Mechanism of Hepatic Microsomal Oxidation of 11-Hydroxy-Δ^8-tetra-hydrocannabinol to 11-Oxo-Δ^8-tetrahydrocannabinol. Evidence for Hydration of the Aldehyde Formed
スポンサーリンク
概要
- 論文の詳細を見る
Hepatic microsomal oxidation of 11-hydroxy-Δ^8-tetrahydrocannabinol (11-OH-Δ^8-THC) to 11-oxo-Δ^8-THC was investigated. Hepatic microsomes from mice, rats, guinea pigs and rabbits catalyzed the oxidation of 11-OH-Δ^8-THC to 11-oxo-Δ^8-THC together with the formation of dihydroxy-Δ^8-THCs oxidized at the 7-position or at the pentyl side chain of 11-OH-Δ^8-THC. 11-Oxo-Δ^8-THC formed under oxygen-18 gas was analyzed by gas chromatography-mass spectrometry (GC-MS) indicating that molecular oxygen was not significantly incorporated into the aldehyde formed. 11-Oxo-Δ^8-THC formed from 11-^<18>OH-Δ^8-THC (^<18>O/^<16>O=0.81-1.05) was also found to lose oxygen-13 from the molecule. These results suggest that 11-oxo-Δ^8-THC is hydrated in the incubation mixture and the aldehyde oxygen is exchangeable with the oxygen atom of water. When 11-oxo-Δ^8-THC was incubated with hepatic microsomes and phosphate buffer containing H_2^<18>O (44 atom%), GC-MS analysis indicated the incorporation of oxygen-18 into the aldehyde recovered from the incubation mixture. The results suggest that the hepatic microsomes may facilitate the hydration of 11-oxo-Δ^8-THC and exchange an oxygen atom of the aldehyde group with that of water in the incubation mixture.
- 社団法人日本薬学会の論文
著者
-
NAKAMURA Seikou
Kyoto Pharmaceutical University
-
中村 紳一郎
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
-
Yamamoto Ikuo
Faculty of Education, Yokohama National University
-
NARIMATSU Shizuo
Faculty of Pharmaceutical Sciences, Okayama University
-
Nakamura S
Toyama Univ. Toyama Jpn
-
WATANABE Kazuhito
Faculty of Pharmaceutical Sciences, Hokuriku University
-
MATSUNAGA Tamihide
Faculty of Pharmaceutical Sciences, Hokuriku University
-
YOSHIMURA Hidetoshi
Department of Food and Nutrition, Nakamura Gakuen University
-
Yamamoto Ikuo
北陸大学 薬 衛化
-
Nakamura S
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
-
Nakamura Satoko
Osaka University Of Pharmaceutical Sciences
-
Narimatsu Shizuo
Laboratories Of Health Chemistry Graduate School Of Medicine Dentistry And Pharmaceutical Sciences O
-
Narimatsu Shizuo
Faculty Of Pharmaceutical Sciences Okayama University
-
Watanabe Kazuhito
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
-
Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen University
-
Narimatsu Shizuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
-
Nakamura S
Laboratories Of Health Chemistry Graduate School Of Medicine Dentistry And Pharmaceutical Sciences O
-
Watanabe Kazuhito
Faculty Of Pharmaceutical Sciences Hokuriku University
-
Matsunaga Tamihide
Faculty Of Pharmaceutical Sciences Kyushu University
-
Watanabe Kazuhito
Faculty Of Pharmaceutical Sciences Kyushu University
-
Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen
-
Yamamoto Ikuo
Faculty Of Education Yokohama National University
関連論文
- Brazilian Natural Medicines. III. Structures of Triterpene Oligoglycosides and Lipase Inhibitors from Mate, Leaves of Ilex paraguariensis
- Medicinal Flowers. XXVI. Structures of Acylated Oleanane-Type Triterpene Oligoglycosides, Yuchasaponins A, B, C, and D, from the Flower Buds of Camellia oleifera : Gastroprotective, Aldose Reductase Inhibitory, and Radical Scavenging Effects
- Medicinal Flowers. XXI. : Structures of Perennisaponins A, B, C, D, E, and F, Acylated Oleanane-Type Triterpene Oligoglycosides, from the Flowers of Bellis perennis
- Effect of Psychotropic Drugs on the 21-Hydroxylation of Neurosteroids, Progesterone and Allopregnanolone, Catalyzed by Rat CYP2D4 and Human CYP2D6 in the Brain(Biochemistry)
- Medicinal Flowers. XXVII : New Flavanone and Chalcone Glycosides, Arenariumosides I, II, III, and IV, and Tumor Necrosis Factor-α Inhibitors from Everlasting, Flowers of Helichrysum arenarium
- Medicinal Flowers. XXX. Eight New Glycosides, Everlastosides F—M, from the Flowers of Helichrysum arenarium
- Medicinal Flowers. XXIV. Chemical Structures and Hepatoprotective Effects of Constituents from Flowers of Hedychium coronarium
- Bioactive Constituents from Chinese Natural Medicines. XXVI : Chemical Structures and Hepatoprotective Effects of Constituents from Roots of Rhodiola sachalinensis
- Apoptosis-Inducing Effects of Sterols from the Dried Powder of Cultured Mycelium of Cordyceps sinensis
- Bioactive Constituents from Chinese Natural Medicines. XXIII. Absolute Structures of New Megastigmane Glycosides, Sedumosides A_4, A_5, A_6, H, and I, and Hepatoprotective Megastigmanes from Sedum sarmentosum
- Bioactive Constituents from Chinese Natural Medicines. XXII. Absolute Structures of New Megastigmane Glycosides, Sedumosides E_1, E_2, E_3, F_1, F_2, and G, from Sedum sarmentosum (Crassulaceae)
- Bioactive Saponins and Glycosides. XXVIII. New Triterpene Saponins, Foliatheasaponins I, II, III, IV, and V, from Tencha (the Leaves of Camellia sinensis)
- P-466 ACYLATED PHENETHYLGLYCOSIDES WITH VASORELAXANT ACTIVITY FROM CISTANCHE TUBULOSA
- Monoterpene Constituents from Cistanche tubulosa : Chemical Structures of Kankanosides A-E and Kankanol
- Brillouin Scattering Study of the Volume Phase Transition in Poly-N-Isopropylacrylamide Gels
- Effect of Several Cellulosic Binders on Particle Size Distribution in Fluidized Bed Granulation
- Effect of Several Cellulosic Binders on Particle Size Distribution of Granules Prepared by a High-Speed Mixer
- Hypnotic Action of N^3-Substituted Arabinofuranosyluracils on Mice
- Synthesis and Central Nervous System Depressant Effects of N^3-Substituted 2', 3'-O-Isopropylideneuridines
- Pharmacologica Efects in Mice of Anandamide and Its Related Fatty Acid Ethanolamides, and Enhancement of Cataleptogenic Effect of Anandamide by Phenylmethylsulfonyl Fluoride
- Synthesis and Sedative-Hypnotic Effects of N^3-Allyl-and N^1-Allyl-5,6-substituted 2-Thiouracil Derivatives in Mice
- Inhibitory Effects of Thunberginols A, B, and F on Degranulations and Releases of TNF-α and IL-4 in RBL-2H3 Cells(Pharmacognosy)
- Determination of Heavy Metal Contents in Human Gallstones Using X-Ray Fluorescence Spectrometry (Regular Presentations) (Proceedings of the 15 th Symposium on Environmental Pollutants and Toxicology)
- Determination of Metal Contents in River Sediment Near a Closed Mine by X-ray Fluorescence Spectrometry (Proceedings of the 14th Symposium on Environmental Pollutants and Toxicology)
- Determination of Metal Contents in Biological and Environmental Materials by Energy-Dispersive X-Ray Fluorescence Analysis
- MECHANISM OF SLEEP-PROLONGATING EFFECT OF Δ^8-TETRAHYDROCANNABINOL (Δ^8-THC) AND ITS METABOLITES
- Mechanism of Hepatic Microsomal Oxidation of 11-Hydroxy-Δ^8-tetra-hydrocannabinol to 11-Oxo-Δ^8-tetrahydrocannabinol. Evidence for Hydration of the Aldehyde Formed
- Inhibitory Effect of Cannabidiol Hydroxy-quinone, and Oxidative Product of Cannabidiol, on the Hepatic Microsomal Drug-Metabolizing Enzymes of Mice
- INTERACTION OF CANNABINOIDS WITH HEPATIC MICROSOMAL DRUG-METABOLIZING ENZYME SYSTEM IN THE RAT
- PURIFICATION AND CHARACTERIZATION OF MOUSE HEPATIC MICROSOMAL ALDEHYDE OXYGENASE
- MECHANISM OF CANNABIELSOIN FORMATION FROM CANNABIDIOL, ONE OF THE MAJOR CMPONENTS OF MARIHUANA
- CYTOCHROME P450 ISOZYMES INVOLVED IN METABOLIC ACTIVATION OF Δ^9-TETRAHYDROCANNABINOL BY RAT LIVER MICROSOMES
- Mechanism of Biological Formation of Cannabielsoin from Cannabidiol in the Guinea-Pig, Mouse, Rat and Rabbit
- HEPATIC MICROSOMAL OXYGENATION OF METHYL GROUP TO CARBOXYLIC ACID IN XENOBIOTICS : METABOLISM OF Δ^8-TETRAHYDROCANNABINOL AT THE 11-POSITION
- Identification of Cannabielsoin, a New Metabolite of Cannabidiol Formed by Guinea-Pig Hepatic Microsomal Enzymes, and Its Pharmacological Activity in Mice
- IN VIVO EFFECTS OF TETRAHYDROCANNABINOLS AND THEIR EIGHT MONOOXYGENATED METABOLITES ON THE HEPATIC MICROSOMAL DRUG-METABOLIZING ENZYME SYSTEMS OF MICE
- METABOLIC ACTIVATION OF CANNABIDIOL BY HEPATIC MICROSOMES. COMPLEX FORMATION WITH CYTOCHROME P-450
- MECHANISM OF THE PROLONGATION OF BARBITURATE-INDUCED SLEEPING TIME AND THE INHIBITION OF THE HEPATIC MICROSOMAL DRUG METABOLIZING ENZYMES BY CANNABIDIOL, A COMPONENT OF CANNABIS
- EFFECTS OF TWO CANNABINOIDS ON HEPATIC MICROSOMAL CYTOCHROME P-450
- METABOLIC ACTIVATION OF Δ^8-THTRAHYDROCANNABINOL (Δ^8-THC) AT THE 7-POSITION AND MECHANISM OF THE OXIDATION OF 7-HYDROXY-Δ^8-THC TO 7-OXO-Δ^8-THC WITH LIVER MICROSOMES
- METABOLIC DISPOSITION OF 8α, 9α-AND 8β, 9β-EPOXYHEXAHYDROCANNABINOLS IN THE MOUSE
- IN VITRO METABOLISM OF TETRAHYDROCANNABINOL (THC) BY HUMAN LIVER MICROSOMES. EPOXIDE-DIOL PATHWAY OF THC
- DIFFERENCE IN EPOXIDES FORMATION AND THEIR FURTHER METABOLISM BETWEEN Δ^9 -AND Δ^8-TETRAHYDROCANNABINOLS BY HUMAN LIVER MICROSOMES
- Sesquiterpenes from Curcuma comosa
- Structures of New Sesquiterpenes from Curcuma comosa
- The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries
- Molecular Characterization of Two Monkey Dihydrodiol Dehydrogenases
- Establishment by Adriamycin Exposure of Multidrug-resistant Rat Ascites Hepatoma AH130 Cells Showing Low DT-diaphorase Activity and High Cross Resistance to Mitomycins
- Inhibition of P-Glycoprotein-Dependent Multidrug Resistance by an Isoquinolinesulfonamide Compound H-87 in Rat Ascites Hepatoma AH66 Cells
- Chemical Constituents from Seeds of Panax ginseng : Structure of New Dammarane-Type Triterpene Ketone, Panaxadione, and HPLC Comparisons of Seeds and Flesh
- Bioactive Constituents from Chinese Natural Medicines. XXXIII : Inhibitors from the Seeds of Psoralea corylifolia on Production of Nitric Oxide in Lipopolysaccharide-Activated Macrophages(Pharmacognosy)
- Structures of New Monoterpenes from Thai Herbal Medicine Curcuma comosa
- Medicinal Flowers. XXII Structures of Chakasaponins V and VI, Chakanoside I, and Chakaflavonoside A from Flower Buds of Chinese Tea Plant (Camellia sinensis)
- New Triterpene Constituents, Foliasalacins A_1-A_4, B_1-B_3, and C, from the Leaves of Salacia chinensis
- Absolute Structures of New Megastigmane Glycosides, Foliasalaciosides E_1, E_2, E_3, F, G, H, and I from the Leaves of Salacia chinensis
- A Novel Series of Thromboxane A_2 Synthetase Inhibitors with Free Radical Scavenging and Anti-peroxidative Activities
- Bioavailable Acyl-CoA : Cholesterol Acyltransferase Inhibitor with Anti-peroxidative Activity : Synthesis and Biological Activity of Novel Indolinyl Amide and Urea Derivatives
- Studies on the Constituents of Broussonetia Species. V. Two New Pyrrolidine Alkaloids, Broussonetines K and L, as Inhibitors of Glycosidase, from Broussonetia Kazinoki SIEB.
- Reinvestigation of Absolute Stereostructure of (-)-Rosiridol : Structures of Monoterpene Glycosides, Rosiridin, Rosiridosides A, B, and C, from Rhodiola sachalinensis
- Bioactive Constituents from Chinese Natural Medicines. XXIX. : Monoterpene and Monoterpene Glycosides from the Roots of Rhodiola sachalinensis
- Bioactive Constituents from Chinese Natural Medicines. XXVIII. : Chemical Structures of Acyclic Alcohol Glycosides from the Roots of Rhodiola crenulata
- Medicinal Flowers. XVII. : New Dammarane-Type Triterpene Glycosides from Flower Buds of American Ginseng, Panax quinquefolium L.
- Medicinal Flowers. XVI. New Dammarane-Type Triterpene Tetraglycosides and Gastroprotective Principles from Flower Buds of Panax ginseng
- Medicinal Flowers. XV. The Structures of Noroleanane- and Oleanane-Type Triterpene Oligoglycosides with Gastroprotective and Platelet Aggregation Activities from Flower Buds of Camellia japonica
- Medicinal Flowers. XIV. New Acylated Oleanane-Type Triterpene Oligoglycosides with Antiallergic Activity from Flower Buds of Chinese Tea Plant(Camellia sinensis)
- Medicinal Flowers. XI. Structures of New Dammarane-Type Triterpene Diglycosides with Hydroperoxide Group from Flower Buds of Panax ginseng
- Bioactive Saponins and Glycosides. XXVII. Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis
- Medicinal Flowers. XII. New Spirostane-Type Steroid Saponins with Antidiabetogenic Activity from Borassus flabellifer
- Bioactive Constituents from Chinese Natural Medicines. XX. Inhibitors of Antigen-Induced Degranulation in RBL-2H3 Cells from the Seeds of Psoralea corylifolia
- Bioactive Saponins and Glycosides. XXV. Acylated Oleanane-Type Triterpene Saponins from the Seeds of Tea Plant (Camellia sinensis)
- Structures of New Cucurbitane-Type Triterpenes and Glycosides, Karavilagenins and Karavilosides, from the Dried Fruit of Momordica charantia L. in Sri Lanka
- P-484 TRITERPENE SAPONINS WITH ANTI-HYPERLIPIDEMIC AND GASTROPROTECTIVE ACTIVITIES FROM TEA PLANT
- P-483 TRITERPENE-SAPONINS WITH HEPATOPROTECTIVE ACTIVITIES FROM THE FLOWER-BUDS OF PANAX NOTOGINSENG AND PANAX GINSENG
- Invasion Inhibitors of Human Fibrosarcoma HT 1080 Cells from the Rhizomes of Zingiber cassumunar: Structures of Phenylbutanoids, Cassumunols
- Reductive Dimerization of Alkylidenemalonates Using Samarium(II) Diiodide and ^1H-NMR Behavior of the Dimers, 2,3-Diaryl-1,1,4,4-butanetetracarboxylates
- Structures of New Flavonoids and Benzofuran-Type Stilbene and Degranulation Inhibitors of Rat Basophilic Leukemia Cells from the Brazilian Herbal Medicine Cissus sicyoides
- Central Nervous System Depressant Effects of N^3-Substituted Derivatives of Deoxyuridine in Mice
- INHIBITORY EFFECT OF CANNABIDIOL ON THE HEPATIC MICROSOMAL DRUG-METABOLIZING ENZYME SYSTEM IN THE RAT
- Studies on the Constituents of Broussonetia Species. IV. Two New Pyrrolidinyl Piperidine Alkaloids, Broussonetines I and J, from Broussonetia kazinoki SIEB.
- Antidiabetogenic Constituents from the Thai Traditional Medicine Cotylelobium melanoxylon
- Studies on the Constituents of Broussonetia Species. III. Two New Pyrrolidine Alkaloids, Broussonetines G and H, as Inhibitors of Glycosidase, from Broussonetia kazinoki SIEB.
- Studies on the Constituents of Broussonetia Species. II. Six New Pyrrolidine Alkaloids, Broussonetine A, B, E, F and Broussonetinine A and B, as Inhibitors of Glycosidases from Broussonetia kazinoki SIEB.
- Medicinal Flowers. XXXI. Acylated Oleanane-Type Triterpene Saponins, Sasanquasaponins I—V, with Antiallergic Activity from the Flower Buds of Camellia sasanqua
- Structures of New Phenylbutanoids and Nitric Oxide Production Inhibitors from the Rhizomes of Zingiber cassumunar
- Medicinal Flowers. XXXII. : Structures of Oleanane-Type Triterpene Saponins, Perennisosides VIII, IX, X, XI, and XII, from the Flowers of Bellis perennis
- Is the Cannabinoid CB1 Receptor a 2-Arachidonoylglycerol Receptor? Structural Requirements for Triggering a Ca^ Transient in NG108-15 Cells
- Chemical Structures and Hepatoprotective Effects of Constituents from the Leaves of Salacia chinensis
- TOLERANCE DEVELOPMENT TO HYPOTHERMIC EFFECT OF Δ^8-TETRAHYDROCANNABINOL AND ITS ACTIVE METABOLITES
- METABOLIC DISPOSITION OF 8α, 9α- AND 8β, 9β-EPOXYHEXAHYDROCANNABINOL (EHHC) IN THE MOUSE
- 9α, 10α-EPOXYHEXAHYDROCANNABINOL FORMATION FROM Δ^9-TETRAHYDROCANNABINOL BY LIVER MICROSOMES OF PHENOBARBITAL-TREATED MICE AND ITS PHARMACOLOGICAL ACTIVITIES IN MICE
- IN VITRO METABOLIC FORMATION OF 8α, 9α-EPOXYHEXAHYDROCANNABINOL AND ITS IMPLICATION IN THE PHARMACOLOGICAL ACTIVITY OF Δ^8-TETRAHYDROCANNABINOL
- Brazilian Natural Medicines. IV. New Noroleanane-Type Triterpene and Ecdysterone-Type Sterol Glycosides and Melanogenesis Inhibitors from the Roots of Pfaffia glomerata
- Medicinal Flowers. XXXIII. Anti-hyperlipidemic and Anti-hyperglycemic Effects of Chakasaponins I–III and Structure of Chakasaponin IV from Flower Buds of Chinese Tea Plant (Camellia sinensis)
- Medicinal Flowers. XXXV. Nor-oleanane-type and acylated oleanane-type triterpene saponins from the flower buds of Chinese Camellia japonica and their inhibitory effects on melanogenesis1)
- Medicinal Flowers. XXXVI.1) Acylated Oleanane-Type Triterpene Saponins with Inhibitory Effects on Melanogenesis from the Flower Buds of Chinese Camellia japonica
- Sesquiterpenes from an Egyptian Herbal Medicine, Pulicaria undulate, with Inhibitory Effects on Nitric Oxide Production in RAW264.7 Macrophage Cells
- Medicinal Flowers. XXXVIII. Structures of Acylated Sucroses and Inhibitory Effects of Constituents on Aldose Reducatase from the Flower Buds of Prunus mume
- Medicinal Flowers. XXXX.1) Structures of Dihydroisocoumarin Glycosides and Inhibitory Effects on Aldose Reducatase from the Flowers of Hydrangea macrophylla var. thunbergii
- Mate Tea (Ilex paraguariensis) Promotes Satiety and Body Weight Lowering in Mice: Involvement of Glucagon-Like Peptide-1
- Chemical Structures and Hepatoprotective Effects of Constituents from Cassia auriculata Leaves