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Article

Evaluation of Anticancer and Anti-Inflammatory Activities of Some Synthetic Rearranged Abietanes

by
Mustapha Ait El Had
1,†,
Houda Zentar
1,2,†,
Blanca Ruiz-Muñoz
2,
Juan Sainz
2,3,
Juan J. Guardia
1,
Antonio Fernández
1,
José Justicia
1,
Enrique Alvarez-Manzaneda
1,
Fernando J. Reyes-Zurita
2,* and
Rachid Chahboun
1,*
1
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología, Universidad de Granada, 18071 Granada, Spain
2
Departamento de Bioquímica y Biología Molecular I, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
3
Centre for Genomics and Oncological Research: Pfizer, Genomic Oncology Area, GENYO, University of Granada, Andalusian Regional Government, PTS Granada, 18016 Granada, Spain
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Int. J. Mol. Sci. 2023, 24(17), 13583; https://doi.org/10.3390/ijms241713583
Submission received: 31 July 2023 / Revised: 26 August 2023 / Accepted: 30 August 2023 / Published: 1 September 2023
(This article belongs to the Special Issue Natural Product Chemistry and Biological Research)
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Abstract

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.
Keywords: rearranged abietane type; semisynthesis; antitumor activity; apoptosis; colorectal cancer; anti-inflammatory activity; nitric oxide rearranged abietane type; semisynthesis; antitumor activity; apoptosis; colorectal cancer; anti-inflammatory activity; nitric oxide

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MDPI and ACS Style

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

AMA Style

Ait El Had M, Zentar H, Ruiz-Muñoz B, Sainz J, Guardia JJ, Fernández A, Justicia J, Alvarez-Manzaneda E, Reyes-Zurita FJ, Chahboun R. Evaluation of Anticancer and Anti-Inflammatory Activities of Some Synthetic Rearranged Abietanes. International Journal of Molecular Sciences. 2023; 24(17):13583. https://doi.org/10.3390/ijms241713583

Chicago/Turabian Style

Ait El Had, Mustapha, Houda Zentar, Blanca Ruiz-Muñoz, Juan Sainz, Juan J. Guardia, Antonio Fernández, José Justicia, Enrique Alvarez-Manzaneda, Fernando J. Reyes-Zurita, and Rachid Chahboun. 2023. "Evaluation of Anticancer and Anti-Inflammatory Activities of Some Synthetic Rearranged Abietanes" International Journal of Molecular Sciences 24, no. 17: 13583. https://doi.org/10.3390/ijms241713583

APA Style

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. (2023). Evaluation of Anticancer and Anti-Inflammatory Activities of Some Synthetic Rearranged Abietanes. International Journal of Molecular Sciences, 24(17), 13583. https://doi.org/10.3390/ijms241713583

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