Chemistry:Cynaroside

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Cynaroside
Cynaroside.svg
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
KEGG
UNII
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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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. 
  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. https://wildfoodism.com/2014/04/17/is-the-healthiest-part-of-dandelion-its-flower/. 
  6. ↑ 6.0 6.1 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. http://www.actahort.org/books/681/681_58.htm. 
  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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