Cynaroside

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

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.023.968
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 ☒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
  • 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 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).
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Infobox references

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.
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