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A computational investigation on the antioxidant potential of myricetin 3,4'-di-O-α-L-rhamnopyranoside.
Mendes, Rodrigo A; Almeida, Shawan K C; Soares, Iuri N; Barboza, Cristina A; Freitas, Renato G; Brown, Alex; de Souza, Gabriel L C.
Afiliação
  • Mendes RA; Departamento de Química, Universidade Federal de Mato Grosso, Cuiabá, Mato Grosso, 78060-900, Brazil.
  • Almeida SKC; Departamento de Química, Universidade Federal de Mato Grosso, Cuiabá, Mato Grosso, 78060-900, Brazil.
  • Soares IN; Departamento de Química, Universidade Federal de Mato Grosso, Cuiabá, Mato Grosso, 78060-900, Brazil.
  • Barboza CA; Institute of Physics, Polish Academy of Sciences, aleja Lotników 32/46, 02 668, Warsaw, Poland.
  • Freitas RG; Departamento de Química, Universidade Federal de Mato Grosso, Cuiabá, Mato Grosso, 78060-900, Brazil.
  • Brown A; Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada.
  • de Souza GLC; Departamento de Química, Universidade Federal de Mato Grosso, Cuiabá, Mato Grosso, 78060-900, Brazil. gabriellcs@pq.cnpq.br.
J Mol Model ; 24(6): 133, 2018 May 11.
Article em En | MEDLINE | ID: mdl-29752542
In this work, we present a computational study on the antioxidant potential of myricetin 3,4[Formula: see text]-di-O-α-L-rhamnopyranoside (Compound M). A density functional theory (DFT) approach with the B3LYP and LC-ωPBE functionals and with both the 6-311G(d,p) and 6-311+G(d,p) basis sets was used. The focus of the investigation was on the structural and energetic parameters including both bond dissociation enthalpies (BDEs) and ionization potentials (IPs), which provide information on the potential antioxidant activity. The properties computed were compared with BDEs and IPs available in the literature for myricetin, a compound well known for presenting antioxidant activity (and the parent molecule of the compound of interest in the present work). Myricetin 3,4[Formula: see text]-di-O-α-L-rhamnopyranoside presented the lowest BDE to be 79.13 kcal/mol (as determined using B3LYP/6-311G(d,p) in water) while myricetin has a quite similar value (within 3.4 kcal/mol). IPs computed in the gas phase [B3LYP/6-311G(d,p)] are 157.18 and 161.4 kcal/mol for myricetin 3,4[Formula: see text]-di-O-α-L-rhamnopyranoside and myricetin, respectively. As the values of BDEs are considerably lower than the ones probed for IPs (in the gas phase or in any given solvent environment), the hydrogen atom transfer mechanism is preferred over the single electron transfer mechanism. The BDEs obtained suggest that myricetin 3,4[Formula: see text]-di-O-α-L-rhamnopyranoside can present antioxidant potential as good as the parent molecule myricetin (a well-known antioxidant). Therefore, experimental tests on the antioxidant activity of Compound M are encouraged.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Flavonoides / Simulação por Computador / Glucosídeos / Antioxidantes Idioma: En Revista: J Mol Model Assunto da revista: BIOLOGIA MOLECULAR Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Brasil País de publicação: Alemanha
Texto completo
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Imprimir
XML
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Flavonoides / Simulação por Computador / Glucosídeos / Antioxidantes Idioma: En Revista: J Mol Model Assunto da revista: BIOLOGIA MOLECULAR Ano de publicação: 2018 Tipo de documento: Article País de afiliação: Brasil País de publicação: Alemanha