Structural Elucidation and Cytotoxicity of a New 17-Membered Ring Lactone from Algerian <i>Eryngium campestre</i>
Ali Medbouhi,
Aura Tintaru,
Claire Beaufay,
Jean-Valère Naubron,
Nassim Djabou,
Jean Costa,
Joëlle Quetin-Leclercq,
Alain Muselli
Affiliations
Ali Medbouhi
Laboratoire de Chimie Organique Substances Naturelles et Analyses (COSNA), Département de Chimie, Faculté des Sciences, Université de Tlemcen, BP 119, Tlemcen 13000, Algeria
Aura Tintaru
Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, 13397 Marseille, France
Claire Beaufay
UCLouvain, Louvain Drug Research Institute, Pharmacognosy Group, Avenue E. Mounier, 72, bte B1.7203, B-1200 Bruxelles, Belgium
Jean-Valère Naubron
Centrale Marseille, Aix Marseille Univ, CNRS, FSCM, Spectropole, Marseille 13397, France
Nassim Djabou
Laboratoire de Chimie Organique Substances Naturelles et Analyses (COSNA), Département de Chimie, Faculté des Sciences, Université de Tlemcen, BP 119, Tlemcen 13000, Algeria
Jean Costa
Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Université de Corse, UMR CNRS 6134 SPE, BP 52, 20250 Corte, France
Joëlle Quetin-Leclercq
UCLouvain, Louvain Drug Research Institute, Pharmacognosy Group, Avenue E. Mounier, 72, bte B1.7203, B-1200 Bruxelles, Belgium
Alain Muselli
Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Université de Corse, UMR CNRS 6134 SPE, BP 52, 20250 Corte, France
The chemical composition of a hexanic extract of Eryngium campestre, obtained from its aerial parts, was investigated by GC-FID, GC/MS, HRMS, NMR and VCD analyses. The main compounds were germacrene D (23.6%), eudesma-4(15)-7-dien-1-β-ol (8.2%) and falcarindiol (9.4%), which are associated with a new uncommon and naturally found 17-membered ring lactone. This 17-membered ring features conjugated acetylenic bonds, named campestrolide (23.0%). The crude extract showed moderate antitrypanosomal (Trypanosoma brucei brucei), antileishmanial (Leishmania mexicana mexicana) and anticancer (cancerous macrophage-like murine cells) activities, and also displayed cytotoxicity, (human normal fibroblasts) in similar concentration ranges (IC50 = 3.0, 3.9, 4.0 and 4.4 µg/mL respectively). Likewise, campestrolide displayed low activity on all tested cells (IC50: 12.5⁻19.5 µM) except on Trypanosoma, on which it was very active and moderately selective (IC50 = 2.2 µM. SI= 8.9). In conclusion, the new compound that has been described, displaying a singular structure, possesses interesting antitrypanosomal activity that should be further investigated and improved.
