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Chrysophanol-8-O-β-D-glucoside

$560

  • Brand : BIOFRON

  • Catalogue Number : BD-P0934

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 13241-28-6

  • PUBCHEM ID : 442731

  • Volume : 25mg

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Catalogue Number

BD-P0934

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

Appearance

Light yellow powder

Botanical Source

Rheum palmatum L./Rheum, Rhamnus, Rumex spp. and other plant spp.

Structure Type

Anthraquinones

Category

Standards;Natural Pytochemical;API

SMILES

CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3OC4C(C(C(C(O4)CO)O)O)O

Synonyms

8-Hydroxy-6-methyl-9,10-dioxo-9,10-dihydro-1-anthracenyl β-D-glucopyranoside/1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione/chrysophanol 8-O-beta-D-glucoside/Chrysophanol 8-O-β-D-glucoside/Chrysophanol-8-O-Beta-D-glucopyranoside/Chrysophanol 8-O-glucoside/Chryohol-8-O-Beta-D-glucoyroide/9,10-Anthracenedione, 8-(β-D-glucopyranosyloxy)-1-hydroxy-3-methyl-/chrysophanein/8-O-D-glucopyranosyl-1-hydroxy-3-methylanthraquinone/Chrysophanol 8-glucoside/Pulmatin/Chrysophanol-8-O-β-D-glucoside

IUPAC Name

1-hydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione

Applications

Chrysophanol-8-O-glucoside, an anthraquinone derivative in rhubarb, has antiplatelet and anticoagulant activities. PUMID/DOI: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. 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. 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. PUMID/DOI: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. 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. 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. PUMID/DOI: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). 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. 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.

Density

1.6±0.1 g/cm3

Solubility

Methanol

Flash Point

272.8±26.4 °C

Boiling Point

763.2±60.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

WMMOMSNMMDMSRB-JNHRPPPUSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

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