Model studies on the degradation of phenylalanine initiated by lipid hydroperoxides and their secondary and tertiary oxidation products

Journal of Agricultural and Food Chemistry
Rosario ZamoraFrancisco J Hidalgo

Abstract

The reaction of methyl 13-hydroperoxyoctadeca-9,11-dienoate (MeLOOH), methyl 13-hydroperoxyoctadeca-9,11,15-trienoate (MeLnOOH), methyl 13-hydroxyoctadeca-9,11-dienoate (MeLOH), methyl 13-oxooctadeca-9,11-dienoate (MeLCO), methyl 9,10-epoxy-13-hydroxy-11-octadecenoate (MeLEPOH), and methyl 9,10-epoxy-13-oxo-11-octadecenoate (MeLEPCO) with phenylalanine was studied to determine the comparative reactivity of primary, secondary, and tertiary lipid oxidation products in the Strecker degradation of amino acids. All assayed lipids were able to degrade the amino acid to a high extent, although the lipid reactivity decreased slightly in the following order: MeLEPCO > or = MeLCO > MeLEPOH > or = MeLOH > MeLOOH approximately = MeLnOOH. These data confirmed the ability of many lipid oxidation products to degrade amino acids by a Strecker-type mechanism and suggested that, once the lipid oxidation is produced, a significant Strecker degradation of surrounding amino acids should be expected. The contribution of different competitive mechanisms to this degradation is proposed, among which the conversion of the different lipid oxidation products assayed into the most reactive MeLEPCO and the fractionation of long-chain primary and secondary l...Continue Reading

References

Jan 1, 1989·Free Radical Biology & Medicine·H W Gardner
May 6, 2004·Journal of the American Chemical Society·Mingjiang Sun, Robert G Salomon
Nov 13, 2004·Journal of Agricultural and Food Chemistry·Francisco J Hidalgo, Rosario Zamora
Feb 22, 2005·Chemical Research in Toxicology·Rosario Zamora, Francisco J Hidalgo
Feb 26, 2005·Critical Reviews in Food Science and Nutrition·Rosario Zamora, Francisco J Hidalgo
May 26, 2005·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Dec 22, 2005·Journal of Agricultural and Food Chemistry·Francisco J HidalgoRosario Zamora
Mar 16, 2006·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Aug 3, 2006·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Feb 16, 2007·Journal of Agricultural and Food Chemistry·Rosario ZamoraFrancisco J Hidalgo
Apr 5, 2008·Journal of Agricultural and Food Chemistry·Emerenciana GallardoFrancisco J Hidalgo
May 2, 2008·Annals of the New York Academy of Sciences·Francisco J Hidalgo, Rosario Zamora

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Citations

Oct 25, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jose Sanchez del PulgarJorge Ruiz-Carrascal
Mar 6, 2012·Journal of Food Science·Mariagrazia GiarnettiTommaso Gomes
Mar 10, 2015·Critical Reviews in Food Science and Nutrition·Francisco J Hidalgo, Rosario Zamora
Oct 17, 2014·The Journal of Organic Chemistry·Saroj Ranjan DeJohn R Falck
Nov 7, 2018·Journal of Agricultural and Food Chemistry·Silvia Marzocchi, Maria Fiorenza Caboni
Sep 11, 2010·Journal of Agricultural and Food Chemistry·Francisco J HidalgoRosario Zamora

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