Chrysophanol

Chrysophanol
Names
	IUPAC name 1,8-Dihydroxy-3-methyl-9,10-anthraquinone
Identifiers
CAS Number	481-74-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3687;
ChemSpider	9793;
ECHA InfoCard	100.006.885
KEGG	C10315;
PubChem CID	10208;
UNII	N1ST8V8RR2 ;
CompTox Dashboard (EPA)	DTXSID6024832 ;
	InChI InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3 Key: LQGUBLBATBMXHT-UHFFFAOYSA-N; InChI=1/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3 Key: LQGUBLBATBMXHT-UHFFFAOYAW;
	SMILES CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O;
Properties
Chemical formula	C15H10O4
Molar mass	254.241 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone.

Mechanism of action

Chrysophanol blocks the proliferation of colon cancer cells in vitro.[1] It induces the necrosis of cells via a reduction in ATP levels.[2] Chrysophanol attenuates the effects of lead exposure in mice by reducing hippocampal neuronal cytoplasmic edema, enhancing mitochondrial crista fusion, significantly increasing memory and learning abilities, reducing lead content in blood, heart, brain, spleen, kidney and liver, promoting superoxide dismutase and glutathione peroxidase activities and reducing malondialdehyde level in the brain, kidney and liver.[3]

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References

Lee, MS; Cha, EY; Sul, JY; Song, IS; Kim, JY (2011). "Chrysophanic acid blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway". Phytotherapy Research. 25 (6): 833–7. doi:10.1002/ptr.3323. PMID 21089180.
Burnstock, G; Di Virgilio, F (Dec 2013). "Purinergic signalling and cancer". Purinergic Signalling. 9 (4): 491–540. doi:10.1007/s11302-013-9372-5. PMC 3889385. PMID 23797685.
Zhang, J; Yan, C; Wang, S; Hou, Y; Xue, G; Zhang, L (2014). "Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice". Neural Regeneration Research. 9 (9): 924–30. doi:10.4103/1673-5374.133141. PMC 4146226. PMID 25206913.

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[1] Lee, MS; Cha, EY; Sul, JY; Song, IS; Kim, JY (2011). "Chrysophanic acid blocks proliferation of colon cancer cells by inhibiting EGFR/mTOR pathway". Phytotherapy Research. 25 (6): 833–7. doi:10.1002/ptr.3323. PMID 21089180.

[purinergic-2] Burnstock, G; Di Virgilio, F (Dec 2013). "Purinergic signalling and cancer". Purinergic Signalling. 9 (4): 491–540. doi:10.1007/s11302-013-9372-5. PMC 3889385. PMID 23797685.

[3] Zhang, J; Yan, C; Wang, S; Hou, Y; Xue, G; Zhang, L (2014). "Chrysophanol attenuates lead exposure-induced injury to hippocampal neurons in neonatal mice". Neural Regeneration Research. 9 (9): 924–30. doi:10.4103/1673-5374.133141. PMC 4146226. PMID 25206913.