Characterization of microsomal alcohol oxygenase catalyzing the oxidation of 7-hydroxy-Δ8-tetrahydrocannabinol to 7-oxo-Δ8- tetrahydrocannabinol in rat liver

Tamihide Matsunaga, Kinya Shibayama, Shinsuke Higuchi, Hiroyuki Tanaka, Kazuhito Watanabe, Ikuo Yamamoto

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The formation of 7-oxo-Δ8-tetrahydrocannabinol (7-oxo-Δ8-THC) from 7β-hydroxy-Δ8-THC was found in hepatic microsomes of rats. The activity was stereoselective and about 3-fold higher than that from 7α-hydroxy-Δ8- THC. The oxidative activity of 7α- and 7β-hydroxy-Δ8-THC to 7-oxo-Δ8- THC was significantly higher in male than in female, and significantly enhanced by both dexamethasone and phenobarbital, and then inhibited up to about 20% of the control value by antibody against P450GPF-B, presumably a member of the 3A subfamily, a major enzyme responsible for the formation of 7-oxo-Δ8-THC in guinea pigs. This antibody also inhibited the formation of 7α- and 7β-hydroxy-Δ8-THC, and 7-oxo-Δ8-THC from Δ8-THC by hepatic microsomes of rats. These results indicate that there is a sex-related difference in the oxidation of 7-hydroxy-Δ8-THC to 7-oxo-Δ8-THC and the reaction is mainly catalyzed by P450 enzyme(s) belonging to the 3A subfamily as major enzyme(s) of microsomal alcohol oxygenase in rats.

Original languageEnglish
Pages (from-to)43-46
Number of pages4
JournalBiological and Pharmaceutical Bulletin
Issue number1
Publication statusPublished - Jan 2000

All Science Journal Classification (ASJC) codes

  • Pharmacology
  • Pharmaceutical Science


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