The chemical and biological potential of C ring modified triterpenoids

Eur J Med Chem. 2014 Jan 24:72:84-101. doi: 10.1016/j.ejmech.2013.11.025. Epub 2013 Dec 5.

Abstract

A convenient and elegant route has been developed to separate the natural regioisomers triterpenoids ursolic acid (UA) and oleanolic acid (OA) as well as derivatives thereof. Eleven unknown derivatives of OA were designed, synthesized, and their cytotoxicity was investigated. Further sixteen compounds were prepared to correlate all compounds in a SAR study. It could be shown that C-ring modifications of OA and UA have only a moderate influence onto the cytotoxic activity of the compounds but a significant impact onto the ability to trigger apoptosis in ovarian cancer cells (cell line A2780).

Keywords: Antitumor activity; Apoptosis; Oleanolic acid acid; Structure–activity relationships; Triterpenoids; Ursolic acid.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemical synthesis
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Apoptosis / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • MCF-7 Cells
  • Mice
  • Molecular Conformation
  • NIH 3T3 Cells
  • Oleanolic Acid / chemical synthesis
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / pharmacology*
  • Structure-Activity Relationship
  • Triterpenes / chemical synthesis
  • Triterpenes / chemistry
  • Triterpenes / pharmacology*
  • Ursolic Acid

Substances

  • Antineoplastic Agents, Phytogenic
  • Triterpenes
  • Oleanolic Acid