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Characterization of epoxy carotenoids by fast atom bombardment collision-induced dissociation MS/MS

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Lipids

Abstract

The characterization and structure of epoxy carotenoids possessing 5,6-epoxy, 5,8-epoxy and 3,6-epoxy end groups conjugated to the polyene chain were investigated using highenergy fast atom bombardment collision-induced dissociation MS/MS methods. In addition to [M-80]+, a characteristic fragment ion of an epoxy carotenoid, product ions resulting from the cleavage of C−C bonds in the polyene chain from the epoxy end group, such as m/z 181 (b ion) and 121 (c ion), were detected. On the other hand, diagnostic ions of m/z 286 (e-H ion) and 312 (f-H ion) were observed, not in the 5,6-epoxy or 5,8-epoxy carotenoid but in the 3,6-epoxy carotenoid. These fragmentation patterns can be used to distinguish 3,6-epoxy carotenoids from 5,6-epoxy or 5,8-epoxy carotenoids. The structure of an epoxy carotenoid, 3,6-epoxy-5,6-dihydro-7′,8′-didehydro-β,β-carotene-5,3′-diol (8), isolated from oyster, was characterized using FAB CID-MS/MS by comparing fragmentation patterns with those of related known compounds.

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Abbreviations

FAB CID-MS/MS:

fast atom bombardment collision-induced dissociation MS/MS

NBA:

nitrobenzyl alcohol

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Authors and Affiliations

  1. Research Institute for Production Development, 606-0805, Kyoto

    Takashi Maoka

  2. Kyoto Pharmaceutical University, 607-8414, Kyoto, Japan

    Yasuhiro Fujiwara

  3. Nagahama Institute of Bio-sciences and Technology, 526-0829, Shiga, Japan

    Keiji Hashimoto

  4. Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, 606-8501, Kyoto, Japan

    Naoshige Akimoto

Authors
  1. Takashi Maoka
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  2. Yasuhiro Fujiwara
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  3. Keiji Hashimoto
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  4. Naoshige Akimoto
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Correspondence to Naoshige Akimoto.

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Maoka, T., Fujiwara, Y., Hashimoto, K. et al. Characterization of epoxy carotenoids by fast atom bombardment collision-induced dissociation MS/MS. Lipids 39, 179–183 (2004). https://doi.org/10.1007/s11745-004-1217-3

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  • DOI: https://doi.org/10.1007/s11745-004-1217-3

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