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Luteolin-7-O-glucuronide

Chemical compound From Wikipedia, the free encyclopedia

Luteolin-7-O-glucuronide is a chemical compound that is classified as a flavone.

Quick facts Names, Identifiers ...
Luteolin-7-O-glucuronide
Chemical structure of luteolin-7-O-glucuronide
Names
IUPAC name
(2S,3S,4S,5R)-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
Other names
Luteolin-7-O-beta-D-glucuronide
Luteolin 7-O-beta-D-glucuronide
Identifiers
3D model (JSmol)
ChemSpider
KEGG
  • InChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/p-1/t16-,17-,18+,19-,21?/m0/s1
    Key: VSUOKLTVXQRUSG-DAZJWRSOSA-M
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)[O-])O)O)O)O)O)O
Properties
C21H18O12
Molar mass 462.363 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Close

It is found in Acanthus hirsutus[1] and in rye (Secale cereale).[2][3]

Biosynthesis and metabolism

Luteolin 7-O-glucuronosyltransferase is the glucuronosyltransferase that uses UDP-glucuronate to convert luteolin its glucuronide by adding a sugar acid at one of the phenolic hydroxy groups, with uridine diphosphate (UDP) as byproduct:[2]

Luteolin-7-O-glucuronide 2"-O-glucuronosyltransferase is an enzyme that adds a second sugar group to luteolin-7-O-glucuronide to give luteolin 7-O-(beta-D-glucuronosyl-(1→2)-beta-D-glucuronide).[2][3]

luteolin-7-O-glucuronide + UDP-glucuronate
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27127061.
luteolin 7-O-(β-D-glucuronosyl-(1→2)-β-D-glucuronide)

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