3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol

Canniprene, an isoprenylated bibenzyl unique to Cannabis sativa, is a potent inhibitor of 5-lipoxygenase (5-LO) activity (IC50=0.4 μM) and cyclooxygenase/microsomal prostaglandin E2 synthase (PGE2; IC50=10 μM). Canniprene inhibits the production of inflammatory eicosanoids and affects the generation of prostaglandins[1].

5-LO: 0.4 μM (IC₅₀); PGE₂: 10 μM (IC₅₀)

[1] Allegrone G, et al. The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains. J Nat Prod. 2017 Mar 24;80(3):731-734. DOI:10.1021/acs.jnatprod.6b01126