Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
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ISSN-L : 0009-2363
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Volume 52, Issue 5
Displaying 1-32 of 32 articles from this issue
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Regular Articles
  • Synthesis and Biological Activity of Novel Retinamide and Retinoate Derivatives
    Soo-Jong Um, Youn-Ja Kwon, Hye-Sook Han, Si-Ho Park, Myoung-Soon Park, ...
    2004 Volume 52 Issue 5 Pages 501-506
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.501
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    Retinoic acid and its amide derivative, N-(4-hydroxyphenyl)retinamide (4-HPR), have been proposed as chemopreventative and chemotherapeutic agents. However, their low cytotoxic activity and water solubility limit their clinical use. In this study, we synthesized novel retinoid derivatives with improved cytotoxicity against cancer cells and increased hygroscopicity. Our syntheses were preceded by selective O-acylation and N-acylation, which led to the production of retinoate and retinamide derivatives, respectively, in one pot directly from aminophenol derivatives and retinoic acid without protection. Transcription assays in COS-1 cells indicated that the N-acylated derivatives (2A—5A) and 4-HPR (1A) were much weaker ligands for all three subtypes of retinoic acid receptor (RAR) than all-trans retinoic acid (ATRA), although they showed some selectivity for RARβ and RARγ. In contrast, the O-acylated retinoate derivatives (1B—5B) activated all three RAR isotypes without specificity to an extent similar to ATRA. The cytotoxicity was determined using an MTT assay with HCT116 colon cancer cells, and the IC50 of N-acylated retinamide derivative 4A and O-acylated retinoate derivative 5B was 1.67 μM and 0.65 μM, respectively, which are about five and 13-fold better than that of 4-HPR (8.21 μM), a prototype N-acylated derivative. When retinoate derivative 5B was coupled to organic acid salts, the resulting salt derivatives 5C and 5D had RAR activation and cytotoxicity similar to those of 5B. These data may delineate the relationship between the structure and function of retinoate and retinamide derivatives.
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  • A Novel Podophyllotoxin Lignan from Justicia heterocarpa
    Salih Salem Al-Juaid, Mamdouh Abdel-Mogib
    2004 Volume 52 Issue 5 Pages 507-509
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.507
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    Chromatographic separation of the extract of Justicia heterocarpa T. ANDERS. afforded, in addition to known fatty acids, terpenoids and steroids, a new podophyllotoxin lignan. Structures were elucidated by spectroscopic methods, and the structure of the new lignan was confirmed by single crystal X-ray diffraction studies, which have shown that there is a H-bonding stabilized dimer.
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  • Rheological Analysis and Quantitative Evaluation of Wet Kneaded Wax Matrix
    Hidaka Abe, Tetsuya Suzuki, Ayako Ootsuki, Kazuhiko Ozaki, Hirofumi Sa ...
    2004 Volume 52 Issue 5 Pages 510-516
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.510
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    The properties of the wet kneaded wax matrix were evaluated using a compression tester, whereby a newly proposed σ index for the plastic deformation was assessed in the pressure transmission diagram. The σ index was indicative of a characteristic of the plastic yield point in the rheological behavior, and presented an initial and abrupt deformation of wet kneaded mass when the wet kneaded mass was subjected to the pressure. The value of σ index was confirmed to decrease along with an increase in the plasticity of wet kneaded mass. The wet mass of wax matrix was prepared under various kneading time, and then extruded. The properties of the extruded granules such as pore volume, strength and dissolution were investigated. As a result, it was found that the σ index decreased with an increase in kneading time. The granules with small value of σ index showed few porosities, large strength and slow dissolution. It was demonstrated that the σ index linked the characteristics of wet kneaded mass to the dissolution and the other granule properties. Existence of this link was revealed by σ index evaluation relevant to the plasticity. The σ index could be a decisive criterion to permit an in-process evaluation of the kneading progress quantitatively, and also useful for anticipating the dissolution of the final granules roughly.
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  • Electronic Structure of Brain: Structure–Activity Relationships between Electronic Structure and Neurotransmitters Based on Molecular Hardness Concept
    Shigeki Kobayashi, Yuki Terao
    2004 Volume 52 Issue 5 Pages 517-523
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.517
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    In order to understand the relation between the electronic structure of neurotransmitters and the brain, a model of the brain based on absolute hardness (η) and absolute electronegativity (χ) is described. It was found that the coordinate r(χ, η) of electronic structures of neurotransmitters obtained using the parameters η and χ can be graphically classified into three groups: catecholamine type (group I), gamma-aminobutanoic acid (GABA) type (group II), and acetylcholine (ACh) type (group III) in the η–χ diagram. The results suggest that the brainstem and neocortex in the brain are chemically soft and hard, respectively, because they show that the myelinated nerve is chemically soft and the unmyelinated nerve is chemically hard. If one calculates the r(χ, η) to understand which group a drug belongs to, one can predict the target receptors of the drug from the η–χ diagram. Using η–χ maps, one is then able to design medications like antidepressants, tranquilizers, and ACh agonists.
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  • Grinding-Induced Equimolar Complex Formation between Thiourea and Ethenzamide
    Kunikazu Moribe, Masami Tsuchiya, Yuichi Tozuka, Kentaro Yamaguchi, To ...
    2004 Volume 52 Issue 5 Pages 524-529
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.524
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    We prepared and characterized a grinding-induced equimolar complex of thiourea with ethenzamide. When thiourea and ethenzamide were co-ground at a molar ratio of 3 : 1, new powder X-ray diffraction (PXRD) peaks were observed in addition to PXRD peaks of thiourea crystals. The optimum stoichiometry of the new structure was confirmed as 1 : 1 mol/mol. Effect of grinding time on the thiourea–ethenzamide equimolar complex formation was investigated by using PXRD, differential scanning calorimetry and Fourier transform infrared spectroscopy. The equimolar crystal structure was confirmed by X-ray diffraction measurements of the single crystal which was recrystallized from ethanol. It was found that the intermolecular hydrogen bond formations between thiourea and ethenzamide molecules contributed to the equimolar complex formation. The complex formation was not observed in the cases where benzamide, salicylamide or 3-ethoxybenzamide was co-ground with thiourea. 2-Alcoxyl benzamide structures should be required for the grinding-induced equimolar complex formation with thiourea.
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  • Three New Norditerpenoid Alkaloids from Consolida orientalis
    Alenguer Alva, Maritza Grandez, Alberto Madinaveitia, Gabriel de la Fu ...
    2004 Volume 52 Issue 5 Pages 530-534
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.530
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    The structures of three new norditerpenoid alkaloids named dehydrodeltatsine (1), 14-O-acetyltakaosamine (2), 18-demethoxypubescenine (3) isolated from the aerial parts of Consolida orientalis (GAY) SCHRÖD., were elucidated by 1D and 2D NMR spectroscopy and HR-EIMS. Twelve known norditerpenoid alkaloids (type lycoctonine) and the diterpenoid alkaloid ajaconine have been isolated. Several assignments of 13C-NMR data for delbonine (4) were revised and the complete assignment for 18-hydroxy-14-O-methylgadesine (5) was realized.
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  • Novel 17 Substituted Pregnadiene Derivatives as 5α-Reductase Inhibitors and Their Binding Affinity for the Androgen Receptor
    Marisa Cabeza, Eugenio Flores, Ivonne Heuze, Mauricio Sánchez, ...
    2004 Volume 52 Issue 5 Pages 535-539
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.535
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    The in vitro antiandrogenic activity of four new progesterone derivatives: 4, 5, 6 and 7 (8 is a known compound) was determined. These compounds were evaluated as 5α-reductase inhibitors as well as by their capacity to bind to the androgen receptor in gonadectomized hamster prostate. The IC50 value was determined using increasing concentrations of 4, 5, 6, 7 and 8 in the presence of [3H]T and the microsomal fraction of the hamster prostate containing the 5α-reductase enzyme. In this paper we also demonstrated the effect of increasing concentrations of the novel steroids upon [3H]DHT binding to the androgen receptors from hamster prostate which produces competition for the androgen receptor sites. The in vitro studies showed that steroids 4, 5, 6, 7 and 8 had an inhibitory activity for the 5α-reductase with IC50 of: 4 (0.17 μM), 5 (0.19 μM), 6 (1 μM), 7 (4.2 μM), and 8 (2.7 μM). On the other hand, the IC50 value for compounds 4, 5, 6, 7, 8 and DHT showed the following order of affinity for the androgen receptor: 6>7>5>DHT. Surprisingly compounds 4 and 8 did not bind to the androgen receptor. The overall data indicate that all synthesized compounds are inhibitors for the enzyme 5α-reductase present in the hamster prostate. In contrast, compounds 5, 6 and 7, which have a cyclohexyl group in the side chain showed a high affinity for the androgen receptor.
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  • Synthesis and Cytotoxic Activity of Pyranocarbazole Analogues of Ellipticine and Acronycine
    Hong Anh Tran-Thi, Thuan Nguyen-Thi, Sylvie Michel, Francois Tillequin ...
    2004 Volume 52 Issue 5 Pages 540-545
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.540
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    Various 2,2,5,11-tetramethyl- and 2,2,5,6,11-pentamethyl-2,6-dihydropyrano[3,2-b]carbazole derivatives were synthesized by condensation of 3-methylbut-2-enal or 3-chloro-3-methylbut-1-yne with an appropriate hydroxycarbazole. These compounds associate the tricyclic system responsible for the intercalating properties of ellipticine related drugs, with the dimethylpyran pharmacophore of acronycine derivatives. The study of the biological properties of the new pyrano[3,2-b]carbazole derivatives was carried out in vitro on L1210 murine leukaemia cell line. The three (±)-cis-diol diesters 15, 16, and 18 were the most active compounds.
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  • Investigation of Intermolecular Interaction in Molecular Complex of Tryptamine and Benzoic Acid by Solid-State 2D NMR
    Akira Terakita, Hirokazu Matsunaga, Takahiro Ueda, Taro Eguchi, Midori ...
    2004 Volume 52 Issue 5 Pages 546-551
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.546
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    Solid-state NMR spectra and powder X-ray diffraction of the two-component molecular complex composed of tryptamine and benzoic acid were observed to investigate the intermolecular interaction in the molecular complex. 1D 13C CP/MAS NMR spectrum and powder X-ray diffraction pattern of the complex was clearly different from the convolution of each spectrum of the single component. 2D 1H–13C heteronuclear-correlation (HETCOR) NMR technique indicated that the intermolecular interaction between the primary amine of tryptamine and the carboxyl group of benzoic acid must be related to the complex formation.
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  • High Performance Liquid Chromatography with an Electrochemical Detector in the Cathodic Mode as a Tool for the Determination of p-Nitrophenol and Assay of Acid Phosphatase in Urine Samples
    Yuji Yamauchi, Megumi Ido, Merime Ohta, Hatsuo Maeda
    2004 Volume 52 Issue 5 Pages 552-555
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.552
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    Utilizing a commercially available helium-purging device and PEEK tubes for all tubing, especially for connection between the mobile phase and pump, high performance liquid chromatography with an electrochemical detector (ECD/HPLC) at the cathodic mode is a simple and precise method for the determination of p-nitrophenol (NP). Studies with cyclic and hydrodynamic voltammetry indicated that 25% aqueous MeOH containing 0.1% (v/v) CF3CO2H and −0.8 V vs. Ag/AgCl are the best mobile phase and detection potential for cathodic ECD/HPLC. With the present system, the limits of detection and determination were 0.2 and 0.25 μM, respectively, and up to 50 μM, a linear calibration curve was afforded. Within-day precisions for the analysis of 5 and 50 μM NP were 0.8 and 0.7% (n=6), respectively, and between-day precisions (n=6) for these samples were 3.5 and 2.2%, respectively. Compared with the commonly used Bessey–Lowry–Brock method, cathodic ECD/HPLC was useful for the assay of acid phosphatase in urine samples with p-nitrophenyl phosphate disodium salt as a substrate.
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  • Terpenoids and Aromatic Compounds from the New Zealand Liverworts Plagiochila, Schistochila, and Heteroscyphus Species
    Fumihiro Nagashima, Takashi Sekiguchi, Shigeru Takaoka, Yoshinori Asak ...
    2004 Volume 52 Issue 5 Pages 556-560
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.556
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    A new clerodane- and two new ent-rosane-type diterpenoids have been isolated from the New Zealand liverworts Heteroscyphus billardierii and Plagiochila deltoidea, respectively. The known bisbibenzyl compounds and acetophenones have also been isolated from Schistochila glaucescens and Plagiochila fasciculata. Their structures were established by extensive NMR techniques. Chemosystematics of the Plagiochila species have been discussed.
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  • Acid-Base Cosolvent Method for Determining Aqueous Permeability of Amiodarone, Itraconazole, Tamoxifen, Terfenadine and Other Very Insoluble Molecules
    Jeffrey Alan Ruell, Oksana Tsinman, Alex Avdeef
    2004 Volume 52 Issue 5 Pages 561-565
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.561
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    A high-throughput, UV-detection PAMPA (parallel artificial membrane permeability assay) cosolvent procedure is described, based on the use of 20% v/v acetonitrile in aqueous buffer. A training set of 32 drugs (17 bases, 13 acids, 2 ampholytes) was studied both in aqueous buffer and in cosolvent-buffer solutions. A procedure was devised, where intrinsic permeability values, log PoCOS, measured in cosolvent solution, are converted to values expected under cosolvent-free conditions, using an in silico model based on Abraham H-bond acidity (α) and basicity (β) descriptors, developed with the Algorithm Builder computer program, to obtain aqueous intrinsic permeability values: log Po=0.738+0.885 log PoCOS−1.262α+0.436β, r2=0.97, q2=0.96, s=0.38, n=32, F=279. Five sparingly-soluble weak bases (solubility <1 μg/ml), which could not be characterized without cosolvent, had their aqueous intrinsic permeability, Po, estimated: miconazole 0.32 cm/s; itraconazole 3.2 cm/s; amiodarone 13 cm/s; tamoxifen 28 cm/s; terfenadine 162 cm/s.
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  • New α-Tetralonyl Glucosides from the Fruit of Juglans mandshurica
    Lijuan Liu, Wei Li, Kazuo Koike, Shujie Zhang, Tamotsu Nikaido
    2004 Volume 52 Issue 5 Pages 566-569
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.566
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    Five new α-tetralonyl glucosides, juglanosides A—E (1—5) were isolated from the fresh rejuvenated fruit of Juglans mandshurica. Their structures were elucidated as (4S)-4-hydroxy-α-tetralone 4-O-β-D-glucopyranoside (1), (4S)-4,5-dihydroxy-α-tetralone 4-O-β-D-glucopyranoside (2), (4S)-4,6-dihydroxy-α-tetralone 4-O-β-D-glucopyranoside (3), (4S)-4,5,8-trihydroxy-α-tetralone 4-O-β-D-glucopyranoside (4), and (4S)-4,5,8-trihydroxy-α-tetralone 5-O-β-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence.
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  • Product Analyses of Ozone Mediated Nitration of Benzimidazole Derivatives with Nitrogen Dioxide: Formation of 1-Nitrobenzimidazoles and Conversion to Benzotriazoles
    Toyo Kaiya, Kei Nakamura, Masaru Tanaka, Naoki Miyata, Kohfuku Kohda
    2004 Volume 52 Issue 5 Pages 570-576
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.570
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    Several benzimidazole derivatives having electron-withdrawing or -donating substituent(s) at the benzene moiety were used as models of the imidazole moiety of purine bases and their nitration with nitrogen dioxide and ozone (so-called Kyodai nitration) were examined. Products were extracted from the reaction mixture with AcOEt and their structures were analyzed. 1-Nitrobenzimidazole derivatives and unexpected 1-nitrobenzotriazole derivatives were identified. Although the yields of 1-nitrobenzimidazole derivatives were quite low, these were all new compounds that could be obtained only by Kyodai nitration. It was speculated that benzotriazoles were formed via 1-nitrobenzimidazoles and subsequent nitration toward benzotriazoles resulted in the formation of 1-nitrobenzotriazoles.
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  • Orally Active CCR5 Antagonists as Anti-HIV-1 Agents: Synthesis and Biological Activity of 1-Benzothiepine 1,1-Dioxide and 1-Benzazepine Derivatives Containing a Tertiary Amine Moiety
    Masaki Seto, Yoshio Aramaki, Tomohiro Okawa, Naoki Miyamoto, Katsuji A ...
    2004 Volume 52 Issue 5 Pages 577-590
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.577
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    The search for orally active CCR5 antagonists was performed by chemical modification of the 1-benzothiepine 1,1-dioxide 3 and 1-benzazepine 4 lead compounds containing a tertiary amine moiety. Replacement of methyl group with a 2-(C2—4 alkoxy)ethoxy group at the 4-position on the 7-phenyl group of the 1-benzothiepine ring resulted in both enhanced activity and significant improvement in the pharmacokinetic properties upon oral administration in rats. Introduction of C2—4 alkyl, phenyl or (hetero)arylmethyl groups as the 1-substituent on the 1-benzazepine ring together with the 2-(butoxy)ethoxy group led to further increase of activity. Among the 1-benzazepine derivatives, the isobutyl (6i), benzyl (6o) or 1-methylpyrazol-4-ylmethyl (6s) compounds were found to exhibit highly potent inhibitory effects, equivalent to the injectable CCR5 antagonist 1, in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound 6s showed the most potent CCR5 antagonistic activity (IC50=2.7 nM) and inhibitory effect (IC50=1.2 nM) on membrane fusion, together with good pharmacokinetic properties in rats. The synthesis of 1-benzothiepine 1,1-dioxide and 1-benzazepine derivatives and their biological activity are described.
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  • Glochidiolide, Isoglochidiolide, Acuminaminoside, and Glochidacuminosides A—D from the Leaves of Glochidion acuminatum MUELL.
    Hideaki Otsuka, Yoshio Takeda, Eiji Hirata, Takakazu Shinzato, Masahik ...
    2004 Volume 52 Issue 5 Pages 591-596
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.591
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    The dimeric butenolides glochidiolide and isoglochidiolide, a new glucoside of a nitrogen-containing C8 dimer, acuminaminoside, and glucosides of C8 compounds, designated glochidacuminosides A—D, were isolated from the leaves of Glochidion acuminatum. The structures of glochidionolactone and acuminaminoside were determined by X-ray analyses, and those of the remaining C8 glucosides by NMR spectroscopic analyses, chemical conversion, and a modified Mosher's method.
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Notes
  • Effect of a New β-Sitosterol Analogue on Plasma Lipid Concentrations in Rats
    Yang-Heon Song, Soonil Hong, Hongsan Lim, Jinmoo Seo, Sungjoo Chung, I ...
    2004 Volume 52 Issue 5 Pages 597-601
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.597
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    N-Substituted succinamic acid β-sitosteryl ester derivatives were prepared and evaluated. Compounds 1 and 2 were prepared in 76—92% yields by the reaction of β-sitosterol and succinic anhydride, followed by the activation of the resulting acid compound 1 by thionyl chloride or methyl chloroformate, and finally by amination with appropriate amines. Compound 2a (DANA87) was also easily obtained in one step by the direct addition of β-sitosterol to dicyclohexylcarbodiimide (DCC) in 80% yield. Administration of the dietary compound DANA87 resulted in significant decreases in total plasma cholesterol (TC) and low-density lipoprotein (LDL) cholesterol concentrations compared with controls in a rat model. High-density lipoprotein cholesterol and plasma triglyceride levels were not affected. These findings indicate that DANA87 functions as TC and LDL cholesterol-reducing agent.
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  • Antitrypanosomal Activity of Brazilian Propolis from Apis mellifera
    Ildenize Barbosa da Silva Cunha, Kelly Salomão, Mario Shimizu, ...
    2004 Volume 52 Issue 5 Pages 602-604
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.602
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    Extracts from different samples of Brazilian propolis were obtained by Soxhlet extraction or maceration at room temperature using ethanol, water, and accombination of both solvents. Analysis of their composition using HPLC revealed that no major differences were seen when a propolis sample was subject to different extraction methods. The activity of the 15 extracts was assayed against bloodstream trypomastigotes of Trypanosoma cruzi, the etiologic agent of Chagas' disease. Multivariate analysis was applied to evaluate the efficiency of the different extracts and the trypanocidal activity. The extracts could be divided into two groups. In the first, in which, extracts were obtained by reflux in Soxhlet using 100% ethanol, there was a lower content of bioactive compounds and consequently lower trypanocidal activity. Extract 136-Et100 stands out in this group, since it had the highest levels of bioactive compounds together with highest activity against the parasite when compared with all other extracts. The second group comprises extracts with intermediate levels of bioactive compounds and higher activity against T. cruzi.
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  • Properties of Calcium-Induced Gel Beads Prepared with Alginate and Hydrolysates
    Yoshifumi Murata, Daisaku Jinno, Kyouko Kofuji, Susumu Kawashima
    2004 Volume 52 Issue 5 Pages 605-607
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.605
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    Calcium-induced alginate gel beads (Alg-Ca) containing alginate hydrolysate, such as the guluronic acid block (GB), was prepared and the drug release profiles were investigated under simulated gastrointestinal conditions. The addition of GB to Alg-Ca altered its rheological properties. A model drug (hydrocortisone) was incorporated at 78% of its theoretical yield within the dried Alg-Ca containing 5% GB and it was gradually released from the beads in JP XIV 1st medium for disintegration test (pH 1.2), while it was rapidly released with disintegration of the gel matrix in JP XIV 2nd medium (pH 6.8). In contrast, for Alg-Ca containing GB and chitosan, disintegration was not observed in these media and the drug release rate was markedly different. These results demonstrate that the release profiles of drugs incorporated into Alg-Ca can be controlled by adding these polysaccharides.
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  • New Lathyrane and Podocarpane Diterpenoids from Jatropha curcas
    Nasi Ravindranath, Majjigapu Ravinder Reddy, Chimmani Ramesh, Ravirala ...
    2004 Volume 52 Issue 5 Pages 608-611
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.608
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    Chemical investigation on Jatropha curcas resulted in the isolation of twenty constituents among which four diterpenoids were unknown and six compounds, tetradecyl-(E)-ferulate, 3-O-(Z)-coumaroyl oleanolic acid, heudelotinone, epi-isojatrogrossidione, 2α-hydroxy-epi-isojatrogrossidione, and 2-methyanthraquinone had not been reported earlier from this species. The structures of the new compounds were established by extensive studies of their 1D- and 2D-NMR spectra.
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  • Phenylethanoid and Iridoid Glycosides from the Thai Medicinal Plant, Barleria strigosa
    Tripetch Kanchanapoom, Pawadee Noiarsa, Somsak Ruchirawat, Ryoji Kasai ...
    2004 Volume 52 Issue 5 Pages 612-614
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.612
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    A phenylethanoid (4-hydroxyphenylethyl 4-O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranoside) and an iridoid (10-O-trans-coumaroyl-eranthemoside) were isolated from an entire Barleria strigosa plant together with verbascoside, isoverbascoside, decaffeoylverbascoside, (+)-lyoniresinol 3α-O-β-D-glucoside, apigenin 7-O-α-L-rhamnosyl-(1→6)-O-β-D-glucoside, 7-O-acetyl-8-epi-loganic acid and (3R)-1-octen-3-ol-3-O-β-D-xylosyl-(1→6)-β-D-glucoside. The structural elucidations were based on analyses of physical and spectroscopic data.
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  • Antioxidative Phenylethanoid and Phenolic Glycosides from Picrorhiza scrophulariiflora
    Hao Wang, Yang Sun, Wen-Cai Ye, Fei Xiong, Jia-Jun Wu, Chun-Hua Yang, ...
    2004 Volume 52 Issue 5 Pages 615-617
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.615
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    One new phenylenthanoid glycoside, scroside D (2), was isolated from the roots of Picrorhiza scrophulariiflora (Scrophulariaceae), together with nine known phenylethanoid and phenolic glycosides: 2-(3,4-dihydroxyphenyl)-ethyl-O-β-D-glucopyranoside (1), 2-(3-hydroxy-4-methoxyphenyl)-ethyl-O-β-D-glucopyranosyl (1→3)-β-D-glucopyranoside (3), scroside B (4), hemiphroside A (5), plantainoside D (6), scroside A (7), androsin (8), piceoside (9), and 6-O-feruloyl-β-D-glucopyranoside (10). The structures of these compounds were elucidated using spectroscopic methods. The antioxidative activities of these isolated compounds were evaluated based on their scavenging effects on hydroxyl radicals and superoxide anion radicals, respectively. Compounds 1, 2, and 6 showed potent antioxidative effects as those of ascorbic acid and the structure–activity relationship is discussed.
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  • Studies on the Constituents of Catalpa Species. IX.
    Iridoids from the Fallen Leaves of Catalpa ovata G. DON
    Koichi Machida, Erika Hishinuma, Masao Kikuchi
    2004 Volume 52 Issue 5 Pages 618-621
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.618
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    Two new iridoids, 6-O-trans-p-coumaroyl-7-deoxyrehmaglutin A (1) and 6-O-cis-p-coumaroyl-7-deoxyrehmaglutin A (2), were isolated from the fallen leaves of Catalpa ovata G. DON. together with six artifact iridoids (3—8). Their structures were established by spectral analysis. In addition, the scavenging effects of the principal compounds isolated from this plant on 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activity were examined.
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  • Three New Cycloartane Triterpene Glycosides from Souliea vaginata
    Liang Zhou, JunShan Yang, JianHua Zou, GuangZhong Tu
    2004 Volume 52 Issue 5 Pages 622-624
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.622
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    Three new cycloartane triterpene glycosides, soulieosides A (1), B (2), and C (3), were isolated from the rhizomes of Souliea vaginata, and their structures were elucidated on the basis of extensive NMR experiments and chemical methods. Soulieosides A—C were assigned as 25-O-acetylcimigenol-3-O-β-D-(2-acetyl)xylopyranoside (1), 24-O-acetyl-isodahurinol-3-O-β-D-(2-acetyl)xylopyranoside (2) and 20(S),22(R),23(S),24(R)-16β:23;22:25-diepoxy-3β,23,24-trihydroxy-9,19-cyclolanostane-3-O-β-D-(4-acetyl)xylopyranoside (3), respectively.
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  • Aerobic Oxidation of Thiols to Disulfides Catalyzed by Trichlorooxyvanadium
    Masayuki Kirihara, Kumiko Okubo, Tomoyuki Uchiyama, Yoko Kato, Yuta Oc ...
    2004 Volume 52 Issue 5 Pages 625-627
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.625
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    Thiols were converted into disulfide by the aerobic oxidation catalyzed by trichlorooxyvanadium in the presence of molecular sieves 3A.
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  • Structural Dependence of HPLC Separation Pattern of Anthocyanins from Bilberry (Vaccinium myrtillus L.)
    Takashi Ichiyanagi, Yoshihiko Hatano, Seiichi Matsugo, Tetsuya Konishi
    2004 Volume 52 Issue 5 Pages 628-630
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.628
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    An HPLC method using isocratic elution was established for the analysis of fifteen anthocyanins contained in bilberry (Vaccinium myrtillus L.). Separation was attained by using an aqueous solution of 20% methanol containing 0.5% TFA as the mobile phase with a flow rate of 2 ml/min. The detection limit was 0.3 pmol for delphinidin 3-O-β-D-glucopyranoside, which is a major anthocyanin in bilberry extract. The reproducibility was 0.19—3.85% (S.E.M) for peak area and 0.64—0.77% (S.E.M) for relative mobility normalized by the elution position of the solvent peak. When the relative elution volumes of each anthocyanins were correlated to their corresponding anthocyanin structures, a characteristic pattern was observed. From this pattern, the structures of unknown anthocyanins could be predicted from their elution times. Therefore, the present method is useful for the study of anthocyanins from various biological sources.
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  • Diacylated 8-C-Glucosylcyanidin 3-Glucoside from the Flowers of Tricyrtis formosana
    Fumi Tatsuzawa, Norio Saito, Kazumitsu Miyoshi, Koichi Shinoda, Atsush ...
    2004 Volume 52 Issue 5 Pages 631-633
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.631
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    A new diacylated 8-C-glucosylanthocyanin was isolated from the purple flowers of Tricyrtis formosana ‘Fujimusume’ as one of the major anthocyanins along with four known pigments. The structure of this pigment was determined to be 8-C-(6-O-trans-sinapoyl)-β-glucopyranosylcyanidin 3-O-(6-O-malonyl-β-glucopyranoside) by chemical and spectroscopic methods. In addition, four known pigments, 8-C-glucosylcyanidin 3-malonylglucoside, cyanidin 3-glucoside, cyanidin 3-rutinoside and cyanidin 3-malonylglucoside, were identified as the major anthocyanins in the flowers.
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  • Structure–Activity Relationships of 2-Aminothiazole Derivatives as Inducible Nitric Oxide Synthase Inhibitor
    Shigeo Ueda, Hideo Terauchi, Motoji Kawasaki, Akihiro Yano, Motoharu I ...
    2004 Volume 52 Issue 5 Pages 634-637
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.634
    JOURNAL FREE ACCESS
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    Nitric oxide synthase (NOS) has been divided into two major sub-enzymes, i.e. inducible NOS (iNOS) and constitutive NOS (cNOS). Although nitric oxide (NO) plays an important role as host defense mediator, excessive production of NO by iNOS has been involved in the pathology of many inflammatory diseases. Recently, we reported that the 2-imino-1,3-oxazolidine (1a) weakly inhibits iNOS and that introduction of an alkyl moiety on the oxazolidine ring of 1a enhances the inhibitory activity and selectivity for iNOS. In our search for better iNOS inhibitors, we focused our efforts on the 2-aminothiazole scaffold 3 as it possesses a ring similar to that of 1a. In this study, we evaluated the inhibitory activity of a series of 2-aminothiazole derivatives against both iNOS and neuronal NOS (nNOS). Our results show that introduction of appropriately-sized substituents at the 4- and 5-position of the 2-aminothiazole ring improves the inhibitory activity and selectivity for iNOS. We also found that the selectivity of 5a [5-(1-methyl)ethyl-4-methylthiazol-2-ylamine] and 5b [5-(1,1-dimethyl)ethyl-4-methylthiazol-2-ylamine] for iNOS was similar to that of oxazolidine derivative 1b (4-methyl-5-propyl-2-imino-1,3-oxazolidine) and much higher than that of L-NAME. However, we could not enhance the inhibitory activity against iNOS by introducing an alkyl substituent into the 2-aminothiazole ring as we could in the case of oxazolidine one. On the other hand, introduction of bulky or hydrophilic substituent at any position of the 2-aminothiazole ring remarkably decreased or even abolished the inhibitory activity against NOS.
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  • New Lignan Glucosides from the Stems of Tinospora sinensis
    Wei Li, Kazuo Koike, Lijuan Liu, Lianbo Lin, Xiaowen Fu, Yingjie Chen, ...
    2004 Volume 52 Issue 5 Pages 638-640
    Published: 2004
    Released on J-STAGE: May 05, 2004
    DOIhttps://doi.org/10.1248/cpb.52.638
    JOURNAL FREE ACCESS
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    Two new lignan glucosides, tinosposides A and B (1 and 2), were isolated from the stems of Tinospora sinensis collected in Hainan Island, China. Their structures were elucidated on the basis of spectroscopic analysis and chemical evidence.
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