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Volume 44, Issue 10
Displaying 1-39 of 39 articles from this issue
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Ahlam M. A. HELMY, Reda M. KHALIL, Mohamed A. MORSI1996 Volume 44 Issue 10 Pages 1779-1784
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe polarographic behavior of 5-phenylazo-2-thiobarbituric acid and 5 of its substituted derivatives was investigated in a buffer solution of pH (2-12). A mechanism for the reduction pathway is suggested. Based on the results of the nitro derivative, the coupling product of 2-thiobarbituric acid with diazonium salt is most probably in the azo and not the hydrazone form. The most reliable E1/2 values at different pH's were correlated to Hammett's σ constant which reflected a fair correlation.View full abstractDownload PDF (730K) -
Yutaka OZAKI, Kazuhiro IMAIZUMI, Kyouko OKAMURA, Masahiro MOROZUMI, Ay ...1996 Volume 44 Issue 10 Pages 1785-1789
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral kinds of fused cyclic compounds were obtained by tandem Michael-Claisen condensation of ethyl 2-[bis(ethylthio)methyl]benzoate and ethyl 2-[1, 3]dithiolan-2-yl-benzoate with α, β-unsaturated carbonyl compounds. Treatment of the annulated products with mercury(II)perchlorate trihydrate or N-chlorosuccinimide gave naphthoquinones, naphthalenes, and anthracenes.View full abstractDownload PDF (872K) -
Kazuko YOSHIKAWA, Nahoko OKADA, Yukiko KANN, Shigenobu ARIHARA1996 Volume 44 Issue 10 Pages 1790-1796
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of ten related oxypregnane-oligoglycosides stephanosides A (1), B (2), C (3), D (4), E (5), F(6), G (7), H (8), I (9), and J (10) from the fresh stem of Stephanotis lutchuensis var. japonica (Asclepiadaceae)were elucidated on the basis of a detailed study of their high-field 1H- and 13C-NMR spectra. All the sugars are β (1→4)-linked and the aglycones are 12, 20 bis-O-acyl or 12-O-acyl derivatives of sarcostin.View full abstractDownload PDF (963K) -
Fumiko ABE, Tatsuo YAMAUCHI1996 Volume 44 Issue 10 Pages 1797-1800
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS10-Carboxyloganin was isolated along with β-D-glucosides of cyclopentano-normonoterpenoids and dinormonoterpenoids from the frozen fresh leaves of Cerbera manghas. Their structures were characterized by means of MS and NMR spectroscopy. The correlation of drying conditions of the leaves and yields of glucosides or allosides of cyclocerberidol and epoxycerberidol was studied. The dinormonoterpenoids were similar to those obtained from Thevetia peruviana.View full abstractDownload PDF (627K) -
Masao HISATOME, Noriaki MARUYAMA, Koichi IKEDA, Tetsuo FURUTERA, Tomiy ...1996 Volume 44 Issue 10 Pages 1801-1811
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral kinds of porphyrin derivatives covalently connected with adenine, thymine, guanine, cytosine or adenine-thymine pair in a stacking mode between the porphyrin and nucleobase moiety have been synthesized via amide formation reaction of (2-aminophenyl)porphyrin derivatives with nucleobase-alkanoic acids, and characterized by spectroscopic methods. In the 1H-NMR spectra of these nucleobase-porphyrins the proton signals of the nucleobase moieties appear at remarkably higher fields than those of the reference compounds (the corresponding nucleobase-alkanoates) which have no porphyrin moiety. The behaviors of the high field shifts, due to the diamagnetic ring current effect of the porphyrin ring, reflect the characteristic conformational features of these compounds in which the base moieties are located at the upper zone of the porphyrin ring. The Soret bands of the porphyrin in the electronic absorption spectra were markedly weaker in intensity compared with those of the reference compound which has no nucleobase moiety. Both the high-field shifts of the base protons and the hypochromic effects on the Soret band are larger in guanine and cytosine systems than those in adenine and thymine systems, respectively.Those results indicate greater affinity of guanine and cytosine for porphyrin in comparison with adenine and cytosine, respectively, and this conclusion is compatible with the reported electronic spectral properties of mixtures of polynucleotides and water-soluble porphyrin derivatives.View full abstractDownload PDF (1923K) -
Yutaka AOYAGI, Mikiko MAEDA, Akira MORO, Ken KUBOTA, Yohko FUJII, Haru ...1996 Volume 44 Issue 10 Pages 1812-1818
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSamarium(II) iodide-mediated intermolecular coupling reactions of N, N-dibenzylenamides (1a-d) with carbonyl compounds (2a-i) produced the corresponding N, N-dibenzyl-γ-hydroxyamides (3a-i) in moderate to good yields.Attempts to remove the two benzyl groups of 3a using hydrogenolysis and Birch reduction were unsuccessful. On the other hand, the lithium aluminum hydride reduction of 3a produced 10 in 61% yield, and dedibenzylation using 20% Pd(OH)2 on carbon gave the corresponding δ-aminoalcohol (11).View full abstractDownload PDF (939K) -
Haruaki ISHIYAMA, Masami ISHIBASHI, Jun'ichi KOBAYASHI1996 Volume 44 Issue 10 Pages 1819-1822
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA diastereomer of the C-1-C-9 fragment of amphidinolide C, a potent cytotoxic 25-membered macrolide isolated from a marine dinoflagellate, Amphidinium sp., has been synthesized to provide an authentic sample for use in studies on the degradation of amphidinolide C.View full abstractDownload PDF (825K) -
Katsuo SHINOZAKI, Kazuhiro MIZUNO, Hideaki WAKAMATSU, Yukio MASAKI1996 Volume 44 Issue 10 Pages 1823-1830
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSManipulation of cis (4S, 5S)-4, 5-disubstituted 2-oxazolidinones (4, 5), derived easily from D-glucosamine (1) as a chiral pool, including degradation of the C6-carbon and/or one-carbon homologation at the C1-position allowed chiral syntheses of (2S, 3S)-dihydroxy-(4S)-amino acid moieties (6-8), which are important structural components of a gastroprotective substance, AI-77-B, and a group of antitumor substances, calyculins.View full abstractDownload PDF (1187K) -
Ikuo KAWASAKI, Masayuki YAMASHITA, Shunsaku OHTA1996 Volume 44 Issue 10 Pages 1831-1839
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNortopsentins A-D, antifungal 1, 4-bisindolylimidazole marine alkaloids isolated from a sponge, were synthesized through palladium-catalyzed cross-coupling of 3-indolylboronic and 6-bromo-3-indolylboronic acids with halogenoimidazoles as the key reaction.View full abstractDownload PDF (1440K) -
Motomasa KOBAYASHI, Yin-Ju CHEN, Kouichi HIGUCHI, Shunji AOKI, Isao KI ...1996 Volume 44 Issue 10 Pages 1840-1842
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAragusteroketals A (1) and C (2), two new marine steroids having dimethylketal structure, were isolated from an Okinawan marine sponge of Xestospongia sp. The chemical structures of 1 and 2 were determined on the basis of spectroscopic analysis and chemical evidence. Compounds 1 and 2 showed potent cytotoxic activity with the same IC50 value of 4 ng/ml against KB cells.View full abstractDownload PDF (481K) -
Haruhiro FUJIMOTO, Etsuko NEGISHI, Kentaro YAMAGUCHI, Nahoko NISHI, Mi ...1996 Volume 44 Issue 10 Pages 1843-1848
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new meroterpenoid named setosusin and two new tryptoquivalines were isolated as tremorgenic principles from an Ascomycete, Corynascus setosus, together with four known metabolited, fiscalin B, helvolic acid, helvolinic acid, and 2-(1-oxo-2-hydroxyethyl)furan. The structure of setosusin was determined from the chemical and spectral data and by X-ray crystallographic analysis of its deacetyl-dehydrated derivative. The two new tryptoquivalines were deduced to be 27-epi-isomers of tryptoquivaline and nortryptoquivaline from their spectral data supported by X-ray analysis.View full abstractDownload PDF (860K) -
Masayuki TANNO, Shoko SUEYOSHI, Naoki MIYATA, Shigeo NAKAGAWA1996 Volume 44 Issue 10 Pages 1849-1852
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGeneration of nitric oxide (NO) from aromatic N-nitrosoureas 1-3 at ambient temperature without photo irradiation was confirmed by the trapping of NO as a nitrosyl complex of 5, 10, 15, 20-tetrahenylporphyrinatocobalt(II) and spectrophotometrically quantified by means of the Griess reaction using a newly designed test apparatus in which NO-2 is generated from NO. 3, 3-Dibenzyl-1-(4-tolyl)-1-nitrosourea (1a) showed the greatest NO-generation ability among compounds 1-3 and N-acetyl-S-nitroso-DL-penicillamine (SNAP) in chloroform. A comparison of 1a and usual NO donors (NOC-18, NOR-4, SIN-1, SNAP, and SNP) in Krebs buffer was also made using the same test apparatus.View full abstractDownload PDF (662K) -
Shigeharu NOCHI, Takatoshi KAWAI, Yoshiyuki KAWAKAMI, Naoki ASAKAWA, N ...1996 Volume 44 Issue 10 Pages 1853-1857
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe optical isomers of sodium 2-[[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methylsulfinly]-1H-benzimidazole (E3810), a proton pump inhibitor, were separated by HPLC and their absolute configurations were determined by X-ray crystallographic analysis.View full abstractDownload PDF (696K) -
Kazuhiko TAKE, Kazuo OKUMURA, Kazunori TSUBAKI, Kiyoshi TANIGUCHI, Tak ...1996 Volume 44 Issue 10 Pages 1858-1864
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-tert-Butyl-4, 4-diphenyl-2-cyclopentenylamine ((±)-3) was designed to restrict the conformation of terodiline 1 and was synthesized in a 6-step approach starting with diphenylacetaldehyde (10) or in a 4-step approach starting with 2, 2-diphenyl-4-pentenoic acid (17). Using di-p-toluoyltartaric acid as a resolving agent, the synthetic (±)-3 was resolved into its optically pure forms, (-)- and (+)-3. The (-)-enantiomer (-)-3·HCl (FK584) showed about ten times more potent inhibitory acitivity on urinary bladder rhythmic contraction in rats (ED30 =0.18 mg/kg, i.v.)than terodiline (ED30=1.9 mg/kg, i.v), while the (+)-enantiomer (+)-3·HCl showed no inhibitory activity at 1.0 mg/kg i.v.Compound (-)-3·HCl (FK584) has pharmacological properties similar to those of terodiline, as evaluated by in vitro assay and is currently in clinical development for the treatment of overactive detrusor.View full abstractDownload PDF (1019K) -
Hideki ANAN, Akihiro TANAKA, Ryuji TSUZUKI, Masaki YOKOTA, Takeyuki YA ...1996 Volume 44 Issue 10 Pages 1865-1870
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 4-(3, 4-dihydroxyphenyl)-1, 2, 3, 4-tetrahydroisoquinoline derivatives showed potent DA1 agonistic activities. We investigated the structure-activity relationship of the racemic compounds of this series. 4-(3, 4-Dihydroxyphenyl)-7-methanesulfonamido-1, 2, 3, 4-tetrahydroisoquinoline (43) was identified as a potent renal vasodilator with activity almost equal to that of YM435 (1).View full abstractDownload PDF (944K) -
Minoru OKADA, Toru YODEN, Eiji KAWAMINAMI, Yoshiaki SHIMADA, Masafumi ...1996 Volume 44 Issue 10 Pages 1871-1879
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious 4-N-substituted amino-4H-1, 2, 4-triazole derivatives were synthesized and evaluated for aromatase-inhibitory activity (in vitro) and for pregnant mare serum gonadotropin (PMSG)-induced estrogen synthesis-inhibitory activity (in vivo). The 4-(4-cyanophenyl) amino derivative and 4-(4-nitrophenyl)amino derivative, each possessing a strong electron-withdrawing group on the phenyl moiety, showed potent aromatase-inhibitory activity. Structure-activity relationship studies indicated that 4-[(4-bromobenzyl)(4-cyanophenyl)amino]-4H-1, 2, 4-triazole (5k, YM511) is a highly potent aromatase inhibitor with IC50 values of 0.4 and 0.12 nM in in vitro experiments using rat ovary and human placenta, respectively, and an in vivo ED50of 0.002 mg/kg in rats on oral administration.YM511 was also a weak inhibitor of other steroid hormone synthesis enzymes. These data suggest that YM511 is a highly selective aromatase inhibitor and may be a useful agent for the treatment of estrogen-dependent diseases such as breast cancer.View full abstractDownload PDF (1078K) -
Katsuro KUROSAWA, Naoki SAKURA, Tadashi HASHIMOTO1996 Volume 44 Issue 10 Pages 1880-1884
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDog neuromedin U-8 (d-NMU-8; pGlu-X2-Leu-Y4-Arg-Pro-Arg-Pro-Arg-Asn-NH2, X=Y=Phe) has potent biological activity to stimulate an isolated chicken crop smooth muscle preparation with the relative activity (RA value) of 5.78 to porcine neuromedin U-8 (p-NMU-8). To elucidate the contribution of the two phenylalanine residues of NMU-8 to the biological activity, fourteen d-NMU-8 analogs modified either at positio 2 or 4, [X2]- or [Y4]-d-NMU-8, were synthesized, where X and Y were Ala, Tyr, Trp, Thr, Glu, His or cyclohexylalanine (Cha).Most of the analogs retained very low contractile activity, suggesting the importance of both Phe residues in d-NMU-8 for the biological activity. [X2]-d-NMU-8 analogs had lower biological activity in terms of the RA value than the corresponding [Y4]-d-NMU-8, when X and Y are the same amino acid. Loss of aromaticity of Phe2([Cha2]-d-NMU-8) resulted in a marked decrease of the contractile activity, while that of Phe4 ([Cha4]-d-NMU-8)resulted in retention of considerable activity, with the RA value of 2.68. [Tyr4]-d-NMU-8 was an exceptional analog with higher contractile activity (p<0.01) than the parent compound d-NMU-8, having the RA value of 12.6. The results indicated that the aromatic side chain of the Phe residue at position 2 contribues more than that at position 4 to the biological activity.View full abstractDownload PDF (747K) -
Shinji FUNAYAMA, Kiyoshi MURATA, Shigeo NOZOE1996 Volume 44 Issue 10 Pages 1885-1889
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absolute stereochemistry of the C-2' position of (-)-preorixine, postulated to be an important biosynthetic precursor of various quinoline alkaloids, was assigned as R by the combination of its chemical transformation and the extended Mosher method. The stereochemistry of the C-2' position of (+)-orixine was also concluded to be R, establishing taht no inversion occurred when (-)-preorixine was transformed into (+)-orixine.View full abstractDownload PDF (767K) -
Masayuki YOSHIKAWA, Hiromi SHIMADA, Nobuhiro YAGI, Nobutoshi MURAKAMI, ...1996 Volume 44 Issue 10 Pages 1890-1898
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLactonization reaction of 2-carboxystilbene mediated by copper(II) chloride proceeded regiospecifically to give the five-membered lactone, while the bromolactonizations using N-bromosuccinimide and anodic oxidation were found to furnish the six-membered lactone. Using these regiospecific lactonization reactions as a key step, antiallergic and antimicrobial isocoumarins and the benzylidenephthalides thunberginols A and F and their 3'-deoxyanalogs were synthesized from phyllodulcin and hydrangenol.Two phthalides called hydramacrophyllols A and B were isolated from Hydrangeae Dulcis Folium and their stereostructures were determined on the basis of physicochemical and chemical evidence, which included the syntheses of hydramacrophyllols A and B from hydrangenol by the application of the lactonization method using copper(II)chloride. In addition, hydramacrophyllols A and B were found to exhibit an inhibitory effect on the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.View full abstractDownload PDF (1362K) -
Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Satoshi YOSHIZUMI, Nobutoshi M ...1996 Volume 44 Issue 10 Pages 1899-1907
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcylated polyhydroxyolean-12-ene triterpene oligoglycosides, camelliasaponins A1, A2, B1, B2, C1, and C2, were isolated from the seeds of Camellia japonica L. The structures of six camelliasaponins were elucidated on the basis of chemical and physicochemical evidence. Camelliasaponins B1, B2, C1, and C2 were found to exhibit inhibitory activity on ethanol absorption. By comparison of the inhibitory activities for camelliasaponins with those for desacyl-camelliasaponins, acyl groups such as the angeloyl or tigloyl group were found to be essential to exerting the activity.View full abstractDownload PDF (1287K) -
Tomonori NAKAMURA, Emi OKUYAMA, Mikio YAMAZAKI1996 Volume 44 Issue 10 Pages 1908-1914
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new neurotropic sesquiterpenoids, veranisatins A, B and C, were isolated from star anise (Illicium verum HOOK. fil., Illiciaceae). Veranisatins showed convulsion and lethal toxicity in mice at a dose of 3 mg/kg (p.o.), and at lower doses they caused hypothermia. Veranisatin A and the related compound, anisatin, were tested for the other pharmacological activities such as locomotor activity and analgesic effect. Both compounds decreased the locomotion enhanced by methamphetamine at oral doses of 0.1 and 0.03 mg/kg, respectively, and demonstrated the analgesia on acetic acid-induced writhing and tail pressure pain at almost similar doses.View full abstractDownload PDF (901K) -
Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Emiko HARADA, Nobutoshi MURAKA ...1996 Volume 44 Issue 10 Pages 1915-1922
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPotent inhibitors of ethanol absorption, elatosides A and B, were isolated from the bark of Aralia elata SEEM. through bioassay-guided separation together with elatosides C and D and four known oleanolic acid glucuronide-saponins, spinasaponin A, spinasaponin A 28-O-glucoside, and stipuleanosides R1 and R2. The structures of elatosides A, B, C, and D were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-{[β-D-xylopyranosyl (1→2)][β-D-galactopyranosyl (1→3)]}-β-D-glucopyranosiduronic acid, oleanolic acid 3-O-{[β-D-galactopyranosyl (1→2)] [β-D-galactopyranosyl (1→3)]}-β-D-glucopyranosiduronic acid, and their 28-O-glucopyranosyl esters, respectively.The inhibitory effect of various oleanolic acid 3, 28-O-bisdesmosides, oleanolic acid 3-O-monodesmosides, and oleanolic acid on ethanol absorption was examined and it was found that the 3-O-glucuronide moiety and the 28-carboxyl group in oleanolic acid glucuronide-saponin were required to exert the inhibitory activity.View full abstractDownload PDF (1047K) -
Masayuki YOSHIKAWA, Toshiyuki MURAKAMI, Emiko HARADA, Nobutoshi MURAKA ...1996 Volume 44 Issue 10 Pages 1923-1927
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hypoglycemic component, elatoside E, was isolated from the root cortex of Aralia elata SEEM. (Araliaceae) together with elatoside F and eight known oleanolic acid glycosides, elatosides A and C, oleanolic acid 3-O-[α-L-arabinofuranosyl (1→4)]-β-D-glucopyranosiduronic acid, oleanolic acid 3-O-β-D-glucopyranosiduronic acid, stipuleanosides R1 and R2, and chikusetsusaponins IV and IVa. The structures of elatosides E and F were determined on the basis of chemical and physicochemical evidence as oleanolic acid 3-O-[β-D-xylopyranosyl(1→2)][β-D-glucopyranosyl (1→3)]-α-L-arabinopyranoside and its 28-O-β-D-glucopyranosyl ester, respectively.The hypoglycemic activity of oleanolic acid and nine oleanolic acid oligoglycosides from the root cortex of Aralia elata was determined by monitoring inhibition effect on the elevation of plasma glucose level by oral sucrose tolerance test in rats, and some structure-activity relationships of oleanolic acid glycoside were obtained.View full abstractDownload PDF (779K) -
Naoto OKU, Junko TSUDERA, Kohta KUROHANE, Shoji OKADA1996 Volume 44 Issue 10 Pages 1928-1930
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of freeze-thawing of egg phosphatidylcholine (PC) and octyl glucoside (OG) on vesicle growth and on liposomal formation by the subsequent removal of the OG was investigated. When increasing concentrations of OG were mixed with PC vesicles of 10 or 20 mM PC, vesicle growht was observed until the ratio of OG/PC reached about 3.0, and then micellization occurred at a higher concentration of OG, as determined by turbidity change and microscopic observation. On the other hand, a marked increase in turbidity was observed after freeze-thawing of the samples when the OG/PC retio was less than 3.0. The frozen and thawed mixed bilayer composed of OG/PC=2 formed closed vesicles having solute-trapping ability as determined by fluorescence microscopy. Interstingly, the trapping volume of liposomes generated after removal of OG from freeze-thawed samples was higher for those from mixed micelles than for those from mixed vesicles composed of OG and PC. When increasing concentrations of OG were mixed with PC vesicles of 0.8 or 2 mM PC, micellization started when the OG was at about its critical micelle concentration (cmc), although marked turbidity was observed when the OG/PC ratio was 2.0 after freeze-thawing. These data suggest that freeze-thawing affects the bilayer-micelle transition and liposomal formation after removal of OG even at concentrations of detergent lower than its cmc.View full abstractDownload PDF (740K) -
Yasushi MATSUNAGA, Nobuyuki BANDO, Hiroshi YUASA, Yoshio KANAYA1996 Volume 44 Issue 10 Pages 1931-1934
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of grinding and tableting on the physicochemical stability of TAT-59, (E)-4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-(4-isopropyl)phenyl]-1-butenyl]phenyl monophosphate, were studied. The crystallinity of TAT-59 ground in a planetary ball mill for 0-120 min or compressed at 0-4500 kg/cm2 was evaluated by X-ray diffraction analysis and differential scanning calorimetry (DSC). The surface of TAT-59 was measured under a scanning electron microscope (SEM). The physicochemical stability of TAT-59, ground or compressed, was determined by measurements of water content, crystallinity and the amount of hydrolysis product, DP-TAT-59, formed. The crystallinity of ground TAT-59 decreased with increasing grinding time, and the amount of DP-TAT-59 increased with decrease in the crystallinity. Similar to ground TAT-59, the crystallinity of TAT-59 tablet gradually decreased with increasing compression pressure, and the amount of DP-TAT-59 tended to increase with decreasing crystallinity. These findings suggested that the dacrease of the crystallinity of TAT-59 by mechanical force, such as grinding and tableting raised the drug's reactivity and affected its stability.View full abstractDownload PDF (974K) -
Ya Min WANG, Hitoshi SATO, Isao ADACHI, Isamu HORIKOSHI1996 Volume 44 Issue 10 Pages 1935-1940
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis study describes the preparation and characterization of poly(lactic-co-glycolic acid) microspheres containing a novel anticancer agent, taxol (namely, Taxol-PLGA-MS). A solvent evaporation technique was utilized to prepare Taxol-PLGA-MS. The trapping efficiency of taxol in the microspheres was greater than 90% and reproducible.The in vitro release rate of taxol from the microspheres was very low, and less than 15% of the initial amount of taxol was released in three weeks, irrespective of the drug loading level. When a chemical additive, isopropyl myristate(IPM), was introduced at the level of 30% (w/w), the release of taxol increased significantly; approximately 70% of the initial amount of taxol was released at a nearly constant rate for three weeks. Elevation of the loaded IPM level to 50% (w/w) produced a more rapid release of the drug. Scanning electron microscopy showed that Taxol-PLGA-MS were spherical with a smooth surface. More than half (55-65%) of the microspheres had a diameter of 20-45μm. Incorporation of IPM had no significant influence on the particle size, surface morphology, or degradation behavior of the microspheres. It was strongly suggested that the release of taxol from the microspheres was dominated mainly by the drug diffusion in the matrix. As evaluated from the particle size, drug content, and in vitro release property, IPM-containing Taxol-PLGA-MS may be suitable for chemoembolization therapy of cancer diseases.View full abstractDownload PDF (1419K) -
Isamu TAKAGI, Hidekazu SHIMIZU, Toshihisa YOTSUYANAGI1996 Volume 44 Issue 10 Pages 1941-1947
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo explore the feasibility of alginate gel as a vehicle for liposomes, we investigated the effects of various factors associated with the loading of drug-containing liposomes into the gel beads. The loading process includes (1) mixing of liposomes and alginate solution, (2) calcium induced gelation of alginates, (3) the time-dependent contraction of a gel body squeezing out interior water, and (4) possible leakage or release of a drug entrapped in liposomes in a series of each of theses processes. These effects were examined in terms of the leakage of a marker 5(6)-carboxyfluorescein (CF) from liposomes of egg phosphatidylcholine (EPC) and EPC/cholesterol (EPC/Cho)and liposome (phosphorus) release from curing and fully-cured gel beads whose initial polymer concentrations were 4 and 2%. Major findings were : (1) Alginate induced the leakage of a water-soluble drug incorporated in the liposomes as a function of the polymer concentration and the mixing time. (2) Calcium ions also stimulated the leakage of the drug. EPC/Cho liposomes were several times more resistant to the leakage of CF than were EPC liposomes. (3) The liposomes were well loaded without any loss in the gel bead despite the squeezing outflow of water and the bead contraction during gel curing. (4) Such curing caused leakage of the drug from the EPC liposomes in the very early stage while no effect was observed in the EPC/Cho liposomes. (5) In the gel-eroding medium (pH 7.4 Tris-HCl, 37°C), the total drug release was controlled by the erosion rate of the bead body. Immediately after the bead erosion, EPC liposomes retained about 60% of the drug in the 2% bead and only about 20% in the 4% bead, whereas EPC/Cho liposomes retained more than 85% regardless of the initial alginate concentration. The results provide valuable information for the design and applicability of the gel-loaded liposome delivery system.View full abstractDownload PDF (1017K) -
Sumie YOSHIOKA, Yukio ASO, Shigeo KOJIMA, Alain LI WAN PO1996 Volume 44 Issue 10 Pages 1948-1950
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present study investigates the effect of batch-variation on the evaluation of stability data obtained from three batches of pharmaceutical products. Using stability data generated by the Monte Carlo method, the power of analysis of variance for assessing batch-variation was determined as functions of significance level and assay error.The results obtained from degradation data simulated for a product exhibiting zero-order degradation of 0.2%/month indicate that a significance level of approximately 0.25 is necessary in order to obtain a minimum detectable difference of 25% if the beta error is fixed at 20%. Assay methods with smaller margins of error are recommended, as is repeating the assay in order to reduce assay error down to approximately 0.5% standard deviation. In addition, the validity of the 0.25 significanece level, which is recommended in the ICH (International Conference on Harmonisation of Technical Requirements for the Registration of Pharmaceuticals for Human Use) Tripartite guideline, is discussed.View full abstractDownload PDF (483K) -
Ping XIAO, Jiashi LI, Hajime KUBO, Kazuki SAITO, Isamu MURAKOSHI, Shig ...1996 Volume 44 Issue 10 Pages 1951-1953
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new lupine alkaloid, (-)-14β-hydroxymatrine (1) was isolaed from the dry roots of Sophora tonkinensis together with 11 known lupine alkaloids. The absolute structure (5S, 6S, 7R, 11R, 14S) of the new base was confirmed by comparison of the natural product with a synthetic sample derived from (+)-matrine.View full abstractDownload PDF (576K) -
Mitsuhiro YOSHIMATSU, Takayo FUSEYA1996 Volume 44 Issue 10 Pages 1954-1957
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTrimethylsilyl (TMS)-substituted enynes 9-11, 13-17 and (Z)-enediynes 18 were prepared by dehydration of the TMS-substituted propargyl alcohols 1-8 with polyphosphoric acid trimethylsilyl ester.View full abstractDownload PDF (598K) -
Kiyoshi IKEDA, Keisuke MIYAJIMA, Kazuo ACHIWA1996 Volume 44 Issue 10 Pages 1958-1961
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new glycolipids, which mimic lipid A disaccharide, were synthesized from N, N'-diacylchitobiose via a key intermediate (2). They showed mitogenicity and nitric oxide (NO) productivity.View full abstractDownload PDF (630K) -
Hideaki TSUNEMATSU, Ryuichi ISOBE, Yoshihito FUTATSUKA, Magobei YAMAMO ...1996 Volume 44 Issue 10 Pages 1962-1965
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFragmentations of N-benzyloxycarbonyl-protected tetrapeptide ethyl esters containing L-proline and L-alanine in the gas phase were examined by the collisional-activated decomposition of the deprotonated molecule and the fragment ions produced by the cleavage of the tetrapeptide derivatives, in which changes in both the number and positions of the prolyl residues were observed, in negative-ion FAB-MS. The cleavage patterns of these ions in the collisional-activated decomposition mass spectra were observed to depend on the number and positions of prolyl residues in the peptide derivatives. These results indicate that the conformational difference in the tetrapeptide derivatives due to the existence of L-proline may be an important factor responsible for the fragmentations of peptide molecules in the gas phase.View full abstractDownload PDF (670K) -
Hiroaki KOMATSU, Aya KITAJIMA, Yasushi NAKATA, Satoshi OKADA1996 Volume 44 Issue 10 Pages 1966-1969
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe average diameter and size distribution of particles in commercially available isophane-insulin and zincinsulin aqueous suspensions (11 products) were examined using laser-light diffraction spectroscopy (LLDS). Wide variation was observed between products in volume-weighted and number-weighted average diameters. The particles in the insulin aqueous suspensions were found to be mono-dispersed within relatively narrow size distributions.Sonication for a short time led to a downshift in the apparent average diameter, which was most remarkable with isophane-insulin aqueous suspensions. This could be ascribed to dispersion of aggregated needle-like crystals and/or crystal breakage. In the case of biphasic isophane-insulin aqueous suspensions, the average size as well as the size distribution shifted toward the smaller end of the scale with decrease in the isophane content.View full abstractDownload PDF (660K) -
Tomonori ARAO, Tomoko IDZU, Junei KINJO, Toshihiro NOHARA, Ryuichi ISO ...1996 Volume 44 Issue 10 Pages 1970-1972
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the root of Pueraria thomsonii (Leguminosae), three new oleanane-type triterpene glycosides, named kudzusaponin B1, acetyl-kaikasaponin III and acetyl-soyasaponin I were isolated, together with soyasaponin I (4)and subproside V (5). Their structures were determined to be 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol B (1), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl sophoradiol 22-O-acetate (2) and 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol B 22-O-acetate (3), respectively.View full abstractDownload PDF (581K) -
Hideo UEDA, Masahiko OGIHARA, Kenji SUGIBAYASHI, Yasunori MORIMOTO1996 Volume 44 Issue 10 Pages 1973-1976
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of ultrasound (150kHz, 111mW/cm2) on the permeability of isosorbide dinitrate (ISDN) and antipyrine (ANP) through excised hairless rat skin was evaluated using an Arrhenius plot. The permeability coefficients of ISDN across skin (at various temperatures) in the presence and absence of ultrasound were virtually isolinear on the Arrhenius plot, It has been suggested that the temporal increase in the ISDN flux, which was observed when ultrasound was applied in our previous study, was only a result of the thermal effect of ultrasound, i.e. an increase in the temperature of the donor solution. On the other hand, ultrasound influenced the Arrhenius plot of ANP, suggesting that the enhancement effect for ANP permeation could be not explained only by the thermal effect of ultrasound. In addition, the effective diffusion (D) and partitio coefficients (K) of ISDN and ANP were estimated using their skin permeation profiles across the ultrasonic pretreated skin. The coefficients of ISDN with ultrasonic pretreatment were comparable to those without pretreatment. On the other hand, the D value of ANP with ultrasonic pretreatment was increased about 4 times by ultrasonic pretreatment, in spite of an insignificant change in the K value. These results suggest that the ultrasound used in the present study increased the effective diffusivity across the aqueous region in the stratum corneum to enhance the skin permeation of the polar compound, ANP.View full abstractDownload PDF (651K) -
Tadatoshi YAMAGUCHI, Masashi ETO, Kenji WATANABE, Nobuhiro KASHIGE, Ka ...1996 Volume 44 Issue 10 Pages 1977-1979
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCondensation of 1, 2-diamines with 1, 2-diketones yielded unexpected tricyclic heterocycles. The structures were determined by single-crystal X-ray analysis.View full abstractDownload PDF (437K) -
Hiroyuki MIYACHI, Akihiko AZUMA, Erika HIOKI, Yoshiro KOBAYASHI, Shige ...1996 Volume 44 Issue 10 Pages 1980-1982
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel potent regulators of tumor necrosis factor alpha (TNF-α) production by a human promyelocytic leukemia cell line, HL-60, were prepared. All the compounds showed inducer-specific and bidirectional regulation of TNF-α production, i.e., they enhanced 12-O-tetradecanoylphorbol-13-acetate-induced TNF-α production, while they inhibited okadaic acid-induced one.View full abstractDownload PDF (443K) -
Ryuuta FUKUTOMI, Hiroyuki KAGECHIKA, Yuichi HASHIMOTO, Koichi SHUDO1996 Volume 44 Issue 10 Pages 1983-1985
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeveral aromatic urea derivatives were designed and synthesized as DNA-targeting agents. N, N'-Dimethyl-N, N'-bis[(4-amidylphenyl)amino-carbonyl]-2, 6-diaminopyridine (1) and 1, 3-bis[5-(glycylamino)pyrid-2-yl]urea (3) showed remarkable DNA-binding abilities as determined by ultrafiltration assay using calf thymus DNA, their potencies being equal to and half that of netropsin, respectively. Compound 1 inhibited the proliferation of both L1210 cells and KB cells with similar IC50 values to netropsin.View full abstractDownload PDF (479K) -
Takashi HARAYAMA, Yoshitaka NISHITA1996 Volume 44 Issue 10 Pages 1986-1988
Published: October 15, 1996
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAngular furanocoumarins (1) were synthesized via sequential reactions of vinylation of halo-hydroxycoumarins (5 or 6) with chlorodimethylvinylsilane (8)and Pd catalyst, oxidation of Tl(NO3)3 in methanol, and treatment with acid.View full abstractDownload PDF (480K)
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