Pinocembrin

Pinocembrin is a flavanone, a type of flavonoid. It is an antioxidant found in damiana,[1] honey, fingerroot,[2] and propolis.[3]

Pinocembrin
Names
IUPAC name
5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
Other names
Dihydrochrysin
Galangin flavanone
5,7-Dihydroxyflavanone
5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-
5,7-Dihydroxy-2-phenyl-chroman-4-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2 checkY
    Key: URFCJEUYXNAHFI-UHFFFAOYSA-N checkY
  • InChI=1/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2
    Key: URFCJEUYXNAHFI-UHFFFAOYAA
  • O=C2c3c(OC(c1ccccc1)C2)cc(O)cc3O
Properties
C15H12O4
Molar mass 256.257 g·mol−1
Density 1.386 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Pinocembrin can be converted biosynthetically to pinobanksin by hydroxylation adjacent to the ketone. Studies have shown that pinocembrin has potential as a drug to treat cerebral ischemia, intracerebral hemorrhage, neurodegenerative diseases, cardiovascular diseases and atherosclerosis as well as other diseases.[4][5]

See also

References
  1. Zhao, J; Dasmahapatra AK; Khan SI; Khan IA (Dec 2008). "Anti-aromatase activity of the constituents from damiana (Turnera diffusa)". J Ethnopharmacol. 120 (3): 387–393. doi:10.1016/j.jep.2008.09.016. PMID 18948180.
  2. Punvittayagul, C; Wongpoomchai R; Taya S; Pompimon W. (January 2011). "Effect of pinocembrin isolated from Boesenbergia pandurata on xenobiotic-metabolizing enzymes in rat liver". Drug Metabolism Letters. 5 (1): 1–5. doi:10.2174/187231211794455226. PMID 20942797.
  3. Bosio K; Avanzini C; D’Avolio A; Ozino O; Savoia D (2000). "In vitro activity of propolis against Streptococcus pyogenes". Letters in Applied Microbiology. 31 (2): 174–177. doi:10.1046/j.1365-2672.2000.00785.x. PMID 10972723. S2CID 1622868.
  4. Lan X, Wang W, Li Q, Wang J (April 2016). "The natural flavonoid pinocembrin: molecular targets and potential therapeutic applications". Mol Neurobiol. 53 (3): 1794–801. doi:10.1007/s12035-015-9125-2. PMC 4561606. PMID 25744566.
  5. Lan X, Han X, Li Q, Li Q, Gao Y, Cheng T, Wan J, Zhu W, Wang J, Lan X, Wang W, Li Q, Wang J (March 2017). "Pinocembrin protects hemorrhagic brain primarily by inhibiting toll-like receptor 4 and reducing M1 phenotype microglia". Brain Behav. Immun. 61: 326–339. doi:10.1016/j.bbi.2016.12.012. PMC 5453178. PMID 28007523.


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