| Identification | Back Directory | [Name]
cirsilineol | [CAS]
41365-32-6 | [Synonyms]
Eupatrin
Fastigenin
NSC 633556
Anisomelin
cirsilineol
6-Methoxyluteolin 3',7-dimethyl ether
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
2-(4-Hydroxy-3-methoxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy- | [Molecular Formula]
C18H16O7 | [MDL Number]
MFCD01083015 | [MOL File]
41365-32-6.mol | [Molecular Weight]
344.32 |
| Chemical Properties | Back Directory | [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; | [form ]
neat | [pka]
6.31±0.40(Predicted) | [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) |
| Hazard Information | Back Directory | [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.
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| [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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