Synthesis of cytotoxic and antioxidant Schiff's base analogs of aloin

J Asian Nat Prod Res. 2010 May;12(5):360-70. doi: 10.1080/10286021003775327.

Abstract

Aloin (10-glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthracenone), a bioactive compound in Aloe vera, although known to have an anticancer effect, has not been used in current drug research. Optimization of the lead structure could enhance the utility of this compound. Hence, aloin was modified using natural amino acids to produce Schiff's base, a potential pharmacophore, and its corresponding aglycones. The synthetic derivatives exhibited significant enhancement in their efficacy toward antioxidant (DPPH radical scavenging) and cytotoxic activities than those of the parent compound, aloin showing promise for application in cancer treatment.

MeSH terms

  • Aloe / chemistry
  • Animals
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Artemia / drug effects
  • Biphenyl Compounds / pharmacology
  • Combinatorial Chemistry Techniques
  • Emodin / analogs & derivatives*
  • Emodin / chemical synthesis
  • Emodin / chemistry
  • Emodin / pharmacology
  • Molecular Structure
  • Picrates / pharmacology
  • Plants, Medicinal / chemistry
  • Schiff Bases / pharmacology

Substances

  • Antineoplastic Agents, Phytogenic
  • Antioxidants
  • Biphenyl Compounds
  • Picrates
  • Schiff Bases
  • 1,1-diphenyl-2-picrylhydrazyl
  • Emodin
  • alloin