Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme

Bezuidenhout, S. Catherine; Gelderblom, Wentzel C. A.; Gorst-Allman, Charles P.; Horak, R. Marthinus; Marasas, Walter F. O.; Spiteller, Gerhard; Vleggaar, Robert

doi:10.1039/c39880000743

Cited by 575 publications

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“…The fumonisins, a new class of mycotoxins, have been isolated and characterized from toxic cultures of Fusarium moniloforme 1,2 and Fusarium proliferatum. 9 One of the first reports of the natural occurrence of the fumonisins described the identification of the fumonisins in corn from Transkei, Republic of South Africa.…”

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confidence: 99%

A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B₁ and B₂

1992

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Abstract.A thin layer chromatography (TLC) method was developed for the detection of fumonisin B 1 and B 2 in corn and corn-based feedstuffs. Finely ground samples were extracted with acetonitrile : water (1: 1), filtered, and applied to C 18 cleanup columns. The columns were washed with 1% aqueous KCl followed by acetonitrile : 1% aqueous KC1 (1:9), and the fumonisins were eluted with acetonitrile : water (7:3). The eluants were concentrated and spotted on reverse-phase C 18 TLC plates along with fumonisin B 1 and B 2 standards, and the plates were developed in methanol : 4% aqueous KCl (3:2). The fumonisins were visualized by spraying the TLC plates successively with 0.1 M sodium borate buffer, fluorescamine, and 0.01 M boric acid. The plates were then dried and examined under longwave ultraviolet light. Fumonisin B 1 and B 2 appeared as bright yellowish-green fluorescent bands at R f s of 0.5 and 0.1, respectively. The detection limit for the fumonisins on the TLC plate was 0.1 ppm in corn. Recoveries from spiked samples averaged >80%. The identification of the fumonisins was confirmed by hydrolyzing the parent compounds of B 1 and B 2 to their respective C 22 amino-alcohols and reexamining by TLC with the same visualizing reagents. This procedure was used to survey 193 corn samples collected from University of Missouri test plots in 1990 for fumonisin B,. Fumonisin B 1 was detected in 15% of the corn samples.The fumonisins, a new class of mycotoxins, have been isolated and characterized from toxic cultures of Fusarium moniloforme 1,2 and Fusarium proliferatum. 9 One of the first reports of the natural occurrence of the fumonisins described the identification of the fumonisins in corn from Transkei, Republic of South Africa. 12 Recent studies have shown fumonisin B 1 to be responsible for equine leukoencephalomalacia (ELEM) 5,6 and swine pulmonary edema. 3 In the United States, fumonisin-contaminated corn screenings have been associated with cases of ELEM 7-9,13 and swine pulmonary edema, 3,9 but only limited information is available on natural occurrence and levels of incidence of the fumonisins. A number of analytical procedures for fumonisins in corn and corn products, including thin layer chromatography (TLC), high performance liquid chromatography (HPLC), and gas chromatography/ mass spectroscopy (GC/MS), 8,10,12,13 are available, but all are of limited value or not readily available for extensive monitoring of fumonisin contamination in corn. In this report, a rapid and sensitive TLC procedure for detecting fumonisin B 1 and B 2 in corn and corn-based feeds is described. This procedure was used to document the natural occurrence of fumonisin B 1 and B 2 in Missouri's 1990 corn harvest. Received for publication October 7, 1991. Materials and methodsSample collection. Corn samples (approximately 450 g) were collected, as part of an ongoing mycotoxin monitoring program, from the University of Missouri experimental test plots. Samples were labeled by location and hybrid. Dry land test plots were located in ...

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confidence: 99%

A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B₁ and B₂

1992

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“…These new mycotoxins, characterized as bistricarballylic aminopolyol esters (Figure 1), were given the trivial name of fumonisins. Like the AAL toxins, the fumonisins are comprised of a family of structural congeners with differing levels of toxic activity (Bezuidenhout et al, 1988). Consumption of maize colonized by F. moniliforme was linked first to leukoencephalomalacia, a fatal disease of horses Gelderblom et al, 1988a), and subsequently to esophageal cancer in humans (Gelderblom et al, 1988b;Marasas et al, 1988b;Sydenham et al, 1990).…”

Section: Sphinganine Analog Mycotoxins (Sams)mentioning

confidence: 99%

Mycotoxins reveal connections between plants and animals in apoptosis and ceramide signaling

Gilchrist

1997

Cell Death Differ

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Plants undergo programmed cell death during development and disease in contexts that are functionally analogous to apoptosis in animals. Recent studies involving plant cell death induced by mycotoxins, pathogens and lethal mutations along with the cell-autonomous death during development now point to several conserved connections to apoptosis in animals. Morphological markers indicative of apoptosis recently reported in plants include TUNEL positive cells, DNA ladders, Ca 2+ -activated nucleosomal DNA cleavage, and formation of apoptotic-like bodies that occur in some but not all situations involving ordered cell death. In parallel studies with animal and plant cells treated with sphinganine analog mycotoxins our results indicate that the induction and inhibition of death may be mediated by ceramide-linked signaling systems. The presence and significance of ceramide-linked second messenger systems is well documented in animals but is virtually unknown in plants. Further research will discern the manner in which the important function of programmed cell death is conserved as well as diverged between the two kingdoms.

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“…They were first described by Bezuidenhout et al (1988) and Gelderblom et al (1988) and their structures were elucidated as aliphatic molecules resembling the sphingosines. The fumonisins cause a variety of symptoms in animals, such as leucoencephalomalacia in horses, pulmonary oedema in pigs or liver cancer in rats (Riley et al 1993).…”

Section: Introductionmentioning

confidence: 99%

A PCR‐ELISA for the detection of potential fumonisin producing Fusarium species

Grimm¹,

Geisen²

1998

Letters in Applied Microbiology

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C . G RI M M A ND R . G EI S EN . 1998. A PCR-ELISA for the detection of potential fumonisin producing Fusarium species has been developed, using the ribosomal ITS1 sequence as target. For this purpose, the sequences of the ITS1 regions of different fumonisin producing Fusarium species have been determined and compared to the sequences of fumonisin non-producing species. In general, the ITS1 sequences were highly homologous. However, some minor sequence polymorphisms were detected, which differentiates potential fumonisin producing Fusarium species from non-producing species. By using these sequence differences, a PCR-ELISA for potential fumonisin producing Fusarium species was developed. All other ubiquitously occurring food-borne fungi tested showed negative results with this test.

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Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme

Cited by 575 publications

References 0 publications

A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B₁ and B₂

A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B₁ and B₂

Mycotoxins reveal connections between plants and animals in apoptosis and ceramide signaling

A PCR‐ELISA for the detection of potential fumonisin producing Fusarium species

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Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme

Cited by 575 publications

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A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B1 and B2

A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B1 and B2

Mycotoxins reveal connections between plants and animals in apoptosis and ceramide signaling

A PCR‐ELISA for the detection of potential fumonisin producing Fusarium species

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A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B₁ and B₂

A Rapid, Sensitive Thin Layer Chromatography Procedure for the Detection of Fumonisin B₁ and B₂