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Isosakuranetin

Chemical compound From Wikipedia, the free encyclopedia

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.[2] Isosakuranetin is a potent inhibitor of TRPM3 channels.[3]

Quick facts Names, Identifiers ...
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[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.866 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: HMUJXQRRKBLVOO-AWEZNQCLSA-N checkY
  • COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O
Properties
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).
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Biosynthesis

In soybean, isosakuranetin is biosynthesised from naringenin in a methylation reaction catalysed by the enzyme flavonoid 4'-O-methyltransferase.[1] The methyl group comes from the cofactor, S-adenosyl methionine (SAM)

2D representation of the chemical structure of naringenin .
naringenin
+ SAM
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of isosakuranetin .
isosakuranetin
+ SAH
 

Glycosides

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