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Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid.
J Agric Food Chem. 2012 Dec 19; 60(50):12312-23.JA

Abstract

The main metabolites of caffeic and ferulic acids (ferulic acid-4'-O-sulfate, caffeic acid-4'-O-sulfate, and caffeic acid-3'-O-sulfate), the most representative phenolic acids in fruits and vegetables, and the acyl glucuronide of ferulic acid were synthesized, purified, and tested for their antioxidant activity in comparison with those of their parent compounds and other related phenolics. Both the ferric reducing antioxidant power (FRAP) assay and the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging method were used. Ferulic acid-4'-O-sulfate and ferulic acid-4'-O-glucuronide exhibited very low antioxidant activity, while the monosulfate derivatives of caffeic acid were 4-fold less efficient as the antioxidant than caffeic acid. The acyl glucuronide of ferulic acid showed strong antioxidant action. The antioxidant activity of caffeic acid-3'-O-glucuronide and caffeic acid-4'-O-glucuronide was also studied. Our results demonstrate that some of the products of phenolic acid metabolism still retain strong antioxidant properties. Moreover, we first demonstrate the ex vivo synthesis of the acyl glucuronide of ferulic acid by mouse liver microsomes, in addition to the phenyl glucuronide.

Authors+Show Affiliations

Agricultural Research Council, Rome, Italy.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

23157164

Citation

Piazzon, A, et al. "Antioxidant Activity of Phenolic Acids and Their Metabolites: Synthesis and Antioxidant Properties of the Sulfate Derivatives of Ferulic and Caffeic Acids and of the Acyl Glucuronide of Ferulic Acid." Journal of Agricultural and Food Chemistry, vol. 60, no. 50, 2012, pp. 12312-23.
Piazzon A, Vrhovsek U, Masuero D, et al. Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid. J Agric Food Chem. 2012;60(50):12312-23.
Piazzon, A., Vrhovsek, U., Masuero, D., Mattivi, F., Mandoj, F., & Nardini, M. (2012). Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid. Journal of Agricultural and Food Chemistry, 60(50), 12312-23. https://doi.org/10.1021/jf304076z
Piazzon A, et al. Antioxidant Activity of Phenolic Acids and Their Metabolites: Synthesis and Antioxidant Properties of the Sulfate Derivatives of Ferulic and Caffeic Acids and of the Acyl Glucuronide of Ferulic Acid. J Agric Food Chem. 2012 Dec 19;60(50):12312-23. PubMed PMID: 23157164.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antioxidant activity of phenolic acids and their metabolites: synthesis and antioxidant properties of the sulfate derivatives of ferulic and caffeic acids and of the acyl glucuronide of ferulic acid. AU - Piazzon,A, AU - Vrhovsek,U, AU - Masuero,D, AU - Mattivi,F, AU - Mandoj,F, AU - Nardini,M, Y1 - 2012/12/04/ PY - 2012/11/20/entrez PY - 2012/11/20/pubmed PY - 2013/11/12/medline SP - 12312 EP - 23 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 60 IS - 50 N2 - The main metabolites of caffeic and ferulic acids (ferulic acid-4'-O-sulfate, caffeic acid-4'-O-sulfate, and caffeic acid-3'-O-sulfate), the most representative phenolic acids in fruits and vegetables, and the acyl glucuronide of ferulic acid were synthesized, purified, and tested for their antioxidant activity in comparison with those of their parent compounds and other related phenolics. Both the ferric reducing antioxidant power (FRAP) assay and the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging method were used. Ferulic acid-4'-O-sulfate and ferulic acid-4'-O-glucuronide exhibited very low antioxidant activity, while the monosulfate derivatives of caffeic acid were 4-fold less efficient as the antioxidant than caffeic acid. The acyl glucuronide of ferulic acid showed strong antioxidant action. The antioxidant activity of caffeic acid-3'-O-glucuronide and caffeic acid-4'-O-glucuronide was also studied. Our results demonstrate that some of the products of phenolic acid metabolism still retain strong antioxidant properties. Moreover, we first demonstrate the ex vivo synthesis of the acyl glucuronide of ferulic acid by mouse liver microsomes, in addition to the phenyl glucuronide. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/23157164/Antioxidant_activity_of_phenolic_acids_and_their_metabolites:_synthesis_and_antioxidant_properties_of_the_sulfate_derivatives_of_ferulic_and_caffeic_acids_and_of_the_acyl_glucuronide_of_ferulic_acid_ L2 - https://doi.org/10.1021/jf304076z DB - PRIME DP - Unbound Medicine ER -