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The glycosylceramides of the nematodeCaenorhabditis elegans contain an unusual, branched-chain sphingoid base

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Lipids

Abstract

Caenorhabditis elegans was cultured in semi-defined medium containing yeast extract, soy peptone, glucose, hemoglobin, Tween 80, and sitosterol. Monoglycosylceramides were chromatographically purified from nematode extracts. Their structures were elucidated with mass spectrometry, nuclear magnetic resonance spectroscopy, and analysis of methanolysis products of the parent cerebrosides. The glycosylceramides were unusual in that the only long-chain sphingoid base detected was aniso-branched compound with a C-4 double bond (i.e., 15-methyl-2-aminohexadec-4-en-1,3-diol). Glucose was the only sugar moiety detected. The fatty acids consisted of a series of primarily straint-chain, saturated, 2-hydroxylated C20–C26 acids; someiso-branched analogs also occurred. The sphingomyelins ofC. elegans were also hydrolyzed, and the sameiso-branched C17 compound was the only sphingoid base detected. This is the first structural analysis of a nematode glycosphingolipid and the first report of an organism in which the long-chain sphingoid bases are entirelyiso-branched.

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Abbreviations

CI/MS:

chemical ionization/mass spectroscopy

EI/MS:

electron impact/mass spectrometry

EtOH:

ethanol

FAME:

fatty acid methyl ester

GalCer:

galactosylceramide

GC/MS:

gas chromatography/mass spectrometry

GlcCer:

glucosylceramide

GLC:

gas-liquid chromatography

HPLC:

high-performance liquid chromatography

LCB:

long-chain sphingoid base

MeOH:

methanol

TLC:

thin-layer chromatography

TMS:

trimethylsilyl

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Author information

Authors and Affiliations

  1. Nematology Laboratory, ARS, USDA, Bldg. 011A, Room 153, BARC-West, 20705-2350, Beltsville, MD

    David J. Chitwood

  2. Insect Neurobiology and Hormone Laboratory, ARS, USDA, Bldg. 011A, Room 153, BARC-West, 20705-2350, Beltsville, MD

    William R. Lusby, Malcolm J. Thompson & Jan P. Kochansky

  3. Department of Chemistry, University of Warwick, Coventry, UK

    Oliver W. Howarth

Authors
  1. David J. Chitwood
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  2. William R. Lusby
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  3. Malcolm J. Thompson
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  4. Jan P. Kochansky
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  5. Oliver W. Howarth
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Additional information

Fatty acids are represented by a binumeric system in which the first number refers to the chain length, and the second number refers to the number of double bonds.

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Chitwood, D.J., Lusby, W.R., Thompson, M.J. et al. The glycosylceramides of the nematodeCaenorhabditis elegans contain an unusual, branched-chain sphingoid base. Lipids 30, 567–573 (1995). https://doi.org/10.1007/BF02537032

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  • DOI: https://doi.org/10.1007/BF02537032

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