Avicularin

Source: Wikipedia, the free encyclopedia.
Avicularin
Names
IUPAC name
3-(α-L-Arabinofuranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name
3-{[(2S,3R,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
Other names
quercetin-3-O-α-L-arabinofuranoside
quercetin-3-O-α-arabinofuranoside
Avicularine
Avicularoside
Fenicularin
Quercetin 3-alpha-L-arabinofuranoside
Identifiers
3D model (
JSmol
)
ChemSpider
KEGG
UNII
  • InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
    Key: BDCDNTVZSILEOY-UXYNSRGZSA-N
  • InChI=1/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
    Key: BDCDNTVZSILEOY-UXYNSRGZBK
  • C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
Properties
C20H18O11
Molar mass 434.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Avicularin is a bio-active

flavonol isolated from a number of plants including Polygonum aviculare,[1] Rhododendron aureum and Taxillus kaempferi.[2]

It suppresses

C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells.[2]

References