Identification of a new sphingolipid 3-O-acyl-d-erythro-sphingomyelin in newborn pig and infant plasma

Kramer, J. K. G.; Blackwell, Barbara A.; Dugan, M. E. R.; Sauer, Frank

doi:10.1016/0005-2760(96)00080-x

Cited by 7 publications

(3 citation statements)

References 17 publications

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“…The fatty acids of SM ranged in chain length from 13 to 28 carbons, of which over half were saturated (with 16:0 comprising about one-third of all SM subspecies), about 20% were monounsaturated (the most prevalent being 24:1), and there were small amounts of fatty acids with two (about 3%) and three (<1%) double bonds. Our approaches would not have detected 3-O-acyl-SM, which has been reported in trace amounts ( 22 ), because the acyl-group would be hydrolyzed during extraction ( 23 ). These proportions are likely to vary among individuals because diet can affect the types and amounts of SM in plasma (24)(25)(26).…”

Section: Sphingolipidsmentioning

confidence: 95%

Lipidomics reveals a remarkable diversity of lipids in human plasma

Quehenberger

Armando

Brown

et al. 2010

Journal of Lipid Research

1,115

993

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In this era of genomics, transcriptomics, and proteomics, metabolomics is emerging as an important component of the omics evolution ( 1 ). Of the four kinds of biological molecules that comprise the human body, i.e., nucleic acids, amino acids (proteins), carbohydrates (sugars), and lipids (fats), lipids stand out among the various cellular metabolites in the sheer number of distinct molecular species. Using state-of-the-art lipidomics approaches made possible by newly developed instrumentation, protocols, and bioinformatics tools ( 2 ), the LIPID MAPS Consortium Abstract The focus of the present study was to defi ne the human plasma lipidome and to establish novel analytical methodologies to quantify the large spectrum of plasma lipids. Partial lipid analysis is now a regular part of every patient's blood test and physicians readily and regularly prescribe drugs that alter the levels of major plasma lipids such as cholesterol and triglycerides. Plasma contains many thousands of distinct lipid molecular species that fall into six main categories including fatty acyls, glycerolipids, glycerophospholipids, sphingolipids, sterols, and prenols. The physiological contributions of these diverse lipids and how their levels change in response to therapy remain largely unknown. As a fi rst step toward answering these questions, we provide herein an in-depth lipidomics analysis of a pooled human plasma obtained from healthy individuals after overnight fasting and with a gender balance and an ethnic distribution that is representative of the US population. In total, we quantitatively assessed the levels of over 500 distinct molecular species distributed among the main lipid categories. As more information is obtained regarding the roles of individual lipids in health and disease, it seems likely that future blood tests will include an ever increasing number of these lipid molecules. -Quehenberger, O., A.

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Section: Sphingolipidsmentioning

confidence: 95%

Lipidomics reveals a remarkable diversity of lipids in human plasma

Quehenberger

Armando

Brown

et al. 2010

Journal of Lipid Research

1,115

993

View full text Add to dashboard Cite

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“…This phospholipid, which incorporates a second oleoyl chain in the phospholipid architecture, is a novel membrane-forming phospholipid containing three alkyl chains (see Supporting Information for additional data), and is reminiscent of unique multichain phospholipids such as 3-O-acyl-d-erythro-sphingomyelin. [21] Phospholipid synthesis was analyzed over time using combined liquid chromatography (LC), mass spectrometry (MS), and evaporative light-scattering detection (ELSD) measurements. Addition of MESNA thioester to the cysteinebased lysolipid in the appropriate buffer immediately led to amidophospholipid formation, and this process progressed to near completion over a period of 30 min using millimolar concentrations of reactants ( Figure S3).…”

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confidence: 99%

In Situ Vesicle Formation by Native Chemical Ligation

2014

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“…Alternatively, addition of precursors in imidazole buffer at neutral pH allowed the NCL ligation and subsequent MESNA thioester reloading,17 leading to the formation of amidophospholipid 4 , albeit in relatively lower yield, possibly because multiple reaction steps were required (Figure 1). This phospholipid, which incorporates a second oleoyl chain in the phospholipid architecture, is a novel membrane‐forming phospholipid containing three alkyl chains (see Supporting Information for additional data), and is reminiscent of unique multichain phospholipids such as 3‐ O ‐acyl‐ D ‐ erythro ‐sphingomyelin 21…”

mentioning

confidence: 99%

In Situ Vesicle Formation by Native Chemical Ligation

2014

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Phospholipid vesicles are of intense fundamental and practical interest, yet methods for their de novo generation from reactive precursors are limited. A non-enzymatic and chemoselective method to spontaneously generate phospholipid membranes from water-soluble starting materials would be a powerful tool for generating vesicles and studying lipid membranes. Here we describe the use of native chemical ligation (NCL) to rapidly prepare phospholipids spontaneously from thioesters. While NCL is one of the most popular tools for synthesizing proteins and nucleic acids, to our knowledge this is the first example of using NCL to generate phospholipids de novo. The lipids are capable of in situ synthesis and self-assembly into vesicles that can grow to several microns in diameter. The selectivity of the NCL reaction enables compatibility of in situ membrane formation with biological materials such as proteins. This work expands the application of NCL to the formation of phospholipid membranes. Keywordsnative chemical ligation; phospholipid; self-assembly; artificial cell; synthetic biology Phospholipid membranes are routinely employed in several practical applications such as the study of protein-membrane interactions, [1] drug-delivery, [2] origin-of-life studies, [3] bottomup synthetic biology, [4] and synthetic reactors. [5] While the capability of phospholipids to self-assemble into membranes is well studied, [6] the de novo synthesis and assembly of membranes from simple non-membrane forming reactive precursors is poorly understood. Living organisms are capable of in situ synthesis of lipid membranes by utilizing membrane bound acyltransferases and reactive thioester precursors. [7] Given the well-documented challenges associated with reconstituting lipid synthesizing membrane proteins into vesicles, [8] several groups have explored methods to generate lipid membranes de novo from reactive amphiphilic precursors. [9], [10] However, these methods generally suffer from a range of issues, including the necessity of catalysts, lack of soluble starting materials, use of biologically incompatible reactive precursors and the formation of lipids that have limited structural similarity to natural phospholipids. [9] Phospholipid membranes are often Author ManuscriptAuthor Manuscript Author ManuscriptAuthor Manuscript advantageous in complex environments due to their stability and biocompatibility. [11] Simpler and more robust methods for phospholipid synthesis could also find use as drivers for the growth and division of primitive protocells. [11], [12] Therefore, it would be exciting to develop a catalyst-free method to generate and grow phospholipid membrane vesicles from reactive soluble precursors. Furthermore, it would be interesting to utilize water-soluble thioester precursors, analogous to living cells. [7], [13] Here we demonstrate that the chemoselective native chemical ligation (NCL) [14] is capable of in situ synthesis of phospholipid vesicles from long-chain thioesters. The lipids are capable o...

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Identification of a new sphingolipid 3-O-acyl-d-erythro-sphingomyelin in newborn pig and infant plasma

Cited by 7 publications

References 17 publications

Lipidomics reveals a remarkable diversity of lipids in human plasma

Lipidomics reveals a remarkable diversity of lipids in human plasma

In Situ Vesicle Formation by Native Chemical Ligation

In Situ Vesicle Formation by Native Chemical Ligation

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