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	76735-57-4 (A) ; 76735-58-5 (B);
3D model (JSmol)	(A): Interactive image; (B): Interactive image;
PubChem CID	10071695 (A); 403815 (B);
UNII	GP8SR738HV ;
	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. 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.

Notes

This article is a direct transclusion of the Wikipedia article and therefore may not meet the same editing standards as LIMSwiki.

[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. 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.

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Cannflavin

Biosynthesis

References

Notes

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Names
Cannflavin A
Cannflavin B
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	76735-57-4 (A)^Y 76735-58-5 (B)
3D model (JSmol)	(A): Interactive image (B): Interactive image
PubChem CID	10071695 (A) 403815 (B)
UNII	GP8SR738HV^Y
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