The quantitative determination of plasmalogen by its reaction with mercuric chloride

Carey, Eric M.

doi:10.1007/bf02535374

Cited by 12 publications

(3 citation statements)

References 24 publications

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“…~~~-~~~ A procedure for the determination of plasmalogens, making use of the reaction with mercuric chloride, has been published. 340 The glycolipid content of a tissue can be determined, following hydrolysis of the lipids, by converting the sphingoid bases into the fluorescent 4-dimethylaminoazobenzene-4'-sulphonyl derivatives, which can be isolated, by means of h.p.l.c., for spectrophotometric d e t e r m i n a t i ~n . ~~ Silicic acid column-chromatography procedures have been devised for the isolation of p h o s p h ~n o l i p i d s .…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

The chemistry and biochemistry of simple and complex lipids

Christie¹

1984

Nat. Prod. Rep.

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Section: Miscellaneous Methodsmentioning

confidence: 99%

The chemistry and biochemistry of simple and complex lipids

Christie¹

1984

Nat. Prod. Rep.

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“…The enol ether double bond of the plasmalogens was previously shown to bind mercury ions [29]. It can be assumed that the decrease in the amplitude of the enol ether methine "H peak induced by CuSO % is due to the formation of a complex between Cu(II) and the plasmalogen-specific enol ether.…”

Section: Interaction Of Micellar Plasmalogen Phospholipids With Coppementioning

confidence: 99%

Contribution of copper binding to the inhibition of lipid oxidation by plasmalogen phospholipids

et al. 1999

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The role of plasmalogen phospholipids for copper-induced lipid oxidation was evaluated. Using 1H-NMR we observed that the copper (CuSO4)-promoted oxidative degradation of polyunsaturated fatty acids in micellar solution was dose-dependently attenuated by the plasmalogen lysoplasmenylethanolamine from bovine brain (lysoBP-PtdEtn). This was due to a direct interaction of copper ions with the plasmalogen-specific enol ether double bond. The enol ether methine 1H signal decreased on the addition of copper, saturation being reached at a molar ratio of lysoBP-PtdEtn to copper of 1:1. The original 1H signal was recovered almost completely after the addition of EDTA. Enrichment of micelles and low-density lipoproteins (LDLs) with plasmalogen phospholipids led to a decrease in the Cu(II) concentration in the aqueous media. After loading of LDLs in vitro with BP-PtdEtn, the LDL-dependent formation of Cu(I) was decreased, in particular in particles experimentally supplemented with alpha-tocopherol. The suppression of copper-promoted lipid oxidation that was observed in the presence of plasmalogen phospholipids plus alpha-tocopherol was greater than the sum of the protective effects elicited by the two substances alone. In conclusion, the formation of a complex between copper ions and the plasmalogens accounts partly for their inhibition of copper-induced lipid oxidation.

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“…The alk-l-enyl group is a unique and highly electron-rich double bond, which is easily protonated and capable of complexing with electrophilic species (such as tetracyanoethylene [1 ], maleic anhydride [2] and mercuric ion [3]), to a degree unseen with isolated double bonds. With the exception of early argentation thin layer chromatography (TLC) work discussed below, however, such interactions have not been used to attempt the isolation of intact plasmalogen from nonplasmalogen analogs.…”

Section: Introductionmentioning

confidence: 99%

HPLC of plasmalogen‐containing phosphatidylcholine under reverse‐phase or argentation conditions

Marmer

Foglia

Vail

1984

Lipids

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Two approaches to the high pressure liquid chromatography (HPLC) isolation of intact plasmalogens were investigated. The first used reversed-phase HPLC and sought to take advantage of subtle differences in the hydrophobicity of the alk-1-enyl chain from the acyl counterpart. On a C-18 column, bovine heart phosphatidylcholine (PC), which was 47% plasmalogen, was separated into a number of fractions that differed in their molecular species composition. One combination of fractions amounted to a 26% yield of PC enriched to 82% plasmalogen. The second approach sought to take advantage of the uniquely electron-rich functionality of the plasmalogens, the alk-1-enyl ether double bond, and its potential to coordinate with heavy metal ions. Specifically, bovine heart PC was applied to a cation-exchange type HPLC column in the silver ion mode. Although complete exchange of all the active sites of the column with silver ion led to complete retention of PC, partial activation with silver ion resulted in the separation of the PC into fractions, according to the degree of unsaturation. Plasmalogen-rich fractions eluted last and remained intact during the process. One combination of these fractions amounted to a 49% yield of PC enriched to 72% plasmalogen. Use of a cation-exchange system in the mercuric ion mode led to on-column hydrolysis of the plasmalogen; with palladium ion, the metallic species was stripped from the column by the eluting lipid.

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The quantitative determination of plasmalogen by its reaction with mercuric chloride

Cited by 12 publications

References 24 publications

The chemistry and biochemistry of simple and complex lipids

The chemistry and biochemistry of simple and complex lipids

Contribution of copper binding to the inhibition of lipid oxidation by plasmalogen phospholipids

HPLC of plasmalogen‐containing phosphatidylcholine under reverse‐phase or argentation conditions

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