Isoorientin

Isoorientin (homoorientin) is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside.

Isoorientin

Names
IUPAC name 6-(β-D-Glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
Other names Luteolin-6-C-glucoside Homoorientin
Identifiers
CAS Number	4261-42-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17965 Y
ChemSpider	102753
ECHA InfoCard	100.128.382
KEGG	C01821 Y
PubChem CID	114776
UNII	A37342TIX1 Y
CompTox Dashboard (EPA)	DTXSID50962609
InChI InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1 Key: ODBRNZZJSYPIDI-VJXVFPJBSA-N
SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O)C4C(C(C(C(O4)CO)O)O)O)O)O)O
Properties
Chemical formula	C21H20O11
Molar mass	448.380 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

Natural occurrence

Isoorientin can be isolated from the passion flower,^[1] Vitex negundo,^[2] Terminalia myriocarpa, the Açaí palm, and Swertia japonica.

Potential pharmacology

Isoorientin has been studied for its potential pharmacological activity.^[3] Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri.^[4] Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease.^[5]

Metabolism

• Isoorientin 3'-O-methyltransferase

See also

• Orientin, the 8-C glucoside of luteolin.