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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
Structure of EMODIN-8-GLUCOSIDE

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

HIDE SMILES / InChI

Molecular Formula C21H20O10
Molecular Weight 432.3775
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
[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
[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

Patents

Sample Use Guides

in rats: emodin-8-O-β-D-glucoside-treated groups (2.5, 5, 10 mg/kg)
Route of Administration: Intravenous
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:16:53 GMT 2023
Edited
by admin
on Fri Dec 15 20:16:53 GMT 2023
Record UNII
YY0Q8Q1T3H
Record Status Validated (UNII)
Record Version
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Name Type Language
EMODIN-8-GLUCOSIDE
Common Name English
EMODIN 8-O-.BETA.-D-GLUCOSIDE
Common Name English
EMODIN 8-.BETA.-D-GLUCOSIDE
Common Name English
9,10-ANTHRACENEDIONE, 1-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,8-DIHYDROXY-6-METHYL-
Common Name English
EMODIN-1 (8)-MONOGLUCOSIDE
Common Name English
3,8-DIHYDROXY-6-METHYL-1-ANTHRAQUINONYL-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
1-(.BETA.-D-GLUCOPYRANOSYLOXY)-3,8-DIHYDROXY-6-METHYL-9,10-ANTHRACENEDIONE
Systematic Name English
NSC-257449
Code English
EMODIN GLUCOSIDE B
Common Name English
8-O-.BETA.-D-GLUCOPYRANOSYLEMODIN
Common Name English
EMODIN 8-O-GLUCOSIDE
Common Name English
EMODIN 8-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
EMODIN-8-O-.BETA.-D-GLUCOSIDE
Common Name English
ANTHRAGLYCOSIDE B
Common Name English
GLUCOPYRANOSIDE, 3,8-DIHYDROXY-6-METHYL-1-ANTHRAQUINONYL, .BETA.-D-
Common Name English
EMODIN 8-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
Code System Code Type Description
NSC
257449
Created by admin on Fri Dec 15 20:16:53 GMT 2023 , Edited by admin on Fri Dec 15 20:16:53 GMT 2023
PRIMARY
CAS
23313-21-5
Created by admin on Fri Dec 15 20:16:53 GMT 2023 , Edited by admin on Fri Dec 15 20:16:53 GMT 2023
PRIMARY
FDA UNII
YY0Q8Q1T3H
Created by admin on Fri Dec 15 20:16:53 GMT 2023 , Edited by admin on Fri Dec 15 20:16:53 GMT 2023
PRIMARY
PUBCHEM
99649
Created by admin on Fri Dec 15 20:16:53 GMT 2023 , Edited by admin on Fri Dec 15 20:16:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID60945988
Created by admin on Fri Dec 15 20:16:53 GMT 2023 , Edited by admin on Fri Dec 15 20:16:53 GMT 2023
PRIMARY
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