Evaluation of the photooxidation of galactosyl‐ and lactosylceramide by electrospray ionization mass spectrometry

Santinha, Deolinda; Ferreira-Fernandes, Emanuel; Melo, Tânia; Silva, Eduarda M. P.; Maciel, Elisabete; Fardilha, Margarida; Domingues, Pedro; Domingues, M. Rosário M.

doi:10.1002/rcm.7020

Cited by 9 publications

(11 citation statements)

References 40 publications

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“…Sphingolipids, including GluCer and LacCer, are believed to play important roles in signal transduction, cell recognition, cell adhesion, cell growth and protein trafficking [ 4 , 5 , 6 ]. Their involvement in pathogen defense and infection has also been reported [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

“…Their involvement in pathogen defense and infection has also been reported [ 7 ]. Moreover, GluCer, GalCer and LacCer are important components of the neural system and play a role in brain development, in both the fetus and new-born animals including humans [ 6 , 8 , 9 ]. GSLs, together with sphingomyelin, contribute to neonatal cognition [ 10 , 11 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

“…Although GluCer and LacCer are found primarily in cellular membranes [ 6 , 13 , 14 ], they are also present in bovine milk, predominantly in the milk fat globule membrane (MFGM) [ 15 , 16 ]. However, very limited information related to their composition and concentration in both human milk and bovine milk is available.…”

Section: Introductionmentioning

confidence: 99%

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Qualitative and Quantitative Study of Glycosphingolipids in Human Milk and Bovine Milk Using High Performance Liquid Chromatography–Data-Dependent Acquisition–Mass Spectrometry

Fong

MacGibbon

et al. 2020

Molecules

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Cerebrosides (Crb; including glucosylceramide and galactosylceramide) and lactosylceramide (LacCer) are structurally complex lipids found in many eukaryotic cell membranes, where they play important roles in cell growth, apoptosis, cell recognition and signaling. They are also found in mammalian milk as part of the milk fat globule membrane (MFGM), making milk an important dietary component for the rapidly growing infant. This study reports the development of a robust analytical method for the identification and characterization of 44 Crb and 23 LacCer molecular species in milk, using high performance liquid chromatography–tandem mass spectrometry in data-dependent acquisition mode. For the first time, it also compares the distributions of these species in human and bovine milks, a commercial MFGM-enriched dairy ingredient (MFGM Lipid 100) and commercial standards purified from bovine milk. A method for quantifying Crb and LacCer in milk using mass spectrometry in neutral loss scan mode was developed and validated for human milk, bovine milk and MFGM Lipid 100. Human milk was found to contain approximately 9.9–17.4 µg Crb/mL and 1.3–3.0 µg LacCer/mL, whereas bovine milk (pooled milk from a Friesian herd) contained 9.8–12.0 and 14.3–16.2 µg/mL of these lipids, respectively. The process used to produce MFGM Lipid 100 was shown to have enriched these components to 448 and 1036 µg/g, respectively. No significant changes in the concentrations of both Crb and LacCer were observed during lactation.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Qualitative and Quantitative Study of Glycosphingolipids in Human Milk and Bovine Milk Using High Performance Liquid Chromatography–Data-Dependent Acquisition–Mass Spectrometry

Fong

MacGibbon

et al. 2020

Molecules

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“…In mass spectrometric (MS) studies of oxidative stress markers (disease biomarkers), oxidation of some standard glycosphingolipids, containing monoenoic FAs, was induced by a Fenton reaction (H 2 O 2 /FeCl 2 ) or UVA (ultraviolet A) irradiation [6,7]. In particular, Couto et al obtained galactosylceramides with allylic hydroperoxy, hydroxy, or keto groups in FA chains.…”

Section: Introductionmentioning

confidence: 99%

Structural Analysis of Oxidized Cerebrosides from the Extract of Deep-Sea Sponge Aulosaccus sp.: Occurrence of Amide-Linked Allylically Oxygenated Fatty Acids

2020

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The structural elucidation of primary and secondary peroxidation products, formed from complex lipids, is a challenge in lipid analysis. In the present study, rare minor oxidized cerebrosides, isolated from the extract of a far eastern deep-sea glass sponge, Aulosaccus sp., were analyzed as constituents of a multi-component RP-HPLC (high-performance liquid chromatography on reversed-phase column) fraction using NMR (nuclear magnetic resonance) spectroscopy, mass spectrometry, GC (gas chromatography), and chemical transformations (including hydrogenation or derivatization with dimethyl disulfide before hydrolysis). Eighteen previously unknown β-D-glucopyranosyl-(1→1)-ceramides (1a–a//, 1b–b//, 2a–a//, 2b–b//, 3c–c//, 3d–d//) were shown to contain phytosphingosine-type backbones (2S,3S,4R,11Z)-2-aminoeicos-11-ene-1,3,4-triol (in 1), (2S,3S,4R,13Z)-2-aminoeicos-13-ene-1,3,4-triol (in 2), and (13S*,14R*)-2-amino-13,14-methylene-eicosane-1,3,4-triol (in 3). These backbones were N-acylated with straight-chain monoenoic (2R)-2-hydroxy acids that had allylic hydroperoxy/hydroxy/keto groups on C-17/ in the 15/E-23:1 chain (a–a//), C-16/ in the 17/E-23:1 (b–b//) and 14/E-22:1 (c–c//) chains, and C-15/ in the 16/E-22:1 chain (d–d//). Utilizing complementary instrumental and chemical methods allowed for the first detailed structural analysis of a complex mixture of glycosphingolipids, containing allylically oxygenated monoenoic acyl chains.

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“…The known biological impact of these biomolecules has long been the motivation behind understanding their roles in metabolic pathways and oxidative stress related diseases. , Studies on the lipid interactions, metabolism, and trafficking are strongly dependent on the use of chemical tools or probes . Regarding live cell experiments, fluorescence-based techniques are the least invasive, allowing the real-time observation of biological membranes and their characteristic physical properties.…”

Section: Introductionmentioning

confidence: 99%

Emergent Glycerophospholipid Fluorescent Probes: Synthesis and Applications

et al. 2019

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Fluorescent labeling through bioconjugation is the preferred tool for the investigation of biological functions involving lipids, namely for clarifying metabolic pathways and molecular mechanisms of diseases. The lack of functionalized lipid probes with biological and physicochemical properties suitable for these studies is still a major limitation. Moreover, the synthesis of these probes is challenging and strongly dependent on the application envisioned. The objective of this Review is to highlight advances in the application of fluorescent glycerophospholipid probes through innovative approaches in the synthesis reported in the past decade. The reaction pathways, choice of fluorophore, and location of fluorophore in the glycerophospholipid structure are critically addressed. The relevance of these bioconjugates is exemplified with applications using advanced analysis by fluorescence enhancement or quenching to unravel biomembrane structure features and phospholipase activity. Finally, this Review reinforces the need for innovative and more efficient routes for the synthesis of tailored glycerophospholipids fluorescent conjugates.

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Evaluation of the photooxidation of galactosyl‐ and lactosylceramide by electrospray ionization mass spectrometry

Abstract: This study shows that glycosphingolipids are prone to oxidation and the identified mass spectrometry fingerprint of oxidized galactosyl- and lactosylceramide species will support their future identification in lipidomic studies of biological samples under oxidative conditions.

Cited by 9 publications

References 40 publications

Qualitative and Quantitative Study of Glycosphingolipids in Human Milk and Bovine Milk Using High Performance Liquid Chromatography–Data-Dependent Acquisition–Mass Spectrometry

Qualitative and Quantitative Study of Glycosphingolipids in Human Milk and Bovine Milk Using High Performance Liquid Chromatography–Data-Dependent Acquisition–Mass Spectrometry

Structural Analysis of Oxidized Cerebrosides from the Extract of Deep-Sea Sponge Aulosaccus sp.: Occurrence of Amide-Linked Allylically Oxygenated Fatty Acids

Emergent Glycerophospholipid Fluorescent Probes: Synthesis and Applications

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