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Structure Database (LMSD)

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Common Name

Emodin 8-glucoside

Systematic Name

Synonyms

LM ID

LMPK13040009

Formula

C₂₁H₂₀O₁₀

Exact Mass

Calculate m/z

432.10565

Status

Curated

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Classification

Biological Context

Emodin 8-glucoside is an anthraquinone glycoside that has been found in R. japonica and has diverse biological activities.^1,2,3,4 It inhibits the activities of rat lens aldose reductase and human DNA topoisomerase II (IC50s = 14.4 and 66 μM, respectively, in cell-free assays).^1,2 Emodin 8-glucoside (1 ng/ml) promotes the proliferation and differentiation of mouse MC3T3-E1 osteoblastic cells.³ It also decreases infarct size in a rat model of focal cerebral ischemia and reperfusion injury when administered at a dose of 5 mg/kg.⁴

This information has been provided by Cayman Chemical

References

1. Kim, J.M., Jamg, D.S., Lee, Y.M., et al. Constituents of the fruits of Rumex japonicus with inhibitory activity on aldose reductase. J. Appl. Biol. Chem. 51(1), 13-16 (2008).

2. Hwangbo, K., Zheng, M.S., Kim, Y.-J., et al. Inhibition of DNA topoisomerases I and II of compounds from Reynoutria japonica. Arch. Pharm. Res. 35(9), 1583-1589 (2012).

3. Xiang, M.-X., Xu, Z., Su, H.-W., et al. Emodin-8-O-β-D-glucoside from Polygonum amplexicaule D. Don var. sinense Forb. promotes proliferation and differentiation of osteoblastic MC3T3-E1 cells. Molecules 16(1), 728-737 (2011).

4. Wang, C., Zhang, D., Ma, H., et al. Neuroprotective effects of emodin-8-O-β-D-glucoside in vivo and in vitro. Eur. J. Pharmacol. 577(1-3), 58-63 (2007).

String Representations

InChiKey (Click to copy)

HSWIRQIYASIOBE-JNHRPPPUSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C12C(=O)C3=C(C=C(C=C3O)C)C(=O)C=1C=C(C=C2O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)O