cirsilineol
cirsilineol Basic information
- Product Name:
- cirsilineol
- Synonyms:
-
- cirsilineol
- 2-(4-Hydroxy-3-methoxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one
- 4',5-Dihydroxy-3',6,7-trimethoxyflavone
- 5,4'-Dihydroxy-6,7,3'-trimethoxyflavone
- 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-1-benzopyran-4-one
- Anisomelin
- 6-Methoxyluteolin 3',7-dimethyl ether
- Eupatrin
- CAS:
- 41365-32-6
- MF:
- C18H16O7
- MW:
- 344.32
- Mol File:
- 41365-32-6.mol
cirsilineol Chemical Properties
- Melting point:
- 147 °C(Solv: benzene (71-43-2))
- Boiling point:
- 585.0±50.0 °C(Predicted)
- Density
- 1.387
- storage temp.
- -20°C
- solubility
- Soluble in DMSO, ethanol and water;
- pka
- 6.31±0.40(Predicted)
- form
- Solid
- color
- Yellow
- Water Solubility
- insoluble in water
- BRN
- 1355108
- InChI
- InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
- InChIKey
- VKOSQMWSWLZQPA-UHFFFAOYSA-N
- SMILES
- C1(C2=CC=C(O)C(OC)=C2)OC2=CC(OC)=C(OC)C(O)=C2C(=O)C=1
- LogP
- 1.670 (est)
cirsilineol Usage And Synthesis
Uses
Cirsilineol, a natural flavone compound, selectively inhibits IFN-γ/STAT1/T-bet signaling in intestinal CD4+ T cells. Cirsilineol has potent immunosuppressive and anti-tumor properties. Cirsilineol significantly ameliorates trinitro-benzene sulfonic acid (TNBS)-induced T-cell-mediated experimental colitis in mice[1].
Definition
ChEBI: A trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 7 and 3' and hydroxy groups at positions 5 and 4' respectively.
in vivo
cirsilineol (3, 10, and 30 mg/kg) significantly ameliorates TNBS-induced Th1-mediated colitis through inhibiting IFN-γ/STAT1/T-bet signaling in CD4+ T cells.
| Animal Model: | 8-10-week-old female C57BL/6, BALB/c and DO11.10 transgenic mice with TNBS (10 mg; 100 μL)[1] |
| Dosage: | 3, 10, 30 mg/kg |
| Administration: | IP; daily; for 11 days |
| Result: | Showed a significant improved effect on the body weights and survival rate of mice. Markedly reduced inflammatory infiltration, restoration of the destructive mucosal architecture and remission of edema. |
target
IFN-γ | IL Receptor | gp120/CD4 | STAT | TGF-β/Smad | JAK | PARP | Caspase | P450 (e.g. CYP17)
References
[1] Yang Sun, et al. Novel immunomodulatory properties of cirsilineol through selective inhibition of IFN-gamma signaling in a murine model of inflammatory bowel disease. Biochem Pharmacol. 2010 Jan 15;79(2):229-38. DOI:10.1016/j.bcp.2009.08.014
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