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Molecules 2018, 23(12), 3250;

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

Laboratoire de Chimie Organique Substances Naturelles et Analyses (COSNA), Département de Chimie, Faculté des Sciences, Université de Tlemcen, BP 119, Tlemcen 13000, Algeria
Laboratoire Chimie des Produits Naturels (CPN), Campus Grimaldi, Université de Corse, UMR CNRS 6134 SPE, BP 52, 20250 Corte, France
Aix Marseille Univ, CNRS, Institut de Chimie Radicalaire, UMR 7273, 13397 Marseille, France
UCLouvain, Louvain Drug Research Institute, Pharmacognosy Group, Avenue E. Mounier, 72, bte B1.7203, B-1200 Bruxelles, Belgium
Centrale Marseille, Aix Marseille Univ, CNRS, FSCM, Spectropole, Marseille 13397, France
Authors to whom correspondence should be addressed.
Received: 10 November 2018 / Revised: 1 December 2018 / Accepted: 6 December 2018 / Published: 8 December 2018
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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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