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Chrysophanol 8-O-glucoside

CAS# 13241-28-6

Chrysophanol 8-O-glucoside

Catalog No. BCN6175----Order now to get a substantial discount!

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Quality Control of Chrysophanol 8-O-glucoside

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Chemical structure

Chrysophanol 8-O-glucoside

3D structure

Chemical Properties of Chrysophanol 8-O-glucoside

Cas No. 13241-28-6 SDF Download SDF
PubChem ID 442731 Appearance Orange powder
Formula C21H20O9 M.Wt 416.4
Type of Compound Anthraquinones Storage Desiccate at -20°C
Synonyms Pulmatin
Solubility Soluble in DMSO and methan
Chemical Name 1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
SMILES CC1=CC(=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)OC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey WMMOMSNMMDMSRB-JNHRPPPUSA-N
Standard InChI InChI=1S/C21H20O9/c1-8-5-10-14(11(23)6-8)18(26)15-9(16(10)24)3-2-4-12(15)29-21-20(28)19(27)17(25)13(7-22)30-21/h2-6,13,17,19-23,25,27-28H,7H2,1H3/t13-,17-,19+,20-,21-/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 Chrysophanol 8-O-glucoside

1 Cassia sp. 2 Rheum sp. 3 Rhodiola sp. 4 Rumex sp.

Biological Activity of Chrysophanol 8-O-glucoside

DescriptionChrysophanol-8-O-beta-D-glucopyranoside and chrysophanol have mild cytotoxicity and anti-diabetic properties and can play metabolic roles in the insulin-stimulated glucose transport pathway; it has potent inhibitory effect on collagen- and thrombin-induced platelet aggregation, it only inhibits platelet phosphatidylserine exposure.Chrysophanol-8-O-beta-D-glucopyranoside also exhibits significant anti-HBV activities with improved liver function, and enhanced HBeAg and HBsAg sero-conversion rates as well as HBV DNA clearance rates in HepG2 2.2.15 cells, DHBV models, or patients with chronic hepatitis B (CHB).
TargetsHBV | GLUT
In vitro

Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities.[Pubmed: 22302018]

J Pharmacol Sci. 2012;118(2):245-54.

Rhubarb is a widely used traditional medicine and has been reported to elicit a number of biological effects including anti-inflammatory and antiplatelet effects. In the present study, we investigated the effects of anthraquinone derivatives isolated from rhubarb on platelet activity.
METHODS AND RESULTS:
Of four anthraquinone derivatives isolated from rhubarb examined, Chrysophanol 8-O-glucoside (CP-8-O-glc) was found to have the most potent inhibitory effect on collagen- and thrombin-induced platelet aggregation. Chrysophanol 8-O-glucoside-treated mice showed significantly prolonged bleeding times. Furthermore, Chrysophanol 8-O-glucoside was found to have a significant inhibitory effect on rat platelet aggregation ex vivo and on thromboxane A(2) formation in vitro. In coagulation tests, Chrysophanol 8-O-glucoside did not alter prothrombin time, and it prolonged the activated partial thromboplastin time. However, Chrysophanol 8-O-glucoside only inhibited platelet phosphatidylserine exposure, but not exert direct inhibition on intrinsic factors.
CONCLUSIONS:
This study demonstrates the antiplatelet and anticoagulant effects of Chrysophanol 8-O-glucoside and suggests that this compound might be of therapeutic benefit for the prevention of platelet-related cardiovascular diseases.

Traditional Chinese medicine and related active compounds: a review of their role on hepatitis B virus infection.[Pubmed: 24423652]

Drug Discov Ther. 2013 Dec;7(6):212-24.

Over a long period of time in clinical practice and in basic research progress, the effectiveness and beneficial contribution of TCM on CHB have been gradually known and confirmed.
METHODS AND RESULTS:
Based upon our review of related papers and because of our prior knowledge and experience, we have selected some Chinese medicines, including Chinese herbal formulas (e.g., Xiao-Chai-Hu-Tang, Xiao-Yao-San, and Long-Dan-Xie-Gan-Tang), single herbs (e.g., Phyllanthus niruri, Radix astragali, Polygonum cuspidatum, Rheum palmatum, and Salvia miltiorrhiza) and related active compounds (e.g., wogonin, artesunate, saikosaponin, astragaloside IV, and chrysophanol 8-O-beta-Dglucoside(Chrysophanol 8-O-glucoside)) and Chinese medicine preparations (e.g., silymarin, silibinin, kushenin, and cinobufacini), which seem effective and worthy of additional and indepth study in treating CHB, and we have given them a brief review. We conclude that these Chinese herbal medicines exhibit significant anti-HBV activities with improved liver function, and enhanced HBeAg and HBsAg sero-conversion rates as well as HBV DNA clearance rates in HepG2 2.2.15 cells, DHBV models, or patients with CHB.
CONCLUSIONS:
We hope this review will contribute to an understanding of TCM and related active compounds as an effective treatment for CHB and provide useful information for the development of more effective antiviral drugs.

Protocol of Chrysophanol 8-O-glucoside

Kinase Assay

Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome.[Pubmed: 18981591]

Biol Pharm Bull. 2008 Nov;31(11):2154-7.

An ethanol extract of rhubarb rhizome exhibited marked glucose transport activity in differentiated L6 rat myotubes. Activity-guided fractionation resulted in the isolation of two anthraquinones, chrysophanol-8-O-beta-D-glucopyranoside (Chrysophanol 8-O-glucoside,1) and chrysophanol (2).
METHODS AND RESULTS:
The anti-diabetic effect was examined by glucose transport activity, glucose transporter 4 (Glut4) expression in myotubes, and the level of insulin receptor (IR) tyrosine phosphorylation as influenced by tyrosine phosphatase 1B, each of which is a major target of diabetes treatment. Chrysophanol-8-O-beta-D-glucopyranoside(Chrysophanol 8-O-glucoside) up to 25 microM dose-dependently activated glucose transport in insulin-stimulated myotubes. Increased tyrosine phosphorylation of IR due to tyrosine phosphatase 1B inhibitory activity with an IC50 value of 18.34+/-0.29 microM and unchanged Glut4 mRNA levels was observed following chrysophanol-8-O-beta-D-glucopyranoside(Chrysophanol 8-O-glucoside) treatment. Chrysophanol up to 100 microM exerted mild glucose transport activity and elevated the tyrosine phosphorylation of IR via tyrosine phosphatase 1B inhibition (IC50=79.86+/-0.12 microM); Glut4 mRNA expression was also significantly increased by 100 microM. The ED50 values of the two compounds were 59.38+/-0.66 and 79.69+/-0.03 microM, respectively.
CONCLUSIONS:
Therefore, these two anthraquinones from rhubarb rhizome, chrysophanol-8-O-beta-D-glucopyranoside(Chrysophanol 8-O-glucoside) and chrysophanol, have mild cytotoxicity and anti-diabetic properties and could play metabolic roles in the insulin-stimulated glucose transport pathway.

Chrysophanol 8-O-glucoside Dilution Calculator

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Preparing Stock Solutions of Chrysophanol 8-O-glucoside

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4015 mL 12.0077 mL 24.0154 mL 48.0307 mL 60.0384 mL
5 mM 0.4803 mL 2.4015 mL 4.8031 mL 9.6061 mL 12.0077 mL
10 mM 0.2402 mL 1.2008 mL 2.4015 mL 4.8031 mL 6.0038 mL
50 mM 0.048 mL 0.2402 mL 0.4803 mL 0.9606 mL 1.2008 mL
100 mM 0.024 mL 0.1201 mL 0.2402 mL 0.4803 mL 0.6004 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 Chrysophanol 8-O-glucoside

Traditional Chinese medicine and related active compounds: a review of their role on hepatitis B virus infection.[Pubmed:24423652]

Drug Discov Ther. 2013 Dec;7(6):212-24.

Since the significant public health hazard of Hepatitis B virus (HBV) infection and obvious drug resistance and dose-dependent side effects for common antiviral agents (e.g., interferon alpha, lamivudine, and adefovir), continuous development of agents to treat HBV infection is urgently needed. Traditional Chinese medicine (TCM) is an established segment of the health care system in China. Currently, it is widely used for chronic hepatitis B (CHB) in China and many parts of the world. Over a long period of time in clinical practice and in basic research progress, the effectiveness and beneficial contribution of TCM on CHB have been gradually known and confirmed. Based upon our review of related papers and because of our prior knowledge and experience, we have selected some Chinese medicines, including Chinese herbal formulas (e.g., Xiao-Chai-Hu-Tang, Xiao-Yao-San, and Long-Dan-Xie-Gan-Tang), single herbs (e.g., Phyllanthus niruri, Radix astragali, Polygonum cuspidatum, Rheum palmatum, and Salvia miltiorrhiza) and related active compounds (e.g., wogonin, artesunate, saikosaponin, astragaloside IV, and chrysophanol 8-O-beta-Dglucoside) and Chinese medicine preparations (e.g., silymarin, silibinin, kushenin, and cinobufacini), which seem effective and worthy of additional and indepth study in treating CHB, and we have given them a brief review. We conclude that these Chinese herbal medicines exhibit significant anti-HBV activities with improved liver function, and enhanced HBeAg and HBsAg sero-conversion rates as well as HBV DNA clearance rates in HepG2 2.2.15 cells, DHBV models, or patients with CHB. We hope this review will contribute to an understanding of TCM and related active compounds as an effective treatment for CHB and provide useful information for the development of more effective antiviral drugs.

Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome.[Pubmed:18981591]

Biol Pharm Bull. 2008 Nov;31(11):2154-7.

An ethanol extract of rhubarb rhizome exhibited marked glucose transport activity in differentiated L6 rat myotubes. Activity-guided fractionation resulted in the isolation of two anthraquinones, chrysophanol-8-O-beta-D-glucopyranoside (1) and chrysophanol (2). The anti-diabetic effect was examined by glucose transport activity, glucose transporter 4 (Glut4) expression in myotubes, and the level of insulin receptor (IR) tyrosine phosphorylation as influenced by tyrosine phosphatase 1B, each of which is a major target of diabetes treatment. Chrysophanol-8-O-beta-D-glucopyranoside up to 25 microM dose-dependently activated glucose transport in insulin-stimulated myotubes. Increased tyrosine phosphorylation of IR due to tyrosine phosphatase 1B inhibitory activity with an IC50 value of 18.34+/-0.29 microM and unchanged Glut4 mRNA levels was observed following chrysophanol-8-O-beta-D-glucopyranoside treatment. Chrysophanol up to 100 microM exerted mild glucose transport activity and elevated the tyrosine phosphorylation of IR via tyrosine phosphatase 1B inhibition (IC50=79.86+/-0.12 microM); Glut4 mRNA expression was also significantly increased by 100 microM. The ED50 values of the two compounds were 59.38+/-0.66 and 79.69+/-0.03 microM, respectively. Therefore, these two anthraquinones from rhubarb rhizome, chrysophanol-8-O-beta-D-glucopyranoside and chrysophanol, have mild cytotoxicity and anti-diabetic properties and could play metabolic roles in the insulin-stimulated glucose transport pathway.

Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities.[Pubmed:22302018]

J Pharmacol Sci. 2012;118(2):245-54. Epub 2012 Feb 3.

Rhubarb is a widely used traditional medicine and has been reported to elicit a number of biological effects including anti-inflammatory and antiplatelet effects. In the present study, we investigated the effects of anthraquinone derivatives isolated from rhubarb on platelet activity. Of four anthraquinone derivatives isolated from rhubarb examined, chrysophanol-8-O-glucoside (CP-8-O-glc) was found to have the most potent inhibitory effect on collagen- and thrombin-induced platelet aggregation. CP-8-O-glc-treated mice showed significantly prolonged bleeding times. Furthermore, CP-8-O-glc was found to have a significant inhibitory effect on rat platelet aggregation ex vivo and on thromboxane A(2) formation in vitro. In coagulation tests, CP-8-O-glc did not alter prothrombin time, and it prolonged the activated partial thromboplastin time. However, CP-8-O-glc only inhibited platelet phosphatidylserine exposure, but not exert direct inhibition on intrinsic factors. This study demonstrates the antiplatelet and anticoagulant effects of CP-8-O-glc and suggests that this compound might be of therapeutic benefit for the prevention of platelet-related cardiovascular diseases.

Description

Chrysophanol 8-O-glucoside, from the roots of Rumex acetosa, shows moderate elastase inhibition activity.

Keywords:

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