Fumizol Ltd.

Szeged, Hungary

Fumizol Ltd.

Szeged, Hungary

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Kadar Z.,University of Szeged | Baji A.,University of Szeged | Zupko I.,University of Szeged | Bartok T.,University of Szeged | And 3 more authors.
Organic and Biomolecular Chemistry | Year: 2011

Stereoselective 1,4-Michael addition of azoimide to 17β-acetoxy- 5α-adrost-1-en-3-one was carried out to furnish a 1α-azido-3-ketone, which was reduced to give the 3β- and 3α-hydroxy epimers in a ratio of 5:2. The Cu(i)-catalyzed 1,3-dipolar cycloaddition of the major isomer to terminal alkynes afforded 1α-triazolyl derivatives, which were deacetylated to the corresponding 3β,17β-diols or oxidized to the analogous 3-ketones. However, the ability of the minor 1α,3α- azidoalcohol to undergo similar cyclization was found to be affected significantly by the steric bulk of the substituents on the alkyne reaction partner. All triazolyl compounds were tested in vitro on three malignant gynecological cell lines (HeLa, MCF7 and A2780). © The Royal Society of Chemistry 2011.


Bartok T.,Fumizol Ltd | Bartok T.,University of Szeged | Szecsi A.,Hungarian Academy of Sciences | Juhasz K.,Debrecen University | And 2 more authors.
Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment | Year: 2013

Following the earlier detection of six new esterified fumonisin B1 (EFB1) isomers containing three acyl groups in a Fusarium verticillioides-inoculated rice culture, it was assumed that linoleic, palmitic or oleic acid esterifies one of the free OH groups on the fumonisin backbone. On the basis of the results of our recent investigations we now propose that these EFB1 isomers are actually 3-O- and 5-O-acyl derivatives of FB1 (3-O-linoleoyl-FB1, 5-O-linoleoyl-FB1, 3-O-palmitoyl-FB1, 5-O-palmitoyl-FB1, 3-O-oleoyl-FB1 and 5-O-oleoyl-FB1). A F. verticillioides strain was identified that produced not only O-acyl-FB1 isomers, but also low amounts of three N-acyl derivatives (N-linoleoyl-FB1, N-palmitoyl-FB1 and N-oleoyl-FB1), which eluted from the HPLC column after the six O-acyl compounds and in the same sequence as for the O-acyl compounds. The characteristic positive and negative ESI-MS/MS spectra obtained after solid-phase extraction of the culture extract facilitated identification of these N-acyl-FB1 derivatives. The biosynthesis of N-palmitoyl-FB1 by F. verticillioides was verified by spiking the culture extract with synthetic N-palmitoyl-FB1. This is the first report of the separation and mass spectrometric identification of the six O-acyl- and three N-acyl-FB1 derivatives extracted from a F. verticillioides culture. © 2013 Taylor & Francis.


Varga J.,University of Szeged | Kocsube S.,University of Szeged | Szigeti G.,University of Szeged | Man V.,University of Szeged | And 4 more authors.
Acta Alimentaria | Year: 2012

Black mould rot caused by black Aspergilli is an important post-harvest disease of onion worldwide. Usually Aspergillus niger is cited as the causative agent based on morphological criteria. In this study, the mycobiota and fumonisin contamination of mouldy onion bulbs purchased in Hungary were examined. All except one of the examined mouldy samples were found to be contaminated with black Aspergilli, which could be isolated both from the outer dry and the inner fleshy scales of onion bulbs. Species assignment of the isolates was carried out using sequence analysis of part of the calmodulin gene. Sequence data revealed that all 35 black Aspergilli isolated from onions belong to the Aspergillus awamori species. The range of fumonisin isomers present in the onion samples was also examined using reversed-phase high-performance liquid chromatography/electrospray ionization-ion trap mass spectrometry. Two of the examined onion samples were found to be contaminated with fumonisins at a rate of about 0.3 mg kg-1. This is the first report on fumonisin contamination of onion bulbs. The fumonisin isomers observed include fumonisins B2-4, 3-epi-FB4, iso-FB1 (FB6) and an iso-FB2,3 form. The range of fumonisin isomers detected in the onion bulbs indicates that probably A. awamori is responsible both for mould rot and fumonisin contamination of onions in Hungary.


Bartok T.,Fumizol Ltd. | Tolgyesi L.,Eötvös Loránd University | Szecsi A.,Hungarian Academy of Sciences | Mesterhazy A.,Cereal Research Non Profit Ltd. | And 3 more authors.
Journal of Chromatographic Science | Year: 2014

Five previously unknown fumonisin mycotoxins (iso-FP1, iso-FP2,3a, iso-FP2,3b, FP4 and iso-FP 4) and three previously described FP analogues (FP1-3) were detected in a solid rice culture inoculated with Fusarium verticillioides. The fumonisins were characterized by high-performance liquid chromatography-electrospray ionization time-of-flight mass spectrometry (HPLC-ESI-TOFMS) and ion trap mass spectrometry (ITMS). The FP isomers were separated by using a flat gradient on a special, high-coverage C18, narrow-bore HPLC column (YMC-Pack J'sphere ODS H80), which was suggested for the separation of structural isomers. The verified structures of the FP1-3 mycotoxins, the relative retention times (by HPLC-ESI-TOFMS and ITMS), the exact masses of the molecular ions (by TOFMS) and the masses of the product ions, including the hydrocarbon backbones (by ITMS) of the new compounds, strongly suggested their structures. © 2013 The Author [2013]. Published by Oxford University Press. All rights reserved.


Kadar Z.,University of Szeged | Kovacs D.,University of Szeged | Frank E.,University of Szeged | Schneider G.,University of Szeged | And 5 more authors.
Molecules | Year: 2011

A straightforward and reliable method for the regioselective synthesis of steroidal 1,4-disubstituted triazoles and 1,5-disubstituted tetrazoles via copper(I)-catalyzed cycloadditions is reported. Heterocycle moieties were efficiently introduced onto the starting azide compound 3β-acetoxy- 16β-azidomethylandrost-5-en-17β-ol through use of the "click" chemistry approach. The antiproliferative activities of the newly-synthesized triazoles were determined in vitro on three human gynecological cell lines (HeLa, MCF7 and A2780) using the microculture tetrazolium assay. © 2011 by the authors; licensee MDPI, Basel, Switzerland.


Bartok T.,University of Szeged | Bartok T.,Fumizol Ltd | Tolgyesi L.,Eotvos University Joint Research and Training on Separation Techniques | Tolgyesi L.,Kromat Ltd | And 4 more authors.
Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment | Year: 2010

The aim of this study was to apply RP-HPLC/ESI-ITMS and RP-HPLC/ESI-TOFMS to investigate and characterise six new higher molecular weight fumonisins (three pairs of isomers) extracted from a Fusarium verticillioides-infected solid rice culture. The ITMS and ITMS2 spectra clearly indicated the m/z values (960, 984 and 986) of the protonated molecules and the FB1 toxin-like structures of these compounds, respectively. Moreover, the data evaluation software of the TOFMS equipment unambiguously demonstrated the exact masses of the protonated molecules and the suggested empirical formulae (C50H89NO16, C52H89NO16 and C52H91NO16) of the new fumonisins, with mass accuracy in the range between 0.1 and -1.1 ppm. Subtraction of the empirical formula of FB1 toxin (C34H59NO15) from these formulae and correction for the mass of water split-off from the fumonisin molecule during ester formation resulted in the empirical formulae of the fumonisin backbone esterifying agents (fatty acids): C16H32O2 (palmitic acid, PA), C18H32O2 (linoleic acid, LA) and C18H32O2 (oleic acid, OA). We denoted the new compounds as esterified FB1 (EFB1) toxins, with the suggested names EFB1 PA, iso-EFB1 PA, EFB1 LA, iso-EFB1 LA, EFB1 OA and iso-EFB1 OA. The total amount of these new compounds comprised 0.1% of the FB1 concentration, which may be rated as significant when it is considered that these new components are significantly more apolar than earlier-described fumonisins, and their uptake into and toxicity elicited in the various tissues of living organisms may therefore also be significantly different from those of other fumonisins. © 2010 Taylor & Francis.


Frank E.,University of Szeged | Kovacs D.,University of Szeged | Schneider G.,University of Szeged | Wolfling J.,University of Szeged | And 3 more authors.
Molecular Diversity | Year: 2014

Efficient synthesis of novel 16-spiroisoxazolines in the androst-5-ene series was carried out by 1,3-dipolar cycloadditions of different aryl nitrile oxides to 3β-acetoxy-16-methylene-androst-5-en-17-one. During the intermolecular ring closures, the attack of the O terminus of the nitrile oxide dipole from the α side on C-16 predominated for steric reasons permitting the reactions to occur in a regio- and stereoselective manner. The minor isomers in which the angular methyl group on C-13 and the O atom of the isoxazoline heteroring were in the β, β-cis orientation were obtained in a yield of only ∼10 %. Moreover, the conversions were influenced to a certain extent by the substituents on the aromatic moiety of the 1,3-dipoles. The stereostructures of the related diastereomers were confirmed by 2D NMR methods. Deacetylation of the primarily formed main products resulted in the corresponding 3β-OH analogs, which were further reduced to furnish 3β, 17β-diols. All of the synthetized compounds were subjected to in vitro pharmacological studies in order to investigate their antiproliferative effects on three malignant human adherent cell lines (HeLa, MCF7, and A431). © 2014 Springer International Publishing.


Molnar O.,Hungarian Academy of Sciences | Bartok T.,Fumizol Ltd. | Szecsi A.,Hungarian Academy of Sciences
Acta Microbiologica et Immunologica Hungarica | Year: 2015

Fusarium strains were isolated from rotten banana fruit imported into Hungary from some African and some Neotropical countries. The strains were identified using morphological features, 2-benzoxazolinone tolerance, translation elongation factor (EF-1α) sequences and inter simple sequence repeat (ISSR) analysis. All strains from Africa proved to be F. Verticillioides whereas the strains from the Neotropics are Fusarium musae. According to the PCR proof and the fumonisin toxin measurement F. musae strains cannot produce any fumonisins (FB1-4). © 2015 Akadémiai Kiadó, Budapest.


PubMed | Cereal Research Non profit Ltd., Hungarian Academy of Sciences, University of Szeged, Fumizol Ltd. and Edison House Holding Co.
Type: Journal Article | Journal: Journal of chromatographic science | Year: 2014

Fumonisins are a class of mycotoxins produced mainly by Fusarium species, which is primary fungal contaminant of the maize and maize-derived products around the world. The B-series fumonisins (FB1, FB2 and FB3) are the most abundant and toxic constituent; thus, their levels are regulated generally worldwide. In this study, we developed a reliable method for the measurement of fumonisin FB1, FB2 and FB3 mycotoxins from maize samples without the time-consuming derivatization step using a high-performance liquid chromatograph coupled with corona charged aerosol detector. The detection and quantitation limit of the whole method were 0.02 and 0.04 mg/kg for each fumonisins, respectively. The detection linearity was tested in the calibration range of 2 orders of magnitude and the recoveries from the spiked samples were determined. The developed method proved to be sufficient to measure the maximum residue levels of fumonisins, which are specified in European Union and United States in maize and maize-based products.


PubMed | Hungarian Academy of Sciences, Eötvös Loránd University, Cereal Research Non Profit Ltd., Fumizol Ltd. and University of Szeged
Type: Journal Article | Journal: Journal of chromatographic science | Year: 2014

Five previously unknown fumonisin mycotoxins (iso-FP1, iso-FP(2,3a), iso-FP(2,3b), FP4 and iso-FP4) and three previously described FP analogues (FP(1-3)) were detected in a solid rice culture inoculated with Fusarium verticillioides. The fumonisins were characterized by high-performance liquid chromatography-electrospray ionization time-of-flight mass spectrometry (HPLC-ESI-TOFMS) and ion trap mass spectrometry (ITMS). The FP isomers were separated by using a flat gradient on a special, high-coverage C18, narrow-bore HPLC column (YMC-Pack Jsphere ODS H80), which was suggested for the separation of structural isomers. The verified structures of the FP(1-3) mycotoxins, the relative retention times (by HPLC-ESI-TOFMS and ITMS), the exact masses of the molecular ions (by TOFMS) and the masses of the product ions, including the hydrocarbon backbones (by ITMS) of the new compounds, strongly suggested their structures.

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