| Synonyms |
2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl-D-glucopyranoside; Cynaroside; Luteoloside; Luteolin 7-glucoside |
| 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 |
| Molecular Weight |
448.39 |
| Molecular Formula |
C21H20O11 |
| Canonical 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 |
| 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 |
| InChIKey |
PEFNSGRTCBGNAN-QNDFHXLGSA-N |
| Boiling Point |
838.10°C at 760 mmHg (est) |
| Melting Point |
240 - 242°C |
| Flash Point |
296.8±27.8 °C |
| Purity |
98% (HPLC) |
| Density |
1.7±0.1 g/cm3 |
| Solubility |
Soluble in dimethylsulfoxid, dimethylformamid, insoluble in ethanol and water |
| Appearance |
Dark Yellow Solid |
| Storage |
Hygroscopic, Refrigerator, under inert atmosphere |
| Complexity |
714 |
| Exact Mass |
448.10056145 |
| Index Of Refraction |
1.740 |
| In Vitro |
Cynaroside inhibited the expression of iNOS, COX-2, TNF-α, and IL-6 in LPS-stimulated hPDL and RAW264.7 cells without cytotoxicity. Furthermore, cynaroside significantly suppressed LPS-induced protein expression of matrix metalloproteinase 3. Additionally, cynaroside prevented LPS-induced NF-κB p65 subunit translocation to the nucleus by inhibiting the phosphorylation and degradation of IκB-α. Moreover, cynaroside could restore the mineralization ability of hPDL cells reduced by LPS. |
| In Vivo |
Building upon a sepsis mouse model, it was observed cynaroside alleviated serum levels of inflammatory factors including IL-1β and TNF-α at 5 and 10 mg/kg. The pathological injury of heart, kidney and lung was remarkedly attenuated as the levels of blood urea nitrogen, creatinine, creatine kinase-MB and lactate dehydrogenase were reduced nearly 2.8-, 2.7-, 2.4-, and 2.5-fold as compared with the sepsis mice, respectively. The research further demonstrated cynaroside suppressed the biomarker of pro-inflammatory macrophage M1 phenotype (iNOS+) and promotes the anti-inflammatory M2 polarization (CD206+) in the injury organs of septic mice. Mechanistic research verified cynaroside inhibited LPS-induced polarization of macrophage into M1 phenotype, which can be highly blocked by Nrf2 inhibitor. Expectedly, Nrf2 and its downstream (Heme oxygenase-1 (HO-1)) was upregulated in injury organs after treating with cynaroside, indicating the involvement of Nrf2 signaling. |
| PSA |
190.28000 |
| Target |
Influenza Virus; DNA/RNA Synthesis; Apoptosis; Parasite; Bacterial; Fungal
IC50:32 nM (RNA polymerase inhibitor) |
| Vapor Pressure |
0.0±3.2 mmHg at 25°C |
| XLogP3-AA |
0.5 |
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