Sphingomyelin Interfacial Behavior: The Impact of Changing Acyl Chain Composition

Li, Xin Min; Smaby, Janice M.; Momsen, Maureen M.; Brockman, Howard L.; Brown, Rhoderick E.

doi:10.1016/s0006-3495(00)76740-3

Cited by 115 publications

(107 citation statements)

References 63 publications

(95 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Two structural features of SM that enable it to provide a specialized membrane environment with a tendency to form microdomains are the presence 1) at the membrane surface of functional groups capable of functioning as donors (the hydroxyl group) and acceptors (the nitrogen in the amide bond) in hydrogen bond interactions with neighboring lipids and 2) deeply embedded in the membrane, of hydrophobic chains with marked length asymmetry (26,27). By comparing the behavior in monolayers of pure SM with medium (C12-C14), long (C16 -C18), and very long (C24 -C26) acyl chains, it was shown that chain length alone has an important impact on interfacial properties (26).…”

Section: Discussionmentioning

confidence: 99%

Very Long-chain Polyunsaturated Fatty Acids Are the Major Acyl Groups of Sphingomyelins and Ceramides in the Head of Mammalian Spermatozoa

Furland

Oresti

Antollini

et al. 2007

Journal of Biological Chemistry

View full text Add to dashboard Cite

Very long-chain (C24 to C34) polyunsaturated fatty acids (VLCPUFA) are important constituents of sphingomyelin (SM) and ceramide (Cer) in testicular germ cells. In the present paper we focused on the SM and Cer and their fatty acids in spermatozoa and their main regions, heads and tails. In bull and ram spermatozoa, SM was the third most abundant phospholipid and VLCPUFA were the major acyl groups (ϳ70%) of SM and Cer. In rat epididymal spermatozoa the SM/Cer ratio was low in the absence of and could be maintained high in the presence of the cation chelator EDTA, added to the medium used for sperm isolation. This fact points to the occurrence of an active divalent cation-dependent sphingomyelinase. Bull and rat sperm had an uneven head-tail distribution of phospholipid, with virtually all the VLCPUFA-rich SM located at the head, the lower SM content in the rat being determined by the lower sperm head/tail size ratio. Most of the SM from bull sperm heads was readily solubilized with 1% Triton X-100 at 4°C. The detergent-soluble SM fraction was richer in VLCPUFA than the nonsoluble fraction and richer in saturated fatty acids. Cer was produced at the expense of SM, thus decreasing severalfold the SM/Cer ratio in rat spermatozoa incubated for 2 h in presence of the spermcapacitating agents, calcium, bicarbonate, and albumin. The generation of Cer from SM in the sperm head surface may be an early step among the biochemical and biophysical changes known to take place in the spermatozoon in the physiological events preceding fertilization.In a number of mammals including humans a series of very long-chain polyunsaturated fatty acids (VLCPUFA), 2 i.e. n-6 and n-3 tetraenoic, pentaenoic and hexaenoic fatty acids with up to 32 or 34 carbon atoms, depending on the species, was characterized in the sphingomyelin (SM) from testis and spermatozoa (1, 2). In the testis of various mammals, we focused on the fatty acids of the ceramide (Cer), a lipid molecule with which SM bears a close precursor-product relationship, showing that SM and Cer species containing VLCPUFA are a specific feature of cells of the spermatogenic lineage (3). Because these testicular cells are predecessors of spermatozoa, the question arose as to the quantitative importance of these molecules in spermatozoa, where they could play a role in sperm functions related to fertilization. Transit through the epididymis is a crucial phase in sperm maturation. Spermatozoa exiting the testis are immotile, unable to bind to eggs and to undergo the acrosomal reaction in vitro in response to commonly used stimuli. By the time they reach the region of cauda epididymis, sperm cells have acquired their progressive motility and their ability to bind, penetrate, and fertilize eggs (4). One of the questions we addressed was whether epididymal maturation gives rise to spermatozoa with a larger or a smaller proportion of SM and Cer containing these VLCPUFA as opposed to other fatty acids.Spermatozoa are functionally regionalized cells. Sperm-oocyte interactions are head-relat...

show abstract

Section: Discussionmentioning

confidence: 99%

Very Long-chain Polyunsaturated Fatty Acids Are the Major Acyl Groups of Sphingomyelins and Ceramides in the Head of Mammalian Spermatozoa

Furland

Oresti

Antollini

et al. 2007

Journal of Biological Chemistry

View full text Add to dashboard Cite

show abstract

“…5D ) of the fl uorescence melting temperature SLs. The strong asymmetry of VLCSLs might also affect the packing and the distribution of the bulk lipids in the bilayer by promoting the formation of interdigitated phases ( 19,20,(40)(41)(42).…”

Section: Effect Of Cer Acyl Chain Structure On Membrane Biophysical Pmentioning

confidence: 99%

“…Considering this hypothesis, the enrichment in VLC-SLs in CerS2-transfected cells might contribute to the formation of membrane regions enriched in these VLC-lipids that tend to segregate from other lipid components as a consequence of the strong mismatch between their chain structures, and therefore cause an increase in the fraction of ordered membrane regions. In addition, VLC-SLs have higher melting temperatures compared with LC-SLs [e.g., ( 40 )], which contributes to a decrease in their miscibility with the other lipid components and consequent formation of more ordered membrane regions enriched in these high differences were observed, which can be explained by the formation of different acyl chain Cers in the PM. Accordingly, these results suggest that alterations in SL metabolism by transfecting cells with different CerSs leads to a change in the lipid composition of the PM, most likely due to the changes introduced in the acyl chain structure of the SL formed.…”

Section: Cer-induced Membrane Remodelingmentioning

confidence: 99%

Changes in membrane biophysical properties induced by sphingomyelinase depend on the sphingolipid N-acyl chain

Pinto¹,

Laviad²,

Stiban³

et al. 2014

Journal of Lipid Research

View full text Add to dashboard Cite

“…7). MD simulations and monolayer experiments [15][16][17] suggest that only the SM species with a suitable dynamic volume would fit into the cavity of the p24 TMD formed by V13, T16, and L17, excluding lipids with larger dynamic volume (SM 14 and 16, see Supplementary Fig. 7).…”

mentioning

confidence: 99%

Molecular recognition of a single sphingolipid species by a protein’s transmembrane domain

Contreras

Ernst

Haberkant

et al. 2012

Nature

350

320

View full text Add to dashboard Cite

This is an accepted version of a paper published in Nature. This paper has been peer-reviewed but does not include the final publisher proof-corrections or journal pagination.Citation for the published paper: von Heijne, G., Contreras, X., Ernst, A., Haberkant, P., Björkholm, P. et al. (2012) "Molecular recognition of a single sphingolipid species by a protein's transmembrane domain" Nature, 481 (7382): 525-529 URL: http://dx

show abstract

Sphingomyelin Interfacial Behavior: The Impact of Changing Acyl Chain Composition

Cited by 115 publications

References 63 publications

Very Long-chain Polyunsaturated Fatty Acids Are the Major Acyl Groups of Sphingomyelins and Ceramides in the Head of Mammalian Spermatozoa

Very Long-chain Polyunsaturated Fatty Acids Are the Major Acyl Groups of Sphingomyelins and Ceramides in the Head of Mammalian Spermatozoa

Changes in membrane biophysical properties induced by sphingomyelinase depend on the sphingolipid N-acyl chain

Molecular recognition of a single sphingolipid species by a protein’s transmembrane domain

Contact Info

Product

Resources

About