Cirsiliol

Names

[ Name ]:
Cirsiliol

[Synonym ]:
5,3',4'-Trihydroxy-6,7-dimethoxyflavone
2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one
6,7-dimethoxy-5,3',4'-trihydroxyflavone
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-
3',4',5-Trihydoxy-6,7-dimethoxyflavone
2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one
6-Hydroxyluteolin-6,7-dimethyl ether
3',4',5-Trihydroxy-6,7-dimethoxyflavone
Cirsiliol

Biological Activity

[Description]:

Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

Research Areas >> Neurological Disease

Natural Products >> Flavonoids

[Target]

Target: 5-lipoxygenase[1]

[In Vitro]

In concentrations from 0.01 to 300 μM, cirsiliol causes concentration-dependent relaxation of rat isolated ileum. Cirsiliol may inhibit Ca2+ influx but stimulates Ca2+ release from intracellular stores[1]. Treatment with rhamnetin or cirsiliol reduces the proliferation of NSCLC cells through the suppression of radiation-induced Notch-1 expression[2].

[In Vivo]

In xenograft mouse model, tumor volume is significantly reduced by combinational treatment with irradiation and rhamnetin or cirsiliol compared with irradiation alone[2].

[Cell Assay]

NSCLC, NCI-H1299, NCI-H460, WI-26 VA4 and MRC-5 cell lines are exposed to a single dose of γ-rays. Cells are then treated with rhamnetin and cirsiliol (5, 10, 15, 20, 25 μM) dissolved in DMSO for 4 h[2].

[Animal admin]

Mice[1] BALB/c athymic nude mice are injected with 2×106 NCI-H1299 cells. When the tumor has acquired a minimal volume of 200 mm3, DMSO or Cirsiliol (200 μg/kg body weight) is administered intraperitoneally every day for 25 days. The animals are also irradiated with 10 Gy once a week for 3 weeks. On day 25, the tumors are excised and subjected to further analyses[1].

[References]

[1]. Mustafa EH, et al. Effects of cirsiliol, a flavone isolated from Achillea fragrantissima, on rat isolated ileum. Gen Pharmacol. 1992 May;23(3):555-60.

[2]. Kang J, et al. Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. J Biol Chem. 2013 Sep 20;288(38):27343-57.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
616.1±55.0 °C at 760 mmHg

[ Melting Point ]:
280-281.5℃ (methanol )

[ Molecular Formula ]:
C₁₇H₁₄O₇

[ Molecular Weight ]:
330.289

[ Flash Point ]:
230.8±25.0 °C

[ Exact Mass ]:
330.073944

[ PSA ]:
109.36000

[ LogP ]:
2.27

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.671

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DJ3011100

[ HS Code ]:
2914509090

Synthetic Route

Click to get detail synthetic route

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

[Chemical constituents of Eupatorium lindleyanum].

Zhongguo Zhong Yao Za Zhi 37(7) , 937-40, (2012)

To study chemical constituents of Eupatorium lindleyanum. Ethyl acetate extractive fractions were separated with silica gel and Sephadex LH-20 by column chromatography, and their structures were ident...

[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...

Potent and selective 5-lipoxygenase inhibitors: cirsiliol and AA-861.

Adv. Prostaglandin. Thromboxane. Leukot. Res. 15 , 217-9, (1985)