PhellopterinCAS# 2543-94-4 |
Quality Control & MSDS
3D structure
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| Cas No. | 2543-94-4 | SDF | Download SDF |
| PubChem ID | 98608 | Appearance | Light yellow powder |
| Formula | C17H16O5 | M.Wt | 300.3 |
| Type of Compound | Coumarins | Storage | Desiccate at -20°C |
| Solubility | Soluble in acetonitrile and chloroform | ||
| Chemical Name | 4-methoxy-9-(3-methylbut-2-enoxy)furo[3,2-g]chromen-7-one | ||
| SMILES | CC(=CCOC1=C2C(=C(C3=C1OC(=O)C=C3)OC)C=CO2)C | ||
| Standard InChIKey | BMLZFLQMBMYVHG-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C17H16O5/c1-10(2)6-8-21-17-15-12(7-9-20-15)14(19-3)11-4-5-13(18)22-16(11)17/h4-7,9H,8H2,1-3H3 | ||
| 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 | Phellopterin is a partial agonist of the central benzodiazepine receptors in vitro; it shows cytotoxic effect on RAW264.7 cell at the concentration from 40 to 400 μM. Phellopterin reduces TNF-alpha-induced VCAM-1 expression through regulation of the Akt and PKC pathway, which contributes to inhibit the adhesion of monocytes to endothelium. |
| Targets | NO | Akt | PKC | TNF-α | GABA Receptor | ERK |
| In vitro | Hesperidin, hesperidin methyl chalone and phellopterin from Poncirus trifoliata (Rutaceae) differentially regulate the expression of adhesion molecules in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells.[Pubmed: 18387509 ]Int Immunopharmacol. 2008 May;8(5):670-8.The fruits of Poncirus trifoliata (L.) are widely used in Oriental medicine to treat allergic inflammation. Recently, several active compounds including hesperidin, hesperidin methyl chalone and Phellopterin from P. trifoliata (Rutaceae) were isolated and characterized. Characterisation of the furanocoumarin phellopterin as a rat brain benzodiazepine receptor partial agonist in vitro.[Pubmed: 8971802]Neurosci Lett. 1996 Nov 29;219(3):151-4.
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| Cell Research | Biotransformation products of phellopterin by rat liver microsomes and the inhibition on NO production in LPS-activated RAW264.7 cells.[Pubmed: 23046467]J Asian Nat Prod Res. 2012;14(10):956-65.
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Phellopterin Dilution Calculator
Phellopterin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.33 mL | 16.65 mL | 33.3 mL | 66.6001 mL | 83.2501 mL |
| 5 mM | 0.666 mL | 3.33 mL | 6.66 mL | 13.32 mL | 16.65 mL |
| 10 mM | 0.333 mL | 1.665 mL | 3.33 mL | 6.66 mL | 8.325 mL |
| 50 mM | 0.0666 mL | 0.333 mL | 0.666 mL | 1.332 mL | 1.665 mL |
| 100 mM | 0.0333 mL | 0.1665 mL | 0.333 mL | 0.666 mL | 0.8325 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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Hesperidin, hesperidin methyl chalone and phellopterin from Poncirus trifoliata (Rutaceae) differentially regulate the expression of adhesion molecules in tumor necrosis factor-alpha-stimulated human umbilical vein endothelial cells.[Pubmed:18387509]
Int Immunopharmacol. 2008 May;8(5):670-8.
The fruits of Poncirus trifoliata (L.) are widely used in Oriental medicine to treat allergic inflammation. Recently, several active compounds including hesperidin, hesperidin methyl chalone and Phellopterin from P. trifoliata (Rutaceae) were isolated and characterized. The goal of this study was to investigate the differential effect of hesperidin, hesperidin methyl chalone and Phellopterin derived from P. trifoliata (Rutaceae) on the induction of intercellular adhesion molecule-1 (ICAM-1) and vascular cell adhesion molecule-1 (VCAM-1) by TNF-alpha and the possible molecular mechanisms by which they differentially regulate ICAM-1 and VCAM-1 expressions. Stimulation of human umbilical vein endothelial cells (HUVECs) with TNF-alpha resulted in the increase of ICAM-1 and VCAM-1 expressions, while pretreatment with the three components completely inhibited VCAM-1 expression in a dose-dependent manner but had no effect on ICAM-1 expression. All three compounds failed to block TNF-alpha-induced phosphorylation of ERK1/2, which is involved in regulating ICAM-1 production by TNF-alpha. Furthermore, they efficiently inhibited the phosphorylation of Akt and PKC, suggesting that Akt or PKC pathways are an important target by which these compounds regulate TNF-alpha-induced VCAM-1 but not ICAM-1. Additionally, treatment with these chemicals also inhibited U937 monocyte adhesion to HUVECs stimulated with TNF-alpha. Interestingly, the inhibitory effect of hesperidin, hesperidin methyl chalone and Phellopterin on monocyte adhesion to HUVECs was recapitulated by transfecting cells with VCAM-1 siRNA. Taken together, hesperidin, hesperidin methyl chalone and Phellopterin reduce TNF-alpha-induced VCAM-1 expression through regulation of the Akt and PKC pathway, which contributes to inhibit the adhesion of monocytes to endothelium.
Characterisation of the furanocoumarin phellopterin as a rat brain benzodiazepine receptor partial agonist in vitro.[Pubmed:8971802]
Neurosci Lett. 1996 Nov 29;219(3):151-4.
Phellopterin, a naturally occurring furanocoumarin found in the roots of Angelica dahurica, inhibits [3H]diazepam and ethyl 8-fluoro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4] benzodiazepine-3-carboxylate ([3H]Ro 15-1788) binding to the benzodiazepine site of the rat brain gamma-aminobutyric acidA (GABAA) receptor in vitro with IC50 values of 400 and 680 nM, respectively. Two other naturally occurring furanocoumarins, byakangelicol and imperatorin were significantly less potent, with IC50 values for inhibition of [3H]diazepam binding of 8.0 and 12.3 microM, respectively. Scatchard plot analysis showed that the inhibitory activity of Phellopterin was due to competitive inhibition of the benzodiazepine ligand binding. The results of GABA- and t-butylbicyclophosphorothionate (TBPS)-shift assays suggest that Phellopterin is a partial agonist of the central benzodiazepine receptors in vitro.
Biotransformation products of phellopterin by rat liver microsomes and the inhibition on NO production in LPS-activated RAW264.7 cells.[Pubmed:23046467]
J Asian Nat Prod Res. 2012;14(10):956-65.
Four new coumarins (2',3'-dihydroxyPhellopterin, E-5-methoxytrichoclin acetate, Z-5-methoxytrichoclin acetate, and E-5-methoxytrichoclin) and three known coumarins (byakangelicol, byakangelicin, and Z-5-methoxytrichoclin) were produced by liver microsomes from rats pre-treated with sodium phenobarbital. The chemical structures were elucidated on the basis of their spectroscopic data. The inhibitory activities of nitric oxide (NO) production in lipopolysaccharide-activated macrophage-like cell line RAW264.7 were tested. The main biotransformation product, byakangelicin, showed inhibitory activities of NO production with the IC(5)(0) value of 217.83 muM, whereas the parent compound Phellopterin showed cytotoxic effect on RAW264.7 cell at the concentration from 40 to 400 muM.
