Synthesis and Biological Evaluation of Cassane Diterpene (5 alpha)-Vuacapane-8(14), 9(11)-Diene and of Some Related Compounds
| العنوان: | Synthesis and Biological Evaluation of Cassane Diterpene (5 alpha)-Vuacapane-8(14), 9(11)-Diene and of Some Related Compounds |
|---|---|
| المؤلفون: | Houda Zentar, Fatin Jannus, Marta Medina-O’Donnell, José A. Lupiáñez, José Justicia, Ramón Alvarez-Manzaneda, Fernando J. Reyes-Zurita, Enrique Alvarez-Manzaneda, Rachid Chahboun |
| المصدر: | Molecules; Volume 27; Issue 17; Pages: 5705 riUAL. Repositorio Institucional de la Universidad de Almería Universidad de Almería |
| بيانات النشر: | MDPI, 2022. |
| سنة النشر: | 2022 |
| مصطلحات موضوعية: | Caesalpinia, Molecular Structure, natural products, Organic Chemistry, Anti-Inflammatory Agents, Pharmaceutical Science, Antineoplastic Agents, Apoptosis, Polyenes, Nitric Oxide, Analytical Chemistry, cassane diterpenoids, Chemistry (miscellaneous), Cell Line, Tumor, Drug Discovery, anti-cancer activity, Molecular Medicine, semisynthesis, Humans, anti-inflammatory activity, Physical and Theoretical Chemistry, Diterpenes |
| الوصف: | 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 mu g/mL and 5.71 +/- 0.14 mu g/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 mu g/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. Junta de Andalucia BFQM-278-UGR20 B-FQM-650-UGR20 |
| وصف الملف: | application/pdf |
| اللغة: | English |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e9e0debd8f39e09894526a49ecccee0d https://hdl.handle.net/10481/77050 |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....e9e0debd8f39e09894526a49ecccee0d |
| قاعدة البيانات: | OpenAIRE |
| الوصف غير متاح. |