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

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: <i>E. coli</i>, <i>P. aeruginosa&...

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Bibliographic Details
Main Authors: Mustapha Ait El Had, Manal Zefzoufi, Houda Zentar, Lahoucine Bahsis, Mouhi Eddine Hachim, Adib Ghaleb, Choukri Khelifa-Mahdjoubi, Hafida Bouamama, Ramón Alvarez-Manzaneda, José Justicia, Rachid Chahboun
Format: Article
Language:English
Published: MDPI AG 2024-01-01
Series:Molecules
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Online Access:https://www.mdpi.com/1420-3049/29/3/650
Description
Summary: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: <i>E. coli</i>, <i>P. aeruginosa</i>, and <i>S. aureus</i>. The results showed that the antibacterial activity varies depending on the chemical structure of the compounds. Notably, compound <b>27</b> exhibited the most potent activity against <i>E. coli</i> and <i>P. aeruginosa,</i> with a minimal inhibitory concentration (MIC) of 11.7 µg/mL, comparable to that of the standard antibiotic ciprofloxacin, and strong activity against <i>S. aureus</i>, 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 <i>E. coli</i> (pdb:1ESU) using molecular docking via UCSF Chimera software 1.17.3. The results suggest that <b>27</b> has potential as a natural antibiotic agent.
ISSN:1420-3049