Cannflavin

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • (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
  • (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
C26H28O6 (A)
C21H20O6 (B)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Biosynthetic pathway of cannflavins.[6]

References

  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. 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.

Notes

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