Kurarinol

CAS# 855746-98-4

Kurarinol

Catalog No. BCN3447----Order now to get a substantial discount!

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Quality Control of Kurarinol

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Chemical structure

Kurarinol

3D structure

Chemical Properties of Kurarinol

Cas No. 855746-98-4 SDF Download SDF
PubChem ID 44563198 Appearance Powder
Formula C26H32O7 M.Wt 456.5
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-8-[(2R)-5-hydroxy-5-methyl-2-prop-1-en-2-ylhexyl]-5-methoxy-2,3-dihydrochromen-4-one
SMILES CC(=C)C(CCC(C)(C)O)CC1=C(C=C(C2=C1OC(CC2=O)C3=C(C=C(C=C3)O)O)OC)O
Standard InChIKey XMUPAAIHKAIUSU-QRQCRPRQSA-N
Standard InChI 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
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.
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.
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.

Source of Kurarinol

The root of Sophora flavescens

Biological Activity of Kurarinol

Description1. Kurarinol is a potent inhibitor of sortase A, with an IC50 value of 107.7 ± 6.6 μM. 2. Kurarinol has extremely strong tyrosinase inhibitory activity, exerts varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, is a candidate as skin-whitening agents.
TargetsSTAT | HBV | Tyrosinase

Kurarinol Dilution Calculator

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Kurarinol Molarity Calculator

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Preparing Stock Solutions of Kurarinol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.1906 mL 10.9529 mL 21.9058 mL 43.8116 mL 54.7645 mL
5 mM 0.4381 mL 2.1906 mL 4.3812 mL 8.7623 mL 10.9529 mL
10 mM 0.2191 mL 1.0953 mL 2.1906 mL 4.3812 mL 5.4765 mL
50 mM 0.0438 mL 0.2191 mL 0.4381 mL 0.8762 mL 1.0953 mL
100 mM 0.0219 mL 0.1095 mL 0.2191 mL 0.4381 mL 0.5476 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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References on Kurarinol

[Effect of kurarinol on peripheral blood CTL surface PD-1 expression of patients with chronic hepatitis B].[Pubmed:23627026]

Zhonghua Shi Yan He Lin Chuang Bing Du Xue Za Zhi. 2012 Dec;26(6):446-9.

OBJECTIVE: To explore the anti-viral mechanism of Kurarinol through studying its influence on cytotoxic T lymphocyte (CTL) surface program death receptor-1 (PD-1) expression of patients with chronic hepatitis B (CHB). METHODS: 69 cases of CHB, HBV DNA > or = 10(4) copies/ml, HBeAg positive, human leukocyte antigen (HLA)-A2 positive, alanine aminotransferase (ALT) > 2 x upper limit of normal value(ULN).69 cases were randomly divided into two groups:34 cases in treatment group,600 mg of Kurarinol glucose injection was used for intravenous dripping, once a day, one month later, 200 mg of Kurarinol capsule was used orally,three times a day and 200 mg of silybin meglumine tablet was used orally, three times a day. 35 cases in control group, only silibin meglumine tablet was used, method and dosage were the same as those of treatment group. Three months later, their peripheral blood HBV specific CTL surface PD-1 expression, non-specific CTL surface PD-1 expression and level of HBV specific CTL,HBV DNA and HBeAg negative rate and liver functions were analyzed and compared. RESULTS: 3 months after treatment, peripheral blood HBV specific CTL surface PD-1 expression of the treatment group decreased compared with that before treatment (t = 2.39, P < 0.05), it also decreased compared with that of the control group 3 months after treatment (t = 2.26, P < 0.05), HBV specific CTL increased compared with that before treatment( t = 3.01, P < 0.01), it also increased compared with that of the control group after treatment (t = 2.65, P < 0.05). There was no significant difference of non-specific CTL surface PD-1 expression compared with that before treatment (P > 0.05), and there was no significant difference compared with that of the control group after treatment (P > 0.05). HBV DNA of 11 cases (32.5%) turned negative ( HBV DNA < 500 copies/ ml), higher than that of the control group after treatment (2 cases, 5.71%) chi2 = 7.99, P < 0.01, HBeAg of 9 cases (26.47%) turned negative, higher than that of the control group after treatment (1 case, 2.86%), chi2 = 7.75, P < 0.01. CONCLUSION: Kurarinol can increase level of HBV specific CTL by down-regulating peripheral blood HBV specific CTL surface PD-1 expression of CHB patients, which may be one of the possible mechanisms that Kurarinol can remove or inhibit HBV of CHB patients.

Inhibitory effects of kurarinol, kuraridinol, and trifolirhizin from Sophora flavescens on tyrosinase and melanin synthesis.[Pubmed:18175961]

Biol Pharm Bull. 2008 Jan;31(1):154-8.

Previously, it was reported that some prenylated flavonoids contained in the dichloromethane fraction of the ethanolic extract of Sophora flavescens, such as kuraridin, sophoraflavanone G, kurarinone, and kushenol F, are tyrosinase inhibitors; however, based on the level of these inhibitors in the extract, its inhibitory effect on tyrosinase activity was higher than expected. This has led us to further investigate other possible constituents that may contribute to the extract's strong inhibitory activity. The results of this study indicate that Kurarinol (1), kuraridinol (2), and trifolirhizin (3), from the ethyl acetate fraction of Sophora extract, can inhibit tyrosinase activity. Compared with kojic acid (16.22+/-1.71 microM), compounds 1-3 possessed potent tyrosinase inhibitory activity with IC(50) values of 8.60+/-0.51, 0.88+/-0.06, and 506.77+/-4.94 microM, respectively. These three compounds were further tested for their inhibitory effects on melanogenesis. In cultured B16 melanoma cells, 1-3 markedly inhibited (>50%) melanin synthesis at 50 microM. This is the first study indicating that 1-3 exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, and therefore, are candidates as skin-whitening agents.

Kurarinol, tyrosinase inhibitor isolated from the root of Sophora flavescens.[Pubmed:17951038]

Phytomedicine. 2008 Aug;15(8):612-8.

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.

[Study on effects of kurarinol combined with glycyrrhizic acid on cellular immunity of patients with chronic hepatitis B].[Pubmed:23002547]

Zhonghua Shi Yan He Lin Chuang Bing Du Xue Za Zhi. 2012 Apr;26(2):108-10.

OBJECTIVE: To explore effects of Kurarinol combined with Diammonium Glycyrrhizinate on specific cellular immunity of patients with chronic hepatitis B (CHB). METHODS: Sixty-three CHB patients were randomly divided into two groups, 32 cases in group of Kurarinol combined with Diammonium Glycyrrhizinate group (combined therapy group) were treated with 600 mg Kurarinol glucose injection intravenously, once a day for one month, then 200 mg Kurarinol capsule was used orally, three times a day for two months. 150 mg Diammonium Glycyrrhizinate for Injection was added to 250 ml 10% glucose injection for intravenous drip, once a day for one month, then 150 mg Diammonium Glycyrrhizinate capsule was used orally, three times a day for two months; 31 case in Kurarinol group (single drug group) only used Kurarinol, methods and dosage were the same as those of treatment group. HBV specific CTL, T cell subgroups, change of Th1 and Th2 level, HBV-DNA and HBeAg negative rate of the two groups were compared. RESULTS: Three months after treatment, HBV specific CTL, CD4 + and Th1 of combined therapy group were higher than those before treatment, and higher than those of single drug group after treatment (P < 0.01). CONCLUSION: HBV-DNA and HBeAg negative rate between the two groups had no statistic significance (P > 0.05). CONCLUSION: Kurarinol combined with Diammonium Glycyrrhizinate can further increase HBV specific CTL, CD4+ and Th1 level of CHB patients.

Kurarinol induces hepatocellular carcinoma cell apoptosis through suppressing cellular signal transducer and activator of transcription 3 signaling.[Pubmed:24997323]

Toxicol Appl Pharmacol. 2014 Dec 1;281(2):157-65.

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.

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