Cannflavin

Cannflavins A and B
	; Cannflavin A
	; Cannflavin B
Names
	IUPAC names 6-[(2E)-3,7-Dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one (A); 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-(3-methylbut-2-enyl)chromen-4-one (B)
Identifiers
CAS Number	(A): 76735-57-4 ; (B): 76735-58-5;
3D model (JSmol)	(A): Interactive image; (B): Interactive image;
ChEBI	(A): CHEBI:185375;
ChEMBL	(A): ChEMBL4098732; (B): ChEMBL1985794;
ChemSpider	(A): 8247235; (B): 357679;
PubChem CID	(A): 10071695; (B): 403815;
UNII	(A): GP8SR738HV ; (B): KK2PPP6QRW;
	InChI (B): InChI=1S/C21H20O6/c1-11(2)4-6-13-15(23)9-19-20(21(13)25)16(24)10-17(27-19)12-5-7-14(22)18(8-12)26-3/h4-5,7-10,22-23,25H,6H2,1-3H3 Key: IXCUTZUASDSIJO-UHFFFAOYSA-N;
	SMILES (A): CC(=CCC/C(=C/CC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)OC)O)/C)C; (B): CC(=CCC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)OC)O)C;
Properties
Chemical formula	C26H28O6 (A); C21H20O6 (B)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cannflavins are a group of chemical compounds found in Cannabis sativa.^[1] Chemically, they are prenylflavonoids and are unrelated to THC and other cannabinoids. Cannflavins A and B were first identified in the 1980s and cannflavin C was identified in 2008.^[2]

Because cannflavins A and B are inhibitors of prostaglandin E2 production in vitro,^[1]^[3] the cannflavins have been studied for their potential use as anti-inflammatory agents.^[4]

Biosynthesis

Cannflavins A and B are biosynthesized by prenylation of chrysoeriol.^[5]

References

^ ^a ^b Barrett, M. L.; Scutt, A. M.; Evans, F. J. (1986). "Cannflavin A and B, prenylated flavones from Cannabis sativa L". Experientia. 42 (4): 452–453. doi:10.1007/BF02118655. PMID 3754224. S2CID 19652191.
^ Radwan, Mohamed M.; Elsohly, Mahmoud A.; Slade, Desmond; Ahmed, Safwat A.; Wilson, Lisa; El-Alfy, Abir T.; Khan, Ikhlas A.; Ross, Samir A. (2008). "Non-cannabinoid constituents from a high potency Cannabis sativa variety". Phytochemistry. 69 (14): 2627–2633. Bibcode:2008PChem..69.2627R. doi:10.1016/j.phytochem.2008.07.010. PMC 4888767. PMID 18774146.
^ Barrett, M.L.; Gordon, D.; Evans, F.J. (1985). "Isolation from cannabis sativa L. Of cannflavin—a novel inhibitor of prostaglandin production". Biochemical Pharmacology. 34 (11): 2019–2024. doi:10.1016/0006-2952(85)90325-9. PMID 3859295.
^ Oliver Werz; Julia Seegers; Anja Maria Schaible; et al. (July 2014). "Cannflavins from hemp sprouts, a novel cannabinoid-free hemp food product, target microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase". PharmaNutrition. 2 (3): 53–60. doi:10.1016/J.PHANU.2014.05.001. ISSN 2213-4344. Wikidata Q114911513.
^ Kevin A Rea; José A Casaretto; M S Al-Abdul-Wahid; Arjun Sukumaran; Jennifer Geddes-McAlister; Steven J Rothstein; Tariq A Akhtar (28 May 2019). "Biosynthesis of cannflavins A and B from Cannabis sativa L". Phytochemistry. 164: 162–171. doi:10.1016/J.PHYTOCHEM.2019.05.009. ISSN 0031-9422. PMID 31151063. Wikidata Q92444776.
^ Kevin A Rea; José A Casaretto; M S Al-Abdul-Wahid; Arjun Sukumaran; Jennifer Geddes-McAlister; Steven J Rothstein; Tariq A Akhtar (28 May 2019). "Biosynthesis of cannflavins A and B from Cannabis sativa L". Phytochemistry. 164: 162–171. doi:10.1016/J.PHYTOCHEM.2019.05.009. ISSN 0031-9422. PMID 31151063. Wikidata Q92444776.

[Barrett1986-1] Barrett, M. L.; Scutt, A. M.; Evans, F. J. (1986). "Cannflavin A and B, prenylated flavones from Cannabis sativa L". Experientia. 42 (4): 452–453. doi:10.1007/BF02118655. PMID 3754224. S2CID 19652191.

[2] Radwan, Mohamed M.; Elsohly, Mahmoud A.; Slade, Desmond; Ahmed, Safwat A.; Wilson, Lisa; El-Alfy, Abir T.; Khan, Ikhlas A.; Ross, Samir A. (2008). "Non-cannabinoid constituents from a high potency Cannabis sativa variety". Phytochemistry. 69 (14): 2627–2633. Bibcode:2008PChem..69.2627R. doi:10.1016/j.phytochem.2008.07.010. PMC 4888767. PMID 18774146.

[3] Barrett, M.L.; Gordon, D.; Evans, F.J. (1985). "Isolation from cannabis sativa L. Of cannflavin—a novel inhibitor of prostaglandin production". Biochemical Pharmacology. 34 (11): 2019–2024. doi:10.1016/0006-2952(85)90325-9. PMID 3859295.

[4] Oliver Werz; Julia Seegers; Anja Maria Schaible; et al. (July 2014). "Cannflavins from hemp sprouts, a novel cannabinoid-free hemp food product, target microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase". PharmaNutrition. 2 (3): 53–60. doi:10.1016/J.PHANU.2014.05.001. ISSN 2213-4344. Wikidata Q114911513.

[5] Kevin A Rea; José A Casaretto; M S Al-Abdul-Wahid; Arjun Sukumaran; Jennifer Geddes-McAlister; Steven J Rothstein; Tariq A Akhtar (28 May 2019). "Biosynthesis of cannflavins A and B from Cannabis sativa L". Phytochemistry. 164: 162–171. doi:10.1016/J.PHYTOCHEM.2019.05.009. ISSN 0031-9422. PMID 31151063. Wikidata Q92444776.

[6] Kevin A Rea; José A Casaretto; M S Al-Abdul-Wahid; Arjun Sukumaran; Jennifer Geddes-McAlister; Steven J Rothstein; Tariq A Akhtar (28 May 2019). "Biosynthesis of cannflavins A and B from Cannabis sativa L". Phytochemistry. 164: 162–171. doi:10.1016/J.PHYTOCHEM.2019.05.009. ISSN 0031-9422. PMID 31151063. Wikidata Q92444776.

[1]

[2]

[3]

[4]

[5]

[6]