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A Theoretical Study on the Antioxidant Activity of Piceatannol and Isorhapontigenin Scavenging Nitric Oxide and Nitrogen Dioxide Radicals
The antioxidant activity of naturally occurring stilbene compounds piceatannol (PIC) and isorhapontigenin (ISO) scavenging two free radicals (NO and NO2) were studied using density functional theory (DFT) method. Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical ad...
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| Published in: | PloS one 2017-01, Vol.12 (1), p.e0169773-e0169773 |
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| creator | Lu, Yang Wang, AiHua Shi, Peng Zhang, Hui |
| description | The antioxidant activity of naturally occurring stilbene compounds piceatannol (PIC) and isorhapontigenin (ISO) scavenging two free radicals (NO and NO2) were studied using density functional theory (DFT) method. Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical adduct formation (RAF), single electron transfer (SET), and sequential proton loss electron transfer (SPLET). The reaction channels in water solution were traced independently, and the respective thermodynamic and kinetic parameters were obtained. We found PIC and ISO scavenge NO mainly through RAF mechanism, and scavenge NO2 through HAT mechanism. The capacity of PIC scavenging NO2 is much higher than ISO, but the reactivity of scavenging NO is lower than ISO. |
| doi_str_mv | 10.1371/journal.pone.0169773 |
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Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical adduct formation (RAF), single electron transfer (SET), and sequential proton loss electron transfer (SPLET). The reaction channels in water solution were traced independently, and the respective thermodynamic and kinetic parameters were obtained. We found PIC and ISO scavenge NO mainly through RAF mechanism, and scavenge NO2 through HAT mechanism. The capacity of PIC scavenging NO2 is much higher than ISO, but the reactivity of scavenging NO is lower than ISO.</description><identifier>ISSN: 1932-6203</identifier><identifier>EISSN: 1932-6203</identifier><identifier>DOI: 10.1371/journal.pone.0169773</identifier><identifier>PMID: 28068377</identifier><language>eng</language><publisher>United States: Public Library of Science</publisher><subject>Algorithms ; Anti-infective agents ; Antioxidants ; Antioxidants (Nutrients) ; Antioxidants - chemistry ; Antioxidants - pharmacology ; Biology and Life Sciences ; Chemical properties ; Density functional theory ; DNA damage ; Electron transfer ; Energy ; Engineering ; Free Radical Scavengers - pharmacology ; Free radicals ; Hydrogen ; Hydrogen atoms ; Models, Molecular ; Models, Theoretical ; Molecular Conformation ; Nitric oxide ; Nitric Oxide - chemistry ; Nitric Oxide - metabolism ; Nitrogen dioxide ; Nitrogen Dioxide - chemistry ; Nitrogen Dioxide - metabolism ; Oxidation ; Physical chemistry ; Physical Sciences ; Piceatannol ; Polyphenols ; Prevention ; Reaction mechanisms ; Scavenging ; Solvents ; Stilbene ; Stilbenes - chemistry ; Stilbenes - pharmacology ; Studies</subject><ispartof>PloS one, 2017-01, Vol.12 (1), p.e0169773-e0169773</ispartof><rights>COPYRIGHT 2017 Public Library of Science</rights><rights>2017 Lu et al. 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Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical adduct formation (RAF), single electron transfer (SET), and sequential proton loss electron transfer (SPLET). The reaction channels in water solution were traced independently, and the respective thermodynamic and kinetic parameters were obtained. We found PIC and ISO scavenge NO mainly through RAF mechanism, and scavenge NO2 through HAT mechanism. 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Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>PloS one</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lu, Yang</au><au>Wang, AiHua</au><au>Shi, Peng</au><au>Zhang, Hui</au><au>Salahub, Dennis</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Theoretical Study on the Antioxidant Activity of Piceatannol and Isorhapontigenin Scavenging Nitric Oxide and Nitrogen Dioxide Radicals</atitle><jtitle>PloS one</jtitle><addtitle>PLoS One</addtitle><date>2017-01-09</date><risdate>2017</risdate><volume>12</volume><issue>1</issue><spage>e0169773</spage><epage>e0169773</epage><pages>e0169773-e0169773</pages><issn>1932-6203</issn><eissn>1932-6203</eissn><abstract>The antioxidant activity of naturally occurring stilbene compounds piceatannol (PIC) and isorhapontigenin (ISO) scavenging two free radicals (NO and NO2) were studied using density functional theory (DFT) method. Four reaction mechanisms have been considered: hydrogen atom transfer (HAT), radical adduct formation (RAF), single electron transfer (SET), and sequential proton loss electron transfer (SPLET). The reaction channels in water solution were traced independently, and the respective thermodynamic and kinetic parameters were obtained. We found PIC and ISO scavenge NO mainly through RAF mechanism, and scavenge NO2 through HAT mechanism. The capacity of PIC scavenging NO2 is much higher than ISO, but the reactivity of scavenging NO is lower than ISO.</abstract><cop>United States</cop><pub>Public Library of Science</pub><pmid>28068377</pmid><doi>10.1371/journal.pone.0169773</doi><tpages>e0169773</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Algorithms Anti-infective agents Antioxidants Antioxidants (Nutrients) Antioxidants - chemistry Antioxidants - pharmacology Biology and Life Sciences Chemical properties Density functional theory DNA damage Electron transfer Energy Engineering Free Radical Scavengers - pharmacology Free radicals Hydrogen Hydrogen atoms Models, Molecular Models, Theoretical Molecular Conformation Nitric oxide Nitric Oxide - chemistry Nitric Oxide - metabolism Nitrogen dioxide Nitrogen Dioxide - chemistry Nitrogen Dioxide - metabolism Oxidation Physical chemistry Physical Sciences Piceatannol Polyphenols Prevention Reaction mechanisms Scavenging Solvents Stilbene Stilbenes - chemistry Stilbenes - pharmacology Studies |
| title | A Theoretical Study on the Antioxidant Activity of Piceatannol and Isorhapontigenin Scavenging Nitric Oxide and Nitrogen Dioxide Radicals |
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