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Determining double-bond positions in monoenoic 2-hydroxy fatty acids of glucosylceramides by gas chromatography-mass spectrometry

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Lipids

Abstract

We applied a gas chromatography-mass spectrometry (GC-MS) method using dimethyl disulfide (DMDS) adducts and were able to determine the double-bond positions in monounsaturated 2-hydroxy fatty acids (2-HFA). 2-HFA methyl esters, prepared from the hydrolysate ofArabidopsis thaliana leaf glucosylceramides, were acetylated and methylthiolated. GC-MS analysis of the resulting DMDS adducts showed simple mass spectra with recognizable molecular ions and a series of key fragment ions indicating the original double-bond positions in the aliphatic chain. Based on this GC-MS elucidation, we confirmed thatArabidopsis leaf glucosylceramides have C22, C23, C24, C25, and C26 chain length 2-HFA with monounsaturation, and all their double bonds are placed at the n−9 position. This procedure is simple, time efficient, and highly sensitive.

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Abbreviations

DMDS:

dimethyl disulfide

GC-MS:

gas chromatography-mass spectrometry

2-HFA:

2-hydroxy fatty acid (Xh∶Y, 2-hydroxy fatty acid containing X carbons with Y double bonds

TLC:

thin-layer chromatography

References

  1. Falsone, G., Budzikiewicz, H., and Wendisch, D. (1987) Constituents ofEuphorbiaceae, 9 Comm. [1]. New Cerebrosides fromEuphorbia biglandulosa Desf.,Z. Naturforsch. 42b, 1476–1480.

    Google Scholar 

  2. Imai, H., Ohnishi, M., Kinoshita, M., Kojima, M., and Ito, S. (1995) Structure and Distribution of Cerebroside Containing Unsaturated Hydroxy Fatty Acids in Plant Leaves,Biosci. Biotechnol. Biochem. 59, 1309–1313.

    Article  CAS  Google Scholar 

  3. Renkonen, O. (1966) Individual Molecular Species of Phospholipids III. Molecular Species of Ox-Brain Lecithins,Biochim. Biophys. Acta 125, 288–309.

    CAS  Google Scholar 

  4. Yamamoto, K., Shibahara, A., Nakayama, T., and Kajimoto, G. (1991) Determination of Double-Bond Positions in Methylene-Interrupted Dienoic Fatty Acids by GC-MS as Their Dimethyl Disulfide Adducts,Chem. Phys. Lipids 60, 39–50.

    Article  CAS  Google Scholar 

  5. Imai, H. (1998) Glucocerebrosides Containing Unsaturated Hydroxy Fatty Acids inArabidopsis thaliana, inAdvances in Plant Lipid Research (Sánchez, J., Cerdá-Olmedo, E., and Martínez-Force, E., eds.), pp. 38–40, Universidad de Sevilla, Sevilla.

    Google Scholar 

  6. Ragnar, R., and Einar, S. (1960) Mass Spectrometric Studies VI. Methyl Esters of Normal Chain Oxo-, Hydroxy-, Methoxy- and Epoxy-acids,Ark. Kemi 15, 545–574.

    Google Scholar 

  7. Shibahara, A., Yamamoto, K., Nakayama, T., and Kajimoto, G. (1985) Rapid Determination of Double Bond Positions in Monounsaturated Fatty Acids by GC-MS and Its Application to Fatty Acid Analysis,J. Jpn. Oil Chem. Soc. 34, 618–625.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Biology, Faculty of Science, Konan University, 658-8501, Kobe, Japan

    Hiroyuki Imai

  2. General Testing Research Institute of Japan Oil Stuff Inspectors' Corporation, 658-0044, Kobe, Japan

    Kohei Yamamoto & Takao Nakayama

  3. Department of Clinical Nutrition, Osaka Prefectural College of Health Sciences, 583-8555, Habikino, Japan

    Akira Shibahara & Shuichi Miyatani

Authors
  1. Hiroyuki Imai
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  2. Kohei Yamamoto
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  3. Akira Shibahara
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  4. Shuichi Miyatani
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  5. Takao Nakayama
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Corresponding author

Correspondence to Hiroyuki Imai.

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Imai, H., Yamamoto, K., Shibahara, A. et al. Determining double-bond positions in monoenoic 2-hydroxy fatty acids of glucosylceramides by gas chromatography-mass spectrometry. Lipids 35, 233–236 (2000). https://doi.org/10.1007/BF02664774

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  • DOI: https://doi.org/10.1007/BF02664774

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