Ayanin

Ayanin
Chemical structure of ayanin
Chemical structure of ayanin
Names
IUPAC name
3′,5-Dihydroxy-3,4′,7-trimethoxyflavone
Systematic IUPAC name
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,7-dimethoxy-4H-1-benzopyran-4-one
Other names
  • 3,7,4'-Tri-O-methylquercetin
  • 3,7,4'-Trimethylquercetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C18H16O7/c1-22-10-7-12(20)15-14(8-10)25-17(18(24-3)16(15)21)9-4-5-13(23-2)11(19)6-9/h4-8,19-20H,1-3H3 checkY
    Key: KPCRYSMUMBNTCK-UHFFFAOYSA-N checkY
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)OC)O)OC)O
Properties
C18H16O7
Molar mass 344.319 g·mol−1
Density 1.454 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ayanin is an O-methylated flavonol, a type of flavonoid. It is the 3,7,4'-tri-O-methylated derivative of quercetin.

It can be found in Croton schiedeanus. It can also be synthesized.

Biosynthesis

The biosynthesis of ayanin in Chrysosplenium americanum is by the sequential methylation of the flavonol, quercetin. The first enzyme, quercetin 3-O-methyltransferase uses the cofactor, S-adenosyl methionine (SAM) to transfer a methyl group specifically at the 3-position:

2D representation of the chemical structure of quercetin .
quercetin
+ SAM
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q23068616.
3-O-methylquercetin
+ SAH
 

Two additional enzymes, 3-methylquercetin 7-O-methyltransferase and 3,7-dimethylquercetin 4'-O-methyltransferase complete the production of ayanin:

3-O-methylquercetin
 
7 methyl
 
 
Rightward reaction arrow
 
 
 
3,7-dimethylquercetin
 
4' methyl
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of ayanin .
ayanin

References

  1. ↑ Rao, Koppaka V.; Owoyale, Jacob A. (1976). "Partial methylation of quercetin: Direct synthesis of tamarixetin, ombuin and ayanin". Journal of Heterocyclic Chemistry. 13 (6): 1293–1295. doi:10.1002/jhet.5570130629.
  2. 1 2 De Luca V, Ibrahim RK (1985). "Enzymatic synthesis of polymethylated flavonols in Chrysosplenium americanum. I. Partial purification and some properties of S-adenosyl-L-methionine:flavonol 3-, 6-, 7-, and 4'-O-methyltransferases". Arch. Biochem. Biophys. 238 (2): 596–605. doi:10.1016/0003-9861(85)90205-X. PMID 3994393.