Preparation of 3-O-, 5-O- and N-palmitoyl derivatives of fumonisin B1 toxin and their characterisation with NMR and LC-HRMS methods

Angeli, Cserne; Nagy, Tamás Milán; Horváth, Lajos; Varga, Mónika; Szekeres, András; Tóth, Gábor; Janáky, Tamás; Szolomájer, János; Kovács, Melinda; Kövér, Katalin E.; Bartók, Tibor

doi:10.1080/19440049.2022.2116112

Cited by 3 publications

(2 citation statements)

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“…Since the discovery of the first fumonisins (FB1 and fumonisin B2) in 1988 [21,22], thirty fumonisins have been structurally identified (groups A, B, C, and P) [1,23,24]. In addition, nearly hundred fumonisins have been detected by HPLC/MS and MS/MS techniques [25][26][27][28][29], including O-acyland N-acyl-FB1 derivatives [30][31][32]. The importance of O-acylated-FB1 toxins was further enhanced by the fact that these metabolites have also been observed in corn following natural infection in Italy [33].…”

Section: Introductionmentioning

confidence: 99%

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Interaction of Fumonisin B1, N-Palmitoyl-Fumonisin B1, 5-O-Palmitoyl-Fumonisin B1, and Fumonisin B4 Mycotoxins with Human Serum Albumin and Their Toxic Impacts on Zebrafish Embryos

Csenki

Bartók²,

Bock

et al. 2023

Biomolecules

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Fumonisins are frequent food contaminants. The high exposure to fumonisins can cause harmful effects in humans and animals. Fumonisin B1 (FB1) is the most typical member of this group; however, the occurrence of several other derivatives has been reported. Acylated metabolites of FB1 have also been described as possible food contaminants, and the very limited data available suggest their significantly higher toxicity compared to FB1. Furthermore, the physicochemical and toxicokinetic properties (e.g., albumin binding) of acyl-FB1 derivatives may show large differences compared to the parent mycotoxin. Therefore, we tested the interactions of FB1, N-palmitoyl-FB1 (N-pal-FB1), 5-O-palmitoyl-FB1 (5-O-pal-FB1), and fumonisin B4 (FB4) with human serum albumin as well as the toxic effects of these mycotoxins on zebrafish embryos were examined. Based on our results, the most important observations and conclusions are the following: (1) FB1 and FB4 bind to albumin with low affinity, while palmitoyl-FB1 derivatives form highly stable complexes with the protein. (2) N-pal-FB1 and 5-O-pal-FB1 likely occupy more high-affinity binding sites on albumin. (3) Among the mycotoxins tested, N-pal-FB1 showed the most toxic effects on zebrafish, followed by 5-O-pal-FB1, FB4, and FB1. (4) Our study provides the first in vivo toxicity data regarding N-pal-FB1, 5-O-pal-FB1, and FB4.

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Section: Introductionmentioning

confidence: 99%

“…Currently, no data are available regarding the in vivo toxicity of Nand O-acyl-FB1 derivatives. In recent years, we have successfully isolated/produced N-palmitoyl-FB1 (N-pal-FB1), 5-O-palmitoyl-FB1 (5-O-pal-FB1), and fumonisin B4 (FB4) toxins (Figure 1) [32]. Thus, it is possible now to examine their in vivo toxicity compared to FB1.…”

Section: Introductionmentioning

confidence: 99%

Interaction of Fumonisin B1, N-Palmitoyl-Fumonisin B1, 5-O-Palmitoyl-Fumonisin B1, and Fumonisin B4 Mycotoxins with Human Serum Albumin and Their Toxic Impacts on Zebrafish Embryos

Csenki

Bartók²,

Bock

et al. 2023

Biomolecules

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Fumonisin distorts the cellular membrane lipid profile: A mechanistic insight

Ali,

Szabó

2024

Toxicology

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Matrix Effects of Different Water Types on the Efficiency of Fumonisin B1 Removal by Photolysis and Photocatalysis Using Ternary- and Binary-Structured ZnO-Based Nanocrystallites

Jevtić¹,

Jakšić

Merkulov

et al. 2023

Catalysts

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Several ternary- and binary-structured ZnO-based nanocrystallites (Zn2SnO4, Zn2TiO4, ZnO/SnO2, ZnO/TiO2) were synthesized by the solid-state method and first tested as photocatalysts in the removal of fumonisin B1 (FB1) under UV irradiation. The phase composition and nanocrystalline dimensions (50–80 nm) were confirmed by X-ray diffraction and Raman analyses. Similar preparation procedures applied in the case of binary structures resulted in their uniform morphology consisting of spherical particles ranging from 100 nm to 1 µm in size. However, higher synthesis temperatures of ternary oxides contributed to the growth of particles up to 10 µm. The optical energy bands of the examined photocatalysts were in the range of 3.08–3.36 eV. The efficiency of photocatalysis was compared with the efficiency of direct and indirect (sensitized by UV/H2O2 or UV/S2O82-) photolysis. The matrix effect of the different water types (Danube River, ground, and tap water) on the removal efficiency of FB1 was investigated by applying direct and indirect photolysis, as well as in the presence of the Zn2SnO4 photocatalyst. The effects of inorganic anions (Cl-, NO3-, HCO3- and SO42-), cations (Ca2+ and Mg2+), and humic acid were also investigated, since they were identified as a major species in tap, ground, and river water.

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Preparation of 3-O-, 5-O- and N-palmitoyl derivatives of fumonisin B₁ toxin and their characterisation with NMR and LC-HRMS methods

Cited by 3 publications

References 30 publications

Interaction of Fumonisin B1, N-Palmitoyl-Fumonisin B1, 5-O-Palmitoyl-Fumonisin B1, and Fumonisin B4 Mycotoxins with Human Serum Albumin and Their Toxic Impacts on Zebrafish Embryos

Interaction of Fumonisin B1, N-Palmitoyl-Fumonisin B1, 5-O-Palmitoyl-Fumonisin B1, and Fumonisin B4 Mycotoxins with Human Serum Albumin and Their Toxic Impacts on Zebrafish Embryos

Fumonisin distorts the cellular membrane lipid profile: A mechanistic insight

Matrix Effects of Different Water Types on the Efficiency of Fumonisin B1 Removal by Photolysis and Photocatalysis Using Ternary- and Binary-Structured ZnO-Based Nanocrystallites

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