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Structural Elucidation and Cytotoxicity of a New 17-Membered Ring Lactone from Algerian Eryngium campestre

1
Laboratoire de Chimie Organique Substances Naturelles et Analyses (COSNA), Département de Chimie, Faculté des Sciences, Université de Tlemcen, BP 119, Tlemcen 13000, Algeria
2
Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Université de Corse, UMR CNRS 6134 SPE, BP 52, 20250 Corte, France
3
Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, 13397 Marseille, France
4
UCLouvain, Louvain Drug Research Institute, Pharmacognosy Group, Avenue E. Mounier, 72, bte B1.7203, B-1200 Bruxelles, Belgium
5
Centrale Marseille, Aix Marseille Univ, CNRS, FSCM, Spectropole, Marseille 13397, France
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(12), 3250; https://doi.org/10.3390/molecules23123250
Received: 10 November 2018 / Revised: 1 December 2018 / Accepted: 6 December 2018 / Published: 8 December 2018
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. View Full-Text
Keywords: Eryngium campestre; 17-membered ring lactone; cytotoxicity; Trypanosoma; Leishmania Eryngium campestre; 17-membered ring lactone; cytotoxicity; Trypanosoma; Leishmania
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Medbouhi, A.; Tintaru, A.; Beaufay, C.; Naubron, J.-V.; Djabou, N.; Costa, J.; Quetin-Leclercq, J.; Muselli, A. Structural Elucidation and Cytotoxicity of a New 17-Membered Ring Lactone from Algerian Eryngium campestre. Molecules 2018, 23, 3250.

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