title: 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.
authors.affiliation: a Guelph Food Research Centre , Agriculture and Agri-Food Canada , Guelph, ON , Canada.
authors.forename: Jian Wei
authors.initials: JW
authors.lastname: He
authors.forename: Raymond
authors.initials: R
authors.lastname: Yang
authors.forename: Ting
authors.initials: T
authors.lastname: Zhou
authors.forename: Greg J
authors.initials: GJ
authors.lastname: Boland
authors.forename: Peter M
authors.initials: PM
authors.lastname: Scott
authors.forename: Genevieve S
authors.initials: GS
authors.lastname: Bondy
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003377:Countercurrent Distribution; D041921:Hyphomicrobiaceae / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D013056:Spectrophotometry, Ultraviolet; D014255:Trichothecenes / Q000737:chemistry* / Q000302:isolation & purification*
chemical_list: D014255:Trichothecenes; C007262:deoxynivalenol
keywords: 3-epi-deoxynivalenol (3-epi-DON); Deoxynivalenol (DON); Devosia mutans; bacterial culture; correlation spectroscopy (COSY); heteronuclear single quantum coherence (HSQC); high-speed counter-current chromatography (HSCCC); liquid chromatography-mass spectrometry (LC-MS); nuclear magnetic resonance (NMR); nuclear overhauser effect (NOE)