Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i>
In continuing our investigation on the chemical diversity of Algerian plants, we examined <i>Centaurea omphalotricha</i>, whose chemical composition has been poorly studied. The present work was aimed at characterizing the secondary metabolite pattern of the CHCl<sub>3</sub>...
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MDPI AG
2021-07-01
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| Series: | Biomolecules |
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| Online Access: | https://www.mdpi.com/2218-273X/11/7/1053 |
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| author | Sara Kebbi Maria Letizia Ciavatta Ali Mokhtar Mahmoud Marianna Carbone Alessia Ligresti Ramdane Seghiri Margherita Gavagnin |
| author_facet | Sara Kebbi Maria Letizia Ciavatta Ali Mokhtar Mahmoud Marianna Carbone Alessia Ligresti Ramdane Seghiri Margherita Gavagnin |
| author_sort | Sara Kebbi |
| collection | DOAJ |
| description | In continuing our investigation on the chemical diversity of Algerian plants, we examined <i>Centaurea omphalotricha</i>, whose chemical composition has been poorly studied. The present work was aimed at characterizing the secondary metabolite pattern of the CHCl<sub>3</sub> extract of the aerial parts of this plant that displayed antiproliferative properties in a preliminary screening on HeLa cell line. The chemical analysis led us to characterize the bioactive oxygenated terpenoid fraction which includes, within major known metabolites, two new minor sesquiterpene lactones, centaurolide-A (<b>1</b>) and centaurolide-B (<b>2</b>). The structures of two compounds exhibiting the 12,8-guaianolide skeleton were determined by spectroscopic methods as well as by chemical correlation with inuviscolide (<b>3</b>), a well-known bioactive guaianolide isolated from <i>Dittrichia</i> (=<i>Inula</i>) <i>viscosa</i>. Centaurolides A and B represent the first report of 8,12-guaianolide skeleton in <i>Centaurea</i> genus. The effect of new compounds <b>1</b> and <b>2</b> and inuviscolide (<b>3</b>) on HeLa cell has also been evaluated. |
| first_indexed | 2024-03-10T09:45:06Z |
| format | Article |
| id | doaj.art-7ced6a5d5d6f413cba94849712985607 |
| institution | Directory Open Access Journal |
| issn | 2218-273X |
| language | English |
| last_indexed | 2024-03-10T09:45:06Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biomolecules |
| spelling | doaj.art-7ced6a5d5d6f413cba948497129856072023-11-22T03:19:30ZengMDPI AGBiomolecules2218-273X2021-07-01117105310.3390/biom11071053Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i>Sara Kebbi0Maria Letizia Ciavatta1Ali Mokhtar Mahmoud2Marianna Carbone3Alessia Ligresti4Ramdane Seghiri5Margherita Gavagnin6Consiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34-80078 Pozzuoli, ItalyConsiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34-80078 Pozzuoli, ItalyConsiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34-80078 Pozzuoli, ItalyConsiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34-80078 Pozzuoli, ItalyConsiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34-80078 Pozzuoli, ItalyUnit of Valorization of Natural Resources, Bioactive Molecules and Physicochemical and Biological Analyzes (VARENBIOMOL), Department of Chemistry, Faculty of Exact Sciences, University of Mentouri Brothers Constantine 1, Constantine 25000, AlgeriaConsiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB), Via Campi Flegrei, 34-80078 Pozzuoli, ItalyIn continuing our investigation on the chemical diversity of Algerian plants, we examined <i>Centaurea omphalotricha</i>, whose chemical composition has been poorly studied. The present work was aimed at characterizing the secondary metabolite pattern of the CHCl<sub>3</sub> extract of the aerial parts of this plant that displayed antiproliferative properties in a preliminary screening on HeLa cell line. The chemical analysis led us to characterize the bioactive oxygenated terpenoid fraction which includes, within major known metabolites, two new minor sesquiterpene lactones, centaurolide-A (<b>1</b>) and centaurolide-B (<b>2</b>). The structures of two compounds exhibiting the 12,8-guaianolide skeleton were determined by spectroscopic methods as well as by chemical correlation with inuviscolide (<b>3</b>), a well-known bioactive guaianolide isolated from <i>Dittrichia</i> (=<i>Inula</i>) <i>viscosa</i>. Centaurolides A and B represent the first report of 8,12-guaianolide skeleton in <i>Centaurea</i> genus. The effect of new compounds <b>1</b> and <b>2</b> and inuviscolide (<b>3</b>) on HeLa cell has also been evaluated.https://www.mdpi.com/2218-273X/11/7/1053plant secondary metabolitessesquiterpene lactonesAsteraceaespectroscopic methods |
| spellingShingle | Sara Kebbi Maria Letizia Ciavatta Ali Mokhtar Mahmoud Marianna Carbone Alessia Ligresti Ramdane Seghiri Margherita Gavagnin Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i> Biomolecules plant secondary metabolites sesquiterpene lactones Asteraceae spectroscopic methods |
| title | Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i> |
| title_full | Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i> |
| title_fullStr | Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i> |
| title_full_unstemmed | Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i> |
| title_short | Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian <i>Centaurea omphalotricha</i> |
| title_sort | sesquiterpene lactones with the 12 8 guaianolide skeleton from algerian i centaurea omphalotricha i |
| topic | plant secondary metabolites sesquiterpene lactones Asteraceae spectroscopic methods |
| url | https://www.mdpi.com/2218-273X/11/7/1053 |
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