CirsimaritinCAS# 6601-62-3 |
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| Cas No. | 6601-62-3 | SDF | Download SDF |
| PubChem ID | 188323 | Appearance | Yellow powder |
| Formula | C17H14O6 | M.Wt | 314.3 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxychromen-4-one | ||
| SMILES | COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC=C(C=C3)O)O)OC | ||
| Standard InChIKey | ZIIAJIWLQUVGHB-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C17H14O6/c1-21-14-8-13-15(16(20)17(14)22-2)11(19)7-12(23-13)9-3-5-10(18)6-4-9/h3-8,18,20H,1-2H3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Cirsimaritin has antibacterial, anti- inflammation, anti-tumor, antioxidant, renal protection and so on. 2. Cirsimaritin has potential use in patients with congestive heart failure, it can mitigate cardiac remodeling and left ventricular dysfunction through augmenting myocardial autophagy and decreasing matrix metalloproteinase-2&9 activities. 3. Cirsimaritin inhibits the growth of tumor cells and induced mitochondrial apoptosis in human gallbladder carcinoma cell line (GBC-SD), it triggers endoplasmic reticulum (ER) stress and down-regulates the phosphorylation of Akt. 4. Cirsimaritin increases tyrosinase activity and melanin content in murine B16F10 melanoma cells by activation of CREB as well as upregulation of MITF and tyrosinase expression in a dose-dependent manner;support the putative application of cirsimaritin in ultraviolet photoprotection and hair coloration treatments. 5. Cirsimaritin shows moderate anti-proliferative activity against COLO-205 cells with IC 50 values of 13.1uM. |
| Targets | Tyrosinase | cAMP | PKA | Akt | NADPH-oxidase | Calcium Channel | TNF-α | Antifection |
Cirsimaritin Dilution Calculator
Cirsimaritin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.1817 mL | 15.9084 mL | 31.8167 mL | 63.6335 mL | 79.5418 mL |
| 5 mM | 0.6363 mL | 3.1817 mL | 6.3633 mL | 12.7267 mL | 15.9084 mL |
| 10 mM | 0.3182 mL | 1.5908 mL | 3.1817 mL | 6.3633 mL | 7.9542 mL |
| 50 mM | 0.0636 mL | 0.3182 mL | 0.6363 mL | 1.2727 mL | 1.5908 mL |
| 100 mM | 0.0318 mL | 0.1591 mL | 0.3182 mL | 0.6363 mL | 0.7954 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects.[Pubmed:20804824]
Fitoterapia. 2011 Mar;82(2):168-72.
Two new 5-O-glucosylflavones, 5-O-beta-D-glucopyranosyl Cirsimaritin (1) and 5, 4'-O-beta-D-diglucopyranosyl Cirsimaritin (2), four known flavonoids, cirsimarin (3), Cirsimaritin (4), salvigenin (5), 4', 5-dihydroxy-7-methoxyflavone (6), and a norisoprenoid, vomifoliol (7), have been isolated from the aerial parts of Microtea debilis. All isolates were tested for cytotoxicity in human cancer cell lines (Hep G2, COLO 205, and HL-60) and anti-inflammatory activities in LPS-treated RAW264.7 macrophages. Compound 6 was found to be a potent inhibitor to nitrite production in macrophages. Compounds 2, 4, 6, and 7 showed moderate anti-proliferative activity against COLO-205 cells with IC(50) values of 7.1, 13.1, 6.1, and 6.8 muM, respectively.
Reactive oxygen species-mediated endoplasmic reticulum stress and mitochondrial dysfunction contribute to cirsimaritin-induced apoptosis in human gallbladder carcinoma GBC-SD cells.[Pubmed:20359814]
Cancer Lett. 2010 Sep 28;295(2):252-9.
In this study, the anticancer effect of Cirsimaritin, a natural flavonoid, against human gallbladder carcinoma cell line GBC-SD and the underlying mechanisms were investigated. Cirsimaritin inhibited the growth of tumor cells and induced mitochondrial apoptosis in GBC-SD cells. In addition, Cirsimaritin triggered endoplasmic reticulum (ER) stress and down-regulated the phosphorylation of Akt, while knock-down of CHOP dramatically abrogated the inactivation of Akt and reversed the pro-apoptotic effect of Cirsimaritin. Furthermore, Cirsimaritin provoked the generation of reactive oxygen species in GBC-SD cells, while the antioxidant N-acetyl cysteine almost completely blocked the activation of ER stress and apoptosis, suggesting Cirsimaritin-induced reactive oxygen species is an early event that triggers ER stress mitochondrial apoptotic pathways in GBC-SD cells.
Inhibition of formyl-methionyl-leucyl-phenylalanine-stimulated respiratory burst by cirsimaritin involves inhibition of phospholipase D signaling in rat neutrophils.[Pubmed:12237743]
Naunyn Schmiedebergs Arch Pharmacol. 2002 Oct;366(4):307-14.
In this study, the cellular localization of the inhibitory effect of a natural flavonoid Cirsimaritin against formyl-methionyl-leucyl-phenylalanine (fMLP)-induced respiratory burst in rat neutrophils was investigated. Cirsimaritin concentration-dependently inhibited the superoxide anion (O(*-)(2))generation and O(2) consumption (IC(50) 11.5+/-2.2 micro M and 17.0+/-3.9 micro M, respectively) of neutrophils. Cirsimaritin did not reduce, but slightly enhanced the O(*-)(2) generation in phorbol 12-myristate 13-acetate (PMA)-activated or arachidonic acid-stimulated NADPH oxidase preparation as well as during the autoxidation of dihydroxyfumaric acid. Cirsimaritin did not elevate cellular cAMP levels, and only partially inhibited the fMLP-induced [Ca(2+)](i) changes in the presence or absence of extracellular Ca(2+). The phosphorylation of protein tyrosine, extracellular signal-regulated protein kinase and Akt caused by fMLP were attenuated by Cirsimaritin in a concentration-dependent manner. In contrast, Cirsimaritin had no effect on the phosphorylation of p38 mitogen-activated protein kinase. Cirsimaritin produced a concentration-dependent reduction in the formation of phosphatidic acid and phosphatidylethanol, in the presence of ethanol, from fMLP-stimulated neutrophils (IC(50) 15.1+/-6.5 micro M and 15.6+/-3.4 micro M, respectively), but did not affect the phosphatidylethanol formation in response to PMA. Under the similar concentration range, Cirsimaritin attenuated the membrane translocation of ARF and Rho A. However, the GTPgammaS-stimulated membrane-associated ARF and Rho in cell lysate were unaffected by Cirsimaritin. Collectively, these results indicate that the inhibition of fMLP-induced respiratory burst by Cirsimaritin in rat neutrophils is likely mainly through the blockade of phospholipase D signaling pathway.
Melanogenesis-inducing effect of cirsimaritin through increases in microphthalmia-associated transcription factor and tyrosinase expression.[Pubmed:25903150]
Int J Mol Sci. 2015 Apr 20;16(4):8772-88.
The melanin-inducing properties of Cirsimaritin were investigated in murine B16F10 cells. Cirsimaritin is an active flavone with methoxy groups, which is isolated from the branches of Lithocarpus dealbatus. Tyrosinase activity and melanin content in murine B16F10 melanoma cells were increased by Cirsimaritin in a dose-dependent manner. Western blot analysis revealed that tyrosinase, tyrosinase-related protein (TRP) 1, TRP2 protein levels were enhanced after treatment with Cirsimaritin for 48 h. Cirsimaritin also upregulated the expression of microphthalmia-associated transcription factor (MITF) after 24 h of treatment. Furthermore, Cirsimaritin induced phosphorylation of cyclic adenosine monophosphate (cAMP) response element-binding protein (CREB) in a dose-dependent manner after treatment for 15 min. The Cirsimaritin-mediated increase of tyrosinase activity was significantly attenuated by H89, a cAMP-dependent protein kinase A inhibitor. These findings indicate that Cirsimaritin stimulates melanogenesis in B16F10 cells by activation of CREB as well as upregulation of MITF and tyrosinase expression, which was activated by cAMP signaling. Finally, the melanogenic effect of Cirsimaritin was confirmed in human epidermal melanocytes. These results support the putative application of Cirsimaritin in ultraviolet photoprotection and hair coloration treatments.
