Avicularin

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
CAS Number	572-30-5^Y
3D model (JSmol)	Interactive image
ChemSpider	20130086
KEGG	C22608
PubChem CID	5490064
UNII	TN38NQ38BQ^Y
CompTox Dashboard (EPA)	DTXSID60205832
InChI 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
SMILES 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
Chemical formula	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

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. 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.