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Volume 104, Issue 7
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YOSHIHIKO ITO, TAKEO SAEGUSA1984 Volume 104 Issue 7 Pages 701-712
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSyntheses of polycycles by means of organometallic compounds are described. (I) Indole synthesis from isonitriles : o-(α-Lithioalkyl) phenyl isocyanides, which are generated in situ at -78°C by treatment of o-alkylphenyl isocyanides with lithium diisopropylamide, are intramolecularly cyclized at room temperature to give indoles after aqueous workup. (II) New generation of o-quinodimethanes and their [4+2] cycloadditions : o-Quinodimethane intermediate, which is generated by CsF induced 1, 4-elimination of o-[(trimethylsilyl) methyl] benzyltrimethylammonium iodide is trapped inter- and intramolecularly with dienophiles to give Diels-Alder adducts. Polycycles including steroidal structure are synthesized on the basis of the new generation of o-quinodimethanes. (III) New generation of o-quinone methide imines and their [4+2] cycloadditions : o-Quinone methide imine intermediates generated in situ from o-[N-(trimethylsilyl)-N-alkylamino] benzyltrimethylammonium bromide and CsF are trapped inter- and intra-molecularly with dienophiles to afford nitrogen containing polycycles. A total synthesis of gephyrotoxin is approached by means of the intramolecular cycloaddition of o-quinone methide imine. (IV) Cyclizations of Pd (II) enolate intermediates : Intramolecular cyclizations of Pd (II) enolate intermediates which are formed by reaction of olefinic silyl enol ethers with Pd (II) salt provide a convenient synthesis of polycyclic ketones.View full abstractDownload PDF (773K) -
TSUTOMU KAMIYAMA, SABURO ENOMOTO, MASAMI INOUE1984 Volume 104 Issue 7 Pages 713-717
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe combination catalyst of palladium and chromium phosphate was found to have an excellent activity for the formation of cyclohexyl acetate from phenol and acetic acid under hydrogen pressure. By use of 1% palladium supported on acid clay and chromium phosphate (CrPO4·1.8H2O), the yield of cyclohexyl acetate was 53.8% at 180°C for 5 h. This catalyst system was applied to the hydro-esterification of dihydric phenols. The reaction path for this reaction is discussed.View full abstractDownload PDF (475K) -
MITSUTOMO TSUHAKO, CHIYOKO SUEYOSHI, HIROYUKI NARIAI, ITARU MOTOOKA1984 Volume 104 Issue 7 Pages 718-723
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEight articles (made by 6 makers) of poly-, meta-, and ultraphosphate, being available commercially as condensed phosphates for medicinal and food additives, were submitted to the following tests : determination of phosphorus, pH of 1% solution, solubility, hygroscopic test, hydrolysis, and determination of phosphates with various chain lengths in condensed phosphates by means of anion-exchange chromatography. 1) P2O5 contents of poly- and metaphosphate, though somewhat variations were detected one another according to their makers, lay in the range of 66-69%, while those of ultraphosphate in the range of 71-77%. 2) Even the same metaphosphate or ultraphosphate, their solubility largely differed one another according to their makers. In some cases, the same articles of the same maker largely differed in their solubility rates, from one lot to another. It was found that the solubilities of poly-, meta-, and ultraphosphate depend strongly on the content of long- chain polyphosphates in them. 3) In the hygroscopic test, poly- and metaphosphates absorbed moisture little. However, ultraphosphate showed a strong hygroscopic property. The higher the P2O5 content of the condensed phosphates, the stronger was the hygroscopic property. 4) It was found from the results of anion-exchange chromatography that commercially available poly-, meta-, and ultraphosphates were mixtures of phosphates with various chain lengths. It was also ascertained that poly- and metaphosphates containing larger amounts of long-chain phosphates above undecaphosphate (P11) were lower in their solubility rates as well as in their hydrolysis rates.View full abstractDownload PDF (698K) -
TSUNEMATSU TAKEMOTO, SHIGENOBU ARIHARA, KAZUKO YOSHIKAWA, TADASHI NAKA ...1984 Volume 104 Issue 7 Pages 724-730
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFive dammarane-oligoglycosides named gypenoside XXV (1), XXVI (2), XXXIV (3), XXXV (4) and XXIX (5) were isolated from the aerial parts of Gynostemma pentaphyllum MAKINO collected in Hyogo pref. On the basis of chemical and physicochemical evidence, they were characterized as follows : 1, 19-oxo-20 (S)-hydroxydammar-24-ene-3-O-β-glucopyranosyl (1→2)-α-L-arabinopyranoside-21-O-β-glucopyranoside : 2, 19-oxo-21-hydroxydamar-24-ene-3-O-β-glucopyranosyl (1→2)-α-L-arabinopyranoside-20 (S)-O-β-D-glucopyranoside : 3, 19-oxo-21-hydroxydammar-24-ene-3-O-β-sophoroside-20 (S)-O-β-sophoroside-20 (S)-O-β-rutinoside : 4, 19-oxo-21-hydroxydammar-24-ene-3-O-β-sophoroside-20 (S)-O-β-primeveroside : 5, 19-oxo-20 (S)-hydroxydammar-24-ene-3-O-β-glucopyranosyl (1→2)-α-L-arabinopyranoside.View full abstractDownload PDF (733K) -
SHINICHIRO SAKAI, HIROMITSU TAKAYAMA, KEIICHI YAMAGUCHI, NORIKO IDE, T ...1984 Volume 104 Issue 7 Pages 731-752
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFormal total syntheses of isodelphinine (3) and penduline (50) was achieved. Isodelphonine (19), an alkamine of 3, was synthesized by the following two routes from chasmanine (1), which had already been synthesized by Wiesner et al. Des-N-ethyl-diacetylchasmanine (8) was derived from 1 by the known method, and des-N-ethyl-N-formyl-14-acetyl-8, 15-epoxychasmanine (12) was synthesized via intermediates, des-N-ethyl-N-formyl-diacetylchasmanine (9) and des-N-ethyl-N-formyl-8, 15-dehydro-14-acetylchasmanine (10). Des-N-ethyl-N-formyl-14-acetyl-15-hydroxychasmanine (16) was obtained by epoxy-ring opening reaction of 12. LiAIH4 reduction of 16 gave rise to 15-epi-isodelphonine (17), whose structure was confirmed by X-ray analysis, so that the introduced C15-OH group of 16 was β configuration. In order to invert this C15-OH group, oxidation-reduction procedure was used. Des-N-methyl-N-formyl-14-acetyl-15-dehydroisodelphonine (18) was obtained by Swern's oxidation of 16. LiAIH4 reduction of 18 gave rise to isodelphonine (19) and 15-epi-isodelphonine (17). Thus we have succeeded in the introduction of 15-α-hydroxy group into chasmanine (1). The improved route to isodelphonine (19) was also studied. Compound (8) was methylated to give des-N-ethyl-N-methyl-diacetylchasmanine (42). Pyrolysis of 42 gave des-N-ethyl-N-methyl-8, 15-dehydro-14-acetylchasmanine (43), which was oxidized with OsO4 to give 14-acetyl-15-epi-isodelphonine (44). Compound (44) was also oxidized by Swern's method to give 14-acetyl-15-dehydro-isodelphonine (45). Reduction of 45 with LiAl (OCH3)3H at -70°C gave rise to isodelphonine (19) exclusively. And then, isodelphinine (3) was derived from isodelphonine (19) via intermediates, 14-benzoylisodelphonine (46), 14-benzoyl-15-trichloroethoxycarbonyl-isodelphonine (48) and 8-acetyl-14-benzoyl-15-trichloroethoxycarbonyl-isodelphonine (49). Penduline (50) was also synthesized from chasmanine (1) by use of the latter method.View full abstractDownload PDF (1887K) -
SUMU MATSUEDA, MASAHIKO NAGAKI1984 Volume 104 Issue 7 Pages 753-756
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFrom the mature plants of Artemisia montana, a new sesquiterpenelactone, yamayomoginin (I) was isolated together with the two known sesquiterpenelactones, yomogiartemin (II) and yomogin (III), and a coumarin, scopoletin (IV). The structures of I and its related compound, feddeinin (VI) which was isolated from A. feddei, were also established.View full abstractDownload PDF (454K) -
MICHINORI KUBO, REIKO MATSUDA, HIDEAKI MATSUDA, SHIGERU ARICHI1984 Volume 104 Issue 7 Pages 757-762
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAnti-thrombic activities of 70% methanol extracts obtained from the roots of Panax notoginseng (BURK.) F.H. CHEN were investigated in the experimental model of disseminated intravascular coagulation (DIC). In coagulative system, the 70% methanol extracts at a dose of 200 mg/kg inhibited the decrease of blood platelets and fibrinogen and the formation of hemorrhagic necrosis of liver on endotoxin-induced DIC in rats. In order to clarify the mechanism for DIC, in vitro effects of the 70% methanol extracts and its various fractions on the coagulative system were examined with endotoxin-, collagen-, ADP- and arachidonic acid-induced blood platelet aggregation and conversion of fibrinogen to fibrin induced by thrombin. As a result, the 70% methanol extracts and its ethylacetate soluble portion were found to inhibit the conversion of fibrinogen to fibrin. However, the 70% methanol extracts had no inhibitory effect on blood platelet aggregation. In fibrinolytic system, effects of Panax notoginseng on fibrinolytic activity were examined in rats as determined by euglobulin lysis time and fibrin plate assay. As a result, the 70% methanol extracts at a dose of 200 mg/kg was found to reduce the euglobulin lysis time in rats. And also, the 70% methanol extracts and its n-BuOH soluble portion promoted urokinase action in a plasminogen-containing fibrin plate. On the basis of the in vivo and in vitro experimental results, it is suggested that Panax notoginseng can be considered as having anti-DIC activity. And, one of its mechanism on DIC may be due to the inhibitory effect on conversion of fibrinogen to fibrin and the promotional effect on urokinase action for plasminogen.View full abstractDownload PDF (778K) -
MASAMI KAN, KOHJI OHNISHI, MOTOAKI SHINTANI1984 Volume 104 Issue 7 Pages 763-768
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA strong-base anion exchange resin was mixed with a porous polymer gel modified with hydroxy group to control the exchange capacity, and packed into a small column (3 mm i.d.×50 mm). Anions in a sample solution were separated by this column, by using 0.01 M Na2CO3 as an eluent. After passing through a suppressor column, anions were detected by conductometry. By this method, F-, Cl-, Br-, NO3-, PO45- and SO42- were determined within 15 min. Their detection limits and the coefficient of variation of the method were 0.01-0.8 ppm, and 0.9-1.3%, respectively. By use of the flask combustion technique together with this method, organic halogens (F, Cl, Br) and sulfur were determined.View full abstractDownload PDF (638K) -
MASATOSHI YAMAZAKI, MICHIHIRO IKENAMI, JUN KISUGI, SATORU YUI, SHIGERU ...1984 Volume 104 Issue 7 Pages 769-774
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe present study shows that some selected anti-cancer drugs induce tumor lysis in vitro in cooperation with phagocytic cells (drug-dependent cellular cytotoxicity ; DDCC) and that chemotherapeutic drugs augment the mediator-dependent killing activity of macrophages. Tumor cells pretreated with the drugs were susceptible to phagocytemediated killing. Tumor necrosis serum can also cooperate with some drugs in killing tumor cells. Moreover, some selected drugs can induce cytotoxic macrophages and the quantitative changes of phagocytes such as polymorphonuclear leukocytes. These results suggest that some anti-cancer drugs have the activities of inactivation of tumor cells and/or activation of host cells. Thus, tumor cells may be killed effectively in vivo by anti-cancer drugs through these mechanisms.View full abstractDownload PDF (651K) -
NAHOKO KUROSAWA, SEIJI MORISHIMA, EIJI OWADA, KEIJI ITO, KAORU UEDA, A ...1984 Volume 104 Issue 7 Pages 775-779
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSA simplified method for the monitoring of nifedipine (NF) plasma concentration in patients after therapeutic doses was developed by use of a gas chromatograph equipped with a flame thermionic detector (FTD). After the extraction from the plasma with benzene, the organic layer was evaporated and the residue was dissolved in methanol. An aliquot of the solution was injected into gas chromatograph with OV-17 (3%) column. Diltiazem hydrochloride was used as an internal standard (I.S.). In this method, enough accuracy and precision were obtained in the range of 20-300 ng/ml of plasma NF levels. The detection limit for plasma NF was about 10 ng/ml, which was almost minimum concentration in the usual dosage regimen. This method could be useful not only to monitor the concentration in the plasma but to study the pharmacokinetics of NF in human.View full abstractDownload PDF (497K) -
SHIGEHARU OIE, AKIRA KOSHIRO1984 Volume 104 Issue 7 Pages 780-785
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe bactericidal actions of chlorhexidine alone and in combination with low concentration of ethanol were examined for several organisms already reported to be resistant to chlorhexidine. Of the species tested, Pseudomonas aeruginosa, Acinetobacter calcoaceticus, Providencia stuartii and Proteus mirabilis were completely killed by exposure, for 10 min at 20°C, of 0.02 or 0.5% chlorhexidine, but Flavobacterium meningosepticum and Achromobacter xylosoxidans were resistant to 0.02% chlorhexidine and P. cepacia showed the resistance to both 0.02% and 0.5% chlorhexidine. The concentration of 0.02 or 0.5% chlorhexidine in the presence of 10% ethanol, however, was sufficient to induce a complete loss of viability in the above-mentioned resistant species. The combination of chlorhexidine and diluted ethanol might be useful for the disinfection in hospital practice as this acts synergistically with strong bactericidal activity.View full abstractDownload PDF (619K) -
TSUNEO UMEDA, NORIAKI OHNISHI, TERUYOSHI YOKOYAMA, KOJI KURODA, TSUTOM ...1984 Volume 104 Issue 7 Pages 786-792
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe thermal transition of carbamazepine polymorphic forms (forms I, II, III) in the solid state was investigated by X-ray powder diffractometry. From the kinetic analysis according to the method of Hancock-Sharp, it appears that the transition of form I to form III follows the mechanism of random nucleation and two-dimensional growth of nuclei (Avrami-Erofeev equation). The activation energy for the transition from form I to form III was calculated to be 54.7 kcal/mol from the slope of the Arrhenius plots. On the other hand, the transition of form II to form III will proceed by the mechanism of the two-dimensional diffusion. The activation energy for this transition was calculated to be 31.6 kcal/mol.View full abstractDownload PDF (984K) -
SETSUKO OHTA, MACHIKO FURUKAWA, MASATO SHINODA1984 Volume 104 Issue 7 Pages 793-797
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAfter the investigation of the protective potencies of ferulic acid and related compounds against mice irradiated with soft X-ray, the survival effect was detected in ferulic acid, caffeic acid and isosafrole and the protective potency on skin injury in ferulic acid, ferulic amide, cinnamic acid, isosafrole, linolic acid and oleic acid.View full abstractDownload PDF (483K) -
MASAHIDE KATO, MASAHIKO MARUMOTO, MACHIKO HAYASHI, TOSHIO MAEDA, EIICH ...1984 Volume 104 Issue 7 Pages 798-804
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe effect of Shosaiko-to on the liver injury induced by D-galactosamine was studied in rats. Shosaiko-to (200 mg/kg, i.p.) suppressed markedly increases in serum glutamic oxaloacetic transaminase (GOT) and glutamic pyruvic transaminase (GPT) activities and decreases in hepatic tryptophan pyrrolase and glutamine synthetase activities induced by D-galactosamine The histopathological changes such as hyaline degeneration in the liver of rats injected D-galactosamine were reduced by Shosaiko-to. Daisaiko-to and Saikokeishi-to also suppressed the increase in serum GPT activity induced by D-galactosamine treatment. The active principles of Shosaiko-to were found in fraction which was adsorbed on Amberlite XAD-2 in H2O and eluted with ethanol. The effect of Shosaiko-to on the increase in serum GPT activity was not observed in adrenalectomized rats. From these results, it was suggested that Shosaiko-to suppressed liver injury induced by D-galactosamine and the action of Shosaiko-to might involve in increase in adrenal function.View full abstractDownload PDF (1223K) -
TOSHIHIKO NAGAI, SHOJI YAMADA, MASAHIKO IKEKITA, KAZUYUKI KIZUKI, HIRO ...1984 Volume 104 Issue 7 Pages 805-811
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSProteolytic actions of hog pancreatic elastase I on plasma fibronectin, in vitro, were analyzed by SDS-polyacrylamide gel electrophoresis. The enzyme was incubated with fibronectin, at the ratio of 1 : 100 (w : w) (=molar ratio, 1 : 6), at 37°C, pH 7.4 for various periods. Intact fibronectin molecule (molecular weight : ca. 450 kilodaltons (kd)) was completely digested within 5 min incubation, and five major fragments having the molecular weights of 180, 160, 130, 60, and 25 kd were newly generated. After 4 h incubation, fragments of 180, 160, 130, 60 kd gradually disappeared, and fragments of 75, 50 and 35 kd were newly detected. Two fragments out of these peptide fragments, i.e., 60 and 50 kd fragments retained gelatin-binding activity. It is, therefore, assumed that the 50 kd fragment was derived from the early 60 kd fragment. These elastase activities were suppressed by 150 mM sodium chloride, i.e., even after 2 h incubation, 60 and 130 kd fragments remained in quantity and 75, 50, and 35 kd fragments were not generated. Elastatinal strongly inhibited the proteolytic actions of elastase on fibronectin.View full abstractDownload PDF (1097K) -
AKIRA YAMAJI, YOSHIMI MAEDA, MASAKO OISHI, YOSHIHIKO HIROTANI, HIROE K ...1984 Volume 104 Issue 7 Pages 812-815
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe quantitative analysis of saikosaponins in Chinese medicinal preparations containing Bupleuri Radix was investigated. Saikosaponins-b1 and -b2 in the KOH-MeOH extracts from these preparations were determined by high performance liquid chromatography (HPLC) on LiChrosorb RP-18 column with a mobile phase of MeOH-H2O-AcOH-Et3N (75 : 25 : 0.2 : 0.2). Saikosaponins-a and -d were converted quantitatively into the corresponding -b1 and b2 by mild acid treatment of the extracts, and determined by HPLC method. This methods were applied to pharmaceutical evaluation of seven kinds of Chinese medicinal preparations containing Bupleuri Radix and other miscellaneous crude drugs. The all preparations contained considerable amounts of saikosaponins-b1 and -b2 which were regarded as the secondary products from -a and -d at the manufacturing procedure. Nineteen commercial products of Daisaiko-to and Shosaiko-to contained 33-526 of saikosaponin-a, -281 of -d, 8-449 of -b1 and 5-335 μg/g of -b2.View full abstractDownload PDF (454K) -
TAKESHI MINAMI, KEIICHI SAMUKAWA, KAZUNORI ADACHI, YUKO OKAZAKI1984 Volume 104 Issue 7 Pages 816-818
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSHemodialysis patients were devided into a short-term group, who had been treated for about two years, and a long- term group, who had been treated for about five years. Their serum chromium levels were compared with those of with normal healthy males and females. When the period of hemodialysis treatment had been longer, the serum chromium level was statistically lower in females. The same tendency was also observed in males. This may be caused by the removal of chromium from the serum by hemodialysis treatment. Chromium is an essential trace element and its deficiency symptoms are known. Therefore, when the hemodialysis treatment is extended over a long period of time, we must pay attention to the serum chromium level.View full abstractDownload PDF (398K) -
YOSHIHIKO INAMORI, MAYURI KUBO, YOSHIAKI KATO, MASAHIDE YASUDA, KIMIYE ...1984 Volume 104 Issue 7 Pages 819-821
Published: July 25, 1984
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS3, 3', 4, 5'-Tetrahydroxystilbene (1) isolated from the heartwood of Cassia garrettiana CRAIB showed strong coronary vasodilatory effects on guinea-pigs and hypotensive effects on rats. On the other hand, the coronary vasodilatory effects of derivatives of 1, i.e., 1-tetraacetate (2), 1-tetramethyl ether (3) and 3, 3', 4, 5'-tetrahydroxybibenzyl (4) were lower than that of 1. The hypotensive effect of 4 which was most weak in the coronary effect was far lower than that of 1. It is clear that for coronary vasodilatory effect, both the hydroxyl groups attached to benzene rings and trans-olefin structure are necessary while for hypotensive effect trans-olefin structure is necessary.View full abstractDownload PDF (392K)
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