Avicularin

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

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).
Infobox references

It suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells.[2]

References
  1. LC Method for Analysis of Three Flavonols in Rat Plasma and Urine after Oral Administration of Polygonum aviculare Extract. Fuquan Xu, Huashi Guan, Guoqiang Li and Hongbing Liu, Chromatographia, June 2009, Volume 69, Issue 11-12, pages 1251-1258, doi:10.1365/s10337-009-1088-x
  2. Avicularin, a plant flavonoid, suppresses lipid accumulation through repression of C/EBPα-activated GLUT4-mediated glucose uptake in 3T3-L1 cells. Fujimori K and Shibano M, J Agric Food Chem., 29 May 2013, volume 61, issue 21, pages 5139-5147, doi:10.1021/jf401154c, PMID 23647459



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