Metabolism of (+)- and (-)-Menthols by CYP2A6 in Human Liver Microsomes
スポンサーリンク
概要
- 論文の詳細を見る
The in vitro metabolism of (+)-(1S,3S,4R) and (-)-(1R,3R,4S)-menthol enantiomers was examined by incubation with human liver microsomes, and the oxidative metabolites thus formed were analyzed using gas chromatography-mass spectrometry (GC-MS). The (+)- and (-)-menthols were found to be oxidized to the respective (+)-(1S,3S,4S)- and (-)-(1R,3R,4R)-trans-p-menthane-3,8-diol derivatives by human liver microsomal P450 enzymes. Cytochrome P450 (CYP) 2A6 was determined to be the major enzyme involved in the hydroxylation of (+)- and (-)-menthols by human liver microsomes on the basis of the following lines of evidence. First, of 11 recombinant human P450 enzymes tested, CYP2A6 catalyzed the oxidation of (+)- and (-)-menthols. Second, oxidation of (+)- and (-)-menthols was inhibited by (+)-menthofuran and anti-CYP2A6 antibody. Finally, (+)- and (-)-menthol activities were found to correlate with contents of CYP2A6 in liver microsomes of 9 human samples.
著者
-
Takahashi Toshiyuki
Department of Cardiology, JR Tokyo General Hospital
-
MIYAZAWA Mitsuo
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
-
Marumoto Shinsuke
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
-
Nakahashi Hiroshi
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
-
Haigou Risa
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
-
Nakanishi Kyousuke
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
-
Nakanishi Kyousuke
Department Of Applied Chemistry Faculty Of Science And Engineering Kinki University
-
Miyazawa Mitsuo
Department Of Applied Chemistry Faculty Of Scienc Snd Engineering Kinki University
-
Takahashi Toshiyuki
Department Of Biology Keio University
-
Miyazawa Mitsuo
Department Of Aplied Chemistry Faculty Of Science And Engineering Kinki University
-
Takahashi Toshiyuki
Department Of Biological Science Graduate School Of Science Hiroshima University
-
Takahashi Toshiyuki
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University
関連論文
- Postpartum Complete Atrioventricular Block Due to Cardiac Sarcoidosis : Steroid Therapy Without Permanent Pacemaker
- Inhibition of Helicobacter pylori Motility by (+)-Syringaresinol from Unripe Japanese Apricot(Medicinal Chemistry)
- DPE-010 Increased C-reactive Protein Expression Exacerbates Left Ventricular Dysfunction and Remodeling after Myocardial Infarction in Mice(DPE02,Heart Failure, Basic (M),Digital Poster Session (English),The 73rd Annual Scientific Meeting of The Japanese
- PE-221 Intravenous Administration of Immunoglobulin Attenuates Myocardial Reperfusion Injury and Improves Left Ventricular Remodeling(Myocardial ischemia/reperfusion, basic/clinical(03)(IHD),Poster Session(English),The 72nd Annual Scientific Meeting of th
- Relationship between antinuclear antibody and microalbuminuria in the general population : the Takahata study
- Endoscopic pancreatic duct drainage and stenting for acute pancreatitis and pancreatic cyst and abscess
- Establishment of a New Sensitive Assay for Anti-Human Aquaporin-4 Antibody in Neuromyelitis Optica
- Three-vessel Coronary Artery Disease Complicated with Congestive Heart Failure in a Highly Aged Patient with Tetralogy of Fallot Having Undergone Palliative Surgeries
- Metabolism of (+)- and (-)-Menthols by CYP2A6 in Human Liver Microsomes
- Volatile Components of the Straw of Oryza sativa L.
- A Novel Technique to Measure Ca^ Concentration in Sarcoplasmic Reticulum of Cardiomyocytes
- Characteristic Effects of α1-β_1,2-Adrenergic Blocking Agent, Carvedilol, on [Ca^2+]_i in Ventricular Myocytes Compared With Those of Timolol and Atenolol
- Comparison of Larvicidal, Adulticidal and Acaricidal Activity of Two Geometrical Butylidenephthalide Isomers(Pharmacognosy)
- Biotransformation of (-)-Menthone by Human Liver Microsomes
- PE-259 Patients with Constrictive Pericarditis Have Lower Blood Brain Natriuretic Peptide Levels Because They Have Lower Left Ventricular Transmural Filling Pressures(Neurohumoral Factors 2 (H) : PE44)(Poster Session (English))
- PE-255 Blood BMP Levels as a Prognostic Indicator in Patients with Moderate Pericardial Effusion(Neurohumoral Factors 2 (H) : PE44)(Poster Session (English))
- Volatile Flavor Components of ZINGIBERIS RHIZOMA (Zingiber officinale Roscoe)(Organic Chemistry)
- Upregulated Neurohumoral Factors are Associated With Left Ventricular Remodeling and Poor Prognosis in Rats With Monocrotaline-Induced Pulmonary Arterial Hypertension
- Signaling Pathways Responsible for Fetal Gene Expression in the Failing Human Heart- Evidence for Altered Thyroid Hormone Receptor Gene Expression
- Dominant Negative Mutants of Transcriptional Factor AP-1 Dissociates Cardiac Myocyte Hypertrophy and Pathologic Gene Program
- Inhibition of Histone Deacetylase Reverses Repression of Myocyte-Specific Gene Expression Associated with Cardiac Hypertrophy
- Successful electrical cardioversion of atrial fibrillation increases coronary blood flow
- Endothelin-1 facilitates inotropism via Rho kinase-dependent myosin light chain kinase activation in adult rat ventricular myocytes
- Both plasma atrial natriuretic peptide and immediate improvement of left ventricular stroke volume as useful predictors of outcome of cardioversion
- Half disruption of Na/Ca exchanger Gene Increases the [Ca^] Amplitude due to Sarcoplasmic Reticulum Ca^ Overload in Murine Ventricular Myocytes
- Hypertrophic Cardiomyopathy With Midventricular Obstruction and Apical Aneurysm : A Case Report
- Left Ventricular Relaxation Abnormality Is Detectable by Analysis of the Relaxation Time Constant in Patients With Atrial Fibrillation
- IS005 Cell Swelling-induced Increase in Delayed-rectifier K Current is Mediated by Autocrine Release of ATP
- IS011 Evolutionally-conserved role of nuclear factor-κB in expression of inducible nitric oxide synthase gene in ventricular myocytes
- Toxicity and Bioaccumulation of Hexavalent Chromium in Green Paramecium, Paramecium bursaria
- 炭疽病菌による4-propylcyclohexanoneおよび4-isopropylcyclohexanoneの立体選択的還元
- 炭疽病菌による4-tert-butylcyclohexanoneの立体選択的還元
- Essential Oil Constituents of "PAEONIAE RADIX" Peaonia lactiflora Pall. (P. albilora Pall.)
- The Constituents of the Essential Oil from Erigeron philadelphicus
- Convenient Synthesis of Arylmethylenesuccinic Acids via Wittig Reaction
- Character Impact Odorants of Wild Edible Plant-Cacalia hastata L. var. orientalis-Used in Japanese Traditional Food
- Hepatic Metastasis 12 Years after Nephrectomy for Renal Cell Carcinoma
- Inhibitory Compound of Tyrosinase Activity from the Sprout of Polygonum hydropiper L.(Benitade)(Pharmacology)
- Regioselective Oxidation of (+)-α-Longipinene by Aspergillus niger
- Cyclooxygenase-2 inhibitory effects and composition of the volatile oil from the dried roots of Lithospermum erythrorhizon
- Constituents of Essential Oil from the Dried Fruits and Stems of Akebia quinata (THUNB.) DECNE.
- Takayasu Myocarditis Mediated by Cytotoxic T Lymphocytes
- Suppression of the SOS-Inducing Activity of Trp-P-1 and Aflatoxin B_1 by Meso-dihydroguaiaretic Acid from Machilus thunbergii in the Salmonella typhimurium TA1535/pSK1002 umu Test
- g-Factor of Λ in the Hypernuclei Studied from B(M1) Measurement(Proceedings of the YITP Workshop on Nuclear Matter under Extreme Conditions)
- Biotransformation of Sinesetin by the Larvae of the Common Cutworm (Spodoptera litura)(Biochemistry/Molecular Biology)
- α-Glucosidase Inhibitor from Bergenia ligulata
- Antimutagenic Compound from Yellow batai (Peltophorum dasyrachis)
- Components of Essential Oil from Woods of Prunus mume Sieb. et Zucc.
- A Prominent Elevation of Glial Fibrillary Acidic Protein in the Cerebrospinal Fluid during Relapse in Neuromyelitis Optica
- Antimutagenic Activity of Isoflavone from Belamcanda chinensis
- Antimutagenic Activity of Gigantol from Dendrobium nobile
- Antimutagenic Activity of Falcarindiol from Peucedanum praeruptorum
- Antimutagenic Activity of (+)-β-Eudesmol and Paeonol from Dioscorea japonica
- Clinical utility of trace proteinuria for microalbuminuria screening in the general population
- An angiotensin II type-I receptor blocker, olmesartan medoxomil, attenuates lipid peroxidation in renal injury induced by subtotal nephrectomy
- Expression of cyclooxygenase-2 and prostaglandin receptor EP4b mRNA in the ovary of the medaka fish, Oryzias latipes: Possible involvement in ovulation
- Spinal Granulocytic Sarcoma Manifesting as Radiculopathy in a Nonleukemic Patient
- Congestive Myelopathy Due to Cervical Perimedullary Arteriovenous Fistula Evaluated by Apparent Diffusion Coefficient Values : Case Report
- 生殖医学に役立つメダカの排卵研究
- メダカの in vitro 排卵実験系を利用した排卵研究
- Suppression of Chemical Mutagens-Induced SOS Response by Phenolic Acids from Black Rice Bran Using Salmonella typhimurium TA1535/pSK1002 umu Test
- PB113 SYNTHESIS AND BIOLOGICAL ACTIVITY OF β-D-GLUCOPYRANOSIDE OF THE MONOTERPENE ALCOHOLS
- Expression of Bradykinin B_2 Receptor in the Mouse Ovary(Physiology)
- Cloning and Expression in Escherichia coli of the D-Aspartate Oxidase Gene from the Yeast Cryptococcus humicola and Characterization of the Recombinant Enzyme
- Characterization of mouse tissue kallikrein 5
- ANALYSIS OF MEDAKA KALLIKREIN LIKE PROTEIN THE RE PRODUCTIVE ORGANS
- Characterization of Volatile Aroma Compounds from Red and Black Rice Bran
- Species Differences in the Metabolism of (+)-and (-)-Limonenes and their Metabolites, Carveols and Carvones, by Cytochrome P450 Enzymes in Liver Microsomes of Mice, Rats, Guinea Pigs, Rabbits, Dogs, Monkeys, and Humans
- Volatile Flavor Components of ASTRAGALI RADIX (Astragalus membranaceus Bunge)(Organic Chemistry)
- Suppression of SOS-Inducing Activity of Chemical Mutagens by Yakuchinone A from Alpinia oxyphylla in the Salmonella typhimurium TA1535/pSK1002 umu Test
- COMPARISON OF THE EFFECT OF NIFEDIPINE AND DILTIAZEM ON SERUM DIGOXIN CONCENTRATION. A CROSSOVER STUDY : PROCEEDINGS OF THE 47th ANNUAL SCIENTIFIC MEETING OF THE JAPANESE CIRCULATION SOCIETY : Cardiovascular Drugs (I)
- Remote Facilitation of Soleus H-reflex Induced by Clenching on Occlusal Stabilization Appliances
- The Novel Assay Method for Nicotine Metabolism to Cotinine Using High Performance Liquid Chromatography
- A Case of Iron Overload Cardiomyopathy : Beneficial Effects of Iron Chelating Agent and Calcium Channel Blocker on Left Ventricular Dysfunction
- Inhibitory Compounds of α-Glucosidase Activity from Arctium lappa L.
- Identification of the Key Aroma Compounds in Dried Roots of Rubia cordifolia
- Biotransformation of Geraniol by the Larvae of Common Cutworm (Spodoptera litura)
- Microbial Transformation of (-)-Isolongifolol by Plant Pathogenic Fungus Glomerella cingulata
- Influence of Root Exudates from Cucumis sativus and Daucus carota on Arbuscular Mycorrhizal Colonization
- Contractile and Extensile Effects of Red and White Wine on Rat and Mongolian gerbil Gastrointestinal Smooth Muscle
- Identification of the main aroma compounds in dried seeds of Brassica hirta
- A Useful Synthesis of Alkylidenesuccinic Acids by Wittig Reaction in Aqueous Media
- Thoracic Intradural Arachnoid Cyst Associated With Surgical Removal of Epidural Hematoma
- Intramedullary Spinal Tuberculoma : Case Report
- PB-28 A New Bioassy For Acrylamide Toxicity Using Protozoa, Paramecium bursaria(Monitoring,Poster presentation B)
- EFFECTS OF ACRYLAMIDE ON A SYMBIOTIC ASSOCIATION OF SYMBIOTIC ALGAE WITH THE CILIATE PARAMECIUM BURSARIA(Cell Biology and Morphology,Abstracts of papers presented at the 74^ Annual Meeting of the Zoological Society of Japan)
- Serial Batch Elution of Electric Arc Furnace Oxidizing Slag Discharged from Normal Steelmaking Process into Fresh Water
- High-performance liquid chromatographic method for the determination of (-)-verbenone 10-hydroxylation catalyzed by rat liver microsomes
- Biotransformation of (-)-Verbenone by Human Liver Microsomes(Food & Nutrition Science)
- Synthesis and Characterization of New Ascorbic Derivative: Sodium Isostearyl 2-O-L-Ascorbyl Phosphate
- Chemical Composition of Volatile Oil from the Roots of Periploca sepium
- Biotransformation of (-)-Camphor by Salmonella typhimurium OY1002/2A6 Expressing Human CYP2A6 and NADPH-P450 Reductase
- Volatile Flavor Components of SINOMENI CAULIS ET RHIZOMA (Sinomenium acutum Rehder et Wilson)(Organic Chemistry)
- Volatile Flavor Components of PUERARIAE RADIX (Pueraria lobata Ohwi)(Organic Chemistry)
- Volatile Flavor Components of CORNI FRUCTUS (Cornus officinalis Sieb. et Zucc.)(Organic Chemistry)
- Preoperative 18[F]-fluorodeoxyglucose positron emission tomography/computed tomography predicts early recurrence after pancreatic cancer resection
- Biotransformation of Isoflavones by the Larvae of the Common Cutworm (Spodoptera litura)
- Components of the Essential Oil from Matteuccia struthiopteris
- Microbial Transformation of Isopimpinellin by Glomerella cingulata
- Metabolism of (+)-Terpinen-4-ol by Cytochrome P450 Enzymes in Human Liver Microsomes