Isolation of ceramide phosphorylethanolamine from the blowfly Calliphora erythrocephala

Dawson, R. M. C.; Kemp, P.

doi:10.1042/bj1060319

Cited by 19 publications

(6 citation statements)

References 6 publications

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“…The 1 H NMR spectrum of sphingomyelin 1 was obtained in CD 3 OD, and H-3 was located at 4.04 ␦. Based on these results, the erythro configuration was assigned to 1.…”

Section: Resultsmentioning

confidence: 99%

“…Fractions with retention times of 32 and 33 min were evaporated to dryness, and spectroscopic data were recorded in CDCl 3 ( Attempts were made to obtain the chain lengths of sphingomyelin using ESI-MS n in the same way as was done for ceramides. As the isolated sphingomyelin exists mainly in the sodiated form, it loses 59 mass units (trimethyl amine) and 124 (rest of the phosphocholine group).…”

Section: Resultsmentioning

confidence: 99%

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Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta

Abeytunga

Glick

Gibson

et al. 2004

Journal of Lipid Research

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NMR and electrospray ionization tandem mass spectrometry were used to show for the first time the presence of sphingomyelins in extracts of the tobacco hornworm Manduca sexta ( Lepidoptera ). The sphingosine in the ceramide was identified as tetradecasphing-4-enine, and the fatty acids were C18:0, C20:0, C22:0, and C24:0 (compound 1). Heterogeneity in the ceramide was observed in sphingomyelins from M. sexta. All of the sphingomyelins were associated with their doubly unsaturated sphingosine, tetradecasphing-4,6-dienine (compound 2), which contained the same set of fatty acids as compound 1 and represents a novel set of sphingomyelins not previously reported in Lepidoptera. Lipid rafts were isolated from brains of M. sexta, and the association of these novel sphingomyelins with rafts was confirmed. The existence of the additional double bond was also observed in ceramide and ceramide phosphoethanolamine isolated from M. sexta Interest in insect sphingosines as cell membrane constituents dates back to the 1960s (1), but three decades of work has provided information on this class of compounds for only a few insect species, namely, Musca domestica (2), Calliphora erythrocephala (3), Trogoderma granarium (4), Apis mellifera (5), and Aedes albopictus (6). Similarly, only limited information exists with regard to insect glycosphingolipids (GSLs, arthrosides). The mosquito Aedes aegypti (7), the green-bottle fly Lucilia caesar (8), the blowfly Calliphora vicina (9), and Drosophila melanogaster (10) have been studied, with no report of sphingomyelin in these species. Sphingomyelin is commonly found in small amounts as a cell membrane component in mammals and is present in myelinated nerve fibers in larger amounts, but its exact functions have yet to be elucidated in insects. Because ceramides and sphingosine-1-phosphate have been identified as important regulators of apoptosis, cell motility, and raft formation in mammals (11, 12), the absence of such molecules in insects would have serious implications, inasmuch as biochemical pathways in insects and vertebrates have generally been conserved over tens of millions of years.In his review on insect glycolipids, Wiegandt (13) stated that insect ceramides typically consist of C14:1 and C16:1 sphingosines, which are shorter than mammalian bases of 18 carbons or longer. The fatty acids reported at that time were C18:0, C20:0, and C22:0. The sphingolipids isolated from Dipteran differed from vertebrate sphingolipids, and the presence of sphingomyelin was not reported.The characterization of sphingosine derivatives is challenging, inasmuch as they typically constitute far less than 1% of the total lipid content of a tissue sample (14). Previously, time-consuming chemical decomposition methods and chemical derivatization were required for structural elucidation of the lipid and phospholipids of Manduca sexta (15). More recently, electrospray ionization-tandem mass spectrometry (ESI-MS/MS) was employed by Hsu Abbreviations: CID, collision-induced dissociation; COSY, cor...

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“…The 1 H NMR spectrum of sphingomyelin 1 was obtained in CD 3 OD, and H-3 was located at 4.04 ␦. Based on these results, the erythro configuration was assigned to 1.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta

Abeytunga

Glick

Gibson

et al. 2004

Journal of Lipid Research

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show abstract

“…The location of all identified phospholipids was based on the separation of phospholipid standards. The phospholipid denoted as 'X' is probably ceramide phosphoethanolamine, which has a similar mobility and is present in blowflies (Dawson & Kemp, 1968). Crone & Bridges (1963) originally reported the presence in houseflies of a phospholipid with properties similar to those of ceramide phosphoethanolamine.…”

Section: Chromatographic Separation Ofphospholipidsmentioning

confidence: 99%

Relationship between hormonal activation of phosphatidylinositol hydrolysis, fluid secretion and calcium flux in the blowfly salivary gland

Fain¹,

Berridge²

1979

Biochemical Journal

193

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The addition of 5-hydroxytryptamine to the isolated blowfly salivary gland stimulates fluid secretion, transepithelial calcium transport and the breakdown of 32P- or 3H-labelled phosphatidylinositol The breakdown of [32P]phosphatidylcholine and [32P]-phosphatidylethanolamine was not stimulated by 5-hydroxytryptamine. In salivary glands incubated with myo-[2-3H]inositol for 1--3 h, more than 95% of the label retained by the tissue was in the form of phosphatidylinositol. The addition of 5-hydroxytryptamine resulted in an increase in the accumulation of label in intracellular inositol 1:2-cyclic phosphate, inositol 1-phosphate and free inositol along with an increase in the release of [3H]inositol to the medium and saliva. The release of [3H]inositol to the medium served as a sensitive indicator of phosphatidylinositol breakdown. The release of [3H]inositol was not increased by cyclic AMP or the bivalent-cation ionophore A23187 under conditions in which salivary secretion was accelerated. The stimulation of fluid secretion by low concentrations of 5-hydroxytryptamine was potentiated by 3-isobutyl-1-methylxanthine, which had no effect on inositol release. The stimulation of fluid secretion by 5-hydroxytryptamine was greatly reduced in calcium-free buffer, but the breakdown of phosphatidylinositol continued at the same rate in the absence of calcium. These results support the hypothesis that breakdown of phosphatidylinositol by 5-hydroxytryptamine is involved in the gating of calcium.

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“…Sphingomyelin (ceramide phosphorylcholine [CPC]) has been studied in humans by a number of investigators and has been suggested to be a structural component of cell membranes influenced by a complex interplay of physiological and biochemical factors (2)(3)(4)(5). Ceramide phosphorylethanolamine (CPE), an analogue of sphingomyelin, has been isolated from marine invertebrates (6), dipterous larvae and adults (7)(8)(9)(10)(11), and cultured mosquito cells (12). However, few studies have been performed associating the chemical nature and metabolism of these two sphingophospholipids in insects.…”

Section: Introductionmentioning

confidence: 99%

Sphingophospholipids of species ofAedes andCulex mosquito cells cultivated in suspension culture from logarithmic and stationary phases of growth

Yang

Means

Anderson

et al. 1974

Lipids

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Two sphingophospholipids, sphingomyelin (ceramide phosphorylcholine), and ceramide phosphorylethanolamine, were isolated and purified from cells of four mosquito species obtained from the logarithmic and stationary phases of growth. Quantitation of the two lipids in both phases of growth from cells of each species was made. The fatty acid composition of the two lipids was compared between the cell types and the two phases of growth. There was a tendency for an increase of ceramide phosphorylcholine and a decrease of ceramide phosphorylethanolamine in the stationary phase. Longer chain fatty acids of ceramide phosphorylcholine were observed in the stationary phase than in the logarithmic phase of growth of the mosquito cells. The four species had distinctly different fatty acid patterns in the two complex lipids which might be useful for taxonomic purposes and cell identification.

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Isolation of ceramide phosphorylethanolamine from the blowfly Calliphora erythrocephala

Cited by 19 publications

References 6 publications

Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta

Presence of unsaturated sphingomyelins and changes in their composition during the life cycle of the moth Manduca sexta

Relationship between hormonal activation of phosphatidylinositol hydrolysis, fluid secretion and calcium flux in the blowfly salivary gland

Sphingophospholipids of species ofAedes andCulex mosquito cells cultivated in suspension culture from logarithmic and stationary phases of growth

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