Preparation of 1,8-di-O-alkylaloe-emodins and 15-amino-, 15-thiocyano-, and 15-selenocyanochrysophanol derivatives from aloe-emodin and studying their cytotoxic effects

Chem Pharm Bull (Tokyo). 2008 Apr;56(4):497-503. doi: 10.1248/cpb.56.497.


1,8-di-O-alkylaloe-emodin derivatives (namely, methyl-, propyl-, hexyl-, dodecyl-, and octadecyl) were synthesized from naturally occurring aloe-emodin. Further, derivatives having various substituents such as diethylamino, pyrrolidinyl, piperidinyl, methylpiperazinyl, imidazolyl, thiocyano and selenocyano groups at the 15 position of chrysophanol and 1,8-di-O-hexylchrysophanol from aloe-emodin were synthesized. The cytotoxic effects of these derivatives on less P-glycoprotein (P-gp)-expressing HCT 116 cells and stably P-gp-expressing Hep G2 cells were evaluated by performing 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Among these products, several of them exhibited markedly higher potent cytotoxic effects not only on HCT116 cells but also Hep G2 cancer cells as compared to aloe-emodin.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / metabolism
  • Aloe / chemistry
  • Anthraquinones / chemistry*
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Drug Screening Assays, Antitumor
  • Humans
  • Magnetic Resonance Spectroscopy
  • Organoselenium Compounds / chemistry*
  • Organoselenium Compounds / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrometry, Mass, Fast Atom Bombardment
  • Tetrazolium Salts
  • Thiazoles


  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Anthraquinones
  • Antineoplastic Agents, Phytogenic
  • Organoselenium Compounds
  • Tetrazolium Salts
  • Thiazoles
  • aloe emodin
  • thiazolyl blue