Cynaroside

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^Y
PubChem	5280637
ChEBI	CHEBI:27994^Y
Jmol-3D images	Image 1
SMILES C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
Properties
Molecular formula	C₂₁H₂₀O₁₁
Molar mass	448.37 g/mol
Appearance	Yellow amorphous powder
Melting point	266–268 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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

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

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

^ 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.
^ 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.
^ ^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: 413–20.
^ 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	6-Hydroxyflavone

Dihydroxyflavones	Chrysin (5,7-dihydroxyflavone) 4',7-Dihydroxyflavone

Trihydroxyflavones	Apigenin (5,7,4'-trihydroxyflavone) Baicalein (5,6,7-trihydroxyflavone) Norwogonin (5,7,8-Trihydroxyflavone)

Tetrahydroxyflavones	Isoscutellarein (5,7,8,4'-Tetrahydroxyflavone or 8-Hydroxyapigenin) Luteolin (3',4',5,7-Tetrahydroxyflavone) Norartocarpetin (2',4',5,7-Tetrahydroxyflavone) Scutellarein (5,6,7,4'-Tetrahydroxyflavone)

Pentahydroxyflavones	Hypolaetin (8-Hydroxyluteolin) Tricetin (5,7,3',4',5'-Pentahydroxyflavone)

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)

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	Cynaroside (Luteolin 7-O-glucoside) Isoorientin (Luteolin 6-C-glucoside) Orientin (Luteolin 8-C-glucoside) Veronicastroside (Luteolin 7-O-neohesperidoside)

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

Sulfated glycosides

Theograndin I (sulfated glucuronide of isoscutellarein) and II

Polymers

Synthetic

This article about a natural phenol is a stub. You can help Wikipedia by expanding it.

This page is available in 1 language