Chemical and Pharmaceutical Bulletin
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ISSN-L : 0009-2363
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Volume 52, Issue 10
Displaying 1-28 of 28 articles from this issue
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Regular Articles
  • Determination of Optimal Formulation for Extrusion Granulation by Compression Test of Wet Kneaded Mass
    Yoshito Ohnishi, Takumi Okamoto, Satoru Watano
    2004 Volume 52 Issue 10 Pages 1155-1161
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1155
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    The purpose of this study is to propose the application of a compression test to the determination of an optimal formulation for extrusion granulation. The electric current during extrusion was measured and the characteristics of the wet kneaded mass in the compression test were analyzed under various operating conditions, with different types of extruders and several formulations of kneaded mass. It was found that addition of a binder (HPC-L) to pharmaceutical powders lowered the load of a high-compressing type extruder, since the binder reduced the friction among the wet mass during extrusion. Also, the support stress was found to be proportional to the compression pressure without a binder, although an inflection point appeared on the support stress curve when a binder was present. This inflection point suggested large water retention of the wet kneaded mass, at which the medium of pressure was changed from a discontinuous solid powder to a continuous liquid, and large water retention contributed to the low friction of the wet mass. The friction of the wet kneaded mass and the aptitude of the formulation for extrusion were understood by using the compression test. The compression test is a very useful procedure at the first stage of a formulation study.
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  • Synthesis and Anticancer Activities of 5,6,7-Trimethylbaicalein Derivatives
    Hua-Lin Liao, Ming-Kuan Hu
    2004 Volume 52 Issue 10 Pages 1162-1165
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1162
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    The aim of this study was to develop potential anticancer agents based on a naturally occurring baicalein, a flavonoid from Scatellariae radix. Cinnamic acid derivatives were converted to corresponding chlorides and then condensed with 3,4,5-trimethoxyphenol in the presence of BF3·Et2O to give chalcones. Intramolecular cyclization of these intermediates by the actions of DMSO/I2 afforded the desired trimethylbaicalein derivatives. Cell viability after treatment with the tested compound for 2 d was determined by a colorimetric MTT assay. The results indicated that most of the derivatives showed improved inhibition of proliferation of Hep G2 cells. Compound 9 was the most potent, in which the cell viability was reduced to <2% at the 25 μM level. In the case of Hep 3B cells, 8a, 8b and 8f showed moderate inhibition of their proliferation and 25 μM was required to reduce the viability to ca. 30%. On the other hand, prostate DU145 cells were more resistant. Most of the derivatives caused a 60% inhibition of DU145 cells only at a concentration of 100 μM or above.
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  • A Comparative Study of First-Derivative Spectrophotometry and High-Performance Liquid Chromatography Applied to the Determination of Losartan Potassium in Tablets
    Mehdi Ansari, Maryam Kazemipour, Freshteh Khosravi, Mehdi Baradaran
    2004 Volume 52 Issue 10 Pages 1166-1170
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1166
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    Losartan, a highly effective blood pressure-lowering agent, has been widely used for the treatment of hypertension. A fast and reliable method for the determination of losartan was highly desirable to support formulation screening and quality control. A first-derivative UV spectroscopic method and HPLC were developed for the determination of losartan in the tablet dosage form. The first-derivative spectrum recorded between 220 and 320 nm and a zero-crossing technique for first-derivative measurement at 232.5 nm were selected. The selectivity and sensitivity of the method was in desirable range. In comparison with the direct UV method, first-derivative UV spectroscopy has a definite trough without any interference from UV absorbing-excipients. This method is also fast and economical in comparison with the more time-consuming HPLC method regularly used for formulation screening and quality control and can be used routinely by any laboratory possessing a spectrophotometer with a derivative accessory. The linear concentration ranges were 2—50 μg ml−1, (D1=−0.0159C−0.0056, r=0.9994, n=6). Between-days CV of ≤2.9%, within-day CV of ≤2.1%, and analytical recovery close to 98.1% show the suitability of the method for determination in quality control.
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  • Novel Squalene-Hopene Cyclase Inhibitors Derived from Hydroxycoumarins and Hydroxyacetophenones
    Giancarlo Cravotto, Gianni Balliano, Silvia Tagliapietra, Simonetta Ol ...
    2004 Volume 52 Issue 10 Pages 1171-1174
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1171
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    Squalene-hopene cyclase (SHC) is a useful model enzyme for predicting molecular interactions with oxidosqualene cyclase (OSC). Structure–activity relationships were investigated for numerous coumarin-derived inhibitors of SHC, and structural simplifications are suggested. Both umbelliferone and 2,4-dihydroxyacetophenone provide convenient starting nuclei for the design of SHC inhibitors. Derivatives bearing an ω-epoxyfarnesyl moiety or just a plain alkyl chain showed an inhibitory effect on a recombinant SHC from Alicyclobacillus acidocaldarius expressed in Escherichia coli.
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  • A New Dimeric Carbazole Alkaloid from Glycosmis stenocarpa Roots
    Nguyen Manh Cuong, Tran Quang Hung, Tran Van Sung, Walter Chacles Tayl ...
    2004 Volume 52 Issue 10 Pages 1175-1178
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1175
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    A new dimeric pyranocarbazole alkaloid, bisisomahanine (1), was isolated from the roots of Glycosmis stenocarpa (DRAKE) TAN., along with two known monomeric carbazole alkaloids, murrayafoline-A (2) and murrayanine (3). The planar structure of bisisomahanine was determined to be 9,9″-dihydroxy-3,3″,8,8″-tetramethyl-3,3″-bis-(4-methyl-3-pentenyl)-3,3″,11,11″-tetrahydro-10,10″-(bipyrano[3,2-a]carbazole) from the combination of spectroscopic and chemical evidence. Bisisomahanine is the first dimeric prenylated pyranocarbazole alkaloid with a 1,1′ type of linkage; the NMR and CD spectroscopic data indicated it to be a mixture of diastereomers having a dominant configuration at the axis of chirality. 1H- and 13C-NMR assignments of murrayafoline-A were made on the basis of 2D-experiments.
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  • Binding Properties of Adenosine Deaminase Interacted with Theophylline
    Ali Akbar Saboury, Soghra Bagheri, Ghasem Ataie, Masoud Amanlou, Ali A ...
    2004 Volume 52 Issue 10 Pages 1179-1182
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1179
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    Thermodynamic studies were carried out to evaluate the binding of theophylline on adenosine deaminase (ADA) in 50 mM sodium phosphate buffer pH 7.5, at 300 K, using isothermal titration calorimetry (ITC). A simple method for determination of binding isotherm in the drug–ADA interaction was applied using ITC data. ADA has two binding sites for theophylline, which show positive cooperativity in its sites. The intrinsic association equilibrium constants are 6 and 52 mM−1 in the first and second binding sites, respectively. Hence, occupation of the first site has produced an appreciable enhancement by 8.7 of the binding affinity of the second site. The molar enthalpies of binding are −12.2 and −14.9 kJ/mol in the first and second binding sites, respectively.
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  • Adsorption of Bile Acid by Chitosan-Orotic Acid Salt and Its Application as an Oral Preparation
    Yoshifumi Murata, Sayuri Kudo, Kyouko Kofuji, Etsuko Miyamoto, Susumu ...
    2004 Volume 52 Issue 10 Pages 1183-1185
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1183
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    The orotic acid (OT) salt of chitosan (CS), CS-OT, and that of a CS derivative, CP, were prepared, and the adsorption of primary or secondary bile acid was investigated. Calcium-induced alginate gel beads (Alg-Ca) containing CS-OT were also prepared and autoclaved, and the possibility of these beads to act as a vehicle for oral administration to prevent hyperlipidemia was investigated. When taurocholate (TCA) and glycocholate (GCA) were present together in the medium, CS-OT adsorbed identical amounts of both bile acids. This trend was seen in all CPs, although the capacity to adsorb bile acid was affected by the number and/or structure of the amino groups in the CP. On the other hand, taurodeoxycholate, a secondary bile acid was preferentially adsorbed over TCA and GCA. Alg-Ca containing CS-OT took up bile acids in a similar manner as CS-OT irrespective of the water content of the gel matrix. As all elements can be taken as a food, Alg-Ca containing CS-OT could serve as a useful dietary agent for the prevention of hyperlipidemia, which is a lifestyle-related disease.
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  • Crystal and Molecular Structure of an (S)-(+)-Enantiomer of Modafinil, a Novel Wake-Promoting Agent
    Yasuko In, Koji Tomoo, Toshimasa Ishida, Yasuhiko Sakamoto
    2004 Volume 52 Issue 10 Pages 1186-1189
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1186
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    The (+)-enantiomer of modafinil [(RS)-2-(diphenylmethylsulfinyl)acetamide], a novel wake-promoting agent, was clarified to be S-configuration by X-ray crystal structure analysis. The crystal consists of two crystallographically independent conformers that are different at the torsion angles around the sulfinylacetamide moiety, and this results from the molecular packing requirement to form a two-dimensional hydrogen-bonding network via neighboring amide groups in the crystal. The crystal structure is characterized by the formation of alternative hydrophobic and hydrophilic layers, which are formed among the symmetry-translated assemblies of diphenylmethyl and sulfinylacetamide moieties, respectively. The spatial orientation between the diphenyl and amide groups is believed to be important for the activity of modafinil.
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  • New Diels-Alder Type Adducts from Morus macroura and Their Anti-oxidant Activities
    Sheng-Jun Dai, Yan Wu, Ying-Hong Wang, Wen-Yi He, Ruo-Yun Chen, De-Qua ...
    2004 Volume 52 Issue 10 Pages 1190-1193
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1190
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    Fractionation of the ethanolic extract of the stem bark of Morus macroura resulted in the isolation of four new Diels-Alder type adducts, named guangsangons K—N (1, 2, 5, 6), together with two known compounds, mulberrofuran G (3) and K (4). Their structures were determined on the basis of spectroscopic analyses and chemical methods. Furthermore, by means of 1H-NMR variable temperature experiments and the Cotton curves in the circular dichroism (CD) spectra, the stereochemistry of four new compounds was elucidated. The isolated new compounds showed good activity on anti-oxidant in vitro, with the inhibitory rates of MDA being from 91.8 to 100.0% at concentrations of 10−5 mol/l.
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  • Bioactive Constituents from Chinese Natural Medicines. XIV.
    New Glycosides of β-Carboline-Type Alkaloid, Neolignan, and Phenylpropanoid from Stellaria dichotoma L. var. lanceolata and Their Antiallergic Activities
    Toshio Morikawa, Bohang Sun, Hisashi Matsuda, Li Jun Wu, Shoichi Harim ...
    2004 Volume 52 Issue 10 Pages 1194-1199
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1194
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    A new β-carboline-type alkaloidal glycoside, glucodichotomine B, four new neolignan glycosides, dichotomosides A, B, C, and D, and a new phenylpropanoid glycoside, dichotomoside E, were isolated from a Chinese natural medicine, the roots of Stellaria dichotoma L. var. lanceolata. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence. Among them, dichotomoside D inhibited the release of β-hexosaminidase (IC50=64 μM) as well as tumor necrosis factor-α and interleukin-4 (IC50=16, 34 μM) in RBL-2H3 cells. These findings suggest that dichotomoside D is more effective against the late-phase reactions in type I allergy than in the immediate phase.
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  • Absolute Stereostructures of Polypodane-Type Triterpenes, Myrrhanol A and Myrrhanone A, from Guggul-Gum Resin (the Resin of Balsamodendron mukul)
    Hisashi Matsuda, Toshio Morikawa, Shin Ando, Hideo Oominami, Toshiyuki ...
    2004 Volume 52 Issue 10 Pages 1200-1203
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1200
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    Two new polypodane-type triterpenes, myrrhanol A and myrrhanone A, were isolated from the 50% aqueous methanolic extract of guggul-gum resin [the resin of Balsamodendron (=Commiphora) mukul HOOK.]. The structures of the new constituents, including their absolute configurations, were determined on the basis of chemical and physicochemical evidence.
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  • Synthesis and Biological Evaluation of Quinuclidine Derivatives Incorporating Phenothiazine Moieties as Squalene Synthase Inhibitors
    Tsukasa Ishihara, Hirotoshi Kakuta, Hiroshi Moritani, Tohru Ugawa, Isa ...
    2004 Volume 52 Issue 10 Pages 1204-1209
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1204
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    Squalene synthase inhibitors have the potential to be superior hypocholesterolemic agents. A series of quinuclidine derivatives incorporating phenothiazine systems was synthesized in order to investigate the effects of their structure on the inhibition of hamster liver microsomal enzyme. (±)-3-(10-Methyl-10H-phenothiazin-3-ylmethoxy)quinuclidine hydrochloride (19) was the most potent inhibitor in this series with an IC50 value of 0.12 μM. Oral dosing of compound 19 to hamsters demonstrated effective reduction of both plasma total cholesterol levels and plasma triglyceride levels. Compound 19 showed a reduced tendency to elevate plasma transaminase levels, an indicator of hepatotoxicity. Enantiomerically pure (−)-19, YM-53546, was found to be more potent than the corresponding (+)-enantiomer.
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  • Studies on the Constituents of Swertia japonica MAKINO I.
    On the Structures of New Secoiridoid Diglycosides
    Masafumi Kikuchi, Masao Kikuchi
    2004 Volume 52 Issue 10 Pages 1210-1214
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1210
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    Eight new secoiridoid diglycosides, 6′-O-α-L-arabinopyranosylswertiamarin (1), 3′-O-β-D-glucopyranosylswertiamarin (2), 4′-O-β-D-glucopyranosylswertiamarin (3), 3′-O-β-D-galactopyranosylswertiamarin (4), 6′-O-α-D-galactopyranosylswertiamarin (5), 6′-O-α-D-mannopyranosylswertiamarin (6), 6′-O-β-D-fructofuranosylswertiamarin (7) and 5″-O-β-D-glucopyranosylamaroswerin (12), were isolated, together with five known compounds from the whole plants of Swertia japonica MAKINO. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence. Compounds 6 and 7 are the first naturally occuring iridoid diglycosides having an α-D-mannopyranosyl unit and β-D-fructofuranosyl unit, respectively.
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  • Sesquiterpene Coumarins from Ferula fukanensis and Nitric Oxide Production Inhibitory Effects (2)
    Tsunetake Motai, Susumu Kitanaka
    2004 Volume 52 Issue 10 Pages 1215-1218
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1215
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    Four new sesquiterpene coumarin derivatives, fukanemarin B (1), fukanefuromarin E (2), fukanefuromarin F (3) and fukanefuromarin G (5) were isolated from a 80% aqueous methanol extract of the roots of Ferula fukanensis. The structures were elucidated based on spectral evidence, especially heteronuclear multiple-bond connectivity (HMBC) and high-resolution MS. The 80% aqueous methanol extract of the roots of Ferula fukanensis (FFE) and the sesquiterpene coumarin derivatives inhibited nitric oxide (NO) production and inducible NO synthase (iNOS) gene expression by a murine macrophage-like cell line (RAW 264.7), which was activated by lipopolysaccharide (LPS) and recombinant mouse interferon-γ (IFN-γ).
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  • Surface Tension Calculation of Mixed Solvents with Respect to Solvent Composition and Temperature by Using Jouyban–Acree Model
    Abolghasem Jouyban, Anahita Fathi-Azarbayjani, William Eugene Acree
    2004 Volume 52 Issue 10 Pages 1219-1222
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1219
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    Applicability of a solution model, i.e. Jouyban–Acree model (JAM), for calculating surface tension of binary and ternary solvents at various temperatures has been shown employing experimental surface tension data collected from the literature. The accuracy of the model was evaluated by calculating average percentage deviation (APD) between calculated and observed values. The obtained overall APD (±S.D.) for JAM using binary solvent data were 4.06 (±4.27) and 8.07 (±9.78)%, respectively for correlative and predictive analyses. The corresponding values for the best similar model from the literature were 8.86 (±6.40) and 37.10 (±27.65)% and the mean APD differences between JAM and previously published model were significant (p<0.003). The capability of JAM for correlating surface tension of ternary solvents at various temperatures was also shown and the overall APD was 1.39 (±0.37)%.
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  • Development of a Simple System for Dehydrocondensation Using Solid-Phase Adsorption of a Water-Soluble Dehydrocondensing Reagent (DMT-MM)
    Yasunobu Watanabe, Takako Fuji, Kazuhito Hioki, Shohei Tani, Munetaka ...
    2004 Volume 52 Issue 10 Pages 1223-1226
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1223
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    It has been indicated that hydrophilic solid powder to which aqueous solution of a novel dehydrocondensing reagent DMT-MM is adsorbed becomes a simple solid-phase dehydrocondensing reagent of low cost. Reaction in a liquid–liquid biphasic system on the surface of a solid phase with a large area was accelerated by suspending this powder in a dichloromethane solution of a carboxylic acid and an amine to be condensed. The reaction was rapid with a high yield despite the heterogeneity of the system. Like general solid-phase reagents, a hydrophobic carboxamide alone could be isolated at a relatively high purity only by filtration of the resulting suspension of reaction mixture.
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  • New Neolignans from Spiraea formosana
    Tian-Shung Wu, Chia-Chan Hwang, Ping-Chung Kuo, Tsung-Hsiao Kuo, Amoor ...
    2004 Volume 52 Issue 10 Pages 1227-1230
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1227
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    Phytochemical investigation on the ethanol extract from the stems of Spiraea formosana has resulted in the isolation of four new neolignans, named spiraformin-A, -B, -C and -D (1—4), together with thirty five known compounds. Their structures were established primarily on the basis of 1D and 2D NMR spectral and chemical transformation methods.
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  • A Novel and Concise Synthesis of Spirodienone Alkaloids Using Hypervalent Iodine(III) Reagents
    Hiromi Hamamoto, Yukiko Shiozaki, Kayoko Hata, Hirofumi Tohma, Yasuyuk ...
    2004 Volume 52 Issue 10 Pages 1231-1234
    Published: 2004
    Released on J-STAGE: October 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.1231
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    Intramolecular oxidative coupling reaction of N-protected benzyltetrahydroisoquinoline derivatives using hypervalent iodine(III) reagents was investigated. The use of remarkable combination of phenyliodine bis (trifluoroacetate) (PIFA) and heteropoly acid (HPA) in wet acetonitrile smoothly afforded morphinandienone alkaloids, while neospirinedienone alkaloids were obtained in high yield under anhydrous conditions.
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