Evaluation of the Cyclooxygenase Inhibiting Effects of Six Major Cannabinoids Isolated from Cannabis sativa

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  • Ruhaak Lucia Renee
    Division of Pharmacognosy, Department of Medicinal Chemistry, Biomedical Centre, Uppsala University Division of Pharmacognosy, Section Metabolomics, Institute of Biology, Leiden University
  • Felth Jenny
    Division of Pharmacognosy, Department of Medicinal Chemistry, Biomedical Centre, Uppsala University
  • Karlsson Pernilla Christina
    Department of Biosciences and Nutrition, Karolinska Institutet
  • Rafter Joseph James
    Department of Biosciences and Nutrition, Karolinska Institutet
  • Verpoorte Robert
    Division of Pharmacognosy, Section Metabolomics, Institute of Biology, Leiden University
  • Bohlin Lars
    Division of Pharmacognosy, Department of Medicinal Chemistry, Biomedical Centre, Uppsala University

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Cyclooxygenase enzymes (COX-1 and COX-2) catalyse the production of prostaglandins from arachidonic acid. Prostaglandins are important mediators in the inflammatory process and their production can be reduced by COX-inhibitors. Endocannabinoids, endogenous analogues of the plant derived cannabinoids, occur normally in the human body. The Endocannabinoids are structurally similar to arachidonic acid and have been suggested to interfere with the inflammatory process. They have also been shown to inhibit cancer cell proliferation. Anti-inflammatory effects of cannabinoids and endocannabinoids have been observed, however the mode of action is not yet clarified. Anti-inflammatory activity (i.e., inhibition of COX-2) is proposed to play an important role in the development of colon cancer, which makes this subject interesting to study further. In the present work, the six cannabinoids tetrahydrocannabinol (Δ9-THC), tetrahydrocannabinolic acid (Δ9-THC-A), cannabidiol (CBD), cannabidiolic acid (CBDA), cannabigerol (CBG) and cannabigerolic acid (CBGA), isolated from Cannabis sativa, were evaluated for their effects on prostaglandin production. For this purpose an in vitro enzyme based COX-1/COX-2 inhibition assay and a cell based prostaglandin production radioimmunoassay were used. Cannabinoids inhibited cyclooxygenase enzyme activity with IC50 values ranging from 1.7·10−3 to 2.0·10−4 M.

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