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

• Published in: Molecules (Basel, Switzerland) Vol. 29; no. 3; p. 650
• Main Authors: Ait El Had, Mustapha, Zefzoufi, Manal, Zentar, Houda, Bahsis, Lahoucine, Hachim, Mouhi Eddine, Ghaleb, Adib, Khelifa-Mahdjoubi, Choukri, Bouamama, Hafida, Alvarez-Manzaneda, Ramón, Justicia, José, Chahboun, Rachid
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 01-01-2024
• Subjects: abietane rearranged; ADMET; antibacterial activity; Antibiotics; Antimicrobial agents; Bacteria; Ciprofloxacin; Crystals; DFT calculation; Escherichia coli; Metabolites; natural product; Natural products; Oxidation; Phenols; prattinin A; Staphylococcus aureus; Staphylococcus infections; Structure; antibacterial activity; DFT calculation; prattinin A; molecular docking; abietane rearranged; natural product; ADMET
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules29030650

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:
,
, and
. The results showed that the antibacterial activity varies depending on the chemical structure of the compounds. Notably, compound
exhibited the most potent activity against
and
with a minimal inhibitory concentration (MIC) of 11.7 µg/mL, comparable to that of the standard antibiotic ciprofloxacin, and strong activity against
, 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
(pdb:1ESU) using molecular docking via UCSF Chimera software 1.17.3. The results suggest that
has potential as a natural antibiotic agent.