Avicularin

Last updated
Avicularin
Avicularin.svg
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
PubChem CID
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 lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells. [2]

References

  1. ↑ Xu, Fuquan; Guan, Huashi; Li, Guoqiang; Liu, Hongbing (2009). "LC Method for Analysis of Three Flavonols in Rat Plasma and Urine after Oral Administration of Polygonum aviculare Extract". Chromatographia. 69 (11–12): 1251–1258. doi:10.1365/s10337-009-1088-x.
  2. 1 2 Fujimori, K; Shibano, M (2013). "Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells". J Agric Food Chem. 61 (21): 5139–5147. doi:10.1021/jf401154c. PMID   23647459.


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