Cynaroside

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

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444296203 | Name = Cynaroside | Reference = | ImageFile = Cynaroside.svg | ImageSize = 300px | IUPACName = 7-(β-D-Glucopyranosyloxy)-3′,4′,5-trihydroxysexflavone | SystematicName = 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-69-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | OtherNames = Glucoluteolin Luteoloside Cinaroside 7-Glucoluteolin 7-Glucosylluteolin Luteolin 7-glucoside Luteolin-7-glucoside Luteolin 7-O-glucoside Luteolin-7-O-glucoside |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 5373-11-5 | UNII_Ref = | UNII = 98J6XDS46I | KEGG_Ref = | KEGG = C03951 | PubChem = 5280637 | ChemSpiderID_Ref = | ChemSpiderID = 4444241 | SMILES = C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4C@@HO)O)O)O | InChI = 1/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 | InChIKey = PEFNSGRTCBGNAN-QNDFHXLGBE | StdInChI_Ref = | StdInChI = 1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1 | StdInChIKey_Ref = | StdInChIKey = PEFNSGRTCBGNAN-QNDFHXLGSA-N | ChEBI_Ref = | ChEBI = 27994 |Section2={{Chembox Properties | Formula = C21H20O11 | MolarMass = 4488.37 g/mol | Appearance = Yellow amorphous powder | Density = | MeltingPtC = 266 to 268 | MeltingPt_notes = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Cynaroside (also known as luteoloside) is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin.

Natural occurrences

It can be found in Ferula varia and F. foetida in Campanula persicifolia and C. rotundifolia, in the bamboo Phyllostachys nigra, and in Teucrium gnaphalodes.

; In food It can be found in dandelion (the highest concentration in the flowers, but also in the roots) and in Cynara scolymus (artichoke).

Metabolism

Flavone 7-O-beta-glucosyltransferase adds a glucose to luteolin.

A cynaroside 7-O-glucosidase has been identified in the artichoke.

Spectral data

::data[format=table] | | UV-Vis | | IR | | NMR | | MS | |---|---|---|---| | Lambda-max | UV : 348, 260 nm | | | | Extinction coefficient | (log ε): 4.11, 4.23 | | | | Major absorption bands | ? cm−1 | | | | Proton NMR | 1H-NMR (500 MHz, CD3COCD3 + D2O): | | | | Carbon-13 NMR | 13C-NMR (125 MHz, CD3COCD3 + D2O): | | | | Other NMR data 19F chem. shifts, omit if not used -- | | | | | Masses of main fragments | ESI-MS [M+H]+ m/z 449.1 | | | ::

References

References

  2. (1997). "Cynaroside content of the plants ''Ferula varia'' and ''F. Foetida''". Chemistry of Natural Compounds.
  3. (1972). "Cynaroside and luteolin from Campanula persicifolia and C. Rotundifolia". Chemistry of Natural Compounds.
  4. (2000). "Evaluation of Antioxidant and Prooxidant Activities of Bamboo ''Phyllostachys nigra'' Var. ''Henonis'' Leaf Extract in Vitro". Journal of Agricultural and Food Chemistry.
  5. Flavonoid Aglycones and Glycosides from Teucrium gnaphalodes. F. A. T. Barberán, M. I. Gil, F. Tomás, F. Ferreres and A. Arques, J. Nat. Prod., 1985, 48 (5), pages 859–860, {{doi. 10.1021/np50041a040
  6. (17 April 2014). "Is the Healthiest Part of Dandelion Its Flower?".
  7. (2005). "Purification and Characterization of a Cynaroside 7-O-β-D-Glucosidase from Cynarae scolymi folium". Acta Horticulturae.
  8. (2009). "Neural cell protective compounds isolated from Phoenix hanceana var. Formosana". Phytochemistry.

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flavone-glucosidescatechols