Molecular modelling and anticholinesterase activity of the essential oil from three chemotypes of Lippia alba (Mill.) N.E.Br. ex Britton & P. Wilson (Verbenaceae)
Antônio Quaresma Silva Júnior,
Gabriela dos Santos Rodrigues,
Karina Alcântara de Sousa,
Leoneide Erica Maduro Bouillet,
Gabriela Bianchi dos Santos,
Adenilson de Sousa Barroso,
Rosa Helena Veras Mourão
Affiliations
Antônio Quaresma Silva Júnior
Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil; Programa de Pós-Graduação em Biodiversidade e Biotecnologia da Rede Bionorte, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil
Gabriela dos Santos Rodrigues
Programa de Pós-Graduação em Ciências da Saúde, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil
Karina Alcântara de Sousa
Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil; Programa de Pós-Graduação em Ciências da Saúde, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil
Leoneide Erica Maduro Bouillet
Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil; Programa de Pós-Graduação em Ciências da Saúde, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil
Gabriela Bianchi dos Santos
Programa de Pós-Graduação em Ciências da Saúde, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil
Adenilson de Sousa Barroso
Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil
Rosa Helena Veras Mourão
Laboratório de Bioprospecção e Biologia Experimental, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil; Programa de Pós-Graduação em Biodiversidade e Biotecnologia da Rede Bionorte, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil; Programa de Pós-Graduação em Ciências da Saúde, Universidade Federal do Oeste do Pará, Santarém, PA, Brazil; Corresponding author. UFOPA - Campus Tapajós, Endereço Postal: R. Vera Paz - Salé, Santarém, PA, 68040-255, Brazil.
Lippia alba (Mill.) N.E. Brown (Verbenaceae), popularly known as “erva cidreira”, is one of the most used plants in Brazilian folk medicine. The species has several chemotypes and its volatile constituents have already been characterized, and present different chemical markers with known pharmacological properties, such as analgesic, sedative and antifungal properties. The objective of this study was to evaluate the anticholinesterase activity (AChE) of the essential oil of three chemotypes of Lippia alba and, by using molecular anchoring, determine the best receptor-ligand interaction energies of the main constituents present in the samples of oil. The essential oils were obtained via hydrodistillation (LA1 and LA2) and steam drag (LA3), and their volatile constituents determined using GC-MS. For the determination of anticholinesterase activity, direct bioautography and colorimetry assays based on Ellman's method were used. Molecular docking was performed using a multiple solution genetic algorithm and Merck molecular force field 94 (MMFF94) as the scoring function. In the main constituents of the oil samples, three chemotypes were identified for L. alba: LA1 is rich in citral, LA2 is rich in carvone and LA3 is rich in linalool. All L. alba chemotypes showed AChE enzyme inhibition with an IC50 of 3.57 μg/mL (LA1), 0.1 μg/mL (LA2) and 4.34 μg/mL (LA3). The molecular docking study complemented the results of the experiment and demonstrated significant interactions between the main constituents of the oils and the amino acid residues of the AChE enzyme. Irrespective of the chemotype, Lippia alba presents biotechnological potential for the discovery of anticholinesterase substances, with the chemotype LA2 (rich in carvone) being the most active.
