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Synthesis and Biological Evaluation of Cassane Diterpene (5α)-Vuacapane-8(14), 9(11)-Diene and of Some Related Compounds
dc.contributor.author | Zentar, Houda | |
dc.contributor.author | Jannus, Fatin | |
dc.contributor.author | Medina-O’Donnell, Marta | |
dc.contributor.author | Lupiáñez, José A. | |
dc.contributor.author | Justicia, José | |
dc.contributor.author | Alvarez-Manzaneda Roldán, Ramón Jesús | |
dc.contributor.author | Reyes-Zurita, Fernando J. | |
dc.contributor.author | Alvarez-Manzaneda, Enrique | |
dc.contributor.author | Chahboun, Rachid | |
dc.date.accessioned | 2022-09-07T16:38:13Z | |
dc.date.available | 2022-09-07T16:38:13Z | |
dc.date.issued | 2022-09-04 | |
dc.identifier.issn | 1420-3049 | |
dc.identifier.uri | http://hdl.handle.net/10835/13934 | |
dc.description.abstract | A set of thirteen cassane-type diterpenes was synthesized and an expedient synthetic route was used to evaluate 14-desmethyl analogs of the most active tested cassane. The anti-inflammatory activities of these 13 compounds were evaluated on a lipopolysaccharide (LPS)-activated RAW 264.7 cell line by inhibition of nitric oxide (NO) production, some of them reaching 100% NO inhibition after 72 h of treatment. The greatest anti-inflammatory effect was observed for compounds 16 and 20 with an IC50 NO of 2.98 ± 0.04 μg/mL and 5.71 ± 0.14 μg/mL, respectively. Flow-cytometry analysis was used to determine the cell cycle distribution and showed that the inhibition in NO release was accompanied by a reversion of the differentiation processes. Moreover, the anti-cancer potential of these 13 compounds were evaluated in three tumor cell lines (B16-F10, HT29, and Hep G2). The strongest cytotoxic effect was achieved by salicylaldehyde 20, and pterolobirin G (6), with IC50 values around 3 μg/mL in HT29 cells, with total apoptosis rates 80% at IC80 concentrations, producing a significant cell-cycle arrest in the G0/G1 phase, and a possible activation of the extrinsic apoptotic pathway. Additionally, initial SAR data analysis showed that the methyl group at the C-14 positions of cassane diterpenoids is not always important for their cytotoxic and anti-inflammatory activities. | es_ES |
dc.language.iso | en | es_ES |
dc.publisher | MDPI | es_ES |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | natural products | es_ES |
dc.subject | semisynthesis | es_ES |
dc.subject | cassane diterpenoids | es_ES |
dc.subject | anti-inflammatory activity | es_ES |
dc.subject | anti-cancer activity | es_ES |
dc.title | Synthesis and Biological Evaluation of Cassane Diterpene (5α)-Vuacapane-8(14), 9(11)-Diene and of Some Related Compounds | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.relation.publisherversion | https://www.mdpi.com/1420-3049/27/17/5705 | es_ES |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es_ES |
dc.identifier.doi | 10.3390/molecules27175705 |