8α,9α-Epoxyhexahydrocannabinol formation from Δ8-tetrahydrocannabinol by mouse liver microsomes

Ikuo Yamamoto, Shizuo Narimatsu, Kazuhito Watanabe, Hidetoshi Yoshimura

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8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)922-926
Number of pages5
JournalBiochemical and Biophysical Research Communications
Volume109
Issue number3
DOIs
Publication statusPublished - Dec 15 1982

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ASJC Scopus subject areas

  • Biophysics
  • Biochemistry
  • Molecular Biology
  • Cell Biology

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