Characterization of Ceramides with Phytosphingosine Backbone by Hydrogen-deuterium Exchange Mass Spectrometry

Đapić, Irena; Brkljačić, Lidija; Jakaša, Ivone; Kobetić, Renata

doi:10.5562/cca3506

Cited by 5 publications

(4 citation statements)

References 30 publications

(37 reference statements)

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“…The loss of the moiety [H 2 NCHCH 2 OH] + is known for compound ( D ) as the ion at m / z 60.0450 and the base peak according to the HMDB spectral and GNPS database ( Figure S5 ). In addition, the ion [M + H] + at m / z 318.3000 was annotated in the GNPS database ( Figure S6 ) as phytosphingosine ( E ), and the MS/MS experiment yielded major fragments at m / z 282.2780 and 60.0450, which corresponded to di-dehydration and to the fragment [H 2 NCHCH 2 OH] + , as expected for compound ( E ) and experimentally found in the HMDB database [ 42 ].…”

Section: Resultsmentioning

confidence: 70%

Mass Spectrometry Analysis Reveals Lipids Induced by Oxidative Stress in Candida albicans Extracellular Vesicles

et al. 2023

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Candida albicans is a commensal fungus in healthy humans that causes infection in immunocompromised individuals through the secretion of several virulence factors. The successful establishment of infection is owing to elaborate strategies to cope with defensive molecules secreted by the host, including responses toward oxidative stress. Extracellular vesicle (EV) release is considered an alternative to the biomolecule secretory mechanism that favors fungal interactions with the host cells. During candidiasis establishment, the host environment becomes oxidative, and it impacts EV release and cargo. To simulate the host oxidative environment, we added menadione (an oxidative stress inducer) to the culture medium, and we explored C. albicans EV metabolites by metabolomics analysis. This study characterized lipidic molecules transported to an extracellular milieu by C. albicans after menadione exposure. Through Liquid Chromatography coupled with Mass Spectrometry (LC-MS) analyses, we identified biomolecules transported by EVs and supernatant. The identified molecules are related to several biological processes, such as glycerophospholipid and sphingolipid pathways, which may act at different levels by tuning compound production in accordance with cell requirements that favor a myriad of adaptive responses. Taken together, our results provide new insights into the role of EVs in fungal biology and host–pathogen interactions.

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Section: Resultsmentioning

confidence: 70%

Mass Spectrometry Analysis Reveals Lipids Induced by Oxidative Stress in Candida albicans Extracellular Vesicles

et al. 2023

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“…In addition, the fractions of leaves, branches, and roots also showed fragments characteristic of ceramides (positive ion mode), such as m/z 300 (5.55%) and m/z 318 (100%) in MS spectra from leaves, branches, and the root fraction samples, at a retention time of 5.1 min. Dapic and collaborators [37] characterized ceramides using MS analysis in the positive ionization mode and identified abundant ions attributed to phytosphingosine (m/z 282, 300 and 318).…”

Section: Lc-msmentioning

confidence: 99%

Screening for Bioactive Metabolites in Leaves, Branches, and Roots of Mansoa hirsuta: Phytochemical, Toxicological and Antioxidant Aspects

et al. 2023

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In this study, secondary metabolites, toxicology and antioxidant properties of chloroform fractions from leaves (FCFMh), branches (FCGMh), and roots (FCRMh) of Mansoa hirsuta were investigated. The phytochemical screening detected flavonoids, especially chalcones. Through Liquid chromatography with mass spectrometry—LC–MS analysis, the flavonoids (isoorientin-2″-O-arabinoside), triterpenes (oleanolic acid and ursolic acid) and ceramide (phytosphingosine) were identified. From the Artemia salina assay, the fraction FCGMh was the most toxic (LC50 = 64.21 µg·mL−1), followed by FCRMh (LC50 = 87.61 µg·mL−1) and FCFMh (LC50 = 421.9 µg·mL−1). Concerning the cytotoxic potential, the root fraction (IC50 16.48 μg mL−1) displayed the highest cytotoxicity against the breast cancer cell line (4T1), followed by leaves (IC50 33.13 μg mL−1) and branches (IC50 of 47.13 μg mL−1). In conclusion, all the fractions of M. hirsuta showed cytotoxicity at the highest concentrations; however, remarkable biological properties were found for the root fractions. Computational analysis was performed using a molecular docking and pharmacophore approach to understand the antioxidant activity of its major metabolites.

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“…Therefore, metabolites selected by the Boruta algorithm were identified by their high-resolution mass, MS/MS spectra, and comparison of CCS values with the LipidCCS database (see Table S4 in the Supplementary Materials) [34]. The fragmentation pattern of the discussed substance classes is also explained in the Supplementary Materials [39][40][41][42][43][44][45][46][47]. As mentioned above, the differences induced by storage at high temperature and humidity (ST1; 40 • C; 75% rel.…”

Section: Analysis and Comparison Of Storage-induced Changes In The Me...mentioning

confidence: 99%

Food Monitoring: Limitations of Accelerated Storage to Predict Molecular Changes in Hazelnuts (Corylus avellana L.) under Realistic Conditions Using UPLC-ESI-IM-QTOF-MS

Loesel,

Shakiba,

Wenck

et al. 2023

Metabolites

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Accelerated storage is routinely used with pharmaceuticals to predict stability and degradation patterns over time. The aim of this is to assess the shelf life and quality under harsher conditions, providing crucial insights into their long-term stability and potential storage issues. This study explores the potential of transferring this approach to food matrices for shelf-life estimation. Therefore, hazelnuts were stored under accelerated short-term and realistic long-term conditions. Subsequently, they were analyzed with high resolution mass spectrometry, focusing on the lipid profile. LC-MS analysis has shown that many unique processes take place under accelerated conditions that do not occur or occur much more slowly under realistic conditions. This mainly involved the degradation of membrane lipids such as phospholipids, ceramides, and digalactosyldiacylglycerides, while oxidation processes occurred at different rates in both conditions. It can be concluded that a food matrix is far too complex and heterogeneous compared to pharmaceuticals, so that many more processes take place during accelerated storage, which is why the results cannot be used to predict molecular changes in hazelnuts stored under realistic conditions.

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Characterization of Ceramides with Phytosphingosine Backbone by Hydrogen-deuterium Exchange Mass Spectrometry

Cited by 5 publications

References 30 publications

Mass Spectrometry Analysis Reveals Lipids Induced by Oxidative Stress in Candida albicans Extracellular Vesicles

Mass Spectrometry Analysis Reveals Lipids Induced by Oxidative Stress in Candida albicans Extracellular Vesicles

Screening for Bioactive Metabolites in Leaves, Branches, and Roots of Mansoa hirsuta: Phytochemical, Toxicological and Antioxidant Aspects

Food Monitoring: Limitations of Accelerated Storage to Predict Molecular Changes in Hazelnuts (Corylus avellana L.) under Realistic Conditions Using UPLC-ESI-IM-QTOF-MS

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