| pubmed-article:18574142 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:18574142 | lifeskim:mentions | umls-concept:C0006864 | lld:lifeskim |
| pubmed-article:18574142 | lifeskim:mentions | umls-concept:C0012155 | lld:lifeskim |
| pubmed-article:18574142 | lifeskim:mentions | umls-concept:C0525503 | lld:lifeskim |
| pubmed-article:18574142 | pubmed:issue | 26 | lld:pubmed |
| pubmed-article:18574142 | pubmed:dateCreated | 2008-7-7 | lld:pubmed |
| pubmed-article:18574142 | pubmed:abstractText | 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)-beta-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 pi-pi 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. | lld:pubmed |
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| pubmed-article:18574142 | pubmed:language | eng | lld:pubmed |
| pubmed-article:18574142 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:18574142 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:18574142 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
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| pubmed-article:18574142 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:18574142 | pubmed:month | Jul | lld:pubmed |
| pubmed-article:18574142 | pubmed:issn | 1091-6490 | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:GertschJürgJ | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:ZimmerAndreas... | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:RaczIldikoI | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:LeontiMarcoM | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:AltmannKarl-H... | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:XieXiang-QunX... | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:ChenJian-Zhon... | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:KarsakMelihaM | lld:pubmed |
| pubmed-article:18574142 | pubmed:author | pubmed-author:RadunerStefan... | lld:pubmed |
| pubmed-article:18574142 | pubmed:issnType | Electronic | lld:pubmed |
| pubmed-article:18574142 | pubmed:day | 1 | lld:pubmed |
| pubmed-article:18574142 | pubmed:volume | 105 | lld:pubmed |
| pubmed-article:18574142 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:18574142 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:18574142 | pubmed:pagination | 9099-104 | lld:pubmed |
| pubmed-article:18574142 | pubmed:dateRevised | 2009-11-19 | lld:pubmed |
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