Cirsilineol

Names

[ Name ]:
Cirsilineol

[Synonym ]:
4',5-Dihydroxy-3',6,7-trimethoxyflavone
5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxychromen-4-one
Cirsilineol

Biological Activity

[Description]:

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].

[Related Catalog]:

Signaling Pathways >> Stem Cell/Wnt >> STAT

Research Areas >> Cancer

Signaling Pathways >> Immunology/Inflammation >> IFNAR

Signaling Pathways >> JAK/STAT Signaling >> STAT

Research Areas >> Inflammation/Immunology

[In Vitro]

Cirsilineol (0.1-10 μM; 96 hours) single mixed lymphocyte reaction and Con A-induced T-cell proliferation in a dose-dependent manner. Cirsilineol (10 μM) does not affect T lymphocyte's viability. The inhibition of cirsilineol (10 μM) on T-cell proliferation is not due to a cytotoxic activity[1]. Cirsilineol (1-10 μM; pretreatment for 3 hours) completely inhibits IFN-γ-induced Tyr701 phosphorylation of STAT1 and JAK2 activation[1]. Cell Proliferation Assay[1] Cell Line: Splenocytes Concentration: 0.1, 1, 10 μM Incubation Time: 96 hours Result: Inhibited single mixed lymphocyte reaction and Concanavalin A (Con A; 5 μg/mL; for 72 h)-induced T-cell proliferation in a dose-dependent manner. Suppressed OVA323-339-specific CD4+ T-cell proliferation. Western Blot Analysis[1] Cell Line: Splenic CD4+ T cells Concentration: 1, 5, 10 μM Incubation Time: Pretreatment for 3 hours Result: Completely inhibited IFN-γ-induced (25 ng; 30 mins) Tyr701 phosphorylation of STAT1 and JAK2 activation. Suppressed IFN-γ-induced (25 ng; 12 hours) Th1-specific transcription factor T-bet.

[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.

[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.

Chemical & Physical Properties

[ Density]:
1.387g/cm3

[ Boiling Point ]:
585ºC at 760 mmHg

[ Molecular Formula ]:
C₁₈H₁₆O₇

[ Molecular Weight ]:
344.31500

[ Flash Point ]:
215.2ºC

[ Exact Mass ]:
344.09000

[ PSA ]:
98.36000

[ LogP ]:
2.89700

[ Index of Refraction ]:
1.627

[ Storage condition ]:
?20°C

MSDS

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Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2914509090

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914509090

[ Summary ]:
HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

Articles

[Determination of flavonoids in buds of Herba Artemisiae Scopariae by HPLC].

Zhongguo Zhong Yao Za Zhi 30(8) , 591-4, (2005)

To develop a quantitative method for the determination of four flavonoids in buds of Herba Artemisiae Scopariae.The sample was extracted by ultrasonic with ethyl acetate for 30 minutes and separated o...

Analysis of vervain flavonoids by HPLC/Diode array detector method. Its application to quality control.

J. Agric. Food Chem. 47(11) , 4579-82, (1999)

A reversed-phase HPLC procedure is proposed for the determination of seven flavonoids (luteolin, nepetin, hispidulin, jaceosidin, cirsimaritin, cirsilineol, and eupatorin) in vervain samples. A simple...

[Studies on chemical constituents in buds of Artemisia scoparia].

Zhongguo Zhong Yao Za Zhi 27(3) , 202-4, (2002)

To investigate the chemical constituents in flower buds of Artemisia scoparia.The constituents were separated and purified by means of various chromatographic techniques, and their structures were det...