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Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp

2010; Wiley; Volume: 2010; Issue: 11 Linguagem: Inglês

10.1002/ejoc.200901464

1434-193X

Orazio Taglialatela‐Scafati, Alberto Pagani, Fernando Scala, Luciano De Petrocellis, Vincenzo Di Marzo, Gianpaolo Grassi, Giovanni Appendino,

Psychedelics and Drug Studies

Abstract An investigation of the polar fractions from a nonpsychotropic variety of hemp ( Cannabis sativa L.) afforded cannabimovone ( 6 ), a polar cannabinoid with a rearranged 2(3→4) abeo ‐terpenoid skeleton, biogenetically originating from the intramolecular aldolization of a 2′,3′‐ seco ‐menthanyl precursor. The structure of cannabimovone was elucidated by spectroscopic analysis, whereas attempts to mimic its biogenetic derivation from cannabidiol ( 2 ) gave only anhydrocannabimovone ( 12 ), the intramolecular oxy‐Michael adduct of the crotonized version ( 11b ) of the elusive natural products. Biological evaluation of cannabimovone ( 6 ) against metabotropic (CB 1 , CB 2 ) and ionotropic (TRPs) cannabinoid receptors showed a significant activity only for ionotropic receptors, especially TRPV1, whereas anhydrocannabimovone ( 12 ) exhibited strong activity at both ionotropic and metabotropic cannabinoid receptors. Overall, the biological profile of anhydrocannabimovone ( 12 ) was somewhat similar to that of THC ( 4 ), suggesting a remarkable tolerance to constitutional and configurational changes.