Production of Fumonisin B and C Analogues by Several Fusarium Species

Abstract

Six strains of Fusarium verticillioides, two of F. oxysporum, one strain of F. proliferatum, and a strain of an unidentified species were cultured on maize patties and rice and evaluated for their ability to simultaneously produce fumonisin B (FB) and C (FC) series analogues. Fumonisins were quantified by LC-MS-MS using positive ion electrospray ionization. FC1 provided characteristic fragment ions at m/z 690, 672, 654, 532, 514, and 338 corresponding to sequential loss of H2O and tricarboxylic acid moieties from the alkyl backbone, while FC3 and FC4 provided equivalent product ions 16 and 32 amu lower than the corresponding FC1 fragments, respectively. All isolates cultured on maize produced FC4. All isolates except for that of F. proliferatum also produced FC1, and three of the six strains of F. verticillioides produced FC3. All isolates except those of F. oxysporum produced detectable amounts of FB1, FB2, and FB3. Isolates that produced fumonisin B analogues produced at least 10 fold more of the B series analogues than they did of the C series analogues. The results confirm that at least some strains of F. oxysporum produce FC, but not FB, fumonisin analogues and also suggest that the genetics and physiological regulation of fumonisin production may be more complicated than previously envisaged since some strains of F. verticillioides and F. proliferatum as well as the strain of the unidentified species can simultaneously produce both FB and FC analogues.

A fumonisin biosynthetic gene cluster in Fusarium oxysporum strain O-1890 and the genetic basis for B versus C fumonisin production

“…Precursor feeding experiments indicate that FB biosynthesis involves the condensation of alanine and a linear, 18-carbon polyketide (Branham and Plattner, 1993a). Given their structures, FCs are most likely formed by condensation of glycine and the 18-carbon polyketide (Sewram et al, 2005). Thus, it is likely that the FvFUM8 a-oxoamine synthase has higher substrate specificity for alanine while the FoFUM8 enzyme has higher specificity for glycine.…”

“…A, B, C and P fumonisins differ in structure by differences in the nitrogen function and by the length of the carbon backbone. For example, in B and C fumonisins the nitrogen function is a free amine, in A fumonisins it is an acetylated amine, and in P fumonisins it is a 3-hydroxypyridinium (Musser and Plattner, 1997;Sewram et al, 2005). In B fumonisins (FBs) the backbone is 20 carbon atoms long, whereas in C fumonisins (FCs) it is 19 carbon atoms long (Fig.…”

“…Although strains of F. oxysporum, which is considered by some to be a species complex (Baayen et al, 2000), do not typically produce fumonisins, there are several reports of fumonisin production by individual strains of this species (Abbas, 1995;Sewram et al, 2005;Seo et al, 1996). Strains of F. oxysporum isolated from carnation and asparagus in Korea are highly unusual in that not only do they produce fumonisins, but they produce predominantly FCs rather than FBs (Seo et al, 1996).…”

“…Strains of F. oxysporum isolated from carnation and asparagus in Korea are highly unusual in that not only do they produce fumonisins, but they produce predominantly FCs rather than FBs (Seo et al, 1996). FC production has been reported in F. verticillioides, F. proliferatum and some other species but at markedly lower levels than FB production (Branham and Plattner, 1993b;Sewram et al, 2005). In this study, we determined the nucleotide sequence of the FUM cluster in an FC-producing strain of F. oxysporum and used the sequence to examine whether different FUM8 orthologues can determine whether FB or FC production predominates in Fusarium.…”

Free and bound fumonisins in gluten‐free food products

“…These compounds are characterized by a 20 carbon aminopolyhydroxyalkyl chain diesterified with propane-1,2,3-tricarboxylic acid (tricarballylic acid (TCA)) ( Fig. 1) [1,2].…”