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Effect of phenolic compounds on the formation of alpha-aminoadipic and gamma-glutamic semialdehydes from myofibrillar proteins oxidized by copper, iron, and myoglobin.
J Agric Food Chem. 2010 Apr 14; 58(7):4448-55.JA

Abstract

The effect of selected phenolic compounds, namely, gallic acid, chlorogenic acid, genistein, catechin, cyanidin-3-glucoside and rutin, on the formation of specific protein carbonyls, alpha-aminoadipic and gamma-glutamic semialdehydes (AAS and GGS, respectively), from oxidized myofibrillar proteins, was studied in the present article. Suspensions containing myofibrillar proteins (20 mg/mL) and the aforementioned phenolic compounds (1 mM) were oxidized (37 degrees C for 20 days) in the presence of copper acetate, iron (FeCl(3)), or myoglobin (10 microM) in combination with 1 mM H(2)O(2) and analyzed for AAS and GGS using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS). Suspensions with added alpha-tocopherol (1 mM) and a control group (with no phenolic compound) were also considered. In the presence of copper, the alpha-tocopherol and most phenolic compounds significantly inhibited the formation of AAS and GGS. In iron- and myoglobin-oxidized suspensions, however, some of those phenolic compounds (i.e., chlorogenic acid and genistein) promoted the formation of the semialdehydes. Besides the influence of the oxidation promoters, the overall effect of plant phenolics on protein oxidation is likely affected by the chemical structure of the phenolics and the result of the interactions between these compounds and myofibrillar proteins. Plausible mechanisms for the antioxidant and pro-oxidant effects of plant phenolics on myofibrillar proteins are proposed in the present article. This study highlights the complexity of redox reactions between plant phenolics and oxidizing myofibrillar proteins.

Authors+Show Affiliations

Department of Food and Environmental Sciences, Food Chemistry, University of Helsinki, Helsinki, Finland. mariovet@unex.esNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

20196602

Citation

Estévez, Mario, and Marina Heinonen. "Effect of Phenolic Compounds On the Formation of Alpha-aminoadipic and Gamma-glutamic Semialdehydes From Myofibrillar Proteins Oxidized By Copper, Iron, and Myoglobin." Journal of Agricultural and Food Chemistry, vol. 58, no. 7, 2010, pp. 4448-55.
Estévez M, Heinonen M. Effect of phenolic compounds on the formation of alpha-aminoadipic and gamma-glutamic semialdehydes from myofibrillar proteins oxidized by copper, iron, and myoglobin. J Agric Food Chem. 2010;58(7):4448-55.
Estévez, M., & Heinonen, M. (2010). Effect of phenolic compounds on the formation of alpha-aminoadipic and gamma-glutamic semialdehydes from myofibrillar proteins oxidized by copper, iron, and myoglobin. Journal of Agricultural and Food Chemistry, 58(7), 4448-55. https://doi.org/10.1021/jf903757h
Estévez M, Heinonen M. Effect of Phenolic Compounds On the Formation of Alpha-aminoadipic and Gamma-glutamic Semialdehydes From Myofibrillar Proteins Oxidized By Copper, Iron, and Myoglobin. J Agric Food Chem. 2010 Apr 14;58(7):4448-55. PubMed PMID: 20196602.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Effect of phenolic compounds on the formation of alpha-aminoadipic and gamma-glutamic semialdehydes from myofibrillar proteins oxidized by copper, iron, and myoglobin. AU - Estévez,Mario, AU - Heinonen,Marina, PY - 2010/3/4/entrez PY - 2010/3/4/pubmed PY - 2010/9/2/medline SP - 4448 EP - 55 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 58 IS - 7 N2 - The effect of selected phenolic compounds, namely, gallic acid, chlorogenic acid, genistein, catechin, cyanidin-3-glucoside and rutin, on the formation of specific protein carbonyls, alpha-aminoadipic and gamma-glutamic semialdehydes (AAS and GGS, respectively), from oxidized myofibrillar proteins, was studied in the present article. Suspensions containing myofibrillar proteins (20 mg/mL) and the aforementioned phenolic compounds (1 mM) were oxidized (37 degrees C for 20 days) in the presence of copper acetate, iron (FeCl(3)), or myoglobin (10 microM) in combination with 1 mM H(2)O(2) and analyzed for AAS and GGS using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS). Suspensions with added alpha-tocopherol (1 mM) and a control group (with no phenolic compound) were also considered. In the presence of copper, the alpha-tocopherol and most phenolic compounds significantly inhibited the formation of AAS and GGS. In iron- and myoglobin-oxidized suspensions, however, some of those phenolic compounds (i.e., chlorogenic acid and genistein) promoted the formation of the semialdehydes. Besides the influence of the oxidation promoters, the overall effect of plant phenolics on protein oxidation is likely affected by the chemical structure of the phenolics and the result of the interactions between these compounds and myofibrillar proteins. Plausible mechanisms for the antioxidant and pro-oxidant effects of plant phenolics on myofibrillar proteins are proposed in the present article. This study highlights the complexity of redox reactions between plant phenolics and oxidizing myofibrillar proteins. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/20196602/Effect_of_phenolic_compounds_on_the_formation_of_alpha_aminoadipic_and_gamma_glutamic_semialdehydes_from_myofibrillar_proteins_oxidized_by_copper_iron_and_myoglobin_ L2 - https://doi.org/10.1021/jf903757h DB - PRIME DP - Unbound Medicine ER -