Cannflavin

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Cannflavins A and B
CannaflavinA.svg
Cannflavin A
CannaflavinB.svg
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
3D model (JSmol)
Properties
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]

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

References[edit]

  1. ^ 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.
  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. ^ Werz, Oliver; Seegers, Julia; Schaible, Anja Maria; Weinigel, Christina; Barz, Dagmar; Koeberle, Andreas; Allegrone, Gianna; Pollastro, Federica; Zampieri, Lorenzo; Grassi, Gianpaolo; Appendino, Giovanni (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.
  5. ^ Rea, Kevin A.; Casaretto, José A.; Al-Abdul-Wahid, M. Sameer; Sukumaran, Arjun; Geddes-Mcalister, Jennifer; Rothstein, Steven J.; Akhtar, Tariq A. (2019). "Biosynthesis of cannflavins a and B from Cannabis sativa L". Phytochemistry. 164: 162–171. doi:10.1016/j.phytochem.2019.05.009. PMID 31151063.