2. Academic Validation
  3. The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains

The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains

  • J Nat Prod. 2017 Mar 24;80(3):731-734. doi: 10.1021/acs.jnatprod.6b01126.
Gianna Allegrone 1,  Federica Pollastro 1,  Gianmaria Magagnini 2,  Orazio Taglialatela-Scafati 3,  Julia Seegers 4,  Andreas Koeberle 4,  Oliver Werz 4,  Giovanni Appendino 1
Affiliations

Affiliations

  • 1 Dipartimento di Scienze del Farmaco, Università del Piemonte Orientale , Largo Donegani 2, 28100 Novara, Italy.
  • 2 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.
  • 3 Dipartimento di Farmacia, Università di Napoli Federico II , Via Montesano 49, 80131 Napoli, Italy.
  • 4 Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University Jena , Philosophenweg 14, D-07743 Jena, Germany.
PMID: 28165233 DOI: 10.1021/acs.jnatprod.6b01126
Abstract

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 (IC50 0.4 μM) and also affected the generation of prostaglandins via the cyclooxygenase/microsomal prostaglandin E2 synthase pathway (IC50 10 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.

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