Fig 1.
Chemical structure of anthraquinone compounds 1–8.
(1) nordamnacanthal, (2) damnacanthal, (3) 1,3,5-dihydoxy-2-methoxy-6-methyl anthraquinone, (4) morindone, (5) sorendidiol, (6) rubiadin, (7) damnacanthol, and (8) lucidin-ω-methylether.
Fig 2.
Docking complex of morindone (cyan) and rubiadin (yellow) against β-catenin, MDM2-p53, and KRAS.
The TCF cofactor in β-catenin was shown in red. Molecular surface regarding residues type at the binding residues within 3 Å from compounds were illustrated. Amino acid residue types were colored by YASARA coloring scheme: nonpolar, grey; amidic, green; basic, blue; acidic, red; hydroxylic, cyan.
Fig 3.
Two-dimensional diagram of residues binding interaction of morindone and rubiadin with β-catenin (Site A), MDM2-p53, and KRAS.
Each residue is colored by the type of interaction; van der Waals (light green), hydrogen bond (green), and polar (magenta and orange).
Table 1.
Binding affinity of anthraquinone compounds 1–8 towards β-catenin, MDM2-p53 and KRAS in colorectal cancer.
Fig 4.
Cytotoxicity effect of anthraquinone compounds 1–8 on the cell viability of HCT116 cells.
Data was shown as mean ± SD from three independent experiments.
Fig 5.
Cytotoxicity effect of anthraquinone compounds 1–8 on the cell viability of LS174T cells.
Data was shown as mean ± SD from three independent experiments.
Fig 6.
Cytotoxicity effect of anthraquinone compounds 1–8 on the cell viability of HT29 cells.
Data was shown as mean ± SD from three independent experiments.
Fig 7.
Cytotoxicity effect of anthraquinone compounds 1–8 on the cell viability of CCD841 CoN cells.
Data was shown as mean ± SD from three independent experiments.
Table 2.
IC50 value of anthraquinone compounds 1–8, 5-Fluorouracil, doxorubicin hydrochloride in three colorectal cancer cell lines and normal colon cells.
Table 3.
Selectivity index (SI) of normal colon cells against colorectal cancer cells.
Table 4.
IC50 and combination index (CI) values.
Fig 8.
Characterization of morindone.
(A) FTIR spectrum of morindone. (B) GC-MS chromatogram of morindone. (C) 1H NMR spectra of morindone in Acetone-d6. (D) 13C NMR spectra of morindone in Acetone-d6.