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

Chemical compound

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

^ 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

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)