Preparation, Purification, and NMR Spectra of Some Mono- and Dihemisuccinates of the Trichothecene Mycotoxin Nivalenol

Article abstract of DOI:10.1021/jf00039a046

4,15-Diacetylnivalenol (DANIV) was produced in liquid culture and purified by fractionation over silica followed by preparative liquid chromatography.Hydrolysis gave nivalenol (NIV), a trichothecene mycotoxin found as a common contaminant in grain grown in the North Island of New Zealand.Reaction of NIV with succinic anhydride in the presence of n-butylboronic acid and (dimethylamino)pyridine produced a mixture of three mono- and two dihemisuccinates.These were separated by semipreparative HPLC.The major product was 3-hemisuccinyl-NIV (3-HS-NIV).Other products were 4-HS-NIV, 15-HS-NIV, 3,4-diHS-NIV, and 3,15-diHS-NIV. 3-HS-NIV was also produced by enzymatic hydrolysis of 3-HS-DANIV.