Microdetermination of molecular species of oligo- and polyunsaturated diacylglycerols by gas chromatography-mass spectrometry of their tert-butyldimethylsilyl ethers

Myher, J. J.; Kuksis, A.; Marai, L.; Yeung, Sharon

doi:10.1021/ac50026a006

Cited by 90 publications

(15 citation statements)

References 31 publications

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“…The reagents, trimethylchlorosilane, hexamethyldisilazane, and pyridine were obtained from Pierce Chemical Cs., Rockford, IL, and t-BBMS-imidazole reagent was obtained from Applied Science Laboratories, State College, PA. Phospholipase C (Clostridurn welchii, type 1) was obtained from Sigma Chemical Co., St. Louis, MO. Synthetic sn-1,2-diacylglycemls containing the common fatty acids were available in the labratory from previous studies ( 10,13). Any sn-1,3-diacylglycerol derivatives formed on storage were removed by thin-layer chromatography with boric acid impregnated silica gel using chlomform-acetone 97:3 as the solvent (16).…”

Section: Methodsmentioning

confidence: 99%

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Resolution of diacylglycerol moieties of natural glycerophospholipids by gas–liquid chromatography on polar capillary columns

Myher¹,

Kuksis²

1982

Can. J. Biochem.

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101

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A rapid and practical method has been developed for the gas-liquid chromatographic determination of the sn-1,2-diacylglycerol moieties of natural glycerophospholipids using polar wall-coated open tubular columns. The method gives complete resolution and quantitative estimates for all species according to molecular weight and degree of unsaturation, including stearoyl docosahexaenoylglycerol and related polyunsaturates. For this purpose the sn-1,2-diacylglycerols are obtained from the glycerophospholipids by hydrolysis with phospholipase C and are converted into the trimethylsilyl or tertiary-butyldimethylsilyl ethers. The silyl ethers are separated by gas-liquid chromatography on the capillary glass columns coated with a polar cyanopropylsiloxane polymer, in the temperature range 175-250 degrees C, using hydrogen as the carrier gas. Practical applications of the method are illustrated by analyses of the sn-1,2-diacylglycerol moieties of the phosphatidylcholines of soybean phosphatides, egg yolk, and rat liver. The method of analysis is applicable to other classes of glycerophospholipids and the total time requirements for the analysis of any one phospholipid class are comparable to those for a fatty acid analysis.

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Section: Methodsmentioning

confidence: 99%

“…The phmphatidylcholines of soybean oil were similarly isolated from commercially available soybean phosphatihs (Sigma Chemical Co., St. Louis, MO and C. E. Jamieeon and Cs., Windmr, Ont.). The phosphatidylcholines of egg yolk were available fiQm a previous study (10).…”

Section: Methodsmentioning

confidence: 99%

Resolution of diacylglycerol moieties of natural glycerophospholipids by gas–liquid chromatography on polar capillary columns

Myher¹,

Kuksis²

1982

Can. J. Biochem.

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101

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“…The operating conditions were the same as those described previously (Jeong et al 1991b). Monitoring the characteristic fragment ions that were reported in previous studies (Myher et al 1978;Satouchi and Saito 1979) performed the peak assignment of the alkenylacylglycerol and diacylglycerol tert-BDMS ether derivatives.…”

Section: Glc and Sim-gcms Of Tert-bdms Derivatives Of Diradylglycerolmentioning

confidence: 99%

CHANGES IN MOLECULAR SPECIES COMPOSITIONS OF GLYCEROPHOSPHOLIPIDS IN THE ADDUCTOR MUSCLE OF THE GIANT EZO SCALLOP PATINOPECTEN YESSOENSIS DURING FROZEN STORAGE

Jeong

Ohshima

Koizumi

1999

Journal of Food Lipids

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Changes in lipid components, particularly glycerophospholipids, in the adducto; muscle of giant ezo scallop during storage at −20C were investigated. During storage, the contents of total lipids (TL) and polar lipids (PL) decreased, but that of nonpolar lipids increased. Thiobarbituric acid reactive substances and peroxide values of the TL increased with duration of storage. Glycerylphosphorylcholine (GPC) and glycerylphosphrylethanolamine (GPE) decomposed considerably during storage, and decreased by 50% and 15% of the initial content, while lyso‐PC (LPC) and free fatty acids (FFA) increased, respectively. The percentages of polyunsaturated fatty acids (PUFAs) such as 20:5n‐3 and 22:6n‐3 in the TL and PL during storage decreased, however, those of the PUPAs in the NL increased. Diacylglycerylphosphorylcholine (diacyl‐GPC) and diacylglycerylophosphorylethanolamine (diacyl‐GPE), major components in the GPC and GPE subclasses, showed a marked decrease with duration of storage. Particularly, diacyl‐GPC decreased by 68% of the initial contents of the PL. In the alkenylacyl‐GPE and diacyl‐GPC, the percentages of the molecular species having longer hydrocarbon chains on the sn‐l positions of glycerol moieties decreased at

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“…The molecular species of the various diacylglycerol preparations were determined by gc/ms of their t-BDMS ethers as previously described (26). Stereospecific analyses of the total triacylglycerols were performed according to Brockerhoff (27).…”

Section: Aaa%ysm Oj Lipidsmentioning

confidence: 99%

Acylglycerol structure of mustard seed oil and of cardiac lipids of rats during dietary lipidosis

Myher¹,

Kuksis²,

Vasdev³

et al. 1979

Can. J. Biochem.

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Stereospecific degradation and combined gas chromatographic--mass spectrometric (gc/ms) analysis were employed in a detailed investigation of the triacylglycerol structure of mustard seed oil and of the triacylglycerols transiently accumulating in the hearts of young rats receiving the oil in their diet. It was shown that feeding of mustard seed oil at 40% of the daily caloric requirement resulted in a deposition of cardiac triacylglycerols containing a high proportion of enantiomers of a positional distribution and molecular association of fatty acids which were closely similar to those found in the dietary oil. Complete structures were derived for a total of 88 species representing 75 to 85% of the triacylglycerols. About 90% of the accumulated triacylglycerol contained at least one long-chain (C20--C22) monounsaturated fatty acid per molecule. The long-chain acids were confined mainly to the primary positions and preferentially to the sn-3-position of the glycerol molecule. The dietary lipidosis, is, therefore, accompanied by little or no accumulation of the normal rat tissue triacylglycerols containing C16 and C18 fatty acids. It is suggested that the deposition and eventual clearance of the enantiomeric long-chain triacylglycerols in the rat heart during mustard seed oil feeding may be largely a result of a gradual change in specificity of the cardiac lipases.

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Microdetermination of molecular species of oligo- and polyunsaturated diacylglycerols by gas chromatography-mass spectrometry of their tert-butyldimethylsilyl ethers

Cited by 90 publications

References 31 publications

Resolution of diacylglycerol moieties of natural glycerophospholipids by gas–liquid chromatography on polar capillary columns

Resolution of diacylglycerol moieties of natural glycerophospholipids by gas–liquid chromatography on polar capillary columns

CHANGES IN MOLECULAR SPECIES COMPOSITIONS OF GLYCEROPHOSPHOLIPIDS IN THE ADDUCTOR MUSCLE OF THE GIANT EZO SCALLOP PATINOPECTEN YESSOENSIS DURING FROZEN STORAGE

Acylglycerol structure of mustard seed oil and of cardiac lipids of rats during dietary lipidosis

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