fusaproliferin and beauvericin

Mycotoxins are secondary metabolites produced by several species of fungi, including the

Topics: Animal Feed; Animals; Depsipeptides; Edible Grain; Food Contamination; Livestock; Mycotoxins; Terpenes

In recent years consumers and the scientific community have become increasingly interested in food safety, making it a major focus among the objectives of the international institutions responsible for food safety monitoring, e.g. the European Union or the EFSA. Aspects attracting much attention are the colonization of food by microscopic fungi which, under aerobic conditions, produce toxic secondary metabolites known as mycotoxins, and the accumulation of these toxins in the food chain. Numerous studies of surveillance, detoxification, prevention, and toxicological aspects reported in the literature mostly concentrate on major mycotoxins such as aflatoxins, ochratoxin A, trichothecenes, and fumonisins; studies on toxic secondary metabolites of mycotoxins are less common or are only just beginning. Among the molecules of interest, the family of beauvericin and fusaproliferin is certainly the most interesting. The objective of this review is to summarize reported data and the methods used to extract and quantify beauvericin and fusaproliferin in food matrices.

Topics: Animals; Chemistry Techniques, Analytical; Depsipeptides; Food Contamination; Humans; Terpenes

The contamination of foods and feed with mycotoxins is a commonly known problem. Intense investigations have been conducted to study the occurrence, toxicity, and recently also the prevention and detoxification strategies of mycotoxins in human and animal food chains. Most of the studies have emphasized on "traditional" mycotoxins, such as aflatoxins, ochratoxin A, and trichothecenes. However, one of the most common grain-contaminating genus of fungi, Fusarium spp., is also capable of producing other toxic secondary metabolites - the so-called emerging mycotoxins such as fusaproliferin, beauvericin, enniatins, and moniliformin. So far, only limited data is available on these metabolites. This is not only due to their late recognition but especially the late understanding of their role as mycotoxins. This paper summarizes the existing data on the chemistry, analytical techniques, biosynthesis, production, toxicity, and occurrence data on fusaproliferin, beauvericin, enniatins, and moniliformin. Based on the available studies, attention should be paid to the studies on the distinct significance of these compounds in the human and animal food chains.

Topics: Cyclobutanes; Depsipeptides; Edible Grain; Food Contamination; Fusarium; Mycotoxins; Terpenes

Maize ear rot is a common disease found worldwide, caused by several toxigenic Fusarium species. Maize ears and kernels infected by Fusarium subglutinans contained significant amounts of beauvericin, fusaproliferin, moniliformin, and enniatins. In 2011, F. subglutinans sensu lato has been divided into two species: Fusarium temperatum sp. nov. and F. subglutinans sensu stricto, showing different phylogeny and beauvericin production within the populations of maize pathogens in Belgium. Isolates of the new species-F. temperatum-were also identified and characterized in Spain, Argentina, Poland, France, and China as one of the most important pathogens of maize. Moreover, F. temperatum was proved to be pathogenic to maize seedlings and stalks. We identified Fusarium isolates obtained from diseased maize ears collected between 2013 and 2016 in Poland (321 isolates). Based on morphological analyses, six Fusarium species were identified. Molecular identification performed on the set of selected isolates (42 isolates) revealed 34 isolates to be F. temperatum and only five to be F. subglutinans. Interestingly, the phylogenetic analysis showed that the population of F. temperatum infecting maize in Poland remained quite uniform for over 30 years with only a few exceptions. For the first time, a single isolate of Fusarium ramigenum was detected from the area of Poland. Significant amounts of BEA were found in Fusarium-damaged kernels. The same kernel samples contained also enniatins A1, A, B1, and B. The results clearly demonstrate the occurrence of F. temperatum as maize pathogen in Poland for over the last three decades.

Topics: Cyclobutanes; Depsipeptides; Fusarium; Mycotoxins; Phylogeny; Plant Diseases; Poland; Terpenes; Zea mays

The effect of water activity (aw = 0.95, 0.98 and 0.995), temperature (15, 25 and 30°C), incubation time (7, 14, 21 and 28 days), and their interactions on growth and moniliformin (MON), beauvericin (BEA), fusaproliferin (FUS) and fumonisin B1 (FB1) production by two strains of Fusarium temperatum isolated from Argentinean maize were determined in vitro on sterile layers of maize grains. The results showed that there was a wide range of conditions for growth and mycotoxins production by F. temperatum. Both strains were found to grow faster with increasing aw and at 30°C. In relation to mycotoxin production, the two strains produced more FUS than the other mycotoxins regardless of aw or temperature evaluated (maximum = 50,000 μg g(-1)). For FUS, MON and BEA, the maximum levels were observed at 0.98 aw and 30°C (50,000, 5000 and 2000 μg g(-1) respectively). The lowest levels for these three mycotoxins were detected at 15°C and 0.95 aw (1700 and 100 μg g(-1) for FUS and MON respectively), and at 0.98 aw (400 μg g(-1) for BEA). The maximum levels of FB1 were produced at 15°C and 0.98 aw (1000 μg g(-1)). At all aw and temperatures combinations evaluated there was an increase in toxin concentrations with time incubation. The maximum levels were detected at 21 days. Statistical analyses of aw, temperature, incubation time, and the two- and three-way interactions between them showed significant effects on mycotoxins production by F. temperatum. For its versatility on growth and mycotoxin production, F. temperatum represents a toxicological risk for maize in the field and also during grain storage.

Topics: Argentina; Cyclobutanes; Depsipeptides; Food Microbiology; Fumonisins; Fusarium; Temperature; Terpenes; Time Factors; Water; Zea mays

One of the main sources of emerging Fusarium mycotoxins in human nutrition is the cereals and cereal products. In this study, an analytical method to determine enniatins A, A1, B and B1 (ENs), beauvericin (BEA) and fusaproliferin (FUS) based on Ultra-Turrax extraction followed by liquid chromatography coupled to triple quadrupole mass spectrometer detector (MS/MS QqQ), was applied for the analysis of pasta. For this purpose, 114 commercial samples of pasta were acquired from supermarkets located in Valencia. The results showed higher frequencies of contamination in organic pasta than in conventional pasta, while the concentration levels were variable for both types of pasta. In positive samples, BEA levels varied from 0.10 to 20.96μg/kg and FUS levels varied from 0.05 to 8.02μg/kg. ENs levels ranged from 0.25 to 979.56μg/kg, though the majority of the values were below 25μg/kg. Besides, it was observed the simultaneous presence of two or more mycotoxins in a high percentage of the samples. Finally, an evaluation of the dietary exposure of the emerging Fusarium mycotoxins was performed in the Spanish population. The prevalence of ENs, BEA and FUS in cereal products suggests that the toxins may pose a health risk to Spanish population.

Topics: Chromatography, Liquid; Depsipeptides; Edible Grain; Food Contamination; Fusarium; Humans; Mycotoxins; Organic Agriculture; Public Health; Reproducibility of Results; Spain; Tandem Mass Spectrometry; Terpenes

Beauvericin (BEA) is a cyclohexadepsipeptide mycotoxin which has insecticidal properties and produces cytotoxic effects in mammalian cells. Fusaproliferin (FUS) is a mycotoxin that has toxic activity against brine shrimp, insect cells, and teratogenic effects on chicken embryos. The aim of this study was to determine the cytotoxicity of BEA and FUS in human epithelial colorectal adenocarcinoma HT-29 and Caco-2 cells, the transepithelial transport and the bioavailability using Caco-2 cells as a simulated in vitro gastrointestinal model of the human intestinal epithelium. The inhibitory concentration (IC(50)) evidenced by BEA in the Caco-2 cells was 24.6 and 12.7 μM at 24 and 48 h exposure, respectively, whereas the IC(50) values evidenced in HT-29 cells were 15.0 and 9.7 μM, respectively. FUS was cytotoxic, but no IC(50) data were observed in the range of concentration tested. BEA bioavailability was variable from 50.1% to 54.3%, whereas FUS presented a bioavailability variable from 80.2% to 83.2%. Results obtained demonstrated a potential risk for human health.

Topics: Biological Availability; Caco-2 Cells; Cell Survival; Chromatography, Liquid; Depsipeptides; Drug Screening Assays, Antitumor; Humans; Inhibitory Concentration 50; Terpenes

In this work, 64 samples of cereals purchased from local markets in the Valencian community (Spain) were investigated for the presence of six emerging mycotoxins: enniatins ENs (ENA, ENA1, ENB and ENB1), beauvericin (BEA) and fusaproliferin (FUS). Samples were extracted with a mixture of water/acetonitrile (85/15, v/v) by using an Ultra-turrax homogenizer. Mycotoxins were then identified and quantified with a liquid chromatography (LC) with diode array detector (DAD). Positive samples were confirmed with an LC-MS/MS. Analytical Results showed that the frequencies of contamination of samples with ENs, BEA and FUS were 73.4%, 32.8% and 7.8%, respectively. ENA1 was the most mycotoxin found and levels ranged from 33.38 to 814.42 mg/kg. ENB levels ranged between 2.23 and 21.37 mg/kg. ENB1 levels varied from 4.34 to 45.94 mg/kg. All samples were free of ENA. BEA levels ranged from 0.51 to 11.78 mg/kg and FUS levels varied between 1.01 and 6.63 mg/kg. It could be concluded from this study that the high contamination levels found especially for ENs could be of a negative impact on the population. This is the first paper on the presence of emerging mycotoxins in cereals available in Spain.

Topics: Chromatography, High Pressure Liquid; Depsipeptides; Edible Grain; Environmental Monitoring; Food Contamination; Food Microbiology; Fusarium; Mycotoxins; Spain; Terpenes

This paper describes the first map, albeit partial, of toxigenic fungi re-isolated from grape berries collected in three out of the six most important Slovakia winemaking areas in two different periods of the harvest year 2008. Low temperatures and high relative humidity during July 2008 favoured the development of grape fungal diseases that cause rots such as Plasmopara, Uncinula, Botrytis, Metasphaeria, Elsinoë, and Saccharomycetes. In the analysed samples, the following genera of toxigenic fungi were identified in the range of 1-4%: Aspergillus, Alternaria, Cladosporium, Epicoccum, Fusarium, Penicillium, Rhizopus, Ulocladium, and Trichoderma Trichothecium, while the genera Aspergillus, Alternaria, Fusarium, and Penicillium were in the range 11-29%. A. niger, A. carbonarius, some strains of A. carbonarius-with 'crystals' and strains of A. uvarum-uniseriate were identified; these species are considered ochratoxigenic (able to produce variable amounts of toxins). In addition, a non-ochratoxigenic strain of A. ibericus and a Fusarium strain able to biosynthesize small amount of fumonisins, beauvericin, and enniatins were identified. P. expansum, able to produce citrinin, represents 29.7%, of the Penicillium genus together with P. verrucosum, P. glabrum, P. citrinum, and P. crustosum. An analysis for the identification and quantification of the main toxins: ochratoxin A, fumonisins, beauvericin, enniatins, and fusaproliferin was performed on grape samples; it was consistent with the results of the mycological analysis. Toxigenic fungi should be checked throughout the years and their occurrence compared with all environmental factors to avoid health risks.

Topics: Chromatography, High Pressure Liquid; Citrinin; Depsipeptides; Food Contamination; Fruit; Fumonisins; Fungi; Limit of Detection; Microscopy, Electron, Scanning; Mycological Typing Techniques; Mycotoxins; Ochratoxins; Plant Diseases; Seasons; Slovakia; Species Specificity; Tandem Mass Spectrometry; Terpenes; Vitis; Weather; Wine

In a survey carried out on 87 rotted fig fruits samples collected in the Apulia region of Italy, the authors isolated 126 Fusarium strains identified as F. ramigenum (69 strains), F. solani (49), F. proliferatum (five) and three not identified. Investigation on the fertility of the strains belonging to F. proliferatum and F. ramigenum revealed that only strains of F. proliferatum were fertile. The identity of F. ramigenum strains was confirmed by sequencing a portion of the translation elongation factor-1alpha gene. When Fusarium species were analysed for their toxigenicity, 37/69 strains of F. ramigenum produced fusaric acid (FA) up to 525 mg kg(-1); 30 strains produced beauvericin (BEA) up to 190 mg kg(-1); 60 strains produced fumonisin B(1) (FB(1)) and fumonisin B(2) (FB(2)) up to 1575 mg kg(-1) of total FBs; and two strains produced fusaproliferin (FUP) up to 345 mg kg(-1); all five strains of F. proliferatum produced FA at low levels; two strains produced BEA up to 205 mg kg(-1); one strain produced FB(1) and FB(2), 1100 and 470 mg kg(-1), respectively; and one strain produced FUP, 820 mg kg(-1); F. solani (30 strains) produced FA, 13 strains up to 215 mg kg(-1). Few fungal extracts showed high toxicity toward brine shrimp larvae and in some cases in relation to BEA and FA content. A pathogenic assay on fig fruits showed that all three species were pathogenic, with higher virulence of F. ramigenum. These data report for the first time the production of BEA and FB(1)/FB(2) by F. ramigenum and show that it is a main agent of fig endosepsis in Apulia and can contribute to fumonisin contamination of fresh and dried figs.

Topics: Animals; Artemia; Biological Assay; Cell Extracts; Depsipeptides; Fertility; Ficus; Food Contamination; Fruit; Fungal Proteins; Fusaric Acid; Fusarium; Genes, Mating Type, Fungal; Italy; Mycological Typing Techniques; Mycotoxins; Peptide Elongation Factor 1; Phylogeny; Plant Diseases; Species Specificity; Terpenes; Virulence

The production of fumonisins, fusaproliferin and beauvericin by Gibberella fujikuroi different mating populations isolated from maize in Argentina was evaluated. From 203 strains of Fusarium verticillioides (G. fujikuroi mating population A), 193 were fumonisin producers. Among members of mating population A, female fertile strains produced 20% more toxin than female sterile ones. Among 78 Fusarium proliferatum strains (G. fujikuroi mating population D) 65 produced fumonisins. The percentage of strains that were high, intermediate and low level toxin producers varied according to the species evaluated and the area from which the strains were isolated. Fusarium subglutinans (G. fujikuroi mating population E) strains produced low levels or were no fumonisin producers. Strains from both G. fujikuroi mating populations D and E were able to produce fusaproliferin and beauvericin. Among the members of F. subglutinans (G. fujikuroi mating population E) the fusaproliferin production was more constant. Co-production of fumonisin, fusaproliferin and beauvericin among the strains belonging to G. fujikuroi D and E was also observed. The co-production of fumonisin, beauvericin and fusaproliferin in maize need to be considered, since from the toxicological point of view interactions between these toxins could occur. The toxigenic ability of the strains evaluated prompt us that is necessary to determine the natural occurrence of fusaproliferin and beauvericin in Argentinean maize.

Topics: Argentina; Crosses, Genetic; Depsipeptides; Fumonisins; Gibberella; Mycotoxins; Peptides; Phenotype; Terpenes; Zea mays

Fifteen Fusarium species were analyzed by high-performance liquid chromatography for the production of six mycotoxins in corn grits cultures. Production of mycotoxins ranged from 66 to 2,500 micro g/kg for fumonisin B(1), 0.6 to 1,500 micro g/g for moniliformin, 2.2 to 720 micro g/g for beauvericin, and 12 to 130 micro g/g for fusaproliferin. Fumonisin B(2) (360 micro g/kg) was produced by two species, fumonisin B(3) was not detected in any of the 15 species examined, and Fusarium bulbicola produced none of the six mycotoxins that we analyzed.

Topics: Anti-Bacterial Agents; Chromatography, High Pressure Liquid; Cyclobutanes; Depsipeptides; Fumonisins; Fusarium; Mycotoxins; Peptides; Terpenes; Zea mays

A rapid, sensitive and inexpensive HPLC method for routine screening of beauvericin, fusaproliferin, and enniatin B(1), A(1), and B has been optimized. Detection limits were determined, ranging between 0. 5 and 3.6 ng according to the compound obtained after spiking samples with each mycotoxin at 10-56 microg/mL concentration range; recoveries averaging from 56 to 74% were obtained. LC-MS conditions for enniatin analyses by API electrospray technique were set up, this allowing a unique identification of three different enniatins.

Topics: Anti-Bacterial Agents; Chromatography, High Pressure Liquid; Depsipeptides; Peptides; Sensitivity and Specificity; Terpenes

A method is described using LC-MS for the detection of the mycotoxins fusaproliferin (FUS) and beauvericin (BEA) in cultures of Fusarium subglutinans and in naturally contaminated maize. Protonated molecular ion signals for FUS and BEA were observed at m/z 445 and m/z 784, respectively. Collision induced dissociation of the readily dehydrated protonated molecular ion of the sesterterpene FUS (m/z 427) led to the loss of another water molecule (m/z 409) and acetic acid (m/z 385), while the cyclic lactone trimer BEA fragmented to yield the protonated dimer (m/z 523) and monomer (m/z 262), respectively. Detection of FUS was best performed in the MS-MS mode while BEA displayed a stronger signal in the MS mode. The on-column instrumental detection limits for pure FUS and BEA were found to be 2 ng and 20 pg (S/N=2) while those in naturally contaminated maize were 1 microg/kg and 0.5 microg/kg, respectively. Five South African strains of F. subglutinans were analyzed following methanol extraction of which four produced FUS at levels between 330 mg/kg and 2630 mg/kg while only three produced BEA at levels between 140 mg/kg and 700 mg/kg. Application of this method to naturally contaminated maize samples from the Transkei region of South Africa showed FUS at levels of 8.8-39.6 microg/kg and BEA at 7.6-238.8 microg/kg.

Topics: Anti-Bacterial Agents; Chromatography, High Pressure Liquid; Depsipeptides; Fusarium; Mass Spectrometry; Mycotoxins; Peptides; Sensitivity and Specificity; Terpenes; Zea mays

The production of fusaproliferin (FUS), a recently described mycotoxin, and beauvericin (BEA), a mycotoxin recently reported to co-occur with FUS in Fusarium-infected corn, by South African isolates in the Fusarium section Liseola, was investigated. Five isolates each of F. verticillioides, F. proliferatum, F. subglutinans, and F. globosum were cultured on corn kernels. Four each of the five South African isolates of F. proliferatum and F. subglutinans produced FUS (10-1725 and 330-2630 mg/kg, respectively). BEA was produced by four of the F. proliferatum strains (310-1130 mg/kg) and three of the F. subglutinans strains (140-700 mg/kg). The isolates of F. verticillioides failed to produce significant levels of either of these secondary metabolites. F. globosum was a weak producer of both in that one isolate of five produced 25 mg/kg FUS and five out of five produced BEA at levels ranging between 10 and 110 mg/kg. To further characterize these strains, their production of fumonisins B(1), B(2), and B(3), as well as moniliformin, was investigated. Of the four species investigated, fumonisins were produced by all except F. subglutinans, which in turn was the only species whose isolates in this study produced moniliformin (four of five isolates, ranging from 155 to 2095 mg/kg). Analysis of visibly Fusarium-infected home-grown corn collected in the Transkei region of the Eastern Cape Province of South Africa showed that nine of the ten samples contained low levels of FUS (up to 62 microg/kg), whereas all ten samples showed BEA contamination ranging from 8 to 1734 microg/kg with a mean of 258 microg/kg.

Topics: Anti-Bacterial Agents; Chromatography, Liquid; Cyclobutanes; Depsipeptides; Fusarium; Humans; Mass Spectrometry; Mycotoxins; Peptides; South Africa; Terpenes; Zea mays

One strain of Fusarium subglutinans (ITEM-1434) isolated from maize ear rot in Poland was tested for the ability to synthesize moniliformin (MON), beauvericin (BEA) and fusaproliferin (FP) on six cereal substrates (wheat, rye, barley, oat, maize and rice kernels) for 3 weeks at 25 degrees C and on rice at three different temperatures (20, 25 and 30 degrees C). Most MON (497 micrograms/g) was produced on rice; most BEA (704 micrograms/g) on wheat or rice, and most FP (422 micrograms/g) on rye. When cultured on rice, F. subglutinans produced the highest levels of BEA and FP at 20-25 degrees C, while MON production was best at 30 degrees C.

Topics: Anti-Bacterial Agents; Cyclobutanes; Depsipeptides; Edible Grain; Fermentation; Food Microbiology; Fusarium; Humans; Mycotoxins; Peptides; Temperature; Terpenes

Fusarium fungal contaminants and related mycotoxins were investigated in eight maize feed samples submitted to the Iowa State University Veterinary Diagnostic Laboratory. Fusarium moniliforme, F. proliferatum, and F. subglutinans were isolated from seven, eight, and five samples, respectively. These strains belonged to mating populations A, D, and E of the teleomorph Gibberella fujikuroi. Fusaproliferin was detected at concentrations of 0.1 to 30 microg/g in four samples, and beauvericin was detected (0.1 to 3.0 microg/g) in five samples. Fumonisins were detected in all eight samples (1.1 to 14 microg/g). Ten of 11 strains of F. proliferatum and all 12 strains of F. subglutinans isolated from the samples produced fusaproliferin in culture on whole maize kernels (4 to 350 and 100 to 1,000 microg/g, respectively). Nine F. proliferatum strains also produced beauvericin in culture (85 to 350 microg/g), but none of the F. subglutinans strains produced beauvericin. Fumonisin B1 was produced by all nine F. moniliforme strains (50 to 2,000 microg/g) and by 10 of the F. proliferatum strains (1,000 to 2,000 microg/g). This is the first report of the natural occurrence of fusaproliferin outside Italy and of the natural occurrence of beauvericin in North America.

Topics: Animal Feed; Anti-Bacterial Agents; Carboxylic Acids; Depsipeptides; Fumonisins; Fusarium; Gibberella; Iowa; Mycotoxins; Peptides; Terpenes; Zea mays

A new toxic sesterterpene, named fusaproliferin, was purified from corn kernel cultures (120 mg/kg dry culture) of a strain of Fusarium proliferatum isolated from corn ear rot in northern Italy. The stain, designated ITEM-1494, also produced fumonisin B1 (1.500 mg/kg dry culture) and beauvericin (90 mg/kg dry culture), but not moniliformin. To monitor toxicity, the brine shrimp assay was used throughout the isolation procedure. Fusaproliferin had a molecular formula of C27H40O5, and it is the first sesterterpene isolated from a Fusarium species.

Topics: Animals; Anti-Bacterial Agents; Artemia; Carcinogens, Environmental; Culture Media; Cyclobutanes; Depsipeptides; Fumonisins; Fusarium; Magnetic Resonance Spectroscopy; Mass Spectrometry; Mycotoxins; Peptides; Terpenes; Zea mays