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Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins

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A special issue of Toxins (ISSN 2072-6651). This special issue belongs to the section "Mycotoxins".

Deadline for manuscript submissions: closed (31 January 2020) | Viewed by 43277

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Dr. Michele Suman

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Barilla G. R. F.lli SpA, Advanced Laboratory Research, Via Mantova 166 - 43100 Parma, Italy

Special Issue Information

Dear Colleagues,

Mycotoxins are fungal metabolites commonly occurring in food, which pose a health risk to the consumer. In the last few years, worldwide authorities have frequently expressed opinions, setting limits, regulations and guidelines in order to reduce their levels in raw materials and food commodities. Modified forms of mycotoxins are often called “masked”. Masked mycotoxins, in ”senso strictu”, are conjugates of mycotoxins resulting from metabolic pathways activated by the interplay between pathogenic fungi and infected plants. Free mycotoxins can therefore frequently occur along with their conjugated forms.

Chemical and toxicological fate of mycotoxins is significantly related also to food processing, which implies high temperature, additives/improvers, long processing time, fermentation, etc. For example, this can then determine the release of parent compounds from/to conjugated forms as well as the ‘masking’ phenomenon associated with the mechanical energy and heat generated, which can prompt reactions with organic macromolecules. Thus, it is fundamental to develop proper analytical methods able to quantify all the different forms in both raw materials and finished food products; beside this it is crucial to assess human/animal exposure to modified forms of the various toxin forms in addition to the parent compounds, because many modified forms are hydrolyzed into the parent compounds or released from the matrix during digestion.

The present Toxins Special Issue will deal with all the different multi-faceted issues of this complex scenario.

Dr. Michele Suman
Guest Editor

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Keywords

mycotoxins
masked mycotoxins
modified mycotoxins
conjugated mycotoxins
chemical fate
toxicological fate
food processing
raw materials
food commodities
analytical methods

Published Papers (11 papers)

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Editorial

Jump to: Research, Review

3 pages, 181 KiB

Open AccessEditorial

Fate of Free and Modified Forms of Mycotoxins during Food Processing

by Michele Suman

Toxins 2020, 12(7), 448; https://doi.org/10.3390/toxins12070448 - 10 Jul 2020

Cited by 2 | Viewed by 1853

Abstract

International trade is highly affected by mycotoxin contaminations, which result in an annual 5% to 10% loss of global crop production [...] Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

Research

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8 pages, 567 KiB

Open AccessArticle

Conversion of Deoxynivalenol-3-Glucoside to Deoxynivalenol during Chinese Steamed Bread Processing

by Huijie Zhang, Li Wu, Weixi Li, Yan Zhang, Jingmei Li, Xuexu Hu, Lijuan Sun, Wenming Du and Bujun Wang

Toxins 2020, 12(4), 225; https://doi.org/10.3390/toxins12040225 - 03 Apr 2020

Cited by 8 | Viewed by 2126

Abstract

We reported the conversion of deoxynivalenol-3-glucoside (D3G) to deoxynivalenol (DON) during Chinese steamed bread (CSB) processing by artificial D3G contamination. Meanwhile, the effects of enzymes in wheat flour and those produced from yeast, along with the two main components in wheat flour—wheat starch and wheat gluten—on the conversion profiles of D3G were evaluated. The results showed D3G could convert to DON during CSB processing, and the conversion began with dough making and decreased slightly after fermentation and steaming. However, there was no significant difference in three stages. When yeast was not added, or enzyme-deactivated wheat flour was used to simulate CSB process, and whether yeast was added or not, D3G conversion could be observed, and the conversion was significantly higher after dough making. Likewise, D3G converted to DON when wheat starch and wheat gluten were processed to CSB, and the conversion in wheat starch was higher. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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15 pages, 325 KiB

Open AccessEditor’s ChoiceArticle

Selected Trichothecenes in Barley Malt and Beer from Poland and an Assessment of Dietary Risks Associated with their Consumption

by Edyta Ksieniewicz-Woźniak, Marcin Bryła, Agnieszka Waśkiewicz, Tomoya Yoshinari and Krystyna Szymczyk

Toxins 2019, 11(12), 715; https://doi.org/10.3390/toxins11120715 - 09 Dec 2019

Cited by 19 | Viewed by 3033

Abstract

Eighty-seven samples of malt from several Polish malting plants and 157 beer samples from the beer available on the Polish market (in 2018) were tested for Fusarium mycotoxins (deoxynivalenol (DON), nivalenol (NIV)), and their modified forms ((deoxynivalenol-3-glucoside (DON-3G), nivalenol-3-glucoside (NIV-3G), 3-acetyldeoxynivalenol (3-AcDON)). DON and its metabolite, DON-3G, were found the most, among the samples analyzed; DON and DON-3G were present in 90% and 91% of malt samples, and in 97% and 99% of beer samples, respectively. NIV was found in 24% of malt samples and in 64% of beer samples, and NIV-3G was found in 48% of malt samples and 39% of beer samples. In the malt samples, the mean concentration of DON was 52.9 µg/kg (range: 5.3–347.6 µg/kg) and that of DON-3G was 74.1 µg/kg (range: 4.4–410.3 µg/kg). In the beer samples, the mean concentration of DON was 12.3 µg/L (range: 1.2–156.5 µg/L) and that of DON-3G was 7.1 µg/L (range: 0.6–58.4 µg/L). The concentrations of other tested mycotoxins in the samples of malt and beer were several times lower. The risk of exposure to the tested mycotoxins, following the consumption of beer in Poland, was assessed. The corresponding probable daily intakes (PDIs) remained a small fraction of the tolerable daily intake (TDI). However, in the improbable worst-case scenario, in which every beer bottle consumed would be contaminated with mycotoxins present at the highest level observed among the analyzed beer samples, the PDI would exceed the TDI for DON and its metabolite after the consumption of a single bottle (0.5 L) of beer. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

12 pages, 1413 KiB

Open AccessFeature PaperArticle

Acrylamide Reduction Strategy in Combination with Deoxynivalenol Mitigation in Industrial Biscuits Production

by Michele Suman, Silvia Generotti, Martina Cirlini and Chiara Dall’Asta

Toxins 2019, 11(9), 499; https://doi.org/10.3390/toxins11090499 - 27 Aug 2019

Cited by 17 | Viewed by 3861

Abstract

Acrylamide is formed during baking in some frequently consumed food products. It is proven to be carcinogenic in rodents and a probable human carcinogen. Thus, the food industry is working to find solutions to minimize its formation during processing. To better understand the sources of its formation, the present study is aimed at investigating how acrylamide concentration may be influenced by bakery-making parameters within a parallel strategy of mycotoxin mitigation (focusing specifically on deoxynivalenol—DON) related to wholegrain and cocoa biscuit production. Among Fusarium toxins, DON is considered the most important contaminant in wheat and related bakery products, such as biscuits, due to its widespread occurrence. Exploiting the power of a Design of Experiments (DoE), several conditions were varied as mycotoxin contamination levels of the raw materials, recipe formulation, pH value of dough, and baking time/temperature; each selected treatment was varied within a defined range according to the technological requirements to obtain an appreciable product for consumers. Experiments were performed in a pilot-plant scale in order to simulate an industrial production and samples were extracted and analysed by HPLC-MS/MS system. Applying a baking temperature of 200 °C at the highest sugar dose, acrylamide increased its concentration, and in particular, levels ranged from 306 ± 16 µg/Kg d.m. and 400 ± 27 µg/Kg d.m. in biscuits made without and with the addition of cocoa, respectively. Conversely, using a baking temperature of 180 °C in the same conditions (pH, baking time, and sugar concentrations), acrylamide values remained below 125 ± 14 µg/Kg d.m. and 156 ± 15 µg/Kg d.m. in the two final products. The developed predictive model suggested how some parameters can concretely contribute to limit acrylamide formation in the final product, highlighting a significant role of pH value (correlated also to sodium bicarbonate raising agent), followed by baking time/temperature parameters. In particular, the increasing range of baking conditions influenced in a limited way the final acrylamide content within the parallel effective range of DON reduction. The study represents a concrete example of how the control and optimization of selected operative parameters may lead to multiple mitigation of specific natural/process contaminants in the final food products, though still remaining in the sensorial satisfactory range. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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16 pages, 526 KiB

Open AccessEditor’s ChoiceArticle

Determination of Deoxynivalenol Biomarkers in Italian Urine Samples

by Barbara De Santis, Francesca Debegnach, Brunella Miano, Giorgio Moretti, Elisa Sonego, Antonio Chiaretti, Danilo Buonsenso and Carlo Brera

Toxins 2019, 11(8), 441; https://doi.org/10.3390/toxins11080441 - 25 Jul 2019

Cited by 24 | Viewed by 3067

Abstract

Deoxynivalenol (DON) is a mycotoxin mainly produced by Fusarium graminearum that can contaminate cereals and cereal-based foodstuff. Urinary DON levels can be used as biomarker for exposure assessment purposes. This study assessed urinary DON concentrations in Italian volunteers recruited by age group, namely children, adolescents, adults, and the elderly. In addition, vulnerable groups, namely vegetarians and pregnant women, were included in the study. To determine the urinary DON, its glucuronide and de-epoxydated (DOM-1) forms, an indirect analytical approach was used, measuring free DON and total DON (as sum of free and glucuronides forms), before and after enzymatic treatment, respectively. Morning urine samples were collected on two consecutive days, from six different population groups, namely children, adolescent, adults, elderly, vegetarians and pregnant women. Total DON was measured in the 76% of the collected samples with the maximum incidences in children and adolescent age group. Urine samples from children and adolescent also showed the highest total DON levels, up to 17.0 ng/mg_creat. Pregnant women had the lowest positive samples per category (40% for day 1 and 43% for day 2, respectively), low mean levels of total DON (down to 2.84 ng/mg_creat) and median equal to 0 ng/mg_creat. Estimation of DON dietary intake reveals that 7.5% of the total population exceeds the TDI of 1 μg/kg bw/day set for DON, with children showing 40% of individuals surpassing this value (male, day 2). Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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13 pages, 1600 KiB

Open AccessEditor’s ChoiceArticle

Fluorescence Polarization Immunoassay for the Determination of T-2 and HT-2 Toxins and Their Glucosides in Wheat

by Vincenzo Lippolis, Anna C. R. Porricelli, Erminia Mancini, Biancamaria Ciasca, Veronica M. T. Lattanzio, Annalisa De Girolamo, Chris M. Maragos, Susan McCormick, Peiwu Li, Antonio F. Logrieco and Michelangelo Pascale

Toxins 2019, 11(7), 380; https://doi.org/10.3390/toxins11070380 - 01 Jul 2019

Cited by 22 | Viewed by 3684

Abstract

T-2 and HT-2 toxins and their main modified forms (T-2 glucoside and HT-2 glucoside) may co-occur in cereals and cereal-based products. A fluorescence polarization immunoassay (FPIA) was developed for the simultaneous determination of T-2 toxin, HT-2 toxin and relevant glucosides, expressed as sum. The developed FPIA, using a HT-2-specific antibody, showed high sensitivity (IC₅₀ = 2.0 ng/mL) and high cross-reactivity (100% for T-2 toxin and 80% for T-2 and HT-2 glucosides). The FPIA has been used to develop two rapid and easy-to-use methods using two different extraction protocols, based on the use of organic (methanol/water, 90:10, v/v) and non-organic (water) solvents, for the determination of these toxins in wheat. The two proposed methods showed analytical performances in terms of sensitivity (LOD 10 µg/kg) recovery (92–97%) and precision (relative standard deviations ≤13%), fulfilling the criteria for acceptability of an analytical method for the quantitative determination of T-2 and HT-2 toxins established by the European Union. Furthermore, the methods were then validated in accordance with the harmonized guidelines for the validation of screening methods included in the Regulation (EU) No. 519/2014. The satisfactory analytical performances, in terms of intermediate precision (≤25%), cut-off level (80 and 96 µg/kg for the two methods) and rate of false positives (<0.1%) confirmed the applicability of the proposed methods as screening method for assessing the content of these toxins in wheat at the EU indicative levels reported for T-2 and HT-2 toxins. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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14 pages, 1399 KiB

Open AccessEditor’s ChoiceArticle

Emerging Fusarium Mycotoxins Fusaproliferin, Beauvericin, Enniatins, and Moniliformin in Serbian Maize

by Igor Jajić, Tatjana Dudaš, Saša Krstović, Rudolf Krska, Michael Sulyok, Ferenc Bagi, Zagorka Savić, Darko Guljaš and Aleksandra Stankov

Toxins 2019, 11(6), 357; https://doi.org/10.3390/toxins11060357 - 19 Jun 2019

Cited by 50 | Viewed by 5651

Abstract

Emerging mycotoxins such as moniliformin (MON), enniatins (ENs), beauvericin (BEA), and fusaproliferin (FUS) may contaminate maize and negatively influence the yield and quality of grain. The aim of this study was to determine the content of emerging Fusarium mycotoxins in Serbian maize from the 2016, 2017, and 2018 harvests. A total of 190 samples from commercial maize production operations in Serbia were analyzed for the presence of MON, ENs, BEA, and FUS using liquid chromatography-tandem mass spectrometry (LC-MS/MS). The obtained results were interpreted together with weather data from each year. MON, BEA, and FUS were major contaminants, while other emerging mycotoxins were not detected or were found in fewer samples (<20%). Overall contamination was highest in 2016 when MON and BEA were found in 50–80% of samples. In 2017 and 2018, high levels of MON, FUS, and BEA were detected in regions with high precipitation and warm weather during the silking phase of maize (July and the beginning of August), when the plants are most susceptible to Fusarium infections. Since environmental conditions in Serbia are favorable for the occurrence of mycotoxigenic fungi, monitoring Fusarium toxins is essential for the production of safe food and feed. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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10 pages, 933 KiB

Open AccessEditor’s ChoiceArticle

Occurrence of the Ochratoxin A Degradation Product 2′R-Ochratoxin A in Coffee and Other Food: An Update

by Franziska Sueck, Vanessa Hemp, Jonas Specht, Olga Torres, Benedikt Cramer and Hans-Ulrich Humpf

Toxins 2019, 11(6), 329; https://doi.org/10.3390/toxins11060329 - 08 Jun 2019

Cited by 26 | Viewed by 4319

Abstract

Food raw materials can contain the mycotoxin ochratoxin A (OTA). Thermal processing of these materials may result in decreased OTA levels but also in the formation of the thermal isomerization product 2′R-ochratoxin A (2′R-OTA). So far, only 2′R-OTA levels reported from 15 coffee samples in 2008 are known, which is little when compared to the importance of coffee as a food and trading good. Herein, we present results from a set of model experiments studying the effect of temperatures between 120 °C and 270 °C on the isomerization of OTA to 2′R-OTA. It is shown that isomerization of OTA starts at temperatures as low as 120 °C. At 210 °C and above, the formation of 25% 2′R-OTA is observed in less than one minute. Furthermore, 51 coffee samples from France, Germany, and Guatemala were analyzed by HPLC-MS/MS for the presence of OTA and 2′R-OTA. OTA was quantified in 96% of the samples, while 2′R-OTA was quantifiable in 35% of the samples. The highest OTA and 2′R-OTA levels of 28.4 µg/kg and 3.9 µg/kg, respectively, were detected in coffee from Guatemala. The OTA:2′R-OTA ratio in the samples ranged between 2.5:1 and 10:1 and was on average 5.5:1. Besides coffee, 2′R-OTA was also for the first time detected in a bread sample and malt coffee powder. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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18 pages, 2861 KiB

Open AccessEditor’s ChoiceArticle

The Influence of Processing Parameters on the Mitigation of Deoxynivalenol during Industrial Baking

by David Stadler, Francesca Lambertini, Lydia Woelflingseder, Heidi Schwartz-Zimmermann, Doris Marko, Michele Suman, Franz Berthiller and Rudolf Krska

Toxins 2019, 11(6), 317; https://doi.org/10.3390/toxins11060317 - 04 Jun 2019

Cited by 24 | Viewed by 4316

Abstract

Deoxynivalenol (DON), a frequent contaminant of flour, can be partially degraded by baking. It is not clear: (i) How the choice of processing parameter (i.e., ingredients, leavening, and baking conditions) affects DON degradation and thus (ii) how much DON can be degraded during the large-scale industrial production of bakery products. Crackers, biscuits, and bread were produced from naturally contaminated flour using different processing conditions. DON degradation during baking was quantified with the most accurate analytical methodology available for this Fusarium toxin, which is based on liquid chromatography tandem mass spectrometry. Depending on the processing conditions, 0–21%, 4–16%, and 2–5% DON were degraded during the production of crackers, biscuits, and bread, respectively. A higher NaHCO₃ concentration, baking time, and baking temperature caused higher DON degradation. NH₄HCO₃, yeast, vinegar, and sucrose concentration as well as leavening time did not enhance DON degradation. In vitro cell viability assays confirmed that the major degradation product isoDON is considerably less toxic than DON. This proves for the first time that large-scale industrial baking results in partial detoxification of DON, which can be enhanced by process management. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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11 pages, 1096 KiB

Open AccessEditor’s ChoiceArticle

Fate of Ergot Alkaloids during Laboratory Scale Durum Processing and Pasta Production

by Sheryl A. Tittlemier, Dainna Drul, Mike Roscoe, Dave Turnock, Dale Taylor and Bin Xiao Fu

Toxins 2019, 11(4), 195; https://doi.org/10.3390/toxins11040195 - 31 Mar 2019

Cited by 19 | Viewed by 3641

Abstract

The fate of ergot alkaloids during the milling of durum and subsequent production and cooking of pasta was examined. Durum samples containing varying amounts of ergot sclerotia (0.01–0.1% by mass) were milled, and all milling product was analyzed for 10 ergot alkaloids using liquid chromatography with tandem mass spectrometry. Spaghetti was prepared from the semolina obtained during milling. Ergocristine, ergocristinine, and ergotamine were the predominant ergot alkaloids observed in the milling fractions and spaghetti. Approximately 84% of the total ergot alkaloid mass of the whole grain durum resided in the milling product fractions associated with the outer kernel layers (bran, shorts, feeds). No consistent loss of ergot alkaloids was observed during the production or cooking of spaghetti. However, changes in the ratio of R- to S-enantiomers occurred during the milling and cooking of spaghetti. Products containing bran, shorts, and feeds, as well as cooked spaghetti, contained a higher proportion of the less biologically active S-enantiomers. The results of this study emphasize the need to monitor R- and S-enantiomers, and to consider food and feed products, as opposed to whole grain, when assessing any exposure of consumers to ergot alkaloids. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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Review

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27 pages, 1034 KiB

Open AccessEditor’s ChoiceReview

Mycotoxins during the Processes of Nixtamalization and Tortilla Production

by Sara Schaarschmidt and Carsten Fauhl-Hassek

Toxins 2019, 11(4), 227; https://doi.org/10.3390/toxins11040227 - 16 Apr 2019

Cited by 38 | Viewed by 7072

Abstract

Tortillas are a traditional staple food in Mesoamerican cuisine, which have also become popular on a global level, e.g., for wraps or as snacks (tortilla chips). Traditional tortilla production includes alkaline cooking (nixtamalization) of maize kernels. This article summarizes the current knowledge on mycotoxin changes during the nixtamalization of maize and tortilla production. Upon nixtamalization, mycotoxins can be affected in different ways. On the one hand, the toxins can be physically removed during steeping and washing. On the other hand, mycotoxins might be degraded, modified, or released/bound in the matrix by high pH and/or high temperature. This also applies to the subsequent baking of tortillas. Many studies have shown reduced mycotoxin levels in alkali-cooked maize and in tortillas. Most of the available data relate to aflatoxins and fumonisins. The reduction (and detoxification) of aflatoxins during nixtamalization might, however, be partially reversed in acidic conditions. The loss of fumonisin concentrations is to some extent accompanied by hydrolyzation and by lower toxicity. However, some studies have indicated the potential formation of toxicologically relevant modified forms and matrix-associated fumonisins. More data are required to assess the influence of alkaline cooking regarding such modified forms, as well as mycotoxins other than aflatoxins/fumonisins. Full article

(This article belongs to the Special Issue Fate of Free, “Masked” and Conjugated/Modified forms of Mycotoxins)

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