New insights into structural, electronic, reactivity, spectroscopic and pharmacological properties of Bergenin: Experimental, DFT calculations, MD and docking simulations

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dc.contributor.authorCosta, Renyer A.
dc.contributor.authorda Silva, Jonathas N. [UNESP]
dc.contributor.authorOliveira, Viviane G.
dc.contributor.authorAnselmo, Lucas M.
dc.contributor.authorAraújo, Míriam M.
dc.contributor.authorOliveira, Kelson M.T.
dc.contributor.authorNunomura, Rita de Cássia S.
dc.contributor.institutionFederal University of Amazonas (DQ-UFAM)
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionVale do Rio Madeira Campus Federal University of Amazonas
dc.date.accessioned2021-06-25T10:23:44Z
dc.date.available2021-06-25T10:23:44Z
dc.date.issued2021-05-15
dc.description.abstractBergenin is a polyphenol found in many medicinal plants that presents numerous activities, such as antiulcer, anti-inflammatory, antifungal, anticancer, antimicrobial, antidiabetic, antiviral and antioxidant, being, therefore, a research target nowadays. In the present study, bergenin, isolated from Endopleura uchi Huber Cuatrecasas plant, was studied through density functional theory (DFT) and time-dependent density functional theory (TD-DFT), at the B3LYP/6–311++G(2d,2p) and B3LYP-D3(BJ)/6–311+G(2d,p) levels, where the obtained optimized geometry, FT-IR and UV–Vis data were analyzed along with experimental data. The comparative IR studies, together with potential energy distribution (PED) calculation, enabled the assignment of the observed experimental IR bands, besides evaluating the existence of intermolecular H-bonds through dimers formation. The calculated electronic transitions are in good agreement with the experimental data, which allowed the characterization of the UV–Vis bands. HOMO-LUMO energy gaps, average local ionization energy (ALIE) surfaces and Fukui indices calculations were carried out, allowing to concisely evaluate the reactive sites of bergenin. Also, calculations of solvation free energies and free energies of association in water, methanol and ethanol were performed. Due to the know in vitro anti-inflammatory and anticancer activities presented by bergenin, molecular docking and molecular dynamic (MD) calculations were carried out in front of cyclooxygenases 1 and 2 and topoisomerases I and II, revealing good interactions of bergenin with the active site of the tested enzymes, justifying the experimental results found in literature.en
dc.description.affiliationDepartment of Chemistry Federal University of Amazonas (DQ-UFAM)
dc.description.affiliationFaculty of Sciences and Letters São Paulo State University (UNESP), Araraquara Campus
dc.description.affiliationInstitute of Education Agriculture and Environment Vale do Rio Madeira Campus Federal University of Amazonas
dc.description.affiliationUnespFaculty of Sciences and Letters São Paulo State University (UNESP), Araraquara Campus
dc.description.sponsorshipCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.description.sponsorshipConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.description.sponsorshipFinanciadora de Estudos e Projetos
dc.description.sponsorshipUniversidade Federal de Juiz de Fora
dc.identifierhttp://dx.doi.org/10.1016/j.molliq.2021.115625
dc.identifier.citationJournal of Molecular Liquids, v. 330.
dc.identifier.doi10.1016/j.molliq.2021.115625
dc.identifier.issn0167-7322
dc.identifier.scopus2-s2.0-85101250241
dc.identifier.urihttp://hdl.handle.net/11449/205926
dc.language.isoeng
dc.relation.ispartofJournal of Molecular Liquids
dc.sourceScopus
dc.subjectBergenin
dc.subjectCOX 1 and 2
dc.subjectDFT
dc.subjectMolecular docking
dc.subjectMolecular dynamics
dc.subjectTopoisomerase I and II
dc.titleNew insights into structural, electronic, reactivity, spectroscopic and pharmacological properties of Bergenin: Experimental, DFT calculations, MD and docking simulationsen
dc.typeArtigo

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