Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Volume 53, Issue 3
Displaying 1-22 of 22 articles from this issue
Regular Articles
  • Aziz-ur-rehman, Abdul Malik, Naheed Riaz, Habib Ahmad, Sarfraz Ahmad ...
    2005 Volume 53 Issue 3 Pages 263-266
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    A lignan and two acylphloroglucinols have been isolated from the ethyl acetate soluble fraction of the whole plant of Indigofera hetrantha. Their structures have been assigned on the basis of spectral analysis including 1D and 2D NMR techniques. Compounds 1—3 displayed promising inhibitory potential against enzyme lipoxygenase in concentration-dependent manner.
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  • Xiang-Li Shen, Feng-Peng Wang
    2005 Volume 53 Issue 3 Pages 267-270
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    Treatment of a lycoctonine-type alkaloid acetyllycoctonine (4) with mCPBA at room temperature led to acetyllycoctonine N-oxide (5) as the major product together with other interesting compounds 6—12 as the minor products, which were derived from oxidation involving the nitrogen atom and Cope elimination as well as Polonovski-like fragmentation. All of those new compounds (5—12) were fully characterized.
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  • Tetsuya Hasegawa, Soan Kim, Mamoru Tsuchida, Yasunori Issiki, Seiichi ...
    2005 Volume 53 Issue 3 Pages 271-276
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    The inhibitory effect of poly(2-methacryloyloxyethyl phosphorylcholine-co-butylmetacrylate) (PMB) on the in vitro skin permeation of p-hydroxybenzoic acid and its esters (parabens; methylparaben, ethylparaben, n-propylparaben and n-butylparaben) as model compounds was evaluated. Solubility of the parabens in distilled water was increased by addition of PMB, and the increasing ratio was dependent on the concentration of PMB. The increment of the ratio was more marked in lipophilic parabens than hydrophilic ones. Skin permeability of parabens from their aqueous suspensions was decreased by addition of PMB, and the decreasing ratio was dependent on the PMB concentration. Then, antibacterial effect of parabens of their aqueous solutions was determined with and without PMB by measuring minimum inhibitory concentration (MIC) against E. coli and S. aureus. As results, MIC and antibacterial effect were increased and decreased, respectively, by addition of PMB. The contribution of PMB was more marked in butylparaben than methylparaben. These decreases in skin permeation and antibacterial effect of parabens by PMB are probably due to a higher solubility in water and a lower partition to the skin and bacterial membranes of parabens by addition of PMB.
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  • Emilia Barcia, Alicia Martin, Ma Luz Azuara, Sofia Negro
    2005 Volume 53 Issue 3 Pages 277-280
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    Propacetamol hydrochloride (PRO) is a water-soluble prodrug of paracetamol (PA) which can be parenterally administered as analgesic for the treatment of postoperative pain, acute trauma, and gastric and/or intestinal disorders where oral administration is not possible. In these circumstances, PRO can be administered in physiologic or glucose solutions since it is rapidly and quantitatively hydrolyzed into PA by plasma estearases. We have studied the degradation kinetics of PRO in 5% glucose and 0.9% saline solutions at 4 °C and 25 °C (storage and room temperatures, respectively). The analytic technique used to determine PRO and PA quantitatively was first-derivative spectrophotometry. The degradation process of PRO can be best fitted to a second-order kinetics with independence of the medium used (saline or glucose solution). The hydrolysis kinetics of PRO conversion into PA depends on the temperature but not on the assay medium (saline or glucose solution). The degradation rate constants obtained for PRO were approximately 4.5 times higher at 25 °C than at 4 °C. The values of t90% for PRO were 3.17 h and 3.61 h at 25 °C, and 13.42 h and 12.36 h at 4 °C when the tests were performed in 5% glucose and 0.9% saline solutions, respectively.
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  • İlhami Gülçin, Haci Ahmet Alici, Mehmet Cesur
    2005 Volume 53 Issue 3 Pages 281-285
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    Propofol (2,6-diisopropylphenol) is a hypnotic intravenous agent with in vivo antioxidant properties. This study was undertaken to examine the in vitro antioxidant activity of propofol using different antioxidant tests including by 1,1-diphenyl-2-picryl-hydrazil (DPPH·) radical scavenging, metal chelating, hydrogen peroxide scavenging, superoxide anion radical scavenging, reducing power and total antioxidant activities. At the concentrations of 25, 50, and 75 μg/ml, propofol exhibited 97.7, 98.6 and 100% inhibition on peroxidation of linoleic acid emulsion, respectively. On the other hand, at the 75 μg/ml concentration of standard antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and α-tocopherol exhibited 88.7, 94.5, and 70.4% inhibition on peroxidation of linoleic acid emulsion, respectively. In addition, at same concentrations, propofol was shown that it had effective reducing power, DPPH· free radical scavenging, superoxide anion radical scavenging, hydrogen peroxide scavenging and metal chelating activities. These various antioxidant activities were compared to standard antioxidants such as BHA, BHT and α-tocopherol. These results indicate that propofol prevents lipid peroxidation and radicalic chain reactions. At the same time, propofol revealed more effective antioxidant capacity than BHA, BHT and α-tocopherol.
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  • Chi-I Chang, Mei-Huims Tseng, Yueh-Hsiung Kuo
    2005 Volume 53 Issue 3 Pages 286-289
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    Five new diterpenoids, 11-hydroxyabieta-8,11,13-trien-7-one (1), 11,12,14-trihydroxyabieta-8,11,13-trien-7-one (2), 6β,7α-diacetoxyroyleanone (3), 7β-hydroxymanoyl oxide (4), and 9α-hydroxyisopimara-8(14),15-dien-7-one (5) were obtained from the bark of Taiwania cryptomerioides. The structures of the new compounds 1—5 were elucidated on the basis of spectral analysis and chemical evidence.
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  • Abolghasem Jouyban, Maryam Khoubnasabjafari, Hak-Kim Chan
    2005 Volume 53 Issue 3 Pages 290-295
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    Applicability of a previously published equation for calculating the solubility of solutes in supercritical carbon dioxide was extended to calculate the solubility in entrained supercritical carbon dioxide employing 42 experimental data sets collected from the literature. The accuracy of the proposed model was evaluated by calculating both the average absolute relative deviation and the individual absolute relative deviation. The proposed model showed superiority to a previously published similar model, from both correlation and prediction points of view.
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  • Phan Minh Giang, Phan Tong Son, Yumi Hamada, Hideaki Otsuka
    2005 Volume 53 Issue 3 Pages 296-300
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    Six new ent-kaurane-type diterpenoids were isolated from the leaves of the endemic Vietnamese medicinal plant Croton tonkinensis GAGNEP. (Euphorbiaceae) together with three known ent-11α-acetoxy-7β,14α-dihydroxykaur-16-en-15-one (1), ent-kaur-16-en-15-one 18-oic acid (5) and ent-18-hydroxykaur-16-ene (7). Their structures were determined by spectroscopic analyses to be ent-7β-acetoxy-11α-hydroxykaur-16-en-15-one (2), ent-18-acetoxy-11α-hydroxykaur-16-en-15-one (3), ent-11α-acetoxykaur-16-en-18-oic acid (4), ent-15α,18-dihydroxykaur-16-ene (6), ent-11α,18-diacetoxy-7β-hydroxykaur-16-en-15-one (8), and ent-(16S)-1α,14α-diacetoxy-7β-hydroxy-17-methoxykauran-15-one (14). ent-Kaurane-type diterpenoids from Croton tonkinensis 2—4, 6, and 9—13, were tested for toxicity in the brine shrimp lethality assay. Compounds 9, 10, and 12 demonstrated significant activity, compounds 2, 3, 6, and 11 showed weak activity, and compounds 4 and 13 were inactive.
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  • Yukio Aso, Sumie Yoshioka
    2005 Volume 53 Issue 3 Pages 301-304
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    Factors affecting the storage stability of lyophilized cationic liposomes were investigated using liposomes prepared with various excipients and by different freezing rates, either quick freezing (freezing by immersion into liquid nitrogen) or slow freezing (cooling to −50 °C at a rate of −10 °C/h). Increases in the particle size of cationic liposomes observed during freeze-drying were inhibited by the addition of sucrose, trehalose and sucrose–dextran mixtures (1 : 1 and 2 : 1 by weight). The storage instability of the formulations, as indicated by changes in particle size, was affected by their glass transition temperature (Tg). Addition of high-Tg excipients resulted in smaller increases in the particle size, indicating improvement of storage stability. The storage stability of cationic liposome formulations was also affected by freezing rate. Formulations prepared by slow freezing exhibited better stability. Longer shear relaxation times were observed for formulations prepared by slow freezing compared with those prepared by quick freezing. This indicates that formulations prepared by slow freezing have a lower matrix mobility, which may result in better storage stability. Tg or 1H-NMR relaxation measurements could not detect differences in matrix mobility between formulations prepared by different freezing rates. Shear relaxation measurements seem to be a useful method for evaluating the storage stability of cationic liposome formulations.
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  • Tadahiro Nishimura, Li-Yan Wang, Kouji Kusano, Susumu Kitanaka
    2005 Volume 53 Issue 3 Pages 305-308
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    In our investigation of a cell proliferation-based screening assay using human ligand-dependent cell lines for medicinal herbal extracts, the acetone extract of the whole plants of Euphorbia lunulata (EL) was observed for its proliferation activity for insulin- and interleukin-10 (IL-10)-dependent cell lines. Fractionation of the active extract led to the isolation of one new flavonoid galactoside, quercetin 3-O-(2″,3″-digalloyl)-β-D-galactopyranoside (1), and four known ones, quercetin 3-O-(2″-galloyl)-β-D-galactopyranoside (2), hyperin (3), quercetin (4), and gallic acid (5). Compounds 1 and 2 showed insulin-like activity. Compounds 4 and 5 showed IL-10-like activity. This is the first report of these activities of EL, and 1 and 2 will become the seed compounds for the development of a nonpeptidyl insulin substitutional medicine. Compounds 4 and 5 support the pharmacological use of EL, which has been employed as an herbal medicine for the treatment of bronchial asthma.
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  • Niko Radulović, Dang Ngoc Quang, Toshihiro Hashimoto, Makiko Nuk ...
    2005 Volume 53 Issue 3 Pages 309-312
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    Chromatographic fractionation of the methanol extract of fruiting bodies of the inedible Japanese mushroom Thelephora terrestris (Thelephoraceae) has led to the isolation and characterization of two unusual new pregnane-type steroids, 2β,3α-dihydroxypregna-4,7,16-trien-12,20-dione (2) and 1α,2β,3α-trihydroxypregna-4,7,16-trien-12,20-dione (3) named terresterones A and B (2, 3), as well as the previously known compound stizophyllin, now assigned as 2β,3α,12β-trihydroxypregna-4,7,16-trien-20-one (1). Elucidation of their structures and the revision of the stereochemical assignment of stizophyllin were achieved by means of extensive 1D and 2D NMR, UV, CD, IR, MS and molecular modeling experiments. This paper presents the first report on the isolation of true pregnane-type steroids from the Fungi kingdom.
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  • Tomomi Shimizu, Toshiyuki Kimura, Tatsuya Funahashi, Kazuhito Watanabe ...
    2005 Volume 53 Issue 3 Pages 313-318
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    Seventy eight N3-substituted derivatives of uridine (1), thymidine (2), 2′-deoxyuridine (3), 6-azauridine (4), 2′,3′-O-isopropylideneuridine (5), and arabinofuranosyluracil (6) were synthesized and their antinociceptive effects were evaluated. N3-(2′,4′-Dimethoxyphenacyl)uridine (1l), N3-(2′,4′-dimethoxyphenacyl)2′-deoxyuridine (3l), and N3-(2′,5′-dimethoxyphenacyl)arabinofuranosyluracil (6m) possessed 93, 86, and 82% of the antinociceptive effects tested by hot plate, respectively. The antinociceptive effects of three derivatives were 5.8, 5.4, and 5.1-folds of the effect of N3-phenacyluridine (1h) (16%), respectively. The structure–activity relationship of N3-substituted pyrimidine nucleosides was also discussed.
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  • Akira Kotani, Satoshi Kojima, Hideki Hakamata, Dongri Jin, Fumiyo Kusu
    2005 Volume 53 Issue 3 Pages 319-322
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    A simple and sensitive method has been developed for determining honokiol and magnolol in fresh Magnolia obovata (M. obovata) by micro high-performance liquid chromatography with electrochemical detection (μHPLC-ECD). Chromatography was performed using a Capcell Pak C-18 UG 120 microbore octadecylsilica (ODS) column, methanol–water–phosphoric acid (65 : 35 : 0.5, v/v/v), as a mobile phase and applied potential at +0.8 V vs. Ag/AgCl. Peak heights were found linearly related to the amounts of honokiol and magnolol injected from 0.67 pg to 2.0 ng (r>0.999). The detection limits (S/N=3) were 0.13 pg, respectively. Honokiol and magnolol of 0.27 ng were detected with relative standard deviation (RSD) of 0.73 and 1.17% (n=5), respectively. Honokiol and magnolol in Magnolia Bark of the Japanese Pharmacopoeia were extracted with 70% methanol, diluted with a mobile phase, and injected into the μHPLC-ECD for determination. Recoveries of honokiol and magnolol in Magnolia Bark exceeded 98.7% with RSD, less than 0.93% (n=5). Determination of the distributions of honokiol and magnolol in bark, phloem, wood, leaf blades, and petioles of fresh M. obovata were made using weight samples of 40—238 mg. This method is useful to determine honokiol and magnolol in M. obovata, which is a candidate for crude magnolia bark for traditional Japanese herbal medicines.
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  • Nobuya Ito, Masahiko Suzuki, Akira Kusai, Kozo Takayama
    2005 Volume 53 Issue 3 Pages 323-327
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    The effect of initial panipenem (CAS No. 87726-17-8) concentration on its degradation in an aqueous solution was investigated. The degradation of panipenem followed pseudo-first-order kinetics at all the pH values tested. However, in an acidic solution, the degradation rate increased with the initial panipenem concentration. On the other hand, in an alkaline solution, the degradation rate was not affected by its initial concentration. In an acidic solution, the plots of the first-order rate constants versus initial panipenem concentrations showed a linear relationship. Theoretically, the first-order rate constant is independent of the initial concentration, and therefore, the results suggested unusualness. We investigated the results obtained under acidic conditions in detail to find a very complex reaction mechanism: panipenem and its degradation products are factors causing the unusual increase in the degradation rate. Moreover, it was shown that the dissociation of the carboxyl group played an important role in the degradation of panipenem.
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Notes
  • Pilar Puebla, Sofía Ximena Correa, Mario Guerrero, Rosalí ...
    2005 Volume 53 Issue 3 Pages 328-329
    Published: 2005
    Released on J-STAGE: March 03, 2005
    JOURNAL FREE ACCESS
    The acid fraction of extracts from the aerial part of Croton schiedeanus afforded six cis-clerodane type diterpenoids. Two of them (1 and 4) are new natural compounds. Structural elucidation was achieved on the basis of their spectral data.
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  • Jun Wu, Lijuan Long, Yang Song, Si Zhang, Qingxin Li, Jianshe Huang, Z ...
    2005 Volume 53 Issue 3 Pages 330-332
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    From the cultured marine dinoflagellate Amphidinium carterae, a new unsaturated glycoglycerolipid (2S)-1,2-O-6,9,12,15-dioctadecatetraenoyl-3-O-[α-D-galactopyranosyl-(1″″→6′′′)-O-β-D-galactopyranosyl]-glycerol (1), has been isolated together with two known saturated ones, (2S)-1,2-distearoyl-3-O-(6-sulpho-α-D-quinovopyranosyl)-glycerol (2) and (2S)-1-stearoyl-3-O-(6-sulpho-α-D-quinovopyranosyl)-glycerol (3). Their structures were elucidated on the basis of chemical and spectral data.
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  • Subehan, Tepy Usia, Shigetoshi Kadota, Yasuhiro Tezuka
    2005 Volume 53 Issue 3 Pages 333-335
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    A new sesquiterpene 2,9-humuladien-6-ol-8-one (1) was isolated from methanol extract of Zingiber aromaticum, along with 15 known compounds. The structures of the isolated compounds were elucidated on the basis of spectroscopic analyses. The isolated compounds were tested for their inhibitory activity on the metabolism mediated by cytochrome P450 3A4 (CYP3A4) and CYP2D6.
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  • Pei-Wen Hsieh, Fang-Rong Chang, Ching-Chung Wu, Chien-Ming Li, Kuen-Yu ...
    2005 Volume 53 Issue 3 Pages 336-338
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    A new cyclic peptide, longicalycinin A (1), and six known compounds, vaccaroside A, dianoside A, dianoside G, 3-(4-hydroxy-3-methoxy-phenyl)propionic acid methyl ester, p-hydroxybenzoic acid, and p-hydroxybenzaldehyde were isolated from the MeOH extract of Dianthus superbus var. longicalycinus. The amino acid sequences of 1 was elucidated as cyclo(Gly1-Phe2-Tyr3-Pro4-Phe5-) on the basis of ESI tandem mass fragmentation analysis, chemical evidence, and extensive 2D NMR methods. Furthermore, compound 1 showed cytotoxicity to Hep G2 cancer cell line.
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  • Zhi-Hong Jiang, Takashi Tanaka, Hiromi Iwata, Saori Sakamoto, Yoko Hir ...
    2005 Volume 53 Issue 3 Pages 339-341
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    Three new ellagitannins named balanophotannins A—C having a 1,1′-(3,3′,4,4′-tetrahydroxy)dibenzofurandicarboxyl group in their molecules and four known lignan glycosides were isolated from the extracts of fresh aboveground and underground parts of a medicinal parasitic plant Balanophora japonica (Balanophoraceae). Their structures were elucidated on the basis of spectral and chemical evidence. Chemotaxonomic significance of the known lignan glycosides in Balanophora japonica was discussed.
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  • Vatcharin Rukachaisirikul, Wanpen Naklue, Yaowapa Sukpondma, Souwalak ...
    2005 Volume 53 Issue 3 Pages 342-343
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    From the methanol extract of the twigs and leaves of Garcinia bancana MIQ., one new biphenyl derivative (1), was isolated and characterized along with nine known compounds; garcinol, isogarcinol, (−)-mellein, 8-hydroxy-6-methoxy-3-n-pentylisocoumarin, blumenol C O-β-D-glucoside, quercetin 3-O-α-L-rhamnoside, kaemferol 3-O-α-L-rhamnoside, lupeol and stigmasterol. Their structures were determined by analysis of 1D and 2D NMR data and comparison of spectral data and physical data with those previously reported. The antibacterial activity against methicillin-resistant Staphylococcus aureus was evaluated. Garcinol showed the lowest minimum inhibition concentration (MIC) at 16 μg/ml while compound 1 exhibited weaker activity with MIC value of 64 μg/ml.
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  • Masahiro Ogata, Kazuo Shin-ya, Shiro Urano, Toyoshige Endo
    2005 Volume 53 Issue 3 Pages 344-346
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    This study was carried out to investigate the antioxidant activity of propofol (2,6-diisopropylphenol) and its related compounds, butylated hydroxyanisole (BHA), 2,6-dimethylphenol, 2,6-di-t-butylphenol, and their dimeric compounds. The degree of antioxidant activity was evaluated based on the degree of peroxidation induced with Fe-ascorbic acid in egg phosphatidylcholine through the determination of thiobarbituric acid-reactive substances (TBARS) formed during peroxidation. Their antioxidant activities were in the order of dipropofol>di(2,6-di-t-butylphenol)>diBHA>di(2,6-dimethylphenol). Dipropofol, a dimeric compound of propofol, showed the highest antioxidant activities. Dimeric compounds had higher activities than monomeric compounds, and the 1,1-diphenyl-p-picryhydrazyl-trapping ability of dimeric compounds was also greater than those of monomeric compounds (4–10-fold). These results suggest that dimeric phenols may increase their antioxidant activities along with increments in the conjugation system and play a inhibitory role in the propagation of free radical chain reactions.
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  • Chia-Ying Li, Chung-Hua Lin, Tian-Shung Wu
    2005 Volume 53 Issue 3 Pages 347-349
    Published: 2005
    Released on J-STAGE: March 03, 2005
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    A quantitative analysis using 1H-NMR has been developed for the determination of camptothecin derivatives and trigonelline in Nothapodytes foetida root, stems and leaves. In the region of δ 9.5—5.5, the signals of H-7 of camptothecin (1), H-10 of 9-methoxycamptothecin (2), H-19 of pumiloside (3) and H-2 of trigonelline (4), were well separated from each other in DMSO-d6. The quantity of the compounds was calculated by the ratio of the intensity of each compound to the known amount of internal standard 3,4,5-trimethoxybenzaldehyde. These results were compared with the conventional HPLC method. The advantages of the method are that no reference compounds are required for calibration curves, the quantification could be directly realized on a crude extract, an overall profile of the preparation could be directly obtained, and a very significant time-gain could be achieved, in comparison to conventional HPLC methods, for instance.
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