Cynaroside

Chemical compound From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
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).
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Natural occurrences

It can be found in Ferula varia and F. foetida[1] in Campanula persicifolia and C. rotundifolia,[2] in the bamboo Phyllostachys nigra,[3] and in Teucrium gnaphalodes.[4]

In food

It can be found in dandelion (the highest concentration in the flowers,[5] but also in the roots) and in Cynara scolymus (artichoke).[6]

Biosynthesis and metabolism

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

 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 

The glucose unit is transferred from uridine diphosphate glucose, with uridine diphosphate (UDP) as byproduct.[7]

A cynaroside 7-O-glucosidase has been identified in the artichoke.[6]

References

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