The Chemistry of Mycotoxins

Bräse, Stefan; Gläser, Franziska; Kramer, Carsten S.; Lindner, Stephanie; Linsenmeier, Anna M.; Masters, Kye-Simeon; Meister, Anne C.; Ruff, Bettina M.; Zhong, Sabilla

doi:10.1007/978-3-7091-1312-7

Cited by 37 publications

(16 citation statements)

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“…In agreement with the literature, [5] cytotoxicity data of the structurally related RALs ( 11 – 13 ) indicated the importance of the ( Z )-enone for activity, as in hypothemycin ( 12 ) (IC 50 value of 0.58 μM, MDA-MB-435). Alternatively, aigialomycin A ( 11 ), with an ( E )-enone, and dihydrohypothemycin ( 13 ), with a reduced enone, were both inactive (IC 50 value >10 μM).…”

Section: Resultssupporting

confidence: 88%

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

et al. 2014

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Sixteen polyketides belonging to diverse structural classes, including monomeric/dimeric tetrahydroxanthones and resorcylic acid lactones, were isolated from an organic extract of a fungal culture Setophoma terrestris (MSX45109) using bioactivity-directed fractionation as part of a search for anticancer leads from filamentous fungi. Of these, six were new: penicillixanthone B (5), blennolide H (6), 11-deoxy blennolide D (7), blennolide I (9), blennolide J (10), and pyrenomycin (16). The known compounds were: secalonic acid A (1), secalonic acid E (2), secalonic acid G (3), penicillixanthone A (4), paecilin B (8), aigialomycin A (11), hypothemycin (12), dihydrohypothemycin (13), pyrenochaetic acid C (14), and nidulalin B (15). The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configurations of compounds 1–10 were determined using ECD spectroscopy combined with time-dependent density functional theory (TDDFT) calculations, while a modified Mosher’s ester method was used for compound 16. The cytotoxic activities of compounds (1–15) were evaluated using the MDA-MB-435 (melanoma) and SW-620 (colon) cancer cell lines. Compounds 1, 4, and 12 were the most potent with IC50 values ranging from 0.16 to 2.14 μM. When tested against a panel of bacteria and fungi, compounds 3 and 5 showed promising activity against the Gram-positive bacterium Micrococcus luteus with MIC values of 5 and 15 μg/mL, respectively.

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Section: Resultssupporting

confidence: 88%

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

et al. 2014

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“…It is one of the most distributed mycotoxins in the world, which makes ZEA study of great interest [77]. Chronic exposure to ZEA can produce reproductive disorders, estrogenism, abortions and sterility [77,78], as well as hepatotoxic, immunotoxic and hematotoxic effects [79]. Thus, the Food and Agriculture Organization of the United Nations (FAO) provides worldwide regulatory methods [80].…”

Section: Zearalenonementioning

confidence: 99%

Electrochemical Biosensors for the Determination of Toxic Substances Related to Food Safety Developed in South America: Mycotoxins and Herbicides

et al. 2017

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The goal of achieving food safety and quality has become increasingly important in relevant areas. The achievement of this objective includes a significant effort in different areas related to the production of raw materials, storage, transportation, etc. One of the central areas in the verification of food safety and food quality control is related to the analysis of food components and, in particular, possible toxic substances that they may contain. Therefore, the demand for appropriate methods for the determination of these substances is increasingly demanding. Thus, not only is accuracy and precision sought in the results of the analysis, but also the speed, simplicity and lowering of costs. In this way, electrochemical techniques and, particularly, electrochemical biosensors have emerged in recent times as good candidates to satisfy such requirements. This review summarizes the advances made in research and development centers located in South American countries related to the development of electrochemical biosensors for the determination of toxic substances present in foods, particularly mycotoxins and herbicides.

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“…Depending on molecular size and the presence and absence of polar functional groups LMWMs are either volatile or non-volatile. There exist numerous review articles and books on LMWMs that focus on one or more of the above mentioned aspects, the cited ones just representing a subjective selection (Betina, 1989;Gräfe, 1992;Seigler, 1998;Reese et al, 2000;Dixon, 2001;Hadacek, 2002;Crozier, 2006;Hedden and Thomas, 2006;Hartmann, 2007;Bednarek and Osbourn, 2009;Buchanan et al, 2009;Greenstein and Wood, 2011;Bräse et al, 2013).…”

Section: Lmwms In Living Organisms Definition Biosynthesis and Orgamentioning

confidence: 99%

Low-molecular-weight metabolite systems chemistry

Hadaček

Bachmann

2015

Front. Environ. Sci.

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Low-molecular-weight metabolites (LMWMs) comprise primary or central and a plethora of intermediary or secondary metabolites, all of which are characterized by a molecular weight below 900 Dalton. The latter are especially prominent in sessile higher organisms, such as plants, corals, sponges and fungi, but are produced by all types of microbial organisms too. Common to all of these carbon molecules are oxygen, nitrogen and, to a lesser extent, sulfur, as heteroatoms. The latter can contribute as electron donators or acceptors to cellular redox chemistry and define the potential of the molecule to enter charge-transfer complexes. Furthermore, they allow LMWMs to serve as organic ligands in coordination complexes with various inorganic metals as central atoms. Especially the transition metals Fe, Cu, and Mn can catalyze one electron reduction of molecular oxygen, which results in formation of free radical species and reactive follow-up reaction products. As antioxidants LMWMs can scavenge free radicals. Depending on the chemical environment, the same LMWMs can act as pro-oxidants by reducing molecular oxygen. The cellular regulation of redox homeostasis, a balance between oxidation and reduction, is still far from being understood. Charge-transfer and coordination complex formation with metals shapes LMWMs into gel-like matrices in the cytosol. The quasi-polymer structure is lost usually during the isolation procedure. In the gel state, LMWMs possess semiconductor properties. Also proteins and membranes are semiconductors. Together they can represent biotransistor components that can be part of a chemoelectrical signaling system that coordinates systems chemistry by initiating cell differentiation or tissue homeostasis, the activated and the resting cell state, when it is required. This concept is not new and dates back to Albert Szent-Györgyi.

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The Chemistry of Mycotoxins

Cited by 37 publications

References 0 publications

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

Biosynthetically Distinct Cytotoxic Polyketides from Setophoma terrestris

Electrochemical Biosensors for the Determination of Toxic Substances Related to Food Safety Developed in South America: Mycotoxins and Herbicides

Low-molecular-weight metabolite systems chemistry

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