Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 57, Issue 8
Displaying 1-23 of 23 articles from this issue
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Review
  • Naturally Occurring Iridoids, Secoiridoids and Their Bioactivity. An Updated Review, Part 3
    Biswanath Dinda, Debashis Roy Chowdhury, Bikas Chandra Mohanta
    Article type: Review
    2009 Volume 57 Issue 8 Pages 765-796
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.765
    JOURNAL FREE ACCESS
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    Naturally occurring new iridoids and secoiridoids published during 2005—2008 are reviewed with available physical and spectral data: mp, [α]D, UV, IR, 1H- and 13C-NMR and plant source. The works on biological and pharmacological activity of naturally occurring iridoids and secoiridoids reported during 2005—2008 are also reviewed. Bioactivities like antibacterial, anticancer, anticoagulant, antifungal, anti-inflammatory, antioxidative, antiprotozoal, hepatoprotective and neuroprotective activities are highlighted.
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Regular Articles
  • Anti Human Immunodeficiency Virus-1 (HIV-1) Agents 3. Synthesis and in Vitro Anti-HIV-1 Activity of Some N-Arylsulfonylindoles
    Ling-Ling Fan, Wu-Qing Liu, Hui Xu, Liu-Meng Yang, Min Lv, Yong-Tang Z ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 797-800
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.797
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    In order to find compounds with superior anti human immunodeficiency virus type 1 (HIV-1) activity, twelve simple N-arylsulfonylindoles (3a—l) were synthesized and preliminarily evaluated as HIV-1 inhibitors in vitro for the first time. Several compounds demonstrated significant anti-HIV-1 activity, especially N-(3-nitrobenzene)sulfonyl-6-methylindole (3h) and N-(3-nitrobenzene)sulfonylindole (3i) showed the highest anti-HIV-1 activity with EC50 values of 0.26 and 0.74 μg/ml, and TI values of 543.78 and >270.27, respectively.
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  • Structure–Analgesic Activity Relationship Studies on the C18- and C19-Diterpenoid Alkaloids
    Jian-Li Wang, Xiang-Li Shen, Qiao-Hong Chen, Gong Qi, Wei Wang, Feng-P ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 801-807
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.801
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    For evaluation of C18- and C19-diterpenoid alkaloids as analgesics, three C19-diterpenoid alkaloids were isolated from the roots of Aconitum hemsleyanum var. circinatum and A. transsecutum; and twenty-five semisynthetic C18- or C19-diterpenoid alkaloids were prepared from lappaconitine, crassicauline A or yunaconitine. In a mice acetic acid-induced abdominal constriction assay, four crassicauline A analogs and three yunaconitine analogs exhibited good analgesic activities with 77.8—94.1% inhibition range in 0.1—10 mg/kg subcutaneous (s.c.) dose range at the point of 20 min after drug administration. Among them, 8-O-deacetyl-8-O-ethylcrassicauline A (ED50=0.0972 mg/kg) and 8-O-ethylyunaconitine (ED50=0.0591 mg/kg) were the most potent analgesics relative to the reference drugs lappaconitine (ED50=3.50 mg/kg) and crassicauline A (ED50=0.0480 mg/kg). Analgesic activity data of these C18- and C19-diterpenoid alkaloids indicate that a tertiary amine in ring A, an acetoxyl or an ethoxyl group at C-8, an aromatic ester at C-14, and the saturation state of the ring D are important structural features necessary to the analgesic activity of the C19-diterpenoid alkaloids.
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  • Cytotoxic Activity and DNA-Binding Investigations of Two Benzoxanthone Derivatives
    Hui-Fang Wang, Rui Shen, Lei Jia, Jin-Cai Wu, Ning Tang
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 808-813
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.808
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    In this study, the interactions of two benzoxanthones 1,3-dihydroxy-12H-benzo[b]xanthen-12-one (1) and 9,11-dihydroxy-12H-benzo[a]xanthen-12-one (2) with calf thymus DNA (ct DNA) have been investigated by absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy and viscosity measurements. Experimental results suggested an intercalative mode with DNA for the two compounds; Furthermore, the binding affinity with DNA of 1 bearing linearly fused aromatic rings was higher than that of 2 bearing angularly fused aromatic rings according to the calculated binding constant values. In addition, three cell lines, the human cervical cancer cell line (HeLa), human hepatocellular liver carcinoma cell line (HepG2) and human normal liver cell line (L02) were used to evaluate the cytotoxic activities of the two benzoxanthones in vitro. As the results, they showed significant cytotoxic activity against the tumor cell lines HeLa and HepG2, but weak cytotoxic activity against normal liver cell line L02.
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  • Antitumor Activity and DNA-Binding Investigations of the Zn(II) and Cu(II) Complexes with Isoeuxanthone
    Huifang Wang, Rui Shen, Jincai Wu, Ning Tang
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 814-818
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.814
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    Two new complexes ZnL2 (1) and CuL2 (2) (here, HL=isoeuxanthone) have been synthesized and characterized by elemental analyses, molar conductance, infrared spectra (IR), 1H-NMR and UV–Vis measurements. The interactions of them with calf thymus DNA (ct DNA) have been investigated by absorption spectroscopy, fluorescence spectroscopy, circular dichroism spectroscopy and viscosity measurements. Experimental results revealed an intercalative interaction with DNA for the complexes; furthermore the binding affinity of 2 is higher than that of 1 according to the calculated binding constant values. In addition, they were evaluated for their cytotoxic activities toward human esophageal cancer (ECA109) and human gastric cancer (SGC7901) cells by MTT assay. Both of them showed significant cytotoxic potency.
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  • Improved Microwave-Mediated Synthesis of 3-(3-Aryl-1,2,4-oxadiazol-5-yl)propionic Acids and Their Larvicidal and Fungal Growth Inhibitory Properties
    Ricardo Antonio Wanderley Neves Filho, Cecília Aguiar da Silva, ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 819-825
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.819
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    The synthesis of 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids from arylamidoximes and succinic anhydride under focused microwave irradiation conditions is described. The new synthetic method furnished the desired products in 2—3 min and good yields. Furthermore, the previously complicated purification procedure has been simplified in a manner which is quick, eco-friendly and cost-effective. Larvicidal bioassay and fungal growth inhibitory tests were performed using several 3-(3-aryl-1,2,4-oxadiazol-5-yl)propionic acids. These acids presented strong larvicidal activity against L4 larvae of Aedes aegypti. The results suggest that larvicidal activity might be correlated with the presence of electron-withdrawing substituents in the para position of the phenyl ring except the fluorine atom. The alterations observed in the larvae spiracular valves of the siphon and anal papillae by 1,2,4-oxadiazoles in the larvicidal bioassay are responsible for larvae's death. Furthermore, all acids inhibited the fungal growth of five different types of fungi, viz., Fusarium solani, F. oxysporum, F. moniliforme, F. decemcellulare and F. lateritium in a preliminary evaluation. Both of these activities are being disclosed for the first time for 1,2,4-oxadiazole-5-yl ring linked at C-3 of propionic acid.
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  • Synthesis and Biological Evaluation of a New Set of Pyrazolo[1,5-c]quinazolines as Glycine/N-Methyl-D-aspartic Acid Receptor Antagonists
    Flavia Varano, Daniela Catarzi, Vittoria Colotta, Daniela Poli, Guido ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 826-829
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.826
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    Previous studies have shown that 8-chloro-5,6-dihydro-5-oxo-pyrazolo[1,5-c]quinazoline-2-carboxylates (PQZ series) represent a family of glycine/N-methyl-D-aspartic acid (NMDA) and/or (R,S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) and/or kainic acid (KA) receptor antagonists. Moreover, some groups have been identified that introduced in suitable positions of the PQZ 2-carboxylate framework shift affinity and selectivity toward glycine/NMDA receptor. These substituents are a carboxylate function at position-1 and/or a chlorine atom at position-9. In this paper we report a study on some new 5,6-dihydro-5-oxo-pyrazolo[1,5-c]quinazoline-1-carboxylates bearing at position-2 a lipophilic amide group or lacking substituent at this same position. All the newly synthesised compounds were evaluated for their binding at glycine/NMDA, AMPA and KA receptors. These studies led to the identification of some new PQZ derivatives endowed with good glycine/NMDA receptor affinity and selectivity and to better definition of the structure–activity relationship (SAR) of this class of compounds.
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  • Cytotoxic Geranylated Xanthones and O-Alkylated Derivatives of α-Mangostin
    Ly Dieu Ha, Poul Erik Hansen, Ole Vang, Fritz Duus, Hung Dinh Pham, Li ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 830-834
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.830
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    Two new geranylated xanthones, 6-O-methylcowanin (4) and oliverixanthone (5), along with five known compounds, cowanin, rubraxanthone, cowaxanthone, cowanol, and β-mangostin, have been isolated from the bark of Garcinia oliveri. For comparison of their biological activities, one mono- and seven di-O-alkylated α-mangostin derivatives were synthesized from α-mangostin. The structures of all compounds were assigned by spectroscopic methods (1D and 2D NMR and MS). Cytotoxicity of selected xanthones against MCF-7 and DLD-1 cell lines was examined. Evaluation of the structure–activity relationship showed that α-mangostin had the strongest activity, and all the O-alkylated α-mangostin derivatives showed reduced activity compared to the naturally occurring α-mangostin.
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  • Structure Elucidation of Major Metabolites from Medroxyprogesterone Acetate by P450
    Jianjun Chen, Jiang-Wei Zhang, Ling Yang, Wei Li
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 835-839
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.835
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    We previously reported the separation and identification for the major metabolites from incubating medroxyprogesterone acetate (MPA) with P450. The structure assignments for these metabolites were tentatively assigned based on one-dimensional (1D) proton NMR. Unambiguous structure identification of these metabolites is critical to study biological pathways of P450. Here we report the complete structure elucidation by extensive two-dimensional (2D) NMR for the three major metabolites isolated in our earlier studies. The three major metabolites (namely M-2, M-3, M-4) were unambiguously identified to be 6β-, 1β-, and 2β-hydroxy MPA. The current work confirmed the speculated structures for these metabolites in our previous studies. More importantly, the unambiguous structural information and the establishment for their NMR chemical shifts of these metabolites can serve as reference standards for future studies.
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  • Supinaionosides A and B: Megastigmane Glucosides and Supinanitrilosides A—F: Hydroxynitrile Glucosides from the Whole Plants of Euphorbia supina RAFINESQUE
    Wen-Hu Cai, Katsuyoshi Matsunami, Hideaki Otsuka
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 840-845
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.840
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    From whole plants of Euphorbia supina, two new megastigmane glucosides, named supinaionosides A and B (1, 2), six new hydroxynitrile glucosides, named supinanitrilosides A—F (3—8), and six known compounds were isolated. The structures of the new compounds were elucidated on the basis of spectroscopic and chemical evidence.
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  • Chemical Reactivity of Dihydropyrazine Derivatives. Cycloaddition Behavior toward Ketenes
    Kazuhide Nakahara, Koki Yamaguchi, Yasuyuki Yoshitake, Tadatoshi Yamag ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 846-852
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.846
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    The cycloaddition behavior of dihydropyrazines toward ketenes was investigated using single-crystal X-ray structures of the cycloadducts and density functional theory (DFT) calculation data. The reaction proceeds via a stepwise pathway involving an orientation complex prior to formation of the betaine intermediate. This is followed by electrocyclization to afford the 1 : 1 and 1 : 2 adducts bearing β-lactam ring(s).
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  • Medicinal Flowers. XXX. Eight New Glycosides, Everlastosides F—M, from the Flowers of Helichrysum arenarium
    Toshio Morikawa, Li-Bo Wang, Kiyofumi Ninomiya, Seikou Nakamura, Hisas ...
    Article type: Regular Article
    2009 Volume 57 Issue 8 Pages 853-859
    Published: August 01, 2009
    Released on J-STAGE: August 01, 2009
    DOIhttps://doi.org/10.1248/cpb.57.853
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    Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemical evidence.
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