http://www.cnr.it/ontology/cnr/individuo/prodotto/ID19218

Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp. (Articolo in rivista)

Type

Label

Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp. (Articolo in rivista) (literal)

Anno

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

Alternative label

Taglialatela-Scafati O., Pagani A., Scala F., De Petrocellis L.,Di Marzo V., Grassi G., and Appendino G. (2010)
Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp.
in European journal of organic chemistry (Print); WILEY-BLACKWELL, MALDEN 02148,MA (Stati Uniti d'America)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

Taglialatela-Scafati O., Pagani A., Scala F., De Petrocellis L.,Di Marzo V., Grassi G., and Appendino G. (literal)

Pagina inizio

Pagina fine

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Rivista

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Note

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

1. Univ Naples Federico 2, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy 2. Univ Piemonte Orientale, Dipartimento Sci Chim Alimentari Farmaceut & Farm, I-28100 Novara, Italy 3. CNR, Inst Cybernet, Endocannabinoid Res Grp, Pozzuoli, NA, Italy 4. CNR, Inst Biomol Chem, Endocannabinoid Res Grp, Pozzuoli, NA, Italy 5. CRA CIN, I-45100 Rovigo, Italy (literal)

Titolo

Cannabimovone, a Cannabinoid with a Rearranged Terpenoid Skeleton from Hemp. (literal)

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. (literal)

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