Luteolin-7-O-glucuronide

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
CAS Number	38934-20-2;
3D model (JSmol)	Interactive image;
ChemSpider	24784676;
KEGG	C03515;
PubChem CID	25245094;
CompTox Dashboard (EPA)	DTXSID50952181 ;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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

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

luteolin 7-O-(β-D-glucuronosyl-(1→2)-β-D-glucuronide)

↑ Capanlar, S; Böke, N; Yaşa, I; Kirmizigül, S (2010). "A novel glycoside from Acanthus hirsutus (Acanthaceae)". Natural Product Communications. 5 (4): 563–6. doi:10.1177/1934578X1000500414. PMID 20433073. S2CID 6169110.
1 2 3 Schulz, Margot; Weissenböck, Gottfried (1988). "Three specific UDP-glucuronate: Flavone-glucuronosyl-transferases from primary leaves of Secale cereale". Phytochemistry. 27 (5): 1261. doi:10.1016/0031-9422(88)80175-4.
1 2 Anhalt, Stephan; Weissenböck, Gottfried (1992). "Subcellular localization of luteolin glucuronides and related enzymes in rye mesophyll". Planta. 187 (1): 83–8. doi:10.1007/BF00201627. PMID 24177970. S2CID 7887567.