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| verifiedrevid = 414762079 |
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| verifiedrevid = 444296203 |
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| Name = Cynaroside |
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| Name = Cynaroside |
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| Reference =<!--<ref></ref> --> |
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| Reference =<!--<ref></ref> --> |
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| ImageFile = Cynaroside.svg |
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| ImageFile = Cynaroside.svg |
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| ImageSize = 300px |
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| ImageSize = 300px |
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| IUPACName = 7-(β-<small>D</small>-Glucopyranosyloxy)-3′,4′,5-trihydroxysexflavone |
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| IUPACName = 2-(3,4-dihydroxyphenyl)-5-hydroxy-7-oxychromen-4-one |
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| SystematicName = 2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-{oxy}-4''H''-1-benzopyran-4-one |
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| OtherNames = Glucoluteolin<br>Luteoloside<br>Cinaroside<br>7-Glucoluteolin<br>7-Glucosylluteolin<br>Luteolin 7-glucoside<br>Luteolin-7-glucoside<br>Luteolin 7-O-glucoside<br>Luteolin-7-O-glucoside |
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| OtherNames = Glucoluteolin<br>Luteoloside<br>Cinaroside<br>7-Glucoluteolin<br>7-Glucosylluteolin<br>Luteolin 7-glucoside<br>Luteolin-7-glucoside<br>Luteolin 7-O-glucoside<br>Luteolin-7-O-glucoside |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 68321-11-9 |
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| CASNo = 5373-11-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 98J6XDS46I |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C03951 |
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| PubChem = 5280637 |
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| PubChem = 5280637 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| 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 |
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| ChemSpiderID = 4444241 |
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| SMILES = C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O4((((O4)CO)O)O)O)O)O)O |
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| 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 |
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| InChIKey = PEFNSGRTCBGNAN-QNDFHXLGBE |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = PEFNSGRTCBGNAN-QNDFHXLGSA-N |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 27994 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>21</sub>H<sub>20</sub>O<sub>11</sub> |
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| Formula = C<sub>21</sub>H<sub>20</sub>O<sub>11</sub> |
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| MolarMass = 448.37 g/mol |
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| MolarMass = 4488.37 g/mol |
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| ExactMass = 448.100561 |
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| Appearance = Yellow amorphous powder |
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| Appearance = Yellow amorphous powder |
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| Density = |
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| Density = |
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| MeltingPtC = 266 to 268 |
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| MeltingPt = 266–268ºC |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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'''Cynaroside''' (also known as '''luteoloside''') is a ], a flavonoid-like chemical compound. It is a 7-O-] of ]. |
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'''Cynaroside''' is a ], a flavonoid-like chemical compound. It is a 7-O-] of ] and can be found in ], in '']'' and '']''<ref></ref> in '']'' and '']''<ref></ref>, in the bamboo '']''<ref></ref> and in '']'' (artichoke)<ref name="Nüβlein"></ref>. |
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== Natural occurrences == |
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==Metabolism== |
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It can be found in '']'' and '']''<ref>{{cite journal |doi=10.1007/BF02254816 |title=Cynaroside content of the plants ''Ferula varia'' and ''F. Foetida'' |year=1997 |last1=Yuldashev |first1=M. P. |journal=Chemistry of Natural Compounds |volume=33 |issue=5 |pages=597–8|s2cid=45802688 }}</ref> in '']'' and '']'',<ref>{{cite journal |doi=10.1007/BF00564462 |title=Cynaroside and luteolin from Campanula persicifolia and C. Rotundifolia |year=1972 |last1=Teslov |first1=L. S. |last2=Teslov |first2=S. V. |journal=Chemistry of Natural Compounds |volume=8 |pages=117|doi-access=free }}</ref> in the bamboo '']'',<ref>{{cite journal |doi=10.1021/jf0001637 |title=Evaluation of Antioxidant and Prooxidant Activities of Bamboo ''Phyllostachys nigra'' Var. ''Henonis'' Leaf Extract in Vitro |year=2000 |last1=Hu |first1=Chun |last2=Zhang |first2=Ying |last3=Kitts |first3=David D. |journal=Journal of Agricultural and Food Chemistry |volume=48 |issue=8 |pages=3170–6 |pmid=10956087}}</ref> and in '']''.<ref>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}}</ref> |
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] adds a glucose to ]. |
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; In food |
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A ] has been identified in the artichoke<ref name="Nüβlein"/>. |
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It can be found in ] (the highest concentration in the flowers,<ref>{{cite web | url=https://wildfoodism.com/2014/04/17/is-the-healthiest-part-of-dandelion-its-flower/ | title=Is the Healthiest Part of Dandelion Its Flower? | date=17 April 2014 }}</ref> but also in the roots) and in '']'' (artichoke).<ref name="Nüβlein">{{cite journal |url=http://www.actahort.org/books/681/681_58.htm |title=Purification and Characterization of a Cynaroside 7-O-β-D-Glucosidase from Cynarae scolymi folium |journal=Acta Horticulturae |first1=B |last1=Nüβlein |first2=W |last2=Kreis |year=2005 |volume=681 |issue=681 |pages=413–20|doi=10.17660/ActaHortic.2005.681.58 }}</ref> |
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== Metabolism == |
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] adds a glucose to ]. |
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A ] has been identified in the artichoke.<ref name="Nüβlein"/> |
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==Spectral datas== |
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== Spectral data == |
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! {{Chemical datatable header}} | ]<ref>{{cite journal |doi=10.1016/j.phytochem.2009.06.006 |title=Neural cell protective compounds isolated from Phoenix hanceana var. Formosana |year=2009 |last1=Lin |first1=Yi-Pei |last2=Chen |first2=Tai-Yuan |last3=Tseng |first3=Hsiang-Wen |last4=Lee |first4=Mei-Hsien |last5=Chen |first5=Shui-Tein |journal=Phytochemistry |volume=70 |issue=9 |pages=1173–81 |pmid=19628235}}</ref> |
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| Major absorption bands |
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| Major absorption bands |
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| ] <!-- Link to image of spectrum --> |
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| ] <!-- Link to image of spectrum --> |
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| 1H-NMR (500 MHz, CD3COCD3 + D2O):<br /> |
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| 1H-NMR (500 MHz, CD3COCD3 + D2O):<br /> |
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δ 3.42 (1H, t, J = 9.0 Hz, H-4′), 3.49 <br /> |
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δ 3.42 (1H, t, J = 9.0 Hz, H-4′), 3.49 <br /> |
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(1H, t, J = 9.0 Hz, H-2″), 3.56 <br /> |
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(1H, t, J = 9.0 Hz, H-2″), 3.56 <br /> |
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(1H, t, J = 9.0 Hz, H-3″), 3.60 (1H, m, H-5″)<br /> |
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(1H, t, J = 9.0 Hz, H-3″), 3.60 (1H, m, H-5″)<br /> |
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, 3.68 (1H, dd, J = 12.2, 5.6 Hz, H-6a″), <br /> |
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, 3.68 (1H, dd, J = 12.2, 5.6 Hz, H-6a″), <br /> |
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3.85 (1H, dd, J = 12.2, 1.8 Hz, H-6b″), <br /> |
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3.85 (1H, dd, J = 12.2, 1.8 Hz, H-6b″), <br /> |
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5.10 (1H, d, J = 7.8 Hz, H-1″), 6.44 <br /> |
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5.10 (1H, d, J = 7.8 Hz, H-1″), 6.44 <br /> |
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(1H, d, J = 1.8 Hz, H-6), 6.63 (1H, s, H-3), <br /> |
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(1H, d, J = 1.8 Hz, H-6), 6.63 (1H, s, H-3), <br /> |
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6.83 (1H, d, J = 1.8 Hz, H-8), 6.95 <br /> |
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6.83 (1H, d, J = 1.8 Hz, H-8), 6.95 <br /> |
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(1H, d, J = 8.0 Hz, H-5′), 7.41 <br /> |
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(1H, d, J = 8.0 Hz, H-5′), 7.41 <br /> |
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(1H, d, J = 8.0 Hz, H-6′), 7.43 (1H, bs, H-2′) |
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(1H, d, J = 8.0 Hz, H-6′), 7.43 (1H, bs, H-2′) |
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| ] <!-- Link to image of spectrum --> |
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| ] <!-- Link to image of spectrum --> |
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| 13C-NMR (125 MHz, CD3COCD3 + D2O):<br /> |
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| 13C-NMR (125 MHz, CD3COCD3 + D2O):<br /> |
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δ 61.7 (C-6″), 70.3 (C-4″), 73.8 (C-2″), <br /> |
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δ 61.7 (C-6″), 70.3 (C-4″), 73.8 (C-2″), <br /> |
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76.8 (C-3″), 77.4 (C-5″), 95.8 (C-8), 100.5 <br /> |
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76.8 (C-3″), 77.4 (C-5″), 95.8 (C-8), 100.5 <br /> |
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| Masses of <br>main fragments |
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| Masses of <br>main fragments |
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Reference<ref></ref> |
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==References== |
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== References == |
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{{Reflist}} |
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{{Reflist}} |
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{{Natural-phenol-stub}} |
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