Mechanism of Biological Formation of Cannabielsoin from Cannabidiol in the Guinea-Pig, Mouse, Rat and Rabbit
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概要
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Biological formation of cannabielsoin (CBE) from cannabidiol (CBD) was studied in the guinea pig, mouse, rat and rabbit in vitro. Emphasis was placed on the elucidation of this formation mechanism. The enzyme activity of CBE formation was localized in hepatic microsomes. The enzymatic reaction required nicotinamide adenine dinucleotide phosphate (NADPH) and molecular oxygen, and showed an optimal pH around 7.3. The microsomal CBE-forming activities decreased in the following order ; guinea pig>mouse≧rabbit≧rat. The CBE formation in the guinea pig hepatic microsomes was suppressed with various inhibitors of cytochrome P-450 such as SKF 525-A, α-naphthoflavone and carbon monoxide, but not by disodium ethylenediamine tetraacetate. When in-cubated with the microsomes either in the presence or absence of NADPH, a synthetic epoxide of CBD, 1S, 2R-epoxy-CBD-2', 6'-diacetate was easily and exclusively converted to CBE. On the other hand, 1R, 2S-epoxy-CBD was not changed to CBE at all, but to several oxidized metabolites. These results suggest that CBD is biotransformed to 1S, 2R-epoxy-CBD with hepatic microsomal monooxygenase system including cytochrome P-450,and the epoxide is immediately converted to CBE.
- 社団法人日本薬学会の論文
著者
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NAKAMURA Seikou
Kyoto Pharmaceutical University
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中村 紳一郎
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
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YAMAMOTO IKUO
Department of Laboratory Medicine, Miyazaki Medical College
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Nakamura S
Toyama Univ. Toyama Jpn
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YOSHIMURA Hidetoshi
Department of Food and Nutrition, Nakamura Gakuen University
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Yamamoto Ikuo
北陸大学 薬 衛化
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Yamamoto Ikuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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Nakamura S
Specialty Chemicals Research Center Shin-etsu Chemical Co. Ltd.
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NARIMATSU SHIZUO
Departments of Hygienic Chemistry
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GOHDA Hiroshi
Department of Hygienic Chemistry, School of Pharmacy, Hokuriku University
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Gohda H
Hokuriku Univ. Kanazawa Jpn
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Nakamura Satoko
Osaka University Of Pharmaceutical Sciences
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Narimatsu Shizuo
Laboratories Of Health Chemistry Graduate School Of Medicine Dentistry And Pharmaceutical Sciences O
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Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen University
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Narimatsu Shizuo
Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University
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Nakamura S
Laboratories Of Health Chemistry Graduate School Of Medicine Dentistry And Pharmaceutical Sciences O
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Yoshimura Hidetoshi
Department Of Food And Nutrition Nakamura Gakuen
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Yamamoto Ikuo
Department Of Bioapplied Chemistry Faculty Of Engineering Osaka City University
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Narimatsu Shizuo
Department of Health Chemistry, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University
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