The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains

Canniprene ( 1 ), an isoprenylated bibenzyl unique to Cannabis sativa, can be vaporized and therefore potentially inhaled from marijuana. Canniprene ( 1 ) potently inhibited the production of inflammatory eicosanoids via the 5-lipoxygenase pathway (IC 50 0.4 μM) and also affected the generation of prostaglandins via the cyclooxygenase/microsomal prostaglandin E 2 synthase pathway (IC 50 10 μM), while the related spiranoid bibenzyls cannabispiranol ( 2 ) and cannabispirenone ( 3 ) were almost inactive in these bioassays. The concentration of canniprene ( 1 ) was investigated in the leaves of 160 strains of C. sativa, showing wide variations, from traces to >0.2%, but no correlation was found between its accumulation and a specific phytocannabinoid profile.