Bioactive Prenylogous Cannabinoid from Fiber Hemp (Cannabis sativa)

The waxy fraction from the variety Carma of fiber hemp (Cannabis sativa) afforded the unusual cannabinoid 4, identified as the farnesyl prenylogue of cannabigerol (CBG, 1) on the basis of its spectroscopic properties. A comparative study of the profile of 4 and 1 toward metabotropic (CB(1), CB(2)) and ionotropic (TRPV1, TRPV2, TRPM8, TRPA1) targets of phytocannabinoids showed that prenylogation increased potency toward CB(2) by ca. 5-fold, with no substantial difference toward the other end-points, except for a decreased affinity for TRPM8. The isolation of 4 suggests that C. sativa could contain yet-to-be-discovered prenylogous versions of medicinally relevant cannabinoids, for which their biological profiles could offer interesting opportunities for biomedical exploitation.