Rapid and selective screening for toxic phorbol esters in Jatropha curcas seed oil using high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry

J Chromatogr A. 2019 Jul 19:1597:63-75. doi: 10.1016/j.chroma.2019.03.015. Epub 2019 Mar 11.

Abstract

Jatropha curcas L. is an inedible plant whose seed oil is an interesting source for biodiesel production. Seed cake, the main byproduct remaining (about 70% w/w) after the oil extraction process, has a high nutritional value but the presence in Jatropha curcas seed of phorbol esters (PEs), a family of toxic compounds with a tigliane skeleton, prevents application of seed cake and other byproducts (e.g. glycerin) in animal feed without an efficient detoxification. Considering the high toxicity of PEs, it is important to have a sensitive analytical method to evaluate the presence of these compounds in Jatropha curcas derivatives. In this paper we present the study of the ESI-MS/MS fragmentation pattern of the [M+Na]+ ion at m/z 733.5 of the six known PEs, namely Jatropha factors (JFs) C1-C6, which allowed to tentatively identify a series of characteristic and specific fragment ions useful to reveal the presence of JFs in Jatropha curcas seed oil, distinguish them from each other, and identify new PEs (J1-J4). Moreover, the substitution of the usual acetonitrile/water as mobile phase with a mixture of methanol/water (85:15, v/v) allowed to increase the signal of the sodium adduct of about 50-fold during the HPLC-ESI-MS/MS analysis.

Keywords: HPLC-ESI-MS/MS; Jatropha curcas L.; Phorbol esters; Seed oil.

MeSH terms

  • Animal Feed / adverse effects*
  • Animal Feed / analysis
  • Animals
  • Biofuels
  • Chromatography, High Pressure Liquid*
  • Food Analysis / methods*
  • Glycerol / chemistry
  • Jatropha / chemistry
  • Phorbol Esters / analysis*
  • Plant Oils / chemistry*
  • Seeds / chemistry
  • Tandem Mass Spectrometry*

Substances

  • Biofuels
  • Phorbol Esters
  • Plant Oils
  • Glycerol