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Volume 27, Issue 1
Displaying 1-45 of 45 articles from this issue
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NORIO SUZUKI, YOSHIAKI TANAKA, RENZO DOHMORI1979 Volume 27 Issue 1 Pages 1-11
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of substituted thiazolo [4, 5-g]-, [5, 4-g]-, [4, 5-h]-and [5, 4-h] quinoline carboxylic acids has been prepared by the following two methods with the aim of providing new antimicrobial drugs. One of the synthetic methods has been carried out through successive steps of condensation of aminobenzothiazole with diethyl ethoxymethylenemalonate, Gould-Jacobs reaction, N-alkylation and hydrolysis. The other is thiazole ring cyclization of ortho-aminated mercaptoquinoline. These compounds prepared in this work were evaluated for antimicrobial activities in vitro. 9-Chloro-8-ethyl-5, 8-dihydro-5-oxothiazolo-[4, 5-g] quinoline-6-carboxylic acid (28b) showed the highest activity.View full abstractDownload PDF (1090K) -
YASUJI TAKASHIMA, TOSHIAKI NAKAJIMA, MITSUNORI WASHITAKE, TOSHIO ANMO, ...1979 Volume 27 Issue 1 Pages 12-22
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to study the decomposition of retionic acid in aqueous solution without surface-active agent, retinoic acid was dissolved in aqueous ethanolic solutions which contained various amount of water, and its thermal decomposition and photodecomposition was investigated. (1) In pyrolysis, retinoic acid was more stable than retinol or retinal. When water content was increased, the stability of retionic acid did not change as that of retinol and retinal. In photolysis, retinoic acid was decomposed rapidly, and its stability was not largely affected by N2 gas exchange and increasing water content. (2) Two decomposition products were recongnized, as the common decomposition products of retionic acid in pyrolysis and photolysis. The one seemed to be decarboxylated retinoic acid and the other seemed to be formed by the addition of a decomposition product to retinoic acid. In photolysis, additionally three other substances were recognized, the one was ethyl retionate and the two other substances seemed to be isomers of retinoic acid. (3) In photolysis, all-trans-retinoic acid was isomerized into 13-cis-and 9, 13-di-cis-isomers, but isomerization did not occur in pyrolysis.View full abstractDownload PDF (1140K) -
YUTAKA HIGASHI, SACHIKO UEI, NOBORU YATA, AKIRA KAMADA1979 Volume 27 Issue 1 Pages 23-30
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of salicylate on the distribution of five sulfonamides to red blood cells in rat were studied in vitro and in vivo. The distribution of sulfonamides to red blood cells in whole blood in vitro increased with an increase in their concentration in blood. But, in cell suspension without plasma, the distribution of the drugs to red blood cells was not influenced by their concentration. The distribution of sulfonamides except for sulfanilamide to red blood cells was enhanced by the addition of salicylate in whole blood. But, in cell suspension, the effect of salicylate was not observed. Addition of rat plasma to the cell suspension reduced the distribution of sulfonamides to red blood cells. It was considered that the unbound fraction of sulfonamides was responsible for their distribution to red blood cells. Thus, it may be concluded that salicylate inhibits the binding of sulfonamides to plasma protein, resulting in an increase in their unbound fraction and an enhancement of the distribution of sulfonamides to red blood cells.View full abstractDownload PDF (760K) -
HITOSHI SEKIKAWA, TSUTOMU NAGANUMA, JUNEI FUJIWARA, MASAHIRO NAKANO, T ...1979 Volume 27 Issue 1 Pages 31-37
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCoprecipitates were prepared in various ratio of tolbutamide-polyvinylpyrrolidone (PVP). The X-ray diffraction spectra indicated that tolbutamide in the coprecipitate did not exhibit its crystalline property. Comparative studies were made on the in vitro dissolution and the in vivo absorption of tolbutamide from the coprecipitate and the drug alone. The dissolution rate of tolbutamide was markedly increased in the tolbutamide-PVP coprecipitates in the pharmacopeial disintegration media at pH 1.2 and 7.5. In vivo absorption study of each preparation was carried out by determining the plasma level of tolbutamide following the oral administration to rabbits. Bioavailability of tolbutamide was improved in the coprecipitate 1.37 time as much as tolbutamide alone. It was shown that the drug was rapidly and completely absorbed following the oral administration of the coprecipitate. Quantitative analysis of PVP in the solution was also studied by the determination of the fluorescence of the complex of PVP and 8-anilino-1-naphthalenesulfonic acid sodium salt.View full abstractDownload PDF (789K) -
NAOYUKI KOIZUMI, YOSHINORI FUJIMOTO, TORU TAKESHITA, NOBUO IKEKAWA1979 Volume 27 Issue 1 Pages 38-42
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS^<13>C-NMR spectra of epimeric pairs of 24-hydroxy-, 24, 25-dihydroxy-, 1, 24-dihydroxy-, 24-methyl-and 24-ethyl-cholesterols were measured and the signals of all carbons assigned. Most of the side chain carbons in the C-24 epimeric mixtures showed split signals and characteristic differences between 24R and 24S isomers were recognized for the C-20 and C-24 signals, these resonances in the 24R compounds being always at slightly higher field than in the 24S isomers.View full abstractDownload PDF (539K) -
KAZUO YAMASAKI, KIMIKO FUJITA1979 Volume 27 Issue 1 Pages 43-47
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA 13C-nuclear magnetic resonance procedure is described for the rapid qualitative and quantitative analysis of ephedra alkaloids (I and II). This technique has been applied to the analysis of basic fractions from various ephedrae herba, giving results comparable to those obtained by gas-liquid chromatography technique, but with many advantages.View full abstractDownload PDF (527K) -
KOUKI KITAGAWA, KAZUKO UJITA, YOSHIAKI KISO, TADASHI AKITA, YOSHIHIRO ...1979 Volume 27 Issue 1 Pages 48-57
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive heptapeptide amides related to the C-terminal portion of tachykinins and two heptapeptide amides related to the C-terminal portion of bombesin-like peptides were synthesized and the smooth muscle contractile activity of these peptides was compared with that of the C-terminal heptapeptide of substance P by taking synthetic substance P as a standard.View full abstractDownload PDF (1193K) -
TOSHIHARU HOSONO, SEISHI TSUCHIYA, HIDEO MATSUMARU1979 Volume 27 Issue 1 Pages 58-64
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of d6-benzene on the nuclear magnetic resonance (NMR) spectra of N-vinyl-2-pyrrolidone (VP) was investigated. It was found that the orientation of amide group in VP to benzene was different from that in dimethylformamide (DMF) or methylpyrrolidone (MP) owing to repulsion of π-electron between vinyl group in VP and benzene ring. Subsequently the complex formation between DMF, MP, or VP and aromatic ring in ajmaline was also confirmed, in which the individual amide group in DMF, MP, or VP was oriented against aromatic ring in ajmaline as well as against benzene. In addition, it was recognized that polyvinylpyrrolidone (PVP) formed the complex with benzene in a slightly different orientation from that of VP with benzene because of the steric hindrance of PVP. It became apparent, however, that the resulting orientation was similar to that between VP and benzene when the chain length of PVP was relatively shorter. With increasing molecular weight of PVP, pyrrolidone ring would be considered to tend to lie at a certain angle to the plane of the benzene ring. Moreover, the complex formation of DMF, MP, or VP with ajmaline was regarded to be weaker than that with benzene from the association constant (Kn). Consequently, on the basis of the Kn value of PVP with benzene, the possibility of interaction between PVP and ajmaline was discussed.View full abstractDownload PDF (759K) -
KIYOSHI NARA, KOUICHI YOSHIOKA, MAKOTO KIDA1979 Volume 27 Issue 1 Pages 65-75
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSome N-alkyl derivatives of sorbistin A1 (P-2563 P) (1) and butirosin A (10) were prepared by reductive alkylation with aldehyde and NaBH4 or NaBH3CN. Among them, 4'-N-propylsorbistin A1 (8b) showed antimicrobial activity against gram-positive bacteria comparable to sorbistin A1 (1) and showed broader spectrum of activity against gramnegative bacteria including some of the sorbistin A1-resistant strains (K. pneumoniae, Ps. aeruginosa) than sorbistin A1 (1). 2'-N-Propylbutirosin A (14c) showed antimicrobial activity similar to butirosin A (10) and showed weak antimicrobial activity against some of butirosin A-resistant bacteria including E. coli JR 66/W 677 which is reported to produce 3'-phosphotransferase II. It was shown that 2'-N-propylbutirosin A (14c) was hardly phosphorylated under the condition where butirosin A (10) was almost completely phosphorylated with the purified E. coli JR 66/W 677 3'-phosphotransferase II.View full abstractDownload PDF (1162K) -
KANETO UEKAMA, FUMITOSHI HIRAYAMA, KANAKO ESAKI, MICHIKO INOUE1979 Volume 27 Issue 1 Pages 76-79
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTypical Bs type phase solubility diagrams were obtained for α-and β-cyclodextrins (α-CyD and β-CyD) with methyl cinnamate, ethyl cinnamate, and cinnamaldehyde in water at 25°. Solid complexes for α-and β-CyDs with three guest molecules were obtained and their molar ratios were found to be 2 : 1 (α-CyD/guest molecule) and 1 : 1 (β-CyD/guest molecule), respectively. In sharp contrast, apparent stability constant (Kc') and dissolution rate (kc') of α-CyD complexes were larger than those of β-CyD complexes. The thermal gravimetric analysis thermogram showed that the volatility of the guest molecule was lowered by the formation of CyD inclusion complex.View full abstractDownload PDF (500K) -
KEN IKEDA, YUKIHISA KURONO, YOSHIRO OZEKI, TOSHIHISA YOTSUYANAGI1979 Volume 27 Issue 1 Pages 80-87
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inhibition of esterase activity of human serum albumin (HSA) by the presence of several drugs (IN) was kinetically studied assuming a scheme of competitive binding to HSA between substrate, p-nitrophenyl acetate (NPA), and IN. The IN included N-arylanthranilic acids, coumarin derivatives and prostaglandins. The conditions of excessive concentrations of HSA and IN compared with NPA were employed to avoid complexities due to multiple active sites of HSA. For the solubilization of IN some organic solvents were added and the effects of the solvents on the reaction parameters of NPA with HSA were investigated. The dissociation constants of IN-HSA complexes were determined from the double reciprocal plots based on the scheme. The bulkiness of the substituents on phenyl groups of N-arylanthranilic acids enhanced the inhibition. Warfarin did not inhibit the reaction at all. Prostaglandins showed rather little inhibitions. From the comparisons of the dissociation constants obtained from this kinetic method with the literature binding constants from the conventional static methods, it was suggested that the esterase active site differed from the conventional binding sites on HSA.View full abstractDownload PDF (804K) -
SHOJI YAHARA, KIYOKO KAJI, OSAMU TANAKA1979 Volume 27 Issue 1 Pages 88-92
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew saponins, named ginsenosides-Rh1 (11) and -M7cd (17) were isolated from roots and flower-buds of Ginseng, repectively. Structures of 11 and 17 were established as 6-O-β-D-glucopyranoside of 20 (S) -protopanaxatriol and 20-O-β-D-glucopyranoside of dammar-25-ene-3β, 6α, 12β, 20 (S), 24ξ-pentaol, respectively by means of carbon-13 nuclear magnetic resonance spectroscopy as well as their preparations from the known saponins. Further isolation and identification of the following dammarane-type saponins from the aerial parts of Ginseng were also reported : ginsenosides-Rb1 (1), -Rb2 (2), -Rc (4) from the leaves ; 1, 2, 4, and ginsenoside-F3 (15) from the flower-buds, and 2, 4, ginsenosides-Rd (5), -Re (6), and -Rg1 (8) from the fruits. As shown in Table II, isolation of these biologically active saponins in relatively high yields indicated the significance of the aerial parts of Ginseng as the good medicinal sources.View full abstractDownload PDF (677K) -
YOSHIHARU MACHIDA, HIROSHI MASUDA, NORIMASA FUJIYAMA, SUSUMU ITO, MASA ...1979 Volume 27 Issue 1 Pages 93-100
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new topical disk-like dosage form for carcinoma colli was prepared by direct compression of the mixture of bleomycin hydrochloride (BLM) and combination of hydroxypropyl cellulose (HPC) and other water soluble polymer. After in vitro examinations regarding the water adsorption, the release and dissolution of drug and other properties, the preparations were examined clinically by applying to the voluntary patients. A combination of HPC and Carbopol 934 (CP) seemed preferable as the vehicles, and the amount of BLM released from the preparation increased remarkably with an increase in concentration of HPC. In contrast, the water absorbing property increased with an increase of CP. The preparation containing 30 mg of BLM, for which the preparative formula was designed according to the in vitro experiment, was administered to the voluntary patients of carcinoma colli of stage O to Ib. The preparation taken out of patient indicated the continuous release of BLM for longer than 24 hr. In the three of nine patients, any cancerous focus was not found after the local therapy using 90 to 195 mg of BLM in total, and remnant foci found in the other six patients were very few. Moreover, the normal mucosa was not affected by BLM, contrary to the case of usual suppositories reported. The higher per cent of cure might be expected if the therapy could be continued for the longer period.View full abstractDownload PDF (1136K) -
MISAO NAKANO, KAZUYO FUJII, SHIGERU GOTO1979 Volume 27 Issue 1 Pages 101-108
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was found by in vitro equilibrium dialysis method that there is a small difference in the binding percentage of three diuretics, hydrochlorothiazide, furosemide, and ethacrynic acid, to bovine serum albumin and that to human serum albumin (between two animal species). The binding of three diuretics to human serum was examined in healthy adults and in patients with renal failure. In the healthy adults, binding of three diuretics was dependent on the degree of dilution of human serum. The same type of binding percentage curves was obtained when crystalline human serum albumin and healthy adult serum were diluted with M/15 phosphate buffer. This fact may suggest the possibility that the albumin level in human serum was closely related to the diuretics binding process. In the renal failure, the binding of hydrochlorothiazide and furosemide was correlated with the albumin concentration in human serum. However, the renal failure had reduced the binding of ethacrynic acid due to decreased serum binding capacity. Calculation of binding percentages would be required to assess the clinical importance of decreased binding of diuretics to serum of patients with renal failure.View full abstractDownload PDF (842K) -
MICHIYA KIMURA, TOSHIKI MUTO1979 Volume 27 Issue 1 Pages 109-112
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA model reaction was investigated for the biological oxyfunctionalization of steroid. The benzene solution of cholesteryl acetate (I), tert-butyl hydroperoxide, and tris (acetylacetonato) iron (III) in a molar ratio of 1.2 : 9.2 : 0.13 was refluxed under argon atmosphere and time-course of the reaction was followed for 24 hours. The products identified were 3β-acetoxycholest-5-en-7-one (II), 3β-acetoxycholest-5-en-7-ols (III ; trace), 3β-acetoxy-5, 6-epoxycholestanes (IV), and the alkyl peroxides (Va, Vb, and Vc). These peroxides showed maximum concentration in the early period of the reaction and most of the substrate (I) was consumed by this time. The structures of Va and Vb were elucidated to be 3β-acetoxycholest-5-ene-7α-tert-butylperoxide and its 7β-epimer, respectively. The product Vc was assumed to be 3β-acetoxycholest-6-ene-5ξ-tert-butylperoxide. The ketone (II) was a major product when the peroxides (Va and Vb) came into contact with the oxidation system mentioned above ; the yields from Va and Vb were 56 and 94%, respectively. Thus it was concluded that the major final product (II) may be formed through the intermediary peroxides (V) in the titled reaction.View full abstractDownload PDF (624K) -
MAMORU SUGIURA, MASAO ISHIKAWA, MASANORI SASAKI, SHOJI AWAZU1979 Volume 27 Issue 1 Pages 113-118
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhysicochemical properties of the purified leucine amino peptidase from Aspergillus japonica were studied. The molecular weight of this enzyme was estimated to be approx. 31100 by sedimentation equilibrium, and the sedimentation coefficient (S20, W) was determined to be 3.12 S. The extinction coefficient at 278.5 nm, E1%1cm was 7.72 and the isoelectric point was at around pH 8.0 by gel electrofocusing. The helical content was calculated to be 1.7% from the Moffit-Yang plots. The amino acid analyses indicated that the enzyme was composed of 289 amino acid residues and contained one cystine. The amino-terminal amino acid was lysine, and the partial specific volume calculated from amino acid composition was 0.726.View full abstractDownload PDF (673K) -
MAKOTO SATO, MASAYUKI KITAGAWA, FUMIHIKO UCHIMARU, KATSUJIRO UENO, HIR ...1979 Volume 27 Issue 1 Pages 119-128
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to search for new psychotropic agents, several conformationally restricted analogs (see Chart 1D) of haloperidol or benperidol were synthesized. cis-and trans-1-[2- (2-Phenylcyclopropyl) ethyl] piperidine derivatives (Xa, Xb, and XXIV) were prepared in several steps from the corresponding cis-and trans-1-phenyl-1-butene derivatives (III and XX). The effect of the compounds on spontaneous motor activity in mice was determined. trans-Isomer (Xb), which was the most active compound, was about 11 times more active than cis-isomer (XXIV). But the activity of Xb was about one-fifth as potent as benperidol. Structure-activity relationships of these compounds are discussed.View full abstractDownload PDF (1034K) -
JUICHIRO SHIBASAKI, RYOJI KONISHI, TADASHI KITASAKI, TAMOTSU KOIZUMI1979 Volume 27 Issue 1 Pages 129-138
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe relationship between time course of blood level of acetaminophen (NAPA) and time-analgesic effect course was examined in mice after intravenous and subcutaneous administration of NAPA in doses of 149, 200, 268, and 360 mg/kg. The results obtained were as follows. (1) When the effect and the corresponding blood level obtained from time course studies of 4 kinds of doses were examined together, their relationship seemed to be rather poor. Namely, like blood level due to different doses produces no like effect. (2) When only the data after the peak effect were examined for each dose, respectively, higher relationship was found both in intravenous and subcutaneous studies. It was also found that with increasing of doses, the rate at which effect decreased from the peak became faster and higher blood level came to be necessary for obtaining a certain level of effect. (3) comparing the time course data at the same doses, the effects after subcutaneous administration were always lower than those after intravenous administration even when NAPA blood level after subcutaneous administration were higher, suggesting that effect of NAPA might not depend on NAPA level in the blood or in the site of action at the time when effect was measured but rather on the peak NAPA level there and the elapse of time. (4) In conclusion, the relationship observed under a variety of doses and administration routes of NAPA is so complicated that even the possibility that analgesic effect elicited by this drug may be inherently beyond the limits of kinetic explanation cannot be ruled out.View full abstractDownload PDF (1000K) -
SADAO BABA, TOMOKO BABA, TAKAO IWANAGA1979 Volume 27 Issue 1 Pages 139-143
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA study has been made of the effect of acetohexamide [N-(p-acetylphenylsulfonyl)-N'-cyclohexylurea] in blood plasma on the creatinine assay procedure based on the Jaffe reaction. An analytical method has been proposed in order to determine the drug in plasma and to clarify the causative relationship between plasma acetohexamide and creatinine values. The method involves the formation of 2, 4-dinitrophenyl (DNP) derivative of the liberated cyclohexylamine from the drug on hydrolysis and its determination by high-pressure liquid chromatography with an ultraviolet detection. It was found that false positive errors in creatinine assay values due to an oral dose of 500 mg of the drug ranged from about 40 to 100 percent in the given subjects with diabetes. The change with time in the concentration of plasma glucose was also described.View full abstractDownload PDF (532K) -
ISAMU MURAKOSHI, KAZUO TORIIZUKA, JOJU HAGINIWA, SHIGERU OHMIYA, HIROT ...1979 Volume 27 Issue 1 Pages 144-146
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new glucosidic lupin-alkaloid, (-)-(trans-4'-β-D-glucopyranosyloxycinnamoyl)-lupinine (5), was newly isolated from the fresh seedings of Lupinus luteus. Its structure has been confirmed by direct comparison with a synthetic material. The concentration of 5 in the immature and mature seeds of L. luteus was negligibly low, but its concentration increased rapidly during the first 3-10 day's growth of seedlings and became a minor component again in the later stages of the plant's growth.View full abstractDownload PDF (519K) -
Thin-Layer Chromatographic Determination of Panaxadiol and Panaxatriol by Ultraviolet DerivatizationYUHICHIRO SARUWATARI, HIROMICHI BESSO, KIYOSHI FUTAMURA, TOHRU FUWA, O ...1979 Volume 27 Issue 1 Pages 147-151
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPanaxadiol (I) and panaxatriol (II) yielded on hydrolysis of ginseng saponins with 5% H2SO4/H2O-EtOH (3 : 1) quantitatively reacted with a hundred fold excess of β-naphthoyl chloride in pyridine at room temperature, respectively. Completely stable derivatives, which were obtained as β-naphthoates, were analyzed by a thin-layer chromatography-dual chromatoscanner. This procedure was applied to the evaluation of the commercial ginseng.View full abstractDownload PDF (539K) -
TETSUJI KAMETANI, MASAYOSHI TSUBUKI, HIDEO NEMOTO, KEIICHIRO FUKUMOTO1979 Volume 27 Issue 1 Pages 152-157
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 2, 3, 4, 9, 10-Hexahydro-6-methoxy-1, 1, 4-trimethylbenz [f] azulene (15) was synthesized by a rearrangement of 2, 3, 3a, 4, 5, 9b-hexahydro-9b-(1-hydroxyethyl)-8-methoxy-3, 3-dimethyl-1H-benz [e] indene (14), which was in turn obtained from a thermolysis of the olefinic benzocyclobutene (11) followed by treatment with methyllithium. The hexahydrobenzazulene (15) was converted into 7-formylmethyl-1, 2, 3, 3a, 4, 9, 10, 10a-octahydro-6-methoxy-1, 1, 4-trimethylbenz [f] azulene (1) through the compounds 16-21. The synthesis of 1, 2, 3, 4, 10, 11-hexahydro-7-methoxy-5H-dibenzo [a, d] cycloheptene (6) by a rearrangement of 1, 2, 3, 4, 4a, 9, 10, 10a-octahydro-4a-hydroxymethyl-6-methoxyphenanthrene (5) was also described.View full abstractDownload PDF (795K) -
NOBUKO SAKURAI, TAKAO INOUE, MASAHIRO NAGAI1979 Volume 27 Issue 1 Pages 158-165
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcetyl shengmanol xyloside (I) (monohydrate) isolated from the underground part of Cimicifuga japonica (Ranunculaceae) has mp 280-281°, [α] D-23.7°. The peracetate (II) of I afforded, on acid hydrolysis in aq. methanol, 25-O-methyl cimigenol (VI) along with cimigenol (IV) and isodahurinol (V). I yielded 25-O-methyl cimigenol xyloside (VI) and 25-O-acetyl cimigenol xyloside (VII) on a mild treatment with p-toluene sulfonic acid in methanol, while it afforded cimigol 3-xyloside (VIII) on alkali treatment. This transformation of I into VI, and its stereoisomer (VIII) at C-15 and -24 was rationalized in view of different modes of reaction to open the epoxide ring of I on the acidic and the alkaline conditions. Acetyl shengmanol xyloside (I) was degradated with periodate in a solution of cyclohexylamine to afford an aldehyde-carboxylic acid, methyl ester (XIII) of which has structure (XV). On enzymatic hydrolysis, I yielded its genuine aglycone acetyl shengmanol (XVI), [α] D-16.1°, as an amorphous powder. The sugar moiety of I was concluded to be attached to C-3 oxygen of the genin (XVI) as β-D-xylopyranose. On the basis of chemical and spectral data, the structure of acetyl shengmanol xyloside (I) was proposed to be 23R, 24S-3β, 15ξ-dihydroxy-23-acetoxy-24, 25-epoxy 9, 19-cyclolanostan-16-one-3β-D-xylopyranoside. This xyloside (I) is unstable even in the separation procedures from the plant materials, and seems to be a precursor of naturally occurring xylosides of cimigenol, cimigol and their derivatives in C. japonica.View full abstractDownload PDF (1063K) -
TARO OGISO, HIROYUKI MASUDA, MASAYA SEKO1979 Volume 27 Issue 1 Pages 166-175
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to gain insight into the mechanisms by which OK-432 (a lyophilized preparation of an attenuated strain of Streptococcus haemolyticus) treatment lyzed tumor cells, the in vivo effect of the agent on some enzymes, cellular components and surface properties of ascites hepatoma, AH 130 and AH 41 C cells, was studied in comparison with the effect of 5-fluorouracil (5FU) and cyclophosphamide (CP) on these parameters. Administration of OK-432 (0.5 mg/rat/day) to AH 130 cell-bearing rats for 4 days was found to enhance leakage of intracellular potassium and calcium, cause a decrease in hexokinase activity, cause a decrease in saturated fatty acids but a significant increase in cholesterol, unsaturated fatty acids of total phospholipids and 2, 4, 6-trinitrobenzenesulfonate binding to phosphatidylethanolamine as compared with the control cells. OK-432 administered for 2 days to AH 41 C cell-bearing rats also enhanced the leakage of the intracellular cations and the proportion of arachidonic acid in total phospholipids. On the other hand, significant alterations of these parameters in the cells were not demonstrated by 5FU and CP treatments. OK-432 treatment is considered to have an important influence on the lipid metabolism of the cells resulting in an increase in membrane fluidity which is related to leakage of essential components and hexokinase, consequently the leakage appears to inhibit the cell growth.View full abstractDownload PDF (1271K) -
SATOSHI OMURA, CHIAKI KITAO, HIDETAKA HAMADA, HARUO IKEDA1979 Volume 27 Issue 1 Pages 176-182
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFinal steps in the biosynthesis of spiramycin was studied by using cerulenin, a specific inhibitor of fatty acid and polyketide biosynthesis. The spiramycin-related compounds were tested for transformation with Streptomyces ambofaciens, a spiramycin producing strain, under the condition inhibiting the biosynthesis of aglycone by cerulenin. Forocidin I (4'-demycarosyl 9-deforosaminyl-spiramycin I) was converted into forocidin III (3-propionyl forocidin I), neospiramycin I (4'-demycarosyl spiramycin I), neospiramycin III (3-propionyl neospiramycin I), and spiramycin III (3-propionyl spiramycin I). Neospiramycin I was also converted to neospiramycin III and spiramycin III. Spiramycin I was rapidly transformed into spiramycin III, while neospiramycin III was not converted to any other compounds. These results suggested that the binding of forosamine to aglycone precedes the mycaroside formation, and that the acylation of aglycone at C-3 occurs in the final step of spiramycin biosynthesis.View full abstractDownload PDF (717K) -
AKIRA MATSUDA, YUJI NOMOTO, TOHRU UEDA1979 Volume 27 Issue 1 Pages 183-192
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA facile displacement of a methylsulfonyl group in adenosines with cyanide ion is described. Treatment of protected 8-methylsulfonyladenosines with sodium cyanide in dimethylformamide gave the 8-cyanoadenosines. The conversion of the cyano group to the methyl imidate, methoxycarbonyl, carbamoyl, and carboxylic acid, respectively, was achieved. Similar reaction was carried out with 2-methylsulfonyladenosines to give the 2-cyanoadenosines and their derivatives. The nuclear magnetic resonance (NMR) and circular dichroism (CD) spectra of these 2-and 8-substituted adenosines are given. The 8-substituted adenosines possess syn-conformations while the 2-substituted derivatives prefer to possess anti-conformations, as confirmed by the CD and NMR spectra.View full abstractDownload PDF (1167K) -
KIYOTO EDO, TAKAO SAKAMOTO, HIROSHI YAMANAKA1979 Volume 27 Issue 1 Pages 193-197
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthyl 5-pyrimidineacrylates, 5-pyrimidineacrylonitriles, and 5-styrylpyrimidines with alkyl groups at the 2-and 4-positions were synthesized by means of the coupling reaction of 5-halopyrimidines with olefines in the presence of palladium phosphine complex. According to a similar manner, pyridines, quinolines, and isoquinolines with the same substituents at the β-positions were obtained in good yield.View full abstractDownload PDF (618K) -
KATSUMI NANJO, MINORU SEKIYA1979 Volume 27 Issue 1 Pages 198-203
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSelective reduction of carbon-carbon double bond conjugated with nitro group has been demonstrated with a number of examples by the use of the TEAF reagent (triethylamine-formic acid azeotrope) in N, N-dimethylformamide. In addition, formic acid reduction of carbon-carbon double bond conjugated with both sulfonyl and other electron-withdrawing groups has been exemplified by the same manner.View full abstractDownload PDF (641K) -
KENJI SUGIBAYASHI, YASUNORI MORIMOTO, TANEKAZU NADAI, YOSHIO KATO, AKI ...1979 Volume 27 Issue 1 Pages 204-209
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBovine serum albumin microspheres contatining 5-fluorouracil-6-3H were prepared by heating at 180° (or 150°, 100°) of 25% albumin solution in cottonseed oil emulsion. The shape of this microsphere was invariably spherical, and the average diameter was 0.66μ. After intravenous injection in mice, 5-fluorouracil-6-3H entrapped in albumin microspheres localized mainly in the liver, and the disappearance rate of radioactivity in microspheres from the tissue was very slow in comparison with that of free drugs. The microsphere might be delivered into reticuloendothelial system in the liver because ofits phagocytic activity, as well as the distribution following injection of albumin macroaggregates. Such preferential localization and sustained release of entrapped drugs suggested that albumin microspheres are useful as drug-carrier in chemotherapy.View full abstractDownload PDF (854K) -
KAZUO ITO, JENGSHIOW LAI1979 Volume 27 Issue 1 Pages 210-214
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMarsformoxide A (IX) is a triterpene substance possessing an epoxide ring in the molecule, which was previously isolated by us from Marsdenia formosana MASAMUNE (Asclepiadaceae). Irradiation of marsformoxide A with a high pressure mercury lamp in acidic medium furnished D-friedours-11, 14-dien-3β-yl acetate (XI), and urs-9 (11), 12-dien-3β-yl acetate (XII), together with recovery of the starting material IX.View full abstractDownload PDF (604K) -
TAKEFUMI MOMOSE, SHUJI UCHIDA, TAKESHI IMANISHI1979 Volume 27 Issue 1 Pages 215-221
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe conversion of 1-(3-chloropropyl)-cis-decahydroquinoline-2, 7-dione (3) into decahydro-3H, 8H-benzo [i, j] quinolizine-3, 8-diones (12a and 12b) was accomplished with retention of the parent stereochemistry. The stereochemistry of the tricyclic system was assigned from chemical and physical evidences. It was postulated that this successful ring closure in the cis ring system resulted from easy fulfilment of the stereoelectronic requirement, for intramolecular alkylation in 3, much reduced as compared to that for N-acrylyl-cis-octahydro-7 (1H)-quinolone (1b).View full abstractDownload PDF (861K) -
TAKEFUMI MOMOSE, OSAMU MURAOKA, SHOHGO ATARASHI, TAMIKO HORITA1979 Volume 27 Issue 1 Pages 222-229
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Baeyer-Villiger oxidation of bicyclo [3. n. 1] alkan-3-ones and related systems is described. Bicyclo [3. 3. 1] nonan-2-one (8) was oxidized into the corresponding lactone, which was found to be converted into the cis-1, 3-disubstituted cyclohexane system by the subsequent methanolysis. Meanwhile, the 3-oxo system (2) manifested an anomalous inactivity against the oxidation. The"backside steric hindrance"caused by the axial (endo) proton at C-7 was postulated as the origin of the inactivity. The differential reactivity of the ketones in the Baeyer-Villiger reaction of the bicyclic systems (2, 3, 4) enabled the regiospecific lactonization of the bicyclic diketones (17, 18, 19) into the lactones (37, 38, 39), which would be important precursors for specifically substituted medium-sized lactones, to be achieved.View full abstractDownload PDF (886K) -
YOSHIHIKO INAMORI, KAZUHIRO MORIMOTO, KATSUAKI MORISAKA, GEN-ICHI SAIT ...1979 Volume 27 Issue 1 Pages 230-234
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the mode of the delayed toxicity of streptothricin antibiotics, 14C-glycyl-racemomycin-A and racemomycin-D were each administered intravenously to mice and rats in a seuviving dose. As to the distribution of 14C-glycyl-racemomycin-A in the organs of mice, studies confirmed us that it was distributed in kidney in a high concentration in comparison with the distribution in the other organs. Therefore, pathohistological reviews were carried out on the kidney which was whitened macroscopically. As a result, severe toxicity wide-spread in the cortex renis was observed in the kidney. From these results, it was recogenized that streptothricin antibiotics produce nephrotoxicity. As to the developmental mechanism of the delayed toxicity, the authors presented the assumption that after the administered antibiotic us, in vivo, transformed into acid, lactam ring of which is broken from examination of radiochromatogram of metabolite in urine, and that the acute toxicity of that acid is responsible for the delayed toxicity.View full abstractDownload PDF (892K) -
YUKIO MORI, TOSHIRO HORI, KAZUMI TOYOSHI1979 Volume 27 Issue 1 Pages 235-237
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMetabolism of 3'-methyl-4-(dimethylamino) azobenzene (3'-Me-DAB) and 3'-methyl-4-(methylamino) azobenzene (3'-Me-MAB) by the rat liver was investigated by the use of a tracer technique. 3'-Me-DAB [5'-3H] or 3'-Me-MAB [5'-3H] was incubated with a 9000 g supernatant fraction at 37°in an aerobic condition for 30 min. The metabolites were extracted with benzene-acetone. The residual aqueous solution was applied to an Amberlite XAD-2 column and the metabolites were eluted with methanol. The metabolites in the extract or eluate were determined by the reverse isotope dilution analysis after separation by thin-layer chromatography. The recovery of radioactivity in benzene-acetone extract after incubation of 3'-Me-DAB [5'-3H] was 70.8±7.5%. About 99.5% of the radioactivity extracted was identified with the N-demethylated, oxidized at 4' position and ring methyl group, and azo-reduced metabolites and the substrate. On the other hand, 79.4% or 83.8% of radioactivity recovered in each eluate was identified with 3-aminobenzoic acid and 3-acetaminobenzoic acid. Accordingly, it was proved that the metabolites oxidized at the ring methyl group was also detected in the in vitro metabolism of 3'-Me-DAB or 3'-Me-MAB.View full abstractDownload PDF (484K) -
KUNIO TAKAHASHI, TADAHIRO TAKEDA, SHOJI SHIBATA1979 Volume 27 Issue 1 Pages 238-241
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe water-soluble polysaccharides isolated from the laboratory cultures of lichen mycobionts and phycobionts were studied comparatively. The polysaccharides of mycobionts so far tested showed close similarities with those of parent lichens, whereas the polysaccharides of phycobionts gave different features. Therefore, it is highly probable that the water-soluble polysaccharides of lichens are mostly produced by their mycobionts as like as the lichen metabolites of smaller molecular size.View full abstractDownload PDF (515K) -
KATSUHIDE MATOBA, AKIKO FUKUSHIMA, HIROSHI ARAI, TAKAO YAMAZAKI1979 Volume 27 Issue 1 Pages 242-246
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe syntheses of 5-hydroxyl-4'-methoxy-7-methyl-6-azaflavanone (Ia) and 5-hydroxy-4'-methoxy-7-methyl-6-azaflavone (IIa) from 4-hydroxy-6-methyl-2 (1H)-pyridone (IVa), and the syntheses of Ib and IIb, N-methyl analogues of Ia and IIa respectively, and of IIc, N-methyl-4'-demethoxy analogue of IIa, starting with N-methyl analogue (IVb) of IVa, were described.View full abstractDownload PDF (680K) -
TADASHI ISHIMITSU, SHINGO HIROSE, HIROMU SAKURAI1979 Volume 27 Issue 1 Pages 247-251
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe two phenol ionizations of 3, 4-dihydroxyphenylbutyric acid and 3, 4-dihydroxybenzoic acid were studied by detailed potentiometric titration and complementary tristimulus colorimetric method (CTS method). The thermodynamic parameters were calculated from the dissociation constants. From a comparison of the related compounds of 3, 4-dihydroxyphenylbutyric acid, it was indicated that the effect of carboxylate group on the dissociations of two phenol groups was not present when more than two methylene groups were introduced between benzene ring and carboxylate group. The microscopic acid dissociation constants of 3, 4-dihydroxyphenylbutyric acid and 3, 4-dihydroxybenzoic acid were calculated by two different methods. In Method A, the dissociation constants of 3-methoxy-4-hydroxyphenyl derivatives were used as substituted values. Method B is a modification of Edsall method. There were no effect of carboxylate group on the tautomeric constants when more than one methylene group are introduced between benzene ring and carboxylate group.View full abstractDownload PDF (531K) -
KIYOSHIGE OCHI, ISAO MATSUNAGA, MINORU SHINDO, CHIKARA KANEKO1979 Volume 27 Issue 1 Pages 252-254
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe convenient synthesis of 25-hydroxycholesterol (6) is described. 5β-Cholestan-3α, 25-diol (2) derived from lithocholic acid was converted to 6 via four steps : oxidationbromination, dehydrobromination, deconjugation, and reduction. The overall yield of 25-hydroxycholesterol (6) starting from 2 was ca. 50%.View full abstractDownload PDF (469K) -
KIYOKO TAKAMURA, MIZUHO SAKAMOTO1979 Volume 27 Issue 1 Pages 254-257
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe catalytic effects of several metal ions on the anodic oxidation of ascorbic acid (I) at a platinum electrode were studied by a linear sweep voltammetry in 1M perchloric acid. Contrary to the air-oxidation of I, Bi3+ and Pb2+ exhibit a marked effect whereas Cu2+ shows a minor one.View full abstractDownload PDF (543K) -
Y.A. AL-FARKH, F.H. AL-HAJJAR, F.S. AL-SHAMALI, H.S. HAMOUD1979 Volume 27 Issue 1 Pages 257-264
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 3-Diaryl-2-propen-1-one (I) reacted with aroyl-and acyl-hydrazines and ethyl hydrazinecarboxylate (II) in the presence of prperidine to give the corresponding α-[3-(1, 3-diaryl-propan-1-one)]-β-acyl or-aroyl-hydrazines and ethyl β-[3-(1, 3-diaryl-propan-1-one)]-hydrazine-carboxylate (IV), respectively. The structure and configuration of these compounds are based on chemical analysis and spectroscopic evidence.View full abstractDownload PDF (720K) -
YOSHITAKA NITTA, TACHIO AIMOTO, RYOHEI KIMURA, TOSHIRO MURATA, KEIJI I ...1979 Volume 27 Issue 1 Pages 264-267
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe blood and tissue levels of unchanged ethchlorvynol (EC) were determined after intraperitoneal administration of EC suspended in 5% polyethylene glycol 400 aqueous solution (5% PEG). Pre-oral administration of 5% PEG did not show any effect on the levels of EC in blood and tissues, compared with the pre-treatment of normal saline as a control. However, pre-administered corn oil as well as peanut oil and soybean oil decreased the brain levels of EC. In order to exclude the effect of the vegetable oils, the thoracic fistula rats were used in the studies. When EC was administered orally in corn oil to the fistula rats, the brain levels of EC were fairly improved, and were higher than in the intact rats. As little as 0.06 and 0.05% of total dose were recovered in the lymph as EC and EC-glucuronide (ECG), respectively after oral administration of EC in corn oil. While both EC and ECG were not detected in the lymph when EC was given in 5% PEG.View full abstractDownload PDF (497K) -
SEIGO FUKUSHIMA, KAZUKO NORO1979 Volume 27 Issue 1 Pages 267-269
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7-n-Alkylcarbamoyltheophyllines (V) were synthesized from theophylline and n-alkyl isocyanates.View full abstractDownload PDF (370K) -
HIROSHI YAMANAKA, MASAFUMI SHIRAIWA, KIYOTO EDO, TAKAO SAKAMOTO1979 Volume 27 Issue 1 Pages 270-273
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe quinoline, isoquinoline, and acridine derivatives containing an acetylenic side chain at the pyridine moiety were synthesized by means of coupling reaction of alkyl (or phenyl) acetylenes with the corresponding halogeno derivatives in the presence of a palladium triphenylphosphine complex.View full abstractDownload PDF (492K) -
CHUZO IWATA, MINORU YAMADA, YASUTAKA SHINOO1979 Volume 27 Issue 1 Pages 274-275
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Chamigrene has been synthesised via a new spiro-annelation reaction, copper (II) chloride catalysed decomposition of phenolic α-diazoketone (III).View full abstractDownload PDF (357K) -
JIRO ENDO, MOTOO NAGASAWA, HIDEJI ITOKAWA, YOICHI IITAKA1979 Volume 27 Issue 1 Pages 275-278
Published: January 25, 1979
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new sesquiterpenoids, caulolactone A (II) and caulolactone B (III) were isolated from A sarum caulescens. It was suggested that they were formed via the conformers I-A and I-B of germacrone-4, 5-epoxide (I) respectively. Moreover, two configurational isomers of germacrone-1, 10 ; 4, 5-diepoxides (IV and V) were derived from I also via I-A and I-B.View full abstractDownload PDF (408K)
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