Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 50, Issue 9
Displaying 1-35 of 35 articles from this issue
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Regular Articles
  • Physical Properties of Phosphatidylcholine Vesicles Containing Small Amount of Sodium Cholate and Consideration on the Initial Stage of Vesicle Solubilization
    Changqi Sun, Hiroshi Kashiwagi, Masaharu Ueno
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1145-1150
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1145
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    The effects of sub-solubilizing concentrations of sodium cholate (Na-chol) on several physicochemical properties of phosphatidylcholine (PC) small unilamellar vesicles (SUV) were considered in connection with the initial stage of membrane solubilization. ESR spectra of 12-doxylstearic acid (12-DS) in phosphatidylcholine from egg yolk (EPC) or dimyristoylphosphatidylcholine (DMPC) SUV at low concentrations (insufficient to destroy the vesicles) of Na-chol were composed of two (a strongly immobilized and an additional weakly immobilized) immiscible components. The origin of the additional bands was phase separation which occurred in the hydrophobic parts of PC SUV in the presence of Na-chol. Differential scanning calorimetry measurements demonstrated that the mixed DMPC/Na-chol SUV possessed two (a sharp low-temperature and a broad high-temperature) endothermic peaks, which is consistent with the coexistence of two immiscible phases in the vesicular membranes. ζ Potentials of the EPC/Na-chol SUV revealed that high anionic densities appeared on the surfaces of the SUV at a Na-chol concentration slightly below the upper boundary of the vesicle region. Thus, the initial stage of the solubilization of PC SUV by Na-chol was caused by the aggregation of hydrophobic parts of PC membranes, followed by the occurrence of high anionic densities on the surfaces of the vesicles. The fact that removal of Na-chol from PC/Na-chol mixed systems preferentially resulted in the formation of small vesicles might originate from these anionic charges.
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  • Pharmacological Studies and Synthesis of Morpholino Alkyl Derivatives
    Carmela Saturnino, Anna Capasso, Jean-Chanles Lancelot, Sylvain Rault, ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1151-1154
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1151
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    Seven morpholin derivatives were synthesized (compounds 1—7) and their behavioural effects were evaluated; the elements considered were locomotor activity, motor coordination, catalepsy, stereotyped behaviour and antinociception. All the compounds, at doses of 10—20—40 mg/kg/i.p., induced a reduction of all behavioural elements without a significant antinociceptive effect. These results indicate that these morpholin derivatives affect the central nervous system.
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  • Influence of Physical Parameters and Lubricants on the Compaction Properties of Granulated and Non-granulated Cross-linked High Amylose Starch
    Miloud Rahmouni, Vincent Lenaerts, Danielle Massuelle, Eric Doelker, a ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1155-1162
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1155
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    Cross-linked high amylose starch (CLA) is a pharmaceutical excipient used in direct compression for the preparation of controlled release tablets and implants. In this work the compression properties of CLA in bulk and granulated forms (without binder) were evaluated for the first time. Tablets were prepared on an instrumented single punch machine. The flow properties and the compression characteristics (compressibility, densification behavior, work of compression) of the materials as well as the mechanical strength of the finished compacts (compactibility) were systematically examined. Wet granulation was found to improve the flowability and the compressibility of CLA but concomitantly reduced its compactibility. It was demonstrated that CLA was a plastically deforming material with a plasticity index and a yield pressure value comparable to those of pregelatinized starch. The compactibility of granulated CLA was independent of particle size in the range of 75 to 500 μm, but slightly decreased when the percentage of the fine particles (<75 μm) in the bulk powder was increased. Water and colloidal silicone dioxide facilitated the consolidation of CLA, while magnesium stearate had an opposite effect on the tablet crushing force.
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  • Synthesis and Cyclic AMP Phosphodiesterase 4 Isoenzyme Inhibitory Activity of Heterocycle Condensed Purines
    Hirokazu Suzuki, Manabu Yamamoto, Susumu Shimura, Ken-ichi Miyamoto, K ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1163-1168
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1163
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    To reverse the adverse reactions of alkylxanthines and to develop novel inhibitors of cyclic AMP phosphodiesterase 4 (PDE4), a series of heterocycle [a]-, [b]-, [c,d]-, and [i]-condensed purines were designed and synthesized. Although all compounds did not display PDE1 and PDE3 inhibitory activities, several heterocycle [i]-condensed purines strongly inhibited PDE4. Especially, dl-3,4-dipropyl-8-methyl-4,5,7,8-tetrahydro-1H-imidazo[2,1-i]purin-5-one (dl-7c) exhibited comparable PDE4 inhibitory activity (IC50=1.9 μM) to rolipram and denbufylline (DBF).
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  • Design of Controlled Release System with Multi-layers of Powder
    Norihito Shimono, Masumi Ueda, Yasuhiko Nakamura
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1169-1175
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1169
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    Pellets containing active ingredients were coated with water-insoluble powders, i.e. hydrogenated caster oil (Lubliwax (WAX)) and magnesium stearate (Mg-St). The influences of the structural difference of the sustained release layer and curing conditions on the drug release rate were investigated. Sodium valproate (VP-Na) was used as a highly water-soluble model drug. Drug release profiles were influenced by the combination of the WAX layer and the Mg-St layer. Even if the formula of sustained release layers were the same, drug release rate could be affected by the structural difference of the controlled release layer. The Mg-St layer was more effective in prolonging drug release than the WAX layer. Compared with single and double layer types, the triple layer (sandwich) type was most effective in obtaining a long sustained drug release. Heat-treatment retarded drug release mainly by increasing the density of the sustained release layer of the WAX. The Mg-St was effective in protecting the agglomeration between particles during heat-treatment. Optimal heat-treatment conditions were found to exist. Scanning electron microscopy (SEM) analysis indicated that heat-treatment caused the WAX to melt, formed a film-like structure and made the release layer dense. Furthermore, heat-treatment changed the release pattern of VP-Na from sustained release pellets with a multi-layer of powder, leading to zero-order release.
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  • Mass Variation Tests for Coating Tablets and Hard Capsules: Rational Application of Mass Variation Tests
    Noriko Katori, Nobuo Aoyagi, Shigeo Kojima
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1176-1180
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1176
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    The mass variation test is a simplified alternative test version of the content uniformity test. In the case of coating tablets and capsules, the mass variation test is principally applied to test the inner cores or fillings containing the active ingredient. However, some exceptions exist in pharmacopoeias. The effects of tablet coating and capsule shell on the results of the mass variation test were studied. The mass variation of outer crusts (coatings, capsule shells) and inner cores (core tablets, fillings) was measured separately in several products. The effects of coating on weight variability were very large for sugar-coated tablets. Relative standard deviation (RSD) of the formulation weight (RSDW) of sugar-coated tablets (2.73%) was larger than that of plain tablets (0.77%). The cause of the large RSDW is the large variation the weight of sugar-coating accounting for 44% of formulation weight. In the case of film-coated tablets, the effect of coating weight on the mass variation test was very small because the rate of coating in comparison to the whole weight was small. In the case of hard capsules, the usage of whole formulation weight resulted in underestimation of variations of filling weight. The differences between dosage forms in the applicability of the mass variation test are caused by differing weight proportions and variability of the outer coatings or shells. To avoid the underestimation of mass variation for hard capsules, a corrected acceptance value is useful. For all the dosage units, the mass variation test can principally be applied to determine which mass is expected to be proportional to the content of the active ingredient. However, some modification of acceptance values enables application of the mass variation tests to inapplicable cases, such as when the RSD of drug concentration (RSDC) is larger than 2%.
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  • Evaluation of the Disintegration Time of Rapidly Disintegrating Tablets via a Novel Method Utilizing a CCD Camera
    Yutaka Morita, Yuki Tsushima, Masanobu Yasui, Ryoji Termoz, Junko Ajio ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1181-1186
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1181
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    Many kinds of rapidly disintegrating or oral disintegrating tablets (RDT) have been developed to improve the ease of tablet administration, especially for elderly and pediatric patients. In these cases, knowledge regarding disintegration behavior appears important with respect to the development of such a novel tablet. Ordinary disintegration testing, such as the Japanese Pharmacopoeia (JP) method, faces limitations with respect to the evaluation of rapid disintegration due to strong agitation. Therefore, we have developed a novel apparatus and method to determine the dissolution of the RDT. The novel device consists of a disintegrating bath and CCD camera interfaced with a personal computer equipped with motion capture and image analysis software. A newly developed RDT containing various types of binder was evaluated with this protocol. In this method, disintegration occurs in a mildly agitated medium, which allows differentiation of minor distinctions among RDTs of different formulations. Simultaneously, we were also able to detect qualitative information, i.e., morphological changes in the tablet during disintegration. This method is useful for the evaluation of the disintegration of RDT during pharmaceutical development, and also for quality control during production.
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  • Synthesis and Evaluation of 1-Arylsulfonyl-3-piperazinone Derivatives as a Factor Xa Inhibitor II. Substituent Effect on Biological Activities
    Hidemitsu Nishida, Yutaka Miyazaki, Takafumi Mukaihira, Fumihiko Saito ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1187-1194
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1187
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    Intravascular clot formation is an important event in a number of cardiovascular diseases. The prevention of blood coagulation has become a major target for new therapeutic agents. Factor Xa (FXa) is a trypsin-like serine protease that plays a key role in the blood coagulation cascade and represents an attractive target for anticoagulant drug development. We have investigated substituents in the central part of a lead compound (3: M55113), and discovered that compound M55551 (34: (R)-4-[(6-Chloro-2-naphthalenyl)sulfonyl]-6-oxo-1-[[1-(4-pyridinyl)-4-piperidinyl]methyl]-2-piperazinecarboxylic acid) is a potent inhibitor of FXa (IC50=0.006 μM), with high selectivity for FXa over trypsin and thrombin. The activity of this compound is ten times more powerful than the lead compound.
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  • Sesquiterpenes and Alkaloids from Lindera chunii and Their Inhibitory Activities against HIV-1 Integrase
    Chao-feng Zhang, Norio Nakamura, Supinya Tewtrakul, Masao Hattori, Qi- ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1195-1200
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1195
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    Three new eudesmane type sesquiterpenoid lindenanolides E (1), F (2) and G (3), and two new aporphine alkaloid lindechunines A (18) and B (20) were isolated from roots of Lindera chunii MERR., together with seven known sesquiterpenes including a new naturally-occurring lindenanolide H (4) and eight known aporphine alkaloids. The structures of these compounds were determined by spectroscopic means. Of the isolated compounds, hernandonine (14), laurolistine (16), 7-oxohernangerine (17) and lindechunine A (18) showed significant anti-human immunodeficiency virus type 1 (HIV-1) integrase activity with IC50 values of 16.3, 7.7, 18.2 and 21.1 μM, respectively. The major alkaloids presented in the roots of L. chunii were quantitatively analyzed by an HPLC method.
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  • Gentamicin Sulphate Release from a Modified Commercial Acrylic Surgical Radiopaque Bone Cement. I. Influence of the Gentamicin Concentration on the Release Process Mechanism
    Eva Díez-Peña, Gloria Frutos, Paloma Frutos, José ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1201-1208
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1201
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    The purpose of the present work was the study of the gentamicin sulphate (GS) release from a commercial acrylic bone cement CMW-1® with the aims of establishing the influence of the slabs preparation as well as the release mechanism and kinetics. The effect of the amount of GS on the release kinetic parameters has been also investigated. In vitro release studies were performed in a buffered saline solution at pH 7.4 and 37 °C. The GS concentration was determined using an indirect spectrophotometric method with an o-phthaldialdehyde as a derivatizing reagent. A commercial and three modified samples were tested. The free and fractured surfaces of the GS cement slabs before and after the release studies were observed by means of scanning electron microscopy (SEM). For low GS concentration loading the release was very incomplete because most of the GS beads were encapsulated by the hydrophobic PMMA matrix. A higher amount of antibiotic was released from cement that has a higher amount incorporated. A model and therefore a mechanism of release based on this model have been proposed. It has allowed us to explain the changes in dissolution kinetics of an acrylic matrix type controlled release system up to 12% GS loading. The cumulative amount of GS released Mt/Mi, was fitted as a function of time. For lower amounts of GS, the regression analysis (R2>0.99) revealed that the release is most adequately represented by Mt/Mi=b+ktn, where b represents a burst effect. The goodness of fit decreases as the amount of GS increases. The influence of some other type of release mechanism for higher amounts of GS must be taken into account and a second model for the release, Mt/Mi=b+k·[1−exp(−kt)], is proposed.
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  • Dynamic Characteristics of a Peptide-Binding Groove of Human HLA-A2 Class I MHC Molecules: Normal Mode Analysis of the Antigen Peptide–Class I MHC Complex
    Hiroyuki Nojima, Mayuko Takeda-Shitaka, Youji Kurihara, Masaaki Adachi ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1209-1214
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1209
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    Class I major histocompatibility complex (MHC) binds antigen peptides with various sequences. We performed a normal mode analysis of HLA-A2 MHC that binds three peptides with different affinity. HLA-A2 MHC has a peptide-binding groove composed of two α-helices (residue 49—84, residue 140—179). Some residues in the center of the groove showed an increase in fluctuations and some residue pairs between two helix groups showed a negative change in correlations by removing the antigen peptide. The extent of the fluctuation and correlation changes correlated well with the experimental ranking of the three peptides in binding affinity. Some definite anti-correlative motions were found between two helix groups in low frequency modes (<50 cm−1) by removing the antigen peptide. We propose that the above anti-correlative motions play an important role to bind the antigen peptide, especially in obtaining a “dynamic fit.”
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  • Studies on Quinones. Part 37. Synthesis and Biological Activity of o-Aminoester Functionalised Benzo- and Naphtho[2,3-b]thiophenequinones
    Jaime A. Valderrama, Claudio Astudillo, Ricardo A. Tapia, Eric Prina, ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1215-1218
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1215
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    The synthesis of 3-amino-2-methoxycarbonyl-4,7-dimethoxybenzo[b]thiophene (5) and benzothieno[3,2-d][1,3]oxazin 15 from 3,6-dimethoxy-2-nitrobenzaldehyde (1) is reported. Benzo[b]thiophene-4,7-quinones 9 and 10 were prepared in good yields by oxidative deprotection of the corresponding dimethoxybenzothiophenes 8 and 7. Cycloaddition reaction of quinone 8 with 1-(E)-trimethylsilyloxy-1,3-butadiene followed by acid-induced aromatization provides access to naphtho[2,3-b]thiophene-4,9-quinone 13 and 14. The in vitro activity of the new quinones against Leishmania amazonensis and human-T-cell leukemia virus type 1 (HTLV-1) is reported.
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  • Release from or through a Wax Matrix System. IV. Generalized Expression of the Release Process for a Reservoir Device Tablet
    Yorinobu Yonezawa, Sumio Ishida, Shinobu Suzuki, Hisakazu Sunada
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1219-1222
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1219
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    Generalization of the release process through the wax matrix layer was examined by use of a reservoir device tablet. The wax matrix layer of the reservoir device tablet was prepared from a physical mixture of lactose and hydrogenated castor oil to simplify the release properties. Release through the wax matrix layer showed zero-order kinetics in a steady state after a given lag time, and could be divided into two stages. The first stage was the formation process of water channel by dissolving the soluble component in the wax matrix layer. The lag time obtained by applying the square root law equation was well connected with the amount of the matrix layer and mixed weight ratio of components in this layer. The second stage was the zero-order release process of drug in the reservoir through the wax matrix layer, because the effective surface area was fixed. The release rate constants were connected with thickness of the matrix layer and permeability coefficient, and the permeability coefficients were connected with the diffusion coefficient of drug and porosity. Hence the release rate constant could be connected with the amount of matrix layer and the mixed weight ratio of components in the matrix layer. It was therefore suggested that the release process could be generalized using the amount of matrix layer and the mixed weight ratio of components in the matrix layer.
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  • Synthesis of N-Substituted Piperazinyl Carbamoyl and Acetyl Derivatives of Tetrahydropapaverine: Potent Antispasmodic Agents
    Jaskiran Kaur, Narendra Nath Ghosh, Anita Talwar, Ramesh Chandra
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1223-1228
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1223
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    The synthesis and structure–activity-relationship (SAR) for a series of N-substituted piperazinyl carbamoyl 7—15 and piperazinyl acetyl 18—26 derivatives of tetrahydropapaverine have been carried out. The general synthetic methods of carbamoyl tetrahydropapaverine analogues involve N-substituted piperazines and carbamoyl imidazole tetrahydropapaverine as starting materials. Another route for synthesizing these compounds, involving the formation of carbamoyl imidazole piperazine has also been explored. Acylation of tetrahydropapaverine followed by substitution with various piperazinyl moities afforded the acetyl tetrahydropapaverine derivatives. Variously substituted piperazines have been used to monitor the effect of electron releasing and electron withdrawing substituents upon the antispasmodic activity of the molecules. Effect of varying electron densities on the antispasmodic activity, by altering the position of these groups on the benzene ring has also been monitored. Pharmacological methods involve the in vitro antispasmodic activity studies on a freshly removed guinea pig ileum using a force displacement transducer amplifier connected to a physiograph. Among the analogues synthesized in the present study, a promising compound 7, a potent muscle relaxant as compared to papaverine has been obtained.
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  • Preparation and Biological Activities of a Bivalent Poly(Ethylene Glycol) Hybrid Containing an Active Site and Its Synergistic Site of Fibronectin
    Yuichi Susuki, Keiko Hojo, Ikuko Okazaki, Haruhiko Kamata, Masahiko Sa ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1229-1232
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1229
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    A bivalent poly(ethylene glycol) or PEG hybrid of fibronectin-related peptides was prepared. An active site peptide (RGD) and its synergistic site peptide (PHSRN) of fibronectin were conjugated with an amino acid-type PEG (aaPEG) to form PHSRN–aaPEG–RGD. A moderate spatial array between RGD and PHSRN in fibronectin may be required for synergic activity. The bivalent hybrid exhibited potent cell spreading activity and exhibited potent anti-metastatic activity in a model of experimental metastasis with B16–BL6 cells in mice. PEG may serve as a spacer for maintaining the desired spatial array.
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  • Development of a Simple HPLC Method for Determination of Paeoniflorin-Metabolizing Activity of Intestinal Bacteria in Rat Feces
    Ju-Xiu He, Teruaki Akao, Tadato Tani
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1233-1237
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1233
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    A simple and reproducible HPLC method for the determination of paeoniflorin (PF)-metabolizing activity of intestinal bacteria in rat feces was developed and validated. Orally administered PF, a major active constituent of Paeoniae Radix, is metabolized into a bioactive compound, paeonimetabolin I (PM-I) by intestinal bacteria. Direct determination of the PF-metabolizing rate into PM-I is hard to achieve by HPLC due to the lack of intense chromophore in PM-I. However, when PF was incubated with Lactobacillus brevis, an intestinal bacterium, in the presence of phenylmercaptan, the metabolizing rate of PF into 8-phenylthio-paeonimetabolin I (PT-PM-I) was found to be equivalent to that of PF into PM-I. Thus, the PF-metabolizing activity of intestinal bacteria in rat feces was determined by measuring the rate of biotransformation of PF into PT-PM-I, which was detected by HPLC at 255 nm. This method can be utilized in the biopharmaceutical study of traditional Chinese formulations containing Paeoniae Radix.
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  • Physicochemical Properties of PEG-Grafted Liposomes
    Supaporn Sriwongsitanont, Masaharu Ueno
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1238-1244
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1238
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    Egg phosphatidylcholine (EggPC) or dimyristoylphosphatidylcholine (DMPC) liposomes containing polyethylene glycol (PEG)-lipids covering a range of 0—30 mol% have been prepared by Extrusion method. The physicochemical properties including size evolution and calcein permeation were evaluated to investigate the effect of PEG-lipids on bilayer structure. The results from quasielasetic light scattering (QELS), freeze-fracture microscopy, and gel exclusion chromatography revealed that presence of low concentration of PEG-lipid results in decreasing of vesicle size and further increase in the PEG-lipid concentrations lead to a transition from the lamellar membranes to micelles. The permeability for calcein increased with increase in concentration of distearoylphosphatidylethanolamine (DSPE)-PEG. On the other hand, the permeability decreased with low amount of cholesterol-PEG (blow 20% cholesterol-PEG) and increased with high amount of it. The maximum concentration of PEG-lipid that may be incorporated without alteration of the liposome structure depends on the composition of the bilayer. The concentration of DSPE-PEG2000 incorporated into vesicles without damaging vesicle structures were <20 mol% for EggPC and <10% for DMPC.
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  • Eucosterol Oligoglycosides Isolated from Scilla scilloides and Their Anti-tumor Activity
    Sang-Myung Lee, Hyo-Kon Chun, Choong-Hwan Lee, Byung-Sun Min, Eun-Sook ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1245-1249
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1245
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    Two new eucosterol oligoglycosides, 15-deoxo-30-hydroxyeucosterol 3-O-α-L-rhamnopyranosyl-(1→2)-[(β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (scillanoside L-1, 1) and 3β,31-dihydroxy-17α,23-epoxy-5α-lanost-8-en-23,26-olactone 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (scillanoside L-2, 2), were isolated from the bulbs of Scilla scilloides, together with four that were known (3—6), have been isolated from the bulbs of Scilla scilloides. The structures of the new compounds were determined on the basis of spectroscopic and chromatographic methods, and some chemical transformations were discussed. Amongst the isolated compounds, 3 showed the most significant cytotoxicity against tumor cells tested several types with ED50 value of 1.53—3.06 nM. In vivo experiments, 3 apparently increased the life span of mice bearing Sarcoma 180 tumor cell with T/C value of 239% at dose of 3 mg/kg.
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  • Seven Germacranolides, Eupaglehnins A, B, C, D, E, and F, and 2α-Acetoxyepitulipinolide from Eupatorium glehni
    Motoo Tori, Yoshiko Takeichi, Hiroe Kuga, Katsuyuki Nakashima, Masakaz ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1250-1254
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1250
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    Four new germacrane-type sesquiterpenoids with unsaturated acids as esters at the 8-position, two chlorine atom-containing lactones, 2α-acetoxyepitulipinolide, and 12 previously known compounds have been isolated from the MeOH extract of Eupatorium glehni (Compositae) and their structures have been determined on the basis of spectral data analyses.
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  • The Influence of Ligand Side Chain on the Enantioselectivity of Lewis Acid Catalyzed Diels–Alder Reactions
    Masashige Yamauchi, Kazuhiro Itai, Yuko Honda
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1255-1257
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1255
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    The enantioselective Lewis acid-catalyzed Diels–Alder reaction of 3-(2-propenoyl)-1,3-oxazolidin-2-one 8 with cyclopentadiene was examined using a series of chiral mox ligands 2—6, deferring in the side chain at 2-position of the chiral oxazoline and in the nature of the substituent at the chiral center (4-position) of the oxazoline ring, and a combination of N-[(1R)-2-chloro-1-phenylethyl]-2-[(4R)-4-phenyl-4,5-dihydrooxazol-2-yl]butyramide 2–MgI2–I2 was the most efficient catalyst.
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  • Removal of Fine Powders from Film Surface. I. Effect of Electrostatic Force on the Removal Efficiency
    Satoru Watano, Tomohiro Hamashita, Teruo Suzuki
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1258-1261
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1258
    JOURNAL FREE ACCESS
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    A novel fine particle removal system composed of a corona-discharge neutralizer, a pulse-jet air unit and an image processing system has been developed. First of all, adhesion force between particle and film was directly measured and effect of electrostatic force on the adhesion force was calculated experimentally and theoretically. The electrostatic force was found to be significant, leading to the suggestion that the countermeasure for the electrostatic force was required to effectively remove fine particles. This system was then applied to the removal of fine particles from surface of a gelatin film used for conventional capsule material. The number of particles removed by the system was calculated by an image processing system and number base removal efficiency was computed with and without the elimination of electrostatic charge by the neutralizer. It was found that the difference between the removal efficiency of particles with elimination of electrostatic charge and that of without the elimination showed linear relationship with the electrostatic adhesion force. The data confirmed the necessity of electrostatic charge elimination for the effective removal of fine particles.
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  • Removal of Fine Powders from Film Surface. II. Effect of Operating Parameters on the Removal Efficiency
    Satoru Watano, Takumi Okamoto, Teruo Suzuki
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 9 Pages 1262-1264
    Published: 2002
    Released on J-STAGE: September 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1262
    JOURNAL FREE ACCESS
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    In the previous paper, a novel fine particle removal system composed of a corona-discharge neutralizer, a pulse-jet air unit and an image processing system has been developed and applied to the removal of fine particles from film surface. We have calculated the van der Waals and electrostatic forces between particle and film and then reported that the electrostatic force influenced the adhesion characteristics significantly and thus the elimination of electrostatic charge should be necessary for the effective removal of fine particles. In this paper, we have modified the corona-discharge neutralizer for getting much better removal performance. The effect of operating parameters on the removal efficiency was investigated experimentally. The ratio of fine particle remained on the film surface after removal experiment as a function of particle size was measured. It was found that fine particles smaller than 15 μm, which were impossible to remove by other conventional techniques, could be almost completely removed. This method is anticipated to be used in the capsule filling, film packaging and tabletting processes for prevention of stain on lens of video automatic inspection machines, unpredictable movement of electronic devices, and deteriorates of product quality.
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