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Wikipedia

Cynaroside

January 01, 1970

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
  • 5373-11-5 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:27994 N
ChemSpider
  • 4444241 N
ECHA InfoCard 100.023.968
KEGG
  • C03951 Y
  • 5280637
UNII
  • 98J6XDS46I Y
  • DTXSID50949617
  • 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).
N verify (what is YN ?)

Natural occurrences edit

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 edit

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

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

Spectral data edit

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 edit

  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. ^ 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 (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.

January 01, 1970
cynaroside, also, known, luteoloside, flavone, flavonoid, like, chemical, compound, glucoside, luteolin, names, iupac, name, glucopyranosyloxy, trihydroxyflavone, systematic, iupac, name, dihydroxyphenyl, hydroxy, trihydroxy, hydroxymethyl, oxan, benzopyran, o. 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 b 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 GlucoluteolinLuteolosideCinaroside7 Glucoluteolin7 GlucosylluteolinLuteolin 7 glucosideLuteolin 7 glucosideLuteolin 7 O glucosideLuteolin 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 NKey PEFNSGRTCBGNAN QNDFHXLGSA N NInChI 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 s1Key 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 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 N verify what is Y N Infobox references Contents 1 Natural occurrences 2 Metabolism 3 Spectral data 4 ReferencesNatural occurrences editIt 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 editFlavone 7 O beta glucosyltransferase adds a glucose to luteolin A cynaroside 7 O glucosidase has been identified in the artichoke 6 Spectral data editUV Vis 7 Lambda max UV 348 260 nm Extinction coefficient log e 4 11 4 23 IR Major absorption bands cm 1 NMR Proton NMR 1H NMR 500 MHz CD3COCD3 D2O d 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 d 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 1References edit 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 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 Flavonoid Aglycones and Glycosides from Teucrium gnaphalodes F A T Barberan M I Gil F Tomas F Ferreres and A Arques J Nat Prod 1985 48 5 pages 859 860 doi 10 1021 np50041a040 Is the Healthiest Part of Dandelion Its Flower 17 April 2014 a b Nublein B Kreis W 2005 Purification and Characterization of a Cynaroside 7 O b D Glucosidase from Cynarae scolymi folium Acta Horticulturae 681 681 413 20 doi 10 17660 ActaHortic 2005 681 58 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 Retrieved from https en wikipedia org w index php title Cynaroside amp oldid 1152505323, wikipedia, wiki, book, books, library,

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