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

Gianna Allegrone, Federica Pollastro, Gianmaria Magagnini, Orazio Taglialatela-Scafati, Julia Seegers, Andreas Koeberle, Oliver Werz, Giovanni Appendino

Journal of natural products 2017 Mar 24

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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 (IC50 0.4 μM) and also affected the generation of prostaglandins via the cyclooxygenase/microsomal prostaglandin E2 synthase pathway (IC50 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.

Citation

Gianna Allegrone, Federica Pollastro, Gianmaria Magagnini, Orazio Taglialatela-Scafati, Julia Seegers, Andreas Koeberle, Oliver Werz, Giovanni Appendino. The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains. Journal of natural products. 2017 Mar 24;80(3):731-734