Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 53, Issue 7
Displaying 1-34 of 34 articles from this issue
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Review
  • Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts
    Yoichi M. A. Yamada
    2005 Volume 53 Issue 7 Pages 723-739
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.723
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    I present herein the development of highly active and reusable polymeric catalysts produced by self-assembly process of non-cross-linked amphiphilic polymeric ligands with inorganic species. Thus, PWAA 1 prepared from H3PW12O40 and poly[(N-isopropylacrylamide)-co-(acrylamide with ammonium salt)] is suitable for oxidation of alcohols, amines, and sulfides in aqueous hydrogen peroxide. PdAS 2 produced by self-organization of (NH4)2PdCl4 and poly[(N-isopropylacrylamide)10-co-diphenylphosphinostyrene] is an excellent recyclable catalyst for Suzuki–Miyaura reaction in water, water-organic solvent, and organic solvent. It is commercially available from Tokyo Kasei Kogyo (TCI). PdAS-V 3 assembled from (NH4)2PdCl4 and poly[(N-isopropylacrylamide)5-co-diphenylphosphinostyrene] provides recycling system of itself for Mizorogi–Heck reaction. TiSS 4 made from Ti(O-i-Pr)4 and poly(styryl-linked binaphtholate-co-styrene) promotes an enantioselective carbonyl-ene reaction as a recyclable catalyst.
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Regular Articles
  • Isolation and Structure Determination of Bioactive Isoflavones from Callus Culture of Dipteryx odorata
    Ana Helena Januário, Miriam Verginia Lourenço, Lilian Ap ...
    2005 Volume 53 Issue 7 Pages 740-742
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.740
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    Crude extracts of callus and roots of Dipteryx odorata were analyzed by HPLC to detect and quantify isoflavone contents. Based on spectroscopic and X-ray crystallography data the structures of two isoflavones were elucidated as 7-hydroxy-4′,6-dimethoxyisoflavone and 3′,7-dihydroxy-4′,6-dimethoxyisoflavone. The production of dry biomass of 7-hydroxy-4′,6-dimethoxyisoflavone in cultured callus was 4.12 mg/g, approximately eleven fold higher than the amount accumulated in roots of D. odorata wild-growing plants. The 7-hydroxy-4′,6-dimethoxyisoflavone was effective against glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi. This is the first report on those bioactive isoflavones accumulated in callus of D. odorata.
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  • Synthetic Studies on d-Biotin, Part 9. An Improved Asymmetric Synthetic Route to d-Biotin via Hoffmann–Roche Lactone–Thiolactone Approach
    Fen-Er Chen, Hui-Qing Jia, Xu-Xiang Chen, Hui-Fang Dai, Bin Xie, Yun-Y ...
    2005 Volume 53 Issue 7 Pages 743-746
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.743
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    An efficient and highly stereoselective total synthesis of d-biotin has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid (2) with an overall yield of 33%. Polymer-supported oxazaborolidine-catalyzed asymmetric reduction of meso-cyclic imide 4 constitutes the key synthetic step in introducing stereogenic centers into the d-biotin molecule.
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  • Potent Inhibitory Effects of N-Aryl S-Alkylthiocarbamate Derivatives on the Dopa Oxidase Activity of Mushroom Tyrosinase
    Kun Ho Lee, Mamoru Koketsu, Sang Yoon Choi, Kang Jin Lee, Pyeongjae Le ...
    2005 Volume 53 Issue 7 Pages 747-749
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.747
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    This study reports the potent inhibitory effect of N-aryl S-alkylthiocarbamate derivatives on mushroom tyrosinase (MT) activity. N-Aryl S-alkylthiocarbamate derivatives were found to exhibit a potent inhibitory effect on the dopa (3,4-dihydroxyphenylalanine) oxidase activity of mushroom tyrosinase. Most of the N-aryl S-alkylthiocarbamate derivatives (compounds from A to J) exhibited higher inhibitory effects than kojic acid (IC50=318 μm), a well known tyrosinase inhibitor. Tyrosinase was the most inhibited by S-phenetyl N-phenylthiocarbamate (compound E, IC50=7.25 μM), and this inhibition was 44 times stronger than that of kojic acid. Compound E exhibited 95.0% of inhibition at 100 μM. A kinetic study of MT inhibition by compound E using the Lineweaver–Burk plots analysis was performed. And the kinetics profiles observed suggest that compound E competitively inhibits MT.
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  • Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents
    Chiyomi Murata, Toshinobu Masuda, Yasuko Kamochi, Kenichiro Todoroki, ...
    2005 Volume 53 Issue 7 Pages 750-758
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.750
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    To improve the fluorescence characteristics, especially emission wavelength, of coumarins, various 3-substituted-6-methoxycoumarin derivatives were synthesized, and then benzocoumarin derivatives were also synthesized in expectation of the shift to the longer wavelength region by the extension of the conjugated system. Their fluorescence properties were investigated spectrophotometrically in acetonitrile and evaluated from the viewpoint of the intramolecular charge transfer (ICT) between push- and pull-substituents in the ground and the excited states. Among them, benzocoumarin derivatives especially fluoresced in the longer wavelength around 540 nm with remarkably large Stokes shifts beyond 10000 cm−1. Using such fluorophores, some novel fluorescence derivatization reagents for carboxylic acids, alcohols, phenols, and amines were preliminarily prepared as an example, and their derivatized products were also found to fluoresce in the longer wavelength region with large Stokes shifts.
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  • Evaluation of the Compaction Properties of a Solid Dispersion of Indomethacin with Crospovidone by Tableting Process Analyzer
    Yusuke Shibata, Makiko Fujii, Hideko Okada, Shinobu Noda, Masuo Kondoh ...
    2005 Volume 53 Issue 7 Pages 759-763
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.759
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    A powder solid dispersion system (SD) of indomethacin (IM) with crospovidone (CrosPVP) possesses good fluidity and can be used for tablet formulation. Tablets of SD can be prepared by direct compression and have adequate hardness and a small variation in weight. Forces during the tableting process were measured with a tableting process analyzer (TabAll) equipped with a single-punch. The pressure transmission ratio (PTR) from the upper to the lower punch and the die wall force (DWF) were examined during the tableting process. Ejection force (EF) and scraper pressure (SP) were measured for determining the capping and sticking properties during the tableting process. Adding 1% magnesium stearate (MS) to the SD resulted in high PTR and DWF values and a low EF value. PTR and DWF values increased and EF value decreased when MS and microcrystalline cellulose (MCC) were added to the SD. A thousand tablets could be manufactured without problems such as sticking or capping when 1% MS and 50% MCC were added to the SD containing 25% IM.
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  • Preparation of Highly Potent and Selective Non-Peptide Antagonists of the Arginine Vasopressin V1A Receptor by Introduction of a 2-Ethyl-1H-1-imidazolyl Group
    Yoshiaki Shimada, Hiroaki Akane, Nobuaki Taniguchi, Akira Matsuhisa, N ...
    2005 Volume 53 Issue 7 Pages 764-769
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.764
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    To find a new series of arginine vasopressin (AVP) V1A receptor antagonists, the influence of the 2-phenyl group of 2-phenyl-4′-[(2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)carbonyl]benzanilide (7) was investigated. Replacement of the 2-phenyl group by a 2-ethyl-1H-imidazol-1-yl group was effective in yielding a V1A-selective compound. Moreover, this imidazolyl group was introduced in the same position in YM-35471 (6), and further studies of these compounds were performed. Consequently, we found that the (Z)-4′-({4,4-difluoro-5-[(N-cyclopropylcarbamoyl)methylene]-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl}carbonyl)-2-(2-ethyl-1H-1-imidazol-1-yl)benzanilide (9f) exhibited highly potent affinity and selectivity, and was the most potent antagonist for the V1A receptor among our compounds. The synthesis and pharmacological evaluation of these compounds are described in this paper
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  • Microwave Drying of Granules Containing a Moisture-Sensitive Drug: A Promising Alternative to Fluid Bed and Hot Air Oven Drying
    Sze Nam Chee, Anne Lene Johansen, Li Gu, Jan Karlsen, Paul Wan Sia Hen ...
    2005 Volume 53 Issue 7 Pages 770-775
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.770
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    The impact of microwave drying and binders (copolyvidone and povidone) on the degradation of acetylsalicylic acid (ASA) and physical properties of granules were compared with conventional drying methods. Moist granules containing ASA were prepared using a high shear granulator and dried with hot air oven, fluid bed or microwave (static or dynamic bed) dryers. Percent ASA degradation, size and size distribution, friability and flow properties of the granules were determined. Granules dried with the dynamic bed microwave dryer showed the least amount of ASA degradation, followed by fluid bed dryer, static bed microwave oven and hot air oven. The use of microwave drying with a static granular bed adversely affected ASA degradation and drying capability. Dynamic bed microwave dryer had the highest drying capability followed by fluid bed, static bed microwave dryer and conventional hot air oven. The intensity of microwave did not affect ASA degradation, size distribution, friability and flow properties of the granules. Mixing/agitating of granules during drying affected the granular physical properties studied. Copolyvidone resulted in lower amount of granular residual moisture content and ASA degradation on storage than povidone, especially for static bed microwave drying. In conclusion, microwave drying technology has been shown to be a promising alternative for drying granules containing a moisture-sensitive drug.
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  • Antimitotic and Antifungal C-3/C-3″-Biflavanones from Stellera chamaejasme
    Guohong Yang, Zhixin Liao, Zhiyong Xu, Huiping Zhang, Daofeng Chen
    2005 Volume 53 Issue 7 Pages 776-779
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.776
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    Two new C-3/C-3″ biflavanones, chamaejasmenin D (1) and isochamaejasmenin B (2), were isolated from the roots of Stellera chamaejasme, together with five known biflavanones, chamaejasmenin A (3), chamaejasmenin B (4), neochamaejasmin A (5), sikokianin A (6), and chamaejasmenin C (7). Their structures were elucidated by spectroscopic methods, including 2D NMR techniques. Among these compounds, 1—3 demonstrated potent antimitotic and antifungal activity with minimum inhibitory concentration (MIC) values of 6.25, 6.25, and 3.12 μg/ml, respectively.
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  • Selective Enhancement of Scopadulcic Acid B Production in the Cultured Tissues of Scoparia dulcis by Methyl Jasmonate
    Kasidimoko Marguerite Nkembo, Jung-Bum Lee, Toshimitsu Hayashi
    2005 Volume 53 Issue 7 Pages 780-782
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.780
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    The effects of methyl jasmonate (MeJA) on isoprenoid production were evaluated in cultured tissues of Scoparia dulcis. It was found that MeJA suppressed the accumulation of chlorophylls, carotenoids, phytol and β-sitosterol in the tissues. MeJA, however, remarkably enhanced the production of scopadulcic acid B (SDB) , with 10 μM being optimal observed concentration for stimulation of SDB production. The maximum concentration of SDB was observed 6 d after MeJA treatment.
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  • A Monoterpene Glucoside and Three Megastigmane Glycosides from Juniperus communis var. depressa
    Tsutomu Nakanishi, Naoki Iida, Yuka Inatomi, Hiroko Murata, Akira Inad ...
    2005 Volume 53 Issue 7 Pages 783-787
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.783
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    A new monoterpene glucoside (1) and three new natural megastigmane glycosides (2—4) were isolated along with a known megastigmane glucoside (5) from twigs with leaves of Juniperus communis var. depressa (Cupressaceae) collected in Oregon, U.S.A., and their structures were determined on the basis of spectral and chemical evidence. In addition, the antibacterial activities of the isolated components against Helicobacter pylori were also investigated.
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  • Constituents of Holothuroidea, 15. Isolation of Ante-iso Type Regio-isomer on Long Chain Base Moiety of Glucocerebroside from the Sea Cucumber Holothuria leucospilota
    Koji Yamada, Noriko Wada, Hiroyuki Onaka, Rei Matsubara, Ryuichi Isobe ...
    2005 Volume 53 Issue 7 Pages 788-791
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.788
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    An ante-iso type regio-isomer on the long chain base moiety of a glucocerebroside, HLC-2-A, has been isolated from its parent glucocerebroside molecular species HLC-2 composed of iso and ante-iso isomers, from the less polar lipid fraction of a chloroform/methanol extract of the sea cucumber Holothuria leucospilota. Reverse-phase HPLC that included a recycling system was effective in separating the regio-isomer from its counterpart, revealing a very close resemblance in structure. Other typical glucocerebroside molecular species HLC-1 and HLC-3 were obtained together with HLC-2. The structures of these glucocerebrosides were determined on the basis of chemical and spectroscopic evidence.
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  • Intermolecular Hydrogen Bonding of Steroid Compounds: PFG NMR Diffusion Study, Cold-Spray Ionization (CSI)-MS and X-Ray Analysis
    Kazuaki Shikii, Hiroko Seki, Shigeru Sakamoto, Yoshihisa Sei, Hiroaki ...
    2005 Volume 53 Issue 7 Pages 792-795
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.792
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    An extensive analysis of hydrogen bonding of steroid compounds in diluted solution is preformed by pulsed field gradient (PFG) NMR and cold-spray ionization (CSI)-MS, in the solid state by X-ray crystallographic analysis. The formation of hydrogen bond interaction are quantified and discussed. Although X-ray analysis in the crystalline state and CSI-MS measurement in solution suggested that the observed diffusion coefficient Dobs of the steroid compounds may vary in accordance with the number of hydrogen bonds, the actual observed Dobs value determined from the diffusion studies diminished constantly without correlation on the decreasing numbers of hydrogen bonds. Comparison of two different calibration profiles of calculated molecular volume (Vcal) vs. Dobs, which are obtained from compounds possessing no hydrogen bonding and the steroid compounds, formation of a chain structure (cluster) based on intermolecular hydrogen bonding of the steroid compounds is unambiguously confirmed.
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  • Presence of Peroxyradicals in Cigarette Smoke and the Scavenging Effect of Shikonin, a Naphthoquinone Pigment
    Masahiro Nishizawa, Masahiro Kohno, Minemitsu Nishimura, Akio Kitagawa ...
    2005 Volume 53 Issue 7 Pages 796-799
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.796
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    Using a new method having been developed for the purpose of quantitative determination for peroxyradicals, the presence of peroxyradicals was proved in cigarette smoke. In brief, peroxyradicals in cigarette smoke were measured by ESR spectrometry coupled to non-reductive scavenging of 1,1-diphenyl-2-picrylhydrazyl (DPPH). As a result, peroxyradicals were found to be major reactive oxygen species (ROS) since the concentration of peroxyradicals recovered from cigarette smoke was much higher than that of any of other ROS (superoxide and hydroxyl radical) and nitric oxide. Furthermore, several antioxidants (ascorbic acid, reduced glutathione, epigallocatechin gallate, shikonin) were examined for scavenging activity against peroxyradicals in the cigarette smoke. Among them shikonin alone exerted the scavenging activity, suggesting that shikonin is promising antioxidant for cigarette filters because of its effectiveness against broad range of ROS including peroxyradicals, heat resistance, nonvolatility and high affinity to the filter.
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  • Staphylionosides A—K: Megastigmane Glucosides from the Leaves of Staphylea bumalda DC.
    Qian Yu, Katsuyoshi Matsunami, Hideaki Otsuka, Yoshio Takeda
    2005 Volume 53 Issue 7 Pages 800-807
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.800
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    Chemical investigation of leaves of Staphylea bumalda DC., collected in the suburbs of Hiroshima City, afforded 11 new megastigmane glucosides, named staphylionosides A—K (3—13), along with two known megastigmane glucosides (1, 2). The relative structures were elucidated from spectroscopic evidence, and the absolute structures of the aglycones were determined by means of the combination of β-D-glucosylation-induced shift-trends and the modified Mosher's method.
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  • New Bicyclic Taxane Diterpenoids from Taxus sumatrana
    Ya-Ching Shen, Shaw-Man Hsu, Yun-Sheng Lin, Kuen-Ching Cheng, Ching-Te ...
    2005 Volume 53 Issue 7 Pages 808-810
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.808
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    Investigation of an acetone extract of the leaves and twigs of Taxus sumatrana has resulted in the isolation of two new bicyclic taxoids, tasumatrols M (1), and N (2) and a new baccatin III derivative, tasumatrol O (3) together with the previous known 7-deacetylcanadensene (4) and 2α,7β,13α-triacetoxy-5α,9α-dihydroxy-2(3→20) abeotaxa-4(20),11-dien-10-one. The structures of these taxanes were established on the basis of spectroscopic analyses, especially 1- and 2D NMR, and chemical derivatization.
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  • Evaluation of Titanium Dioxide as a Pharmaceutical Excipient for Preformulation of a Photo-Labile Drug: Effect of Physicochemical Properties on the Photostability of Solid-State Nisoldipine
    Koichi Kakinoki, Kenji Yamane, Miho Igarashi, Manami Yamamoto, Reiko T ...
    2005 Volume 53 Issue 7 Pages 811-815
    Published: 2005
    Released on J-STAGE: July 01, 2005
    DOIhttps://doi.org/10.1248/cpb.53.811
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    To characterize the photocatalytic activity of TiO2 via solid-state reaction, the relationship between the physicochemical properties and photocatalytic activity of TiO2 was investigated and estimated from the results of photodegradation of nisoldipine. The photodegradation of nisoldipine was significantly enhanced by addition of TiO2. Two degradation products, nitroso-phenylpyridine derivative and nitro-phenylpyridine derivative, were formed. The degree of photocatalytic activity of TiO2 was quite different between the various types of TiO2 investigated, even when the crystalline phase was the same. As a result of the investigations into the relationship between the photocatalytic activity and physicochemical properties of TiO2, it was found that for the rutile form the photocatalytic activity has good correlation with specific surface area of TiO2, but poor correlation with water loss on drying of TiO2. However, for the anatase form, the photocatalytic activity has good correlation with water loss on drying of TiO2, but poor correlation with specific surface area. Moreover, it was found that the crystallinity of TiO2 has a moderate correlation with the photocatalytic activity of both crystal forms of TiO2. These results suggest that a degree of photocatalytic activity of TiO2 depends on the various physicochemical properties of each type of TiO2 investigated.
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Communications to the Editor
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