Browsing by Subject "Lipid oxidation"

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Enzymatically formed fatty acid hydroperoxides determined through GC‐MS analysis of enantiomeric excess of hydroxy fatty acids after reduction and ibuprofen derivatization
(2025) Hotz, Lisa; Zartmann, Anne; Noack, Isabelle; Drees, Luca J.; Kuschow, Meret K.; Heinrich, Markus R.; Janssen, Hans‐Gerd; Hammann, Simon
Unsaturated fatty acids are susceptible to lipid oxidation through autoxidation, photooxygenation or enzymatical oxidation. A characteristic feature of enzyme‐catalyzed oxidation is the high regio‐ and stereospecificity of the formed fatty acid hydroperoxides. In this study, we present a method to quantify enzymatic lipid oxidation through reducing hydroperoxy fatty acid methyl esters to hydroxy fatty acid methyl esters and derivatizing them with enantiopure (S)‐ibuprofen, allowing the resolution of the enantiomer pairs as diastereomers via achiral GC‐MS. After application to enantiopure reference fatty acids, the approach was applied to autoxidation products of linoleic acid, and the expected racemic mixtures of the 9‐ and 13‐hydroperoxide derived hydroxy fatty acids were detected. On the other hand, when linoleic acid was oxidized using soybean lipoxygenase, clear enantiomeric excess of the (13S) enantiomer could be detected, proving the applicability of this method to detect enzymatic oxidation through enantiomeric excess.
Interactions between lipid oxidation and anthocyanins from black carrots in ω-3 fatty acid-rich flaxseed oil-in-water emulsions
(2024) Klinger, Evelyn; Salminen, Hanna; Bause, Karola; Weiss, Jochen
The application of anthocyanins as red colorants in lipid-containing foods such as oil-in-water emulsions is challenging due to their ability to act as antioxidants and their instability under various environmental conditions. In this study, we investigated the kinetics of black carrot anthocyanin degradation and the subsequent color loss influenced by lipid oxidation reactions in 1% ( w/w ) flaxseed oil-in-water emulsions stabilized by 0.1% ( w/w ) sodium dodecyl sulfate (SDS) at pH 2 upon storage at 35 °C for ten days under light and in the dark. Oxidatively stable Miglyol oil-in-water emulsions and SDS solutions were used as reference. The results showed simultaneous formation of lipid hydroperoxides and degradation of anthocyanins. The addition of anthocyanins decreased lipid hydroperoxide formation, confirming the antioxidant activity of anthocyanins through radical scavenging mechanism. The kinetic modelling of lipid oxidation and anthocyanin degradation are particularly important for estimating color stability in colored emulsion-based food systems such as dairy or non-dairy milk or yoghurt drinks.
New fluorogenic triacylglycerols as sensors for dynamic measurement of lipid oxidation
(2025) Handke, Maria; Beierlein, Frank; Imhof, Petra; Schiedel, Matthias; Hammann, Simon
Lipids are major constituents of food but are also highly relevant substructures of drugs and are increasingly applied for the development of lipid-based drug delivery systems. Lipids are prone to oxidative degradation, thus affecting the quality of food or medicines. Therefore, analytical methods or tools that enable the degree of lipid oxidation to be assessed are of utmost importance to guarantee food and drug safety. Herein, we report the design, synthesis and application of the first-in-class fluorogenic triacylglycerols that enable dynamic monitoring of lipid oxidation via straightforward fluorescence readout. Our fluorogenic triacylglycerols can be used in both aqueous and lipid-based environments. Furthermore, we showed that the sensitivity of our fluorescent tracers towards oxidation could be tuned by incorporating either saturated or unsaturated acyl chains in their triacylglycerol core structure. With this, we provide a first proof of principle for the applicability of fluorescently labelled triacylglycerols as tracers to monitor the dynamics of lipid oxidation, thus paving the way for novel discoveries in the area of lipid analytics.
Stability of anthocyanin extracts from chokeberry, grape, hibiscus, and purple sweet potato in ω-3-fatty acid rich oil-in-water emulsions
(2024) Klinger, Evelyn; Salminen, Hanna; Bause, Karola; Weiss, Jochen
The food industry is actively investigating the stability of natural red pigments to replace artificial food colorants from all food applications in the near future. In this study, the stability of coloring extracts from chokeberry, grape, hibiscus, and purple sweet potato was investigated in ω-3 fatty acid-rich flaxseed oil-in-water emulsion during storage. The red color of the oil-in-water emulsions faded within 4 days, indicating that the anthocyanin extracts were susceptible to lipid oxidation reactions of the ω-3 fatty acids. The color stability varied between all used extract sources: The chokeberry (degradation constant k = 19.6 h−1) and grape (k = 15.2 h−1) extracts showed similar degradation kinetics, whereas purple sweet potato extract (k = 10.7 h−1) degraded significantly slower, and hibiscus extract (k = 110.2 h−1) significantly faster. The differences can be explained by the different anthocyanins contained in the plant extract, especially by the proportion of acylated anthocyanins.