Isoorientin

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	448.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isoorientin (or homoorientin) is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside. Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri.[1] Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease.[2]

Natural occurrences

Isoorientin can be isolated from the passion flower, Vitex negundo, Terminalia myriocarpa, the Açaí palm and Swertia japonica.

Metabolism

• Isoorientin 3'-O-methyltransferase

See also

• Orientin, the 8-C glucoside of luteolin.

References

1. Hypoglycaemic activity of Gentiana olivieri and isolation of the active constituent through bioassay- directed fractionation techniques. Ekrem Sezik, Mustafa Aslan, Erdem Yesilada, Shigeru Ito, Life Sciences, 28 January 2005, Volume 76, Issue 11, Pages 1223–1238, doi:10.1016/j.lfs.2004.07.024
2. Zhibin Liang; Bei Zhang; Wei Wen Su; Philip G Williams; Qing X Li (July 2016). "C-Glycosylflavones Alleviate Tau Phosphorylation and Amyloid Neurotoxicity through GSK3β Inhibition". ACS Chemical Neuroscience. 7: 912–923. doi:10.1021/acschemneuro.6b00059. PMC 7355085. PMID 27213824.