Isosakuranetin

Isosakuranetin

Isosakuranetin
Names
IUPAC name (2S)-5,7-Dihydroxy-4′-methoxyflavan-4-one
Systematic IUPAC name (2S)-5,7-Dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
Other names 4'-Methylnaringenin Ponciretin
Identifiers
CAS Number	480-43-3 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL470266 Y
ChemSpider	141023 Y
ECHA InfoCard	100.006.866
KEGG	C05334
PubChem CID	160481
UNII	U02X7TF8UA Y
CompTox Dashboard (EPA)	DTXSID60963980
InChI InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1 Y Key: HMUJXQRRKBLVOO-AWEZNQCLSA-N Y
SMILES COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O
Properties
Chemical formula	C16H14O5
Molar mass	286.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isosakuranetin, an O-methylated flavonoid, is the 4'-methoxy derivative of naringenin, a flavanone. Didymin, a disaccharide of isosakuranetin, occurs e.g. in scarlet beebalm, sweet orange, blood orange and mandarin. Isosakuranetin is a potent inhibitor of TRPM3 channels.

Biosynthesis

In soybean, isosakuranetin is biosynthesised from naringenin in a methylation reaction catalysed by the enzyme flavonoid 4'-O-methyltransferase. The methyl group comes from the cofactor, S-adenosyl methionine (SAM)

naringenin

+ SAM

 

 

 

 

 

 

 

isosakuranetin

+ SAH

 

Glycosides

• Poncirin is the 7-O-neohesperidoside of isosakuranetin.
• Didymin is the 7-O-rutinoside of isosakuranetin