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Luteoloside is a natural product of the flavonoid class. It acts as an inhibitor of potent influenza RNA-dependent RNA polymerase (IC50 = 32 nM). Also as Luteoloside inhibits H2O2-induced apoptosis, it is cytoprotective against oxidative stress-induced cardiovascular diseases. Furthermore, Luteoloside has various other bioactivities such as antifungal, antibacterial, anticancer, antioxidant and anti-inflammatory effects.
Physicochemical Properties
| Molecular Formula | C21H20O11 |
| Molecular Weight | 448.3769 |
| Exact Mass | 448.1 |
| CAS # | 5373-11-5 |
| PubChem CID | 5280637 |
| Appearance | Light yellow to green yellow solid powder |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 838.1±65.0 °C at 760 mmHg |
| Melting Point | 256 - 258 °C |
| Flash Point | 296.8±27.8 °C |
| Vapour Pressure | 0.0±3.2 mmHg at 25°C |
| Index of Refraction | 1.740 |
| LogP | -0.09 |
| Hydrogen Bond Donor Count | 7 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 32 |
| Complexity | 714 |
| Defined Atom Stereocenter Count | 5 |
| 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 |
| InChi Key | PEFNSGRTCBGNAN-QNDFHXLGSA-N |
| InChi Code | 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 |
| Chemical 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 |
| Synonyms | Cynaroside;Luteolin 7-glucoside; Cinaroside; Luteolin-7-glucoside; Luteolin 7-O-glucoside; Luteolin-7-O-glucoside |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | RNA polymerase inhibitor（IC50=32 nM） |
| ln Vitro |
Cynaroside reduces liver inflammatory damage linked to sepsis and promotes the phenotypic shift of macrophages from pro-inflammatory M1 to anti-inflammatory M2. By preventing PKM2 from translocating to the nucleus, encouraging the formation of PKM2 tetramers, and inhibiting PKM2 phosphorylation at Y105 both in vivo and in vitro, cynaroside decreases the binding of PKM2 to hypoxia-inducible factor-1α (HIF-1α). In septic liver, cynaroside prevents the hyperacetylation of HMGB1 due to glycolysis, restores pyruvate kinase activity, and inhibits proteins related to glycolysis such as PFKFB3, HK2, and HIF-1α. By reducing the production of reactive oxygen species and preventing caspase activation in the mitochondrial and death receptor pathways, cynaroside shields H9c2 cells from H2O2-induced apoptosis. By controlling the expression of JNK, P53, and the Bcl-2 protein, cynaroside preserves mitochondrial function[2][3]. |
| ln Vivo | Cynaroside (i.p.; 5 mg/kg) inhibits PKM2's binding to hypoxia-inducible factor-1α (HIF-1α) by preventing PKM2 from translocating to the nucleus, encouraging the formation of PKM2 tetramers, and preventing PKM2 from being phosphorylated at Y105[2]. |
| Cell Assay |
Cell Line: H9c2 cells Concentration: 25, 50, 100 μg/mL Incubation Time: 4 h Result: Protected H9c2 cells from oxidative stress-induced cell injury. |
| Animal Protocol |
Animal Model: Mice model of sepsis[2] Dosage: 5mg/kg Administration: Cynaroside (i.p.; 5mg/kg) Result: Inhibited PKM2 dimer formation in liver of septic mice. |
| References |
[1]. Unraveling the Anti-Influenza Effect of Flavonoids: Experimental Validation of Luteolin and its Congeners as Potent Influenza Endonuclease Inhibitors. Eur J Med Chem. 22 August 2020, 112754. [2]. Cynaroside prevents macrophage polarization into pro-inflammatory phenotype and alleviates cecal ligation and puncture-induced liver injury by targeting PKM2/HIF-1α axis. Fitoterapia. 2021 Jul;152:104922. [3]. Protective effects of cynaroside against H₂O₂-induced apoptosis in H9c2 cardiomyoblasts. J Cell Biochem. 2011 Aug;112(8):2019-29. [4]. Cynaroside inhibits Leishmania donovani UDP-galactopyranose mutase and induces reactive oxygen species to exert antileishmanial response. Biosci Rep. 2021 Jan 29;41(1):BSR20203857. |
| Additional Infomation |
Luteolin 7-O-beta-D-glucoside is a glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and a plant metabolite. It is a beta-D-glucoside, a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a luteolin. It is a conjugate acid of a luteolin 7-O-beta-D-glucoside(1-). Cynaroside has been reported in Coreopsis lanceolata, Sonchus fruticosus, and other organisms with data available. See also: Cynara scolymus leaf (part of); Lonicera japonica flower (part of); Chamaemelum nobile flower (part of). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~83.33 mg/mL (~185.85 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.64 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.64 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: 16.67 mg/mL (37.18 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2303 mL | 11.1513 mL | 22.3025 mL | |
| 5 mM | 0.4461 mL | 2.2303 mL | 4.4605 mL | |
| 10 mM | 0.2230 mL | 1.1151 mL | 2.2303 mL |