Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H20O10 |
Molecular Weight | 432.3775 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(O)=C2C(=O)C3=C(C=C(O)C=C3O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(=O)C2=C1
InChI
InChIKey=HSWIRQIYASIOBE-JNHRPPPUSA-N
InChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21-/m1/s1
Emodin-8-O-beta-D-glucoside extracted from the traditional Chinese medicinal herb Polygonum cuspidatum Sieb. et Zucc, which is used to treat fractures, rheumatoid arthritis, muscle injury and pain possible by antioxidative mechanism. Emodin-8-O-beta-D-glucoside can be a promising antitumor agent for cancer treatment, because experiments with cervical cancer SKOV3 cells have shown, that it can inhibit the proliferation of cells and promote apoptosis by down regulation of Bcl-2 expression and up regulation of Bax expression, as well as the increase of relative activity of caspase 3 and caspase 9. In addition, emodin-8-O-beta-D-glucoside is able to provide neuroprotection against cerebral ischemia-reperfused injury and glutamate induced neuronal damage through exerting antioxidative effects and inhibiting glutamate neurotoxicity.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17897641
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Large-scale separation of resveratrol, anthraglycoside A and anthraglycoside B from Polygonum cuspidatum Sieb. et Zucc by high-speed counter-current chromatography. | 2001 Jun 15 |
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[Simultaneous determination of contents of five major bioactive components contained in Polygoni Cuspidati Rhizoma et Radix by microwave extraction-ultra performance liquid chromatography]. | 2012 Jul |
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[Distribution laws of 5 compounds in rhizome and root of Polygonum cuspidate]. | 2015 Dec |
|
[Effects of emodin-8-O-β-D-glucoside on cell apoptosis and expression of Bcl-2/Bax in cervical cancer SKOV3 cells]. | 2015 Nov 17 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17897641
in rats: emodin-8-O-β-D-glucoside-treated groups (2.5, 5, 10 mg/kg)
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21245807
Emodin-8-O-β-D-glucoside (EG) promotes proliferation and differentiation of osteoblastic MC3T3-E1 cells. EG significantly promoted cell proliferation of cells at 0.1-100 ng/mL, and increased the cell proportion in S-phase from 16.34% to 32.16%. Moreover, EG increased alkaline phosphatase (ALP) expression in MC3T3-E1 cells at the concentration from 0.1 to 100 ng/mL and inhibited PGE(2)production induced by TNF-α in osteoblasts at the concentrations ranging from 10-100 ng/mL, suggesting that cell differentiation was induced in MC3T3-E1 osteoblasts
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SUBSTANCE RECORD