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Article

Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives

by
Mustapha Ait El Had
1,2,
Manal Zefzoufi
3,
Houda Zentar
1,
Lahoucine Bahsis
4,
Mouhi Eddine Hachim
4,
Adib Ghaleb
4,
Choukri Khelifa-Mahdjoubi
1,
Hafida Bouamama
3,
Ramón Alvarez-Manzaneda
5,
José Justicia
1,* and
Rachid Chahboun
1,*
1
Departamento de Química Organica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
2
Département des Sciences Fondamentales, Faculté de Médecine et de Pharmacie, et de Médecine Dentaire de Fès, Université Sidi Mohamed Ben Abdellah de Fès, Fes 30000, Morocco
3
Recherche en Développement Durable et Santé, Faculté des Sciences et Techniques, Cadi Ayyad University, Marrakech 40000, Morocco
4
Laboratory of Analytical and Molecular Chemistry, Polydisciplinary Faculty, Cadi Ayyad University, BP 4162, Safi 46000, Morocco
5
Área de Química Orgánica, Departamento de Química y Física, Universidad de Almería, 04120 Almería, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(3), 650; https://doi.org/10.3390/molecules29030650
Submission received: 1 January 2024 / Revised: 23 January 2024 / Accepted: 26 January 2024 / Published: 30 January 2024
(This article belongs to the Special Issue Antibacterial, Antifungal, and Antiviral Bioactive Compounds from Natural Products, 2nd Edition)
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Abstract

Synthesis of the natural product prattinin A and some new derivatives has been achieved using abietic acid. The final products and a selection of intermediates were evaluated for their antibacterial activity against three human pathogenic bacteria: E. coli, P. aeruginosa, and S. aureus. The results showed that the antibacterial activity varies depending on the chemical structure of the compounds. Notably, compound 27 exhibited the most potent activity against E. coli and P. aeruginosa, with a minimal inhibitory concentration (MIC) of 11.7 µg/mL, comparable to that of the standard antibiotic ciprofloxacin, and strong activity against S. aureus, with an MIC of 23.4 µg/mL. Furthermore, we assessed the stability of these derivative compounds as potential antimicrobial agents and determined their interactions with the crystal structure of the protein receptor mutant TEM-12 from E. coli (pdb:1ESU) using molecular docking via UCSF Chimera software 1.17.3. The results suggest that 27 has potential as a natural antibiotic agent.
Keywords: natural product; abietane rearranged; prattinin A; antibacterial activity; ADMET; DFT calculation; molecular docking natural product; abietane rearranged; prattinin A; antibacterial activity; ADMET; DFT calculation; molecular docking

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MDPI and ACS Style

Ait El Had, M.; Zefzoufi, M.; Zentar, H.; Bahsis, L.; Hachim, M.E.; Ghaleb, A.; Khelifa-Mahdjoubi, C.; Bouamama, H.; Alvarez-Manzaneda, R.; Justicia, J.; et al. Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives. Molecules 2024, 29, 650. https://doi.org/10.3390/molecules29030650

AMA Style

Ait El Had M, Zefzoufi M, Zentar H, Bahsis L, Hachim ME, Ghaleb A, Khelifa-Mahdjoubi C, Bouamama H, Alvarez-Manzaneda R, Justicia J, et al. Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives. Molecules. 2024; 29(3):650. https://doi.org/10.3390/molecules29030650

Chicago/Turabian Style

Ait El Had, Mustapha, Manal Zefzoufi, Houda Zentar, Lahoucine Bahsis, Mouhi Eddine Hachim, Adib Ghaleb, Choukri Khelifa-Mahdjoubi, Hafida Bouamama, Ramón Alvarez-Manzaneda, José Justicia, and et al. 2024. "Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives" Molecules 29, no. 3: 650. https://doi.org/10.3390/molecules29030650

APA Style

Ait El Had, M., Zefzoufi, M., Zentar, H., Bahsis, L., Hachim, M. E., Ghaleb, A., Khelifa-Mahdjoubi, C., Bouamama, H., Alvarez-Manzaneda, R., Justicia, J., & Chahboun, R. (2024). Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives. Molecules, 29(3), 650. https://doi.org/10.3390/molecules29030650

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