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Double-bond location in long-chain polyunsaturated fatty acids by chemical lonization-mass spectrometry

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Lipids

Abstract

For determination of the double-bond position in polyunsaturated C24–30 fatty acids from marine organisms, methoxy derivatives were prepared. Diagnostic mass spectral fragment as well as molecular ion intensities were obtained by adjusting the ion source optics in the presence of ammonia at a lower source pressure than used conventionally. A lower detection limit was observed compared to conventional methane chemical ionization, which is a more favorable condition for capillary gas chromatography. Analysis of fatty acids from the spongeCalyx niceaensis showed the double-bond position of 8 unsaturated fatty acids, including two new ones. In addition, structural proof is provided for the presence of a new cyclopropane-containing fatty acid: 19,20-methylene-hexacosanoic acid.

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Abbreviations

GC-MS:

gas chromatography-mass spectrometry

CI-MS:

chemical ionization-mass spectrometry

VME:

vinylmethyl ether

HPLC:

high performance liquid chromatography

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Author information

Author notes

  1. Jan Lankelma

    Present address: Dept. of Oncology, Free University Hospital, V 1066 B. De Boelelaan 1117, 1007 MB, Amsterdam, The Netherlands

Authors and Affiliations

  1. Department of Chemistry, Stanford University, 94305, Stanford, CA

    Jan Lankelma, Eser Ayanoglu & Carl Djerassi

Authors
  1. Jan Lankelma
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  2. Eser Ayanoglu
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  3. Carl Djerassi
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Additional information

“Mass Spectrometry in Structural and Stereochemical Problems 262.” For preceding paper in this series, see Patterson, D.G., Haley, M.J., Midgley, J., and Djerassi, C., Org. Mass. Spectrom., submitted for publication.

Recipient of a travel grant from the Queen Wilhelmina Fund, The Netherlands Cancer Foundation

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Lankelma, J., Ayanoglu, E. & Djerassi, C. Double-bond location in long-chain polyunsaturated fatty acids by chemical lonization-mass spectrometry. Lipids 18, 853–858 (1983). https://doi.org/10.1007/BF02534561

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  • DOI: https://doi.org/10.1007/BF02534561

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