KurarinoneCAS# 34981-26-5 |
Quality Control & MSDS
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| Cas No. | 34981-26-5 | SDF | Download SDF |
| PubChem ID | 11982640 | Appearance | Powder |
| Formula | C26H30O6 | M.Wt | 438.5 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-5-methoxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one | ||
| SMILES | CC(=CCC(CC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=C(C=C(C=C3)O)O)C(=C)C)C | ||
| Standard InChIKey | LTTQKYMNTNISSZ-MWTRTKDXSA-N | ||
| Standard InChI | InChI=1S/C26H30O6/c1-14(2)6-7-16(15(3)4)10-19-21(29)12-24(31-5)25-22(30)13-23(32-26(19)25)18-9-8-17(27)11-20(18)28/h6,8-9,11-12,16,23,27-29H,3,7,10,13H2,1-2,4-5H3/t16-,23+/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 | Kurarinone exhibits anti-tumor, estrogenic, and anti-inflammatory activities, it also shows strong inhibitory effect on immune responses. Kurarinone may ameliorate chronic inflammatory skin diseases through the suppression of pathogenic CD4(+) T-cell differentiation and the overall immune response. Kurarinone sensitizes TNF-related apoptosis inducing ligand (TRAIL)-induced tumor cell apoptosis via suppression of NF-κB-dependent cFLIP expression; it may be by way of down-regulating Smad3 expression to interfere its induction on intercellular signal transduction and consequently ameliorate renal interstitial fibrosis. |
| Targets | JAK | STAT | NF-kB | Bcl-2/Bax | IkB | IKK | TNF-α | CD4(+) |
| In vitro | Estrogenic and anticarcinogenic properties of kurarinone, a lavandulyl flavanone from the roots of Sophora flavescens.[Pubmed: 15568770 ]J. Nat.Prod., 2004, 67(11):1829-32.Kurarinone, a lavandulyl flavanone, was isolated from a polyphenolic extract of the roots of Sophora flavescens using fractionation guided by estrogenic activity, which was determined by recombinant yeast and Ishikawa Var-I bioassays. |
| In vivo | Kurarinone regulates immune responses through regulation of the JAK/STAT and TCR-mediated signaling pathways.[Pubmed: 23333426 ]Biochem. Pharmacol., 2013, 85(8):1134-44.Sophora flavescens is a medicinal herb that contains flavonoids and quinolizidine alkaloids and has a wide range of biological activities due to its anti-inflammatory, anti-bacterial and anti-cancer properties. We isolated a series of flavonoids from the roots of Sophora flavescens and examined their ability to inhibit immune responses. |
| Kinase Assay | Kurarinone promotes TRAIL-induced apoptosis by inhibiting NF-κB-dependent cFLIP expression in HeLa cells.[Pubmed: 22932446 ]Exp. Mol. Med., 2012, 44(11): 653-64.This study was designed to investigate the effects of the prenylated flavonoid Kurarinone on TNF-related apoptosis inducing ligand (TRAIL)-induced apoptosis and its underlying mechanism. |
Kurarinone Dilution Calculator
Kurarinone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2805 mL | 11.4025 mL | 22.805 mL | 45.61 mL | 57.0125 mL |
| 5 mM | 0.4561 mL | 2.2805 mL | 4.561 mL | 9.122 mL | 11.4025 mL |
| 10 mM | 0.2281 mL | 1.1403 mL | 2.2805 mL | 4.561 mL | 5.7013 mL |
| 50 mM | 0.0456 mL | 0.2281 mL | 0.4561 mL | 0.9122 mL | 1.1403 mL |
| 100 mM | 0.0228 mL | 0.114 mL | 0.2281 mL | 0.4561 mL | 0.5701 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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Kurarinone promotes TRAIL-induced apoptosis by inhibiting NF-kappaB-dependent cFLIP expression in HeLa cells.[Pubmed:22932446]
Exp Mol Med. 2012 Nov 30;44(11):653-64.
This study was designed to investigate the effects of the prenylated flavonoid Kurarinone on TNF-related apoptosis inducing ligand (TRAIL)-induced apoptosis and its underlying mechanism. A low dose of Kurarinone had no significant effect on apoptosis, but this compound markedly promoted tumor cell death through elevation of Bid cleavage, cytochrome c release release and caspase activation in HeLa cells treated with TRAIL. Caspase inhibitors inhibited Kurarinone-mediated cell death, which indicates that the cytotoxic effect of this compound is mediated by caspase-dependent apoptosis. The cytotoxic effect of Kurarinone was not associated with expression levels of Bcl-2 and IAP family proteins, such as Bcl-2, Bcl-xL, Bid, Bad, Bax, XIAP, cIAP-1 and cIAP-2. In addition, this compound did not regulate the death-inducing receptors DR4 and DR5. On the other hand, Kurarinone significantly inhibited TRAIL-induced IKK activation, IkappaB degradation and nuclear translocation of NF-kappaB, as well as effectively suppressed cellular FLICE-inhibitory protein long form (cFLIPL) expression. The synergistic effects of Kurarinone on TRAIL-induced apoptosis were mimicked when Kurarinone was replaced by the NF-kappaB inhibitor withaferin A or following siRNA-mediated knockdown of cFLIPL. Moreover, cFLIP overexpression effectively antagonized Kurarinone-mediated TRAIL sensitization. These data suggest that Kurarinone sensitizes TRAIL-induced tumor cell apoptosis via suppression of NF-kappaB-dependent cFLIP expression, indicating that this compound can be used as an anti-tumor agent in combination with TRAIL.
Estrogenic and anticarcinogenic properties of kurarinone, a lavandulyl flavanone from the roots of Sophora flavescens.[Pubmed:15568770]
J Nat Prod. 2004 Nov;67(11):1829-32.
Kurarinone, a lavandulyl flavanone, was isolated from a polyphenolic extract of the roots of Sophora flavescens using fractionation guided by estrogenic activity, which was determined by recombinant yeast and Ishikawa Var-I bioassays. Kurarinone showed weak estrogenic activity both in the yeast screen and in the Ishikawa Var-I assay with EC(50) values of 4.6 and 1.66 microM, respectively. Furthermore, Kurarinone was found to have potent cytotoxic activity (IC(50) value = 22.2 microM) against human MCF-7/6 breast cancer cells in the sulforhodamine-B assay.
Kurarinone regulates immune responses through regulation of the JAK/STAT and TCR-mediated signaling pathways.[Pubmed:23333426]
Biochem Pharmacol. 2013 Apr 15;85(8):1134-44.
Sophora flavescens is a medicinal herb that contains flavonoids and quinolizidine alkaloids and has a wide range of biological activities due to its anti-inflammatory, anti-bacterial and anti-cancer properties. We isolated a series of flavonoids from the roots of Sophora flavescens and examined their ability to inhibit immune responses. Among the flavonoids, Kurarinone exhibited the strongest inhibitory effect on immune responses. Kurarinone suppressed the differentiation of CD4(+) T cells by inhibiting the expression and production of T-cell lineage-specific master regulators and cytokines. Our results also demonstrated that Kurarinone directly suppressed the cytokine-induced Janus kinase/signal transducer and activator of transcription (JAK/STAT) signaling and T-cell receptor (TCR) pathways. In two established animal models of chronic inflammatory skin disease, one in which psoriasis-like skin disease was induced by an interleukin 23 (IL-23) injection into mouse ears and another in which 2,4,6-trinitrochlorobenzene (TNCB) application on the abdomens of mice was used to induce contact dermatitis, Kurarinone repressed disease development by inhibiting the expression of pro-inflammatory mediators, including cytokines, chemokines and enzyme in murine ear skin. This study provides new evidence that Kurarinone may ameliorate chronic inflammatory skin diseases through the suppression of pathogenic CD4(+) T-cell differentiation and the overall immune response.
