Structural elucidation of the neutral glycosphingolipids, mono-, di-, tri-and tetraglycosylceramides from the marine crab Erimacrus isenbeckii

Koji Kimura, Saki Itonori, Chiho Kajiwara, Noriyasu Hada, Tadahiro Takeda, Mutsumi Sugita

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The neutral glycosphingolipids, mono-, di-, tri-and tetraglycosylceramides (GL-1, GL-2, GL-3, GL-4a and GL-4b), were identified from whole tissues of the marine crab Erimacrus isenbeckii by successive column chromatography with ion exchange Sephadex (QAE-Sephadex), magnesium silicate (Florisil) and silicic acid (Iatrobeads) resins. Through component analysis, sugar analysis, methylation studies, exoglycosidase cleavage, and various chromatographic and spectrometric techniques, their structures were proposed to be as follows: GL-1, Glcβ1-1Cer; GL-2, Manβ1-4Glcβ1-1Cer; GL-3, Galβ1-3Manβ1-4Glcβ1-1Cer; and GL-4a and GL-4b, Gal3Mea1-4Galβ1-3Manβ1-4Glcβ1-1Cer. The main molecular species of the aliphatic moiety in each purified glycolipid were 18:0, 22:0, 22:1-d14:1 (fatty acid-sphingoid) and 18:0-d16:1 for GL-1; 18:0-d16:1 and 22:1-d14:1, d16:1 for GL-2; 22:1, 24:1-d16:1 for GL-3; 22:1, 24:1-d16:1 for GL-4a; and h22:1, h24:1-d16:1 for GL-4b, respectively. By immunological detection, an arthro-series glycosphingolipid (At3Cer; GlcNAcβ1-3Manβ1-4Glcβ1-1Cer) was also detected as a minor component. The characteristic arthro-series glycosphingolipid has been observed in most animals belonging to the phylum Arthropoda.

Original languageEnglish
Pages (from-to)269-280
Number of pages12
JournalJournal of Oleo Science
Volume63
Issue number3
DOIs
Publication statusPublished - 2014

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Neutral Glycosphingolipids
Column chromatography
Methylation
Fatty acids
Sugars
Silicates
Magnesium
Glycosphingolipids
Ion exchange
Animals
Resins
Tissue
Acids
Silicic Acid
Glycoside Hydrolases
Glycolipids
Fatty Acids
alpha-methylhomocysteine thiolactone
Florisil
sephadex

Keywords

  • Crab glycolipid
  • Crustacean glycolipid
  • Erimacrus isenbeckii
  • Glycosphingolipid
  • Mannolipid

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Structural elucidation of the neutral glycosphingolipids, mono-, di-, tri-and tetraglycosylceramides from the marine crab Erimacrus isenbeckii. / Kimura, Koji; Itonori, Saki; Kajiwara, Chiho; Hada, Noriyasu; Takeda, Tadahiro; Sugita, Mutsumi.

In: Journal of Oleo Science, Vol. 63, No. 3, 2014, p. 269-280.

Research output: Contribution to journalArticle

Kimura, Koji ; Itonori, Saki ; Kajiwara, Chiho ; Hada, Noriyasu ; Takeda, Tadahiro ; Sugita, Mutsumi. / Structural elucidation of the neutral glycosphingolipids, mono-, di-, tri-and tetraglycosylceramides from the marine crab Erimacrus isenbeckii. In: Journal of Oleo Science. 2014 ; Vol. 63, No. 3. pp. 269-280.
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abstract = "The neutral glycosphingolipids, mono-, di-, tri-and tetraglycosylceramides (GL-1, GL-2, GL-3, GL-4a and GL-4b), were identified from whole tissues of the marine crab Erimacrus isenbeckii by successive column chromatography with ion exchange Sephadex (QAE-Sephadex), magnesium silicate (Florisil) and silicic acid (Iatrobeads) resins. Through component analysis, sugar analysis, methylation studies, exoglycosidase cleavage, and various chromatographic and spectrometric techniques, their structures were proposed to be as follows: GL-1, Glcβ1-1Cer; GL-2, Manβ1-4Glcβ1-1Cer; GL-3, Galβ1-3Manβ1-4Glcβ1-1Cer; and GL-4a and GL-4b, Gal3Mea1-4Galβ1-3Manβ1-4Glcβ1-1Cer. The main molecular species of the aliphatic moiety in each purified glycolipid were 18:0, 22:0, 22:1-d14:1 (fatty acid-sphingoid) and 18:0-d16:1 for GL-1; 18:0-d16:1 and 22:1-d14:1, d16:1 for GL-2; 22:1, 24:1-d16:1 for GL-3; 22:1, 24:1-d16:1 for GL-4a; and h22:1, h24:1-d16:1 for GL-4b, respectively. By immunological detection, an arthro-series glycosphingolipid (At3Cer; GlcNAcβ1-3Manβ1-4Glcβ1-1Cer) was also detected as a minor component. The characteristic arthro-series glycosphingolipid has been observed in most animals belonging to the phylum Arthropoda.",
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AU - Kajiwara, Chiho

AU - Hada, Noriyasu

AU - Takeda, Tadahiro

AU - Sugita, Mutsumi

PY - 2014

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AB - The neutral glycosphingolipids, mono-, di-, tri-and tetraglycosylceramides (GL-1, GL-2, GL-3, GL-4a and GL-4b), were identified from whole tissues of the marine crab Erimacrus isenbeckii by successive column chromatography with ion exchange Sephadex (QAE-Sephadex), magnesium silicate (Florisil) and silicic acid (Iatrobeads) resins. Through component analysis, sugar analysis, methylation studies, exoglycosidase cleavage, and various chromatographic and spectrometric techniques, their structures were proposed to be as follows: GL-1, Glcβ1-1Cer; GL-2, Manβ1-4Glcβ1-1Cer; GL-3, Galβ1-3Manβ1-4Glcβ1-1Cer; and GL-4a and GL-4b, Gal3Mea1-4Galβ1-3Manβ1-4Glcβ1-1Cer. The main molecular species of the aliphatic moiety in each purified glycolipid were 18:0, 22:0, 22:1-d14:1 (fatty acid-sphingoid) and 18:0-d16:1 for GL-1; 18:0-d16:1 and 22:1-d14:1, d16:1 for GL-2; 22:1, 24:1-d16:1 for GL-3; 22:1, 24:1-d16:1 for GL-4a; and h22:1, h24:1-d16:1 for GL-4b, respectively. By immunological detection, an arthro-series glycosphingolipid (At3Cer; GlcNAcβ1-3Manβ1-4Glcβ1-1Cer) was also detected as a minor component. The characteristic arthro-series glycosphingolipid has been observed in most animals belonging to the phylum Arthropoda.

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KW - Mannolipid

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