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
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	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). N  verify  (what is  YN ?) 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 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]

Metabolism

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

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

Spectral data

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

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. 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. 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.