First Total Syntheses of Novel Non‐Enzymatic Polyunsaturated Fatty Acid Metabolites and Their Identification in Edible Oils

Pavlíčková, Tereza; Bultel-Poncé, Valérie; Guy, Alexandre; Rocher, Amandine; Réversat, Guillaume; Vigor, Claire; Galano, Jean‐Marie; Jahn, Ullrich; Oger, Camille

doi:10.1002/chem.202002138

Cited by 5 publications

(9 citation statements)

References 27 publications

(27 reference statements)

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“…Since isoprostanoids are chemically relatively stable at ambient conditions, it will be interesting to evaluate if specific members could be suitable markers for secondary oxidation in omega-3 EPA/DHA oils, including low-grade oxidation in ingredient oils and finished products. Recently, neuroprostanes derived from DHA and isoprostanes from EPA were shown to be present in two encapsulated marine dietary supplement oils: calanus oil and a fish oil composed of a mixture of sardine, anchovy, mackerel, and herring oil [ 83 ].…”

Section: Discussionmentioning

confidence: 99%

Chemical Compositional Changes in Over-Oxidized Fish Oils

Phung

Bannenberg²,

Vigor

et al. 2020

Foods

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A recent study has reported that the administration during gestation of a highly rancid hoki liver oil, obtained by oxidation through sustained exposure to oxygen gas and incident light for 30 days, causes newborn mortality in rats. This effect was attributed to lipid hydroperoxides formed in the omega-3 long-chain polyunsaturated fatty acid-rich oil, while other chemical changes in the damaged oil were overlooked. In the present study, the oxidation condition employed to damage the hoki liver oil was replicated, and the extreme rancidity was confirmed. A detailed analysis of temporal chemical changes resulting from the sustained oxidative challenge involved measures of eicosapentaenoic acid/docosahexaenoic acid (EPA/DHA) omega-3 oil oxidative quality (peroxide value, para-anisidine value, total oxidation number, acid value, oligomers, antioxidant content, and induction time) as well as changes in fatty acid content, volatiles, isoprostanoids, and oxysterols. The chemical description was extended to refined anchovy oil, which is a more representative ingredient oil used in omega-3 finished products. The present study also analyzed the effects of a different oxidation method involving thermal exposure in the dark in contact with air, which is an oxidation condition that is more relevant to retail products. The two oils had different susceptibility to the oxidation conditions, resulting in distinct chemical oxidation signatures that were determined primarily by antioxidant protection as well as specific methodological aspects of the applied oxidative conditions. Unique isoprostanoids and oxysterols were formed in the over-oxidized fish oils, which are discussed in light of their potential biological activities.

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Section: Discussionmentioning

confidence: 99%

Chemical Compositional Changes in Over-Oxidized Fish Oils

Phung

Bannenberg²,

Vigor

et al. 2020

Foods

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“…[120] A majority of studies focuses on profiling the oxylipins with the aim to report the contents for potential future use in pharmaceutical or cosmetic industry and to refer to the biological properties of these oxylipins, as mentioned in the above paragraph. Thus, the profiles of oxylipins were described in a diversity of plant matrices : plant leaves, [120] algae, [131,132] food (seeds, nuts, edible oils) [79,119,133] and by-products of the food industry. [134] Finally, in the context of the food industry, PhytoPs and PhytoFs could find their place as marker of oxidative stress during the industrial process as suggested by Gil-Izquierdo's group and would be a guarantee of the quality of the transformed product.…”

Section: Objectives Of Isoprostanoid Measurements In Plantsmentioning

confidence: 99%

Isoprostanoids, Isofuranoids and Isoketals – From Synthesis to Lipidomics

et al. 2022

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A huge diversity of oxygenated metabolites originated from polyunsaturated fatty acids (PUFAs) had been discovered. Radical cascades are involved in the biosynthesis of these metabolites, and the radical initiation can be performed either inside the active site of an enzyme in the extracellular medium, or in membrane on phospholipids. The development of convergent and flexible chemical strategies to prepare these compounds by organic chemists, along with the development of sophisticated mass spectrometry methods, has boosted the knowledge regarding PUFA metabolites. Also, isoprostanoids have emerged as indicators of oxidative stress in humans and their environment. This Review provides a brief overview on the chemical strategies and analytical methods achieved over the past thirty years.

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“…Our recent work already shown that the 10-F4t-NeuroP have anti-arrhythmic effects 18 and 14-F4t-NeuroP was found in edible-oils. 19 The experimental section has no title; please leave this line here.…”

Section: Scheme 5: Final Deprotectionsmentioning

confidence: 99%

“…Our recent work has already shown that the 10-F 4t -NeuroP have anti-arrhythmic effects 18 and 14-F 4t -NeuroP was found in edible oils. 19 All reactions requiring anhydrous conditions were conducted in dry glassware (oven 120 °C or flame-dried) with magnetic stirring under an atmosphere of N 2 , unless otherwise mentioned. All anhydrous solvents and reagents were dried following standard methods under a N 2 or argon atmosphere or used as obtained from suppliers (Aldrich, Thermo Fischer).…”

Section: Paper Synthesismentioning

confidence: 99%

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Total Synthesis of DHA and DPAn-3 Non-Enzymatic Oxylipins

Guy¹,

Merad²,

Degrange³

et al. 2021

Synthesis

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Oxylipins are formed in-vivo from polyunsaturated fatty acids (PUFAs). A large structural variety of compounds is grouped under the term oxylipins, which differ from their formation mechanism (involving enzymes or not), as well as their chemical structures (cyclopentanes, tetrahydrofurans, hydroxylated-PUFA etc.). All structures of oxylipins are of great biological interests. Directly correlated to oxidative stress phenomenon, non-enzymatic oxylipins are used as systemic and/or specific biomarkers in various pathologies and more especially, they were found to have their own biological properties. Produced in-vivo as a non-separable mixture of isomers, total synthesis is a keystone to answer biological questions. In this work, we described the total synthesis of three non-enzymatic oxylipins derived from docosahexaenoic acid (DHA) and docosapentanoic acid (DPAn-3) using a unique and convergent synthetic strategy.

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First Total Syntheses of Novel Non‐Enzymatic Polyunsaturated Fatty Acid Metabolites and Their Identification in Edible Oils

Cited by 5 publications

References 27 publications

Chemical Compositional Changes in Over-Oxidized Fish Oils

Chemical Compositional Changes in Over-Oxidized Fish Oils

Isoprostanoids, Isofuranoids and Isoketals – From Synthesis to Lipidomics

Total Synthesis of DHA and DPAn-3 Non-Enzymatic Oxylipins

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