Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule
4-Nerolidylcatechol (4NRC), a secondary metabolite described as a potent antioxidant that presents anti-inflammatory, antimalarial, analgesic, and cytotoxic properties, has been receiving prominence in the catechol class. In this work, a theoretical DFT study of the vibrational, structural, and quan...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/9627404 |
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| author | Renyer A. Costa Earle Silva A. Junior Jaqueline de A. Bezerra Josiana Moreira Mar Emerson S. Lima Maria Lucia B. Pinheiro Diego V. C. Mendonça Guilherme Braule P. Lopes Adjane Dalvana S. Branches Kelson M. T. Oliveira |
| author_facet | Renyer A. Costa Earle Silva A. Junior Jaqueline de A. Bezerra Josiana Moreira Mar Emerson S. Lima Maria Lucia B. Pinheiro Diego V. C. Mendonça Guilherme Braule P. Lopes Adjane Dalvana S. Branches Kelson M. T. Oliveira |
| author_sort | Renyer A. Costa |
| collection | DOAJ |
| description | 4-Nerolidylcatechol (4NRC), a secondary metabolite described as a potent antioxidant that presents anti-inflammatory, antimalarial, analgesic, and cytotoxic properties, has been receiving prominence in the catechol class. In this work, a theoretical DFT study of the vibrational, structural, and quantum properties of 4-nerolidylcatechol (4NRC) using the B3LYP/6-311G (2d,p) level is presented. The theoretical molecular geometry data were compared with the X-ray data of a similar molecule in the associated literature and a conformational study is presented, with the aim of providing a good comprehension of the 4NRC structural arrangement and stability. Also, HOMO-LUMO energy gap and natural bond orbitals (NBOs) were performed and discussed. The calculated UV spectrum showed similarity to the experimentally obtained data, with transitions assigned. The comparative IR studies revealed that intermolecular hydrogen bonds that stabilize dimeric forms are plausible and also allowed the assignment of several characteristic vibrations. Molecular docking calculations with DNA topoisomerase I-DNA complex (TOPO-I), glyceraldehyde 3-phospate dehydrogenase (GAPDH), and Plasmodium falciparum lactate dehydrogenase (PfLDH) showed binding free energies of −6.3, −6.5, and −7.6 kcal/mol, respectively, which indicates that 4NRC is a good competitive inhibitor for these enzymes. |
| format | Article |
| id | doaj-art-6f876bc11a504d2ca7a62272b3abab72 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-6f876bc11a504d2ca7a62272b3abab722025-02-03T06:11:53ZengWileyJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/96274049627404Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive MoleculeRenyer A. Costa0Earle Silva A. Junior1Jaqueline de A. Bezerra2Josiana Moreira Mar3Emerson S. Lima4Maria Lucia B. Pinheiro5Diego V. C. Mendonça6Guilherme Braule P. Lopes7Adjane Dalvana S. Branches8Kelson M. T. Oliveira9Department of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, BrazilFederal Institute of Science and Technology of Amazonas (IFAM), 69020-120 Manaus, AM, BrazilFederal Institute of Science and Technology of Amazonas (IFAM), 69020-120 Manaus, AM, BrazilDepartment of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, BrazilFaculty of Pharmaceutical Sciences, Federal University of Amazonas, 69077-000 Manaus, AM, BrazilDepartment of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, BrazilDepartment of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, BrazilDepartment of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, BrazilDepartment of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, BrazilDepartment of Chemistry, Federal University of Amazonas (DQ-UFAM), 69077-000 Manaus, AM, Brazil4-Nerolidylcatechol (4NRC), a secondary metabolite described as a potent antioxidant that presents anti-inflammatory, antimalarial, analgesic, and cytotoxic properties, has been receiving prominence in the catechol class. In this work, a theoretical DFT study of the vibrational, structural, and quantum properties of 4-nerolidylcatechol (4NRC) using the B3LYP/6-311G (2d,p) level is presented. The theoretical molecular geometry data were compared with the X-ray data of a similar molecule in the associated literature and a conformational study is presented, with the aim of providing a good comprehension of the 4NRC structural arrangement and stability. Also, HOMO-LUMO energy gap and natural bond orbitals (NBOs) were performed and discussed. The calculated UV spectrum showed similarity to the experimentally obtained data, with transitions assigned. The comparative IR studies revealed that intermolecular hydrogen bonds that stabilize dimeric forms are plausible and also allowed the assignment of several characteristic vibrations. Molecular docking calculations with DNA topoisomerase I-DNA complex (TOPO-I), glyceraldehyde 3-phospate dehydrogenase (GAPDH), and Plasmodium falciparum lactate dehydrogenase (PfLDH) showed binding free energies of −6.3, −6.5, and −7.6 kcal/mol, respectively, which indicates that 4NRC is a good competitive inhibitor for these enzymes.http://dx.doi.org/10.1155/2019/9627404 |
| spellingShingle | Renyer A. Costa Earle Silva A. Junior Jaqueline de A. Bezerra Josiana Moreira Mar Emerson S. Lima Maria Lucia B. Pinheiro Diego V. C. Mendonça Guilherme Braule P. Lopes Adjane Dalvana S. Branches Kelson M. T. Oliveira Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule Journal of Chemistry |
| title | Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule |
| title_full | Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule |
| title_fullStr | Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule |
| title_full_unstemmed | Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule |
| title_short | Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule |
| title_sort | theoretical investigation of the structural spectroscopic electronic and pharmacological properties of 4 nerolidylcathecol an important bioactive molecule |
| url | http://dx.doi.org/10.1155/2019/9627404 |
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