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Volume 43, Issue 7
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Toshiyuki TAKAGI, Atsushi TAKESUE, Akiharu ISOWAKI, Mayumi KOYAMA, Aki ...1995 Volume 43 Issue 7 Pages 1071-1075
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn an abnormal Grignard reaction of halothane, the primary Grignard reagent reacts with another mole of halothane to give 1-bromo-1-chloro-2, 2, 2-trifluoroethylmagnesium bromide, which in turn reacts with a carbonyl compound to give 1-bromo-1-chloro-2, 2, 2-trifluoroethyl carbinols and their dehalogenation products, 1-chloro-2, 2-difluoroethenyl carbinols. We examined the application of this method to aldehydes and to unsaturated ketones. Aldehydes were much less reactive than ketones, and needed higher reaction temperature. However, elevation of temperature caused dehalogenation of the primary products to 1-chloro-2, 2-difluoroethenyl derivatives. These derivatives were treated with hydrogen fluoride to afford 1-chloro-1-(trifluoromethyl)ethene derivatives. The reaction of α, β-unsaturated ketones mainly gave 1, 2-addition products of the Grignard reagent, while 3-methyl-2-cyclohexenone gave mainly the 1, 4-adducts.View full abstractDownload PDF (823K) -
Hatsuo MAEDA, Takashi KOIDE, Toshihide MAKI, Hidenobu OHMORI1995 Volume 43 Issue 7 Pages 1076-1080
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe formation of an alkoxy triphenylphosphonium ion by anodic oxidation of Ph3 P in the presence of an alcohol was reinvestigated. When a CH2CL2 solution of Ph3P, Ph3P+H·ClO-4, and an alcohol was subjected to constantcurrent electrolysis in an undivided cell equipped with a graphite anode and a Pt cathode, the 31P-NMR spectra of the resulting electrolyte showed that alkoxy triphenylphosphonium perchlorates (2) were formed in good to fair yields from primary and secondary aliphatic alcohols, while allylic and benzylic alcohols were transformed to the correspinding alkyl phosphonium ions, and in the case of tertiary aliphatic alcohols, no formation of the corresponding alkoxy or alkyl phosphonium ions was recognized at all. The isolation of 2 thus formed was achieved in good yields by a simple procedure. For the electrolysis, Ph3P+H·BF-4 could be utilized insted of the perchlorate salt, giving an alkoxy triphenylphosphonium tetrafluoroborate (3) from primary and secondary aliphatic alcohols. The reaction of the alkoxy phosphonium ions prepared from β- and α-cholestanol with various nucleophiles such as Bu4N+·X- (X=Br, Cl, F, N3, SCN), PhSH, and PhOH was examined. The results indicated that the reaction site of the phosphonium ions is dictated by the identity of the nucleophile. A soft nucleophile was apt to attack at the α-carbon, giving the corresponding SN2 reaction product in a good yield, while a hard one tended to react at the phosphorus of the phosphonium ion, leading to the regeneration of the cholestanol.View full abstractDownload PDF (866K) -
Tatsuo NAGASAKA, Tomoko IMAI1995 Volume 43 Issue 7 Pages 1081-1088
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe following chiral pyrrolidine derivatives, 7-substituted (2R, 5S)-2-aryl-1-aza-3-oxabicyclo[3.3.0]octan-8-ones(18-24), 7-substituted (2R, 5S)-2-aryl-1-aza-3-oxabicyclo[3.3.0]oct-6-en-8-ones (25-29) and 3-substituted (S)-5-(hydroxymethyl)-2-pyrrolidinones (30-34), were synthesized starting from (S)-pyroglutamic acid and their absolute configurations were determined based on their 1H-NMR spectra.View full abstractDownload PDF (1443K) -
Takushi KURIHARA, Yasuhiko SAKAMOTO, Masato TAKAI, Hirofumi OHISHI, Sh ...1995 Volume 43 Issue 7 Pages 1089-1095
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidation of methyl (1, 2-cis)-2-phenyl-1, 2, 4, 5, 10, 10b-hexahydroazeto[1', 2' : 1, 2]pyrido[3, 4-b]indole-1-carboxylate (8a) with m-chloroperbenzoic acid (MCPBA) (3 eq) in methylene dichloride at room temperature unexpectedly gave 4, 10-dioxooctahydroisoxazolo[3, 2-c][1, 4]benzdiazonine (10) (44%), together with the two [1, 2]-Meisenheimer rearrangement products [11 (5%) and 12 (14%)]. The structure of 10 was unambiguously established by an X-ray analysis. On the other hand, the peracid oxidation of the corresponding 1, 2-trans isomer (17) gave hexahydroisoxazolo[2', 3' : 1, 2]pyrido[3, 4-b]indole (18) (37%) via the [1, 2]-Meisenheimer rearrangement of the N-oxide as well as dihydro-β-carboline N-oxide (19) (60%) and methyl cinnamate (20) (61%). The remarkable difference in the results of peracid oxidation between the two isomers (8a and 17) was rationalized on the basis of the molecular energy calculations using a combination of molecular mechanics (MM) and molecular orbitals (MO) methods.View full abstractDownload PDF (1005K) -
Isao KITAGAWA, Youichi FUKUDA, Toshio TANIYAMA, Masayuki YOSHIKAWA1995 Volume 43 Issue 7 Pages 1096-1100
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA full account of the structure elucidation of an iridoid lactone, rehmaglutin C, and a chlorinated tricyclic iridoid glucoside, glutinoside, is presented. Rehmaglutin C (10) and glutinoside (11) were isolated from Chinese Rehmanniae Radix, the dried root of Rehmannia glutinosa LIBOSCH. from China, called Kan-jio in Japanese. The absolute stereostructures 10 and 11 have been determined on the basis of chemical and physicochemical evidence which included application of the exciton chirality method for the allylic benzoyl derivative.View full abstractDownload PDF (881K) -
Takashi YOSHIDA, Kumiko HABA, Rie ARATA, Fumihisa NAKATA, Tetsuro SHIN ...1995 Volume 43 Issue 7 Pages 1101-1106
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new hydrolyzable tannins, nobotanins J and K, were isolated by a combination of column chromatography and centrifugal partition chromatography from the leaf extract of Heterocentron roseum, and shown to have trimeric and tetrameric structures composed of combinations of the common monomeric units, casuarictin and pterocarinin C, on the basis of spectral and chemical evidence.View full abstractDownload PDF (886K) -
Masaaki OMOTE, Akira ANDO, Toshiyuki TAKAGI, Mayumi KOYAMA, Itsumaro K ...1995 Volume 43 Issue 7 Pages 1107-1110
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe previously synthesized 3- and 8-mono, and 3, 8-bis(2, 2, 2-trifluoro-1-hydroxyethyl)deuteroporphyrin dimethyl esters (2-4) by Friedel-Crafts reaction of deuteroporphyrin dimethyl ester (1) with trifluoroacetaldehyde, and trifluorohematoporphyrin analogs (5 and 6) by acetylation of 2 and 3 followed by reduction. These fluorine analogs of natural porphyrins have interesting biological properties; some of them accumulate selectively in certain tumor cells. In order to introduce larger substituents at the 8- or 3-position of 2 and 3, 2 and 3 were converted in several steps to 8- and 3-formyl derivatives (13 and 14), respectively. These were treated with vinylmagnesium bromide to give 8- or 3-(1-hydroxy-2-propenyl) derivatives (15 or 16). Further, reaction of 7 or 8 with the enol ether of 2-octanone gave the 8- or 3-(3-oxo-1-nonenyl) compounds (17 or 18). The affinities of the porphyrin derivatives, obtained by hydrolysis of the above porphyrin esters, for tumor tissues were examined. Among them, the porphyrin obtained by hydrolysis of 16 was found to accumulate in liver cancer transplanted in nude mice to a greater extent than hematoporphyrin.View full abstractDownload PDF (571K) -
Isao UMEZAWA, Masako NOZAWA, Shinji NAGUMO, Hiroyuki AKITA1995 Volume 43 Issue 7 Pages 1111-1118
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree kinds of oudemansin X, (-)-1, (+)-1 and (±)-1, were totally synthesized. The key point in the present chiral synthesis was the enantioselective acetylation of the racemic alcohols, (±)-5 and (±)-8, using lipase in an organic solvent. The synthetic (-)-1 was found to exhibit strong antifungal activity against several molds and yeasts.View full abstractDownload PDF (1248K) -
Yasuo NAGAOKA, Akira IIDA, Eiichi TACHIKAWA, Tetsuro FUJITA1995 Volume 43 Issue 7 Pages 1119-1124
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe secondary structures of an ion-channel-forming icosapeptaibol, trichosporin B-VIa, and its Aib14-substituted derivative containing no Pro were investigated on the basis of CD and various NMR experiments in methanol. Trichosporin B-VIa has a fully helical structure with a kink stabilized by a 1←4 hydrogen-bond between the Leu12 CO and Val15 NH. The helical structure is composed of 310-helix in the N-terminal first turn and the C-terminal moiety following Leu12, and α-helix in the middle region. In contrast, the Aib14 derivative predominantly has a straight α-helical structure except for a 310-helix region in the N-terminal first turn.View full abstractDownload PDF (785K) -
Masashi HASEGAWA, Atsushi NAKAYAMA, Shuichi YOKOHAMA, Toru HOSOKAMI, Y ...1995 Volume 43 Issue 7 Pages 1125-1131
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of exomethylenic bicyclic thiazoline derivatives (3a-i) was synthesized and evaluated for hepatoprotective activity against galactosamine-induced and monoclonal antibody-induced acute liver injuries in rats. The structure-activity relationships were investigated. Among the compounds synthesized, N-methyl-(7-isopropoxycarbonyl-6, 6-dimethyl-2, 3, 5, 6-tetrahydropyrrolo[2, 1-b]thiazol-3-ylidene)acetamide (3i) exhibited the most potent hepatoprotective activity. This compound suppressed galactosamine-induced hepatic injury at 100 mg/kg by oral administration and further prevented monoclonal antibody-induced hepatic injury at 30 mg/kg by intraperitoneal injection, as judged from the changes in serum transaminase activities.View full abstractDownload PDF (969K) -
Yutaka KAWASHIMA, Masakazu SATO, Satoko YAMAMOTO, Yuki SIMAZAKI, Yoshi ...1995 Volume 43 Issue 7 Pages 1132-1136
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe have recently reported that 4-[2-(4-substituted phenylsulfonylamino)ethylthio]phenoxyacetic acids and related compounds showed potent thromboxane A2 (TXA2) receptor antagonist activity. To understand how substituents affect the biological activity, the quantitative structure-activity relationship (QSAR) was analyzed by using the Hansch-Fujita method for 36 compounds, including newly synthesized compounds. The positive coefficient for πR and FR in the results of the QSAR study suggested that a hydrophobic and σ electron-withdrawing substituent R at the para-position of the phenylsulfonyl moiety is required to improve the activity. Further, a substituent R which is long and moderately wide, was suggested to be preferable for the activity. The positive coefficients for πX, Y, W-COOH and ΣQ(1)-(6) may indicate that the introduction of a hydrophobic and electron-withdrawing group on the benzene ring of the phenoxy acetic acid moiety enhances the activity. The length of the W-COOH moiety may also be important. On the other hand, the effect of the presence of methylene (n=1) was not clear.View full abstractDownload PDF (764K) -
toshiya MORIE, Shiro KATO, Hiroshi HARADA, Naoyuki YOSHIDA, Iwao FUJIW ...1995 Volume 43 Issue 7 Pages 1137-1147
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new series of 4-amino-5-chloro-2-ethoxybenzamides 3b-f and 5-8 bearing six and seven-membered heteroalicycles was prepared and evaluated for gastroprokinetic activity. Compounds 3b-e, derived by replacement of the morpholine oxygen of 4-amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-ethoxybenzamide (3a) with other atoms (sulfur, nitrogen and carbon), generally exhibited a potent gastric emptying activity. N-(4-Benzyl-3-morpholinyl)methylbenzamide (5a) and its analogues 5b-e had weaker activity. However, N-(4-benzyl-3-morpholinyl)ethylbenzamide 8 was as potent as 3a. Benzamides 6a-e, having seven-membered heteroalicycles, showed fairly potent activity.Molecular superimpositions of 5a, 6a and 8 upon 3a using computer graphics suggested that the direction of the N-benzyl group greatly influences the gastric emptying activity, whereas the location of the alicyclic nitrogen is less critical.View full abstractDownload PDF (1465K) -
Naoki SAKURA, Katsuro KUROSAWA, Tadashi HASHIMOTO1995 Volume 43 Issue 7 Pages 1148-1153
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthetic dog neuromedin U-25(d-NMU-25), U-8(d-NMU-8) and their fragments were examined for contractile activity on chicken crop smooth muscle preparation. The relative activities of d-NMU-25, d-NMU-25 (15-25)-NH2 and d-NMU-8 to porcine neuromedin U-8 (p-NMU-8) were 1.69, 2.54 and 5.78, respectively. High activity of d-NMU-8 may be attributable to the N-terminal pGlu residue, which provides resistance to aminopeptidases. Various NMU-8 analogs, having various amino acids, Nα-acetylated amino acids, D-amino acids, or simple organic acids at position 1, were synthesized and evaluated for contractile activity. None of the substitutions caused a significant decrease of the biological activity. Modification at the N-terminal to give aminopeptidase resistance produced analogs with increased contractile activity, presumably because they were not degraded by soluble enzymes released into the bioassay fluid from isolated chicken crop tissue.View full abstractDownload PDF (948K) -
Tadashi HASHIMOTO, Katsuro KUROSAWA, Naoki SAKURA1995 Volume 43 Issue 7 Pages 1154-1157
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo develop a highly potent agonist and to examine the structure-contractile activity relationship of neuromedin U-8 (NMU-8), seventeen analogs were synthesized and tested for contractile activity on isolated chicken crop smooth muscle preparations. The analogs were designed to examine the contributions of cyclic structure and acidic function at the N-terminal of NMU-8 and NMU-8 (2-8) to the biological activity. The relative activity (RA) values of NMU-8 analogs were as follows : [D-pGlu1]-NMU-8, 5.50; [pyrohomoglutamyl (pHgu)1]-NMU-8, 4.65; [D-pHgu1]-NMU-8, 4.66; [Asp1]-NMU-8, 11.4; [acetyl(Ac)-Asp1]-NMU-8, 9.81; [Ac-Glu1]-NMU-8, 18.6; [succinyl (Suc)-Tyr1-NMU-8, 69.3; [3-sulfoalanyl (Sal)1]-NMU-8, 12.7. The RA values of NMU-8 (2-8) analogs were as follows : α-picolinyl (Pic)-NMU-8 (2-8), 7.96; 2-furoyl (Fur)-NMU-8 (2-8), 9.91; 2-thiophenecarbocyl (Thi)-NMU-8 (2-8), 3.41; 4-hydroxyphenylpropinyl (Hpp)-NMU-8 (2-8), 3.20; o-phthalyl (Pht)-NMU-8 (2-8), 11.3; Suc-NMU-8 (2-8), 109; malonyl (Mlo)-NMU-8 (2-8), 17.9; maleyl (Mle)-NMU-8 (2-8), 31.6; glutaryl (Glt)-NMU-8 (2-8), 81.3; The potencies of the analogs were higher than that of p-NMU-8. Suc-NMU-8 (2-8) showed the highest potency among the analogs synthesized. The results reveal that the carboxylic acid group at the N-terminus of NMU-8 makes a major contribution to the activity.View full abstractDownload PDF (786K) -
Fumiyo KUSU, Katsumi MATSUMOTO, Kiyoko TAKAMURA1995 Volume 43 Issue 7 Pages 1158-1161
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHigh-performance liquid chromatography (HPLC) with electrochemical detection using a chiral ligand-exchange column (Sumichiral OA-5000) and a mobile aqueous phase containing 1 mM copper(II) acetate and 20 mM ammonium acetate (pH 6.4) was applied to the direct separation and determination of synephrine enantiomers. The calibration curve for each enantiomer showed good linearity (r=0.999) over a concentration range of 0.2-100 μM with a detection limit of 0.2 μM (signal-to-noise ratio (S/N)=3). As far as reproducibility was concerned, the relative standard deviation (R.S.D.) was 2.6% at 20 μM d-synephrine and 2.4% at 20μM-l-synephrine. The degradation and optical isomerization of l-synephrine in Citrus unshiu were caused by ultraviolet (UV) light or heat. The synephrine enantiomers in citrus plants, crude drugs and Chinese medicines were determined by the present method.View full abstractDownload PDF (667K) -
Toshihiro INOUE, Yoshihiro MIMAKI, Yutaka SASHIDA, Masato KOBAYASHI1995 Volume 43 Issue 7 Pages 1162-1166
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe full structures of the two steroidal saponins from Narthecium asiaticum MAXIM. we previously identified as toxic substances by monitoring the toxicity in guinea pigs were phytochemically reinvestigation on the aerial parts of the plant. The desired toxic saponins (6, 7) were isolated together with two known lignan glucosides (1, 2), a known flavonoid glucoside (3), a new furanone glucoside (4), a known steroidal saponin (5) and a new steroidal saponin (8). The structures of the new furanone glucoside, toxic saponins and new saponin were determined on the basis of spectroscopic data and acid- or enzymatic-catalyzed hydrolysis to be (S)-5-β-D-glucopyranosyloxy-4-methoxyfuran-2(5H)-one (4), (25R, S)-5β-spirostan-3β-ol 3-O-{O-β-D-glucopyranosyl-(1→2)-O-[α-L-arabinopyranosyl-(1→3)]-β-D-galactopyranoside} (6), (25R, S)-5β-spirostan-3β-ol 3-O-{O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-β-D-galactopyranoside} (7) and (24S, 25R)-5β-spirostane-3β, 24-diol 3-O-{O-β-D-glucopyranosyl-(1→2)-O-[α-L-arabinopyranosyl-(1→3)]-β-D-galactopyranoside} (8), respectively.View full abstractDownload PDF (860K) -
Akiko KUSANO, Makio SHIBANO, Genjiro KUSANO1995 Volume 43 Issue 7 Pages 1167-1170
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour new glycosides (1-4) were isolated from the aerial parts of Cimicifuga simplex (Ranunculaceae), and their structures were determined to be 12β-hydroxycimigenol-3-O-β-D-xylopyranoside (1), 12β-hydroxycimigenol-3-O-α-L-arabinopyranoside (2), 7β-hydroxycimigenol-3-O-β-D-xylopyranoside (3) and 25-O-acetyl-7β-hydroxycimigenol-3-O-β-D-xylopyranoside (4).View full abstractDownload PDF (649K) -
Hideji ITOKAWA, Zhi-Sheng QIAO, Chieko HIROBE, Koichi TAKEYA1995 Volume 43 Issue 7 Pages 1171-1175
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe ethanolic extract of the root bark of Melia azedarach exhibited cytotoxic activity against lymphocytic leukemia P388 cell lines in vitro. Systematic fractionation of the extract monitored by cytotoxic bioassay led to the isolation of two new azadirachtin-type limonoids, 1-tigloyl-3-acetyl-11-methoxymeliacarpinin (1) and 1-acetyl-3-tigloyl-11-methoxymeliacarpinin (2), together with three highly cytotoxic sendanin-type limonoids, 29-isobutylsendanin (3), 12-hydroxyamoorastin (4) and 29-deacetylsendanin (5). The accetylated derivatives of 4 also underwent cytotoxic bioassay.View full abstractDownload PDF (686K) -
Tomonori ARAO, Junei KINJO, Toshihiro NOHARA, Ryuichi ISOBE1995 Volume 43 Issue 7 Pages 1176-1179
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA continuing study of the ingredients of Puerariae Radix, the roots of Pueraria lobata (WILLD.) OHWI, which is one of the most important crude drugs, has resulted in the first isolation of four new oleanene-type triterpene glycosides, named kudzusaponins SA1, SA2, SA3 and C1 (1-4). Their structures were determined to be 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A (1), 3-O-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 22-O-α-L-arabinopyranoside (2), 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl soyasapogenol A 22-O-α-L-arabinopyranoside (3) and 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyranosyl kudzusapogenol C 21-O-β-D-glucopyranoside (4), respectively. The usefulness of tandem mass spectrometry in the structural determination of oleanene-type triterpene bisdesmosides is also discussed.View full abstractDownload PDF (728K) -
Yoko TAKAASHI, Yoshihiro MIMAKI, Aiko KAMEYAMA, Minpei KURODA, Yutaka ...1995 Volume 43 Issue 7 Pages 1180-1185
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFresh stems of Nolina recurvata were found to contain three new cholestane bisdesmosides. Their structures were determined on the basis of spectroscopic data and acid-catalyzed hydrolysis to be (22S)-cholest-5-ene-1β, 3β, 16β, 22-tetrol 1-O-β-D-glucopyranoside 16-O-α-L-rhamnopyranoside (1), (22S)-cholest-5-ene-1β, 3β, 16β, 22-tetrol 1, 16-di-O-β-D-glucopyranoside (2) and (22S)-cholest-5-ene-1β, 3β, 16β, 22-tetrol 1-O-{O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside} 16-O-α-L-rhamnopyranoside (3), respectively. The prominent downfield shift of the aglycone 19-Me of 3, compared with that of 1 and 2, is likely caused by the interaction between the 19-Me and 6'''-Me of the rhamnose attached to C-2 of the inner glucose, evidence for which was provided through molecular mechanics and molecular dynamics calculation studies and by the nuclear Overhauser effect (NOE) correlation spectrum. The isolated compounds and their derivatives were evaluated for their inhibitory activity on cAMP phosphodiesterase and Na+/K+ ATPase.View full abstractDownload PDF (946K) -
Yoshiki MINO1995 Volume 43 Issue 7 Pages 1186-1189
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe complete amino acid sequences of [2Fe-2S] ferredoxins from Datura quercifolia (section Stramonium) and D. fastuosa (section Dutra) have been determined by automated Edman degradation of the entire Cm-protein and of the peptides obtained by tryptic digestion and CNBr treatment. The D. quercifolia and D. fastuosa ferredoxins exhibited identical amino acid sequences to D. stramonium (section Stramonium) and D. metal (section Dutra) ferredoxins, respectively. This result suggests that the amino acid sequence of Datura ferredoxins depends on the section but not the species of Datura plants.View full abstractDownload PDF (602K) -
Yoshihiro MIMAKI, Toshihiro KANMOTO, Minpei KURODA, Yutaka SASHIDA, At ...1995 Volume 43 Issue 7 Pages 1190-1196
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhytochemical study on the underground parts of Hosta longipes gave six new steroidal saponins together with a known one. The structures of the new compounds were determined by detailed analysis of their 1H-and 13C-NMR spectra including two-dimensional NMR spectroscopy, acid-catalyzed hydrolysis followed by chemical correlation, and by comparison with spectral data of known compounds. The isolated saponins and their aglycones were examined for inhibitory activity on 12-O-tetradecanoylphorbol-13-acetate (TPA)-stimulated 32P-incorporation into phospholipids of HeLa cells to identify new antitumor-promoter compounds.View full abstractDownload PDF (1015K) -
Yoshihiro AOKI, Yoshiharu YAMADA, Kazumi DANJO, Yorinobu YONEZAWA, His ...1995 Volume 43 Issue 7 Pages 1197-1203
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSComputer simulation was carried out to elucidate the growth rate and morphological change of aggregates in flocculation with compaction of monodisperse system by a procedure based on a two-dimensional geometrical random coalescence model. Aggregates were packed closely by partial rotation of the cluster constituting the aggregate when aggregates were flocculated (compaction A) or during measurement of flocculation time (compaction B). Flocculation kinetics were in good agreement with Smoluchowski's flocculation theory. In both compaction methods, the aggregates were packed closely, so that parameters such as the compaction probability and frequency would apply. The aggregates formed by flocculation had hollow structures resembling thick trunks and/or loop structures when they became large. The growth rate of aggregates followed second-order kinetics in both methods. The growth rate constant did not vary with compaction probability in compaction A, but became minimal when the product of compaction probability and compaction frequency was approximately 0.5 in compaction B. Changes in anisometry of aggregates were different for the two methods, that in anisometry simulated by compaction B was more consistent with the date for actual flocculation from a two-dimensional model experiment than change in this parameter simulated by compaction A.View full abstractDownload PDF (837K) -
Tsuneo HAMAGUCHI, Denji SHINKUMA, You YAMANAKA, Masatoshi MIYAKE, Shig ...1995 Volume 43 Issue 7 Pages 1204-1211
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bioavailability of sulpiride (SP) from a tablet coated with AEA [○!R] (polyvinylacetal diethylaminoacetate), used as a gastric-fluid-soluble polymer, is very poor in low gastric acidity subjects in the fasting state but improves after food intake. To analyze the factors affecting SP bioavailability from an AEA [○!R] film-coated tablet (AEA [○!R] tablet), we prepared AEA [○!R] cast film and AEA [○!R] tablets and investigated the physicochemical properties of gastrointestinal (GI) fluids affecting the dissolution of the film coating and the dissolution rate of SP from the tablets. The dissolution time of AEA [○!R] cast film was shortened with an increase in the ionic strength of the medium, but was delayed by an increase in viscosity and addition of sodium taurocholate to the medium. The AEA [○!R] tablet showed rapid dissolution of SP at pH 4 or below but not when the pH was 5.0 or above. In pH 5.0-5.8 media, the SP dissolution rate from the tablet increased as the ionic strength (μ) of the medium rose, reaching maximum at μ=0.3. Microscopic observations and measurements of film coating thickness revealed that the increased dissolution rate of SP from the tablet with higher ionic strength (μ=0.3) was due to promotion of the dissolution of the AEA [○!R] film coating. Data from pH titration showed that increased ionic strength (μ=0.3) resulted in higher apparent dissociation, which increased the solubility of AEA [○!R] in the medium. We concluded that the ionic strength in GI fluids is one of the factors affecting the bioavailability from AEA [○!R] tablet. After food intake, the bioavailability of SP from the tablet improves, probably due to increased apparent dissociation of AEA [○!R] caused by an increase in ionic strength from the meal (ca. μ=0.3). This increases the dissolution rate of the film coating and thus, the dissolution rate of SP from the AEA [○!R] tablet, leading to enhanced absorption.View full abstractDownload PDF (1305K) -
Satoru WATANO, Yoshinobu SATO, Kei MIYANAMI, Takayuki MURAKAMI, Yoshih ...1995 Volume 43 Issue 7 Pages 1212-1216
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGranulation scale-up with an agitation fluidized bed of three sizes (vessel diameter 125, 230, 500 mm) was preliminary investigated. In order to evaluate accurately the scale-up factor on granule properties, process variables such as spray conditions, method for moisture measurement and control, powder feed weight and drying efficiency were optimized.View full abstractDownload PDF (727K) -
Satoru WATANO, Yoshinobu SATO, Kei MIYANAMI, Takayuki MURAKAMI, Nobuma ...1995 Volume 43 Issue 7 Pages 1217-1220
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSScale-up characteristics of agitation fluidized bed granulation using a pharmaceutical standard formulation was described. The effects of scale, air flow velocity and agitator rotational speed on granule properties such as granule mass median size, size distribution, apparent density and shape factor were investigated experimentally. Based on the results obtained, the effects of these parameters on granule growth and the mechanism of granule formation in different sized equipment were discussed.View full abstractDownload PDF (678K) -
Tomoko OTSUKA, Sumie YOSHIOKA, Yukio ASO, Shigeo KOJIMA1995 Volume 43 Issue 7 Pages 1221-1223
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dynamics of water molecules associated with water-soluble polymers were studied by 17O-NMR. The observed spin-lattice relaxation time, T1(obs), of water in aqueous solutions of polyethylene glycol (PEG), poly(vinylpyrrolidone) (PVP) and gelatin at polymer concentrations below 0.12 g/g of water could be described by an isotropic two-state model with a fast exchange. The tendency for the polymers to reduce the T1(obs) of water was on the oreder of PEG<gelatin<PVP. At higher concentrations, deviations from the model were observed for PVP and gelatin. The T1(obs) of water in the PEG solution was not affected by the molecular weight of the polymer. This suggests that the microviscosity around the polymer molecules is governed by the interaction between the polymer unit and water molecules, and is not affected by the molecular weight of polymers in contrast to the "macroviscosity". The polymer-water interaction that reduced the T1(obs) of water was found to decrease with increasing temperature for all the polymers studied. The T1(obs) of water in the gelatin solution exhibited the largest temperature dependence, suggesting that changes might occur in the molecular structure of gelatin at higher temperatures.View full abstractDownload PDF (545K) -
Satoru WATANO, Yoshinobu SATO, Kei MIYANAMI, Yoshihiro ITO, Tetsuro KA ...1995 Volume 43 Issue 7 Pages 1224-1226
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis paper presents the experimental results of a study on the scale-up characteristics of granule comopaction and sphericity in an agitation fluidized bed granulation. A pharmaceutical standard formulation was granulated using agitation fluidized bed of three sizes (vessel diameter : 125, 230, 500 mm). The effects of powder feed weight and agitator blade angle on the granule properties of size, density and shape were studied. It was found that granules were compressed and made spherical with an increase in agitator blade angle and vessel scale, while they were not influenced by the powder feed ratio.View full abstractDownload PDF (500K) -
Satoru WATANO, Yoshinobu SATO, Kei MIYANAMI1995 Volume 43 Issue 7 Pages 1227-1230
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe scale-up theory based on kinetic energy similarity was proposed to elucidate the scale-up characteristics in agitation fluidized bed granulation. In this model, kinetic energy given to granules by agitator rotation and fluidizing air were taken into consideration. It was found that granule mass median diameter, apparent density and shape factor can be well expressed by the parameter (Rω/u)2, which showed the ratio of kinetic energy by agitator rotation to that by fluidizing air. Based on the results obtained, effects of operational variables and scale factor on the granule properties could be explained theoretically and granule growth mechanism in agitation fluidized bed granulation was elucidated in detail.View full abstractDownload PDF (650K) -
Tadashi MAKINO, Nobuyuki KITAMORI1995 Volume 43 Issue 7 Pages 1231-1233
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSParticle size distribution of fine granules produced by agitation granulation was investigated as a function of the concentration of starch paste. The time course of granulation was investigated in a high speed type mixer using 5% starch paste having a good fluidity and 15% starch paste having no fluidity at all, like a gel. In agitation granulation, aggregation and deaggregation of particles and/or granules occurred simultaneously.At a low concentration of starch paste, massing of the granules, namely the growth of granules, occured mainly during the agitation granulation, since the relatively large amount of free water was available from the paste. Therefore, in this case, only the mean size shifted toward a larger measurement without any change in the width of the granules during the granulation.At a high concentration of starch paste, rapid deaggregation of granules by shear force applied occurred following the formation of large granules immediately after the addition of paste. Since a small amount of water exudes from the paste during the agitation, massing proceeds slowly. This means that in the case of granulation using a high concentration of starch paste, deaggregation proceeds predominantly, so that the size distribution of the granules becomes more narrow. Fine granules may be produced by agitation granulation when a high concentration of starch paste is used and when granulation is executed under sufficient shear or rotation speed that guarantees satisfactory dispersion of the gel.View full abstractDownload PDF (580K) -
Enrique RAVINA, Jose CID, Jesus NEGREIRA, Maria E. CASTRO, Victor M. M ...1995 Volume 43 Issue 7 Pages 1234-1237
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStarting from the methyl ester of β-(bromomethyl)-γ-phenylbutyric acid and its m-fluoro derivative, we have prepared 2-[4[3-(p-fluorobenzoyl)-1-propyl]piperazin-1-ylmethyl]tetraline (QF0105B) and the corresponding 7-fluoro derivative (QF0106B). The affinities of these compounds for D1 and D2 dopamine and 5-HT2A receptors was evaluated in vitro. The afinities of QF0105B and QF0106B for D2 receptors are less than that of haloperidol (pKi's for inhibition of [3H]spiperone binding : 7.72, 7.06 and 8.30, respectively) but all three compounds have similar affinities for 5-HT2A receptors (pKi'S for inhibition of [3H]ketanserine binding : 7.70, 7.36 and 7.70, respectively).View full abstractDownload PDF (736K) -
Jun SEGAWA, Kenji KAZUNO, Masato MATSUOKA, Isao AMIMOTO, Masakuni OZAK ...1995 Volume 43 Issue 7 Pages 1238-1240
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically active isomers of 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1, 3]thiazeto[3, 2-a]quinoline-3-carboxylic acid (NM394, 3) were prepared through optical resolution of their racemic intermediate (±)-1 by high-performance liquid chromatography (HPLC). The absolute configuration at the C-1 position in the thiazetoquinolone ring of (-)-3 was confirmed by X-ray analysis of (-)-4 to be S. The in vitro antibacterial activity of (-)-3 was 2-8 times that of (+)-3.View full abstractDownload PDF (513K) -
Yukio SATO, Zhansong CHEN, Yasuo SUZUKI1995 Volume 43 Issue 7 Pages 1241-1244
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThis paper reports on the study of the influence of hopanoids, bacteriophopane-32-ol (Monol) and bacteriophopane-32, 33, 34, 35-tetrol (Tetrol) on the phospholipid membranes formed from dimyristoylphosphatidylcholines (DMPC) or bacterial phospholipids (BPL). Maximum splitting values and rotational correlation times were evaluated from the ESR spectra of 5- and 16-doxylstearic acids incorporated into these membranes. The effects of Monol on the DMPC membranes depended on both the phase transition temperature of DMPC (Tm : 23°C) and the distance from the membrane surface. These effects of Monol were similar to those of cholesterol (Chol). The effects of Tetrol and Chol on the BPL membranes were similar to those of Monol and Chol on the DMPC membranes. However, the effects of Monol on the BPL membranes were different from those of Tetrol and Chol. It was found that the values of activation energy (Ea) and activation entropy change (ΔS*) in the Monol-DMPC, Chol-DMPC, Tetrol-BPL and Chol-BPL systems were smaller than those in DMPC or BPL alone. Such characteristic effects of Monol and Tetrol on the liposomal membranes were compared with those of Chol.View full abstractDownload PDF (758K) -
Masayuki YOSHIKAWA, Hiromi SHIMADA, Hiroshi SHIMODA, Hisashi MATSUDA, ...1995 Volume 43 Issue 7 Pages 1245-1247
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new antiallergic cyanoglycosides named rhodiocyanosides A and B were isolated from the Chinese natural medicine "Si Lie Hong Jing Tian" (Shiretsukoukeiten in Japanese), the underground part of Rhodiola quadrifida (Pall.) Fisch. et Mey., together with two new glycosides, octyl α-L-arabinopyranosyl(1-6)-β-D-glucopyranoside and gossypetin 7-O-β-D-glucopyranosyl(1-3)-α-L-rhamnopyranoside. Their chemical structures were determined on the basis of chemical and physicochemical evidence. Rhodiocyanosides A and B exhibited inhibitory activity on the histamine release from rat peritoneal exudate cells sensitized with anti-DNP IgE. In addition, rhodiocyanoside A was found to inhibit the PCA reaction in rats.View full abstractDownload PDF (509K) -
Yukihiro GODA, Shiho SAKAMOTO, Toshiyuki NAKANISHI, Tamio MAITANI, Tak ...1995 Volume 43 Issue 7 Pages 1248-1250
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCapsanthin esters were separated from paprika (Capsicum annuum) oleoresin, and their structures were determined without saponification. The major monoesterified capsanthin was identified as 3'-O-myristoylcapsanthin. 3-O-Esterified capsanthins were not detected, although 3, 3'-O-diesterified capsanthins with saturated fatty acids were isolated. The results suggest that the rate in esterification of fatty acid to the hydroxyl group on the cyclopentane ring of capsanthin is different from that on the cyclohexene ring.View full abstractDownload PDF (548K) -
Hirosato EBIIKE, Yukiyoshi YAMAZAKI, Kazuo ACHIWA1995 Volume 43 Issue 7 Pages 1251-1253
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHomochiral 4-Aryl-1, 4-dihydropyridine-5-phosphate (NZ 105) was synthesized from the racemic materials. The enantioselective hydrolysis by lipase catalyst was smoothly proceeded and optically active carboxylic acid was converted into optically active medicine.View full abstractDownload PDF (466K) -
Hiroto NAKANO, Kazuto IWASA, Chizuko KABUTO, Hisao MATSUZAKI, Hiroshi ...1995 Volume 43 Issue 7 Pages 1254-1256
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically active photopyridones possessing synthetic versatility were obtained conveniently by lipase-catalyzed enantioselective acylation or hydrolysis of racemic photopyridones, and the absolute configurations were determined by chemical correlation, X-ray crystallography and CD spectral analysis.View full abstractDownload PDF (487K) -
Minpei KURODA, Yoshihiro MIMAKI, Yutaka SASHIDA, Toshihiko HIRANO, Kit ...1995 Volume 43 Issue 7 Pages 1257-1259
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel 16, 23-epoxy-5β-cholestane triglycoside (1) was isolated from the bulbs of Ornithogalum saundersiae (Lilaceae). The structure was determined by extensive spectroscopic analysis. The conformation of the E-ring part of 1 was studied through molecular mechanics and molecular dynamics calculation methods. Compound 1 potently inhibited proliferation of peripheral blood lymphocytes provided from a chronic renal failure patient without causing any cytotoxicity in the lymphocytes and HL-60 human leukemia cells.View full abstractDownload PDF (466K) -
Hideyuki ITO, Yoko MIYAKE, Takashi YOSHIDA1995 Volume 43 Issue 7 Pages 1260-1262
Published: July 15, 1995
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new piscicidal triterpenens named irisgermanicals A, B and C along with seven known iridal-type triterpenes including iripallidal and iriflorental were isolated from the bark of Iris germanica rhizome, upon bioassay-guided fractionation using the Medaka (killie-fish; Oryzias latipes), and their bicyclic structures were elucidated based on the spectral analyses. Irisgermanicals B and C were characterized as geometrical iriflorental and iripallidal isomers, respectively, concerning the α, β-unsaturated aldehyde moiety. The piscicidal activity was observed for bicyclic iridals, among which iriflorental exhibited most potent activity.View full abstractDownload PDF (477K)
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