Free Radical Scavenging Activity of Carbonyl-Amine Adducts Formed in Soybean Oil Fortified with Phosphatidylethanolamine

• Published in: Molecules (Basel, Switzerland) Vol. 25; no. 2; p. 373
• Main Authors: Goritschnig, Jana, Tadus, Klaudia, König, Jürgen, Pignitter, Marc
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 16.01.2020; MDPI
• Subjects: Adducts; Aldehydes; Browning; Carbonyl compounds; carbonyl-amine adducts; Carbonyls; Cold; Dihydropyridine; Fatty acids; Free radicals; Hexanal; Linoleic acid; lipid oxidation; Lipid peroxidation; Lipids; Oxidation; Phosphatidylethanolamine; radical scavenging activity; Reaction products; Scavenging; Soybean oil; Soybeans; Stability; Vegetable oils; hexanal; carbonyl-amine adducts; lipid oxidation; radical scavenging activity; phosphatidylethanolamine; soybean oil
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules25020373

Non-enzymatic browning reactions between lipid aldehydes and aminophospholipids might play an important role in the oxidative stability of cold-pressed vegetable oils. We, therefore, aimed to study the Maillard-type reaction between hexanal, a lipid oxidation product of linoleic acid, and phosphatidylethanolamine (PE (16:0/18:1)) at a ratio of 2:1 at conditions representative of the extraction of cold-pressed soybean oils (CPSBO) and determine the radical scavenging activity of the carbonyl-amine adducts with the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The reaction product, 2-pentyl-3,5-dibutyl-dihydropyridine, could be identified by means of LC-ESI-QTOF-MS/MS. The formation of this nitrogen-containing heterocycle significantly increased with time and temperature ( < 0.05). The products formed during the carbonyl-amine reaction between PE (16:0/18:1) and hexanal at 60 °C showed a radical scavenging activity of approximately 20% ( < 0.05). The fraction, containing 2-pentyl-3,5-dibutyl-dihydropyridine, contributed to, but was not solely responsible for, the radical scavenging activity ( < 0.05). Incubation of CPSBO fortified with PE (16:0/18:1) at 60 °C for 60 min had the strongest radical scavenging activity of 85.1 ± 0.62%. Besides 2-pentyl-3,5-dibutyl-dihydropyridine, other carbonyl-amine adducts might impact the radical scavenging activity of CPSBO as well. The oxidative stability of CPSBO might be increased by promoting the formation of carbonyl-amine reaction products, such as 2-pentyl-3,5-dibutyl-dihydropyridine.