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Selected ion monitoring gas chromatography/mass spectrometry of 1,2-diacylglyceroltert-butyldimethylsilyl ethers derived from glycerophospholipids

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Lipids

Abstract

Selected ion monitoring was used in conjunction with gas chromatography/mass spectrometry to analyzetert-butyldimethylsilyl ethers (tert-BDMS) of 1,2-diacyl-sn-glycerols derived from naturally occurring glycerophospholipids, including those ofEscherichia coli, soybean, egg yolks and porcine liver. First, the fatty acid composition of the unknown glycerophospholipid was determined by gasliquid chromatography (GLC) and, based on that, the fatty acids (mostly >0.5 wt%) were selected for monitoring the characteristic fragmentation ions produced from the fatty acid residues of the correspondingtert-BDMS derivatives of 1,2-diacyl-sn-glycerols. Next, thetert-BDMS derivatives were separated by GLC on a 65% methylphenylsilicone gum wall-coated open-tubular (WCOT) column according to the degree of unsaturation and the chain length of the fatty acid residues, and then directly introduced into the ion source of the mass spectrometer. The selected fragmentation ions, [RCO+74]+ representative of the fatty acid residues, and [M-57]+ indicative of the molecular weight of the derivatives, were monitored simultaneously. It thus became possible to determine the molecular species of thetert-BDMS derivatives by measuring a specific combination of two [RCO+74]+ and an [M-57]+ ion with the same retention time on the selected ion monitoring (SIM) profile. High background noise caused by volatilization of stationary phase at high temperature was largely overcome by selected ion monitoring. However, the fragmentation ion peaks produced fromtert-BDMS derivatives of highly unsaturated glycerophospholipids showed a distorted SIM profile, which was attributed to interaction between thetert-BDMS derivatives and the methylphenylsilicone phase of the column. Use of a WCOT column with a more polar liquid phase is therefore recommended for the analysis of highly unsaturated molecular species.

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Abbreviations

tert-BDMS:

tert-butyldimethylsilyl ether

CPL:

choline glycerophospholipid

EPL:

ethanolamine glycerophospholipid

FID:

flame ionization detector

GC/MS:

gas chromatography/mass spectrometry

GLC:

gas-liquid chromatography

SIM:

selected ion monitoring

TC/DB:

total-acyl carbonsvs. double bonds

WCOT:

wall-coated open-tubular

Δ:

cycropropanoic fatty acid,e.g., 17∶0Δ represents 17∶0 fatty acid with a cyclopropanoid ring

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Authors and Affiliations

  1. Dept. of Food Science and Technology, The Tokyo University of Fischeries, Konan 4, Minato-ku, 108, Tokyo, Japan

    Toshiaki Ohshima & Chiaki Koizumi

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  1. Toshiaki Ohshima
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  2. Chiaki Koizumi
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Ohshima, T., Koizumi, C. Selected ion monitoring gas chromatography/mass spectrometry of 1,2-diacylglyceroltert-butyldimethylsilyl ethers derived from glycerophospholipids. Lipids 26, 940–947 (1991). https://doi.org/10.1007/BF02535981

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  • DOI: https://doi.org/10.1007/BF02535981

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