IsosilybinCAS# 72581-71-6 |
- Isosilybin B
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- Isosilybin A
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 72581-71-6 | SDF | Download SDF |
| PubChem ID | 3085830 | Appearance | White-light yellow powder |
| Formula | C25H22O10 | M.Wt | 482.44 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | Isosilybinin | ||
| Solubility | DMSO : ≥ 28 mg/mL (58.04 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one | ||
| SMILES | COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O | ||
| Standard InChIKey | FDQAOULAVFHKBX-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-18-7-12(3-5-16(18)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3 | ||
| 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 | Isosilybin and Silybin might be suitable candidates to design potent PXR antagonists to prevent drug-drug interactions via CYP3A4 in cancer patients. |
| Targets | PPAR | P450 (e.g. CYP17) | PXR |
| In vitro | Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma.[Pubmed: 24597776]J Nat Prod. 2014 Apr 25;77(4):842-7.Peroxisome proliferator-activated receptor gamma (PPARγ) is a key regulator of glucose and lipid metabolism. Agonists of this nuclear receptor are used in the treatment of type 2 diabetes and are also studied as a potential treatment of other metabolic diseases, including nonalcoholic fatty liver disease. Silymarin, a concentrated phenolic mixture from milk thistle (Silybum marianum) seeds, is used widely as a supportive agent in the treatment of a variety of liver diseases.
|
| Kinase Assay | Milk thistle's active components silybin and isosilybin: novel inhibitors of PXR-mediated CYP3A4 induction.[Pubmed: 23674609]Drug Metab Dispos. 2013 Aug;41(8):1494-504.
Because cancer is often treated with combination therapy, unexpected pharmacological effects can occur because of drug-drug interactions. Several drugs are able to cause upregulation or downregulation of drug transporters or cytochrome P450 enzymes, particularly CYP3A4. Induction of CYP3A4 may result in decreased plasma levels and therapeutic efficacy of anticancer drugs. Since the pregnane X receptor (PXR) is one of the major transcriptional regulators of CYP3A4, PXR antagonists can possibly prevent CYP3A4 induction. Currently, a limited number of PXR antagonists are available. Some of these antagonists, such as sulphoraphane and coumestrol, belong to the so-called complementary and alternative medicines (CAM).
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Isosilybin Dilution Calculator
Isosilybin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.0728 mL | 10.364 mL | 20.728 mL | 41.4559 mL | 51.8199 mL |
| 5 mM | 0.4146 mL | 2.0728 mL | 4.1456 mL | 8.2912 mL | 10.364 mL |
| 10 mM | 0.2073 mL | 1.0364 mL | 2.0728 mL | 4.1456 mL | 5.182 mL |
| 50 mM | 0.0415 mL | 0.2073 mL | 0.4146 mL | 0.8291 mL | 1.0364 mL |
| 100 mM | 0.0207 mL | 0.1036 mL | 0.2073 mL | 0.4146 mL | 0.5182 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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Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma.[Pubmed:24597776]
J Nat Prod. 2014 Apr 25;77(4):842-7.
Peroxisome proliferator-activated receptor gamma (PPARgamma) is a key regulator of glucose and lipid metabolism. Agonists of this nuclear receptor are used in the treatment of type 2 diabetes and are also studied as a potential treatment of other metabolic diseases, including nonalcoholic fatty liver disease. Silymarin, a concentrated phenolic mixture from milk thistle (Silybum marianum) seeds, is used widely as a supportive agent in the treatment of a variety of liver diseases. In this study, the PPARgamma activation potential of silymarin and its main constituents was investigated. Isosilybin A (3) caused transactivation of a PPARgamma-dependent luciferase reporter in a concentration-dependent manner. This effect could be reversed upon co-treatment with the PPARgamma antagonist T0070907. In silico docking studies suggested a binding mode for 3 distinct from that of the inactive silymarin constituents, with one additional hydrogen bond to Ser342 in the entrance region of the ligand-binding domain of the receptor. Hence, Isosilybin A (3) has been identified as the first flavonolignan PPARgamma agonist, suggesting its further investigation as a modulator of this nuclear receptor.
Milk thistle's active components silybin and isosilybin: novel inhibitors of PXR-mediated CYP3A4 induction.[Pubmed:23674609]
Drug Metab Dispos. 2013 Aug;41(8):1494-504.
Because cancer is often treated with combination therapy, unexpected pharmacological effects can occur because of drug-drug interactions. Several drugs are able to cause upregulation or downregulation of drug transporters or cytochrome P450 enzymes, particularly CYP3A4. Induction of CYP3A4 may result in decreased plasma levels and therapeutic efficacy of anticancer drugs. Since the pregnane X receptor (PXR) is one of the major transcriptional regulators of CYP3A4, PXR antagonists can possibly prevent CYP3A4 induction. Currently, a limited number of PXR antagonists are available. Some of these antagonists, such as sulphoraphane and coumestrol, belong to the so-called complementary and alternative medicines (CAM). Therefore, the aim was to determine the potential of selected CAM (beta-carotene, Echinacea purpurea, garlic, Ginkgo biloba, ginseng, grape seed, green tea, milk thistle, saw palmetto, valerian, St. John's Wort, and vitamins B6, B12, and C) to inhibit PXR-mediated CYP3A4 induction at the transcriptional level, using a reporter gene assay and a real-time polymerase chain reaction assay in LS180 colon adenocarcinoma cells. Furthermore, computational molecular docking and a LanthaScreen time-resolved fluorescence resonance energy transfer (TR-FRET) PXR competitive binding assay were performed to explore whether the inhibiting CAM components interact with PXR. The results demonstrated that milk thistle is a strong inhibitor of PXR-mediated CYP3A4 induction. The components of milk thistle responsible for this effect were identified as silybin and Isosilybin. Furthermore, computational molecular docking revealed a strong interaction between both silybin and Isosilybin and PXR, which was confirmed in the TR-FRET PXR assay. In conclusion, silybin and Isosilybin might be suitable candidates to design potent PXR antagonists to prevent drug-drug interactions via CYP3A4 in cancer patients.
