Stable analogs of 13‑hydroxy-9,10-trans-epoxy-(11E)-octadecenoate (13,9-HEL), an oxidized derivative of linoleic acid implicated in the epidermal skin barrier

Keyes, Gregory S.; Maiden, Kristen; Ramsden, Christopher E.

doi:10.1016/j.plefa.2021.102357

Cited by 6 publications

(3 citation statements)

References 39 publications

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“…Nevertheless, the formation paths of both kinds of compounds have in common that the higher the enrichment in HTy-Ac, the later their formation begins, the lower the concentration reached, and both reach their maximum concentration just after the total HTy-Ac degradation, furthermore, as shown in Figures 8b and 7b, both are intermediate compounds. In short, sunflower oil HTy-Ac enrichment delays and reduces the formation of these compounds, which have recently been related with the activation of trigeminal neurons [78] and with the epidermal skin barrier [79].…”

Section: Effect Of the Sunflower Oil Enrichment In Hty-ac On The Form...mentioning

confidence: 98%

Influence of Hydroxytyrosol Acetate Enrichment of an Oil Rich in Omega-6 Groups on the Evolution of Its Oxidation and Oxylipin Formation When Subjected to Accelerated Storage. A Global Study by Proton Nuclear Magnetic Resonance

2022

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Sunflower oil samples, both unenriched and enriched with four different concentrations of hydroxytyrosol acetate, were subjected to accelerated storage at 70 °C until a very advanced oxidation stage and the process was monitored by 1H NMR spectroscopy. The aim of the study is to know the effect that the presence of this antioxidant has on the oxidation process of sunflower oil under the aforementioned conditions, as well as on the formation and evolution of the concentration of a significant number of oxylipins. The oxidation process was studied globally by monitoring, during storage time, the degradation of both the linoleic acyl group of sunflower oil, which is the main component of sunflower oil, and the added hydroxytyrosol acetate. Simultaneously, the identification of up to twenty-six different types of oxylipins formed in the oxidation process and the monitoring of the evolution of their concentration over the storage time were carried out. In this way, essential information about the effect that hydroxytyrosol acetate provokes on the oxidation of this oil rich in omega-6 polyunsaturated acyl groups, has been obtained. It has also been shown that the enrichment of sunflower oil with this antioxidant under the conditions tested does not prevent the oxidation process but slows it down, affecting the entire oxidation process.

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Section: Effect Of the Sunflower Oil Enrichment In Hty-ac On The Form...mentioning

confidence: 98%

Influence of Hydroxytyrosol Acetate Enrichment of an Oil Rich in Omega-6 Groups on the Evolution of Its Oxidation and Oxylipin Formation When Subjected to Accelerated Storage. A Global Study by Proton Nuclear Magnetic Resonance

2022

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“…And the effect of sunflower oil enrichment in αT, HTy-Ac and binary mixtures of αT and HTy-Ac on the onset of their formation and on the evolution of their concentration will be analysed in each group. In addition, it should be remembered that harmful effects on human health have been attributed to some of these compounds [ 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 ], so the influence that the enrichment of the oil in αT, HTy-Ac and binary mixtures of them has on the formation of these compounds is a subject of great interest.…”

Section: Resultsmentioning

confidence: 99%

Individual and Joint Effect of Alpha-Tocopherol and Hydroxytyrosol Acetate on the Oxidation of Sunflower Oil Submitted to Oxidative Conditions: A Study by Proton Nuclear Magnetic Resonance

2022

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This study tackles the individual and joint effect of alpha-tocopherol and hydroxytyrosol acetate on the oxidation of sunflower oil submitted to accelerated storage conditions at intermediate temperature, in order to deepen the understanding of antioxidant–prooxidant behaviour. This was accomplished by 1H Nuclear Magnetic Resonance. For this purpose, the evolution of the degradation of both the main components of the oil and the aforementioned added compounds was monitored by this technique throughout the storage time. Furthermore, the formation of a very large number of oxylipins and the evolution of their concentration up to a very advanced stage of oil oxidation, as well as the occurrence of lipolysis, were also simultaneously studied. The results obtained show very clearly and thoroughly that in the oxidation process of the oil enriched in binary mixtures, interactions occur between alpha-tocopherol and hydroxytyrosol acetate that notably reduce the antioxidant effect of the latter compound with the corresponding negative consequences that this entails. The methodology used here has proved to be very efficient to evaluate the antioxidant power of mixtures of compounds.

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“…Epidermal linoleic acid derived mono-, di- and tri-ols and epoxides [e.g. HODE; dihydroxyoctadecenoic acid (DiHOME), epoxyoctadecenoic (EpOME)] have been implicated in barrier function [25 ▪▪ ,32], although the exact role of the recently identified ethanolamine 13-HODE-ethanolamine (13-HODE-EA) is not yet known [33].…”

Section: Lipids Have Different Roles Throughout the Skinmentioning

confidence: 99%

Current insights into skin lipids and their roles in cutaneous health and disease

Nicolaou

Kendall²

2022

Current Opinion in Clinical Nutrition &Amp; Metabolic Care

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Purpose of reviewThe unique and complex array of cutaneous lipids include essential components of the skin structure and signalling molecules mediating homeostasis and inflammation. Understanding skin lipid biology and metabolism can support our comprehension of health and disease, including systemic conditions with cutaneous involvement.Recent findingsLipids found on the skin surface, produced by both the host and resident microbes, maintain and regulate the skin microbiome and the epidermal barrier, whilst altered contributions from either source can be detrimental to skin health. The unique lipid composition of the epidermal barrier is essential for its function, and recent studies have expanded our understanding of epidermal ceramide production. This has been supported by improved models available for skin research, including organotypic skin models enabling in-vitro production of complex acylceramides for the first time, and model systems facilitating in-silico exploration of the lipid profile changes observed in clinical samples. Studies have revealed further involvement of lipid mediators such as eicosanoids in cutaneous inflammation, as well as immune regulation in both healthy and diseased skin.SummarySkin lipids offer exciting opportunities as therapeutic targets for many conditions, whether through topical interventions or nutritional supplementation.

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Stable analogs of 13‑hydroxy-9,10-trans-epoxy-(11E)-octadecenoate (13,9-HEL), an oxidized derivative of linoleic acid implicated in the epidermal skin barrier

Cited by 6 publications

References 39 publications

Influence of Hydroxytyrosol Acetate Enrichment of an Oil Rich in Omega-6 Groups on the Evolution of Its Oxidation and Oxylipin Formation When Subjected to Accelerated Storage. A Global Study by Proton Nuclear Magnetic Resonance

Influence of Hydroxytyrosol Acetate Enrichment of an Oil Rich in Omega-6 Groups on the Evolution of Its Oxidation and Oxylipin Formation When Subjected to Accelerated Storage. A Global Study by Proton Nuclear Magnetic Resonance

Individual and Joint Effect of Alpha-Tocopherol and Hydroxytyrosol Acetate on the Oxidation of Sunflower Oil Submitted to Oxidative Conditions: A Study by Proton Nuclear Magnetic Resonance

Current insights into skin lipids and their roles in cutaneous health and disease

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