Anti-Estrogenic Activity of Prenylated Isoflavones from Millettia pachycarpa : Implications for Pharmacophores and Unique Mechanisms

スポンサーリンク

概要

• 論文の詳細を見る

• Phytoestrogens containing isoflavonoids are thought to exhibit preventative effects on estrogen-responsive diseases. Chemical modifications, such as prenylation, in biosynthetic processes enhance the structural variety of isoflavonoids and prompted us to carry out a structure-activity relationship study. We determined the estrogenic/anti-estrogenic activities and estrogen receptor (ER)-binding affinities of eight kinds of prenylated isoflavones isolated from Millettia pachycarpa (Leguminosae), and those of two kinds of non-prenylated compounds (genistein and daidzein). By comparing these compounds, the pharmacophores for estrogenic/anti-estrogenic activities were elucidated. None of the tested compounds (except genistein) were estrogenic on ligand-dependent yeast-two hybrid assay. On the other hand, 5 isoflavones showed distinct anti-estrogenic activity. Unexpectedly, the most potent antagonists, isoerysenegalensein E and 6,8-diprenylorobol, showed anti-estrogenic activity comparable to that of 4-hydroxytamoxifen, a typical ER antagonist. This suggests that genistein became an antagonist after prenylation and hydroxylation. The pharmacophores providing genistein with strong antiestrogenic activity were as follows: prenyl groups of the 6- and 8-positions on the A-ring, hydroxyl group of the 6-prenyl moiety or the B-ring (catechol form), non-cyclization of the prenyl group with the A-ring, and non-hydroxylation of the 8-prenyl group on the A-ring. The ER-binding affinities of the isoflavonoids were not sufficiently high to explain their potent antagonistic activities, thus suggesting 17β-estradiol-noncompetitive mechanisms.

• 公益社団法人日本薬学会の論文
• 2006-04-01

著者

• ITO Chihiro

  Faculty of Pharmacy, Meijo University

• FURUKAWA Hiroshi

  Faculty of Pharmacy, Meijo University

• Ueda Koji

  Faculty of Pharmacy, Meijo University

• Okamoto Yoshinori

  Faculty of Pharmacy, Meijo University

• Kojima Nakao

  Faculty of Pharmacy, Meijo University

• Ito Chihiro

  Faculty Of Pharmacy Meijo University

• SUZUKI Atsushi

  Faculty of Pharmaceutical Sciences, Hokkaido University

• Suzuki Atsushi

  Faculty Of Bioindustry Tokyo University Of Agriculture

• Suzuki Atsushi

  Faculty Of Pharmacy Meijo University

• Furukawa Hiroshi

  Faculty Of Pharmacy Meijo University

• Kojima Nakao

  Exploratory Medicinal Sciences Pfizer Global Research And Development(pgrd)-nagoya Laboratories Pfiz

• Kojima Nakao

  Faculty Of Pharmacy Meijo University

• Kojima Nakao

  Central Research Division Pfizer Pharmaceuticals Inc.

• ITOIGAWA Masataka

  Faculty of Human Wellness, Tokaigakuen University

• Nishihara Tsutomu

  Center for Advanced Science and Innovation, Osaka University

• Itoigawa Masataka

  Faculty Of Human Wellness Tokai Gakuen University

• Okamoto Yoshinori

  Fac. Of Pharmacy Meijo Univ.

• Nishihara Tsutomu

  Center For Advanced Science And Innovation Osaka University

• Furukawa Hiroshi

  Faculty Of Computer Science And Systems Engineering Kyushu Institute Of Technology

• UEDA Koji

  Faculty of Agriculture, Yamagata University

• Suzuki Atsushi

  Faculty of Agriculture, Niigata University

• Kojima Nakao

  Faculty of Pharmaceutical Sciences, Kyoto University

関連論文

• In Vitro Absorption and Metabolism of Nobiletin, a Chemopreventive Polymethoxyflavonoid in Citrus Fruits
• Preparation of oligoselenodiglutathiones and their suppressive effects on oxidative DNA damage induced by catechol and copper
• Two New Dimeric Coumarins Isolated from Murraya exotica
• Preparation of Oligoselenodiglutathiones and Their Suppressive Effects on Oxidative DNA Damage Induced by Catechol and Copper
• A Novel Depsidone and Some New Xanthones from Garcinia species
• A Novel Dibenzofuran and Two New Xanthones form Calophyllum panciflorum
• Chemical Constituents of Glycosmis pentaphylla. Isolation of A Novel Naphthoquinone and A New Acridone Alkaloid
• New Pyrrolizidinone Antibiotics CJ-16,264 and CJ-16,367
• Bone morphogenetic protein acts as a ventral mesoderm modifier in early Xenopus embryos
• A New Antibiotic CJ-17,665 from Aspergillus ochraceus
• CJ-15,208, a Novel Kappa Opioid Receptor Antagonist from a Funguns, Ctenomyces serratus ATCC15502
• CJ-15,696 and Its Analogs, New Furopyridine Antibiotics from the Fungus Cladobotryum varium : Fermentation, Isolation, Structural Elucidation, Biotransformation and Antibacterial Activities
• Cytokine Production Inhibitors Produced by a Fungus, Oidiodendron griseum
• Novel Cytokine Production Inhibitors Produced by a Basidiomycete, Marasmiellus sp.
• P-164 Novel Acridone-Flavanone Dimers from Citrus Plants (Rutaceae)
• Two New Dimeric Acridone Alkaloids from Glycosmis citrifolia
• Isolation and Identification of Two New Flavanones and a Chalcone from Citrus kinokuni^
• Four New Furanone-Coumarins from Clausena excavata
• Chemical Constituents of Avicennia alba. Isolation and Structural Elucidation of New Naphthoquinones and Their Analogues
• Chemical Constituents of Micromelum minutum. Isolation and Structural Elucidation of New Coumarins
• Chemical Constituents of Glycosmis citrifolia (WILLD.) LINDL.Structures of Four New Acridones and Three New Quinolone Alkaloids
• New Quinazoline Alkaloids from Glycosmis cochinchinensis
• Four New Acridone-Coumarin Dimers from a Citrus Plant
• A New Dimeric Acridone Alkaloid from Citrus paradisi MACF
• Structures of Clausamine-A, -B, -C, Three Novel Carbazole Alkaloids from Clausena anisata
• CJ-13,981 and CJ-13,982, New Squalene Synthase Inhibitors
• New Quinolone Compounds from Pseudonocardia sp. with Selective and Potent Anti-Helicobacter pylori Activity: Taxonomy of Producing Strain, Fermentation, Isolation, Structural Elucidation and Biological Activities
• CJ-12, 373, a Novel Topoisomerase II Inhibitor: Fermentation, Isolaton, Atructure Elucidation and Biological Activities
• Novel Lactone Compounds from Mortierella verticillata that Induce the Human Low Density Lipoprotein Receptor Gene: Fermentation, Isolation, Structural Elucidation and Biological Activities
• CJ-12, 954 and Its Congeners, New Abti-Helicobacter pylori Compounds Produced by Phanerochaete velutina: Fermentation, Isolation, Structural Elucidation and Biological Activities
• Generation of Novel Rapamycin Structures by Microbial Manipulations
• CJ-12, 371 and CJ-12, 372, Two Novel DNA Gyrase Inhibitors Fermentation, Isolation, Structural Elucidation and Biological Activities
• Thielavins as Glucose-6-phosphatase (G6Pase) Inhibitors : Producing Strain, Fermentation, Isolation, Structural Elucidation and Biological Activities
• Erinacine E as a Kappa Opioid Receptor Agonist and Its New Analogs from a Basidiomycete, Hericium ramosum
• Regulation of Tumor Necrosis Factor-α Production by a Fungal Metabolite, PR 1388
• CJ-15,183, a New Inhibitor of Squalene Synthase Produced by a Fungus, Aspergillus aculeatus
• Production of Polyselenodipenicillamines, Unique Selenium Compounds
• Involvement of DNA Conformational Change Induced by Rearrangement of Copper-coordination Geometry in Oxidative DNA Damages Caused by Copper and Dopamine
• Formation of DNA Damaging Product from Light-Irradiated Nonylphenol
• Novel Estrogenic Microsomal Metabolites from Phthalate Esters
• Phthalate Esters Detected in Various Water Samples and Biodegradation of the Phthalates by Microbes Isolated from River Water
• Erinacines E, F, and G, Stimulators of Nerve Growth Factor (NGF)-Synthesis, from the Mycelia of Hericium erinaceum.
• Studies on the Constituents of Yalaha. Structures of a New Acridone Alkaloid and Two New Coumarins
• The Structures of Claudimerines-A and -B, Novel Bicoumarins from Citrus hassaku
• Measurement of Strain in an Elastic Plate Due to Impulsive Pressure
• Evaluation of Flavoglaucin, Its Derivatives and Pyranonigrins Produced by Molds Used in Fermented Foods for Inhibiting Tumor Promotion
• Antioxidants Produced by Eurotium herbariorum of Filamentous Fungi Used for the Manufacture of Karebushi, Dried Bonito (Katsuobushi)
• Antioxidative Pyranonigrins in Rice Mold Starters and Their Suppressive Effect on the Expression of Blood Adhesion Molecules
• Isolation of the Antioxidant Pyranonigrin-A from Rice Mold Starters Used in the Manufacturing Process of Fermented Foods
• Constituents of Clausena excavata. Isolation and Structural Elucidation of New Carbazole Alkaloids
• Constituents of Clausena excavata. Isolation and Structural Elucidation of Seven New Carbazole Alkaloids and a New Coumarin
• Pattern Formations in Unstable Network : Model for Cross-Linked Polymer Chains
• Grain Growth by Inhomogeneous Quenching : Numerical Simulation in three Dimensions : Condensed Matter and Statistical Physics
• Ordering Dynamics with Moving Plane Boundary between Ordered and Disordered Phases : Condensed Matter and Statistical Physics
• Structures of Lansiumarin-A, -B, -C, Three New Furocoumarins from Clausena lansium
• Combined Effects of Manganese, Iron, Copper, and Dopamine on Oxidative DNA Damage
• Anti-Estrogenic Activity of Prenylated Isoflavones from Millettia pachycarpa : Implications for Pharmacophores and Unique Mechanisms
• Transesterification in the Microbial Degradation of Phthalate Esters
• Effects of Prenatal Administration of Phencyclidine on the Learning and Memory Processes of Rat Offspring
• Physical Fitness and Exercise Endurance Measured by Oxygen Uptake Kinetics in Stroke Patients
• Peroxynitrite Scavengers Produced by Filamentous Fungus Used in the Katsuobushi Manufacturing Process
• Evaluation of Flavoglaucin, Its Derivatives and Pyranonigrins Produced by Molds Used in Fermented Foods for Inhibiting Tumor Promotion
• Antioxidants Produced by Eurotium herbariorum of Filamentous Fungi Used for the Manufacture of Karebushi, Dried Bonito (Katsuobushi)
• Antioxidative Pyranonigrins in Rice Mold Starters and Their Suppressive Effect on the Expression of Blood Adhesion Molecules
• Isolation of the Antioxidant Pyranonigrin-A from Rice Mold Starters Used in the Manufacturing Process of Fermented Foods
• Influence of Walking Speed Change and the Swing Phase Adjustment of the Intelligent Prosthesis Users on the Intact Limb
• Characteristics of Biceps femoris and Longissimus thoracis muscles of five cattle breeds grown in a feedlot system
• A Controlled Synthesis of 9α-Methyl- and 9α-Cyanoisocarbacyclins
• A Controlled Synthesis of 9α-Methyl- and 9α-Cyanoisocarbacyclins
• Recyclable Polymeric π-Acid Catalyst Effective on Mannich-Type Reaction in Water
• Comparative karyological studies and distribution of nucleolus organizer regions (NORs) in five species in cyprinoid fishes(Abstracts of the 49th Annual Meeting of the Society of Chromosome Research)
• Tunneling Study in Ag-SiO-Bi_2Sr_2CaCu_2O_8_x Planer Junctions Fabricated on Single Crystal and Polycrystal
• Signal Strength Prediction and Distribution Characteristics in Indoor Radio Propagation at 2.5 GHz Band (Special Issue on Personal, Indoor and Mobile Radio Communications)
• Secondary Metabolites in the Peel of Citrus tachibana
• P-13. Chromosomal and molecular genetic studies of five species in the family Osteoglossidae : Order Osteoglossiformes, Pisces(Abstracts of the oral and poster presentations,Abstracts of the 55th Annual Meeting of the Society of Chromosome Research)
• Polymethoxyflavonoids from the Peel of Citrus Jabara
• Potential Risks of Phthalate Esters : Acquisition of Endocrine-disrupting Activity during Environmental and Metabolic Processing
• Crack Propagation Velocities in Chain Model in Two and Three Dimensions
• The Structure of the Velocity Field in a Phase-Separating Turbulent Fluid Mixture
• Propagation and Pattern of Crack in Two Dimensional Dynamical Lattice : Condensed Matter and Statistical Physics
• A GENERAL METHOD FOR DETERMINING ABSOLUTE CONFIGURATIONS OF ACYCLIC 1,3-POLYOLS
• Leaf herbivory by Spodoptera litura increases arbuscular mycorrhizal colonization in roots of soybean(Soil biology)
• Reynolds Number in Phase Ordering Fluid Systems
• Asymptotic Behavior of Structure Function at Small Wave Numbers in Late Stage of Phase Separation : Complex Dynamics in Nonlinear Systems
• Potential Risks of Phthalate Esters: Acquisition of Endocrine-disrupting Activity during Environmental and Metabolic Processing
• 1/f Spectrum of Quasi-Random Objects
• Narrowings of Structure Function of Phase Separating Unmixing-Mixture
• The complexing of indium(III) by cysteine: evidence for sulfurbridged and protonated complexes.
• Leaf herbivory by Spodoptera litura increases arbuscular mycorrhizal colonization in roots of soybean

もっと見る 閉じる

スポンサーリンク