Limits...
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
FEDAM in water.Dashed lines are only included to aid visualization. Molecules located below the dashed line are better electron donors when compared to DPPH•. Triangles represent compound 3, circles represent compound 10 and squares represent values of the deprotonated compounds of 5, 6, 7 and 8. β-carotene (BC) and astaxanthin (ASTA) are included for comparison.
© Copyright Policy
Related In: Results  -  Collection


getmorefigures.php?uid=PMC3108595&req=5

pone-0020115-g006: FEDAM in water.Dashed lines are only included to aid visualization. Molecules located below the dashed line are better electron donors when compared to DPPH•. Triangles represent compound 3, circles represent compound 10 and squares represent values of the deprotonated compounds of 5, 6, 7 and 8. β-carotene (BC) and astaxanthin (ASTA) are included for comparison.

Mentions: To compare with the experimental results, the DPPH• was also calculated. Using RIE and REA, it was possible to locate these molecules in the FEDAM as shown in Figure 5, where previously reported values for β-carotene and astaxanthin are also included for comparison. As shown in Figure 6, among these molecules, DPPH• is the best electron acceptor.


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)

FEDAM in water.Dashed lines are only included to aid visualization. Molecules located below the dashed line are better electron donors when compared to DPPH•. Triangles represent compound 3, circles represent compound 10 and squares represent values of the deprotonated compounds of 5, 6, 7 and 8. β-carotene (BC) and astaxanthin (ASTA) are included for comparison.
© Copyright Policy
Related In: Results  -  Collection

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

pone-0020115-g006: FEDAM in water.Dashed lines are only included to aid visualization. Molecules located below the dashed line are better electron donors when compared to DPPH•. Triangles represent compound 3, circles represent compound 10 and squares represent values of the deprotonated compounds of 5, 6, 7 and 8. β-carotene (BC) and astaxanthin (ASTA) are included for comparison.
Mentions: To compare with the experimental results, the DPPH• was also calculated. Using RIE and REA, it was possible to locate these molecules in the FEDAM as shown in Figure 5, where previously reported values for β-carotene and astaxanthin are also included for comparison. As shown in Figure 6, among these molecules, DPPH• is the best electron acceptor.

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