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

The chemical composition of a hexanic extract of <i>Eryngium campestre</i>, 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-&#946;-ol (8.2%) and falcarindiol (9.4%), wh...

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Bibliographic Details
Published in:Molecules
Main Authors: Ali Medbouhi, Aura Tintaru, Claire Beaufay, Jean-Valère Naubron, Nassim Djabou, Jean Costa, Joëlle Quetin-Leclercq, Alain Muselli
Format: Article
Language:English
Published: MDPI AG 2018-12-01
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Online Access:https://www.mdpi.com/1420-3049/23/12/3250
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Summary:The chemical composition of a hexanic extract of <i>Eryngium campestre</i>, 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-&#946;-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 (<i>Trypanosoma brucei brucei</i>), antileishmanial (<i>Leishmania mexicana mexicana</i>) and anticancer (cancerous macrophage-like murine cells) activities, and also displayed cytotoxicity, (human normal fibroblasts) in similar concentration ranges (IC<sub>50</sub> = 3.0, 3.9, 4.0 and 4.4 &#181;g/mL respectively). Likewise, campestrolide displayed low activity on all tested cells (IC<sub>50</sub>: 12.5&#8315;19.5 &#181;M) except on <i>Trypanosoma</i>, on which it was very active and moderately selective (IC<sub>50</sub> = 2.2 &#181;M. 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.
ISSN:1420-3049