The Structure of Plasmalogens—iii: The Nature and Significance of the Aldehydogenic Linkage

Rapport, Maurice M.; Franzl, Robert E.

doi:10.1111/j.1471-4159.1957.tb12086.x

Cited by 61 publications

(7 citation statements)

References 17 publications

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“…The discovery of this class of molecules was made originally in myelin by Feulgen and Voit in 1924 [52], but the accurate structure of plasmalogens was deduced only several years later [53,54]. The biological function of plasmalogens, and their implication in diseases remained elusive for a number of years until a recent spike in interest in these lipids.…”

Section: Discussionmentioning

confidence: 99%

Membrane plasmalogen composition and cellular cholesterol regulation: a structure activity study

Mankidy

Ahiahonu

et al. 2010

Lipids Health Dis

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BackgroundDisrupted cholesterol regulation leading to increased circulating and membrane cholesterol levels is implicated in many age-related chronic diseases such as cardiovascular disease (CVD), Alzheimer's disease (AD), and cancer. In vitro and ex vivo cellular plasmalogen deficiency models have been shown to exhibit impaired intra- and extra-cellular processing of cholesterol. Furthermore, depleted brain plasmalogens have been implicated in AD and serum plasmalogen deficiencies have been linked to AD, CVD, and cancer.ResultsUsing plasmalogen deficient (NRel-4) and plasmalogen sufficient (HEK293) cells we investigated the effect of species-dependent plasmalogen restoration/augmentation on membrane cholesterol processing. The results of these studies indicate that the esterification of cholesterol is dependent upon the amount of polyunsaturated fatty acid (PUFA)-containing ethanolamine plasmalogen (PlsEtn) present in the membrane. We further elucidate that the concentration-dependent increase in esterified cholesterol observed with PUFA-PlsEtn was due to a concentration-dependent increase in sterol-O-acyltransferase-1 (SOAT1) levels, an observation not reproduced by 3-hydroxy-3-methyl-glutaryl-CoA (HMG-CoA) reductase inhibition.ConclusionThe present study describes a novel mechanism of cholesterol regulation that is consistent with clinical and epidemiological studies of cholesterol, aging and disease. Specifically, the present study describes how selective membrane PUFA-PlsEtn enhancement can be achieved using 1-alkyl-2-PUFA glycerols and through this action reduce levels of total and free cholesterol in cells.

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Section: Discussionmentioning

confidence: 99%

Membrane plasmalogen composition and cellular cholesterol regulation: a structure activity study

Mankidy

Ahiahonu

et al. 2010

Lipids Health Dis

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“…Notably, their sn‐1 acyl chain is attached to the glycerol backbone by an ether bond, in contrast to the more common ester linkage (See Fig. ) . In addition to an ether bond, plasmalogens contain a double bond in cis‐(Z) configuration adjacent to the ether oxygen atom, as assigned by utilizing the infrared spectroscopy .…”

Section: The Biophysical Properties Of Plasmalogensmentioning

confidence: 99%

The biophysical properties of plasmalogens originating from their unique molecular architecture

Koivuniemi

2017

FEBS Letters

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Plasmalogens are a unique class of phospholipids that are present in many organisms. Their presence in cell membranes has intrigued researchers for decades due to their unique molecular structure, namely the vinyl‐ether bond at the sn‐1 position, and their association with brain related disorders. Apparently, based on their amount in the cell membranes, their function is to provide exclusive structural and dynamical properties to these complex molecular assemblies. Yet, many of their physiological roles manifested through their biophysical properties have been challenging to identify. In this review, the biophysical properties of plasmalogens are discussed and compared to other lipid species. The role of plasmalogens is examined in the context of cell membrane function, and some future directions are given.

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“…to their alkaline stability, hydrolysis with acids and mercuric ions, reaction with fuchsin-sulfurous acid, addition of hydrogen and methanolic iodine, ozonolysis, and reactions with aldehyde reagents (2,3,20).…”

Section: Scheme I Reactivity Of the 0-alk-i-enyl Linkage It1mentioning

confidence: 99%

“…Stabilization of riboflavin to light in the presence of additives is pharmaceutically important, since certain additives were observed to have considerable influence on the light stability of the system (13)(14)(15)(16)(17)(18)(19)(20)(21)(22). Despite this importance, very few photochemical kinetic studies have been published for riboflavin in the presence of complexing agents.…”

Section: Acknowledgments and Addressesmentioning

confidence: 99%

Plasmalogens and Related Derivatives: Their Chemistry and Metabolism

Piantadosi

Snyder

1970

Journal of Pharmaceutical Sciences

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The Structure of Plasmalogens—iii: The Nature and Significance of the Aldehydogenic Linkage

Cited by 61 publications

References 17 publications

Membrane plasmalogen composition and cellular cholesterol regulation: a structure activity study

Membrane plasmalogen composition and cellular cholesterol regulation: a structure activity study

The biophysical properties of plasmalogens originating from their unique molecular architecture

Plasmalogens and Related Derivatives: Their Chemistry and Metabolism

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