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Mycotoxins

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 May 2019) | Viewed by 18567

Special Issue Editors

Department of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, Italy
Interests: characterization of masked mycotoxins; catabolic fate and toxicological relevance of parent and conjugate mycotoxins in humans; profiling of bioactive compounds in plant-derived food; mass spectrometry based methods for the profiling of bioactive compounds
Special Issues, Collections and Topics in MDPI journals
Department of Food and Drug, University of Parma, 43124 Parma, Italy
Interests: food chemistry and toxicology; xenobiotics of food origin; in silico/in vitro approaches; transformation and metabolic fate of food constituents and contaminants; enzyme-based strategies to mitigate food contaminants
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Mycotoxins are referred to as low-molecular-weight secondary metabolites produced by molds (ascomycetes mushrooms) that may have a wide spectrum of adverse effects on humans, animals, and plants. In particular, their almost unavoidable occurrence in food and feed is posing a severe threat to public health, and it is also a possible cause of trade friction on a global scale. Most of their effects are organ-specific, but some mycotoxins may have broader effects at a systemic level. The induction of cancer by some mycotoxins through initiation and promotion processing, in animals and possibly in humans, is one of the major concerns regarding their chronic effects, albeit their pleiotropic effects may be responsible for a wealth of disfunctions and altered physiological states at both chronic and acute levels. As an example, the modulation of immune systems as well as endocrine disrupting activity are among the effects of most concerns studied over the years.

Meanwhile, fungal secondary metabolites can also benefit humans in different ways. For instance, they can be used as antibiotics (penicillins) or immunosuppressants (cyclosporine).

In this Special Issue, original reaserch findings and review articles dealing with, but not limited to, the mechanisms and modes of action in both animals and plants, treatments to counteract adverse effects in living organisms, strategies to prevent and/or reduce accumulation in the food and feed production chains, innovative strategies of detection, as well as sound evidence pointing to possible beneficial effects of fungal metabolites are considered for publication.

Prof. Dr. Chiara Dall'Asta
Dr. Luca Dellafiora
Guest Editors

Manuscript Submission Information

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Keywords

  • Mycotoxins
  • Aflatoxins
  • Fumonisins
  • Satratoxins
  • Ochratoxin
  • Fungal ecology
  • Mycotoxin occurrence
  • Mycotoxin analysis
  • Mycotoxin mitigation
  • Food/feed security
  • Food safety
  • Mycotoxins toxicology

Published Papers (5 papers)

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Research

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15 pages, 2315 KiB  
Article
Sabotage at the Powerhouse? Unraveling the Molecular Target of 2-Isopropylbenzaldehyde Thiosemicarbazone, a Specific Inhibitor of Aflatoxin Biosynthesis and Sclerotia Development in Aspergillus flavus, Using Yeast as a Model System
by Cristina Dallabona, Marianna Pioli, Giorgio Spadola, Nicolò Orsoni, Franco Bisceglie, Tiziana Lodi, Giorgio Pelosi, Francesco Maria Restivo and Francesca Degola
Molecules 2019, 24(16), 2971; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24162971 - 16 Aug 2019
Cited by 4 | Viewed by 2949
Abstract
Amongst the various approaches to contain aflatoxin contamination of feed and food commodities, the use of inhibitors of fungal growth and/or toxin biosynthesis is showing great promise for the implementation or the replacement of conventional pesticide-based strategies. Several inhibition mechanisms were found taking [...] Read more.
Amongst the various approaches to contain aflatoxin contamination of feed and food commodities, the use of inhibitors of fungal growth and/or toxin biosynthesis is showing great promise for the implementation or the replacement of conventional pesticide-based strategies. Several inhibition mechanisms were found taking place at different levels in the biology of the aflatoxin-producing fungal species such as Aspergillus flavus: compounds that influence aflatoxin production may block the biosynthetic pathway through the direct control of genes belonging to the aflatoxin gene cluster, or interfere with one or more of the several steps involved in the aflatoxin metabolism upstream. Recent findings pointed to mitochondrial functionality as one of the potential targets of some aflatoxin inhibitors. Additionally, we have recently reported that the effect of a compound belonging to the class of thiosemicarbazones might be related to the energy generation/carbon flow and redox homeostasis control by the fungal cell. Here, we report our investigation about a putative molecular target of the 3-isopropylbenzaldehyde thiosemicarbazone (mHtcum), using the yeast Saccharomyces cerevisiae as model system, to demonstrate how the compound can actually interfere with the mitochondrial respiratory chain. Full article
(This article belongs to the Special Issue Mycotoxins)
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10 pages, 1686 KiB  
Article
Role of Some Food-Grade Synthesized Flavonoids on the Control of Ochratoxin A in Aspergillus carbonarius
by Alessandra Ricelli, Martina De Angelis, Ludovica Primitivo, Giuliana Righi, Carla Sappino and Roberto Antonioletti
Molecules 2019, 24(14), 2553; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24142553 - 13 Jul 2019
Cited by 10 | Viewed by 2335
Abstract
Ochratoxin A (OTA) is a mycotoxin with a serious impact on human health. In Mediterranean countries, the black Aspergilli group, in particular Aspergillus carbonarius, causes the highest OTA contamination. Here we describe the synthesis of three polyphenolic flavonoids: 5-hydroxy-6,7-dimethoxy-flavone (MOS), 5,6-dihydroxy-7-methoxy-flavone (NEG), [...] Read more.
Ochratoxin A (OTA) is a mycotoxin with a serious impact on human health. In Mediterranean countries, the black Aspergilli group, in particular Aspergillus carbonarius, causes the highest OTA contamination. Here we describe the synthesis of three polyphenolic flavonoids: 5-hydroxy-6,7-dimethoxy-flavone (MOS), 5,6-dihydroxy-7-methoxy-flavone (NEG), and 5,6 dihydroxy-flavone (DHF), as well as their effect on the prevention of OTA biosynthesis and lipoxygenase (LOX) activity in A. carbonarius cultured in a conducive liquid medium. The best control effect on OTA biosynthesis was achieved using NEG and DHF. In fungal cultures treated with these compounds at 5, 25, and 50 μg/mL, OTA biosynthesis significantly decreased throughout the 8-day experiment. NEG and DHF appear to have an inhibiting effect also on the activity of LOX, whereas MOS, which did not significantly inhibit OTA production, had no effect on LOX activity. The presence of free hydroxyls in catecholic position in the molecule appears to be a determining factor for significantly inhibiting OTA biosynthesis. However, the presence of a methoxy group in C-7 in NEG could slightly lower the molecule’s reactivity increasing OTA inhibition by this molecule at 5 μg/mL. Polyphenolic flavonoids present in edible plants may be easily synthesized and used to control OTA biosynthesis. Full article
(This article belongs to the Special Issue Mycotoxins)
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12 pages, 2308 KiB  
Article
Interaction of Dihydrocitrinone with Native and Chemically Modified Cyclodextrins
by Zelma Faisal, Sándor Kunsági-Máté, Beáta Lemli, Lajos Szente, Dominik Bergmann, Hans-Ulrich Humpf and Miklós Poór
Molecules 2019, 24(7), 1328; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24071328 - 04 Apr 2019
Cited by 11 | Viewed by 2983
Abstract
Citrinin (CIT) is a nephrotoxic mycotoxin produced by Aspergillus, Penicillium, and Monascus genera. It appears as a contaminant in grains, fruits, and spices. After oral exposure to CIT, its major urinary metabolite, dihydrocitrinone (DHC) is formed, which can be detected in [...] Read more.
Citrinin (CIT) is a nephrotoxic mycotoxin produced by Aspergillus, Penicillium, and Monascus genera. It appears as a contaminant in grains, fruits, and spices. After oral exposure to CIT, its major urinary metabolite, dihydrocitrinone (DHC) is formed, which can be detected in human urine and blood samples. Cyclodextrins (CDs) are ring-shaped molecules built up from glucose units. CDs can form host-guest type complexes with several compounds, including mycotoxins. In this study, the complex formation of DHC with native and chemically modified beta- and gamma-cyclodextrins was tested at a wide pH range, employing steady-state fluorescence spectroscopic and modeling studies. The weakly acidic environment favors the formation of DHC-CD complexes. Among the CDs tested, the quaternary-ammonium-γ-cyclodextrin (QAGCD) formed the most stable complexes with DHC. However, the quaternary-ammonium-β-cyclodextrin (QABCD) induced the strongest enhancement in the fluorescence signal of DHC. Our results show that some of the chemically modified CDs are able to form stable complexes with DHC (logK = 3.2–3.4) and the complex formation can produce even a 20-fold increase in the fluorescence signal of DHC. Considering the above-listed observations, CD technology may be a promising tool to increase the sensitivity of the fluorescence detection of DHC. Full article
(This article belongs to the Special Issue Mycotoxins)
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11 pages, 1411 KiB  
Article
Development of a Bioactive Sauce Based on Oriental Mustard Flour with Antifungal Properties for Pita Bread Shelf Life Improvement
by Raquel Torrijos, Tiago M. Nazareth, Júlia Pérez, Jordi Mañes and Giuseppe Meca
Molecules 2019, 24(6), 1019; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24061019 - 14 Mar 2019
Cited by 17 | Viewed by 2837
Abstract
Ochratoxin A (OTA) is a mycotoxin produced in the secondary metabolism of fungus belonging to the genus Aspergillus and Penicillium. In this study, the employment of oriental mustard flour (OMF) as an ingredient in a packaged sauce was evaluated for the generation [...] Read more.
Ochratoxin A (OTA) is a mycotoxin produced in the secondary metabolism of fungus belonging to the genus Aspergillus and Penicillium. In this study, the employment of oriental mustard flour (OMF) as an ingredient in a packaged sauce was evaluated for the generation in situ of the antimicrobial compound allyl isothiocyanate (AITC) in order to preserve pita bread contaminated with Penicillium verrucosum VTT D-01847, an OTA producer, in an active packaging system. Four different concentrations (8, 16, 33 and 50 mg/g) were tested. Mycelium formation, mycotoxin production, AITC absorbed by the food matrix, and volatilization kinetics were studied for each concentration. The results obtained were compared with bread treated with the commercial additive calcium propionate (E-282). The results showed a shelf life increase of two and three days with the employment of 33 and 50 mg/g of OMF, with a significant reduction of the fungal population (3.1 and 5.7 logs, respectively) in comparison with the control experiment. The use of 16 and 33 mg/g of OMF in the sauce formulation decreased the concentration of OTA in the bread samples while no OTA production was detected employing 50 mg/g of OMF. Full article
(This article belongs to the Special Issue Mycotoxins)
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Review

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39 pages, 8636 KiB  
Review
Enzymes for Detoxification of Various Mycotoxins: Origins and Mechanisms of Catalytic Action
by Ilya Lyagin and Elena Efremenko
Molecules 2019, 24(13), 2362; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24132362 - 26 Jun 2019
Cited by 78 | Viewed by 6864
Abstract
Mycotoxins are highly dangerous natural compounds produced by various fungi. Enzymatic transformation seems to be the most promising method for detoxification of mycotoxins. This review summarizes current information on enzymes of different classes to convert various mycotoxins. An in-depth analysis of 11 key [...] Read more.
Mycotoxins are highly dangerous natural compounds produced by various fungi. Enzymatic transformation seems to be the most promising method for detoxification of mycotoxins. This review summarizes current information on enzymes of different classes to convert various mycotoxins. An in-depth analysis of 11 key enzyme mechanisms towards dozens of major mycotoxins was realized. Additionally, molecular docking of mycotoxins to enzymes’ active centers was carried out to clarify some of these catalytic mechanisms. Analyzing protein homologues from various organisms (plants, animals, fungi, and bacteria), the prevalence and availability of natural sources of active biocatalysts with a high practical potential is discussed. The importance of multifunctional enzyme combinations for detoxification of mycotoxins is posed. Full article
(This article belongs to the Special Issue Mycotoxins)
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