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Volume 47, Issue 8
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Masao INUKAI, Masakatsu YONESE1999 Volume 47 Issue 8 Pages 1059-1063
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPreparation methods for the alginate (Alg) gel membranes were deceloped and characterized. Three kinds of Alg gel membrane (mannuronate/guluronate ratio (M/G ratio)=1.00, 0.43, and 0.19) were prepared by a casting method, and the effects of M/G on characteristics such as transmittancy, viscoelasticity, effective charge densities, and drug permeability were investigated. The water content and membrane thickness of the Alg gel membranes were not affected by the M/G ratio, however, transmittancy and viscoelasticity were found to be significantly affected by them. Charge densities (θ) were obtained using a membrane potential method, and these θ valuse increased with M/G ratio, and dissociation of the carboxylic groups of uronates was found to be suppressed significantly in the network. The permeability coefficients (P) of sodium benzoate through the membranes decreased with increasing M/G ratio. The P values are discussed in terms of electrostatic interaction, structure of the gel network, and bound and restricted water.View full abstractDownload PDF (793K) -
Karine JOUVE, Felix PAUTET, Monique DOMARD, Houda FILLION1999 Volume 47 Issue 8 Pages 1064-1067
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(E)-5-(N-Benzylformimidoyl)-4-methylthiazole 3 was prepared in good yield from 5-formyl-4-methylthiazole and benzylamine. Treatment of 3 with methylchloroformate in the presence of ethyldiisopropylamine in refluxing toluene has generated o-quinodimethane (o-QDM) 4. In situ trapping of the latter with acetylenic or quinonoid dienophiles directly afforded the aromatized products 5, 6, 7 and 9. An unprecedented elimination of N-car-bomethoxybenzylamine occurred from the primary dihydro or tetrahydro cycloadducts. Starting from ethyl-propynoate or juglone 8a, the single regioisomer 6 or 9a was obtained, while when using 2- or 3-bromojuglone 8b or 8c the reaction regiospecifically gave 9a or 9b. Calculations by the semi-empirical method PM3 indicated that the regiochemistry observed connot be predicted by the frontier orbital coefficients theory for a concerted electrocyclic reaction, but is better explained by an attack of the nucleophilic end of diene 4 on the more electron deficient carbon of the dienophiles.View full abstractDownload PDF (562K) -
Koji URAKAMI, Naoshige AKIMOTO, Koji NISHIJIMA, Yutaka KITANAKA, Midor ...1999 Volume 47 Issue 8 Pages 1068-1072
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA copoly (DL-lactic/glycolic acid) (PLGA), with a weight-average molecular weight of about 8400, has been characterized using fast atom bombardment (FAB)-tandem mass spectrometry in order to determine the sequence. Because of the large molecular size, PLGA was partially hydrolyzed and the terminal hydroxyl groups in the resulting oligomer mixture acetylated as the indicator. The FAB spectrum of this sample showed a complex ion signal pattern containing monomer to octamer. Diagnostic product ions containing useful information for sequence determination were observed in collision-induced dissociation-MS/MS and MS/MS/MS of these oligomer ions. The results of analysis for dimers through pentamers showed that they have random sequences of lactic and glycolic acid, suggesting that the whole structure of PLGA also has a random sequence.View full abstractDownload PDF (676K) -
Susumu IGARASHI, Takenori KIMURA, Ryo NAITO, Hiromu HARA, Masahiro FUJ ...1999 Volume 47 Issue 8 Pages 1073-1080
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a search for novel nonsteroidal inhibitors of human prostatic 5α-reductase, we found a new series of phenoxybenzoic acid derivatives to be potent human prostatic 5α-reductase inhibitors. Among them, 4-(biphenyl-4-yloxy)benzoic acid derivatives (2n, YM-31758), 2o and 2s showed more potent inhibitory activities than finasteride with IC50 values of 0.87, 0.67 and 0.56nM, respectively. The optimized structures for the phenoxybenzoic acid derivatives 2d-2i were calculated by molecular modeling analysis, and the favorable distance between the carbon of the carboxyl group and the centroid of the phenyl group (benzene ring C) was found to be in the 9-11Å range.View full abstractDownload PDF (1040K) -
Masayasu KASAI, Satoru HATANO, Meiko KITAGAWA, Akihisa YOSHIMI, Ken-ic ...1999 Volume 47 Issue 8 Pages 1081-1088
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCeftizoxime (CZX), a parenteral cephalosporin, has potent and broad antibacterial activity. To improve its oral absorption, we synthesized a series of monofunctional and bifunctional prodrugs of CZX. In rabbits, urinary recovery after oral administration of CZX was improved by esterification of the carboxyl group at the C-4 position with various lipophilic moieties (monofunctional prodrugs), and was further increased by introduciton of a hydrophilic L-alanine to the amino group on the thiazole ring at the C-7 position (bifuncional prodrugs). Least-squares analysis showed good parabolic correlatoins between log P and urinary recovery for monofunctional and bifunctional prodrugs, respectively. AS-924, a bifunctional prodrug with a pivaloyloxymethyl and L-alanyl moiety had the best balance of lipophilicity and water-solubility for oral absorption among the prodrugs synthesized.View full abstractDownload PDF (1085K) -
Yoshio OKADA, Shima JOSHI, Noriyuki SHINTOMI, Yukihiro KONDO, Yuko TSU ...1999 Volume 47 Issue 8 Pages 1089-1096
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 2-adamantyloxycarbonyl group was employed for the protection of the ε-amino group of Lys and the hydroxyl group of Tyr, and the 2-adamantyl ester was employed for the protection of the β-carboxyl group of Asp in order to construct eight peptide segments as building blocks for the preparation of peptide fragments related to the sequence of Sulfolobus solifataricus Ribonuclease. The usefulness of the above protecting groups developed in our laboratory was confirmed.View full abstractDownload PDF (1296K) -
Yuko TSUDA, Shima JOSHI, Noriyuki SHINTOMI, Yukihiro KONDO, Kazuko OHG ...1999 Volume 47 Issue 8 Pages 1097-1101
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSegment condensations were performed to construct peptide fragments related to Sulfolobus solifataricus Ribonuclease. At each condensation step, the new protecting groups were stable. The protected peptide fragments were treated with a low-high HF procedure to give the desired peptide fragments. These peptide fragments were also prepared by the solid-phase method, and the obtained peptides were compared with those obtained by the solution method.The peptide fragments obtained by the solution method were identical with those obtained by the solid-phase method on analytical HPLC, indicating that the new protecting groups could be easily removed by HF, and no racemization occurred during the synthesis of the protected peptides.View full abstractDownload PDF (817K) -
Hideki ICHIKAWA, Yoshinobu FUKUMORI1999 Volume 47 Issue 8 Pages 1102-1107
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA negatively thermosensitive drug-release microcapsule with hydroxypropyl cellulose (HPC) coat was designed and its preparation was carried out by using an air suspension coating technique (the Wurster process). The microcapsule had a core of calcium carbonate, a drug layer of carbazochrome sodium sulfonate (model drug), a subcoat of temperature-insensitive, water-insoluble ethylcellulose (EC), a thermosensitive layer of HPC having a lower critical solution temperature (LCST) and an overcoat of EC. Three different grades of commercial HPC were used. No significant thermosensitivity of drug release was found in the microcapsules (MCs) without the overcoat of EC. However, MCs having the overcoat showed a negative thermosensitivity : the release rate suddenly decreased at temperatures close to the spectrophotometrically determined LCST of each dilute HPC sulution. These results demonstrated that by simply constructing an LCST polymer layer sandwiched between EC membranes, devices exhibiting negatively thermosensitive drug-release could by obtained in the form of fine microcapsules and the temperature dependence of release could be altered depending on the solution properties of the polymers used.View full abstractDownload PDF (1086K) -
Shuji YASUIKE, Shin-ichi SHIRATORI, Jyoji KURITA, Takashi TSUCHIYA1999 Volume 47 Issue 8 Pages 1108-1114
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFully unsaturated group 14 (Si, Ge, and Sn), group 15 (P, As, Sb, and Bi) and group 16 (S, Se, and Te) 2-trimethylsilyl-1-benzoheteropines (16a-j), including the first isolated examples of bismepines, have been prepared by reaction of the corresponding electrophilic metal reagents (MX2 or MX4; M=group 14, 15, and 16 heavier elements) with the key 1, 6-dilithium intermediate (9), generated from the common starting compound (Z, Z)-1-bromo-4-(2-bromophenyl)-1-trimethylsily-1, 3-butadiene (14) by treatment with tert-butyllithium. The trimethylsilyl group in 16b-j was readily removed by treatment with tetrabutylammonium fluoride to give the desired C-unsubstituted 1-benzoheteroepines (1b-j). Single crystal X-ray analyses of 1d (P) and 1f (Sb) revealed that the seven-membered rings exist in boat conformations with the heteroatoms at the bows. All obtained C-unsubstituted group 15 and 16 1-benzoheteroepines (1d-j) were thermolabile in solution towards heteroatom extrusion, while heteroepines (16d-j) having the bulky trimethylsilyl group at the 2-position were much more stable than 1d-j. The half-lives of 1d-j estimated from 1H-NMR spectral analysis indicate that the thermal stabilities of 1d-j decrease in the order 1f (Sb)>1d (P)>1e(As)>1g(Bi) in the group 15 heteroepines and 1j (Te)<1i (Se)>1h (S) in the group 16 heteroepines.View full abstractDownload PDF (955K) -
Mitsuru SATOH, Naoki TAKEUCHI, Takashi FUJITA, Katsuya YAMAZAKI, Tsuyo ...1999 Volume 47 Issue 8 Pages 1115-1116
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnacardic acids, 6-pentadecadienylsalicylic acid and 6-[8(Z)-pentadecatrienyl]salicylic acid were synthesized from aldehyde and acetoacetate with 1, 2-addition.View full abstractDownload PDF (382K) -
Kentaro KOGURE, Otomo OKUDA, Chiharu NAKAMURA, Kyoko HAYASHI, Masaharu ...1999 Volume 47 Issue 8 Pages 1117-1120
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo obtain informaiton about the factors governing spontaneous inter-membrane protein transfer, we examined the effects of incorporation of various amphiphilic compounds in dimyristoylphosphatidylcholine (DMPC) liposomes on protein transfer from influenza virus-infected cells to the liposomes, and analyzed the physical properties of these liposome membranes. The incorporation of amphiphilic compounds, negatively charged divetylphosphate (DCP), dipalmitoylphosphatidylserine (DPPS) or positively charged dimethyldipalmitolammonium (DMDPA), into DMPC liposomal membranes enhanced protein transfer. The liposomes containing DCP, DPPS or DMDPA were unaffected by osmotic shock caused by external addition of glucose, suggeting a decrease in lipid packing in the liposomal membranes. Furthermore, calorimetric study of these liposomes showed that a phase separation occurred partially in the liposomal membranes. Accordingly, the membranes of DMPC liposomes containing DCP, DPPS and DMDPA should be distorted due to the coexistence of two phases, gel and liquid crystalline, in the membranes. Consequenctly, the membrane distortion could be responsible for the enhancement effects of the amphiphiles on the inter-membrane protein transfer from influenza virus-infected cells to the liposomes.View full abstractDownload PDF (762K) -
Tsutomu HATANO, Hiroshi UEBAYASHI, Hideyuki ITO, Sumiko SHIOTA, Tomofu ...1999 Volume 47 Issue 8 Pages 1121-1127
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThirteen phenolic glycosides including six new compounds were isolated from seeds of Cassia tora (Leguminosae). The structures of the new compounds, rubrofusarin triglucoside (7), nor-rubrofusarin gentiobioside (9), demethylflavasperone gentiobioside (10), torachrysone gentiobioside (11), torachrysone tetraglucoside (12) and torachrysone apioglucoside (13), were elucidated on the basis of spectroscopic and chemical evidence. The effects of the phenolic glycosides, their aglycones and several other compounds structurally related to them on Escherichia coli K12, Pseudomonas aeruginosa PAO1 and some strains of Staphylococcus aureus were then examined. Among them, torachrysone (15), toralactone (16), aloe-emodin (18), rhein (19) and emodin (20) showed noticeable antibacterial effects on four strains of methicillin-resistant Staphylococcus aureus with a minimum inhibitory concentration of 2-64 μg/ml. On the other hand, the phenolic compounds tested did not show strong antibacterial effects on E. coli and P. aeruginosa.View full abstractDownload PDF (1027K) -
Fumiko ABE, Hitomi FUJISHIMA, Yukiko IWASE, Tatsuo YAMAUCHI, Kazuhiko ...1999 Volume 47 Issue 8 Pages 1128-1133
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEleven pregnanes were isolated from the hydrolysate of the CHCl3 extract fractionated from the caules of Hoya carnosa. Among these, six pregnanes, including 19-acetoxydigipurpurogenin II, were new, and their structures were elucidated. The structures of twenty new pregnane tetraosides and pentaosides, named hoyacarnosides A-T, besides three known ones from the CHCl3 extract, were determined.View full abstractDownload PDF (786K) -
Kaname KIMURA, Miho Y. MIZUTANI, Nobuo TOMIOKA, Yasuyuki ENDO, Koichi ...1999 Volume 47 Issue 8 Pages 1134-1137
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe docking structure of bryostatin 1, a potent activator of protein kinase C (PKG), to the crystal structure of PKCδ cys2 domain was examined computationally. Prior to the docking study, possible conformers of the 20-membered ring of bryostatin 1 were searched by the high-temperature molecular dynamics calculation method. For each conformer thus identified, the most stable docking model to PKC was searched without any presumptions, covering all possible binding modes and ligand conformations, using our automatic docking program ADAM. Among the seven conformers, the conformer with a ring conformation almost identical to that in the crystal (root mean square deviation=0.187Å) yielded the most stable PKC-bryostatin 1 complex. The bryostatin molecule fits well to the cone-shaped bottom of the PKC binding cavity, forming four hydrogen bonds with main chain groups. On the basis of this docking structure, the structure-activity relations of various bryostatins are well explained.View full abstractDownload PDF (806K) -
Junichi KITAJIMA, Kaoru KIMIZUKA, Yasuko TANAKA1999 Volume 47 Issue 8 Pages 1138-1140
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the methanolic extract of Ficus pumila LINN. fruit (Moraceae), two new acetylated dammarane-type triterpenoids (3, 4) and their two new related compounds (1, 2) were obtained, and their structures were determined by spectral methods as 3β-acetoxy-22, 23, 24, 25, 26, 27-hexanordammaran-20-one (1), 3β-acetoxy-20, 21, 22, 23, 24, 25, 26, 27-octanordammaran-17β-ol (2), 3β-acetoxy-(20R, 22E, 24RS)-20, 24-dimethoxydammaran-22-en-25-ol (3) and 3β-acetoxy-(20S, 22E, 24RS)-20, 24-dimethoxydammaran-22-en-25-ol (4).View full abstractDownload PDF (480K) -
Atsuko FUKUMIZU, Yoko TSUDA, Keiko WANAKA, Mayako TADA, Shosuke OKAMOT ...1999 Volume 47 Issue 8 Pages 1141-1144
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPseudo-peptide analogs of trans-4-aminomethylcyclohexanecarbonyl-L-phenylalanyl-4-aminophenyl acetic acid (PKSI-527, plasma kallikrein selective inhibitor), in which an amide bond (peptide bond) has been replaced by a CH2-NH bond, i.e. trans-4-aminomethylcyclohexanecarbonyl-L-phenylalanyl-Ψ(CH2-NH)-4-aminophenyl acetic acid (I), trans-4-aminomethylcyclohexanecarbonyl-Ψ(CH2-NH)-L-phenylalanyl-4-aminophenyl acetic acid (II) and trans-4-aminomethylcyclohexanecarbonyl-D-phenylalanyl-Ψ(CH2-NH)-4-aminophenyl acetic acid (III) were synthesized. These pseudo-peptide analogs did not exhibit any detectable inhibitory activity against plasma kallikrein (PK), plasmin (PL), urokinase (UK), thrombine (TH) or trypsin (TRY). These results indicate that both carbonyl groups in the PKSI-527 are important for the manifestation of potent inhibitory activity against plasma kallikrein.View full abstractDownload PDF (645K) -
Keisuke KOJIMA, Kimio ISAKA, Purev ONDOGNII, Oyun ZEVGEEGIIN, Khishgee ...1999 Volume 47 Issue 8 Pages 1145-1147
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new prenyl-benzoylfuranone type sesquiterpenoid derivatives, 3S*-(2, 4-dihydroxybenzoyl)-4R*, 5R*-dimethyl-5-(4, 8-dimethyl-3(E), 7(E)-nonadien-1-yl)tetrahydro-2-furanone, 3S*-(2, 4-dihydroxybenzoyl)-4R*, 5R*-dimethyl-5-[4-methyl-5-(4-methyl-2-furyl)-3(E)-penten-1-yl]tetrahydro-2-furanone and 3S*-(2, 4-dihydroxybenzoyl)-4R*, 5R*-dimethyl-5-[4-methyl-5-(4-methyl-2-furyl)-3(E)-penten-1-yl]tetrahydro-2-furanone were isolated from the roots of Ferula ferulioides. The structures were established by comprehensive spectral analysis. The biosynthetic pathway leading to their prenyl-benzoylfuranone type sesquiterpenoids is proposed based on their structures.View full abstractDownload PDF (478K) -
Hideyuki ITO, Tsutomu HATANO, Osamu NAMBA, Tadashi SHIRONO, Takuo OKUD ...1999 Volume 47 Issue 8 Pages 1148-1151
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new hydrolyzable tannins, geraniinic acids B and C, and phyllanthusiin F, were isolated from the water-soluble portion of 70% aqueous acetone homogenate of the Geranium thunbergii leaves and their structures were determined by spectroscopic and chemical methods. These tannins are regarded as modified metabolites of geraniin, a major component of this plant. Phyllanthusiins, which are tannins characteristic of the Pyrllanthus species of Euphorbiaceae, were also isolated from this plant.View full abstractDownload PDF (693K) -
Yueh-Hsiung KUO, Shu-Ling LIN1999 Volume 47 Issue 8 Pages 1152-1153
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExtracts of the whole herb of Mosla dianthera were found to contain three new compounds, 4, 5-dimethoxy-2, 3-methylenedioxy-1-propenylbenzene, 4, 5-dimethoxy-2, 3-methylenedioxycinnamaldehyde, and 4, 5-dimethoxy-2, 3-methylenedioxybenzaldehyde together with eleven known compounds, fatty alcohols, 2, 4, 5-trimethoxybenzaldehyde, mixture of β-sitosterol and stigmasterol, betulinic acid, oleanolic acid, ursolic acid, arjunolic acid, β-sitosteryl glucopyranoside, palmitic acid, myo-inositol. luteolin and resmarinic acid.View full abstractDownload PDF (486K) -
Shinichi YOSHIDA, Masao YAMAMOTO, Nobutaka MOCHIZUKI, Hiroyuki NOHIRA1999 Volume 47 Issue 8 Pages 1154-1156
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new synthetic method for chiral oxazolidinone derivatives, therapeutic agents for treating urinary disturbance, is described. The condensed compound obtained from chiral 1-amino-3-phenyl-2-propanol and 1-phenyl-3-morpholino-1-propanone was reduced with Me4NBH(OAc)3 to give the intermediate, 1-(3-morpholino-1-phenylpropyl)amino-3-phenyl-2-propanol (MAPP) in 34% diastereomeric excess (d.e.). MAPP was converted to an urethane and purified by recrystallization of its methanesulfonate, toe afford a single isomer, (2R)-1-[N-[(1S)-3-morpholino-1-phenylpropyl]-N-ethoxycarbonyl]amino-3-phenyl-2-propanol methanesulfonate (4-A·methanesulfonate).View full abstractDownload PDF (555K) -
Toshihiro AKIHISA, Ryuichi HIDESHIMA, Kazuo KOIKE, Yumiko KIMURA, Tamo ...1999 Volume 47 Issue 8 Pages 1157-1160
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of a triterpene alcohol isolated from the nonsaponifiable lipids of both the root and aerial part extracts of Cimicifuga simplex (Ranunculaceae) was established to be cycloarta-16, 24-dien-3β-ol (1). Spectral identity of the 24, 25-dihydro derivative (4) of 1 with 24, 25-dihydrocimicifugenol demonstrated that cimicifugenol, previously assigned the erroneous structure of cycloarta-7, 24-dien-3β-ol, possesses structure 1.View full abstractDownload PDF (626K) -
Toshihiro AKIHISA, Yumiko KIMURA, Takaaki TAI, Koichi ARAI1999 Volume 47 Issue 8 Pages 1161-1163
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of astertarone B isolated from the root extract of Aster tataricus L. (COmpositae) was established to be 4β-hydroxy-4-epishion-21-en-3-one based on spectroscopic methods.View full abstractDownload PDF (477K) -
Hiroyuki AKITA, Katsumi KURASHIMA, Masako NOZAWA, Takako KAWANA, Kiyom ...1999 Volume 47 Issue 8 Pages 1164-1166
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe enantioselective hydrolysis of (±)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)-benzenesulfonamides 3 with lipase Amano P from Pseudomonas sp. in a water-saturated solvent gave (R)-4-(1-hydroxyethyl)-N-(cyclohyxylcarbamoyl)benzenesulfonamide 2 (39%, >99% ee) and unchanged (S)-3 (50%, 62% ee). On the other hand, enantioselective esterification of (±)-2 with lipase Amino P in the presence of vinyl acetate provided (R)-3 (41%, >99% ee) and unchanged (S)-2 (46%, 78% ee).View full abstractDownload PDF (517K) -
Ryuichiro TANAKA, Naoki NODA, Kazumoto MIYAHARA1999 Volume 47 Issue 8 Pages 1167-1169
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe lipid composition of the earthworm, Pheretima asiatica (Annelida), was analyzed. Four glycerophospholipids, together with four known glycosphingolipids, were isolated in pure form. The former four were 1-alkyl 2-acyl glycerophosphocholines possessing a C17 : 0 and/or C18 : 1 fatty acid residue. Their structures, including the position and geometry ot the double bond, were determined on the bases of chemical and psectral data.View full abstractDownload PDF (560K) -
Ikuo SAIKI, Takeshi YAMAURA, Yasuharu OHNISHI, Yoshihiro HAYAKAWA, Yas ...1999 Volume 47 Issue 8 Pages 1170-1174
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOur previous study demonstrated that the oral administration of Juzen-taiho-to resulted in a significant inhibition of the liver metastasis of colon 26-L5 cells as compared with the untreated control, without side effects. We attempted to investigate the relationship between the HPLC pattern (referred to as the fingerprint) of the formulation and its component crude drugs and the inhibition of tumor metastasis in order to obtain the optimal efficacy and constant quality of the formulation. Two Juzen-taiho-to formulations (batches #1 and #2), which were individually prepared using the same 10 crude drugs and the same preparation procedure, showed similar anti-metastatic effects and absorbance patterns by HPLC analysis. Some variant formulations of Juzen-taiho-to, in which one crude drug was substituted with other crude drugs from different sources or places of origin, exhibited reduced efficacy as compared with the original formulation, as well as differences in the fingerprint pttern compared with the original formulation. Juzen (Naimo-Ogi→Kibana-Ogi), a variant formulation with the substitution of Astragali radix of a different origin and place of harvest, showed significant inhibition of the liver metastasis of tumor cells and a HPLC fingerprint pattern similar to that of the original formulation. Thus, HPLC fingerprint analysis of Kampo medicines may provide a useful basis for obtaining their optimal efficacy as well as constant quality of the formulation, although it has some problems and limitations, such as detectability by and sensitivity to UV absorbance.View full abstractDownload PDF (852K) -
Akiko KUSANO, Makio SHIBANO, Genjiro KUSANO1999 Volume 47 Issue 8 Pages 1175-1179
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive malonyl cyclolanostanol glycosides, 23-O-acetyl-7, 8-didehydroshengmanol 3-O-(2'-O-malonyl)-β-D-xylopyranoside, 23-O-acetylshengmanol 3-O-(2'-O-malonyl)-β-D-xylopyranoside, 2'-O-malonylcimicifugoside, 24-epi-24-O-acetyl-7, 8-didehydrohydroshengmanol 3-O-(2'-O-malonyl)-β-D-xylopyranoside, and 2'-O-malonylcimiaceroside B, were isolated from the underground parts of Cimicifuga simplex WORMSK. (Ranunculaceae), together with two related cyclolanostanol glycosides, 23-O-acetyl-7, 8-didehydroshengmanol 3-O-β-D-xylopyranoside, 24-O-acetyl-25-O-methyl-7, 8-didehydrohydroshengmanol 3-O-β-D-xylopyranoside. Their structures were elucidated on the basis of spectral and chemical evidence.View full abstractDownload PDF (765K) -
Tadashi SHIRAIWA, Takashi KATAYAMA, Joji ISHIKAWA, Takeshi ASAI, Hidem ...1999 Volume 47 Issue 8 Pages 1180-1183
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCysteamine was condensed with glyoxylic acid monohydrate in a mixture of acetic acid and ethanol in the presence of (2R, 3R)- or (2S, 3S)-tartaric acid [(R)- or (S)-TA], as the resolving agent, to give the salt of (-)-2-thia-zolidinecarboxylic acid [(-)-2-THC] with (R)-TA or the salt of (+)-2-THC with (S)-TA. Treatment of these salts with triethylamine in methanol afforded (-)- and (+)-2-THC. The (-)- and (+)-2-THC obtained were betermined to be enantiopure forms by comparing their powder X-ray diffiraction patterns with that of (RS)-2-THC. The absolute configurations of (-)- and (+)-2-THC were estimated based on molar rotations of (2R, 4R)- and (2S, 4S)-2, 4-thiazolidinedicarboxylic acids, (R)-4-thiazolidinecarboxylic acid, and (-)- and (+)-2-THC. (-)-2-THC was determined to have the (R)-configuration, and (+)-2-THC to have the (S)-configuration.View full abstractDownload PDF (636K) -
Masanori INAGAKI, Ryuichi ISOBE, Tomofumi MIYAMOTO, Ryuichi HIGUCHI1999 Volume 47 Issue 8 Pages 1184-1187
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCollision-induced dissociation (CID) spectra of sodium ion complexes ([M+Na]+ ions), produced by FAB-MS of methyl ester derivatives of ganglioside, indicate the length of the fatty acyl chain of the ceramide moieties without chemical degradation. In the case of a genuine ganglioside, only the fission of the glycosyl linkage of sialic acid was prominently observed.View full abstractDownload PDF (486K) -
Satoshi SHUTO, Nobuko SHIBUYA, Shizuo YAMADA, Takashi OHKURA, Ryohei K ...1999 Volume 47 Issue 8 Pages 1188-1192
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConformationally restricted analogs of baclofen (2), i.e., 5, 6, and their enantiomers ent-5, and ent-6, the conformations of which were restricted by introducing a cyclopropane ring, were designed as potential GABAB receptor ligands. Reaction of (R)-epichlorohydrin [(R)-7] and (4-chlorophenyl)acetonitrile in the presence of NaNH-2, in benzene/tetrahydrofuran gave chiral cyclopropane derivatives 11 and 12, which were then converted into the target compounds 5 and 6, respectively. Their corresponding enantiomers, ent-5 and ent-6, were also synthesized starting from (S)-epichlorohydring [(S)-7].View full abstractDownload PDF (805K) -
Yoshio OKADA, Atsuko FUKUMIZU, Motohiro TAKAHASHI, Toshio YOKOI, Yuko ...1999 Volume 47 Issue 8 Pages 1193-1195
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclization of dipeptidyl chloromethyl ketones gave 6-(4-aminobutyl)-3-carboxyethyl-5-methyl-2(1H)-pyrazinone, 3-(4-aminobutyl)-6-carboxyethyl-5-methyl-2(1H)-pyrazinone, and 3, 6-bis(4-aminobutyl)-5-methyl-2(1H)-pyrazinone, which were inserted into the enkephalin sequence to give opioid mimetics. Thus, it was confirmed that a pyrazinone ring can be easily inserted into a peptide sequence in order to evaluate structural components required for biologically active peptides.View full abstractDownload PDF (436K) -
Munetaka KUNISHIMA, Kazuma YOSHIMURA, Daisuke NAKATA, Kazuhito HIOKI, ...1999 Volume 47 Issue 8 Pages 1196-1197
Published: August 15, 1999
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Barbier- or Grignard-type reaction of vinyl iodides with ketones or aldehydes proceeds on treatment with samarium diiodide in benzene containing hexamethylphosphoric triamide (HMPA) to afford the corresponding coupling compounds (allyl alcohols). The reaction was shown to involve vinyl samariums as an intermediate.View full abstractDownload PDF (432K)
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