Structural determination of hexadecanoic lysophosphatidylcholine regioisomers by fast atom bombardment tandem mass spectrometry

Hong, Jongki; Kim, Young Hwan; Gil, Ji Hye; Cho, Kun; Jung, Jee H.; Han, Sang M.

doi:10.1002/rcm.835

Cited by 10 publications

(5 citation statements)

References 10 publications

(12 reference statements)

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“…Mass spectrometry (MS) is known to be an important analytical tool for the structural studies of compounds extracted from trace amounts of biological samples. The structures of lipids have been elucidated by various MS ionization methods including chemical ionization (CI),6 fast‐atom bombardment (FAB),7, 8 electrospray ionization (ESI),9–11 atmospheric pressure chemical ionization (APCI),12 and matrix‐assisted laser desorption/ionization (MALDI) 13…”

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confidence: 99%

Structural determination of cyclitol derivatives by fast‐atom bombardment tandem mass spectrometry

Gil

Seo

Kim

et al. 2006

Rapid Comm Mass Spectrometry

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Three cyclitol derivatives were isolated from the marine sponge Sarcotragus sp. by reversed-phase high-performance liquid chromatography and analyzed by fast-atom bombardment mass spectrometry (FAB-MS). Their structural elucidation was carried out with FAB tandem mass spectrometry (FAB-MS/MS). FAB-MS spectra produced a significant abundance of the sodium adducts [M+Na]+ and [M+2Na-H]+ from a mixture of m-NBA and NaI. In addition, trifluoroacetylation of the cyclitol derivatives was used for confirmation of the presence of the cyclitol ring. High abundance [M-5H+5CF3CO+Na]+ ions were observed in the FAB-MS spectra of the trifluoroacetyl-cyclitol derivatives. Collision-induced dissociation (CID) of the [M+Na]+ ions produced diverse product ions via a series of dissociative processes. Charge-remote fragmentation (CRF) patterns of [M+Na]+ ions were very useful for the identification of product ions which are characteristic for the cyclitol ring and long hydrocarbon chains substituted at the glycerol backbone. Moreover, the CID-MS/MS spectra of the [M+Na]+ ions yielded characteristic product ions at m/z 53, 83, 113, 155 and 171 for the cyclitol moiety, and at m/z 213, 229 and 245 for the glycerol backbone attached to the cyclitol ring.

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confidence: 99%

Structural determination of cyclitol derivatives by fast‐atom bombardment tandem mass spectrometry

Gil

Seo

Kim

et al. 2006

Rapid Comm Mass Spectrometry

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“…CRF results in parallel losses of C n H 2 n +2 units along the hydrocarbon chain via 1,4‐H 2 elimination28, 29, 32 or a charge‐driven process33, 34 beginning at the alkyl and acyl terminus, respectively. The pattern of these ions immediately gives information regarding the presence and location of the double bond and the branching point as well as the composition of acyl groups 35. We previously reported36, 37 on structural information of various lipid compounds having similar repetitive groups that the required information is readily obtained from the CRF ions produced by FAB‐linked scan at constant B/E.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, a doublet of ions at m / z 347 and 348 indicating CRF and CDF process at allylic position, respectively, is observed in the CID spectrum. The peaks at m / z 307, 321 and 335 between m / z 293 and 347 exhibit a relatively low intensity due to suppressed CRF dissociation in the vicinity of double bond 35, 38. From these dissociation patterns, the position of the double bond can be assigned at C17.…”

Section: Resultsmentioning

confidence: 99%

Structural determination of glucosylceramides isolated from marine sponge by fast atom bombardment collision‐induced dissociation linked scan at constant B/E

et al. 2009

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Five glucosylceramides (GlcCers) were isolated by reversed phase high-performance liquid chromatography from the MeOH extracts of a marine sponge, Haliclona (Reniera) sp., collected from the coast of Ulleung Island, Korea, and analyzed by fast atom bombardment mass spectrometry (FAB-MS) in positive-ion mode. FAB-mass spectra of these compounds included protonated molecules [M + H](+) and abundant sodiated molecules [M + Na](+) from a mixture of m-NBA and NaI. The structures of these GlcCers, which were similar, were elucidated by FAB-linked scan at constant B/E. To find diagnostic ions for their characterization, the GlcCers were analyzed by collision-induced dissociation (CID) linked scan at constant B/E. The CID-linked scan at constant B/E of [M + H](+) and [M + Na](+) precursor ions resulted in the formation of numerous characteristic product ions via a series of dissociative processes. The product ions formed by charge-remote fragmentation provided important information for the characterization of the fatty N-acyl chain moiety and the sphingoid base, commonly referred to as the long-chain base. The product ions at m/z 203 and 502 were diagnostic for the presence of a sodiated sugar ring and beta-D-glucosylsphinganine, respectively. For further confirmation of the structure of the fatty N-acyl chain moiety in each GlcCer, fatty acid methyl esters were obtained from the five GlcCers by methanolysis and analyzed by FAB-MS in positive-ion mode. On the basis of these dissociation patterns, the structures of the five GlcCers from marine sponge were elucidated. In addition, the accurate mass measurement was performed to obtain the elemental composition of the GlcCers isolated from marine sponge.

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“…NACE-MS has shown applicability in underivatized fatty acids (Azab et al, 2019), as well as phospholipids (Gao et al, 2007). FAB-MS is widely used to identify the structure of nonvolatile and high-molecular-weight lipids, such as glycerolipids (Gil et al, 2007), monogylcerides (Gil et al, 2007), glycerophospholipids (Hong et al, 2002), sphingomyelins (Ahn et al, 2009), and simple fatty acids (Ji et al, 2007). APCI-MS and APPI-MS have also been developed for lipidomic analysis (Li et al, 2014).…”

Section: Ms In Lipid Analysismentioning

confidence: 99%

Mass spectrometric approaches in discovering lipid biomarkers for COVID‐19 by lipidomics: Future challenges and perspectives

Gowda

Shekhar

Gowda

et al. 2023

Mass Spectrometry Reviews

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Coronavirus disease 2019 (COVID‐19) has emerged as a global health threat and has rapidly spread worldwide. Significant changes in the lipid profile before and after COVID‐19 confirmed the significance of lipid metabolism in regulating the response to viral infection. Therefore, understanding the role of lipid metabolism may facilitate the development of new therapeutics for COVID‐19. Owing to their high sensitivity and accuracy, mass spectrometry (MS)‐based methods are widely used for rapidly identifying and quantifying of thousands of lipid species present in a small amount of sample. To enhance the capabilities of MS for the qualitative and quantitative analysis of lipids, different platforms have been combined to cover a wide range of lipidomes with high sensitivity, specificity, and accuracy. Currently, MS‐based technologies are being established as efficient methods for discovering potential diagnostic biomarkers for COVID‐19 and related diseases. As the lipidome of the host cell is drastically affected by the viral replication process, investigating lipid profile alterations in patients with COVID‐19 and targeting lipid metabolism pathways are considered to be crucial steps in host‐directed drug targeting to develop better therapeutic strategies. This review summarizes various MS‐based strategies that have been developed for lipidomic analyzes and biomarker discoveries to combat COVID‐19 by integrating various other potential approaches using different human samples. Furthermore, this review discusses the challenges in using MS technologies and future perspectives in terms of drug discovery and diagnosis of COVID‐19.

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Structural determination of hexadecanoic lysophosphatidylcholine regioisomers by fast atom bombardment tandem mass spectrometry

Cited by 10 publications

References 10 publications

Structural determination of cyclitol derivatives by fast‐atom bombardment tandem mass spectrometry

Structural determination of cyclitol derivatives by fast‐atom bombardment tandem mass spectrometry

Structural determination of glucosylceramides isolated from marine sponge by fast atom bombardment collision‐induced dissociation linked scan at constant B/E

Mass spectrometric approaches in discovering lipid biomarkers for COVID‐19 by lipidomics: Future challenges and perspectives

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