European Journal of Chemistry

Synthesis and antimicrobial activity of new ent-kaurene-type diterpenoid derivatives

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Published: Dec 31, 2023
DOI: https://doi.org/10.5155/eurjchem.14.4.478-485.2478
Keywords:
Diterpenes, Drug discovery, Antifungal agents, Antibacterial activity, ent-Kaurene derivatives, Structure-activity relationship
Section
Research Article
Issue
Vol. 14 No. 4 (2023): December 2023
Dates
Received 2023-09-16
Accepted 2023-10-20
Published 2023-12-31
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Andres Eduardo Marquez-Chacon
Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, 5101, Venezuela
https://orcid.org/0000-0002-8529-505X
Alida Perez Colmenares
Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, 5101, Venezuela
https://orcid.org/0000-0001-8910-4663
Luis Rojas Fermin
Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, 5101, Venezuela
https://orcid.org/0000-0003-4508-1927
Rosa Aparicio
Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, 5101, Venezuela
https://orcid.org/0000-0002-5020-0954
Freddy Alejandro Ramos
Department of Chemistry, Faculty of Science, National University of Colombia, Bogota, 111321, Colombia
https://orcid.org/0000-0002-9271-7193
Alfredo Usubillaga
Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, 5101, Venezuela
https://orcid.org/0000-0002-2913-5684
Ysbelia Obregon
Research Institute, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida, 5101, Venezuela
https://orcid.org/0000-0001-6152-6696

Abstract

This research consists in the synthesis of ent-kaurene-type diterpenoid derivatives from the new natural product ent-kaur-3-acetoxy-15-ene, to carry out structural modifications on the C3 carbon of the ent-kaurene core by introducing different oxygenated groups, especially esters, in order to probe the structure-activity relationship (SAR) against microorganisms. The structure of the compounds was confirmed by FT-IR, 1H NMR, 13C NMR, and GC-MS. The antimicrobial activity of the synthesized derivatives was evaluated, ent-kaur-3-O-(6’,7’-bibenzyl-oxy-caffeoyl)-15-ene (4) exhibited activity against all tested microorganisms: Staphylococcus aureus (16 mm), Enterococcus faecalis (12 mm), Escherichia coli (13 mm), Klebsiella pneumoniae (10 mm), Pseudomonas aeruginosa (8 mm) and Candida krusei (10 mm). These results reveal a remarkable structure-activity relationship over the C3 carbon of the ent-kaurene core, where the presence of oxygenated groups such as hydroxyl or alkyl esters enhances activity.


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Marquez-Chacon, A. E.; Colmenares, A. P.; Fermin, L. R.; Aparicio, R.; Ramos, F. A.; Usubillaga, A.; Obregon, Y. Synthesis and Antimicrobial Activity of New Ent-Kaurene-Type Diterpenoid Derivatives. Eur. J. Chem. 2023, 14, 478-485.

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