TY - JOUR
T1 - The Bibenzyl Canniprene Inhibits the Production of Pro-Inflammatory Eicosanoids and Selectively Accumulates in Some Cannabis sativa Strains
AU - Allegrone, Gianna
AU - Pollastro, Federica
AU - Magagnini, Gianmaria
AU - Taglialatela-Scafati, Orazio
AU - Seegers, Julia
AU - Koeberle, Andreas
AU - Werz, Oliver
AU - Appendino, Giovanni
N1 - Publisher Copyright:
© 2017 The American Chemical Society and American Society of Pharmacognosy.
PY - 2017/3/24
Y1 - 2017/3/24
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85016156961&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.6b01126
DO - 10.1021/acs.jnatprod.6b01126
M3 - Article
SN - 0163-3864
VL - 80
SP - 731
EP - 734
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 3
ER -