多不饱和脂肪酸
二十二碳五烯酸
化学
六烯酸
二十碳五烯酸
脂质过氧化
生物化学
酶
异前列腺素
脂肪酸
作者
Tereza Pavlíčková,Valérie Bultel‐Poncé,Alexandre Guy,Amandine Rocher,Guillaume Réversat,Claire Vigor,Thierry Durand,Jean‐Marie Galano,Ullrich Jahn,Camille Oger
标识
DOI:10.1002/chem.202002138
摘要
Abstract Oxidative stress (OS) is an in vivo process leading to free radical overproduction, which triggers polyunsaturated fatty acid (PUFA) peroxidation resulting in the formation of racemic non‐enzymatic oxygenated metabolites. As potential biomarkers of OS, their in vivo quantification is of great interest. However, since a large number of isomeric metabolites is formed in parallel, their quantification remains difficult without primary standards. Three new PUFA‐metabolites, namely 18‐F 3t ‐isoprostane (IsoP) from eicosapentaenoic acid (EPA), 20‐F 4t ‐neuroprostane (NeuroP) from docosahexaenoic acid (DHA) and 20‐F 3t ‐NeuroP from docosapentaenoic acid (DPA n‐3 ) were synthesized by two complementary synthetic strategies. The first one relied on a racemic approach to 18( RS )‐18‐F 3t ‐IsoP using an oxidative radical anion cyclization as a key step, whereas the second used an enzymatic deracemization of a bicyclo[3.3.0]octene intermediate obtained from cyclooctadiene to pursue an asymmetric synthesis. The synthesized metabolites were applied in targeted lipidomics to prove lipid peroxidation in edible oils of commercial nutraceuticals.
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