The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains, Journal of Natural Products, 2017, Gianna Allegrone, Federica Pollastro, Gianmaria Magagnini, Orazio Taglialatela-Scafati, Julia Seegers, Andreas Koeberle, Oliver Werz, and Giovanni Appendino
Un articolo medico pubblicato nel 2017 in cui si dimostra la potenza antinfiammatoria del canniprene, un elemento presente unicamente nella Cannabis sativa. Pertanto anche dalla canapa da fibra potrà essere estratto il canniprene, senza far uso del THC o del CBD. Un altro vantaggio del canniprene è che può essere inalato.
“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 and also affected the generation of prostaglandins via the cyclooxygenase/microsomal prostaglandin synthase pathway, while the related spiranoid bibenzyls cannabispiranol (2) and cannabispirenone (3) were almost inactive in these bioassays. The concentration of 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.
The isoprenylated bibenzyl canniprene (1) was first isolated by Crombie and Crombie in 1978 from a Thai sample of a high-THC (Δ-tetrahydrocannabinol) strain of Cannabis sativa L. (Cannabaceae), and this pioneer group of cannabis phytochemistry also reported its synthesis two years later. Canniprene was also isolated from another THC strain of cannabis originating from Panama, as well as from other narcotic samples of the plant (marijuana). Most samples were of the cannabidiol (CBD)-chemotype, showing that the biosynthesis of 1 and that of cannabinoids are orthogonal and unrelated, since 1 could be detected not only in marijuana but also in fiber hemp. When marijuana is smoked, 1 can therefore be inhaled along with the decarboxylated phytocannabinoids. The cannflavin C. sativa phenolics are potent inhibitors of the production of inflammatory eicosanoids generated via the 5-lipoxygenase and the cyclooxygenase/microsomal prostaglandin C. sativa is a prolific producer of stilbenoids derived from dimethyldihydroresveratrol by intramolecular phenol coupling, a process that generates spiro-derivatives (cannabis-piranoids) by para−para coupling and next phenanthrenes from their rearrangement (cannithrenoids, formally the products of a para−meta coupling).
Conversely, 1 is the result of hydroxylation and prenylation of the basic chemotype and is the only phenolic that has so far been reported to significantly (>0.1%) accumulate in C. sativa strains.
the remarkable potential anti-inflammatory activity of canniprene as a dual inhibitor of adds to the growing evidence that C. sativa is a source of unique noncannabinoid phenolics, of which the biomedical relevance still awaits a systematic investigation”.
Testo estratto da The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains, Journal of Natural Products, 2017, Gianna Allegrone, Federica Pollastro, Gianmaria Magagnini, Orazio Taglialatela-Scafati, Julia Seegers, Andreas Koeberle, Oliver Werz, and Giovanni Appendino