Chrysophanic acid

Chrysophanic acid

Names
IUPAC name 1,8-Dihydroxy-3-methyl-9,10-anthraquinone
Identifiers
ChEBI	CHEBI:3687
ChemSpider	9793
Jmol interactive 3D	Image
PubChem	10208
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	254.24 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

Chrysophanic acid, also known as chrysophanol, is a fungal isolate and a natural anthraquinone with anti-cancer activity.^[1]

Drug action

Chrysophanol induces the necrosis of cancer cells via a reduction in ATP levels.^[2] Chrysophanol attentuates 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]

Notes

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 : PTR 25 (6): 833–7. doi:10.1002/ptr.3323. PMID 21089180.
2. Burnstock, G; Di Virgilio, F (Dec 2013). "Purinergic signalling and cancer.". Purinergic Signalling (journal) 9 (4): 491–540. doi:10.1007/s11302-013-9372-5. PMC 3889385. PMID 23797685.
3. In lead-exposed neonatal mice, chrysophanol attenuates injury to hippocampal neurons. Zhang et al. (2014) http://www.medicalnewstoday.com/releases/279724.php