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


ABSTRACT: 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-?-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.

SUBMITTER: Medbouhi A 

PROVIDER: S-EPMC6321439 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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

Medbouhi Ali A   Tintaru Aura A   Beaufay Claire C   Naubron Jean-Valère JV   Djabou Nassim N   Costa Jean J   Quetin-Leclercq Joëlle J   Muselli Alain A  

Molecules (Basel, Switzerland) 20181208 12


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-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 antitrypanoso  ...[more]

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