Tandem mass spectrometric analysis of fatty acyl groups of galactolipid molecular species from wheat flour

Kim, Young Hwan; Gil, Ji Hye; Hong, Jongki; Yoo, Jong Shin

doi:10.1016/s0026-265x(00)00141-7

Cited by 30 publications

(12 citation statements)

References 17 publications

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“…As shown in Fig. 1a, the fragmentation pattern observed in CID-MS/MS of compound 1 was very similar to that of the MGDG investigated in our previous work [8]. The fragmentation pathways and labeled product ions are also illustrated in Fig.…”

Section: Resultssupporting

confidence: 81%

“…As mentioned in a previous study, high-energy CID of the sodium-adducted molecular ions ([M + Na] + ) of glycosyl diacylglycerol enabled the complete structural analysis of the fatty acyl residues and the head group [6][7][8]. In particular, fragmentation along the hydrocarbon chains remote from the charge site allowed the determination of the position of the double-bond in the polyunsaturated fatty acyl groups.…”

Section: Resultsmentioning

confidence: 95%

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Two New Monogalactosyl Diacylglycerols from Brown Alga Sargassum thunbergii

Kim

Lee

et al. 2007

Lipids

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Two new monogalactosyl diacylglycerols (MGDGs) along with two known glycolipids were isolated from the moderate polar fraction of the methanolic extract of the brown alga Sargassum thunbergii by using reversed silica flash chromatography. Two new MGDGs were identified as (2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactopyranosyl-sn-glycerol (1) and (2S)-1-O-(9Z,12Z,15Z-octadecatrienoyl)-2-O-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-3-O-beta-D-galactopyranosyl-sn-glycerol (2) by FAB tandem mass spectrometry, NMR techniques, and specific enzyme-catalyzed hydrolysis of the sn-1 fatty acyl linkage. The regiochemical attachment of the acyl chains in the glycerol moiety was established by 2D NMR correlations and confirmed by enzymatic hydrolysis.

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Section: Resultssupporting

confidence: 81%

Section: Resultsmentioning

confidence: 95%

Two New Monogalactosyl Diacylglycerols from Brown Alga Sargassum thunbergii

Kim

Lee

et al. 2007

Lipids

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“…4(a)) displays the [M–H] − ion at m/z 795, and skimmer CAD fragmentation yields two major series ions: (i) B x as the fatty carboxylate anions [R x CO 2 ] − at m/z 275 and 301, and (ii) C x ions from neutral loss of ketenes [MHR′ x CHCO] − at m/z 511 and 537, where R x = R′ x CH 2 . Although similar fragments have previously been reported from FAB‐CID‐MS/MS experiments,17 the greater sensitivity and the better structural determination capabilities of our LC/MS methodology, allowing direct identification of the molecular species without previous isolation of pure compounds, are significant improvements.…”

Section: Resultssupporting

confidence: 53%

“…Two mass spectrometric methods, fast atom bombardment with tandem mass spectrometry (FAB‐MS/MS)17 and another approach involving flow‐injection ESI‐MS/MS spectra of [M+K] + ions,18 have recently been claimed to be adequate for the targeted structural determination in pure galactolipids and glucolipids, respectively; however, in our opinion, they are not reliable techniques for mixture analysis and, in any event, the reported data18 do not appear to provide a clear‐cut solution to the problem of interest here.…”

Section: Methodsmentioning

confidence: 99%

A new solution for an old problem: the regiochemical distribution of the acyl chains in galactolipids can be established by electrospray ionization tandem mass spectrometry

Guella

Frassanito

Mancini

2003

Rapid Comm Mass Spectrometry

131

122

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Electrospray ionization-quadrupole ion trap mass spectrometry (ESI-QITMS), either in positive- or in negative-ion mode, has been used to establish the chemical structures (chain length, degree of unsaturation, positional distribution) of the fatty acids attached to the primary (sn-1) and secondary (sn-2) hydroxyl groups of the glycerol moiety of natural monogalactosyl- (MGDG) and digalactosyldiacylglycerols (DGDG), isolated from the freshwater dinoflagellate Glenodinium sanguineum and from a marine diatom belonging to the genus Chaetoceros. Fragmentation by collision-induced dissociation of a single component in MGDG and DGDG mixtures, separated by high-performance liquid chromatography (HPLC) and detected on-line by tandem positive-ion ESI-MS, leads to a clear-cut determination of the positional distribution of the sn-glycerol-bound fatty acyl chains. Reversed-phase liquid chromatography allowed a partial resolution of the component mixture before ESI-MS/MS analysis. These results were validated by comparison with ESI-MS data obtained for the sn-2 lysoglyceroglycolipids synthesized via regiospecific enzymatic hydrolysis of the corresponding diacylglycerols by Rhizopus arrhizus lipase.

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“…Furthermore, linoleic acid (C18:2) or linolenic acid (C18:3) losses resulted in fragments of [M-RCOOH+Na] + at m/z 519.2949 and 521.3074, respectively. Due to the fatty acid in the sn -2 position of MGDG being more favorable to lose than sn -1 [ 42 ] and the abundance of 519 m/z was higher than 521 m/z, the distribution of fatty acids for MGDG (18:3/18:2) could be determined.…”

Section: Resultsmentioning

confidence: 99%

Lipid Compositions and Geographical Discrimination of 94 Geographically Authentic Wheat Samples Based on UPLC-MS with Non-Targeted Lipidomic Approach

Jin

Zheng

Zhang

et al. 2020

Foods

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Wheat is the staple food for the world’s major populations. However, chemical characters of geographically authentic wheat samples, especially for the lipids, have not been deeply studied. The present research aimed to investigate lipid compositions of Chinese wheat samples and clarify the major markers that contribute to the geographical differences. A total of 94 wheat samples from eight main wheat-producing provinces in China were evaluated to differentiate their lipid compositions. Based on the data collected from ultra-high-performance-liquid-chromatography tandem time-of-flight mass spectrometry (UPLC-Q/TOF MS), an optimized non-targeted lipidomic method was utilized for analyses. As the results, 62 lipid compounds, including fatty acids, phospholipids, galactolipids, triglycerides, diglycerides, alkylresorcinol, and ceramide were tentatively identified. Partial least squares discriminant analysis (PLS-DA) demonstrated a more satisfying performance in distinguishing wheat samples from different origins compared with principal component analysis (PCA). Further, the abundances of triglycerides and glycerophospholipids with more unsaturated fatty acids were found greater in wheat samples from northern origins of China, while more glycolipids and unsaturated fatty acids arose in southern original wheat samples. These findings describe the lipid profiles of wheat samples in China and could contribute to the quality and safety control for the wheat flour products.

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Tandem mass spectrometric analysis of fatty acyl groups of galactolipid molecular species from wheat flour

Cited by 30 publications

References 17 publications

Two New Monogalactosyl Diacylglycerols from Brown Alga Sargassum thunbergii

Two New Monogalactosyl Diacylglycerols from Brown Alga Sargassum thunbergii

A new solution for an old problem: the regiochemical distribution of the acyl chains in galactolipids can be established by electrospray ionization tandem mass spectrometry

Lipid Compositions and Geographical Discrimination of 94 Geographically Authentic Wheat Samples Based on UPLC-MS with Non-Targeted Lipidomic Approach

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