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Volume 108, Issue 8
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TSUTOMU FURUYA1988 Volume 108 Issue 8 Pages 675-696
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDe novo synthesis and biotransformation of secondary metabolites by plant cell cultures have been studied in my laboratory for about 25 years. Incorporation of traditional and advanced tissue culture techniques, i.e. chemical and physical regulations, engineering of apparatus, selection of high-yielding starins and hairy root cultures transformed with Ri plasmid, has made possible the successful production of;ginseng saponins (ginsenoside Rb1 and Rg1), morphinan alkaloids (morphine and codeine), berberine, caffeine, vitamin E, retrochalcone (echinatin) and so on. Furthermore, a large scale production of ginseng cells in 20 ton tank, morphinan alkaloid synthesis in redifferentiated poppy cells, and detection of 6'-deoxychalcone synthase activity in licorice cells have firstly been demonstrated.The biotransformational ability of cultured plant cells has been examined, employing terpenoids (citronellal, menthol, borneol, etc.), steroids (cardiac glycosides, pregnane derivatives and androgens), alkaloids (isoquinoline and indole) and phenolics (phenylpropionic acid, tropic acid, etc.) as substrates. Bioreactors with immobilized plant cells have been also developed. The reactions including oxidation, reduction, glycosylation, esterification, methylation and isomerization against administered compounds have been observed, and, consequently, even optical resolution of racemic substrates could be performed. De novo synthesis of plant products and biotransformation of organic compounds by plant cell cultures will contribute to plant bioindustry by providing medicinals and other useful compounds.View full abstractDownload PDF (2682K) -
TAISUKE ITAYA1988 Volume 108 Issue 8 Pages 697-715
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBy use of the Wittig reaction with the phosphorane derived from L-serine the chiral synthese of the fluorescent bases isolated from eukaryotic phenylalanine transfer ribonucleic acids have been achieved. The key intermediate for the syntheses has been also obtained by means of palladium-assisted coupling with N-(methoxycarbonyl)-L-vinylglycien. "Fission and reclosure of the adenine ring" has permitted the syntheses of the target compounds for the parent nucleosides of some of these characteristic tricyclic bases. Rate studies on the hydrolysis of unusually labile glycosidic bonds of these nucleosides and related compounds have been also summarized.View full abstractDownload PDF (1367K) -
KYUJI ABE, HIROZUMI INOUE, TAKU NAGAO1988 Volume 108 Issue 8 Pages 716-732
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSSynthetic and pharmacological studies of diltiazem hydrochloride, a representative calcium antagonist widely used for the treatment of ischemic heart disease all over the world, have been reviewed. 3-Hydroxy-1, 5-benzothiazepine derivatives were synthesized for evaluting central nervous system (CNS) activities, but our original random screening test revealed that these compounds have a potent coronary vasodilating effect without significant influence on CNS. Out of them, diltiazem ((+)-(2S, 3S)-2, 3-dihydro-3-acetoxy-2-(4-methoxyphenyl)-5-[2-(dimethylamino)ethyl]-1, 5-benzothiazepin-4(5H)-one hydrochloride) was selected as the compound to be developed. As a result of various investigations, 2-3-cis-2, 3-dihydro-2-(4-methoxyphenhyl)-3-hydroxy-1, 5-benzothiazepin-4(5H)-one, a key intermediate for the synthesis of diltiazem, has been successfully synthesized in high yield via regio- and stereo-selective opening of the oxirane ring of 3-(4-methoxyphenyl)glycidic ester with 2-nitrothiophenol in the presence of tin-catalyst. In the course of studies on the mechanism of its vasodilating action, we found that diltiazem has a calcium antagonistic property. We reviewed the pharmacological bases or features of diltiazem for its anti-anginal, anti-hypertensive and antiarrythmic effects. Its effects on calcium channels, as well as on renal and cerebral circulation, were also mentioned. In addition, new possible indications, and domestic and international development of diltiazem were briefly described.View full abstractDownload PDF (1354K) -
TSUTOMU OHASHI, KENJI TOKUNO, YUKARI OTODA1988 Volume 108 Issue 8 Pages 733-739
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe methylation of several organic potassium salts with 10-methylthioxanthenium tetrafluoroborate (2) was investigated in a solid state. The ground mixture of 2 and each one of the potassium salts of benzoic acid, p-nitrobenzoic acid, phthalimide, 1, 2-benzisothiazol-3(2H)-one 1, 1-dioxide, 2-acetyl-2, 3-dihydro-1H-inden-1-one, and 2-acetyl-1, 2, 3, 4-tetrahydronaphthalen-1-one was prepared. The temporal change of each ground mixture was followed by an infrared spectroscopy and an X-ray diffraction analysis at room temperature, 40°C, and 70°C. On standing at proper temperature the ground mixtures of 2 with each one of the above potassium salts in an agate mortar, the infrared spectroscopy and the power X-ray diffraction analysis indicate the appearance of the corresponding peaks attributable to a methylation product, the demethylated product (thioxanthene), and the ion exchanged product (KBF4) in a process of time. Next, the difference of the state of each mixture and the effet of grinding were confirmed by means of the differential thermal analysis. It turned out that the reaction temperature changed from the region of high to that of low with increasing grinding time. The solid-state reactions of 2 with free benzoic acid, and phthalimide did not proceed. From the facts described above, in the solid-state reaction of 2 with organic potassium salts, it became clear that every reaction gave methylation compound by the attack of the organic anion to the methyl group with the formation of the ion exchanged KBF4, moreover, the grinding activated the reaction system and facilitated the methylation at relatively low temperature.View full abstractDownload PDF (709K) -
HIROSHI WADA, NOBUTOSHI TANAKA, TAKAO MURAKAMI, TOKIKO UCHIDA, KOZO KO ...1988 Volume 108 Issue 8 Pages 740-744
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAn unusual flavanone derivative named hariganetin (I) was isolated from the fronds of Wagneriopteris japonica LOEVE et LOEVE (Thelypteridaceae), together with desmethoxy-matteucinol (II), matteucinol (III), methoxymatteucin (IV), matteucinol 7-O-β-D-glucoside (V) and 5-O-caffeoylshikimic acid. The structure of hariganetin (I) was determined by spectroscopic methods and X-ray analysis.View full abstractDownload PDF (532K) -
SUSUMU NISHIZAWA, AKIHISA YOSHIMI, HIROYUKI MURO, MASAYASU KASAI, SATO ...1988 Volume 108 Issue 8 Pages 745-753
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSBifunctional pro-drugs of 7-(D-mandelamido)-3[[(5-methyl-1, 3, 4-thiadiazol-2-yl)thio]-methyl]-3-cephem-4-carboxylic acid (KY-087), incorporating both lipophilic and hydrophilic pro-moieties, were designed to improve the oral absorption of KY-087, a cephalospolin with a broad spectrum of antibacterial activity. The synthesized pro-drugs were found to possess a sufficient aqueous solubility and an optimal lability. The pro-drugs were evaluated for the oral absorption in mice. Among the pro-drugs tested, KY-109 carring a (5-methyl-2-oxo-1, 3-dioxol-4-yl)methyl (DOX) pro-moiety and an L-alanyl pro-moiety was particularly well absorbed orally and, as expected, displayed good antibacterial activity in the experimental infection in mice.View full abstractDownload PDF (926K) -
MIKIO YAMAZAKI, YUMIKO SATOH, SHO ITO1988 Volume 108 Issue 8 Pages 754-757
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe inhibitory potency towards monoamine oxidase (MAO : EC 1.4.3.4) was assayed for 33 species of tropolone related compounds. The tropolne skeleton itself had hardly participated in MAO inhibitory action, while the functional groups had affected the potency of the compounds. Azulene, a hydrocarbon with unsubstituted 5- and 7-carbon rings, inhibited MAO in the mouse liver competitively, and its IC50 was 59.0μM. The inhibition constants (K1) of azulene for MAO in the mouse liver was 12.5 μM.View full abstractDownload PDF (424K) -
YORISHIGE IMAMURA, YUICHIRO KOJIMA, MASAKI OTAGIRI1988 Volume 108 Issue 8 Pages 758-762
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe metabolic reduction of acetohexamide was examined by using the rat liver and kidney. This reduction activity was observed in both the microsomal and cytosolic fractions of these tissues. The Km and Vmax values for the reduction activity in the microsomal fractions of the liver and kidney were higher than those in the cytosolic fractions. The optimum pH for acetohexamide reduction activity in the microsomal and cytosolic fractions of the liver were 4.5 and 5.0, respectively, but those of the kidney ranged from 6.0 to 7.0 Furthermore, the sensitivities to various inhibitors were different among the microsomal and cytosolic fractions of the liver and kidney. These findings indicate the heterogeneity of acetohexamide reducing enzymes in the microsomal and cytosolic fractions of the rat liver and kidney.View full abstractDownload PDF (589K) -
MASAHIRO HORIBA, KAZUO AKIMA, TOYOJI HASE, TADASHI ARIKA, KOHJI AMEMIY ...1988 Volume 108 Issue 8 Pages 763-771
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSExcretion and distribution of sizofiran (SPG), an antitumor polysaccharide, were investigated after a single intravenous (i.v.) injection of 14C-labelled SPG(14C-SPG) to rats. Radioactivity was very slowly eliminated from the body. It was mainly excreted in the urine. When 14C-SPG was given at doses of 0.2mg and 2 mg/kg, the radioactivity recovered in the urine within 6 months was 41% and 26%, respectively. Radioactivity much less than urinary excretion was also observed in the feces and expired gas. In whole-body autoradiographic study, radioactivity was distributed selectively in the reticuloendotherial tissues such as liver, spleen, mesenteric lymph node and bone marrow at 24 h after dosing, and still remained to be considerably high in the spleen, lymph node, liver and thymus at six months after dosing. SPG-like substances, isolated from the livers, spleens and mesenteric lymph nodes of rats given non-radioactive SPG, seemed to have a similar chemical structure to that of SPG and were shown to have a similar potent antitumor activity to that of SPG against sarcoma-180 murine tumor.View full abstractDownload PDF (832K) -
IKUO KANAMOTO, MASATO KODACHI, ISAMU HORIKOSHI, TAMOTSU KOIZUMI1988 Volume 108 Issue 8 Pages 772-776
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe effect of saikokeishi-to (SK) on the pharmacokinetics of phenytoin in rabbit was studied. After 10 d-administration of chronic SK to rabbit, total plasma clearance (CL) of phenytoin increased and terminal phase half-life (T1/2, β) decreased significantly. On the other hand, volume of distribution at steady-state (Vss) and protein binding of phenytoin in the plasma did not change between before and after SK treatment. And SK treatment also increased CL of antipyrine by 31%. These results suggested that SK treatment induced hepatic drug-oxidizing enzyme.View full abstractDownload PDF (507K) -
TOSHIO FUJITA, AKIRA KOSHIRO1988 Volume 108 Issue 8 Pages 777-787
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe stability of flomoxef, an oxacephem antibiotic, was studied in various buffer solutions and intravenous admixtures. Degradation in buffer solutions at 25°C and ionic strength of 0.6 obeyed pseudo first-order kinetics. Excluding the effects of buffer salts by extrapolation to zero buffer concentration, pH-rate profile was obtained. From the general rate law as a function of hydrogen ion concentration, t0.9 at pH4-8 was predicted to be 32-37h. The apparent activation energies at pH3, 6 and 9 were 12.6, 20.0 and 27.2 kcal mol-1, respectively. Studies on stability in various infusions and 5% glucose admixtures indicated the acceleration of degradation in amino acids infusions, admixtures of aminophylline, tegafur and 5-fluorouracil injections. The interactions of flomoxef with tegafur and/or 5-fluorouracil injections were studied in carbonate buffer with or without glucose at pH9.0. The results suggested that the reaction of flomoxef with glucose predominated over those with ingredients of 5-fluorouracil or tegafur injections, namely tromethamine or carbonate molecules. Thus, the injections with high pH are incompatible with flomoxef and related antibiotics, especially in large volume injections containing glucose as well as another carbohydrates. But if sufficient dilution of active components or adjustment of pH of the admixtures below 6 could be attained, one can use in safe and usefully even the above incompatible combinations.View full abstractDownload PDF (851K) -
HIDEO NAKAMURA, SATORU MOTOYOSHI, YASUHIRO SETO, TOSHIAKI KADOKAWA1988 Volume 108 Issue 8 Pages 788-793
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSAnti-inflammatory, analgesic, antipyretic and gastrointestinal ulcerogenic activities of metabolites of bermoprofen (AD-1590), a new non-steroidal anti-inflammatory drug, were investigated in order to ascertain whether they have pharmacological activities in experimental animals. Among 3 metabolites of AD-1590, main metabolite, 11-hydroxyl form (AD-2406) was the most active in the carrageenan-induced hind paw edema in rats, and the others weak or almost inactive at a dose of 80mg/kg, i.v. Anti-edema, analgesic (mouse phenylquinone and rat acetic acid writhing tests) and antipyretic (LPS febrile rabbits) activities of intravenously administered AD-2406 were approximately one-hundredth that of AD-1590 (0.04-1 mg/kg, i.v.), but equivalent or superior to that of oral aspirin. On the other hand, AD-2406 did not produce significant gastric ulcer in fasted rats in lethal toxic dosages, and its acute lethal toxicity (LD50=373mg/kg, i.v.) was about one-second that of oral AD-1590 in fed rats. These results suggest that AD-2406 and 2 other metabolites do not contribute the pharmacological activities produced by AD-1590.View full abstractDownload PDF (560K) -
KEN YASUKAWA, MICHIO TAKIDO, MIEKO TAKEUCHI, SHIGEKI NAKAGAWA1988 Volume 108 Issue 8 Pages 794-796
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSGlycyrrhizin and caffeine inhibited the action of tumor promoter in mouse skin correspondingly to the effect of quercetin. Glycyrrhizin and caffeine inhibited the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation, and these markedly suppressed the promoting effect of TPA on skin tumor formation in mice initiated with 7, 12-dimethylbenz[a]anthracene.View full abstractDownload PDF (418K) -
KAZUMI MORIKAWA, MASAMITSU HONDA, TOMOKO MATSUMOTO, KO-ICHI ENDOH, KEN ...1988 Volume 108 Issue 8 Pages 797-800
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe antitumor activities of (2-aminomethylpyridine)oxalatoplatinum (II) (I), (2-aminomethylpyridine) (1, 1-cyclobutanedicarboxylato)platinum (II) (II), (2-(1-aminomethyl)phyridine)oxalatoplatinum(II) (III) and (2-(1-aminopropyl)pyridine)oxalatoplatinum (II) (IV) were evaluated against colon 26 carcinoma. The activity was exhibited in ip-ip system, but scarcely in sc-ip system. On the other hand, it was observed that their free platinum complexes decreased quickly in vitro when they reacted with plasma protein. From the result, it was suggested that I, II, III and IV exhibited less antitumor activity in systemic system because they formed their plasma protein complexes with no antitumor activity before reaching the cancer cell.View full abstractDownload PDF (418K) -
HIROYUKI FUJINO, SHUJIRO GOYA1988 Volume 108 Issue 8 Pages 801-803
Published: August 25, 1988
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEstriol in pregnancy urine was determined by reversed-phase high-performance liquid chromatography using precolumn fluorescence derivatization with 1-(dichloro-1, 3, 5-triazinyl)-2-methylisoindole(DTMI). After preliminary acid hydrolysis and extraction of the free estriol, the extract is reacted with DTMI to give the corresponding fluorescent product. The coefficient of variation in within-run precision was 3.7-6.5% for the full extraction and derivatization procedure for estriol from pregnancy urine.View full abstractDownload PDF (367K)
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