Cynaroside

Cynaroside
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-3′,4′,5-trihydroxysexflavone
Systematic IUPAC name
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
Other names
Glucoluteolin
Luteoloside
Cinaroside
7-Glucoluteolin
7-Glucosylluteolin
Luteolin 7-glucoside
Luteolin-7-glucoside
Luteolin 7-O-glucoside
Luteolin-7-O-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.023.968 Edit this at Wikidata
KEGG
UNII
  • InChI=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 checkY
    Key: PEFNSGRTCBGNAN-QNDFHXLGSA-N checkY
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
Properties
C21H20O11
Molar mass 4488.37 g/mol
Appearance Yellow amorphous powder
Melting point 266 to 268 °C (511 to 514 °F; 539 to 541 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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).

Biosynthesis and metabolism

Flavone 7-O-beta-glucosyltransferase, characterised from parsley, forms the glucoside of the flavone, luteolin.

2D representation of the chemical structure of luteolin .
luteolin
+ UDP-glucose
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of cynaroside.
cynaroside

The glucose unit is transferred from uridine diphosphate glucose, with uridine diphosphate (UDP) as byproduct.

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

References

  1. ↑ Yuldashev, M. P. (1997). "Cynaroside content of the plants Ferula varia and F. Foetida". Chemistry of Natural Compounds. 33 (5): 597–8. doi:10.1007/BF02254816. S2CID 45802688.
  2. ↑ Teslov, L. S.; Teslov, S. V. (1972). "Cynaroside and luteolin from Campanula persicifolia and C. Rotundifolia". Chemistry of Natural Compounds. 8: 117. doi:10.1007/BF00564462.
  3. ↑ Hu, Chun; Zhang, Ying; Kitts, David D. (2000). "Evaluation of Antioxidant and Prooxidant Activities of Bamboo Phyllostachys nigra Var. Henonis Leaf Extract in Vitro". Journal of Agricultural and Food Chemistry. 48 (8): 3170–6. doi:10.1021/jf0001637. PMID 10956087.
  4. ↑ 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
  5. ↑ "Is the Healthiest Part of Dandelion Its Flower?". 17 April 2014.
  6. 1 2 Nüβlein, B; Kreis, W (2005). "Purification and Characterization of a Cynaroside 7-O-β-D-Glucosidase from Cynarae scolymi folium". Acta Horticulturae. 681 (681): 413–20. doi:10.17660/ActaHortic.2005.681.58.
  7. ↑ Sutter A, Ortmann R, Grisebach H (1972). "Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the transfer of D-glucose from UDP-D-glucose to flavonoids". Biochim. Biophys. Acta. 258 (1): 71–87. doi:10.1016/0005-2744(72)90967-9. PMID 5058406.