Analysis of Palmitoyl Apo-astaxanthinals, Apo-astaxanthinones, and their Epoxides by UHPLC-PDA-ESI-MS

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Abstract

Food products enriched with fatty acid-esterified xanthophylls may result in deviating dietary apo-carotenoids. Therefore, free astaxanthin and its mono- and dipalmitate esters were subjected to two degradation processes in a methanolic model system: light-accelerated autoxidation and hypochlorous acid/hypochlorite (HOCl/OCl–) bleaching. Reversed phase ultrahigh-performance liquid chromatography photodiode array with in-line electrospray ionization mass spectrometry (RP-UHPLC-PDA-ESI-MS) was used for assessment of degradation products. Apo-astaxanthinals and -astaxanthinones containing 3 (apo-9) to 10 (apo-8') conjugated double bonds were found upon autoxidation for all three types of astaxanthin (except free apo-8'-astaxanthinal). Fragmentation of [M + H]+ and [M + Na]+ parent masses of apo-astaxanthins from dipalmitate astaxanthin indicated palmitate esterification. Astaxanthin monopalmitate degradation resulted in a mixture of free and palmitate apo-astaxanthins. HOCl/OCl– rapidly converted the astaxanthins into a mixture of epoxy-apo-9- and epoxy-apo-13-astaxanthinones. The palmitate ester bond was hardly affected by autoxidation, whereas for HOCl/OCl– the ester bond of the apo-astaxanthin palmitoyl esters was degraded.
Original languageEnglish
Pages (from-to)10254-10263
JournalJournal of Agricultural and Food Chemistry
Volume62
Issue number42
DOIs
Publication statusPublished - 2014

Keywords

  • beta-carotene degradation
  • mass-spectrometry
  • hypochlorous acid
  • haematococcus-pluvialis
  • products
  • myeloperoxidase
  • autoxidation
  • stability
  • oxidation
  • esters

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