| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Mushroom tyrosinase (IC50 = 0.1 μM)
|
|---|---|
| ln Vitro |
Kurarinol's cytotoxic action is rather low (EC50>30 μM)[1]. Kurarinol prevents S. from producing melanin. bikiniensis without interfering with microbial growth[1]. Kurarinol inhibits cellular signal transducer and activator of transcription 3 signaling (STAT3), which causes hepatocellular carcinoma cells to undergo apoptosis[2].
|
| ln Vivo |
Kurarinol (20 mg/kg; po; daily; for 3 days) lowers serum lipid levels in rats that have been made hyperlipidemic by a high-cholesterol diet[3]
In this study, we investigated the hypolipidemic effects of Sophora flavescens in poloxamer 407-induced hyperlipidemic and cholesterol-fed rats. The MeOH extract and 4 fractions of S. flavescens were administered at doses of 250 and 100 mg/kg body weight, respectively, once a day for 3 d to the poloxamer 407-induced hyperlipidemic rats. Serum lipid levels such as total cholesterol (TC), triglycerides (TG), and low-density lipoprotein-cholesterol (LDL-C) were markedly elevated in the poloxamer 407-induced hyperlipidemic control rats, while lipid levels were significantly decreased in the rats administered the MeOH extract or 4 fractions of S. flavescens. In addition, serum high-density lipoprotein-cholesterol (HDL-C) was reduced in the poloxamer 407-induced hyperlipidemic control rats. However, oral administration of both the MeOH extract and 4 fractions significantly increased HDL-C levels. Of the tested fractions, the EtOAc fraction showed the strongest lipid-lowering effect, as well as a high antiatherogenic potential with atherogenic index (A.I.) values of less than 1.92. We also investigated the hypolipidemic effects of the main compounds of the EtOAc fraction, kurarinol and kuraridinol, using the hyperlipidemic and hypercholesterolemic animal models. Here, elevated TC, TG, and LDL-C levels in the poloxamer 407-induced hyperlipidemic and cholesterol-fed rats were significantly reduced after oral administration of the compounds, and HDL-C levels had a significant increase. Furthermore, A.I. values were lowered by administering kurarinol and kuraridinol. In particular, kuraridinol exhibited stronger protective activities against hyperlipidemia than kurarinol. These results suggest that S. flavescens and its constituents may be effective cholesterol-lowering agents and useful for preventing hypercholesterolemic atherosclerosis[3]. |
| Enzyme Assay |
It is well known that flavanones, sophoraflavanone G 1, kurarinone 2, and kurarinol 3, from the root of Sophora flavescens, have extremely strong tyrosinase inhibitory activity. This study delineates the principal pharmacological features of kurarinol 3 that lead to inhibition of the oxidation of l-tyrosine to melanin by mushroom tyrosinase (IC(50) of 100 nM). The inhibition kinetics analyses unveil that compounds 1 and 2 are noncompetitive inhibitors. However similar analysis shows kurarinol 3 to be a competitive inhibitor. Compounds 1 and 2 exhibited potent antibacterial activity with 10 microg/disk against Gram-positive bacteria, whereas kurarinol 3 did not ostend any antibacterial activity. Interestingly, kurarinol 3 inhibits production of melanin in S. bikiniensis without affecting the growth of microorganism. It is thus distinctly different from the other tyrosinase inhibitors 1 and 2. In addition, kurarinol 3 manifests relatively low cytotoxic activity (EC(50)>30 microM) compared to 1 and 2. To account for these observations, we conducted molecular modeling studies. These suggested that the lavandulyl group within 3 is instrumental in the interaction with the enzyme. More specifically, the terminal hydroxy function within the lavandulyl group is most important for optimal binding [1].
|
| Cell Assay |
Kurarinol is a flavonoid isolated from roots of the medical plant Sophora flavescens. However, its cytotoxic activity against hepatocellular carcinoma (HCC) cells and toxic effects on mammalians remain largely unexplored. Here, the pro-apoptotic activities of kurarinol on HCC cells and its toxic impacts on tumor-bearing mice were evaluated. The molecular mechanisms underlying kurarinol-induced HCC cell apoptosis were also investigated. We found that kurarinol dose-dependently provoked HepG2, Huh-7 and H22 HCC cell apoptosis. In addition, kurarinol gave rise to a considerable decrease in the transcriptional activity of signal transducer and activator of transcription 3 (STAT3) in HCC cells. Suppression of STAT3 signaling is involved in kurarinol-induced HCC cell apoptosis. In vivo studies showed that kurarinol injection substantially induced transplanted H22 cell apoptosis with low toxic impacts on tumor-bearing mice. Similarly, the transcriptional activity of STAT3 in transplanted tumor tissues was significantly suppressed after kurarinol treatment. Collectively, our current research demonstrated that kurarinol has the capacity of inducing HCC cell apoptosis both in vitro and in vivo with undetectable toxic impacts on the host. Suppressing STAT3 signaling is implicated in kurarinol-mediated HCC cell apoptosis[2].
|
| Animal Protocol |
Animal/Disease Models: Male SD (Sprague-Dawley) rats (120-130g), hypercholesterolemic models[3]
Doses: 20 mg/kg Route of Administration: Oral administration, daily, for 3 days Experimental Results: diminished serum TC, TG, and LDL-C levels. |
| References |
|
| Additional Infomation |
Kurarinol is a trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4' , a methoxy group at position 5 and a (2S)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl group at position 8 respectively. It has a role as an anti-inflammatory agent, an antioxidant and a plant metabolite. It is a trihydroxyflavanone, a monomethoxyflavanone and a member of 4'-hydroxyflavanones. It is functionally related to a (2S)-flavanone.
Kurarinol has been reported in Albizia julibrissin and Sophora flavescens with data available. |
| Molecular Formula |
C26H32O7
|
|---|---|
| Molecular Weight |
456.53
|
| Exact Mass |
456.215
|
| CAS # |
855746-98-4
|
| PubChem CID |
44563198
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
4.804
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
8
|
| Heavy Atom Count |
33
|
| Complexity |
692
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
C(C1C(O)=CC(OC)=C2C(C[C@@H](C3C=CC(O)=CC=3O)OC=12)=O)[C@H](C(=C)C)CCC(O)(C)C
|
| InChi Key |
XMUPAAIHKAIUSU-QRQCRPRQSA-N
|
| InChi Code |
InChI=1S/C26H32O7/c1-14(2)15(8-9-26(3,4)31)10-18-20(29)12-23(32-5)24-21(30)13-22(33-25(18)24)17-7-6-16(27)11-19(17)28/h6-7,11-12,15,22,27-29,31H,1,8-10,13H2,2-5H3/t15-,22+/m1/s1
|
| Chemical Name |
(2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-[(2R)-5-hydroxy-5-methyl-2-prop-1-en-2-ylhexyl]-5-methoxy-2,3-dihydrochromen-4-one
|
| Synonyms |
Kurarinol; 855746-98-4; CHEBI:81093; (2S)-2-(2,4-Dihydroxyphenyl)-7-hydroxy-8-[(2R)-5-hydroxy-5-methyl-2-prop-1-en-2-ylhexyl]-5-methoxy-2,3-dihydrochromen-4-one; (2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-[(2R)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl]-5-methoxy-2,3-dihydro-4H-1-benzopyran-4-one; 4'',5''-Dihydro-5''-hydroxysophoraflavanone G 5-methyl ether; (2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-((2R)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl)-5-methoxy-2,3-dihydro-4H-1-benzopyran-4-one; (2S)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-((2R)-5-hydroxy-5-methyl-2-prop-1-en-2-ylhexyl)-5-methoxy-2,3-dihydrochromen-4-one;
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
|
|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1904 mL | 10.9522 mL | 21.9044 mL | |
| 5 mM | 0.4381 mL | 2.1904 mL | 4.3809 mL | |
| 10 mM | 0.2190 mL | 1.0952 mL | 2.1904 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
