TY - JOUR
T1 - 8α,9α-Epoxyhexahydrocannabinol formation from Δ8-tetrahydrocannabinol by mouse liver microsomes
AU - Yamamoto, Ikuo
AU - Narimatsu, Shizuo
AU - Watanabe, Kazuhito
AU - Yoshimura, Hidetoshi
PY - 1982/12/15
Y1 - 1982/12/15
N2 - 8α,9α-Epoxyhexahydrocannabinol ( EHHC ) was formed from Δ8-tetrahydrocannabinol ( THC ) by mouse liver microsomes. The reaction required O2, and partially inhibited by CO. The optimal pH for the epoxide formation was from 7.4 to 8.0. EDTA did not affect the epoxide formation, but SKF 525-A, α-naphthoflavone and CCl4 caused a significant inhibition. In addition, the rate of epoxidation increased significantly after treatment. with phenobarbital and 3-methylcholanthrene, but decreased after CoCl2 treatment. 8β,9β-EHHC, a stereoisomer of 8α,9α-EHHC, was not found under all the conditions used in this study. These results indicate that 8α,9α-EHHC formation is mediated by monooxygenase system involving cytochrome P-450.
AB - 8α,9α-Epoxyhexahydrocannabinol ( EHHC ) was formed from Δ8-tetrahydrocannabinol ( THC ) by mouse liver microsomes. The reaction required O2, and partially inhibited by CO. The optimal pH for the epoxide formation was from 7.4 to 8.0. EDTA did not affect the epoxide formation, but SKF 525-A, α-naphthoflavone and CCl4 caused a significant inhibition. In addition, the rate of epoxidation increased significantly after treatment. with phenobarbital and 3-methylcholanthrene, but decreased after CoCl2 treatment. 8β,9β-EHHC, a stereoisomer of 8α,9α-EHHC, was not found under all the conditions used in this study. These results indicate that 8α,9α-EHHC formation is mediated by monooxygenase system involving cytochrome P-450.
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U2 - 10.1016/0006-291X(82)92028-9
DO - 10.1016/0006-291X(82)92028-9
M3 - Article
C2 - 6297494
AN - SCOPUS:0020410066
SN - 0006-291X
VL - 109
SP - 922
EP - 926
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 3
ER -