Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 52, Issue 4
Displaying 1-31 of 31 articles from this issue
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Regular Articles
  • New C19-Diterpenoid Alkaloids from Delphinium trifoliolatum
    Xian-Li Zhou, Qiao-Hong Chen, Feng-Peng Wang
    2004 Volume 52 Issue 4 Pages 381-383
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.381
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    Three new norditerpenoid alkaloids, trifoliolasines A (1), B (3), and C (5), were isolated from the whole plant of Delphinium trifoliolatum FINET et GAGNEP, and their structures were established based on the spectral data.
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  • Pre-formulation Studies on Moisture Absorption in Microcrystalline Cellulose Using Differential Thermo-Gravimetric Analysis
    Paul Wan Sia Heng, Celine Valeria Liew, Josephine Lay Peng Soh
    2004 Volume 52 Issue 4 Pages 384-390
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.384
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    A study on the differential thermo-gravimetric (DTG) measurements of microcrystalline cellulose (MCC) containing moisture indicated that particle size affected the amount of bound water and the flow indices. Thermal analysis of 6 commercial grades of MCC powders and MCC/water blends were performed using a thermo-gravimetric analyzer. These MCCs were differentiated by their particle size, bulk and tapped densities, crystallinity and micromeritic properties. From the DTG curves, it was observed that water loss from the MCC/water blends occurred in 3 phases which corresponded to the different states of water associated with the solid particles. Area under the third phase, or the falling rate phase, can be associated with the release of water that was physically shielded or bound to the solid. This water may be referred to as “structured” water. The large particle size grades of MCC-Avicel PH 102, PH 302 and Pharmacel 102 were found to possess smaller quantities of structured water. Water vapor sorption results revealed the monolayer capacities for the respective MCC grades. The amount of structured water appeared to correspond to the existence of bilayers on the surface of the small particle size MCC grades. Using the avalanche flow assessment method, flow properties of small particle size grades of MCC were found to be poorer as indicated by the significant correlation between their flow indices and size, in addition to the longer mean times to avalanche.
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  • Anthrone C-Glucosides from Rheum emodi
    Liselotte Krenn, Riddhi Pradhan, Armin Presser, Gottfried Reznicek, Br ...
    2004 Volume 52 Issue 4 Pages 391-393
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.391
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    In a study of the anthraderivatives in roots of Rheum emodi, three new anthrone C-glucosides, named 10-hydroxycascaroside C (1), 10-hydroxycascaroside D (2) and 10R-chrysaloin 1-O-β-D-glucopyranoside (3) were isolated besides the rare compounds cascaroside C (4), cascaroside D (5) and cassialoin (6). Additionally the investigation resulted in the isolation of an acetylated chrysophanol glucoside, 8-O-β-D-(6′-O-acetyl)glucopyranosyl-chrysophanol (7). The structures were established by comprehensive spectroscopic investigations.
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  • Transport of Harman Alkaloids across Caco-2 Cell Monolayers
    Shabana Iqrar Khan, Ehab Ahmed Abourashed, Ikhlas Ahmad Khan, Larry An ...
    2004 Volume 52 Issue 4 Pages 394-397
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.394
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    This study examined the intestinal transport of five harman alkaloids using the Caco-2 cell monolayer as a model of the human intestinal mucosa. Transport parameters, permeability coefficients and percent transports, were calculated and compared under identical conditions with atenolol. Permeability coefficients were also compared with the reported values for model compounds like mannitol, propranolol and glucose. Sodium fluorescein was used as the marker for paracellular leakage. These alkaloids, in the concentration range of 250—500 μM, demonstrated substantial transport across the monolayer with moderate to high efflux rates and permeability coefficients. The transport was linear with time and was concentration dependent.
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  • A Comparison of Drug Loading Capacity of Cellactose with Two ad hoc Processed Lactose–Cellulose Direct Compression Excipients
    Marta Casalderrey, Consuelo Souto, Angel Concheiro, José Luis G ...
    2004 Volume 52 Issue 4 Pages 398-401
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.398
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    This study compares the drug loading capacity of Cellactose and two excipients of similar composition and similar particle size, prepared by dry granulation and extrusion-spheronization respectively. The drugs evaluated were acetaminophen and furosemide. Acetaminophen did not significantly affect the flow properties of any of the excipients, whereas furosemide markedly worsened flow properties, eliminating the differences initially existing among the three excipients. For both drugs, tablet mechanical properties were clearly better with Cellactose than with the other excipients. Acetaminophen dissolution rate was very similar regardless of the excipient used, but furosemide dissolution rate was lower from Cellactose tablets than from tablets prepared with the other excipients. This important difference is discussed in terms of micropore structure, specific surface area, and wettability of tablets, and is attributable to the special structure of Cellactose particles.
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  • Chromanones and Dihydrocoumarins from Calophyllum blancoi
    Ya-Ching Shen, Li-Tang Wang, Ashraf Taha Khalil, Yao-Haur Kuo
    2004 Volume 52 Issue 4 Pages 402-405
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.402
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    Chromatographic fractionation of the acetone extract of the seeds of Calophyllum blancoi yielded six pyranochromanone derivatives; apetalic acid (1), isoapetalic acid (2), apetalic acid methyl ester (3), apetalic acid 5-O-acetate (4), isoapetalic methyl ester (5), and isoapetalic acid 5-O-acetate (6). In addition, one new dihydrocoumarin derivative, isorecedensolide (7), was also isolated together with recedensolide (8). The structures of the isolated compounds were established through analysis of NMR spectral data including 2D techniques as well as other physical and spectroscopic methods. Compounds 3, 4, 5, 7, and 8 showed mild activity against KB (human oral epidermoid carcinoma) and Hela (human cervical epitheloid carcinoma) tumor cell lines.
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  • Synthesis and Evaluation of 1-Arylsulfonyl-3-piperazinone Derivatives as Factor Xa Inhibitors IV.
    A Series of New Derivatives Containing a Spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4′-piperidin]-5-one Skeleton
    Hidemitsu Nishida, Takafumi Mukaihira, Fumihiko Saitoh, Kousuke Harada ...
    2004 Volume 52 Issue 4 Pages 406-412
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.406
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    In the course of development of factor Xa (FXa) inhibitor in an investigation involving the synthesis of 1-arylsulfonyl-3-piperazinone derivatives, we found new compounds containing a unique spiro skeleton. Among such compounds, (−)-7-[(6-chloro-2-naphthalenyl)sulfonyl]tetrahydro-8a-(methoxymethyl)-1′-(4-pyridinyl)-spiro[5H-oxazolo[3,2-a]pyrazine-2(3H),4′-piperidin]-5-one (28, M55529) had activity more favorable than those of previously reported compounds. The inhibitory activity of M55529 for FXa is IC50=2 nM, with high selectivity for FXa over thrombin and trypsin.
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  • Studies on Tellurium-Containing Heterocycles. Part 22.
    Tellurazepine Ring System: Preparation of 1,5-Benzotellurazepin-4-ones and Their Conversion into Fully Unsaturated 1,5-Benzotellurazepines
    Haruki Sashida, Hirohito Satoh
    2004 Volume 52 Issue 4 Pages 413-417
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.413
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    The treatment of o-iodopropiolanilides (12), which were easily prepared from o-iodophenylisocyanate (11) and ethynylmagnesium bromide, with sodium hydrogen telluride resulted in the intramolecular ring closure of the presumed phenyltellurol intermediates (13) to a triple bond to give the 1,5-benzotellurazepin-4-ones (14) as the sole characterized products. The obtained amides (14) were easily converted into fully unsaturated lactim 4-methoxy-1,5-benzotellurazepines (18) by treatment with trimethyloxonium tetrafluoroborate. Decomposition by thermolysis of the 4-methoxyazepinenes (18) afforded the 4-methoxyquinolines (19) with extrusion of a tellurium atom.
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  • Synthesis of Panax Acetylenes: Chiral Syntheses of Acetylpanaxydol, PQ-3 and Panaxydiol
    Mitsuru Satoh, Mitsuo Watanabe, Masatoshi Kawahata, Kunihiko Mohri, Yu ...
    2004 Volume 52 Issue 4 Pages 418-421
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.418
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    Acetylpanaxydol (1-Ac), PQ-3 (2) and panaxydiol (3) and their optical isomers were synthesized from L-(+)-diethyl tartrate. The absolute configurations of 1-Ac, 2 and 3 were determined to be 1-Ac (3R,9R,10S), 2 (9R,10S) and 3 (3R,10S), respectively, by comparisons of their optical rotations and the NMR data of their MTPA esters with those of natural products.
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  • Peptide Synthesis in Water IV.
    Preparation of N-Ethanesulfonylethoxycarbonyl (Esc) Amino Acids and Their Application to Solid Phase Peptide Synthesis
    Keiko Hojo, Mitsuko Maeda, Timothy J. Smith, Eriko Kita, Fumie Yamaguc ...
    2004 Volume 52 Issue 4 Pages 422-427
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.422
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    A new N-protecting group, ethanesulfonylethoxycarbonyl (Esc), was designed to perform peptide synthesis in both aqueous and organic solvents. Esc-amino acids were prepared by the reaction of Esc-Cl and amino acids. Although Esc-Cl was a highly reactive reagent, it was not stable and decomposed during the purification procedure. A more stable reagent, ethanesulfonylethyl-4-nitrophenyl carbonate (Esc-ONp), was designed for preparation of Esc-amino acids. Esc-ONp was a stable reagent and could be purified by silica gel column chromatography or recrystallization. Esc-amino acids were prepared by the reaction of Esc-ONp and amino acids in good yield. To evaluate Esc-amino acids, Leu-enkephalin amide was synthesized using Esc-amino acids by the solid phase method in water. Removal of the Esc group was performed with 0.025 mol/l NaOH in 50% aqueous ethanol. Leu-enkephalin amide was successfully synthesized on a poly(ethylene glycol)-grafted polystyrene resin. Esc-amino acids have moderate solubility in organic solvents (such as dimethylformamide and acetonitrile). Leu-enkephalin amide was synthesized using Esc-amino acids by the solid phase method in dimethylformamide. Removal of the Esc group was performed with 0.05 mol/l tetrabutylammonium fluoride in dimethylformamide. Synthesis of Leu-enkephalin amide using Esc-amino acids in dimethylformamide was also successful. The yields of synthesis of Leu-enkephalin amide in water and dimethylformamide were 71% and 67%, respectively.
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  • Insulin-Mimetic Vanadyl(IV) Complexes as Evaluated by Both Glucose-Uptake and Inhibition of Free Fatty Acids (FFA)-Release in Isolated Rat Adipocytes
    Yusuke Adachi, Hiromu Sakurai
    2004 Volume 52 Issue 4 Pages 428-433
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.428
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    We have recently proposed the existence of some potent vanadyl complexes with blood glucose-lowering activity in experimental diabetic animals based on the results of an in vitro FFA (free fatty acids)-release assay in isolated rat adipocytes treated with epinephrine and evidence of an in vivo blood glucose lowering effect in experimental diabetic animals. However, the FFA assay depends indirectly on the glucose-uptake of vanadyl complexes in adipocytes. It is therefore necessary to develop a more reliable in vitro glucose-uptake assay, in place of the glucose uptake method using radioactive compounds such as 14C-glucose, to identify insulin-mimetic vanadyl complexes. In the present study, we proposed a combined in vitro assay by using the conventional glucose oxidase method for glucose-uptake and FFA assay in isolated rat adipocytes. Insulin, vanadyl sulfate (VOSO4), bis(picolinato)vanadyl (VO(pa)2), and bis(6-methylpicolinato)vanadyl (VO(6mpa)2) complexes exhibited concentration-dependent uptake of (+)-D-glucose and inhibition of FFA release in the adipocytes treated with epinephrine. Vanadyl complexes were found to accelerate glucose-uptake at lower concentrations than VOSO4. In vitro high insulin-mimetic activity of VO(pa)2 and VO(6mpa)2 were thus indicated by both glucose-uptake and FFA-release, with the insulin-mimetic activity of VO(6mpa)2 being higher than that of VO(pa)2, as suggested by the partition coefficient (0.330 for VO(pa)2 and 0.595 for VO(6mpa)2). The proposed assay provides a more reliable method than each single method for the evaluation of in vitro insulin-mimetic activity of compounds.
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  • Kinetic Comparisons of Anthocyanin Reactivities towards 2,2′-Azobis(2-amidinopropane) (AAPH) Radicals, Hydrogen Peroxide and tert-Buthylhydroperoxide by Capillary Zone Electrophoresis
    Takashi Ichiyanagi, Yoshihiko Hatano, Seiichi Matsugo, Tetsuya Konishi
    2004 Volume 52 Issue 4 Pages 434-438
    Published: 2004
    Released on J-STAGE: April 01, 2004
    DOIhttps://doi.org/10.1248/cpb.52.434
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    Twelve major anthocyanins identified in bilberry extracts were studied in vitro using capillary zone electrophoresis (CZE) for their reactions towards 2,2′-azobis(2-amidinopropane) (AAPH) radicals, hydrogen peroxides (H2O2) and tert-buthylhydroperoxides (t-BuOOH). Reactivity towards AAPH radicals was primarily determined by the aglycon structure, not by the type of sugar moiety. Delphinidins carrying three-hydroxyl groups on the B ring were most reactive followed by cyanidins, with two-hydroxyl groups. Further, methylation of the hydroxyl groups reduced reactivity towards AAPH radicals. However, reactivity of anthocyanins towards H2O2 was not significantly affected by aglycon structure or by the type of sugar moiety; there being no marked difference in reaction rates among the anthocyanins. Reactivity towards t-BuOOH was essentially the same as towards H2O2, although the reaction rate was several times smaller. Also, the reaction rate of anthocyanin towards peroxide was relatively high compared to that of (+)-catechin (approximately 30 times larger) measured as a reference antioxidant, whereas the reactivities of anthocyanins and (+)-catechin towards AAPH radicals were similar.
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Notes
Communications to the Editor
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