Third-party-funded project
Title:
Fumonisins and their degradation products in food: Studies on the occurrence, stereochemistry, importance and mode of action.
Project management at the University of Würzburg:
Participating scientists:
Abstract:
Research activities in the field of mycotoxins include studies of the structure, occurrence, biosynthesis, metabolism and mode of action of fumonisins, a recently discovered new class of mycotoxins, predominantly found on yellow corn. Based on the on-line coupling of high-performance liquid chromatography and electrospray-ionization tandem mass spectrometry (HPLC-ESI-MS/MS) sensitive and highly selective methods for the detection of fumonisins and hydrolyzed fumonisins in food were developed. Of importance are also reaction products, e.g. N-carboxymethyl-fumonisins, which are formed during food manufacturing processes. During our studies on the mode of action of fumonisins, we showed for the first time that hydrolyzed fumonisins HFBx are not only inhibitors of the ceramide synthase but also substrates of the enzyme being converted to N-acyl-fumonisins in-vitro and in-vivo. The toxicity of the N-acyl-metabolites was evaluated using HT29 cells and the “brine-shrimp”-bioassay. The new metabolites were more toxic than FB1 or HFB1 and did not induce apoptosis.
For the determination of the absolute configuration of fumonisins circular dichroism spectroscopy was used. Based on the exciton-chirality method a sensitive and reliable procedure for the stereochemical assignment was developed. With this method, the stereochemistry of FB1 was determined to be 2S, 3S, 5R and that of FB3 to be 2S, 3S. The TCA-side chains of fumonisins are R-configured.
Key words:
Fumonisins
Mycotoxins
Analysis
Degradation products
Metabolism
Absolute configuration
Mode of action
Stereochemistry
Projekt period:
from 08.1996 to 12.2002
Funding institution:
DFG ,Granting date: 1.07.1996
Publications:
- Lukacs, Z.; Schaper, S.; Herderich, M.; Schreier, P.; Humpf, H.-U..
(1996). Identification and Determination of Fumonisin FB1 and FB2 in Corn and Corn Products by High Performance Liquid Chromatography - Electrospray-Ionization Tandem Mass Spectrometry (HPLC-ESI-MS/MS). (monograph)
- Hartl, M.; Humpf, H.-U..
(1998). Assigning the Absolute Configuration of Fumonisins by the Circular Dichroism Exciton Chirality Method. (monograph)
- Humpf, H.-U.; Schmelz, E.-M.; Meredith, F. I.; Vesper, H.; Vales, T. R.; Wang, E.; Menaldino, D. S.; Liotta, D. C.; Merill, A. H., Jr..
(1998). Acylation of Naturally Occurring and Synthetic 1-Deoxysphinganines by Ceramide Synthase. Formation of N-Palmitoyl-Aminopentol Produces a Toxic Metabolite of Hydrolyzed Fumonisin, AP1, and a New Category of Ceramide Synthase Inhibitor. (monograph)
- Becker, M.; Degelmann, P.; Herderich, M.; Schreier, P.; Humpf, H.-U..
(1998). High-Performance Liquid Chromatography-Electrospray Ionisation-Tandem Mass Spectrometry (HPLC-ESI-MS/MS) for the Analysis of Ochratoxin. (monograph)
- Degelmann, P.; Becker, M.; Humpf, H.-U..
(1999). Determination of Ochratoxin A in Beer by High-Performance Liquid Chromatography. (monograph)
- Hartl, M.; Herderich, M.; Humpf, H.-U..
(1999). Rapid Determination of Fumonisin FB1 in Corn Products by High-Performance Liquid Chromatography-Electrospray Mass Spectrometry (HPLC-ESP-MS). (monograph)
- Hartl, M.; Humpf, H.-U..
(1999). Simultaneous Determination of Fumonisin B1 and Hydrolyzed Fumonisin B1 in Corn Products by Liquid Chromatography-Electrospray Ionization Mass Spectrometry (HPLC-ESI-MS). (monograph)
- Hartl, M.; Humpf, H.-U..
(2000). Toxicity Assessment of Fumonisins Using the Brine Shrimp (Artemia salina) Bioassay. (monograph)
- Seefelder, W.; Hartl, M.; Humpf, H.-U..
(2001). Determination of N-(Carboxymethyl)fumonisin B1 in Corn Products by Liquid Chromatography/Electrospray Ionization- Mass Spectrometry. (monograph)
- Seefelder, W.; Humpf, H.-U.; Schwerdt, G.; Freudinger, R.; Gekle, M..
(2001). Induction of Apoptosis in Cultured Human Proximal Tubule Cells by Fumonisins and Fumonisin Metabolites. (monograph)
- Hartl, M.; Humpf, H.-U..
(2001). Combined Synthetic/CD Strategy for the Stereochemical Assignment of the Tricarballylic Acid Side Chain of Fumonisin B1. (monograph)
- Seefelder, W.; Gossmann, M.; Humpf, H.-U..
(2002). Analysis of Fumonisin FB1 in Fusarium proliferatum Infected Asparagus Spears and Garlic Tubers from Germany by Liquid Chromatography/Electrospray Ionization-Mass Spectrometry. (monograph)
- Seefelder, W.; Schwerdt, G.; Freudinger, R.; Gekle, M.; Humpf, H.-U..
(2002). A simple high-performance liquid chromatography/electrospray ionization-mass spectrometry (HPLC-ESI-MS) method for the quantification of sphingosine and sphinganine in cell cultures exposed to fumonisins. (monograph)
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