The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains.
Canniprene (1), an isoprenylated bibenzyl unique to Cannabis sativa, can be vaporized and therefore potentially inhaled from marijuana. Canniprene (1) potently inhibited the production of inflammatory eicosanoids via the 5-lipoxygenase pathway (IC500.4 μM) and also affected the generation of prostaglandins via the cyclooxygenase/microsomal prostaglandin E2synthase pathway (IC5010 μM), while the related spiranoid bibenzyls cannabispiranol (2) and cannabispirenone (3) were almost inactive in these bioassays. The concentration of canniprene (1) was investigated in the leaves of 160 strains of C. sativa, showing wide variations, from traces to >0.2%, but no correlation was found between its accumulation and a specific phytocannabinoid profile.
Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Largo Donegani 2, 28100 Novara, Italy.
Gianna
G
Allegrone
Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Largo Donegani 2, 28100 Novara, Italy.
Federica
F
Pollastro
Consiglio per le Ricerca e la Sperimentazione in Agricoltura, Centro di Ricerca per le Colture Industriali e l'Analisi dell'Economia Agraria, CRA-CIN , Viale G. Amendola 82, 45100 Rovigo, Italy.
Gianmaria
G
Magagnini
Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131 Napoli, Italy.
Orazio
O
Taglialatela-Scafati
Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University Jena , Philosophenweg 14, D-07743 Jena, Germany.
Julia
J
Seegers
Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University Jena , Philosophenweg 14, D-07743 Jena, Germany.
Andreas
A
Koeberle
Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University Jena , Philosophenweg 14, D-07743 Jena, Germany.
Oliver
O
Werz
Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Largo Donegani 2, 28100 Novara, Italy.
Giovanni
0000-0002-4170-9919
G
Appendino
D000818:Animals; D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism; D001632:Bibenzyls / Q000737:chemistry / Q000494:pharmacology*; D002188:Cannabis / Q000737:chemistry* / Q000235:genetics; D015777:Eicosanoids / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D016859:Lipoxygenase Inhibitors / Q000494:pharmacology*; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry
D001632:Bibenzyls; D015777:Eicosanoids; D016859:Lipoxygenase Inhibitors; C000621350:canniprene; D001094:Arachidonate 5-Lipoxygenase