Fragmentation Behavior and Gas-Phase Structures of Cationized Glycosphingolipids in Ozone-Induced Dissociation Mass Spectrometry

Barrientos, Rodell C.; Zhang, Qibin

doi:10.1007/s13361-019-02267-7

Cited by 12 publications

(10 citation statements)

References 55 publications

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“…The differential reactivity of the long-chain base double bond and the fatty acyl double bond was very useful in assigning which acyl chain contains the double bond. We also found that the OzID fragmentation behavior of glycosphingolipids could be dictated by the adduct type: [M +Li] + and [M+Na] + fragment mainly at the double bond position; [M+H] + undergoes dehydration followed by CID-like loss of the glycan head group [176].…”

Section: Ozone-induced Dissociationmentioning

confidence: 81%

Recent advances in the mass spectrometric analysis of glycosphingolipidome – A review

Barrientos

Zhang

2020

Analytica Chimica Acta

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Aberrant expression of glycosphingolipids has been implicated in a myriad of diseases, but our understanding of the strucural diversity, spatial distribution, and biological function of this class of biomolecules remains limited. These challenges partly stem from a lack of sensitive tools that can detect, identify, and quantify glycosphingolipids at the molecular level. Mass spectrometry has emerged as a powerful tool poised to address most of these challenges. Here, we review the recent developments in analytical glycosphingolipidomics with an emphasis on sample preparation, mass spectrometry and tandem mass spectrometry-based structural characterization, label-free and labeling-based quantification. We also discuss the nomenclature of glycosphingolipids, and emerging technologies like ion mobility spectrometry in differentiation of glycosphingolipid isomers. The intrinsic advantages and shortcomings of each method are carefully critiqued in line with an individual's research goals. Finally, future perspectives on analytical sphingolipidomics are stated, including a need for novel and more sensive methods in isomer separation, low abundance species detection, and profiling the spatial distribution of glycosphingolipid molecular species in cells and tissues using imaging mass spectrometry.

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Section: Ozone-induced Dissociationmentioning

confidence: 81%

Recent advances in the mass spectrometric analysis of glycosphingolipidome – A review

Barrientos

Zhang

2020

Analytica Chimica Acta

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“…The OzID-MS technique was tested on the fungal metabolites ent -sartorypyrone E ( 1 ), sartorypyrone A ( 2 ), sorbicillin ( 3 ), , trichodermic acid A ( 4 ), and AA03390 ( 5 ), where the observed accurate masses corresponding to the carbonyl/Criegee product ions confirmed the placement of double bonds in these molecules. Infusion of sodium acetate into the mass spectrometry system (see Experimental Section) was used to increase the abundance of sodiated adducts, which increase the efficiency of ozonolysis in the OzID-MS experiment. ,, …”

Section: Resultsmentioning

confidence: 99%

“…While this was slightly different than what was observed with 1 , since C-12 was not cleaved, we were not surprised by these results. OzID-MS is known to be a charged-induced reaction, and as such, the distance and interaction between where the sodium adduct was formed, relative to the double bond, can hinder the efficiency of ozonolysis . An example of this phenomenon is sphingomyelin, where OzID-MS was able to characterize the double bonds in the fatty acyl chains, but not the double bond on the long chain base .…”

Section: Resultsmentioning

confidence: 99%

“…Infusion of sodium acetate into the mass spectrometry system (see Experimental Section) was used to increase the abundance of sodiated adducts, which increase the efficiency of ozonolysis in the OzID-MS experiment. (37,47,66) When performing OzID-MS on compound 1, the sodium ion can associate with the hydroxy moieties at the end of the isoprene chain (left side of molecule) or the oxygens in the lactone ring (right side of molecule), which is why all the theoretically possible carbonyl and Criegee ions were observed from both ends of the molecule. Regardless of where sodium associated with 1 (i.e., [M + Na] + ), the targeted precursor ion was observed at m/z 455.2772.…”

Section: Analysis Of Double-bond Positions In Pure Compounds By Ozid-msmentioning

confidence: 99%

“…OzID-MS is known to be a charged-induced reaction, and as such, the distance and interaction between where the sodium adduct was formed, relative to the double bond, can hinder the efficiency of ozonolysis. (66) An example of this phenomenon is sphingomyelin, where OzID-MS was able to characterize the double bonds in the fatty acyl chains, but not the double bond on the long chain base. (67) This is an important distinction for OzID-MS, as the distance of the double bond(s) from where the sodium associates to form the adduct is important.…”

Section: Analysis Of Double-bond Positions In Pure Compounds By Ozid-msmentioning

confidence: 99%

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Orthogonal Method for Double-Bond Placement via Ozone-Induced Dissociation Mass Spectrometry (OzID-MS)

Knowles

Todd

et al. 2019

J. Nat. Prod.

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Most often, the structures of secondary metabolites are solved using a suite of NMR techniques. However, there are times when it can be challenging to position double bonds, particularly those that are fully substituted or when there are multiple double bonds in similar chemical environments. Ozone-induced dissociation mass spectrometry (OzID-MS) serves as an orthogonal structure elucidation tool, using predictable fragmentation patterns that are generated after ozonolysis across a carbon-carbon double bond. This technique is finding growing use in the lipidomics community, suggestive of its potential value for secondary metabolites. This methodology was evaluated by confirming the double-bond positions in five fungal secondary metabolites, specifically, ent-sartorypyrone E (1), sartorypyrone A (2), sorbicillin (3), trichodermic acid A (4), and AA03390 (5). This demonstrated its potential with a variety of chemotypes, ranging from polyketides to terpenoids and including those in both conjugated and nonconjugated polyenes. In addition, the potential of using this methodology in the context of a mixture was piloted by studying Aspergillus fischeri, first examining a traditional extract and then sampling a live fungal culture in situ. While the intensity of signals varied from pure compound to extract to in situ, the utility of the technique was preserved.

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Structural Characterization of Lipids Using Advanced Mass Spectrometry Approaches

Cvačka¹,

Vrkoslav²,

Strnad³

2023

Mass Spectrometry for Lipidomics

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Fragmentation Behavior and Gas-Phase Structures of Cationized Glycosphingolipids in Ozone-Induced Dissociation Mass Spectrometry

Cited by 12 publications

References 55 publications

Recent advances in the mass spectrometric analysis of glycosphingolipidome – A review

Recent advances in the mass spectrometric analysis of glycosphingolipidome – A review

Orthogonal Method for Double-Bond Placement via Ozone-Induced Dissociation Mass Spectrometry (OzID-MS)

Structural Characterization of Lipids Using Advanced Mass Spectrometry Approaches

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