Evaluation of Anticancer and Anti-Inflammatory Activities of Some Synthetic Rearranged Abietanes Ait El Had, Mustapha Zentar, Houda Ruiz-Muñoz, Blanca Sáinz Pérez, Juan Guardia Monteagudo, Juan José Fernández Vargas, Antonio Jesús Justicia Ladrón De Guevara, José Álvarez De Manzaneda Roldán, Enrique Reyes Zurita, Fernando Jesús Chahboun Karimi, Rachid Rearranged abietane type Semisynthesis Antitumor activity Apoptosis Colorectal cancer Anti-inflammatory activity Nitric oxide This research was funded by grants from the Regional Government of Andalusia (Projects B-FQM-278-UGR20, and B-FQM-650-UGR-20), and assistance was provided to the group FQM-348. Supplementary Materials: The following supporting information can be downloaded at https://www.mdpi.com/article/10.3390/ijms241713583/s1 Synthesis of the rearranged abietane diterpenes pygmaeocins C and D, viridoquinone, saprorthoquinone, and 1-deoxyviroxocine has been successfully achieved. The anticancer and anti-inflammatory activities of selected orthoquinonic compounds 5, 7, 13, and 19, as well as pygmaeocin C (17), were evaluated for the first time. The antitumor properties were assessed using three cancer cell lines: HT29 colon cancer cells, Hep G2 hepatocellular carcinoma cells, and B16-F10 murine melanoma cells. Compounds 5 and 13 showed the highest cytotoxicity in HT29 cells (IC50 = 6.69 ± 1.2 µg/mL and IC50 = 2.7 ± 0.8 µg/mL, respectively). Cytometric studies showed that this growth inhibition involved phase S cell cycle arrest and apoptosis induction, possibly through the activation of the intrinsic apoptotic pathway. Morphological apoptotic changes, including nuclear fragmentation and chromatin condensation, were also observed. Furthermore, the anti-inflammatory activity of these compounds was evaluated on the basis of their ability to inhibit nitric oxide production on the lipopolysaccharide activated RAW 264.7 macrophage cell line. Although all compounds showed high anti-inflammatory activity, with percentages between 40 and 100%, the highest anti-inflammatory potential was obtained by pygmaeocin B (5) (IC50NO = 33.0 ± 0.8 ng/mL). Our results suggest that due to their dual roles, this type of compound could represent a new strategy, contributing to the development of novel anticancer agents. 2023-10-11T12:14:48Z 2023-10-11T12:14:48Z 2023-09-01 journal article Ait El Had, M.; Zentar, H.; Ruiz-Muñoz, B.; Sainz, J.; Guardia, J.J.; Fernández, A.; Justicia, J.; Alvarez-Manzaneda, E.; Reyes-Zurita, F.J.; Chahboun, R. Evaluation of Anticancer and Anti-Inflammatory Activities of Some Synthetic Rearranged Abietanes. Int. J. Mol. Sci. 2023, 24, 13583. [https://doi.org/10.3390/ijms241713583] https://hdl.handle.net/10481/84948 10.3390/ijms241713583 eng http://creativecommons.org/licenses/by/4.0/ open access Atribución 4.0 Internacional MDPI