Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species
Quantum mechanical calculations at B3LYP/6-31G** level of theory were employed to obtain energy (E), ionization potential (IP), bond dissociation enthalpy (O-H BDE) and stabilization energies (DEiso) in order to infer the scavenging activity of dihydrochalcones (DHC) and structurally related compoun...
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MDPI AG
2011-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/16/2/1749/ |
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| author | Alexandre L. A. Bentes Rosivaldo S. Borges Waldinei R. Monteiro Luiz G. M. de Macedo Cláudio N. Alves |
| author_facet | Alexandre L. A. Bentes Rosivaldo S. Borges Waldinei R. Monteiro Luiz G. M. de Macedo Cláudio N. Alves |
| author_sort | Alexandre L. A. Bentes |
| collection | DOAJ |
| description | Quantum mechanical calculations at B3LYP/6-31G** level of theory were employed to obtain energy (E), ionization potential (IP), bond dissociation enthalpy (O-H BDE) and stabilization energies (DEiso) in order to infer the scavenging activity of dihydrochalcones (DHC) and structurally related compounds. Spin density calculations were also performed for the proposed antioxidant activity mechanism of 2,4,6-trihydroxyacetophenone (2,4,6-THA). The unpaired electron formed by the hydrogen abstraction from the phenolic hydroxyl group of 2,4,6-THA is localized on the phenolic oxygen at 2, 6, and 4 positions, the C3 and C6 carbon atoms at ortho positions, and the C5 carbon atom at para position. The lowest phenolic oxygen contribution corresponded to the highest scavenging activity value. It was found that antioxidant activity depends on the presence of a hydroxyl at the C2 and C4 positions and that there is a correlation between IP and O-H BDE and peroxynitrite scavenging activity and lipid peroxidation. These results identified the pharmacophore group for DHC. |
| first_indexed | 2024-12-10T14:33:38Z |
| format | Article |
| id | doaj.art-7f58816999a74b9298f7feefe132f7af |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-10T14:33:38Z |
| publishDate | 2011-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7f58816999a74b9298f7feefe132f7af2022-12-22T01:44:53ZengMDPI AGMolecules1420-30492011-02-011621749176010.3390/molecules16021749Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical SpeciesAlexandre L. A. BentesRosivaldo S. BorgesWaldinei R. MonteiroLuiz G. M. de MacedoCláudio N. AlvesQuantum mechanical calculations at B3LYP/6-31G** level of theory were employed to obtain energy (E), ionization potential (IP), bond dissociation enthalpy (O-H BDE) and stabilization energies (DEiso) in order to infer the scavenging activity of dihydrochalcones (DHC) and structurally related compounds. Spin density calculations were also performed for the proposed antioxidant activity mechanism of 2,4,6-trihydroxyacetophenone (2,4,6-THA). The unpaired electron formed by the hydrogen abstraction from the phenolic hydroxyl group of 2,4,6-THA is localized on the phenolic oxygen at 2, 6, and 4 positions, the C3 and C6 carbon atoms at ortho positions, and the C5 carbon atom at para position. The lowest phenolic oxygen contribution corresponded to the highest scavenging activity value. It was found that antioxidant activity depends on the presence of a hydroxyl at the C2 and C4 positions and that there is a correlation between IP and O-H BDE and peroxynitrite scavenging activity and lipid peroxidation. These results identified the pharmacophore group for DHC.http://www.mdpi.com/1420-3049/16/2/1749/DFTantioxidant activitySARdihydrochalcone derivativesionization potentialbond dissociation enthalpyROS and RNS |
| spellingShingle | Alexandre L. A. Bentes Rosivaldo S. Borges Waldinei R. Monteiro Luiz G. M. de Macedo Cláudio N. Alves Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species Molecules DFT antioxidant activity SAR dihydrochalcone derivatives ionization potential bond dissociation enthalpy ROS and RNS |
| title | Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species |
| title_full | Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species |
| title_fullStr | Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species |
| title_full_unstemmed | Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species |
| title_short | Structure of Dihydrochalcones and Related Derivatives and Their Scavenging and Antioxidant Activity against Oxygen and Nitrogen Radical Species |
| title_sort | structure of dihydrochalcones and related derivatives and their scavenging and antioxidant activity against oxygen and nitrogen radical species |
| topic | DFT antioxidant activity SAR dihydrochalcone derivatives ionization potential bond dissociation enthalpy ROS and RNS |
| url | http://www.mdpi.com/1420-3049/16/2/1749/ |
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