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Title: Structure and natural occurrence of stereoisomers of the fumonisin B series mycotoxins
Authors: Gelderblom, WC 
Sewram, V 
Shephard, GS 
Snijman, PW 
Tenza, K 
van der Westhuizen, L 
Vleggaar, R 
Keywords: Fumonisins;corn;NMR;LC-MS;biosynthesis
Issue Date: 2007
Publisher: American Chemical Society
Source: J. Agric. Food Chem. 2007, 55, 11, 4388-4394
Journal: Journal of Agricultural and Food Chemistry 
Abstract: 1H and 13C NMR spectroscopy of both fumonisin B3 and B4, as well as high-performance liquid chromatography (HPLC) analysis of samples of fumonisin B3 used as standards, showed in each case the presence of two stereoisomers, which could not be separated by preparative chromatography. The 2,3-anti relative configuration for the two minor stereoisomers of fumonisin B3 and B4 was deduced from the NMR data, and their 2S,3R absolute configurations were established by application of Mosher's method using the fumonisin B3 sample. Samples of fumonisin B3 and B4 can contain between 10 and 40% of fumonisin B compounds of the 3-epi series. The 3-epi-FB3, determined by HPLC with fluorescence detection of the o-phthaldialdehyde derivative and confirmed by liquid chromatography-tandem mass spectrometry, was found to occur naturally in a range of maize samples at levels much lower than FB3 (< 20%). The identification of members of the 3-epi-fumonisin B series provides insight into the order and selectivity of steps in fumonisin biosynthesis.
Description: Article
DOI: 10.1021/jf070061h
Appears in Collections:HWSci - Journal Articles (DHET subsidised)

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