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Isolation and characterization of acidic glycosphingolipids from the gill of the Pacific Salmon (Oncorhynchus keta): A novel hybrid-type ganglioside with isoglobo- and neolacto-Series

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Abstract

Monosialosyl gangliosides and sulfoglycolipids in the gill of pacific salmon, Oncorhynchus keta, have been prepared by solvent extraction and DEAE-Sephadex column chromatography. Acidic glycolipid bands (M1-M13) detected by thin layer chromatography were separated by Iatrobeads column chromatography and 13 components were characterized by TLC, compositional analysis, methylation analysis, chemical and enzymatic degradation, liquid secondary ion mass spectrometry and 1H nuclear magnetic resonance spectroscopy. In addition to the acidic glycolipids with known structures (SM4s, SM3, GM3, LM1, GM1b and V3αFuc,IV3βGalNAc-GM1a), two fractions (M11 and M13) of unknown monosialosyl gangliosides with TLC mobility slower than GM1a were isolated and characterized as having the following structure with a hybrid of isoglobo- and neolacto-series.

$$ \matrix {{{\text{NeuAc}}\alpha 2 - 3{\text{Gal}}\beta - 4{\text{GlcNAc}}\beta - 3{\text{Gal}}\alpha - 3{\text{Gal}}\beta - 4{\text{Glc}}\beta - {\text{Cer}}}} \\ {{\quad \quad 3}} \\ {{\quad \quad |}} \\ {{Fuc\alpha 1}} \ $$

Analysis of fatty acid indicated predominance of C24:1 fatty acid in the upper band (M11) and shorter chain saturated fatty acids in the lower band (M13). The tissue concentrations of M11 and M13 were 1.15 and 0.96 μmol/kg wet weight, respectively.

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Abbreviations

GalNAc:

N-acetylgalactosamine

GlcNAc:

N-acetylglucosamine

Hex:

hexose

HexNAc:

N-acetylhexosamine

NeuAc:

N-acetylneuraminic acid

Cer:

ceramide

LacCer:

Galβ1-4Glcβ1-1Cer

Gg3Cer:

GalNAcβ1-4Galβ1-4Glcβ1-1Cer

Gg4Cer, asialo GM1:

Galβ1-3GalNAcβ1-4Galβ1-4Glcβ1-1Cer

SM4s:

GalCer I3-sulfate

SM3:

LacCer II3-sulfate

GM3:

II3αNeuAc-LacCer

GM1a:

II3αNeuAc-Gg4Cer

GM1b:

IV3αNeuAc-Gg4Cer

LM1:

IV3αNeuAc-nLc

d18:1:

4-sphingenine

d18:0:

4-sphinganine

t18:0:

4-hydroxysphinganine

TLC:

thin layer chromatography

HPTLC:

high performance TLC

HPLC:

high performance liquid chromatography

TEAB:

triethanolamine carbonate

GLC:

gas–liquid chromatography

GC-MS:

gas chromatography-mass spectrometry

LSIMS:

liquid secondary ion mass spectroscopy

NMR:

nuclear magnetic resonance

COSY:

chemical shift correlated spectroscopy

Me2SO:

dimethyl sulfoxide

BSTFA:

bis-(trimethylsilyl)trifluoroacetamide

TMS:

tetramethylsilane

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Acknowledgments

I wish to thank Mrs. Michiko Ogawa for technical assistance, Dr. Keiko Tadano-Aritomi for measurement of negative-ion LSIMS, Dr. Naoko Tanaka for measurement of NMR and Professor Ineo Ishizuka for encouragement to proceed this work.

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  1. Research Center of Biomedical Analysis and Radioisotope, Teikyo University School of Medicine, 2-11-1, Kaga Itabashi-ku, Tokyo, 173-8605, Japan

    Yukio Niimura

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Correspondence to Yukio Niimura.

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The nomenclature system for lipids follows the recommendation of the Nomenclature Committee, International Union of the Pure and Applied Chemistry [1].

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Niimura, Y. Isolation and characterization of acidic glycosphingolipids from the gill of the Pacific Salmon (Oncorhynchus keta): A novel hybrid-type ganglioside with isoglobo- and neolacto-Series. Glycoconj J 23, 651–661 (2006). https://doi.org/10.1007/s10719-006-9002-3

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