Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp | Zendy

TaglialatelaScafati Orazio | Zendy; Pagani Alberto | Zendy; Scala Fernando | Zendy; De Petrocellis Luciano | Zendy; Di Marzo Vincenzo | Zendy; Grassi Gianpaolo | Zendy; Appendino Giovanni | Zendy

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Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp

Author(s) -

TaglialatelaScafati Orazio,

Pagani Alberto,

Scala Fernando,

De Petrocellis Luciano,

Di Marzo Vincenzo,

Grassi Gianpaolo,

Appendino Giovanni

Publication year - 2010

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200901464

Subject(s) - ionotropic effect , chemistry , cannabidiol , stereochemistry , cannabinoid , metabotropic receptor , cannabinoid receptor , terpenoid , intramolecular force , receptor , biochemistry , cannabis , glutamate receptor , antagonist , psychology , psychiatry

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.

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