Avicularin information

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 ;
3D model (JSmol)	Interactive image;
ChemSpider	20130086;
KEGG	C22608;
PubChem CID	5490064;
UNII	TN38NQ38BQ ;
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]

^ 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
^ ^a ^b 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

[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

[Fujimori-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

Avicularin information

and 28 Related for: Avicularin information

Avicularin

Polygonum aviculare

Rhododendron aureum

Quercetin

Icariin

Fisetin

Rutin

Kaempferol

Isoquercetin

Tragia volubilis

Myricetin

Psidium guineense

Flavonols

Troxerutin

Monoxerutin

Syringetin

C20H18O11

Karanjin

Trifolin

Quercitrin

Galangin

Dictionary of natural phenols and polyphenols molecular formulas

Hyperoside

Taxillus kaempferi

Karanjachromene

Tamarixetin

Isorhamnetin

Guaijaverin