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Antioxidative Effect of Dihydrosphingosine (d18:0) and α-Tocopherol on Tridocosahexaenoin (DHA-TAG).

ABSTRACT: Sphingoid bases have shown promise as effective antioxidants in fish oils together with α-tocopherol, and the effect has been attributed to products resulting from amino-carbonyl reactions (lipation products) between the sphingoid base amine group and carbonyl compounds from lipid oxidation. In this study, the synergistic effect of dihydrosphingosine (d18:0) and α-tocopherol was studied on pure docosahexaenoic acid (DHA) triacylglycerols with an omics-type liquid- and gas-chromatographic mass spectrometric approach to verify the synergistic effect, to get a comprehensive view on the effect of d18:0 on the oxidation pattern, and to identify the lipation products. The results confirmed that d18:0 rapidly reacts further in the presence of lipid oxidation products and α-tocopherol. α-Tocopherol and d18:0 showed an improved antioxidative effect after 12 h of oxidation, indicating the formation of antioxidants through carbonyl-amine reactions. Imines formed from the carbonyls and d18:0 could be tentatively identified.

SUBMITTER: Ahonen E

PROVIDER: S-EPMC10571079 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Antioxidative Effect of Dihydrosphingosine (d18:0) and α-Tocopherol on Tridocosahexaenoin (DHA-TAG).

Ahonen Eija E Damerau Annelie A Linderborg Kaisa M KM

Journal of agricultural and food chemistry 20230926 40

Sphingoid bases have shown promise as effective antioxidants in fish oils together with α-tocopherol, and the effect has been attributed to products resulting from amino-carbonyl reactions (lipation products) between the sphingoid base amine group and carbonyl compounds from lipid oxidation. In this study, the synergistic effect of dihydrosphingosine (d18:0) and α-tocopherol was studied on pure docosahexaenoic acid (DHA) triacylglycerols with an omics-type liquid- and gas-chromatographic mass sp ...[more]

PMID: 37751317

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Project description:Background/objectivesThe role of vitamin E in chronic disease risk remains incompletely understood, particularly in an un-supplemented state, and evidence is sparse regarding the biological actions and pathways involved in its influence on health outcomes. Identifying vitamin-E-associated metabolites through agnostic metabolomics analyses can contribute to elucidating the specific associations and disease etiology. This study aims to investigate the association between circulating metabolites and serum α-tocopherol concentration in an un-supplemented state.Subjects/methodsMetabolomic analysis of 4,294 male participants was conducted based on pre-supplementation fasting serum in the Alpha-Tocopherol, Beta-Carotene Cancer Prevention Study. The associations between 1,791 known metabolites measured by ultra-high-performance LC-MS/GC-MS and HPLC-determined α-tocopherol concentration were estimated using multivariable linear regression. Differences in metabolite levels per unit difference in α-tocopherol concentration were calculated as standardized β-coefficients and standard errors.ResultsA total of 252 metabolites were associated with serum α-tocopherol at the Bonferroni-corrected p value (p < 2.79 × 10-5). Most of these metabolites were of lipid and amino acid origin, with the respective subclasses of dicarboxylic fatty acids, and valine, leucine, and isoleucine metabolism, being highly represented. Among lipids, the strongest signals were observed for linoleoyl-arachidonoyl-glycerol (18:2/20:4)[2](β = 0.149; p = 8.65 × 10-146) and sphingomyelin (D18:2/18:1) (β = 0.035; p = 1.36 × 10-30). For amino acids, the strongest signals were aminoadipic acid (β = 0.021; p = 5.01 × 10-13) and l-leucine (β = 0.007; p = 1.05 × 10-12).ConclusionsThe large number of metabolites, particularly lipid and amino acid compounds associated with serum α-tocopherol provide leads regarding potential mechanisms through which vitamin E influences human health, including its role in cardiovascular disease and cancer.

Project description:Placental villi play pivotal roles in feto-maternal transportation and phospholipids constitute a major part of the villous membrane. We have been developing and optimizing an imaging system based on a matrix-assisted laser desorption/ionization (MALDI)-based mass spectrometer, which provides clear two-dimensional molecular distribution patterns using highly sensitive mass spectrometry from mixtures of ions generated on tissue surfaces. We recently applied this technology to normal human uncomplicated term placentas and detected the specific distribution of sphingomyelin (SM) (d18:1/16:0) in stem villi and phosphatidylcholine (PC) (16:0/20:4) in terminal villi. In the present study, we applied this technology to nine placentas with maternal or fetal complications, and determined whether a relationship existed between these specific distribution patterns of phospholipid molecules and the six representative pathological findings of placentas, i.e., villitis of unknown etiology (VUE), thrombus, atherosis, chorioamnionitis (CAM), immature terminal villi, and multiple branched terminal villi. In two placentas with the first and second largest total number of positive pathological findings, i.e., five and three positive findings, the specific distribution of SM (d18:1/16:0) in stem villi and PC (16:0/20:4) in terminal villi disappeared. The common pathological findings in these two placentas were atherosis, immature terminal villi, and multiple branched terminal villi, suggesting the possible involvement of the underperfusion of maternal blood into the intervillous space. On the other hand, the number of pathological findings were two or less in the seven other placentas, in which no specific relationships were observed between the differential expression patterns of these two phospholipids in stem and terminal villi and the pathological findings of the placentas; however, the specific distribution pattern of SM (d18:1/16:0) in stem villi disappeared in four placentas, while that of PC (16:0/20:4) in terminal villi was preserved. These results suggested that the absence of the specific distribution of PC (16:0/20:4) in terminal villi, possibly in combination with the absence of SM (d18:1/16:0) in stem villi, was linked to placental morphological changes in response to maternal underperfusion of the placenta.

Dataset Information

Antioxidative Effect of Dihydrosphingosine (d18:0) and α-Tocopherol on Tridocosahexaenoin (DHA-TAG).

Publications

Antioxidative Effect of Dihydrosphingosine (d18:0) and α-Tocopherol on Tridocosahexaenoin (DHA-TAG).

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