Stereospecific and Regioselective Hydrolysis of Cannabinoid Esters by ES46.5K, an Esterase from Mouse Hepatic Microsomes, and Its Differences from Carboxylesterases of Rabbit and Porcine Liver(Biochemistry)

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概要

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• The properties of ES46.5K, an esterase from mouse hepatic microsomes, were compared with those of carboxylesterases from rabbit and porcine liver. The inhibitory profile with a serine hydrolase inhibitor (bis-p-nitrophenylphosphate) and detergents (sodium dodecylsulfate, Emulgen 911) was different between ES46.5K and the carboxylesterases. Bis-p-nitrophenylphosphate (0.1mM) markedly inhibited the catalytic activity of the carboxylesterases but not that of ES46.5K. Emulgen 911 (0.05-0.25%) inhibited the catalytic activity of the carboxylesterases, whereas the detergent conversely stimulated that of ES46.5K by 150%. The two carboxylesterases catalyzed the hydrolysis of acetate esters of tetrahydrocannabinol (THC) analogues with different side chain lengths (C_1-C_5), although ES46.5K showed marginal activity only against the acetate of Δ^8-tetrahydrocannabiorcol, a methyl side chain derivative of Δ^8-THC. ES46.5K hydrolyzed cannabinoid esters stereospecifically and regioselectively. The esterase hydrolyzed 8α-acetoxy-Δ^9-tetrahydrocannabinol (8α-acetoxy-Δ^9-THC, 5.62nmol/min/mg protein), while the enzyme did not hydrolyze 8β-acetoxy-Δ^9-THC, 7α-acetoxy-, and 7β-acetoxy-Δ^8-THC at all. In contrast, the carboxylesterases from rabbit and porcine liver hydrolyzed 8β-acetoxy-Δ^9-THC efficiently but not 8α-acetoxy-Δ^9-THC. ES46.5K hydrolyzed side chain acetoxy derivatives of Δ^8-THC at the 3'-and 4'-positions, and a methyl ester of 5'-nor-Δ^8-THC-4'-oic acid. The enzyme, however, could not hydrolyze methyl esters of Δ^8-and Δ^9-THC-11-oic acid, while both carboxylesterases hydrolyzed side chain acetoxy derivatives of Δ^8-THC and three methyl esters of THC-oic acids. These differences in stereospecificity and regioselectivity between ES46.5K and carboxylesterases suggest that the configurations of important amino acids for the catalytic activities of these enzymes are different from each other.

• 社団法人日本薬学会の論文
• 2005-09-01

著者

• 景山 節

  京大・霊長類研・生化学

• Yamamoto Ikuo

  Department Of Hygienic Chemistry School Of Pharmaceutical Sciences Kyushu University Of Health And W

• Yamaori Satoshi

  Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University

• Watanabe Kazuhito

  Department of Hygienic Chemistry, Faculty of Pharmaceutical Sciences, Hokuriku University

• FUNAHASHI Tatsuya

  Faculty of Pharmaceutical Sciences, Okayama University

• WATANABE Kazuhito

  Faculty of Pharmaceutical Sciences, Hokuriku University

• MATSUNAGA Tamihide

  Division of Pharmacy, Shinshu University Hospital

• KIMURA Toshiyuki

  Faculty of Pharmaceutical Sciences, Hokuriku University

• YAMAORI Satoshi

  Faculty of Pharmaceutical Sciences, Hokuriku University

• SHOYAMA Yukihiro

  Graduate School of Pharmaceutical Sciences, Kyushu University

• YAMAMOTO Ikuo

  School of Pharmaceutical Sciences, Kyushu University of Health and Welfare

• Yamamoto Ikuo

  北陸大学 薬 衛化

• YAMAMOTO IKUO

  Hygienic Chemistry

• Kimura T

  Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University

• 景山 節

  京都大学霊長類研究所人類進化モデル研究センター

• 景山 節

  京大・霊長研

• Yamaori Satoshi

  Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University

• Watanabe Kazuhito

  Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University

• Funahashi Tatsuya

  Department Of Hygienic Chemistry Faculty Of Pharmaceutical Sciences Hokuriku University

• Funahashi Tatsuya

  Faculty Of Pharmaceutical Sciences Okayama University

• Kimura T

  Department Of Medicinal Chemistry Center For Frontier Research In Medicinal Science 21st Century Coe

• Kimura Toshiyuki

  Faculty Of Engineering Yokohama National University

• Yamamoto I

  Hokuriku Univ. Kanazawa Jpn

• Watanabe Kazuhito

  Faculty Of Pharmaceutical Sciences Hokuriku University

• Yamamoto I

  Hygienic Chemistry

• Shoyama Y

  Department Of Pharmacognosy Faculty Of Pharmaceutical Sciences Nagasaki International University

• Shoyama Yukihiro

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Matsunaga Tamihide

  Division Of Pharmacy Shinshu University Hospital

• Watanabe Kazuhito

  Faculty Of Pharmaceutical Sciences Kyushu University

• Yamamoto Ikuo

  School Of Pharmaceutical Sciences Kyushu University Of Health And Welfare

• Yamamoto Ikuo

  Hygienic Chemistry School Of Pharmacy Hokuriku University

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