Studies on Glycosphingolipids in Larvae of the Green-Bottle Fly, Lucilia caesar: Two Neutral Glycosphingolipids having Large Straight Oligosaccharide Chains with Eight and Nine Sugars1

Sugita, Mutsumi; Inagaki, Fuyuhiko; Naito, Hiromi; Hori, Taro

doi:10.1093/oxfordjournals.jbchem.a123145

Cited by 25 publications

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“…The structure of higher order sphingolipids has been studied in dipterans (23)(24)(25)(26)(27). However, until the last few years, relatively little information about sphingolipid structure and function in Drosophila has been available.…”

Section: Discussionmentioning

confidence: 99%

Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes

Fyrst¹,

Zhang

Herr

et al. 2008

Journal of Lipid Research

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Sphingolipids comprise a complex group of lipids concentrated in membrane rafts and whose metabolites function as signaling molecules. Sphingolipids are conserved in Drosophila, in which their tight regulation is required for proper development and tissue integrity. In this study, we identified a new family of Drosophila sphingolipids containing two double bonds in the long chain base (LCB). The lipids were found at low levels in wild-type flies and accumulated markedly in Drosophila Sply mutants, which do not express sphingosine-1-phosphate lyase and are defective in sphingolipid catabolism. To determine the identity of the unknown lipids, purified whole fly lipid extracts were separated on a C18-HPLC column and analyzed using electrospray mass spectrometry. The lipids contain a LCB of either 14 or 16 carbons with conjugated double bonds at C4,6. The Sphingolipids are a diverse group of membrane lipids that are highly conserved throughout evolution (1, 2). In mammalian cells, sphingolipid structure, composition, and metabolism have been well characterized. Knowledge of sphingolipid structure has facilitated in-depth analyses of the contribution of sphingolipids to membrane organization and their function in signal transduction events and normal physiology. Such studies have defined an important role for higher order sphingolipids in the formation of membrane subdomains (lipid rafts) wherein growth factor signaling and recruitment occur (3-6), and sphingolipid metabolites have been shown to participate in signaling pathways regulating the key processes of cellular proliferation, migration, stress responses, programmed cell death, angiogenesis, and immune cell trafficking (7-12).We have been exploring the physiological roles of sphingolipids in the genetically tractable organism, Drosophila melanogaster. In this species, tight regulation of sphingolipid levels is required for proper development, reproduction, and the maintenance of tissue integrity, as demonstrated by the severe phenotypes observed in mutants with disrupted sphingolipid metabolism (13-17). However, a clear understanding of the role of sphingolipid metabolism and, in particular, the mechanisms by which sphingolipid metabolites influence physiological processes in this organism has been hampered by an incomplete knowledge of the chemical structures of endogenous Drosophila sphingolipids and their metabolic products.Previously, we found that the Drosophila free sphingoid bases or long chain bases (LCBs) are composed largely of C 14 -and C 16 -sphingosine and dihydrosphingosine (18). In the current study, we have identified a second family of sphingolipids recognized by their differential separation on HPLC compared with known Drosophila sphingolipid species. Mass spectrometry approaches were used to characterize the structures of these unknown lipids as C 14 -and C 16 -sphingadienes with D-4,6 conjugated double bonds and to further identify a family of related lipids built upon the same D Abbreviations: dsRNA, double-stranded RNA; LCB, long...

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Section: Discussionmentioning

confidence: 99%

Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes

Fyrst¹,

Zhang

Herr

et al. 2008

Journal of Lipid Research

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“…These GSLs can be roughly divided into two groups: one with straight complex GSLs, such as those found in flies, the nematode, the blood fluke, and the lamp shell, and those with branching complex GSLs. Complex GSLs with more than seven sugar residues have been reported as follows: GlcNAcβ1-3Galβ1-3GalNAcα1-4GalNAcβ1-4GlcNAcβ1-3Manβ1-4Glcβ1-Cer (At 7 Cer) from the fly C. vicina [11]; At 7 Cer, VII 3 -β-GalNAc-At 7 Cer (At 8 Cer), and VIII 3 -β-Gal-At 8 Cer (At 9 Cer) from the fly L. caesar [10]; Fucα3GalNAcβ4(Fucα3)GlcNAcβ3GlcNAcβ3GalNAcβ4GlcβCer, Fucα3GalNAcβ4(Fucα2Fucα3)GlcNAcβ3GlcNAcβ3GalNAcβ4GlcβCer, Fucα3GalNAcβ4(Fucα2Fucα2Fucα3)GlcNAcβ3GlcNAcβ3GalNAcβ4GlcβCer, and Fuc1-4(Fuc1-3)GlcNAc1-2Fuc1-4(Fuc1-3)GlcNAc1-2Fuc1-4(Fuc1-3)GlcNAc1-2Fuc1-4(Fuc1-3)GlcNAc1-3GalNAc1-3GalNAc1-4Glc1-Cer from the blood fluke [12–14]; Gal4Meβ1-3GalNAcβ1-3Fucα1-4GlcNAcβ1-2Manα1-3(Xylβ1-2)Manβ1-4Glcβ1-Cer (GL-1) from the bivalve C. sandai [15]; Fuc3Meα1-2Xyl3Meβ1-4(GalNAc3Meα1-3)Fucα1-4GlcNAcβ1-2Manα1-3(Xylβ1-2)Manβ1-4Glcβ1-Cer (Lipid III) from the bivalves H. schlegeli and M. lusoria [16, 17]; and GlcNAc1-3(Fuc3Meα1-2)Gal1-4GalNAc1-3[GalNAc3Me1-3(Fucα1-2)Gal1-2]Galβ1-3Galβ1-4Glcβ1-Cer from the oyster [5]. All of these GSLs, with the exception of those found in the flies, contain a branching sugar chain and at least one fucose residue.…”

Section: Discussionmentioning

confidence: 99%

“…This study of the entire GSL structure in A. franciscana showed that the ceramide composition is common among nearly all neutral GSLs, irrespective of the length of the sugar chain, with the exception of CMS, which contains hydroxy fatty acid, similar to millipedes [21], but not to flies such as L. caesar and C. vicina [6, 7, 10, 11, 36]. In arthropods, the dominant ceramide moieties are d16:1 and smaller amounts of d17:1 as sphingoid; C22:0 and smaller amounts of C18:0 as fatty acid in A. franciscana ; d17:1 and smaller amounts of branched d18:1 as sphingoid; C22:0 and smaller amounts of C23:0/C24:0 as fatty acid in the millipede; d14:1 and smaller amounts of d16:1 as sphingoid; C20:0 and smaller amounts of C18:0/C22:0 as fatty acid in the flies and in the High Five insect cell line derived from the cabbage looper Trichoplusia ni [37].…”

Section: Discussionmentioning

confidence: 99%

“…In fact, there are relatively few reports that detail the structural analyses of complex GSLs in invertebrates. Complex GSLs have been identified in the green-bottle fly L. caesar and the blowfly C. vicina [10, 11], the human blood fluke Schistosoma mansoni [12–14], the bivalves Corbicula sandai [15] and Hyriopsis schlegeli [16], the seawater bivalve Meretrix lusoria [17], and the oyster Ostrea gigas [5]. …”

Section: Introductionmentioning

confidence: 99%

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Biochemical studies on sphingolipids of Artemia franciscana: complex neutral glycosphingolipids

et al. 2012

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Brine shrimp are primitive crustacean arthropodal model organisms, second to daphnia, which can survive in high-salinity environments. Their oviposited cysts, cuticle-covered diapausing eggs, are highly resistant to dryness. To elucidate specialties of brine shrimp, this study characterized glycosphingolipids, which are signal transduction-associated material. A group of novel and complex fucosyl glycosphingolipids were separated and identified from cysts of the brine shrimp Artemia franciscana by repeated lipid extraction, alkaline methanolysis, acid treatment, successive column chromatography, and post-source decay measurements by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Structures of the glycosphingolipids were elucidated by conventional structural characterization and mass spectrometry, and the compounds were identified as GlcNAcβ1-3GalNAcβ1-4(GlcNAcα1-2Fucα1-3)GlcNAcβ1-3Manβ1-4Glcβ1-Cer, GalNAcβ1-4(Fucα1-3)GlcNAcβ1-3GalNAcβ1-4(GlcNAcα1-2Fucα1-3)GlcNAcβ1-3Manβ1-4Glcβ1-Cer, and GalNAcβ1-4(GlcNAcα1-2Fucα1-3)GlcNAcβ1-3GalNAcβ1-4(GlcNAcα1-2Fucα1-3)GlcNAcβ1-3Manβ1-4Glcβ1-Cer. These compounds also contained a branching, non-arthro-series disaccharide with an α-GlcNAc terminus, similar to that found in a previously reported ceramide hexasaccharide (III3(GlcNAcα2Fucα)-At4Cer). The glycans within these complex GSLs are longer than reported glycans of the animal kingdom containing α-GlcNAc terminus. These complex GSLs as well as the longest GSL with ten sugar residues, ceramide decasaccharide (CDeS), contain the fucosylated LacdiNAc sequence reported to associate with parasitism/immunosuppression and the α-GlcNAc terminus reported to show a certain antibacterial effect in other reports. CDeS, the longest GSL of this species, was found in the highest amount, which indicates that CDeS may be functionally important.Electronic supplementary materialThe online version of this article (doi:10.1007/s10719-012-9436-8) contains supplementary material, which is available to authorized users.

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“…Detailed chemical constituents of insect sphingolipids were examined with glycosphingolipids from two species, Calliphora vicina (25)(26)(27) and Lucilia caesar (28)(29)(30). The structures of the LCBs from the dipteran sphingolipids were C 14 -and C 16 -sphingenine in L. caesar and C 14 -sphingenine in C. vicina, clearly different from those of the C. formosanus soldier frontal gland secretions, and free ceramides were not reported.…”

Section: Discussionmentioning

confidence: 99%

Novel free ceramides as components of the soldier defense gland of the Formosan subterranean termite (Coptotermes formosanus)

Ohta

Matsuura

Henderson

et al. 2007

Journal of Lipid Research

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Of the lipid extracts of the defense secretion from the Formosan subterranean termite, Coptotermes formosanus Shiraki, on high-performance thin-layer chromatography analysis, no glycolipids or phospholipids were detected, but free fatty acids and three novel ceramides were found (termed TL-1, TL-2, and TL-3). Free fatty acids were confirmed to be lignoceric acid (C24:0) and hexacosanoic acid (C26:0), as described previously [Chen, J., G. Henderson, and R. A. Laine. 1999. Lignoceric acid and hexacosanoic acid: major components of soldier frontal gland secretions of the Formosan subterranean termite (Coptotermes formosanus). J. Chem. Ecol. 25: 817-824]. TL-1, TL-2, and TL-3 were characterized as ceramides differing in hydrophobicity based on results of matrix-assisted laser desorption-ionization timeof-flight mass spectrometry analysis, mild alkaline treatment, GC-MS analysis of fatty acid methylesters, and GC-MS analysis of sphingoid long-chain bases (LCBs) as trimethylsilyl derivatives. Fatty acids in TL-1 and TL-2 were C18:0, C20:0, and C22:0, and those in TL-3 were 2-hydroxy C18:0, C20:0, and C22:0. The most predominant LCB in TL-2 was a novel trihydroxy C 14 -sphingosine, 1,3,9-trihydroxy-2-amino-6-tetradecene. TL-3 contained C 18 -sphinganine and two kinds of novel sphingadienines, 1,3-dihydroxy-2-amino-7,10-hexadecadiene and 1,3-dihydroxy-2-amino-11,14-eicosadiene. Although examination of the biological activities of these novel ceramides was beyond the scope of these studies, because of the minuscule quantities available from termite secretions, it will be interesting in the future to synthesize these molecules for biological testing. Many termite species, including the Formosan subterranean termite, Coptotermes formosanus Shiraki, have a soldier caste that is morphologically and physiologically specialized for defense (1). The physiological defense strategies are used by mechanically and chemically armed soldier termites. Weapons of the soldiers include mandibles modified for crushing and, most interesting, a defense secretion sprayed from its frontal gland, ejected from a foramen at the front of the head (2). The secretion has several properties, including immobilization, acting like a glue, and as an irritant against predators such as ants. The secretion apparently contains an unidentified alarm pheromone that repels workers and attracts soldiers (3). Furthermore, chemical signals in the secretion may stimulate workers exposed to the fluid to morph into soldiers during their next two molts (4). Chemical analyses of the defense gland secretions from the families Rhinotermitidae and Termitidae have revealed an impressive diversity of chemical components: monoterpenes, diterpenes, sesquiterpenes, quinones, macrocyclic lactones, alkanes, alkenes, nitroalkenes, vinyl ketones, and aldehydes (5, 6).In Coptotermitinae, chemical analyses of the frontal gland components have been performed in only a few species. A heterogeneous suspension of n-alkanes and mucopolysaccharides was reported in Coptotermes l...

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Studies on Glycosphingolipids in Larvae of the Green-Bottle Fly, Lucilia caesar: Two Neutral Glycosphingolipids having Large Straight Oligosaccharide Chains with Eight and Nine Sugars1

Cited by 25 publications

References 0 publications

Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes

Identification and characterization by electrospray mass spectrometry of endogenous Drosophila sphingadienes

Biochemical studies on sphingolipids of Artemia franciscana: complex neutral glycosphingolipids

Novel free ceramides as components of the soldier defense gland of the Formosan subterranean termite (Coptotermes formosanus)

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