title: Reactive Carbonyl Species Derived from Omega-3 and Omega-6 Fatty Acids.
abstract: Inflammation-related reactive oxygen species (ROS) and reactive nitrogen species (RNS) are associated with the development of cancer. ROS and RNS can directly damage biomacromolecules such as proteins, DNA, and lipids. Lipid peroxidation, however, can result in reactive carbonyl species (RCS) that can also modify proteins and DNA. In contrast to an extensive literature on the modification of proteins and DNA from omega-6 fatty acids, there are few studies on RCS generation from other fatty acids, particularly omega-3 fatty acids, which are frequently consumed from the diet and diet supplements. Therefore, a comparison between omega-3 and omega-6 fatty acids has been conducted. LC-MS/MS analysis of carbonyl-dinitrophenylhydrazine (DNPH) standards yielded characteristic fragment ions. Autoxidation products of α-linolenic acid and linoleic acid were then derivatized with DNPH and analyzed by LC-MS/MS. The results showed that α-linolenic acid, an omega-3 fatty acid, generated more acrolein and crotonaldehyde than did linoleic acid, an omega-6 fatty acid. Omega-3 fatty acids might be easily degraded to smaller monoaldehydes or dicarbonyls. Omega-3 fatty acids have been considered as health improvement components for a long time. However, on the basis of the results presented here, use of omega-3 fatty acids should be re-evaluated in vivo for safety purposes.
authors.affiliation: Food Science and Human Nutrition, Citrus Research and Education Center, University of Florida, Lake Alfred, Florida 33850, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Food Science and Human Nutrition, Citrus Research and Education Center, University of Florida, Lake Alfred, Florida 33850, United States.
authors.forename: Ping
authors.initials: P
authors.lastname: Cui
mesh_terms: D000171:Acrolein / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D015525:Fatty Acids, Omega-3 / Q000737:chemistry*; D043371:Fatty Acids, Omega-6 / Q000737:chemistry*; D019787:Linoleic Acid / Q000737:chemistry; D015227:Lipid Peroxidation; D010084:Oxidation-Reduction; D017962:alpha-Linolenic Acid / Q000737:chemistry
chemical_list: D000447:Aldehydes; D015525:Fatty Acids, Omega-3; D043371:Fatty Acids, Omega-6; D017962:alpha-Linolenic Acid; D000171:Acrolein; C012796:2-butenal; D019787:Linoleic Acid
keywords: acrolein; crotonaldehyde; omega-3 fatty acids; omega-6 fatty acids; oxidation