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
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
C20 H18 O11
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).
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
Flavonols
Aglycones Conjugates
Glycosides of herbacetin 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 Conjugates 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)
Derivative flavonols
Aglycones
Noricaritin
Dihydronoricaritin
Glycosides
Pyranoflavonols
Furanoflavonols
Semisynthetic
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