Cynaroside

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Cynaroside
IUPAC name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-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 68321-11-9 YesY
PubChem 5280637
ChEBI CHEBI:27994 N
Jmol-3D images Image 1
Properties
Molecular formula C21H20O11
Molar mass 448.37 g/mol
Appearance Yellow amorphous powder
Melting point 266–268 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cynaroside is a flavone, a flavonoid-like chemical compound. It is a 7-O-glucoside of luteolin and can be found in dandelion coffee, in Ferula varia and F. foetida[1] in Campanula persicifolia and C. rotundifolia,[2] in the bamboo Phyllostachys nigra[3] and in Cynara scolymus (artichoke).[4]

Metabolism

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

A cynaroside 7-O-glucosidase has been identified in the artichoke.[4]

Spectral data

UV-Vis[5]
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. ↑ 4.0 4.1 Nüβlein, B; Kreis, W (2005). "Purification and Characterization of a Cynaroside 7-O-β-D-Glucosidase from Cynarae scolymi folium". Acta Horticulturae 681: 413–20. 
  5. ↑ 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. 
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
  • Acacetin (Apigenin 4'-methyl ether)
  • Artocarpetin (Norartocarpetin 7-methyl ether)
  • Diosmetin (Luteolin 4'-methyl ether)
  • Eupatilin (5,7-Dihydroxy-3',4',6-trimethoxyflavone)
  • Genkwanin (Apigenin 7-methyl ether)
  • Nepetin (Luteolin 6-methyl ether)
  • Nobiletin (3',4',5,6,7,8-Hexamethoxyflavone)
  • Oroxylin A (Baicalein 6-methyl ether)
  • Pratol (7-Hydroxy-4-methoxyflavone)
  • Sinensetin (3',4',5,6,7-Pentamethoxyflavone)
  • Tangeritin (4',5,6,7,8-Pentamethoxyflavone)
  • Techtochrysin (Chrysin 7-methyl ether)
  • Tricin (Tricetin 3',5'-dimethyl ether)
  • Wogonin (Norwogonin 8-methyl ether)
  • Zapotin (2,6,5,6-tetramethoxyflavone)
Glycosides
of apigenin
  • Apiin (Apigenin-7-O-apioglucoside)
  • Apigetrin (Apigenin 7-O-glucoside)
  • Isovitexin (Apigenin 6-C-glucoside)
  • Rhoifolin (Apigenin 7-O-neohesperidoside)
  • Saponarin (Isovitexin-7-O-glucoside)
  • Schaftoside (Apigenin 6-C-glucoside 8-C-arabinoside)
  • Vicenin-2 (Apigenin 6,8-di-C-glucoside)
  • Vitexin (Apigenin-8-C-glucoside)
of baicalein
  • Baicalin (Baicalein 7-O-glucuronide)
  • Tetuin (Baicalein 6-O-glucoside)
of hypolaetin
  • Hypolaetin 8-glucoside
  • Hypolaetin 8-glucuronide
of luteolin
  • Giraldiin A (4',5,5',7-Tetrahydroxy-3-methoxy-3'-O-α-L-arabinopyranosyloxyflavone) and B (5,5',7'-Trihydroxy-2',3-dimethoxy-4'-O-β-D-glucopyranosyloxyflavone)
  • Nepitrin (Nepetin 7-O-glucoside)
  • Oroxindin (Wogonin 7-O-glucuronide)
  • Scutellarin (Scutellarein 7-O-glucuronide)
Acetylated
  • Artocarpetin A (prenylated artocarpetin)
  • Artoindonesianin P (prenylated)
Sulfated glycosides
Theograndin I (sulfated glucuronide of isoscutellarein) and II
Polymers
Synthetic
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