Determination of Fusarium mycotoxins enniatins, beauvericin and fusaproliferin in cereals and derived products from Tunisia

Oueslati, Souheib; Meca, G.; Mliki, Ahmed; Ghorbel, Abdelwahed; Mañes, Jordi

doi:10.1016/j.foodcont.2011.02.015

Cited by 62 publications

(49 citation statements)

References 31 publications

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“…Breakfast cereals from Tunisian and Moroccan markets contained on average 57.4 and 10.6 mg/kg EnnB (Mahnine et al, 2011;Queslati et al, 2011). In egg yolks from laying hens fed with enniatin-contaminated feed, up to 3.8 g/kg enniatin B was detected (Jestoi et al, 2009), demonstrating the molecule's tendency to bioaccumulate in lipophilic media.…”

Section: Introductionmentioning

confidence: 98%

“…Grains in northern Europe were contaminated with high levels of enniatins in recent years, adding up to maximal concentrations of 7.7 and 24.8 mg/kg in Norwegian and Finnish wheat, respectively (Uhlig et al, 2007). In Mediterranean countries, wheat and sorghum containing up to 493 and 696 mg/kg enniatins, respectively, were observed (Mahnine et al, 2011;Queslati et al, 2011). Enniatin B (EnnB), the most prevalent among the 28 homologs identified (Firáková et al, 2007), is a cyclic hexadepsipeptide consisting of three d-2-hydroxyisovaleric acid residues linked alternatively to three N-methyl-L-valines (N-Me-Val), resulting in a 18-membered (N-Me-Val-d-2-hydroxyisovaleric acid) 3 molecule with the molecular formula and weight C 36 H 63 N 3 O 9 and 639.83 g/mol ( Fig.…”

Section: Introductionmentioning

confidence: 99%

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In Vitro Metabolism of the Mycotoxin Enniatin B in Different Species and Cytochrome P450 Enzyme Phenotyping by Chemical Inhibitors

Fæste

Ivanova²,

Uhlig³

2011

Drug Metab Dispos

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ABSTRACT:Enniatins are cyclic hexapeptidic mycotoxins produced by fungi growing on field grains, especially in wet climates. They show considerable resistance to food and feed processing technologies and might cause intoxication of humans and animals. Enniatins are also under exploration as anticancer drugs. The observed difference of in vitro and in vivo toxicities suggests low absorption or fast elimination of the enniatins after oral uptake. In the study presented here, in vitro metabolism studies of enniatin B were performed using rat, dog, and human liver microsomes under conditions of linear kinetics to estimate the respective elimination rates. Furthermore, cytochrome P450 reaction phenotyping with chemical inhibitors selective for human enzymes was carried out. Twelve metabolites were separated and characterized by multiple high-performance liquid chromatographic/mass spectrometric analyses as products of oxidation and demethylation reactions. Biotransformation rates and metabolite patterns varied considerably in the three species. The intrinsic clearances determined in assays with rat, dog, and human liver microsomes were 1.16, 8.23, and 1.13 l/(h ⅐ kg), respectively. The predicted enniatin B in vivo blood clearances were 1.57 l/(h ⅐ kg) in rats, 1.67 l/(h ⅐ kg) in dogs, and 0.63 l/(h ⅐ kg) in humans. CYP3A4 was important for enniatin B metabolism in human microsomes as shown by 80% inhibition and impaired metabolite formation in the presence of troleandomycin. CYP1A2 and CYP2C19 were additionally involved. Preliminary results showed that CYP3A and CYP1A might also be relevant in rats and dogs. The extensive hepatic metabolism could explain the reduced in vivo potential of enniatin B.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

In Vitro Metabolism of the Mycotoxin Enniatin B in Different Species and Cytochrome P450 Enzyme Phenotyping by Chemical Inhibitors

Fæste

Ivanova²,

Uhlig³

2011

Drug Metab Dispos

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“…Jedná se o cyklické hexadepsipeptidy skládající se ze střídajících se jednotek D--α-hydroxy-isovaleryl-(2-hydroxy-3-methylbutanové kyseliny) a aminokyselin (Oueslati et al, 2011), kde jednotlivými substituenty R 1 , R 2 a R 3 jsou v případě enniatnů buď sekundární butyl nebo isopropyl, u beauvericinu potom fenylmethyl (Santini et al, 2012) (obr.1). Moniliformin má strukturu hydroxycyklobutenedionu, tedy malé iontové molekuly ve formě sodné nebo draselné soli karboxylové kyseliny (Springer et al, 1974).…”

Section: ■ 2 Vlastnosti "Emerging" Mykotoxinůunclassified

“…These cyclic hexadepsipeptides consist of alternating D-α-hydroxy-isovaleryl-(2-hydroxy-3-methylbutan acid) and amino acid-units (Oueslati et al, 2011), in enniatins, the individual R 1 , R 2 and R 3 substituents are either secondary buthyl or isopropyl, in beauvericin, phenylmethyl (Santini et al, 2012) (Fig. 1).…”

Section: ■ 2 "Emerging" Mycotoxin Characteristicsmentioning

confidence: 99%

The occurrence of "emerging" mycotoxins in brewing raw materials.

Benešová¹,

Čumová²,

Běláková³

et al. 2015

Kvasny Prum

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“…Key words: cyclic pentadepsipeptides; Fusarium solani; environmental conditions; response surface methodology Various reviews of peptides from fungi have revealed that Fusarium strains found in fungi-infected plants produce several cyclic depsipeptides such as beauvericin, 1) enniatins, 2,3) zygosporamide, 4) and neosansalvamide analogs 5,6) via the non-ribosomal peptide synthesis system. 7,8) These cyclic depsipetides exhibit numerous pharmaceutical benefits such as cytotoxic, 9,10) antifungal, 11) and antibiotic 1) effects as well as calcium channel antagonism.…”

mentioning

confidence: 99%

Optimization of culture conditions of Fusarium solani for the production of neoN-methylsansalvamide

Lee

Phat

Nam

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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The aim of this study was to optimize the culture conditions of Fusarium solani KCCM90040 on cereal grain for the production of neoN-methylsansalvamide, a novel low-molecular-weight cyclic pentadepsipeptide exhibiting cytotoxic and multidrug resistance reversal effects. From the analysis of variance results using response surface methodology, temperature, initial moisture content, and growth time were shown to be important parameters for the production of neoN-methylsansalvamide on cereal grain. A model was established in the present study to describe the relationship between environmental conditions and the production of neoN-methylsansalvamide on rice, the selected cereal grain. The optimal culture conditions were determined at 25.79°C with the initial moisture content of 40.79%, and 16.19 days of growth time. This report will give important information concerning the optimization of environmental conditions using statistic methodology for the production of a new cyclic pentadepsipeptide from fungi.Key words: cyclic pentadepsipeptides; Fusarium solani; environmental conditions; response surface methodology Various reviews of peptides from fungi have revealed that Fusarium strains found in fungi-infected plants produce several cyclic depsipeptides such as beauvericin, 1) enniatins, 2,3) zygosporamide, 4) and neosansalvamide analogs 5,6) via the non-ribosomal peptide synthesis system. 7,8) These cyclic depsipetides exhibit numerous pharmaceutical benefits such as cytotoxic, 9,10) antifungal, 11) and antibiotic 1) effects as well as calcium channel antagonism.12) Another cytotoxic cyclic pentadepsipeptides, sansalvamide analogs, were produced by Fusarium strains. 13,14) Sansalvamide A was first reported from the marine micro-organism Halodule wrightii, 14)This N-methylated sansalvamide exhibited in vitro cytotoxicity in a National Cancer Institute human tumor cell line screen (EC 50 = 8.3 μmol).14) Sansalvamide showed cytototoxic potency against HCT116 (colon carcinoma), COLO205 (colon), and SK-MEL-2 (melanoma) cancer cell lines with EC 50 values of 9.8, 3.5, and 5.9 μg/mL, respectively. 13) Sansalvamide and its analogs, which were produced by organic synthesis, caused marked time-and concentration-dependent inhibition of DNA synthesis and cell proliferation of human pancreatic cancer cell lines. [15][16][17] Furthermore, sansalvamide and its analogs showed a strong cytotoxic effect against multidrug resistance (MDR) human colon cancer cell lines.18) These anticancer effects of sansalvamide analogs can be attributed to their inhibition of topoisomerase I, and their cytotoxicity may be mediated by this mechanism.17,19) Sansalvamide analogs exhibited cytotoxic activity against human cancer cell lines, suggesting that they could be valuable therapeutic agents. 17,18) Our research group isolated several Fusarium strains producing different cyclic depsipeptides including enniatins H, I, and MK1688 with beauvericin. 20) Interestingly, one isolate (Fusarium solani KCCM90040) produced a novel cyclic pentadepsipeptide, n...

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Determination of Fusarium mycotoxins enniatins, beauvericin and fusaproliferin in cereals and derived products from Tunisia

Cited by 62 publications

References 31 publications

In Vitro Metabolism of the Mycotoxin Enniatin B in Different Species and Cytochrome P450 Enzyme Phenotyping by Chemical Inhibitors

In Vitro Metabolism of the Mycotoxin Enniatin B in Different Species and Cytochrome P450 Enzyme Phenotyping by Chemical Inhibitors

The occurrence of "emerging" mycotoxins in brewing raw materials.

Optimization of culture conditions of Fusarium solani for the production of neoN-methylsansalvamide

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