First Total Syntheses of Novel Non-Enzymatic Polyunsaturated Fatty Acid Metabolites and Their Identification in Edible Oils.
Chemistry
; 26(44): 10090-10098, 2020 Aug 06.
Article
em En
| MEDLINE
| ID: mdl-32531118
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-F3t -isoprostane (IsoP) from eicosapentaenoic acid (EPA), 20-F4t -neuroprostane (NeuroP) from docosahexaenoic acid (DHA) and 20-F3t -NeuroP from docosapentaenoic acid (DPAn-3 ) were synthesized by two complementary synthetic strategies. The first one relied on a racemic approach to 18(RS)-18-F3t -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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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Gorduras na Dieta
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Ácidos Graxos Insaturados
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Lipidômica
Tipo de estudo:
Diagnostic_studies
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article