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Volume 36, Issue 4
Displaying 1-50 of 63 articles from this issue
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SABURO SHIMABAYASHI, MASAKI OKUDA, MASAYUKI NAKAGAKI1988 Volume 36 Issue 4 Pages 1257-1263
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhysicohemical and rheological properties of both concentrated and dilute suspensions of kaolinite were studied in the presence of polyvinylpyrrolidone (PVP). Bingham yield value, relative viscosity with respect to the plastic viscosity, volume fraction of the flow unit, and void fraction in the flow unit for the concentrated suspension were estimated from the flow curve obtained by means of a Couette-type rotary viscometer (Shimadzu UR-1). Mean diameter and volume fraction of the secondary particles in the dilute suspension were measured by a Coulter counter (TA-II). The optimum concentrations of PVP for the flocculation of kaolinite (1-50g/100ml), which were obtained by the two measuring methods mentioned above, were consistent with each other. The more the extent of flocculation increased by virtue of the interparticle bridging effect of PVP, the more the volume fraction of the secondary particles, which is ciscometrically effective, increased although the weight concentration of kaolinite was kept constant. This result shows that the floc is of the open structure, and that the void fraction of the floc increases with the extent of the flocculation. The bulky floc, including much of the suspending medium, behaves as a flow unit in the suspension. The open structure was broken up when an excess amount of PVP as a dispersing agent was added.View full abstractDownload PDF (692K) -
YOSHIHITO OKADA, SHOJI SHIBATA, ANA M. J. JAVELLANA, OSAMU KAMO1988 Volume 36 Issue 4 Pages 1264-1269
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of entada saponins II and IV, isolated from the bark of Entada phaseoloides (L.) MERRILL (Leguminosae), were elucidated as 3-O-[β-D-xylopyranosyl(1→2)-α-L-arabinopyranosyl-(1→6)][β-D-glucopyranosyl(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-28-O-[β-D-apiofuranosyl(1→3)-β-D-xylopyranosyl(1→2)][2-O-acetyl)-β-D-glucopyranosyl(1→4)-6-O-((6R)-6-hydroxy-2, 6-dimethyl-(2E)-2, 7-octadienoyl)-β-D-glucopyranosyl oleanolic acid (1) and entagenic acid (3).View full abstractDownload PDF (609K) -
HIROAKI YANAGISAWA, YUKIO OHSHIMA, YOSHIHITO OKADA, KUNIO TAKAHASHI, S ...1988 Volume 36 Issue 4 Pages 1270-1274
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of a new sesquiterpene glycoside, loquatifolin A (1), isolated from the leaves of Eribotrya japonica (THUNB.) LINDLE, was established to be α-L-rhamnopyranosyl(1→4)-α-L-rhamnopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→6)]-β-D-glucopyranosyl-6, 7-trans-neloridol on the basis of chemical and spectral studies.View full abstractDownload PDF (563K) -
KIMIAKI ISOBE, KUNIHIKO MOHRI, KATSUMI TOKORO, CHIE FUKUSHIMA, FUMIKA ...1988 Volume 36 Issue 4 Pages 1275-1282
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOzonolytic cleavage of o-dimethoxybenzene derivatives to dimethyl Z, Z-muconates is satisfactorily controlled by the addition of boron trifluoride etherate as a regulator. By this oxidation, 3, 4-dimethoxybenxyl alcohol gave an α-pyrone derivative (6) and erythrinan derivatives gave D-seco-erythrinans in appreciable yields.View full abstractDownload PDF (789K) -
CHISATO KANEKO, HIROATSU MATSUMOTO, KEIKO YAMADA, TADAO TAKEUCHI, TAKE ...1988 Volume 36 Issue 4 Pages 1283-1288
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 1-(2-acetoxyethoxy)methyl-5-amino-4-cyanoimidazole (5) with isothiocyanates afforded 3-(2-acetoxyethoxy)methyl-5-(substituted amino)-7-(N-substituted thiocarbamoyl)-iminoimidazo[4, 5-d][1, 3]thiazine (6a-c) at 50°C in dimethylformamide. At more elevated temperature, for example, in refluxing pyridine, compound 5 reacted with methyl isothiocyanate to give 3-2(acetoxyethoxy)methyl-5-methylamino-7-(N-methylthiocarbamoyl)iminoimidazo[4, 5-d][1, 3]-thiazine (6b) and 9-(2-acetoxyethoxy)methyl-1-methyl-6-imino-2-thioxopurine (7b).On the other hand, when carbon disulfide was used in place of isothiocyanates, the reaction afforded 3-(2-acetoxyethoxy)methyl-7-imino-5-thioxoimidaxo]4, 5-d][1, 3]thiazine (8) in refluxing pyridine.Under alkaline conditions, 6 and 8 were found to be rearranged to 2-(substituted amino)-9-(2-hydroxyethoxy)methyl-6-thioxopurine (10) and 2, 6-dithioxo-9-(2-hydroxyethoxy)methylpurine (9), respectively.View full abstractDownload PDF (670K) -
YOSHIO OKADA, YUKO TSUDA, NAOKI TENO, KEIKO WANAKA, MIYAKO BOHGAKI, AK ...1988 Volume 36 Issue 4 Pages 1289-1297
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSActive center-directed peptide inhibitors of plasmin were designed based on the structure of specific substrates of plasmin and synthesized by a conventional solution method. Their effects on plasmin were examined and the structure-activity relationship was studied. D-Ile-Phe-Lys-BZA (4-benzoylanilide) inhibited plasmin activities toward S-2251 and fibrin (IC50 : 0.069mM and 0.18mM respectively) but D-Ile-Phe-Lys-BPP (4-benzylpiperidine amide) was not inhibitory. However D-Ile-Phe-Lys-BZA was cleaved by plasmin to release benzoylaniline, indicating that this type of peptide inhibitor is not stable to plasmin. It was found that Tos-Lys-pNA was not cleaved by palsmin and inhibited plasmin activity toward not only fibrin but also amall peptide substrates and fibrinogen by blocking the active center of plasmin with some selectivity. In order to obtain potent and stable inhibitors of plasmin, it is recommended to design them with reference to the structures of Tos-Lys-pNA and the specific substrate, D-Ile-Phe-Lys-pNA.View full abstractDownload PDF (947K) -
KOSAKU HIROTA, TETSUO TOMISHI, YOSHIFUMI MAKI1988 Volume 36 Issue 4 Pages 1298-1304
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2', 3', 5'-Trichloro-2', 3', 5'-trideoxy-2', 3'-secouridines (2a, b) were synthesized from uridine or 5-fluorouridine by a combination of sodium metaperiodate oxidation, sodium borohydride reduction, and chlorination with Vilsmeier-Haack reagent. Reaction of 2a, b with base gave some new pyrimidine acyclonucleosides (3-5) and (uracil-l-yl)-1, 4-dioxanes (8, 9). The preparation of 5'-chloro-5'-deoxy-2', 3'-secouridine (11) from 5'-chloro-5'-deoxyuridine (10) and its conversion into (uracil-l-yl)-1, 4-dioxane 12 and 5'-deoxy-2', 3'-secouridine (13) are also described.View full abstractDownload PDF (732K) -
TAKAO SAKAMOTO, YOSHINORI KONDO, SHIGEKI IWASHITA, TATSUO NAGANO, HIRO ...1988 Volume 36 Issue 4 Pages 1305-1308
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of N-(2-bromophenyl)-and N-(2-iodophenyl)methanesulfonamide with terminal acetylenes in the presence of dichlorobis(triphenylphosphine)palladium yielded 1-methylsulfonyl-indoles having carbon-functional groups at the 2-position, such as hydroxmethyl, 2-hydroxyethyl, diethoxymethyl, 2-ethoxycarbonylethyl, etc., in one step.View full abstractDownload PDF (485K) -
YOSHINOBU MUROFUSHI, MISAKO KIMURA, YASUTERU IIJIMA, MITSUO YAMAZAKI, ...1988 Volume 36 Issue 4 Pages 1309-1320
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwenty kinds of 6-substituted and five kinds of N1-substituted griseolic acid derivatives were synthesized. The inhibitory activities of these compounds towards adenosine 3', 5'-cyclic monophosphate (cAMP) and guanosine 3', 5'-cyclic monophosphate (cGMP) phosphodiesterase (PDE) were investigated to clarify the structure-activity relationship. Substitution at the 6-position of griseolic acid caused a change of PDE IC50 from 0.16 to 206μM against cAMP PDE. Substitution at the N1-position also caused a change of PDE IC50 from 0.16 to 127μM against cAMP PDE.View full abstractDownload PDF (1326K) -
TERUYUKI MIYAMOTO, JUN-ICHI MATSUMOTO1988 Volume 36 Issue 4 Pages 1321-1327
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new and convenient synthesis of 4-hydroxycinnoline-3-carboxylate derivatices was developed. Reactions of ethyl 2-diazo-3-(2, 4, 5-triflurophenyl- and 2, 3, 4, 5-tetrafluorophenyl)-3-oxopropionates (2a and 2c) with tri-n-butylphosphine afforded ethyl 6, 7-difluoro- and 6, 7, 8-trifluoro-4-hydroxycinnoline-3-carboxylates (5a and 5c) and ethyl 2-hydrazono-3-(2, 4, 5-trifluoro-phenyl- and 2, 3, 4, 5-tetrafluorophenyl)-3-oxopropionates (6a and 6c), respectively. When triphenylphosphine was used, the reaction of 2a-c afforded[[l-ethoxycarbonyl-2-oxo-2-(halogenated phenyl)ethylidene]hydrazono]triphenylphosphoranes (3a-c), which were hydrolyzed to give the corresponding hydrazones 6a-c. An alternate and efficient synthesis of 5a and 5c was accomplished by an intramolecular cyclization of 6a and 6c, respectively. A base-catalyzed cyclization of the methylhydrazone 7 gave ethyl 7-chloro-6-fluoro-1-methyl-1, 4-dihydro-4-oxocinnoline-3-carboxylate (8). Possible mechanisms for the reaction of 2 leading to 5 are discussed.View full abstractDownload PDF (732K) -
IKUO SAKURAI, SAKAE SHIMIZU, YUZURU YAMAMOTO1988 Volume 36 Issue 4 Pages 1328-1335
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new metabolites, named macommelinal, macrophin and macrophic acid, were isolated from the culture broth of Macrophoma commelinae IFO 9570. Their structures were determined to be 2-(4-methoxy-6-methyl-2-oxo-2H-pyran-5-yl)ethanal, 3-methyl-2-butenoic acid (E)-[5-hydroxymethyl-4-methoxy-6-(2-methoxycarbonylethenyl)-2-oxo-2H-pyran-3-ly]methyl ester and 3-(4-methoxy-3, 5-dimethyl-2-oxo-2H-pyran-6-yl)-2-propenoic acid, respectively. 4 Acetyl-3-methoxy-5-methylbenzoic acid, now named macrophomic acid, was also isolated from a large-scale culture.The biosynthesis of the macommelin group, novel 5-substituted 2-pyrone metabolites, has been investigated by feeding experiments with [1-13C]-, [1, 2-13C2]- and [1-13C, 2-2H3]acetate and [2-13C]malonate. It was concluded that all these metabolites originated from a single straight tetraketide chain. Furthermore, the biogenetic mutual relationships of these metabolites including potential intermediates were estabished through incorporation experiments with 14C-labeled compounds.View full abstractDownload PDF (798K) -
YOSHITAKA OHISHI, YOSHIO DOI, TERUO NAKANISHI1988 Volume 36 Issue 4 Pages 1336-1342
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Elimination of stereoisomeric cis- and trans-3-hydroxy-2-nitro-2, 3-dihydrobenzo[b]furans was investigated. The 2, 3-dihydrobenso[b]furans were stable under acidic conditions but were easily dehydrated under basic conditions to afford the corresponding 2-nitrobenzo[b]furans. An (ElcB)R mechanism is proposed on the basis of several lines of evidence obtained from studies on kinetics, ultraviolet spectra, leaving group effect and deuterium isotope effect in the elimination reaction.View full abstractDownload PDF (726K) -
A Stereocontrolled Synthesis of (±)-Emetine and (±)-Protoemetinol by Intramolecular Michael ReactionYOSHIRO HIRAI, TAKASHI TERADA, ATSUSHI HAGIWARA, TAKAO YAMAZAKI1988 Volume 36 Issue 4 Pages 1343-1350
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn intramolecular Michael reaction of 9 stereoselectively gave the tricyclic compound (10), which was converted to (±)-protoemetinol (2) and 13. Compound 13 is an important intermediate for the synthesis of (±)-emetine. A simpler preparation of 13 was also carried out by the intramolecular Michael reaction of 14, followed by reduction of the ketone moietv. Furthermore, the stereoselective formation of 26, which is an intermediate for the synthesis of (±)-emetine, was achieved by the floowing sequence of reactions : intramolecular Michael reaction, of the ketone moiety, and removal of the N-carbomethoxy group.View full abstractDownload PDF (825K) -
TAKESHI IMANISHI, MASAYUKI YAMASHITA, MUNETAKA MATSUI, FUSAKO NINBARI, ...1988 Volume 36 Issue 4 Pages 1351-1357
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS7, 7-Dimethyl-5-(2-propenyl)tricyclo[3.3.0.02, 8]octan-3-one (4) was prepared from 4, 4-di-methyl-2-cyclopentenone in several steps. The Birch reduction of 4 resulted in exclusive formation of a bicyclo[3.3.0]octanone (14)through C2-C8 bond clevage, while its substitutional reactions yielded bicyclo[3.2.1]octanones (15) through C1-C2 bond cleavage as major products.View full abstractDownload PDF (801K) -
KOUJI OKANO, YUKAKO MIZUHARA, HIROSHI SUEMUNE, HIROYUKI AKITA, KIYOSHI ...1988 Volume 36 Issue 4 Pages 1358-1365
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDuring a detailed examination on the cyclization of 1, 4-diketones to cyclopentenones, we have found that two oxygenated products (4 and 5) are formed when the purification by column chromatography on silica gel takes a long time. The highly functionalized cyclopentenone (4a) obtained as the major product in this manner seems to be an attractive synthon for the synthesis of natural products. For eaxmple, the chiral synthon (1S, 4S)-4-benzyloxycarbonyl-1, 4-dihydroxy-2-methoxycarbonyl-3-methyl-2-cyclopentene ((+)-7) with high optical purity was obtained by microbial reduction with Rhodotorula rubra CCY 20-7-1, and the absolute stereochemistry was established independently by using the exciton chirality method and the chemical method.View full abstractDownload PDF (810K) -
SHINJI FUSHIYA, FUMIE WATARI, TAKASHI TASHIRO, GENJIRO KUSANO, SHIGEO ...1988 Volume 36 Issue 4 Pages 1366-1370
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new acidic amino acid was isolated from a Basidiomycetes, Lactarius piperatus (Fr.) S. F. GRAY. The structure of this compound has been determined as 2(S), 3'(S)-1-(3-amino-3-carboxy-propyl)-5-oxo-2-pyrrolidinecarboxylic acid (1) on the basis of nuclear magnetic resonance analysis and chemical synthesis.View full abstractDownload PDF (570K) -
TAKESHI IMANISHI, MASAYUKI YAMASHITA, FUSAKO NINBARI, TETSUAKI TANAKA, ...1988 Volume 36 Issue 4 Pages 1371-1378
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA total synthesis of (±)-pentalenene (3), one of the least-oxidized triquinane sesquiterpenes, is described. By a several-step sequence, 4, 4-dimethyl-2-cyclopentenone (5) was derived to a tricyclooctanone (4), which was subjected to a reductive C2-C8 bond opening reaction to give 15. The triquinane derivative (20), obtained from 15, was transformed to (±)-pentalenene (3) and (±)-epi-pentalenene (21) in a 1.8 : 1 ratio.On the other hand, hydroboration-oxidation of 4 followed by tosylation gave easily separable products, 23 and 24, which were transformed to 20A and 20B, precuesors for (±)-3 and (±)-21, respectively.View full abstractDownload PDF (831K) -
KOUJI OKANO, HIROSHI SUEMUNE, KIYOSHI SAKAI1988 Volume 36 Issue 4 Pages 1379-1385
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis paper describes formal syntheses of the title compounds from the easily prepared chiral synthon (+)-5. One of the structural features of the cuparene family is the presence of vicinal quaternary carbons on the five-membered ring. The quaternary carbon with the tolyl function could be constructed by stereoselective 1, 4-addition of (p-tolyl)2 Zn to(+)-5. The key intermediate β-ketol (13), obtained from (+)-5 via a sequence of reactions, was successfully applied to formal syntheses of the title compounds.View full abstractDownload PDF (690K) -
TOSHIKI TANAKA, YASUKI YAMADA, MORIO IKEHARA1988 Volume 36 Issue 4 Pages 1386-1392
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn N-monomethoxytrityloxyethyl or-hexyl group was introduced onto the 5'-phosphoryl group of N-protected-3'-benzoyldeoxynucleosides. After 3'-O-debenzoylation and phosphitylation, they were converted 3'-phosphoramidite derivatives. These were used at the last coupling reaction in the synthesis of octadecadeoxynucleotides with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester method on long-chain alkylamine controlled pore glass beads. Partially deblocked oligomers, after thiophenol and ammonia treatment, were separated rapidly on a reversed-phase C-18 silica gel column by utilizing the hydrophobic nature of the monomethoxy-trityl group. After AcOH treatment, the octadecamers with an aminoethyl or aminohyxyl group at the 5' end were obtained and then coupled with a fluorescent compound. The ultraviolet-temperature profiles were measured after hybridization with a complementary oligonucleotide.View full abstractDownload PDF (745K) -
MEI LIN GO, TONG LAN NGIAM1988 Volume 36 Issue 4 Pages 1393-1398
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe change in hydrophobicity on N-oxidation of the ring nitrogen of quinoline and its 4-amino derivatives was determined by the shake-flask method and reverse phase liquid chromatography (RPLC), buffered at an appropriate pH. Hydrophobicity was expressed as log partition coefficient (log P) (shake flask) or log capacity factor in 100% water (log kw) (RPLC). It was found that the ring nitrogen, when unprotonated, was less polar than the corresponding N+-O- fragment of the N-oxide. When protonated however, the N+-H fragment was more polar than the N+-O- fragment. Correlationship was observed vetween the log P and log kw values of six phenolic compounds of the series. The derived Collander-type equation was log P=-6.78+3.73log kw (n=6, r=0.972).View full abstractDownload PDF (651K) -
JUN NAKANO, MITSUO MIMURA, MITSUO HAYASHIDA, MASAHIRO FUJII, KAZUHIKO ...1988 Volume 36 Issue 4 Pages 1399-1403
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe optical isomers of 2-acetyl-7-(2-hydroxy-3-isopropylaminopropoxy)benzofuran hydrochloride (1a, b) (befunolol·HCl) were synthesized by using (S)-1, 2-O-isopropylideneglycerol (4) as a common chiral building block, and their β-adrenergic blocking activities were examined. The (S)-(-)-isomer 1b was about 300 times more potent than the (R)-(+)-isomer 1a on an atrial preparation.View full abstractDownload PDF (536K) -
TAKAYUKI NAMIKI, YUKIHISA BABA, YASUTAKA SUZUKI, MOTOAKI NISHIKAWA, KO ...1988 Volume 36 Issue 4 Pages 1404-1414
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious analogues of WF-3681 (1a), a novel aldose reductase inhibitor, were synthesized and examined for aldose reductase-inhibitory activity. It was found that the carboxylic acid function is necessary and the side-chain length is important for the activity. Furthermore, the lipophilicities of the benzene ring and the enol ether group are significant for increasing the activity.View full abstractDownload PDF (861K) -
FUMIE MIZUI, RYOJI KASAI, KAZUHIRO OHTANI, OSAMU TANAKA1988 Volume 36 Issue 4 Pages 1415-1418
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGrains of Quinoa, Chenopodium quinoa (Chenopodiaceae), have been used as a staple food in the Andes, South America. From brans of grains of this plant, five new saponins were isolated and their structures were elucidated as 28-O-β-glucopyranosyl esters of hederagenin 3-O-β-glucopyranosyl-(1→3)-α-arabinopyranoside and 3-O-β-glucopyranosyl-(1→3)-β-galactopyranoside, and 28-O-β-glucopyranosyl esters of phytolaccagenic acid 3-O-α-arabinopyranoside, 3-O-β-glucopyranosyl-(1→3)-α-arabinopyranoside and 3-O-β-glucopyranosyl-(1→3)-β-galactopyranoside.View full abstractDownload PDF (472K) -
YOSHIKATSU YAGUCHI, NOBUKO SAKURAI, MASAHIRO NAGAI, TAKAO INOUE1988 Volume 36 Issue 4 Pages 1419-1424
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new diarylheptanoid glycosides (1 and 2) were isolated together with vanillic acid and six known triterpenoids, maslinic acid, alphitolic acid, arjunolic acid, myricolal, oleanolic acid and oleanolic acid acetate, from the stem bark of Myrica rubra SIEB. et ZUCC. (Myricaceae). On the basis of spectral and chemical evidence, the structures of 1 and 2 were established as myricanol 5-O-β-D-(6'-O-galloyo)-glucopyranoside and myricanol 5-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside, respectively.View full abstractDownload PDF (660K) -
KIYOSHI ZAITSU, MASAO NAKAYAMA, YOSUKE OHKURA1988 Volume 36 Issue 4 Pages 1425-1430
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive [3-(2-pyridyldithio)propionoyl]insulins (PDP-insulins) were separated preparaticely from the reaction mixture of porcine insulin with N-succinimidyl 3-(2-phyidyldithio)propionate by means of anion-exchange high-preformance liquid chromatography on a TSK gel DEAE-SW column. Horseradich peroxidase (HRP)-insulin conjugates (GlyAl-HRP-insulin, LysB29-HRP-insulin and GlyAl, LysB29-diHRP-insulin) were prepared by the reaction of thiolated HRP and the corresponding PDP-insulins and purified by gel-permeation high-performance liquid chromatography on a TSK gel G3000SW column.View full abstractDownload PDF (575K) -
YASUHIKO MATSUKI, JUNKO DAN, KATSUHARU FUKUHARA, TOMIHARU ITO, TOSHIO ...1988 Volume 36 Issue 4 Pages 1431-1436
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe principal metabolites of meclomen (sodium meclofenamate; sodium 2-[(2, 6-dichloro-3-methylphenyl)]aminobenzoate monohydrate) were isolated from human urine and characterized by gas chromatography-mass spectrometry (GC-MS) and proton nuclear magnetic resonance (1H-NMR) spectroscopy together with the Folin-Ciocalteu test. Oxidation occurred at the methyl group at C-3 and/or the aromatic ring in meclomen, yielding the methylol (M-1), dicarboxylic acid (M-2), phenols (M-3 and M-4), 3-hydroxymethylated phenol (M-7), 3-demethylated phenol (M-6) and phenolic dicarboxylic acid (M-8).Among these metabolites, M-1, M-2, M-3 and M-4 are common to fenamate antiinflammatory analgesics. A novel metabolite, M-6, is presumably produced from M-8 through M-7 or M-2 as an intermediate.View full abstractDownload PDF (577K) -
HIROAKI NANBA, HISATORA KURODA1988 Volume 36 Issue 4 Pages 1437-1444
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen tumor-bearing mice were given diet containing fruit bodies of mushroom (Agaricus bispora) (M-feed), the tumor growth was suppressed to 66.8% in the case of MM-46 carcinoma in C3H mice and to 53.2% in the case of IMC carcinoma in CDF1 mice. To elucidate the mechanism of this action, the effect of M-feed on the macrophages against syngeneic tumor cells was studied : it was found that the phagocytic activity was increased about 2.2 times and the cytotoxicity of macrophages was enhanced 1.4 times. The production of superoxide anion by macrophages from tumor-bearing mice was decreased in mice given the normal feed, while in mice maintained on the M-feed, it was increased by 1.3 times. Furthermore, the cytotoxic activities of lymphokine-activated killer cells and cytotoxic T cells were invreased 1.4 and 1.5 times, compared with their counterparts from mice fed on the mushroom-free diet. These results suggest that mushroom powder given orally acts not only by activation of various effector cells to attack tumor cells, but also by potentiating the cellular functions and preventing a decrease of immune functions of the tumor-bearing host.View full abstractDownload PDF (760K) -
SUSUMU OGUSHI, KIMINORI NAGAO, SHIGENORI EMI, MAKOTO ANDO, DAISUKE TSU ...1988 Volume 36 Issue 4 Pages 1445-1450
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSarcosine oxidase (EC 1.5.3.1) of Arthrobacter ureafaciens was purified to homogeneity by means of sequential chromatography on DEAE-Toyopearl 650M, Toyopearl HW-55, and hydroxyapatite. The purified enzyme was most active at pH 8.3 and was stable at pH 6.5-9.5 for 20h at 20°C. The molecular weight of the enzyme was estimated to be 185000 by gel filtration. Sodium dodecylsulfate-polyacrylamide gel electrophoresis indicated that the enzyme was composed of four dissimilar subunits with molecular weights of 96000, 45000, 23000, and 14000 daltons. The isoelectric point was 4.5 as checked by isoelectrofocusing. The Km and kcat values for sarcosine were 6.4mM and 5.8s-1. The enzyme was strongly inactivated by heavy metal ions such as Ag+, Zn2+, Cu2+, Hg2+, Co2+, and Cd2+, and an SH-blocking regent, p-chloromercuribenzoate. Spectrophotometric and fluorogenic analyses suggested that a flavin cofactor associated with the 45000-dalton subunit participates in the enzyme reaction.View full abstractDownload PDF (639K) -
HIDENORI HAYASHI, FUMIE HASHIMOTO, KAZUYO NAKATA1988 Volume 36 Issue 4 Pages 1451-1455
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe membrane fluidity of liver peroxisomes from normal and clofibrate-treated rats was investigated by using a fluorescence probe, 1-anilinonaphthalene-8-sulfonate (ANS). The excitation maximum of the probe was changed from 347 to 380 nm and the emission maximum from 493 to 463 nm in the presence of peroxisomes, and fluorescence intensity was enhanced more than 50 times. These results suggest that ANS was bound to the peroxisomal membrane. Fluorescence depolarization (P-value) was determined with such ANS-labeled peroxisomes. The P-values of peroxisomes from both normal and clofibrate-treated rats gradually decreased with increasing temperature, but that of clofibrate-treated peroxisomes was always smaller than that of normal peroxisomes. Pvalues were observed at 37°C for 60 min. The average P-value of normal peroxisomes was 0.270, while that of clofibrate-treated peroxisomes was 0.248. These results indicate that the membrane fluidity of liver peroxisomes in increased by the treatment with clofibrate. Treatment of rats with another inducer of liver peroxisome proliferation, di(2-ethylhexyl)phthalate, had an effect similar to that of clofibrate. However, alloxan-treated (diabetic) rats showed no change of peroxisomal membrane fluidity.View full abstractDownload PDF (504K) -
TADASHI YOSHIMOTO, HIROSHI OYAMA, NOBUHIRO KORIYAMA, DAISUKE TSURU1988 Volume 36 Issue 4 Pages 1456-1462
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyolyl endopeptidase (EC 3.4.21.26) was purified from bovine testis by chromatographies on carboxymethyl (CM)-cellulose, diethylaminoethyl (DEAE)-Sephadex, hydroxyapatite, p-chloro-mercuribenzoate (PCMB)-Sepharose and Sephadex G-150. The enzyme appeared homogeneous as judged by disc gel electrophoresis. The molecular weight of the enzyme was estimated to be 76000 be gel filtration. The optimum pH of the activity was 7.2. The enzyme was inactivated with diisopropylphosphorofluoridate, Z-Gly-Pro-CH2Cl, Z-Pro-prolinal and o-chloromercuribenzoate. The enzyme hydrolyzed biologically active peptides at the carboxyl side of prolyl residues. ALl of the characteristics of the testis prolyl endopeptidase are quite similar to those of the enzymes isolated from bovine brain, liver, kidney and muscle. These enzymes were immunologically indistiguishable : the antiserum raised against bovine brain enzyme a fused precipitation line against the enzymes from bovine testis, brain, liver and kidney, and the testis and brain enzymes gave the same immunoelectrophoretic profile.View full abstractDownload PDF (797K) -
SUSUMU KAWASHIMA, YOSHIKAZU HIROSE, KUNIHIKO YABU, HIROSHI FUJIWARA1988 Volume 36 Issue 4 Pages 1463-1468
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn this study, the rectal absorption of bacampicillin hydrochloride (BAPC) in rabbits as a model was investigated with the aim of preparing efficacious suppositories. First, analytical methods, were developed to determine penicillins in plasma for evaluating the absorption of BAPC. When BAPC was mixed in the plasma, BAPC was not detected only ampicillin (ABPC) derived from BAPC was detected by high performance liquid chromatographic analysis. The bioavailability of BAPC was studied following oral and rectal administration in rabbits. Administration of a BAPC suppository formulated with Witepsol H-15 produced absorption at a level 80% of that found after oral dosing, whereas no measurable level was seen following rectal administration of an ABPC suppository correspinding to the BAPC dose. Further, rectal absorption of BAPC increased with increasing dose and a prolonged plasma level was observed.View full abstractDownload PDF (616K) -
HIDEAKI SATO, YUICHIRO KUROSAKI, KIYOTO EDO, MICHINAO MIZUGAKI1988 Volume 36 Issue 4 Pages 1469-1474
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMany tricyclic antidepressant drugs such as imipramine hydrochloride showed high extraweak chemiluminescence (CL) with similar emission spectra. Iminodibenzyl and N-methylimino-dibenzyl, compounds saturated at the 10-11 bond, generated high CL, whereas iminostibene, a compound unsaturated at the 10-11 bond, did not. Mechanisms of CL produced by autoxidation of imipramine hydrochloride were investigated. The existence of the imipramine radical and the imipramine peroxy radical during the autoxidation were supported by an electron spin resonance study. A possible pathway is proposed for CL generation from imipramine hydrochloride by autoxidation.View full abstractDownload PDF (560K) -
SUSUMU KAWASHIMA, HAYATO NAKAZAWA, HIROSHI FUJIWARA1988 Volume 36 Issue 4 Pages 1475-1482
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRectal administration of bacampicillin hydrochloride (BAPC) in Witepsol H-15 base suppository provided a fairly good absorption in rabbits; the extent of bioavaliability was 44%. Since BAPC has high lipophilicity compared to the parent compound (ampicillin, ABPC), rectal absorption from hydrophilic bases (macrogol 1000 and/or 4000) was examined. The highest bioavailability (88%) was obtained with macrogol 1000 base, but the bioavailability devreased with the invrease of macrogol 4000 base addition. It is known that macrogol bases increase the secretion of rectal fluid while oleaginous bases fo not change the amount of the fluid. The solubility of BAPC, however, was constant regardless of the amount and kind of the macrogol bases. In contrast, the partition coefficients (toluene/water) were reduced by the addition of both kinds of macrogol bases. Furthermore, the release rates of BAPC from the suppositories were little affected by the addition of the bases. Therefore, macrogol 1000 base seemes to improve the bioavalability by prolonging absorption with an invrease of the distribution area in the rectum. On the other hand, macrogol 4000 base is assumed to reduce the bioavailability by taking up secreted rectal fluid to dissolve and/or by forming a highly viscous solution.View full abstractDownload PDF (789K) -
KOICHI AKIMOTO, KAORI KUROSAKA, HIROSHI NAKAGAWA, ISAO SUGIMOTO1988 Volume 36 Issue 4 Pages 1483-1490
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photo-stability of nifedipine and its 4- or 1, 4-substituted derivatives in methanol was studied. A ferrioxalate actinometer was used to measure cumulative numver of photons as an index of light intensity. Under irradiation with a high-pressure mercury lamp, the photo-stability decreased in the order : l-hydroxy-4-(m-nitrophynyl) compound, 4-(p-nitrophenyl) compound, 4-(m-nitrophynyl) compound, l-methyl-4-(o-nitrophynyl) compound and nifedipine itself. The 4-phenyl compound and 4-(o-chlorophenyl) compound did not decompose in the range to 4×1021 quanta. Further, the photo-stability of nifedipine was quantitatively examined under sunlight, a fluorescent lamp and a high-pressure mercury lamp. The slopes of the linear plots of residual percent against cumulative number of photons irradiated through a UV-D33S colored glass filter were essentially the same for all three light sources. On the other hand, the slopes did not agree in the case of direct exposure without a filter. A good correlation between extent of photo-degradiation and integrated illumination (lux×h) was not observed with or without the filter. By means of this actinometry with a UV-D33S colored glass filter, the l-hydroxy-4-(m-nitrophenyl) compound and 4-(m-nitrophenyl) compound were quantitatively estimated to be more photo-stable than nifedipine by factors of 270 and 76, respectively, under a given light source.View full abstractDownload PDF (770K) -
YOSHINOBU FUKUMORI, YUMIKO YAMAOKA, HIDEKI ICHIKAWA, TOMOAKI FUKUDA, Y ...1988 Volume 36 Issue 4 Pages 1491-1501
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Wurster process (Glatt GPCG-1) could produce particles whose outer layer consisted of fine phenacetin particles (70% under 20μm) adhering to or fixed on lactose particles (90μm), when a mixture of both powders was fluidized and sprayed with a binder solution. The enteric coating of layered particles was performed with an aqueous methacrylic acid-ethylacrylate (MA-EA) copolymer suspension (Eudragit L30D-55).The simple MA-EA microcapsules of coarse lactose crystals (120μm) exhibited a delayed release characterized by a lag time in the JP XI disintegration 1st fluid (pH 1.2), as previously reported. The layered phenacetin and hydroxypropylcellulose used as the binder in this study had no significant effect on the delayed relase of lactose. However, phenacetin was released according to biphasic zero-order kinetics, different from the case of directly coated coarse crystals (128μm). The apparent dissolution rate increased after the first slow release. The formation of a fine phenacetin suspension within microcapsules after the dissolution of lactose accounted for such an enhanced release.When polvinylpyrrolidone (PVP) was used as the binder, the lag times of the release of phenacetin and lactose were remarkably prolonged. The release rate of phenacetin after the lag time increased. The water intake into the microcapsules enhanced by PVP, which induced an extremely large expansion of the particles, and the reduction of viscosity accounted for these phenomena.The results showed that when PVP was used as the binder, the enteric coating through the layering process was sufficiently protective against the release of both phenacetin and lactose at the 50% coating level.View full abstractDownload PDF (1081K) -
YASUAKI OGAWA, MASAKI YAMAMOTO, SHIGEYUKI TAKADA, HIROAKI OKADA, TSUGI ...1988 Volume 36 Issue 4 Pages 1502-1507
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolylactic acid (PLA) or copoly(lactic/glycolic) acid (PLGA) microcapsules containing leuprolide acetate were prepared by an in-water drying process and the release patterns were examined in vitro. The release rates were extremely small from microcapsules prepared with PLA of average molecular weight 22500, and from microcapsules prepared with PLGA having average molecular weight 21200 and a copolymer ratio of 75/25 (molar ratio of lactic acid to glycolic acid). The release rate of leuprolide acetate from the microcapsules prepared with PLA of average molecular weight 6000 was relatively fast, but was still too slow to give the desired drug level over one month. Several water-soluble compounds were incorporated into microcapsules prepared with PLA of average molecular weight 22500, in an attempt to increase the release rate by the creation of aqueous channels. These compounds only induced a high initial release and failed to increase drug release. The release profile of the drug from microcapsules prepared with PLGA of average molecular weight 14000 and a copolymer ratio of 75/25 was ideal for one month's release. A small initial release was observed followed by a steady release which lasted for 35d, and approximately followed zero-order kinetics.View full abstractDownload PDF (788K) -
MARIKO NAGATA, TOSHIHISA YOTSUYANAGI, KEN IKEDA1988 Volume 36 Issue 4 Pages 1508-1513
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe disintegration kinetics of egg phosphatidylcholine small unilamellar liposomes (SUV) in sodium deoxycholate (SDOC) and sodium cholate (SC) was investigated as a mimic of the disintegration behavior of orally administered liposomes in the intestine. The disintegrating action of the bile salts was followed by measuring turbidity changes with a stopped-flow apparatus, from which the pseudo-first-order disintegration rate constant (kobs) was calculated as a function of bile salt concentration (up to 25mM). The disintegration rate of the SUV in SDOC was considerably higher than that in SC, and the kobs increased with a tendency to reach a plateau in SDOC but not in SC. At 20 mM bile salts, the disintegration half-life of the SUV (1.5 mM phosphorus) was 0.003s in SDOC and was 0.69s in SC. A model in which the penetration-saturation step of bile salt molecules and the subsequent lamellar-micellar transition step are involved was applied to analyses of the disintegration kinetics. The results showed that SDOC molecules penetrate into the bilayer structure faster than SC molecules by a factor of 5×102. This is probably due to the difference of molecular surface avaliable for hydrophobic interaction.View full abstractDownload PDF (612K) -
KYOKO TAKAHASHI, TADANORI MAYUMI, TAKEO KISHI1988 Volume 36 Issue 4 Pages 1514-1518
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to test the hypothesis that coenzyme Q10 (CoQ10) might prevent myocardial cell uptake of doxorubicin (DX), 3H-DX uptake in cultured myocardial cells was studied. When cultured myocardial cells were incubated with 3.5μM DX for 24-72h or 140μM DX for 1-4h, 120μM CoQ10 added in advance protected their beating from DX toxicity. However, CoQ10 had no effect on 3H-DX uptake by the cells under the above condition (3.5μM DX for 24-72h or 140μM DX for 1-4h). Most of the radioactivity in the cells was recovered as DX itself in both the medium with and without CoQ10. Furthermore, the effects of a CoQ homolog (coenzyme Q9 (CoQ9)) or an analog (plastoquinone (PQ9)) on the best inhibition by DX were compared using this system. It was shown that CoQ9 prevents, though only partially, the inhibition of the myocardial cell beating by 3.5μM DX. PQ9 was without effect. It is suggested that the protective effect of CoQ10 against DX cardiotoxicity was not caused by inhibition of DX uptake or by alteration of DX metabolism in the cells.View full abstractDownload PDF (588K) -
KENJI SUGIBAYASHI, MASABUMI NEMOTO, YASUNORI MORIMOTO1988 Volume 36 Issue 4 Pages 1519-1528
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to measure the effect of several penetration enhancers on the percutaneous absorption of drugs and to classify the enhancers into several categories in terms of the mode and mechanism of action, in vitro permeation experiments with a model drug, indomethacin, from aquenous, ethanolic and binary solvent systems were carried out by using excised hairless rat abdominal skin and a 2-chamber diffusion cell at 37°C. Among the enhancers used in the present experiments, Azone, dimethyl sulfoxide (DMSO), isopropylmyristate, diethylsebacate, diethylmethylbenzamide, methylpyrrolidone and salicyclic acid enhanced the skin permeation of indomethacin, whereas urea, pyrrolidonecarboxylic acid and sodium hyaluronate did not as compared with the same solvent system without enhancer. These results suggest that the lipophilicity of enhancers may be an important factor for the penetration-enhancing effect on the skin permeation of indomethacin. It is also suggested that the effect of methylpyrrolidone is dependent upon the kind of solvent system; higher water content resulted in a lower effect.Further experiments to clarify the mechanism of action were done with pyrrolidones and salicylates, since it has already been reported that other enhancers such as Azone and DMSO might mainly affect the lipid in skin. Pyrrolidones had an in vitro moisturizing effect on keratin tablets and an in vivo skin-moisturizing effect. They affected the dissolution of keratin powder. On the other hand, salicylates dissloved and softened keratin powder, but they had no effect on the skin moisturizing. These results suggest that pyrrolidones and salicylates affect the keratin cells in the stratum corneum to enhance skin permeability, although the mechanism of action is different between the two groups.View full abstractDownload PDF (928K) -
ASTUKO NOSE, TADAHIRO KUDO1988 Volume 36 Issue 4 Pages 1529-1533
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAromatic nitro, azoxy, azo and hydrazo compounds were reduced with the sodium borohydride-nickel boride system to the corresponding reduction products under mild conditions.View full abstractDownload PDF (506K) -
TAIKO ODA, TOMOKO MURAI, YOSHIHIRO SATO1988 Volume 36 Issue 4 Pages 1534-1539
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe carbon-13 unclear magnetic resonance chemical shift assignments for meso-hexestrol (1a), made on the basis of two-dimensional 13-1H chemical shift correlation, long-range selective 1H decoupling experiment, and a reported two-dimensional Fourier-trasform experiment for long-range proton-carbon-13 spin coupling constants, are reported. For measurement of carbon-protoncoupling constants of meso-hyxestrol derivatives (1b-e, 2a-d, 3a-c, and 4), the coupling informaiton was detected by using a gated decoupling facility which permitted retention of the nuclear Overhauser enhancement and a long-range selective 1H decoupling experiment. The results showed that the aromatic carbon resonances are influenced by the structure (no double bond, or one or two double bond(s)) of the hexane framework in the central portion.View full abstractDownload PDF (651K) -
TAKAO NARUI, KUNIO TAKAHASHI, SHOJI SHIBATA1988 Volume 36 Issue 4 Pages 1540-1544
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 1, 3, 3-Tetramethylurea (Me4U) promotes the alkylation of α-D-glucans and prevents caramelization and side reactions in acetolysis and acid hydrolysis of α-D-glucans even at high reaction temperatures. This might be caused by strong intermolecular hydrogen bondings between hydroxyls of carbohydrates and the carbonyl group of Me4U, which prevail over intramolecular hydrogen bondings between the alcoholic hydroxyls. The hydrogen bondings as such induce deformation of the rigid higher structure of polyglucans to promote the alkylation, while they protect hydroxyls from side reactions during the course of modified acetolysis and acid hydrolysis even at high temperature to produce oligosaccharide fragments in good yields.In the present study the interaction betwen Me4U and hydroxyls of glucans has been demonstrated by means of proton and carbon-13 nuclear magnetic resonance (1H- and 13C-NMR) spectroscopy.The 1H- and 13C-NMR spectra of carbohydrates remain unchanged even after heating for 30 min at 160°C in the presence of d12-Me4U in d6-dimethyl sulfoxide, whereas without d12-Me4U in the medium, heating the solution causes remarkable changes.View full abstractDownload PDF (439K) -
YOSHIKI KASHIWADA, GEN-ICHIRO NONAKA, ITSUO NISHIOKA, MAKOTO NISHIZAWA ...1988 Volume 36 Issue 4 Pages 1545-1549
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo major stilbene glucosides (1 and 2) have been newly isolated from Chinese rhubarb (commercial name : Gaoh, second grade), and characterized on the basis of chemical and spectroscopic evidence as piceatannol 4'-O-β-D-glucopyranoside (1) and its 6"-O-gallate (2). In addition, high-preformance liquid chromatographic analysis has led to the characterization of minor components including sennoside, anthraquinones, and other stilvenes.View full abstractDownload PDF (478K) -
MICHIYO HIZUKA, NORIYUKI HAYASHI, TOMOKO KAMASHITA, HIROSHI SUEMUNE, K ...1988 Volume 36 Issue 4 Pages 1550-1553
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 6-Dioxabicyclo[3.3.0]octan-3, 7-dione seems to be a promising compound for the synthesis of natural products such as epoxyeicosatrienoic acid, laurediol, and eldanolide. This compound, consisting of two γ-lactones, could be prepared by double lactonization of the silver salt of trans-3-hexenedioic acid using iodine. Starting with this bis-lactone, (±)-eldanoide could by synthesized in a stereocontrolled manner.View full abstractDownload PDF (468K) -
JASENKA MATULIC ADAMIC, KYOICHI A. WATANABE1988 Volume 36 Issue 4 Pages 1554-1557
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDi-O-tert-butyldiphenylsilyl (BDPS)-thymidine (2) was converted to α-bromo-3', 5'-di-O-BDPS-thymidine (3) by photobromination. Crude 3 was hydrolyzed to the α-hydroxythymidine derivative 4 which was oxidized with MnO2 to the 5-formyluracil nucleoside 5. Fluorination of 4 with diethylamino-sulfur trifluoride afforded the protected α-fluorothymidine 6. Similarly, 5 was converted into the α, α-difluorothymine nucleoside 7. These protected fluorothymidines (6 and 7) were deblocked by treatment with tetra-n-butylammonium fluoride to give α-fluorothymidine(8, F-TDR) and α, α-difluorothymidine (9, F2-TDR).View full abstractDownload PDF (469K) -
CATHERINE RUBAT, PASCAL COUDERT, JACQUES COUQUELET, PIERRE BASTIDE, JE ...1988 Volume 36 Issue 4 Pages 1558-1561
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo methods of N-substitution were applied to 5-arylidene-6-methyl-3-(4H)-pyridazinones. The resulting derivatives were tested in order to determine the area of pharmacological activity. Most compounds exhibited a dose-dependent analgesic activity. Introduction of a benzoyl substituent in the 2-position of the pyridazinone ring 2j induced the most potent activity.View full abstractDownload PDF (442K) -
HIDEHIKO HAGA, TERUMI NAKAJIMA1988 Volume 36 Issue 4 Pages 1562-1564
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnalysis of aldoses and alditols by capillary gas chromatography as alditol trifluoroacetates was carried out by using a fused silica capillary column (cyanopropyl-bonded phase) and a hydrogen flame ionization detector. Seventeen alditols were completely resolved within 18 min. The detection limits were about 1-4 ng/injection which are one hundred times smaller than as those of a packed column. Special care was necessary in the use of internal standards for the simultaneous determination of multiple components, and good reproducibility was obtained by using double internal standards.View full abstractDownload PDF (398K) -
HIROKAZU MATSUNAGA, TAKAHSI FUJIMOTO, RIICHI TAWA, SHINGO HIROSE1988 Volume 36 Issue 4 Pages 1565-1570
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA reversed-phase (RP) liquid chromatography procedure using column switching was applied to assay one of the aminoglycoside antibiotics, sisomicin. The drug in serum was derivatized with o-phthalaldehyde (OPA) and β-mercaptopropionic acid (β-MP) in 0.05M borate buffer (pH 9.0), then directly injected onto a RP pre-column (ODS-silica, 50×4 mm i.d.) to remove protein and interfering compounds (confirmed by ultraviolet monitoring at 280nm). The sisomicin derivatives retained on the pre-column were desorbed by back-flushing onto an analytical column (5μm ODS-silica 200×4mm i.d.) with 0.05M potassium dihydrogen phosphate-0.05M disodium hydrogen phosphate buffer (pH 7) and were separated by elution with a mixture of methanol, ethylene glycol and counter ion solution (sodium 1-heptanesulfonate/acetic acid/water, 2.5g/42ml/208ml). This system could be utilized for more than 50 samples with a 1ml injection volume. A good linear response curve was found between the injected sample amounts and the peak heights for the concentration range of 0.5 to 5μg/ml of sisomicin. The limit of detection for sisomicin in serum was 62.5.ng/ml for 0.1ml of sample. The mean recovery from serum was 97.5%.View full abstractDownload PDF (548K) -
TAKAHSHI FUJIMOTO, RIICHI TAWA, SHINGO HIROSE1988 Volume 36 Issue 4 Pages 1571-1574
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple method for the determination of sisomicin (SISO) in dried blood spots (DBS) on filter paper has developed. SISO in DBS was recovered most effectively by ultrasonication in 0.05M KH2PO4-borate buffer (pH 9.0). The eluates from the DBS were treated with a carboxymethyl-Sephadex column, followed by determination be reversed-phase high-performance liquid chromatography after pre-column fluorescence derivatization using o-phthalaldehyde and β-mercaptopropionic acid in 0.05M KH2PO4-borate buffer (pH 9.0). The detection limit of SISO was below 0.05μg per ml of whole blood (100μl). The method permits a simple blood collection method for monitoring of aminoglycoside antibiotics at therapeutic levels.View full abstractDownload PDF (416K) -
YOSHIE KITAMURA, MIKA DONO, HIROSHI MIURA, MICHIYASU SUGII1988 Volume 36 Issue 4 Pages 1575-1576
Published: April 25, 1988
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProduction of swertiamarin in various cultured tissues of Swertia pseudochinensis was investigated. This bitter glucoside was not detected in callus, root or leaf cultures, whereas regenerated plants from callus contained it. Swertiamarin contents in the regenerated plants were compared with those in the original plant.View full abstractDownload PDF (319K)