Editing Cannabinoid (section)

=== Cannabinoids in other plants ===

Phytocannabinoids are known to occur in several plant species besides cannabis. These include ''[[Echinacea purpurea]]'', ''[[Echinacea angustifolia]]'', ''[[Acmella oleracea]]'', [[Helichrysum|''Helichrysum umbraculigerum'']], and ''[[Radula marginata]]''.<ref name="Woelkart-2008">{{cite journal | vauthors = Woelkart K, Salo-Ahen OM, Bauer R | title = CB receptor ligands from plants | journal = Current Topics in Medicinal Chemistry | volume = 8 | issue = 3 | pages = 173–186 | year = 2008 | pmid = 18289087 | doi = 10.2174/156802608783498023 }}</ref> The best-known cannabinoids that are not derived from Cannabis are the [[Anandamide]]-like alkylamides from ''[[Echinacea]]'' species, most notably the cis/trans [[isomers]] of dodeca-2E,4E,8Z,10E/Z-tetraenoic-acid-isobutylamide.<ref name="Woelkart-2008" /> At least 25 different [[alkylamide]]s have been identified, and some of them have shown affinities to the CB<sub>2</sub>-receptor.<ref name="Bauer-1989">{{cite journal | vauthors = Bauer R, Remiger P | title = TLC and HPLC Analysis of Alkamides in Echinacea Drugs1,2 | journal = Planta Medica | volume = 55 | issue = 4 | pages = 367–371 | date = August 1989 | pmid = 17262436 | doi = 10.1055/s-2006-962030 | s2cid = 12138478 }}</ref><ref>{{cite journal | vauthors = Raduner S, Majewska A, Chen JZ, Xie XQ, Hamon J, Faller B, Altmann KH, Gertsch J | display-authors = 6 | title = Alkylamides from Echinacea are a new class of cannabinomimetics. Cannabinoid type 2 receptor-dependent and -independent immunomodulatory effects | journal = The Journal of Biological Chemistry | volume = 281 | issue = 20 | pages = 14192–14206 | date = May 2006 | pmid = 16547349 | doi = 10.1074/jbc.M601074200 | doi-access = free }}</ref>  In some ''Echinacea'' species, cannabinoids are found throughout the plant structure, but are most concentrated in the roots and flowers.<ref name="Perry-1997">{{cite journal | vauthors = Perry NB, van Klink JW, Burgess EJ, Parmenter GA | title = Alkamide levels in Echinacea purpurea: a rapid analytical method revealing differences among roots, rhizomes, stems, leaves and flowers | journal = Planta Medica | volume = 63 | issue = 1 | pages = 58–62 | date = February 1997 | pmid = 17252329 | doi = 10.1055/s-2006-957605 | s2cid = 260280073 }}</ref><ref>{{cite journal | vauthors = He X, Lin L, Bernart MW, Lian L |year=1998 |title=Analysis of alkamides in roots and achenes of Echinacea purpurea by liquid chromatography–electrospray mass spectrometry |journal=Journal of Chromatography A |volume=815 |issue=2 |pages=205–11 |doi=10.1016/S0021-9673(98)00447-6}}</ref> [[Yangonin]] found in the [[kava]] plant has significant affinity to the CB1 receptor.<ref>{{cite journal | vauthors = Ligresti A, Villano R, Allarà M, Ujváry I, Di Marzo V | title = Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand | journal = Pharmacological Research | volume = 66 | issue = 2 | pages = 163–169 | date = August 2012 | pmid = 22525682 | doi = 10.1016/j.phrs.2012.04.003 }}</ref> Tea ([[Camellia sinensis]]) [[catechins]] have an affinity for human cannabinoid receptors.<ref name="urlmissclasses.com">{{cite journal | vauthors = Korte G, Dreiseitel A, Schreier P, Oehme A, Locher S, Geiger S, Heilmann J, Sand PG | display-authors = 6 | title = Tea catechins' affinity for human cannabinoid receptors | journal = Phytomedicine | volume = 17 | issue = 1 | pages = 19–22 | date = January 2010 | pmid = 19897346 | doi = 10.1016/j.phymed.2009.10.001 }}</ref> A widespread dietary terpene, [[beta-caryophyllene]], a component from the [[Cannabis flower essential oil|essential oil of cannabis]] and other medicinal plants, has also been identified as a selective agonist of peripheral CB<sub>2</sub>-receptors, ''[[in vivo]]''.<ref>{{cite journal | vauthors = Gertsch J, Leonti M, Raduner S, Racz I, Chen JZ, Xie XQ, Altmann KH, Karsak M, Zimmer A | display-authors = 6 | title = Beta-caryophyllene is a dietary cannabinoid | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 105 | issue = 26 | pages = 9099–9104 | date = July 2008 | pmid = 18574142 | pmc = 2449371 | doi = 10.1073/pnas.0803601105 | doi-access = free | bibcode = 2008PNAS..105.9099G }}</ref> [[Black truffles]] contain anandamide.<ref>{{cite journal | vauthors = Pacioni G, Rapino C, Zarivi O, Falconi A, Leonardi M, Battista N, Colafarina S, Sergi M, Bonfigli A, Miranda M, Barsacchi D, Maccarrone M | display-authors = 6 | title = Truffles contain endocannabinoid metabolic enzymes and anandamide | journal = Phytochemistry | volume = 110 | pages = 104–110 | date = February 2015 | pmid = 25433633 | doi = 10.1016/j.phytochem.2014.11.012 | bibcode = 2015PChem.110..104P }}</ref> [[Perrottetinene]], a moderately psychoactive cannabinoid,<ref>{{cite journal | vauthors = Chicca A, Schafroth MA, Reynoso-Moreno I, Erni R, Petrucci V, Carreira EM, Gertsch J | title = Uncovering the psychoactivity of a cannabinoid from liverworts associated with a legal high | journal = Science Advances | volume = 4 | issue = 10 | pages = eaat2166 | date = October 2018 | pmid = 30397641 | pmc = 6200358 | doi = 10.1126/sciadv.aat2166 | bibcode = 2018SciA....4.2166C }}</ref> has been isolated from different ''[[Radula (plant)|Radula]]'' varieties. [[Machaeriol A]] and related compounds are found in plants from the ''[[Machaerium (plant)|Machaerium]]'' family.<ref>Muhammad I, Li XC, Jacob MR, Tekwani BL, Dunbar DC, Ferreira D. Antimicrobial and antiparasitic (+)-trans-hexahydrodibenzopyrans and analogues from Machaerium multiflorum. ''J Nat Prod''. 2003 Jun;66(6):804-9. {{doi|10.1021/np030045o}} {{PMID|12828466}}</ref>

Most of the phytocannabinoids are nearly insoluble in water but are soluble in [[lipid]]s, [[Alcohol (chemistry)|alcohols]], and other non-polar [[organic solvent]]s.