Estrogenic Activity of Stilbene Derivatives
スポンサーリンク
概要
- 論文の詳細を見る
We previously reported that trans-stilbene is metabolically activated to estrogenic compounds by a liver microsomal enzyme system. In this study, we demonstrated the structural requirement for estrogenic activity of various stilbene derivatives including proestrogens. High estrogenic activity in 4, 4'-dihydroxystilbene, 4-amino-4'-hydroxystilbene, 4, 4'-dihydroxy-α-methylstilbene, hexestrol, and diethylstilbestrol (DES), moderate activity in 4-hydroxystilbene, 4-aminostilbene, 4-hydroxyazobenzene, and 4-hydroxy-4'-nitrostilbene, low activity in 4-nitrostilbene, 4, 4'-dihydroxydibenzyl, resveratrol, and 4-hydroxy-α-methylstyrene, and marginal activity in 4, 4'-dimethoxystilbene and 4-hydroxymethylstilbene were observed in an estrogen reporter assay using the estrogen-responsive human breast cancer cell line MCF-7 and a binding assay with rat uterus estrogen receptor. In contrast, α-methylstilbene, 4, 4'-dimethoxystilbene, 4-hydroxymethylstilbene, dibenzyl, tolan and azobenzene also exhibited estrogenic activities after incubation with liver microsomes of 3-methylcholanthrene- or phenobarbital-treated rats in the presence of NADPH. These results suggest that the structural requirements for the estrogenic activities of stilbene derivatives are a p-hydroxyl group in the A-phenyl ring, vinyl linkage, and a B-phenyl ring for the maximal activity, and hydrophobicity of the linkage for higher activity as observed in DES. p-Nitro and amino groups in the A-phenyl ring are also effective for the estrogenic activity.
- 公益社団法人日本薬学会の論文
- 2003-10-01
著者
-
OHTA Shigeru
Graduate School of Biomedical Sciences, Hiroshima University
-
FURUNO Nobuaki
Institute for Amphibian Biology, Graduate School of Science, Hiroshima University
-
Shigeyuki Kitamura
Nihon Pharmaceutical University
-
Kitamura Shigeyuki
広島大学 医学部総合薬学科生体機能分子動態学
-
Kitamura Shigeyuki
広島大学 総合薬
-
KITAMURA Shigeyuki
Graduate School of Biomedical Science, Hiroshima University
-
Furuno Nobuaki
Institute For Amphibian Biology Graduate School Of Science Hiroshima University
-
Sanoh Seigo
Graduate School Of Biomedical Sciences Hiroshima University
-
Sugihara Kazumi
Graduate School of Biomedical Sciences, Hiroshima University
-
Sugihara K
Graduate School Of Biomedical Sciences Hiroshima University
-
Fujimoto Nariaki
Research Institute For Radiation Biology And Medicine Hiroshima University
-
Ohta S
Graduate School Of Biomedical Sciences Hiroshima University
-
Kitamura Shigeyuki
Institute Of Pharmaceutical Science. Hiroshima University School Of Medicine
-
Fujimoto N
Research Institute For Radiation Biology And Medicine Hiroshima University
-
Ohta Shigeru
Graduate School Of Biomedical Sciences Hiroshima Univ.
-
Kitamura Shigeyuki
Graduate School Of Bioagricultural Sciences Nagoya University
-
SUGIHARA Kazumi
Graduate School of Biomedical and Health Sciences, Hiroshima University
-
SANOH Seigo
Graduate School of Biomedical and Health Sciences, Hiroshima University
関連論文
- Further Metabolism of 2-Formylaminofluorene, a Metabolite of 2-Aminofluorene, in Rats
- Involvement of autophagy via mammalian target of rapamycin (mTOR) inhibition in tributyltin-induced neuronal cell death
- Effects of Strong Static Magnetic Fields on Amphibian Development and Gene Expression
- EFFECT OF A HIGH MAGNETIC FIELD ON AMPHIBIANS(Developmental Biology,Abstracts of papers presented at the 76^ Annual Meeting of the Zoological Society of Japan)
- Spontaneous Tumors in Hypocatalasemic C3H/C^b_s/Gen and C3H Mice
- ROLE OF MAMMALIAN TISSUES AND INTESTINAL BACTERIA IN N-ACYLATION
- N-ACYLATION OF ARYLAMINES IN DOGS
- Protein disulfide isomerase knockdown-induced cell death is cell-line-dependent and involves apoptosis in MCF-7 cells
- Disruption of Thyroid Hormone Function by Environmental Pollutants
- The effect of hypergravity on bipolar spindle formation of meiosis II in Xenopus oocytes
- Effects of Hypergravity on Pituitary-Target Organs in the Frog, Xenopus laevis
- Effects of hypergravity on oocyte maturation in Xenopus laevis
- Effects of Stilbene and Related Compounds on Reproductive Organs in B6C3F1/Crj Mouse
- Interconversion between Fenthion and Fenthion Sulfoxide in Goldfish, Carassius auratus
- Effect of Fenthion on the Level of Vitellogenin in Goldfish, Carassius auratus
- Reductive Dechlorination of p, p'-DDT Mediated by Hemoproteins in the Hepatopancreas and Blood of Goldfish, Carassius auratus
- A biophysical estimate of radioactive iodine (^I) exposure in the whole body and in the thyroid of newborn, puberty and adult Fischer 344 rats.
- Metabolism of Nitropolycyclic Aromatic Hydrocarbons in Animals, Fish and Intestinal Bacteria (Proceedings of the 18th Symposium on Toxicology, and Environmental Health)
- Role of Mammalian Enzymes and Intestinal Bacteria in the Metabolism of Nitropolycyclic Aromatic Hydrocarbons (Proceedings of the 16 th Symposium on Environmental Pollutants and Toxicology)
- Metabolism of Carcinogenic Arylamines : N-Acylation (Proceedings of the 14th Symposium on Environmental Pollutants and Toxicology)
- Metabolism of Nicotine Related Compounds. Reduction of Nicotine-1'-N-oxide. (Proceedings of the 19th Symposium on Toxicology and Environmental Health)
- FUNCTION OF CATALASE AS A N-OXIDES REDUCTASE
- ROLE OF LIVER ALDEHYDE OXIDASE IN DRUG REDUCTION
- Studies on the Metabolism of Nitropolycyclic Aromatic Hydrocarbons (Regular Presentations) (Proceedings of the 11 th Symposium on Environmental Pollutants and Toxicology)
- INVOLVEMENT OF LIVER ALDEHYDE OXIDASE IN CONVERSION OF N-HYDROXYURETHANE TO URETHANE
- Affinity for Thyroid Hormone and Estrogen Receptors of Hydroxylated Polybrominated Diphenyl Ethers
- Metabolic Activation of Proestrogens in the Environment by Cytochrome P450 System
- Effects of Environmental Antiandrogenic Chemicals on Expression of Androgen-Responsive Genes in Rat Prostate Lobes
- Quantitative Determination of Lobe Specificity of mRNA Expression of Androgen-dependent Genes in the Rat Prostate Gland
- Estrogen enhancement of androgen-responsive gene expression in hormone-induced hyperplasia in the ventral prostate of F344 rats
- Estrogenic Activity of Stilbene Derivatives
- Metabolic Activation of Proestrogenic Diphenyl and Related Compounds by Rat Liver Microsomes
- Strain Difference in Regulation of Pituitary Tumor Transforming Gene (PTTG) in Estrogen-induced Pituitary Tumorigenesis in Rats
- Establishment of an Estrogen Responsive Rat Pituitary Cell Sub-Line MtT/E-2
- Growth Stimulation of a Rat Pituitary Cell Line MtT/E-2 by Environmental Estrogens in vitro and in vivo
- DOSE-THRESHOLD FOR THYROID TUMOR-PROMOTING EFFECTS OF ORALLY AMINISTERED KOJIC ACID IN RATS AFTER INITIATION WITH N-bis(2-HYDROXYPROPYL) NITROSAMINE
- Age-dependent Exposure to Radioactive Iodine (^I) in the Thyroid and Total Body of Newborn, Pubertal and Adult Fischer 344 Rats
- Biophysical Estimation of 131I Absorbed Doses and Changes in Plasma Free T3 and TSH After an ^I Injection in Newborn, Puberty and Adult Rats
- ヒト肝細胞を有するキメラマウスを用いた S-^3H-warfarin のヒト体内動態の予測
- Effects of Endocrine Disrupting Chemicals on Amphibian Metamorphosis and Mitochondrial Membrane Permeability Transition
- Novel Metabolic Pathways of p-n-Nonylphenol Catalyzed by Cytochrome P450 and Estrogen Receptor Binding Activity of New Metabolites
- 抗腫瘍剤の代謝酵素であるアルデヒドオキシダーゼは, 生まれたての小児には備わっていない
- In vivo-In vitro Relationship of Methotrexate 7-Hydroxylation by Aldehyde Oxidase in Four Different Strain Rats
- Effect of Green Tea Beverages on Efficacy of Povidone-lodine
- Drug-Metabolizing Ability of Molybdenum Hydroxylases
- Suppression of Amphibian Metamorphosis by Bisphenol A and Related Chemical Substances
- SUPPRESSION OF THYROID HORMONE-INDUCED TADPOLE TAIL APOPTOSIS BY BISPHENOL A AND RELATED CHEMICAL SUBSTANCES(Endocrinology,Abstracts of papers presented at the 75^ Annual Meeting of the Zoological Society of Japan)
- Deacylation of N-Formylanilines and N-Acetylanilines by Rat Liver Formamidase
- Cytochrome P450 1A1/2 Mediated Metabolism of trans-Stilbene in Rats and Humans
- Parkinsonism-Preventing Activity of 1-Methyl-1,2,3,4-tetrahydroisoquinoline Derivatives in C57BL Mouse in Vivo(Pharmacology)
- Detection and determination of reticuline and N-methylcoculaurine in the Annonaceae family using liquid chromatography-tandem mass spectrometry
- Preparative Monohydroxyflavanone Syntheses and a Protocol for Gas Chromatography-Mass Spectrometry Analysis of Monohydroxyflavanones
- Synthesis of Deuterium-Labeled Flavanones
- Extremely High Drug-Reductase Activity Based on Aldehyde Oxidase in Monkey Liver
- Nonenzymatic Reduction of N-Hydroxy-2-acetylaminofluorene to 2-Acetylaminofluorene by Heme in the presence of Hydroquinones
- Effects of High Gravity on Amphibian Development
- Conversion of Dieldrin to Aldrin by Intestinal Bacteria in Rats
- SUPPRESSION OF T_3-INDUCED TADPOLE TAIL ATROPHY BY PARA-NONYLPHENOL(Endocrinology,Abstracts of papers presented at the 74^ Annual Meeting of the Zoological Society of Japan)
- Reductive Metabolism of Stilbene Oxide and Styrene Oxide to the Olefins in Rats
- Quinone-Dependent Tertiary Amine N-Oxide Reduction in Rat Blood
- Studies on the Reductive Metabolism of Olefin Oxides (Proceedings of the 22nd Symposium on Toxicology and Environmental Health)
- Temporal changes in humic acids in cultivated soils with continuous manure application(Soil Chemistry and Soil Mineralogy)
- A Candidate Anti-Prion Disease Agent, 2,2-Biquinoline, Decreases Expression of Prion Protein and mRNA in Prion-Infected Cells
- HIGH GRAVITY INHIBITS EMBRYONIC DEVELOPMENT OF AMPHIBIANS(Developmental Biology,Abstracts of papers presented at the 76^ Annual Meeting of the Zoological Society of Japan)
- THE EFFECT OF HIGH GRAVITY ON AMPHIBIAN DEVELOPMENT(Developmental Biology,Abstracts of papers presented at the 75^ Annual Meeting of the Zoological Society of Japan)
- Studies on Reductive Metabolism of Aromatic Nitro Compounds (Proceedings of the 12 th Symposium on Environmental Pollutants and Toxicology) (Regular Presentations)
- A New Mechanism for Reduction of Carcinogenic Hydroxamic Acids
- A COMPARATIVE STUDY ON 1-NITROPYRENE AND NITROFURAZONE REDUCTASES IN ESCHERICHIA COLI
- Enzymes Responsible for Reduction of Nitropolycyclic Aromatic Hydrocarbons (Regular Presentations) (Proceedings of the 10 th Symposium on Environmental Pollutants and Toxicology)
- STUDIES ON BACTERIAL NITROREDUCTASES. ENZYMES INVOLVED IN REDUCTION OF AROMATIC NITRO COMPOUNDS IN ESCHERICHIA COLI
- Protein disulfide isomerase knockdown-induced cell death is cell-line-dependent and involves apoptosis in MCF-7 cells
- DT-Diaphorase-Like Quinone Reductase in Rat Plasma
- Activation of Morphine Glucuronidation by Fatty Acyl-CoAs and Its Plasticity : A Comparative Study in Humans and Rodents Including Chimeric Mice Carrying Human Liver
- Syntheses and Glycosidase Inhibiting Activities of Nagstatin Analogs
- Profiling of Illegal Amphetamine-type Stimulant Tablets in Japan
- Effects of Strong Static Magnetic Fields on Amphibian Development and Gene Expression
- Induction of Xanthine Dehydrogenase by TCDD(PROCEEDINGS OF 24TH SYMPOSIUM ON TOXICOLOGY AND ENVIRONMENTAL HEALTH)
- Lack of the Consensus Sequence Necessary for Tryptophan Prenylation in the ComX Pheromone Precursor