Brevilin ACAS# 16503-32-5 |
- Microhelenin C
Catalog No.:BCN7977
CAS No.:63569-07-3
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 16503-32-5 | SDF | Download SDF |
| PubChem ID | 12302076 | Appearance | White powder |
| Formula | C20H26O5 | M.Wt | 346.4 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Synonyms | 6-Angeloylplenolin; Brevelin A | ||
| Solubility | DMSO : 250 mg/mL (721.67 mM; Need ultrasonic) | ||
| Chemical Name | [(1S,3aR,5R,5aR,8aR,9S,9aR)-1,5,8a-trimethyl-2,8-dioxo-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate | ||
| SMILES | CC=C(C)C(=O)OC1C2C(C(=O)OC2CC(C3C1(C(=O)C=C3)C)C)C | ||
| Standard InChIKey | KUPPZVXLWANEJJ-UXPPPGSFSA-N | ||
| Standard InChI | InChI=1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1 | ||
| 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 | Brevilin A is a strong impetus for the development of selective JAK-STAT inhibitors and therapeutic drugs in order to improve survival of patients with hyperactivated JAKs and STATs. Brevilin A shows antigiardial activity (IC50 = 16.1 μM) and is similarly active in vitro against Entamoeba histolytica (IC50 between 4.5 and 9 μM) and against Plasmodium falciparum (IC50 = 9.42 μM). |
| Targets | JAK | STAT | Antifection |
| In vitro | Antiprotozoal activities of Centipeda minima.[Reference: WebLink]Phytother. Res., 1994, 8(8):436-8.
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| Kinase Assay | Brevilin A, a novel natural product, inhibits janus kinase activity and blocks STAT3 signaling in cancer cells.[Pubmed: 23704931]PLoS One. 2013 May 21;8(5):e63697.Signal abnormalities in human cells usually cause unexpected consequences for individual health. We focus on these kinds of events involved in JAK-STAT signal pathways, especially the ones triggered by aberrant activated STAT3, an oncoprotein which participates in essential processes of cell survival, growth and proliferation in many types of tumors, as well as immune diseases. |
| Structure Identification | Zhongguo Zhong Yao Za Zhi. 2009 Jun;34(12):1520-2.[Chemical constituents from Centipeda minima].[Pubmed: 19777837]To study the chemical constituents from Centipeda minima.
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Brevilin A Dilution Calculator
Brevilin A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8868 mL | 14.4342 mL | 28.8684 mL | 57.7367 mL | 72.1709 mL |
| 5 mM | 0.5774 mL | 2.8868 mL | 5.7737 mL | 11.5473 mL | 14.4342 mL |
| 10 mM | 0.2887 mL | 1.4434 mL | 2.8868 mL | 5.7737 mL | 7.2171 mL |
| 50 mM | 0.0577 mL | 0.2887 mL | 0.5774 mL | 1.1547 mL | 1.4434 mL |
| 100 mM | 0.0289 mL | 0.1443 mL | 0.2887 mL | 0.5774 mL | 0.7217 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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Brevilin A, a novel natural product, inhibits janus kinase activity and blocks STAT3 signaling in cancer cells.[Pubmed:23704931]
PLoS One. 2013 May 21;8(5):e63697.
Signal abnormalities in human cells usually cause unexpected consequences for individual health. We focus on these kinds of events involved in JAK-STAT signal pathways, especially the ones triggered by aberrant activated STAT3, an oncoprotein which participates in essential processes of cell survival, growth and proliferation in many types of tumors, as well as immune diseases. By establishing a STAT3 signal based high-throughput drug screening system in human lung cancer A549 cells, we have screened a library from natural products which contained purified compounds from medicinal herbs. One compound, named Brevilin A, exhibited both strong STAT3 signal inhibition and STAT3 signal dependent cell growth inhibition. Further investigations revealed that Brevilin A not only inhibits STAT3 signaling but also STAT1 signaling for cytokines induced phosphorylation of STAT3 and STAT1 as well as the expression of their target genes. In addition, we found Brevilin A could attenuate the JAKs activity by blocking the JAKs tyrosine kinase domain JH1. The levels of cytokine induced phosphorylation of STATs and other substrates were dramatically reduced by treatment of Brevilin A. The roles of Brevilin A targeting on JAKs activity indicate that Brevilin A may not only be used as a STAT3 inhibitor but also a compound blocking other JAK-STAT hyperactivation. Thus, these findings provided a strong impetus for the development of selective JAK-STAT inhibitors and therapeutic drugs in order to improve survival of patients with hyperactivated JAKs and STATs.
[Chemical constituents from Centipeda minima].[Pubmed:19777837]
Zhongguo Zhong Yao Za Zhi. 2009 Jun;34(12):1520-2.
OBJECTIVE: To study the chemical constituents from Centipeda minima. METHOD: The constituents were isolated by column chromatography on silica gel, Sephadex LH-20 and HPLC-ODS, and identified by spectroscopic methods. RESULT: Ten compounds, (-)-cis-chrysanthenol-O-beta-D-glucopyranoside (1), methy 3,5-dicaffeoylquinate (2), 3,5-di-O-caffeoyl quinicacid (3), tricin (4), 2-amino-4-methyl-pentanoicacid (5), 2-amino-3-phenyl-propionic acid (6), 4-amino-4-carboxychroman-2-one (7), brevilin-A (8), arnicolide C (9), arnicolide D (10) were isolated and identified. CONCLUSION: Compounds 1-7 were isolated from the plant for the first time.
