LicopyranocoumarinCAS# 117038-80-9 |
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3D structure
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| Cas No. | 117038-80-9 | SDF | Download SDF |
| PubChem ID | 122851 | Appearance | Powder |
| Formula | C21H20O7 | M.Wt | 384.38 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 7-(2,4-dihydroxyphenyl)-2-(hydroxymethyl)-5-methoxy-2-methyl-3,4-dihydropyrano[3,2-g]chromen-8-one | ||
| SMILES | CC1(CCC2=C(O1)C=C3C(=C2OC)C=C(C(=O)O3)C4=C(C=C(C=C4)O)O)CO | ||
| Standard InChIKey | MOBCUWLJOZHPQL-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C21H20O7/c1-21(10-22)6-5-13-18(28-21)9-17-15(19(13)26-2)8-14(20(25)27-17)12-4-3-11(23)7-16(12)24/h3-4,7-9,22-24H,5-6,10H2,1-2H3 | ||
| 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. Licopyranocoumarin could as a potent neuroprotective drug via markedly blocked MPP+-induced neuronal PC12D cell death and disappearance of mitochondrial membrane potential, which were mediated by JNK. |
| Targets | P450 (e.g. CYP17) | JNK | ROS |
Licopyranocoumarin Dilution Calculator
Licopyranocoumarin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.6016 mL | 13.008 mL | 26.0159 mL | 52.0318 mL | 65.0398 mL |
| 5 mM | 0.5203 mL | 2.6016 mL | 5.2032 mL | 10.4064 mL | 13.008 mL |
| 10 mM | 0.2602 mL | 1.3008 mL | 2.6016 mL | 5.2032 mL | 6.504 mL |
| 50 mM | 0.052 mL | 0.2602 mL | 0.5203 mL | 1.0406 mL | 1.3008 mL |
| 100 mM | 0.026 mL | 0.1301 mL | 0.2602 mL | 0.5203 mL | 0.6504 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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The prenylated phenolic natural product isoglycycoumarin is a highly selective probe for human cytochrome P450 2A6.[Pubmed:28867491]
Eur J Pharm Sci. 2017 Nov 15;109:472-479.
Prenylated phenolic compounds are an important class of bioactive natural products. One major in vivo metabolic pathway of these compounds is hydroxylation at terminal methyl of the isoprenyl group. This study aims to identify the P450 isozyme catalyzing this metabolic reaction. In human liver microsomes, 16 out of 24 screened compounds could be metabolized into their hydroxylated derivatives. Chemical inhibition assays using 11 isozyme specific inhibitors indicated the hydroxylation reactions of 12 compounds were primarily catalyzed by cytochrome P450 2A6 (CYP2A6). In particular, CYP2A6 was the major enzyme participating in the metabolism of isoglycycoumarin (IGCM). The product of IGCM was obtained and identified as Licopyranocoumarin (4''-hydroxyl isoglycycoumarin) using NMR spectroscopic analysis. The Km values for human liver microsomes and recombinant human CYP2A6 were 7.98 and 10.14muM, respectively. According to molecular docking analysis, the catalytic mechanism may involve cyclized isoprenyl group of IGCM entering the active cavity of CYP2A6. These results demonstrate that IGCM could serve as an ideal isozyme selective probe to evaluate CYP2A6 activities.
Blockade of the dioxin pathway by herbal medicine Formula Bupleuri Minor: identification of active entities for suppression of AhR activation.[Pubmed:18451504]
Biol Pharm Bull. 2008 May;31(5):838-46.
Environmental pollutants including dioxins activate the aryl hydrocarbon receptor (AhR) and cause a wide range of pathologies. Development of AhR antagonists will be useful for prevention and treatment of the diseases related to AhR activation. Towards this goal, we aimed at seeking for potential AhR antagonists in herbal medicines using the dioxin responsive element-based sensing via secreted alkaline phosphatase (DRESSA). Through initial rough screening, 4 formulae were selected from 20 herbal medicines and subjected to the second, detailed screening. We found that only Formula bupleuri minor (TJ-9) significantly inhibited activation of AhR by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Among 7 raw herb extracts in TJ-9, Glycyrrhizae Radix and Scutellariae Radix were responsible for the antagonistic effect of TJ-9 against dioxin. Some constituents including Bupleuri Radix and Zingiberis Rhizoma rather activated AhR. Among 12 major constituents of Glycyrrhizae Radix and Scutellariae Radix, we identified that Licopyranocoumarin, glycyrrhizic acid and genistein in Glycyrrhizae Radix and baicalein, wogonin and daidzein in Scutellariae Radix had substantial antagonistic effects on AhR. Among these, baicalein most effectively blocked activation of AhR triggered by cigarette smoke, a strong activator of AhR. The antagonistic substances identified here may be useful for prevention from diseases associated with aberrant activation of AhR.
Identification of licopyranocoumarin and glycyrurol from herbal medicines as neuroprotective compounds for Parkinson's disease.[Pubmed:24960051]
PLoS One. 2014 Jun 24;9(6):e100395.
In the course of screening for the anti-Parkinsonian drugs from a library of traditional herbal medicines, we found that the extracts of choi-joki-to and daio-kanzo-to protected cells from MPP+-induced cell death. Because choi-joki-to and daio-kanzo-to commonly contain the genus Glycyrrhiza, we isolated Licopyranocoumarin (LPC) and glycyrurol (GCR) as potent neuroprotective principals from Glycyrrhiza. LPC and GCR markedly blocked MPP+-induced neuronal PC12D cell death and disappearance of mitochondrial membrane potential, which were mediated by JNK. LPC and GCR inhibited MPP+-induced JNK activation through the suppression of reactive oxygen species (ROS) generation, thereby inhibiting MPP+-induced neuronal PC12D cell death. These results indicated that LPC and GCR derived from choi-joki-to and daio-kanzo-to would be promising drug leads for PD treatment in the future.
