An epimer of deoxynivalenol: purification and structure identification of 3-epi-deoxynivalenol

Abstract

In an investigation of deoxynivalenol (DON)-transformation products by Devosia mutans 17-2-E-8, the major product was identified as 3-epi-DON. This DON-transformation product was analysed by liquid chromatography and identified by congruent retention time and UV/Vis spectrum, as well as mass spectrometric data. Nuclear magnetic resonance (NMR) experiments including correlation spectroscopy (COSY), heteronuclear single quantum coherence (HSQC) and nuclear overhauser effect (NOE) were conducted for structural characterisation of 3-epi-DON. High-speed counter-current chromatography (HSCCC) was applied to scale up the separation of 3-epi-DON from DON in a D. mutans 17-2-E-8 culture. From the culture where 100 mg DON was applied, 56 mg of 3-epi-DON (purity of 96.8%) was obtained from the HSCCC. The purified 3-epi-DON will be used for toxicological characterisation studies of this chemical.

Keywords:

• Deoxynivalenol (DON)
• 3-epi-deoxynivalenol (3-epi-DON)
• Devosia mutans
• bacterial culture
• high-speed counter-current chromatography (HSCCC)
• liquid chromatography-mass spectrometry (LC-MS)
• nuclear magnetic resonance (NMR)
• correlation spectroscopy (COSY)
• heteronuclear single quantum coherence (HSQC)
• nuclear overhauser effect (NOE)

Additional information

Funding

This work was supported by Agriculture and Agri-Food Canada (project #1027).