2017
DOI: 10.1002/rcm.7818
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Simultaneous structural identification of diacylglyceryl‐N‐trimethylhomoserine (DGTS) and diacylglycerylhydroxymethyl‐N,N,N‐trimethyl‐β‐alanine (DGTA) in microalgae using dual Li+/H+ adduct ion mode by ultra‐performance liquid chromatography/quadrupole time‐of‐flight mass spectrometry

Abstract: This is the first report to achieve the ambiguous structural identification of DGTS and DGTA by UPLC/QTOF MS using dual Li /H adduct ion mode, which has remained a challenge in the past. It could provide new insights into their phylogeny and be helpful to characterize the natural phytoplankton communities as intact polar lipid biomarkers. Copyright © 2017 John Wiley & Sons, Ltd.

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Cited by 21 publications
(13 citation statements)
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“…Overall, betaine lipids were shown to be the major clusters detected in the bioactive fractions, with betaine diacylglycerols being almost exclusively present in fraction E and betaine monoacylglycerols being the most abundant metabolite in fraction D. Betaine lipids, structural components of cell membranes and chloroplasts, are acylglycerolipids bearing an ether-linked quaternary amine alcohol moiety at the sn -3 position, which may be represented by a 2′-(hydroxymethyl)-( N , N , N -trimethyl)-β-alanine, a carboxy-(hydroxymethyl)-choline, or a 4′-( N , N , N -trimethyl)-homoserine. The product ion spectra generated from the [M + H] + ions of betaine lipids from fractions D and E were all characterized by the presence of the diagnostic fragment ion at m / z 236.1492 (C 10 H 22 NO 5 + ), which is indicative of diacyl- and monoacyl-glycerol-trimethylhomoserine (DGTS and MGTS) or diacyl- and monoacyl-glyceryl-hydroxymethyl- N , N , N -trimethyl-β-alanine (DGTA and MGTA) [ 25 ]. Therefore, betaine lipids from the bioactive fractions were predicted to be DGTS and MGTS and/or DGTA and MGTA.…”
Section: Resultsmentioning
confidence: 99%
“…Overall, betaine lipids were shown to be the major clusters detected in the bioactive fractions, with betaine diacylglycerols being almost exclusively present in fraction E and betaine monoacylglycerols being the most abundant metabolite in fraction D. Betaine lipids, structural components of cell membranes and chloroplasts, are acylglycerolipids bearing an ether-linked quaternary amine alcohol moiety at the sn -3 position, which may be represented by a 2′-(hydroxymethyl)-( N , N , N -trimethyl)-β-alanine, a carboxy-(hydroxymethyl)-choline, or a 4′-( N , N , N -trimethyl)-homoserine. The product ion spectra generated from the [M + H] + ions of betaine lipids from fractions D and E were all characterized by the presence of the diagnostic fragment ion at m / z 236.1492 (C 10 H 22 NO 5 + ), which is indicative of diacyl- and monoacyl-glycerol-trimethylhomoserine (DGTS and MGTS) or diacyl- and monoacyl-glyceryl-hydroxymethyl- N , N , N -trimethyl-β-alanine (DGTA and MGTA) [ 25 ]. Therefore, betaine lipids from the bioactive fractions were predicted to be DGTS and MGTS and/or DGTA and MGTA.…”
Section: Resultsmentioning
confidence: 99%
“…For some of them, these lipid families were characterized through specific fragment ions, such as m/z 236.1494 [C10H22NO5] + for DGTAs and m/z 184.0722 [C 5 H 15 NO 4 P] + for PCs. DGTAs were distinguished from their structural isomers diacylgycerol-N-trimethylhomoserines (DGTSs) based on the absence of a characteristic loss of m/z 87 (Roche and Leblond, 2010), even if it is matter of controversy (Li et al, 2017). Clusters B and F consisted of terpenoids, including several sesquiterpenes and geranylgeranylglycerol (GGG) previously purified from T. atomaria (Othmani et al, 2016a,b).…”
Section: Global Annotation Of Metabolomesmentioning
confidence: 99%
“…The negative ion mode was applied for quantitative analysis of PI and the positive mode was applied for analyzing others lipid classes. Previously described fragmentation reactions were used for sn-position of acyl chains determination in all polar lipid classes [ 56 , 57 , 58 , 59 , 60 ], except GlcADG and PHEG. For the identification of MGDG, DGDG and PC, [M + Li] + ions were used, in this case 5mM LiOH in methanol with 0.02 mL/min flow was added postcolumn.…”
Section: Methodsmentioning
confidence: 99%