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Molecular Docking, Physicochemical Properties, Pharmacokinetics and Toxicity of Flavonoids Present in Euterpe oleracea Martius.
Curr Comput Aided Drug Des. 2021; 17(4):589-617.CC

Abstract

BACKGROUND

Euterpe oleracea Martius, popularly known as açaí, is a fruit rich in α- tocopherols, fibers, lipids, mineral ions, and polyphenols. It is believed that the high content of polyphenols, especially flavonoids, provides several health-promoting effects to the açaí fruit, including anti-inflammatory, immunomodulatory, antinociceptive and antioxidant properties. Most of the flavonoids are antioxidant molecules of plant origin that act as a trap for free radicals, reacting and neutralizing them, thus offering perspectives in preventing oxidative damage.

OBJECTIVE

In this study, we aim to perform an in silico evaluation of flavonoids present in the pulp and the oil of Euterpe oleracea Martius, evaluating their potential to serve as antioxidant agents.

METHODS

Firstly, we selected 16 flavonoids present in Euterpe oleracea Martius pulp and oil, and then their physicochemical properties were analyzed concerning the Lipinski's Rule of Five. Moreover, we evaluated their pharmacokinetic properties using the QikProp module of the Schrödinger software as well as their toxicity profile, using the DEREK software. Docking simulations, using the GOLD 4.1 software, as well as pharmacophoric hypotheses calculation of molecules were also performed.

RESULTS

Flavonoids present in the açaí pulp including catechin, epicatechin, luteolin, chrisoeriol, taxifolin, apigenin, dihydrokaempferol, isovitexin, and vitexin presented good oral bioavailability. Regarding the pharmacokinetic properties, the compounds catechin, epicatechin, isovitexin, luteolin, chrisoeriol, taxifolin, and isorhamnetin rutinoside presented the best results, besides high human oral absorption. Regarding the prediction of toxicological properties, compounds isorhamnetin rutinoside and rutin presented mutagenicity for hydroxynaphthalene or derivate, and regarding the docking simulations, all the compounds investigated in this study presented key interactions with the corresponding targets.

CONCLUSION

The flavonoids catechin, chrysoeriol, and taxifolin presented the best results according to the evaluation conducted in this study. These computational results can be used as a theoretical basis for future studies concerning the development of drug candidates, as well as to enlighten biological tests in vitro and in vivo, which can contribute to the treatment of neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease, and Huntington's disease.

Authors+Show Affiliations

Laboratory of Pharmaceutical and Medicinal Chemistry (PharMedChem), Federal University of Amapa, Macapa, Amapa, Brazil.Laboratory of Pharmaceutical and Medicinal Chemistry (PharMedChem), Federal University of Amapa, Macapa, Amapa, Brazil.Laboratory of Pharmaceutical and Medicinal Chemistry (PharMedChem), Federal University of Amapa, Macapa, Amapa, Brazil.Computational Laboratory of Pharmaceutical Chemistry, School of Pharmaceutical Sciences of Ribeirao Preto, University of Sao Paulo, Ribeirao Preto, Sao Paulo, Brazil.Computational Laboratory of Pharmaceutical Chemistry, School of Pharmaceutical Sciences of Ribeirao Preto, University of Sao Paulo, Ribeirao Preto, Sao Paulo, Brazil.Computational Laboratory of Pharmaceutical Chemistry, School of Pharmaceutical Sciences of Ribeirao Preto, University of Sao Paulo, Ribeirao Preto, Sao Paulo, Brazil.Laboratory of Phytopharmaceutical Nanobiotechnology, Federal University of Amapa, Macapa, Amapa, Brazil.Laboratory of Pharmaceutical and Medicinal Chemistry (PharMedChem), Federal University of Amapa, Macapa, Amapa, Brazil.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32560610

Citation

de Oliveira, Nayana Keyla Seabra, et al. "Molecular Docking, Physicochemical Properties, Pharmacokinetics and Toxicity of Flavonoids Present in Euterpe Oleracea Martius." Current Computer-aided Drug Design, vol. 17, no. 4, 2021, pp. 589-617.
de Oliveira NKS, Almeida MRS, Pontes FMM, et al. Molecular Docking, Physicochemical Properties, Pharmacokinetics and Toxicity of Flavonoids Present in Euterpe oleracea Martius. Curr Comput Aided Drug Des. 2021;17(4):589-617.
de Oliveira, N. K. S., Almeida, M. R. S., Pontes, F. M. M., Barcelos, M. P., Silva, G. M., de Paula da Silva, C. H. T., Cruz, R. A. S., & da Silva Hage-Melim, L. I. (2021). Molecular Docking, Physicochemical Properties, Pharmacokinetics and Toxicity of Flavonoids Present in Euterpe oleracea Martius. Current Computer-aided Drug Design, 17(4), 589-617. https://doi.org/10.2174/1573409916666200619122803
de Oliveira NKS, et al. Molecular Docking, Physicochemical Properties, Pharmacokinetics and Toxicity of Flavonoids Present in Euterpe Oleracea Martius. Curr Comput Aided Drug Des. 2021;17(4):589-617. PubMed PMID: 32560610.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Molecular Docking, Physicochemical Properties, Pharmacokinetics and Toxicity of Flavonoids Present in Euterpe oleracea Martius. AU - de Oliveira,Nayana Keyla Seabra, AU - Almeida,Marcos Rafael Silva, AU - Pontes,Franco Márcio Maciel, AU - Barcelos,Mariana Pegrucci, AU - Silva,Guilherme Martins, AU - de Paula da Silva,Carlos Henrique Tomich, AU - Cruz,Rodrigo Alves Soares, AU - da Silva Hage-Melim,Lorane Izabel, PY - 2020/02/08/received PY - 2020/04/13/revised PY - 2020/05/02/accepted PY - 2020/6/21/pubmed PY - 2022/1/14/medline PY - 2020/6/21/entrez KW - Euterpe oleracea Martius KW - Flavonoids KW - Huntington's disease KW - Parkinson's disease. KW - Parkinson's disease.Flavonoids KW - antioxidants KW - açaí SP - 589 EP - 617 JF - Current computer-aided drug design JO - Curr Comput Aided Drug Des VL - 17 IS - 4 N2 - BACKGROUND: Euterpe oleracea Martius, popularly known as açaí, is a fruit rich in α- tocopherols, fibers, lipids, mineral ions, and polyphenols. It is believed that the high content of polyphenols, especially flavonoids, provides several health-promoting effects to the açaí fruit, including anti-inflammatory, immunomodulatory, antinociceptive and antioxidant properties. Most of the flavonoids are antioxidant molecules of plant origin that act as a trap for free radicals, reacting and neutralizing them, thus offering perspectives in preventing oxidative damage. OBJECTIVE: In this study, we aim to perform an in silico evaluation of flavonoids present in the pulp and the oil of Euterpe oleracea Martius, evaluating their potential to serve as antioxidant agents. METHODS: Firstly, we selected 16 flavonoids present in Euterpe oleracea Martius pulp and oil, and then their physicochemical properties were analyzed concerning the Lipinski's Rule of Five. Moreover, we evaluated their pharmacokinetic properties using the QikProp module of the Schrödinger software as well as their toxicity profile, using the DEREK software. Docking simulations, using the GOLD 4.1 software, as well as pharmacophoric hypotheses calculation of molecules were also performed. RESULTS: Flavonoids present in the açaí pulp including catechin, epicatechin, luteolin, chrisoeriol, taxifolin, apigenin, dihydrokaempferol, isovitexin, and vitexin presented good oral bioavailability. Regarding the pharmacokinetic properties, the compounds catechin, epicatechin, isovitexin, luteolin, chrisoeriol, taxifolin, and isorhamnetin rutinoside presented the best results, besides high human oral absorption. Regarding the prediction of toxicological properties, compounds isorhamnetin rutinoside and rutin presented mutagenicity for hydroxynaphthalene or derivate, and regarding the docking simulations, all the compounds investigated in this study presented key interactions with the corresponding targets. CONCLUSION: The flavonoids catechin, chrysoeriol, and taxifolin presented the best results according to the evaluation conducted in this study. These computational results can be used as a theoretical basis for future studies concerning the development of drug candidates, as well as to enlighten biological tests in vitro and in vivo, which can contribute to the treatment of neurodegenerative diseases, such as Alzheimer's disease, Parkinson's disease, and Huntington's disease. SN - 1875-6697 UR - https://www.unboundmedicine.com/medline/citation/32560610/Molecular_Docking_Physicochemical_Properties_Pharmacokinetics_and_Toxicity_of_Flavonoids_Present_in_Euterpe_oleracea_Martius_ L2 - https://www.eurekaselect.com/182936/article DB - PRIME DP - Unbound Medicine ER -