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- W2059969163 abstract "The psychoactive cannabinoids from Cannabis sativa L. and the arachidonic acid-derived endocannabinoids are nonselective natural ligands for cannabinoid receptor type 1 (CB 1 ) and CB 2 receptors. Although the CB 1 receptor is responsible for the psychomodulatory effects, activation of the CB 2 receptor is a potential therapeutic strategy for the treatment of inflammation, pain, atherosclerosis, and osteoporosis. Here, we report that the widespread plant volatile ( E )-β-caryophyllene [( E )-BCP] selectively binds to the CB 2 receptor ( K i = 155 ± 4 nM) and that it is a functional CB 2 agonist. Intriguingly, ( E )-BCP is a common constituent of the essential oils of numerous spice and food plants and a major component in Cannabis . Molecular docking simulations have identified a putative binding site of ( E )-BCP in the CB 2 receptor, showing ligand π–π stacking interactions with residues F117 and W258. Upon binding to the CB 2 receptor, ( E )-BCP inhibits adenylate cylcase, leads to intracellular calcium transients and weakly activates the mitogen-activated kinases Erk1/2 and p38 in primary human monocytes. ( E )-BCP (500 nM) inhibits lipopolysaccharide (LPS)-induced proinflammatory cytokine expression in peripheral blood and attenuates LPS-stimulated Erk1/2 and JNK1/2 phosphorylation in monocytes. Furthermore, peroral ( E )-BCP at 5 mg/kg strongly reduces the carrageenan-induced inflammatory response in wild-type mice but not in mice lacking CB 2 receptors, providing evidence that this natural product exerts cannabimimetic effects in vivo . These results identify ( E )-BCP as a functional nonpsychoactive CB 2 receptor ligand in foodstuff and as a macrocyclic antiinflammatory cannabinoid in Cannabis ." @default.
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- W2059969163 date "2008-07-01" @default.
- W2059969163 modified "2023-09-28" @default.
- W2059969163 title "Beta-caryophyllene is a dietary cannabinoid" @default.
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- W2059969163 doi "https://doi.org/10.1073/pnas.0803601105" @default.
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