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&...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-01-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/29/3/650 |
| _version_ | 1827354638791213056 |
|---|---|
| author | 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 |
| author_facet | 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 |
| author_sort | Mustapha Ait El Had |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-08T03:51:35Z |
| format | Article |
| id | doaj.art-40a42250261147a191fa95fc9a86b1fe |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T03:51:35Z |
| publishDate | 2024-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-40a42250261147a191fa95fc9a86b1fe2024-02-09T15:18:58ZengMDPI AGMolecules1420-30492024-01-0129365010.3390/molecules29030650Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic DerivativesMustapha Ait El Had0Manal Zefzoufi1Houda Zentar2Lahoucine Bahsis3Mouhi Eddine Hachim4Adib Ghaleb5Choukri Khelifa-Mahdjoubi6Hafida Bouamama7Ramón Alvarez-Manzaneda8José Justicia9Rachid Chahboun10Departamento de Química Organica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, SpainRecherche en Développement Durable et Santé, Faculté des Sciences et Techniques, Cadi Ayyad University, Marrakech 40000, MoroccoDepartamento de Química Organica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, SpainLaboratory of Analytical and Molecular Chemistry, Polydisciplinary Faculty, Cadi Ayyad University, BP 4162, Safi 46000, MoroccoLaboratory of Analytical and Molecular Chemistry, Polydisciplinary Faculty, Cadi Ayyad University, BP 4162, Safi 46000, MoroccoLaboratory of Analytical and Molecular Chemistry, Polydisciplinary Faculty, Cadi Ayyad University, BP 4162, Safi 46000, MoroccoDepartamento de Química Organica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, SpainRecherche en Développement Durable et Santé, Faculté des Sciences et Techniques, Cadi Ayyad University, Marrakech 40000, MoroccoÁrea de Química Orgánica, Departamento de Química y Física, Universidad de Almería, 04120 Almería, SpainDepartamento de Química Organica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, SpainDepartamento de Química Organica, Facultad de Ciencias, Universidad de Granada, 18071 Granada, SpainSynthesis 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.https://www.mdpi.com/1420-3049/29/3/650natural productabietane rearrangedprattinin Aantibacterial activityADMETDFT calculation |
| spellingShingle | 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 Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives Molecules natural product abietane rearranged prattinin A antibacterial activity ADMET DFT calculation |
| title | Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives |
| title_full | Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives |
| title_fullStr | Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives |
| title_full_unstemmed | Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives |
| title_short | Synthesis and Evaluation of Antimicrobial Activity of the Rearranged Abietane Prattinin A and Its Synthetic Derivatives |
| title_sort | synthesis and evaluation of antimicrobial activity of the rearranged abietane prattinin a and its synthetic derivatives |
| topic | natural product abietane rearranged prattinin A antibacterial activity ADMET DFT calculation |
| url | https://www.mdpi.com/1420-3049/29/3/650 |
| work_keys_str_mv | AT mustaphaaitelhad synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT manalzefzoufi synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT houdazentar synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT lahoucinebahsis synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT mouhieddinehachim synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT adibghaleb synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT choukrikhelifamahdjoubi synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT hafidabouamama synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT ramonalvarezmanzaneda synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT josejusticia synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives AT rachidchahboun synthesisandevaluationofantimicrobialactivityoftherearrangedabietaneprattininaanditssyntheticderivatives |