, 12-tetraazacyclohexadecane 7, 1, 5, 9, 13-tetraazacycloheptadecane 9, and 1, 5, 9-triazacyclotridecane 11 were synthesized as part of our studies on the functions of natural polyamines and the effects of structural modification of the biological activities.
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MASATAKE NIWA, MASANOBU IGUCHI, SHOSUKE YAMAMURA
1980 Volume 28 Issue 3 Pages
997-999
Published: March 25, 1980
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Germacrene-D, which has sexual attractant properties similar to those of periplanone-B, has been isolated in an optically impure state from many plants, i.e., (-) and (+)-germacrene-D co-occur in different ratios in various plants. (-)-Germacrene-D isolated from Solidago altissima L. in this work was determined to have an optical purity of 18.0%. In addition, the optical rotation of optically pure germacrene-D was estimated to be 305°.
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