Isoorientin

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title: "Isoorientin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["flavone-glucosides", "c-glycoside-natural-phenols"] topic_path: "general/flavone-glucosides" source: "https://en.wikipedia.org/wiki/Isoorientin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| ImageFile = Homoorientin.svg | ImageSize = 250px | IUPACName = 6-(β-D-Glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone | SystematicName = 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 | OtherNames = Luteolin-6-C-glucoside Homoorientin |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 4261-42-1 | UNII_Ref= | UNII = A37342TIX1 | 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 | InChIKey = ODBRNZZJSYPIDI-VJXVFPJBSA-N | PubChem = 114776 | ChEBI_Ref = | ChEBI = 17965 | KEGG_Ref = | KEGG = C01821 | ChemSpiderID = 102753 | ChEMBL_Ref = | ChEMBL = | 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 |Section2={{Chembox Properties | C=21 | H=20 | O=11 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt =

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

Natural occurrence

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

Potential pharmacology

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

Metabolism

References

References

  1. (2013). "Glycosidic Inhibitors of Melanogenesis from Leaves of ''Passiflora edulis''". Chemistry & Biodiversity.
  2. (2007). "New antifungal flavonoid glycoside from Vitex negundo". Bioorganic & Medicinal Chemistry Letters.
  3. (2020). "Isoorientin: A dietary flavone with the potential to ameliorate diverse metabolic complications". Pharmacological Research.
  4. 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
  5. (July 2016). "C-Glycosylflavones Alleviate Tau Phosphorylation and Amyloid Neurotoxicity through GSK3β Inhibition". ACS Chemical Neuroscience.

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flavone-glucosidesc-glycoside-natural-phenols