Description
Chrysophanic acid (Chrysophanol) is a natural anthraquinone with anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid preferentially blocked proliferation in SNU-C5 cells but not in other cell lines (HT7, HT29, KM12C, SW480, HCT116 and SNU-C4) with low levels of EGFR expression. Chrysophanic acid treatment in SNU-C5 cells inhibited EGF-induced phosphorylation of EGFR and suppressed activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanic acid (80 and 120 µm) significantly blocked cell proliferation when combined with the mTOR inhibitor, rapamycin. These findings offer the first evidence of anticancer activity for chrysophanic acid via EGFR/mTOR mediated signaling transduction pathway. Chrysophanol is a natural compound found in the roots and rhizomes of Rheum palmatum L. It can be used in cosmetics material.
Synonyms
1,8-dihydroxy-3-methylanthracene-9,10-dione
IUPAC Name
1,8-dihydroxy-3-methylanthracene-9,10-dione
Molecular Formula
C15H10O4
Canonical SMILES
CC1=CC(=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)O)O
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
InChIKey
LQGUBLBATBMXHT-UHFFFAOYSA-N
Density
0.92 g/cm cu at 25 °C
Solubility
less than 1 mg/mL at 64 °F
Application
anti-inflammatory
Stability
Stable under recommended storage conditions
Vapor Pressure
3.69X10-10 mm Hg at 25 °C (est)