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Journal of lipid research1999; 40(12); 2271-2278;

Novel plasmalogalactosylalkylglycerol from equine brain.

Abstract: A novel galactosylalkylglycerol modified with a long-chain cyclic acetal at the sugar moiety, 3-O-(4'6'-plasmalogalactosyl) 1-O-alkylglycerol, was isolated from equine brain. The presence of cyclic acetal linkage, its linked position, and the length of the acetal chain of the natural plasmalo lipid were determined by proton NMR spectroscopy and fast-atom bombardment;-mass spectrometry, as well as gas chromatography;-mass spectrometry and gas;-liquid chromatography. To identify the isomeric stereostructure of the natural product, the plasmalo derivative was chemically synthesized from 3-O-galactosyl 2-O-acyl 1-O-alkyl glyceride through acetalization after deacylation. As a result, the direction and position of the acetal chain of the natural plasmalo lipid were characterized as an "endo"-type 4',6'-O-acetal derivative linked to galactoside by comparison with the NMR data of the synthesized product. The chain lengths of alkyl and acetal groups were C(14) for the former and C(16) and C(18) for the latter, and those for the latter group were mostly similar to those of plasmalogalactosyl ceramide, which was previously isolated from equine brain.
Publication Date: 1999-12-10 PubMed ID: 10588953
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  • Journal Article
  • Research Support
  • Non-U.S. Gov't

Summary

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The research article discusses the isolation of a new type of galactosylalkylglycerol from horse brain tissue. This unique molecule has a long-chain cyclic acetal modification and its structure was determined through various chemical analysis techniques.

Isolation of novel molecules

  • The novel molecule, officially named 3-O-(4’6′-plasmalogalactosyl) 1-O-alkylglycerol, was isolated from horse (equine) brain tissue. This type of molecule is unique due to the fact it is modified with a long-chain cyclic acetal at the sugar component.

Analysis of molecular structure

  • The structure of the novel molecule was determined using proton nuclear magnetic resonance (NMR) spectroscopy, fast-atom bombardment-mass spectrometry, gas chromatography-mass spectrometry, and gas-liquid chromatography.
  • These methods allowed the researchers to pinpoint the location and existence of the cyclic acetal linkage, the point at which this linkage was attached, and the specific length of the acetal chain.

Comparison with synthesized molecules

  • To further understand the structure of the new molecule, a plasmalo derivative was created in a laboratory setting. This synthetic molecule was formed from 3-O-galactosyl 2-O-acyl 1-O-alkyl glyceride, and was acetalized after deacylation.
  • When the NMR data of the synthesized plasmalo derivative was compared to the natural plasmalo lipid, the researchers were able to characterize the acetal chain in the latter as an “endo”-type 4′,6′-O-acetal derivative that was linked to galactoside.

Characteristics of the novel molecule

  • The scientists determined the lengths of the alkyl and acetal groups in the novel molecule to be C(14) and C(16) and C(18) respectively, with the acetal group lengths mostly matching those of plasmalogalactosyl ceramide, another molecule previously isolated from equine brain tissue.

Cite This Article

APA
Yachida Y, Kashiwagi M, Mikami T, Tsuchihashi K, Daino T, Akino T, Gasa S. (1999). Novel plasmalogalactosylalkylglycerol from equine brain. J Lipid Res, 40(12), 2271-2278.

Publication

ISSN: 0022-2275
NlmUniqueID: 0376606
Country: United States
Language: English
Volume: 40
Issue: 12
Pages: 2271-2278

Researcher Affiliations

Yachida, Y
  • Departments of Chemistry, Sapporo Medical University School of Medicine, Chuo-Ku S1 W17, Sapporo 060-8556, Japan.
Kashiwagi, M
    Mikami, T
      Tsuchihashi, K
        Daino, T
          Akino, T
            Gasa, S

              MeSH Terms

              • Animals
              • Brain Chemistry
              • Chromatography, Gel
              • Galactosylceramides / chemical synthesis
              • Galactosylceramides / isolation & purification
              • Glycolipids / isolation & purification
              • Glycosphingolipids / chemical synthesis
              • Glycosphingolipids / isolation & purification
              • Horses
              • Lipids / chemistry
              • Magnetic Resonance Spectroscopy
              • Spectrometry, Mass, Fast Atom Bombardment
              • Stereoisomerism

              Citations

              This article has been cited 2 times.
              1. Rizzo WB. Genetics and prospective therapeutic targets for Sjögren-Larsson Syndrome.. Expert Opin Orphan Drugs 2016 Apr;4(4):395-406.
                doi: 10.1517/21678707.2016.1154453pubmed: 27547594google scholar: lookup
              2. Hikita T, Tadano-Aritomi K, Iida-Tanaka N, Levery SB, Ishizuka I, Hakomori S. Cationic glycosphingolipids in neuronal tissues and their possible biological significance.. Neurochem Res 2002 Aug;27(7-8):575-81.
                doi: 10.1023/a:1020259630034pubmed: 12374192google scholar: lookup