Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism
Phenylpropanoid glycosides (PPGs) are natural compounds present in several medicinal plants that have high antioxidant power and diverse biological activities. Because of their low content in plants (less than 5 % w/w), several chemical synthetic routes to produce PPGs have been developed, but their...
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ftciteseerx:oai:CiteSeerX.psu:10.1.1.290.5771 2023-05-15T13:50:03+02:00 Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism Agustín López-munguía Yanet Hernández-romero José Pedraza-chaverri Alfonso Mir Ignacio Regla Ana Martínez Edmundo Castillo The Pennsylvania State University CiteSeerX Archives application/zip http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.290.5771 en eng http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.290.5771 Metadata may be used without restrictions as long as the oai identifier remains attached to it. ftp://ftp.ncbi.nlm.nih.gov/pub/pmc/21/47/PLoS_One_2011_Jun_3_6(6)_e20115.tar.gz text ftciteseerx 2016-01-07T21:32:52Z Phenylpropanoid glycosides (PPGs) are natural compounds present in several medicinal plants that have high antioxidant power and diverse biological activities. Because of their low content in plants (less than 5 % w/w), several chemical synthetic routes to produce PPGs have been developed, but their synthesis is a time consuming process and the achieved yields are often low. In this study, an alternative and efficient two-step biosynthetic route to obtain natural PPG analogues is reported for the first time. Two galactosides were initially synthesized from vanillyl alcohol and homovanillyl alcohol by a transgalactosylation reaction catalyzed by Kluyveromyces lactis b-galactosidase in saturated lactose solutions with a 30%– 35 % yield. To synthesize PPGs, the galactoconjugates were esterified with saturated and unsaturated hydroxycinnamic acid derivatives using Candida antarctica Lipase B (CaL-B) as a biocatalyst with 40%–60 % yields. The scavenging ability of the phenolic raw materials, intermediates and PPGs was evaluated by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPHN) method. It was found that the biosynthesized PPGs had higher scavenging abilities when compared to ascorbic acid, the reference compound, while their antioxidant activities were found similar to that of natural PPGs. Moreover, density functional theory (DFT) calculations were used to determine that the PPGs antioxidant mechanism proceeds through a sequential proton loss Text Antarc* Antarctica Unknown |
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Phenylpropanoid glycosides (PPGs) are natural compounds present in several medicinal plants that have high antioxidant power and diverse biological activities. Because of their low content in plants (less than 5 % w/w), several chemical synthetic routes to produce PPGs have been developed, but their synthesis is a time consuming process and the achieved yields are often low. In this study, an alternative and efficient two-step biosynthetic route to obtain natural PPG analogues is reported for the first time. Two galactosides were initially synthesized from vanillyl alcohol and homovanillyl alcohol by a transgalactosylation reaction catalyzed by Kluyveromyces lactis b-galactosidase in saturated lactose solutions with a 30%– 35 % yield. To synthesize PPGs, the galactoconjugates were esterified with saturated and unsaturated hydroxycinnamic acid derivatives using Candida antarctica Lipase B (CaL-B) as a biocatalyst with 40%–60 % yields. The scavenging ability of the phenolic raw materials, intermediates and PPGs was evaluated by the 2,2-diphenyl-1-picrylhydrazyl radical (DPPHN) method. It was found that the biosynthesized PPGs had higher scavenging abilities when compared to ascorbic acid, the reference compound, while their antioxidant activities were found similar to that of natural PPGs. Moreover, density functional theory (DFT) calculations were used to determine that the PPGs antioxidant mechanism proceeds through a sequential proton loss |
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The Pennsylvania State University CiteSeerX Archives |
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Agustín López-munguía Yanet Hernández-romero José Pedraza-chaverri Alfonso Mir Ignacio Regla Ana Martínez Edmundo Castillo |
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Agustín López-munguía Yanet Hernández-romero José Pedraza-chaverri Alfonso Mir Ignacio Regla Ana Martínez Edmundo Castillo Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism |
author_facet |
Agustín López-munguía Yanet Hernández-romero José Pedraza-chaverri Alfonso Mir Ignacio Regla Ana Martínez Edmundo Castillo |
author_sort |
Agustín López-munguía |
title |
Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism |
title_short |
Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism |
title_full |
Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism |
title_fullStr |
Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism |
title_full_unstemmed |
Phenylpropanoid Glycoside Analogues: Enzymatic Synthesis, Antioxidant Activity and Theoretical Study of Their Free Radical Scavenger Mechanism |
title_sort |
phenylpropanoid glycoside analogues: enzymatic synthesis, antioxidant activity and theoretical study of their free radical scavenger mechanism |
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http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.290.5771 |
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Antarc* Antarctica |
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Antarc* Antarctica |
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ftp://ftp.ncbi.nlm.nih.gov/pub/pmc/21/47/PLoS_One_2011_Jun_3_6(6)_e20115.tar.gz |
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http://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.290.5771 |
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