2. Academic Validation
  3. Hederagenin as a triterpene template for the development of new antitumor compounds

Hederagenin as a triterpene template for the development of new antitumor compounds

  • Eur J Med Chem. 2015 Nov 13;105:57-62. doi: 10.1016/j.ejmech.2015.10.006.
Diego Rodríguez-Hernández 1,  Antonio J Demuner 2,  Luiz C A Barbosa 3,  René Csuk 4,  Lucie Heller 5
Affiliations

Affiliations

  • 1 Department of Chemistry, Universidade Federal de Viçosa, Av. P. H. Rolfs, s/n, CEP 36570-900, Viçosa, MG, Brazil; Department of Chemistry, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos 6627, Campus Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil.
  • 2 Department of Chemistry, Universidade Federal de Viçosa, Av. P. H. Rolfs, s/n, CEP 36570-900, Viçosa, MG, Brazil.
  • 3 Department of Chemistry, Universidade Federal de Viçosa, Av. P. H. Rolfs, s/n, CEP 36570-900, Viçosa, MG, Brazil; Department of Chemistry, Universidade Federal de Minas Gerais, Av. Pres. Antônio Carlos 6627, Campus Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil. Electronic address: [email protected].
  • 4 Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str.2, D-06120, Halle (Saale), Germany. Electronic address: [email protected].
  • 5 Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str.2, D-06120, Halle (Saale), Germany.
PMID: 26476750 DOI: 10.1016/j.ejmech.2015.10.006
Abstract

In this study, a series of novel C-28 esters and amides derivatives of hederagenin (He) were designed and synthesized in attempt to develop potent antitumor agents. Their structures were confirmed by MS, IR, (1)H NMR and (13)C NMR spectroscopic analyses and their cytotoxic activities were screened in SRB assays using a panel of six human Cancer cell lines. Although most of the compounds displayed moderate to high levels of cytotoxic activity they were all more potent than the natural product He. The most active compounds had either an ethylpyrimidinyl (27) or an ethylpyrrolidinyl (28) substituent, with EC50 in the range of 1.1-6.5 μM for six human Cancer cell lines. Notably, this corresponds to an approximately 30-fold times greater potency than He.

Keywords

Folk medicinal plant; Hederagenin derivatives; Pentacyclic triterpenes; SRB assay; Sapindus saponaria.

Figures
Products