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Canna~Fangled Abstracts

Bioactive prenylogous cannabinoid from fiber hemp (Cannabis sativa).

By September 8, 2011No Comments
Journal of Natural Products

ACS thumbnail siteBioactive Prenylogous Cannabinoid from Fiber Hemp (Cannabis sativa)

Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università del Piemonte Orientale, Via Bovio 6, 28100, Novara, Italy
Dipartimento di Chimica delle Sostanze Naturali,Università di Napoli Federico II, Via Montesano 49, 80131 Napoli, Italy
Endocannabinoid Research Group, Institute of Biomolecular Chemistry, Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80078 Pozzuoli (NA), Italy
Departamento de Biología Celular, Fisiología e Inmunología, Facultad de Medicina, Universidad de Córdoba, Avenida de Menéndez Pidal s/n, 14004 Córdoba, Spain
Endocannabinoid Research Group, Institute of Cybernetics, Consiglio Nazionale delle Ricerche, Via Campi Flegrei 34, 80078 Pozzuoli (NA), Italy
J. Nat. Prod.201174 (9), pp 2019–2022
DOI: 10.1021/np200500p
Publication Date (Web): September 8, 2011
Copyright © 2011 The American Chemical Society and American Society of Pharmacognosy
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Abstract Image

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 (CB1, CB2) and ionotropic (TRPV1, TRPV2, TRPM8, TRPA1) targets of phytocannabinoids showed that prenylogation increased potency toward CB2 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.