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Phenylpropanoid glycoside analogues: enzymatic synthesis, antioxidant activity and theoretical study of their free radical scavenger mechanism.

López-Munguía A, Hernández-Romero Y, Pedraza-Chaverri J, Miranda-Molina A, Regla I, Martínez A, Castillo E - PLoS ONE (2011)

Bottom Line: 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 single electron transfer (SPLET).The enzymatic process reported in this study is an efficient and versatile route to obtain PPGs from different phenylpropanoid acids, sugars and phenolic alcohols.

View Article: PubMed Central - PubMed

Affiliation: Departamento Ingeniería Celular y Biocatálisis, Instituto de Biotecnología, Universidad Nacional Autónoma de México, Cuernavaca, Morelos, México.

ABSTRACT
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 β-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 (DPPH•) 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 single electron transfer (SPLET). The enzymatic process reported in this study is an efficient and versatile route to obtain PPGs from different phenylpropanoid acids, sugars and phenolic alcohols.

Show MeSH
Verbascoside (Acteoside) is a PPG with applications in food and pharmaceutical sciences.The PPG molecule contains one or more sugar molecules and two antioxidants linked through an ester and glycosydic linkages.
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pone-0020115-g001: Verbascoside (Acteoside) is a PPG with applications in food and pharmaceutical sciences.The PPG molecule contains one or more sugar molecules and two antioxidants linked through an ester and glycosydic linkages.

Mentions: Phenylpropanoid glycosides (PPGs) are acylated glycoconjugates carrying a substituted arylalkyl aglycon, the acylation occurring mainly on the primary hydroxyl group with a cinnamoyl derived residue. PPGs are secondary metabolites widely distributed in plants with demonstrated therapeutical properties against hypertension, viral infections, fungal infections, tumors and cancer as well as an immunomodulatory effect [2]–. These properties have been related with the antioxidative and free radical scavenging capacities of their structural components [1]–[2], [7]. In fact, several in vitro assays have demonstrated that PPGs act as potent antioxidants by inhibiting the oxidation of low-density lipoproteins through different mechanisms such as free radical scavenging and metal ion chelation, associated with the presence of phenylpropanoid and phenylethanoid groups in their structure (Figure 1) [2]–[8].


Phenylpropanoid glycoside analogues: enzymatic synthesis, antioxidant activity and theoretical study of their free radical scavenger mechanism.

López-Munguía A, Hernández-Romero Y, Pedraza-Chaverri J, Miranda-Molina A, Regla I, Martínez A, Castillo E - PLoS ONE (2011)

Verbascoside (Acteoside) is a PPG with applications in food and pharmaceutical sciences.The PPG molecule contains one or more sugar molecules and two antioxidants linked through an ester and glycosydic linkages.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3108595&req=5

pone-0020115-g001: Verbascoside (Acteoside) is a PPG with applications in food and pharmaceutical sciences.The PPG molecule contains one or more sugar molecules and two antioxidants linked through an ester and glycosydic linkages.
Mentions: Phenylpropanoid glycosides (PPGs) are acylated glycoconjugates carrying a substituted arylalkyl aglycon, the acylation occurring mainly on the primary hydroxyl group with a cinnamoyl derived residue. PPGs are secondary metabolites widely distributed in plants with demonstrated therapeutical properties against hypertension, viral infections, fungal infections, tumors and cancer as well as an immunomodulatory effect [2]–. These properties have been related with the antioxidative and free radical scavenging capacities of their structural components [1]–[2], [7]. In fact, several in vitro assays have demonstrated that PPGs act as potent antioxidants by inhibiting the oxidation of low-density lipoproteins through different mechanisms such as free radical scavenging and metal ion chelation, associated with the presence of phenylpropanoid and phenylethanoid groups in their structure (Figure 1) [2]–[8].

Bottom Line: 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 single electron transfer (SPLET).The enzymatic process reported in this study is an efficient and versatile route to obtain PPGs from different phenylpropanoid acids, sugars and phenolic alcohols.

View Article: PubMed Central - PubMed

Affiliation: Departamento Ingeniería Celular y Biocatálisis, Instituto de Biotecnología, Universidad Nacional Autónoma de México, Cuernavaca, Morelos, México.

ABSTRACT
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 β-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 (DPPH•) 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 single electron transfer (SPLET). The enzymatic process reported in this study is an efficient and versatile route to obtain PPGs from different phenylpropanoid acids, sugars and phenolic alcohols.

Show MeSH