2. Academic Validation
  3. The chemical and biological potential of C ring modified triterpenoids

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.
Bianka Siewert 1,  Jana Wiemann 1,  Alexander Köwitsch 1,  René Csuk 2
Affiliations

Affiliations

  • 1 Bereich Organische Chemie, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120 Halle, Saale, Germany.
  • 2 Bereich Organische Chemie, Martin-Luther-Universität Halle-Wittenberg, Kurt-Mothes-Str. 2, D-06120 Halle, Saale, Germany. Electronic address: rene.csuk@chemie.uni-halle.de.
PMID: 24361521 DOI: 10.1016/j.ejmech.2013.11.025
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.

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