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Cirsimaritin (Synonyms: 5,4'-Dihydroxy-6,7-dimethoxyflavone)

Catalog No.GC31120 Copy One-Click Copy Product Info

Cirsimaritin is a dimethoxy flavonoid found in plants, it has anticancer potential and shows potent antimicrobial, antioxidant, antispasmodic, activity, and also inhibits cyclooxygenase-1.

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Cirsimaritin Chemical Structure

Cas No.: 6601-62-3

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10mM (in 1mL DMSO)
$138.00
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1mg
$45.00
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5mg
$128.00
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Sample solution is provided at 25 µL, 10mM.



Description of Cirsimaritin

Cirsimaritin is a dimethoxy flavonoid found in plants, it has anticancer potential and shows potent antimicrobial, antioxidant, antispasmodic, activity, and also inhibits cyclooxygenase-1[1-3].

Cirsimaritin significantly decreased cell proliferation in the NCIH-520 cell line, with an IC50 value of 23.29 ± 3.51µM[4]. Cirsimaritin(0–120µg/mL; 20h) inhibited interleukin-6, tumor necrosis factor-α, and NO production in a concentration-dependent manner in lipopolysaccharide (LPS)-stimulated RAW264.7 cells[5]. Cirsimaritin(5-20µg/mL) reduced viral titers and influenza A virus (IAV) RNA and protein synthesis in a dose-dependent manner[6].

Cirsimaritin(10mg/kg; i.g)ffectively prevented DSS-induced colon inflammation in mice by mitigating mucosal damage and inflammatory cell infiltration. It significantly downregulated proinflammatory cytokines such as MMP9, NF-κB, COX-2, and iNOS. Additionally, cirsimaritin reversed DSS-induced effects, including weight loss, colon shortening, tissue damage, increased inflammatory cells, and elevated cytokine secretion[7]. Treatment with cirsimaritin(0.5-1mg/kg; p.o; 8 weeks) reduced the severity of liver injury in the experimental mouse model of metabolic dysfunction-associated fatty liver disease (MAFLD) by inhibiting hepatic steatosis, oxidative stress, inflammation, and liver fibrosis[8].

References:
[1]. Benali T, Jaouadi I, et,al. The Current State of Knowledge in Biological Properties of Cirsimaritin. Antioxidants (Basel). 2022 Sep 19;11(9):1842. doi: 10.3390/antiox11091842. PMID: 36139916; PMCID: PMC9495358.
[2]. Ben Sghaier M, Skandrani I, et,al. Flavonoids and sesquiterpenes from Tecurium ramosissimum promote antiproliferation of human cancer cells and enhance antioxidant activity: a structure-activity relationship study. Environ Toxicol Pharmacol. 2011 Nov;32(3):336-48. doi: 10.1016/j.etap.2011.07.003. Epub 2011 Jul 12. PMID: 22004952.
[3]. Nyiligira E, Viljoen AM, et,al. Phytochemistry and in vitro pharmacological activities of South African Vitex (Verbenaceae) species. J Ethnopharmacol. 2008 Oct 28;119(3):680-5. doi: 10.1016/j.jep.2008.07.004. Epub 2008 Jul 16. PMID: 18678237.
[4]. Pathak G, Singh S, et,al. Cirsimaritin, a lung squamous carcinoma cells (NCIH-520) proliferation inhibitor. J Biomol Struct Dyn. 2021 Jun;39(9):3312-3323. doi: 10.1080/07391102.2020.1763198. Epub 2020 May 13. PMID: 32362196.
[5]. Shin MS, Park JY, et,al. Anti-inflammatory effects and corresponding mechanisms of cirsimaritin extracted from Cirsium japonicum var. maackii Maxim. Bioorg Med Chem Lett. 2017 Jul 15;27(14):3076-3080. doi: 10.1016/j.bmcl.2017.05.051. Epub 2017 May 17. PMID: 28554870.
[6]. sYan H, Wang H, et,al. Cirsimaritin inhibits influenza A virus replication by downregulating the NF-κB signal transduction pathway. Virol J. 2018 May 21;15(1):88. doi: 10.1186/s12985-018-0995-6. PMID: 29783993; PMCID: PMC5963025.
[7]. Alqudah A, Qnais E, et,al. Cirsimaritin Alleviates Dextran Sodium Sulfate-Induced Acute Colitis in Experimental Animals: A Therapeutic Approach for Inflammatory Bowel Disease. Prev Nutr Food Sci. 2024 Mar 31;29(1):31-39. doi: 10.3746/pnf.2024.29.1.31. PMID: 38576881; PMCID: PMC10987388.
[8]. Che DN, Shin JY, et,al. Ameliorative effects of Cirsium japonicum extract and main component cirsimaritin in mice model of high-fat diet-induced metabolic dysfunction-associated fatty liver disease. Food Sci Nutr. 2021 Sep 1;9(11):6060-6068. doi: 10.1002/fsn3.2548. PMID: 34760237; PMCID: PMC8565240.

Protocol of Cirsimaritin

Cell experiment [1]:

Cell lines

NCIH-520 cell line

Preparation Method

Cells were cultured in high glucose DMEM or RPMI media and supplemented with 1% Ab/Am and 10% FBS and placed in a CO2 incubator at 37 ℃ temperature in 95% humidity. Cells were seeded in a sterile 96-well flat-bottom cell culture plates with approximately 2 × 103 cells/well in each well, and the plates were incubated for 24h in CO2 incubator. After 24h of incubation, cells were treated with different concentrations of cirsimaritin, ranging from 0.1-100μM and followed by incubation for 24h.

Reaction Conditions

0.1-100μM; 24h

Applications

Cirsimaritin significantly decreased cell proliferation in the NCIH-520 cell line, with an IC50 value of 23.29 ± 3.51µM.

Animal experiment [2]:

Animal models

Male Swiss albino mice

Preparation Method

Mice were given a regimen of cirsimaritin, which was administered at a daily dose of 10mg/kg body weight (BW) through gavage, before they were exposed to DSS (4% DSS in their drinking water for 6 days).

Dosage form

10mg/kg; i.g

Applications

Cirsimaritin maintains BW (body weight) and reduces DAI (disease activity index) in mice with DSS (dextran sulfate sodium)-induced colitis.

References:
[1]. Pathak G, Singh S, et,al. Cirsimaritin, a lung squamous carcinoma cells (NCIH-520) proliferation inhibitor. J Biomol Struct Dyn. 2021 Jun;39(9):3312-3323. doi: 10.1080/07391102.2020.1763198. Epub 2020 May 13. PMID: 32362196.
[2].Alqudah A, Qnais E, et,al. Cirsimaritin Alleviates Dextran Sodium Sulfate-Induced Acute Colitis in Experimental Animals: A Therapeutic Approach for Inflammatory Bowel Disease. Prev Nutr Food Sci. 2024 Mar 31;29(1):31-39. doi: 10.3746/pnf.2024.29.1.31. PMID: 38576881; PMCID: PMC10987388.

Chemical Properties of Cirsimaritin

Cas No. 6601-62-3 SDF
Synonyms 5,4'-Dihydroxy-6,7-dimethoxyflavone
Canonical SMILES O=C1C=C(C2=CC=C(O)C=C2)OC3=CC(OC)=C(OC)C(O)=C13
Formula C17H14O6 M.Wt 314.29
Solubility DMSO : 22.73 mg/mL (72.32 mM; Need ultrasonic) Storage Store at -20°C,protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Cirsimaritin

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 3.1818 mL 15.9089 mL 31.8177 mL
5 mM 636.4 μL 3.1818 mL 6.3635 mL
10 mM 318.2 μL 1.5909 mL 3.1818 mL
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Review for Cirsimaritin

Average Rating: 5 ★★★★★ (Based on Reviews and 20 reference(s) in Google Scholar.)

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