Emodin-8-glucoside

Emodin-8-glucoside
Identifiers
	IUPAC name 1,6-dihydroxy-3-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione;
CAS Number	23313-21-5;
PubChem CID	99649;
ChemSpider	90027;
UNII	YY0Q8Q1T3H;
KEGG	C10345;
ChEBI	CHEBI:4783;
ChEMBL	ChEMBL464360;
CompTox Dashboard (EPA)	DTXSID60945988 ;
Chemical and physical data
Formula	C21H20O10
Molar mass	432.381 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O;
	InChI 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; Key:HSWIRQIYASIOBE-JNHRPPPUSA-N;

Emodin-8-glucoside is a natural product found in various plants used in traditional herbal medicine such as Aloe vera and Rheum officinale. It has antiviral effects, and has a complex mechanism of action, acting as a 5-HT_1B agonist as well as an activator of PPARα/γ and AMPK.^[1]^[2]

Biosynthesis

The enzyme hydroxyanthraquinone glucosyltransferase, characterised from Cinchona succiruba, converts the hydroxyanthraquinone, emodin,^[3] to its glucosylated derivative, emodin-8-glucoside. The glucose unit is transferred from UDP-glucose, with uridine diphosphate (UDP) as byproduct.^[4]

emodin

+ UDP-glucose

UDP

Rightward reaction arrow with minor product(s) to top right

emodin-8-glucoside

References

↑ Bei Y, Tia B, Li Y, Guo Y, Deng S, Huang R, et al. (2021). "Anti-influenza A Virus Effects and Mechanisms of Emodin and Its Analogs via Regulating PPARα/γ-AMPK-SIRT1 Pathway and Fatty Acid Metabolism". BioMed Research International. 2021 9066938. doi:10.1155/2021/9066938. PMC 8445710. PMID 34540999.
↑ Zhang K, Sun L, Zhang W, Cao M, Ma X, Yu BY, et al. (April 2024). "Discovery of Natural Products Alleviating Renal Fibrosis with a Viscosity-Responsive Molecular Probe". Analytical Chemistry. 96 (16): 6356–6365. doi:10.1021/acs.analchem.4c00188. PMID 38588440.
↑ Tsay HS, Shyur LF, Agrawal DC, Wu YC, Wang SY (3 November 2017). Medicinal Plants – Recent Advances in Research and Development. Singapore: Springer Singapore. p. 339. ISBN 978-981-10-5978-0.
↑ Khouri HE, Ibrahim RK (1987). "Purification and some properties of five anthraquinone-specific glucosyltransferases from Cinchona succiruba cell suspension culture". Phytochemistry. 26 (9): 2531–2535. Bibcode:1987PChem..26.2531K. doi:10.1016/S0031-9422(00)83870-4.

[1] Bei Y, Tia B, Li Y, Guo Y, Deng S, Huang R, et al. (2021). "Anti-influenza A Virus Effects and Mechanisms of Emodin and Its Analogs via Regulating PPARα/γ-AMPK-SIRT1 Pathway and Fatty Acid Metabolism". BioMed Research International. 2021 9066938. doi:10.1155/2021/9066938. PMC 8445710. PMID 34540999.

[2] Zhang K, Sun L, Zhang W, Cao M, Ma X, Yu BY, et al. (April 2024). "Discovery of Natural Products Alleviating Renal Fibrosis with a Viscosity-Responsive Molecular Probe". Analytical Chemistry. 96 (16): 6356–6365. doi:10.1021/acs.analchem.4c00188. PMID 38588440.

[3] Tsay HS, Shyur LF, Agrawal DC, Wu YC, Wang SY (3 November 2017). Medicinal Plants – Recent Advances in Research and Development. Singapore: Springer Singapore. p. 339. ISBN 978-981-10-5978-0.

[4] Khouri HE, Ibrahim RK (1987). "Purification and some properties of five anthraquinone-specific glucosyltransferases from Cinchona succiruba cell suspension culture". Phytochemistry. 26 (9): 2531–2535. Bibcode:1987PChem..26.2531K. doi:10.1016/S0031-9422(00)83870-4.

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Emodin-8-glucoside

Biosynthesis

References