Cynaroside

Cynaroside
Names
	IUPAC name 7-(β-D-Glucopyranosyloxy)-3′,4′,5-trihydroxyflavone
	Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(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
CAS Number	5373-11-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27994 ;
ChemSpider	4444241 ;
ECHA InfoCard	100.023.968
KEGG	C03951 ;
PubChem CID	5280637;
UNII	98J6XDS46I ;
CompTox Dashboard (EPA)	DTXSID50949617 ;
	InChI 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 Key: PEFNSGRTCBGNAN-QNDFHXLGSA-N ; 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 Key: PEFNSGRTCBGNAN-QNDFHXLGBE;
	SMILES 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
Chemical formula	C21H20O11
Molar mass	448.37 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). verify (what is ?) Infobox references

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

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

UV-Vis^[7]
Lambda-max	UV : 348, 260 nm
Extinction coefficient	(log ε): 4.11, 4.23
IR
Major absorption bands	? cm⁻¹
NMR
Proton NMR	1H-NMR (500 MHz, CD3COCD3 + D2O): δ 3.42 (1H, t, J = 9.0 Hz, H-4′), 3.49 (1H, t, J = 9.0 Hz, H-2″), 3.56 (1H, t, J = 9.0 Hz, H-3″), 3.60 (1H, m, H-5″) , 3.68 (1H, dd, J = 12.2, 5.6 Hz, H-6a″), 3.85 (1H, dd, J = 12.2, 1.8 Hz, H-6b″), 5.10 (1H, d, J = 7.8 Hz, H-1″), 6.44 (1H, d, J = 1.8 Hz, H-6), 6.63 (1H, s, H-3), 6.83 (1H, d, J = 1.8 Hz, H-8), 6.95 (1H, d, J = 8.0 Hz, H-5′), 7.41 (1H, d, J = 8.0 Hz, H-6′), 7.43 (1H, bs, H-2′)
Carbon-13 NMR	13C-NMR (125 MHz, CD3COCD3 + D2O): δ 61.7 (C-6″), 70.3 (C-4″), 73.8 (C-2″), 76.8 (C-3″), 77.4 (C-5″), 95.8 (C-8), 100.5 (C-6), 100.7 (C-1″), 103.7 (C-3), 106.3 (C-10), 113.8 (C-2″), 116.5 (C-5′), 120.3 (C-6′), 122.6 (C-1′), 146.3(C-3′), 150.4 (C-4′), 158.0 (C-9), 161.8 (C-5), 163.9 (C-7), 165.8(C-2), 183.1 (C-4)
Other NMR data
MS
Masses of main fragments	ESI-MS [M+H]+ m/z 449.1

^ 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.
^ 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.
^ 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.
^ 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
^ "Is the Healthiest Part of Dandelion Its Flower?". 17 April 2014.
^ ^a ^b 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.
^ Lin, Yi-Pei; Chen, Tai-Yuan; Tseng, Hsiang-Wen; Lee, Mei-Hsien; Chen, Shui-Tein (2009). "Neural cell protective compounds isolated from Phoenix hanceana var. Formosana". Phytochemistry. 70 (9): 1173–81. doi:10.1016/j.phytochem.2009.06.006. PMID 19628235.

Names

IUPAC name 7-(β-D-Glucopyranosyloxy)-3′,4′,5-trihydroxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(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
CAS Number	5373-11-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27994^N
ChemSpider	4444241^N
ECHA InfoCard	100.023.968
KEGG	C03951^Y
PubChem CID	5280637
UNII	98J6XDS46I^Y
CompTox Dashboard (EPA)	DTXSID50949617
InChI 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^N Key: PEFNSGRTCBGNAN-QNDFHXLGSA-N^N 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 Key: PEFNSGRTCBGNAN-QNDFHXLGBE
SMILES 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
Chemical formula	C₂₁H₂₀O₁₁
Molar mass	448.37 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). N verify (what is ^YN ?) Infobox references