Production of aflatoxin B1 and B2 by Aspergillus flavus in inoculated wheat using typical craft beer malting conditions

Schabo, Danieli Cristina; Martins, Luciano Moura; Maciel, Janeeyre Ferreira; Iamanaka, Beatriz Thie; Taniwaki, Marta Hiromi; Schaffner, Donald W.; Magnani, Marciane

doi:10.1016/j.fm.2020.103456

Cited by 19 publications

(17 citation statements)

References 48 publications

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“…The product was filtered and washed with cold methanol (2 × 25 mL), and the product was dried in a vacuum oven for 12 h at 35-40 °C to give 4-(chloromethyl)-5,7-dimethoxy-2H-chromen-2-one (39.2 g, 95.2% yield) as a white amorphous solid. 1 in ethanol (20 mL, four volumes) at RT. A solution of sodium hydroxide (1.058 g, 0.026 mol) in water (20 mL) was added in one lot at RT.…”

Section: Methodsmentioning

confidence: 99%

“…The product was washed with n-heptane (2 × 10 mL) and dried in a vacuum oven for 12 h at 40-45 °C to give 3-(5,7-dimethoxy-2-oxo-2H-chromen-4-yl)propanoic acid (3.15 g, 91.5% yield) as a pale yellow colored solid. 1 H NMR (400 MHz, CDCl 3 ): δ 2.68 (t, 2H, J = 7.6 Hz), δ 3.24 (t, 2H, J = 7.6 Hz), δ 3.86 (s, 3H), δ 3.89 (s, 3H), δ 6.03 (s, 1H), δ 6.33 (d, 1H, J = 2.0 Hz), δ 6.47 (d, 1H, J = 2.0 Hz), δ 11.52 (bs, 1H). 13 Literature method: typical procedure for the synthesis of 5,7-dimethylcyclopentenon [2,3c]…”

Section: Methodsmentioning

confidence: 99%

“…Pure 5,7-dimethylcyclopentenon[2,3-c]coumarin (1.40 g, 75% yield, HPLC purity: 99.5% (HPLC conditions: Column: Acquity UPLC ® BEH C18 1.7 μm 2.1 mm × 50 mm from Waters, Solvent: 1:1 (v/v) ratio of methanol and water amended with 0.1% formic acid, flow rate: 0.5 mL/ min, RT: 2.05 min)) was isolated as a white solid using flash chromatography eluting with 5% methanol:methylene chloride. 1 Improved method: synthesis of 5,7-dimethylcyclopentenon [2,3-c]…”

Section: Coumarin (Aft) Using a Lewis Acidmentioning

confidence: 99%

“…Aflatoxins belong to a large family of polyketide natural products known as mycotoxins due to their toxicity that originate from the secondary metabolites of a variety of ubiquitous fungal species. This particular group of toxins is produced by the molds Aspergillus flavus 1 and Aspergillus Parasiticus 2 that contaminate a variety of agricultural commodities and, when consumed by animals, can also transfer into edible animal by-products such as meat, milk, and milk by-products. The problems caused by aflatoxins are significant due to their high toxicity and carcinogenicity, aflatoxin B1 (AFB1) being classified as a group 1 carcinogen by the International Agency for Research on Cancer (IARC), and is tightly regulated in both food and feedstuffs.…”

Section: Introductionmentioning

confidence: 99%

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An efficient and metal-free synthesis of 5,7-dimethylcyclopentenon[2,3-c]coumarin

Yerramreddy

Yiannikouris

2021

Journal of Chemical Research

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An improved and alternative method for the metal-free synthesis of 5,7-dimethylcyclopentenon[2,3- c]coumarin as a possible useful aflatoxin template in the production of molecular imprinting polymers with affinity toward natural aflatoxin molecules is reported. A synthesis of 5,7-dimethylcyclopentenon[2,3- c]coumarin from 3,5-dimethoxyphenol via a Pechmann condensation involved five steps and represents an alternative commercially viable approach over existing synthetic protocols in the literature. Operational simplicity, inexpensive key raw materials, short reaction times, and excellent yields are remarkable features of this approach. The aflatoxin template was provided in 55%–67% overall yield from 3,5-dimethoxyphenol with >99% purity, evaluated by high-performance liquid chromatography, 1H NMR, 13C NMR, high-resolution mass spectrometry, and liquid chromatography–mass spectrometry.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Coumarin (Aft) Using a Lewis Acidmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

An efficient and metal-free synthesis of 5,7-dimethylcyclopentenon[2,3-c]coumarin

Yerramreddy

Yiannikouris

2021

Journal of Chemical Research

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“…Tropical and subtropical countries are more exposed to aflatoxicosis, because the level of food contamination with mycotoxins is not sufficiently monitored. Aflatoxins contribute to the contamination of maize, peanuts, wheat, barley, oilseeds, and spices, but also milk, dairy products, meat, and eggs as a consequence of mouldy feed consumed by livestock [21,23,60,61]. Aspergillus contamination can occur at pre-and post-harvest stages.…”

Section: Aflatoxinsmentioning

confidence: 99%

Molecular Aspects of Mycotoxins—A Serious Problem for Human Health

Janik

Niemcewicz

Ceremuga

et al. 2020

IJMS

121

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Mycotoxins are toxic fungal secondary metabolities formed by a variety of fungi (moulds) species. Hundreds of potentially toxic mycotoxins have been already identified and are considered a serious problem in agriculture, animal husbandry, and public health. A large number of food-related products and beverages are yearly contaminated by mycotoxins, resulting in economic welfare losses. Mycotoxin indoor environment contamination is a global problem especially in less technologically developed countries. There is an ongoing effort in prevention of mould growth in the field and decontamination of contaminated food and feed in order to protect human and animal health. It should be emphasized that the mycotoxins production by fungi (moulds) species is unavoidable and that they are more toxic than pesticides. Human and animals are exposed to mycotoxin via food, inhalation, or contact which can result in many building-related illnesses including kidney and neurological diseases and cancer. In this review, we described in detail the molecular aspects of main representatives of mycotoxins, which are serious problems for global health, such as aflatoxins, ochratoxin A, T-2 toxin, deoxynivalenol, patulin, and zearalenone.

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The presence and transfer characteristics of aflatoxins in medicinal herbs: From raw materials to edible dispensing granules

Wang

Zhang

et al. 2022

J of Separation Science

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In this study, a sensitive and accurate immunoaffinity columns coupled with high-performance liquid chromatography method was established to monitor the presence of aflatoxins-aflatoxin B 1 , aflatoxin B 2 , aflatoxin G 1 , and aflatoxin G 2 -in different medicinal herbs. The proposed method was found to be suitable for the detection of aflatoxins in eight kinds of herbs and their corresponding granules. Two batches of Arecae semen were positive for aflatoxins, with high residue levels of different aflatoxins. To better understand the presence and transfer of aflatoxins during the formulation of dispensing granules from the herbs, the aflatoxins-free herbs were artificially inoculated with Aspergillus flavus to explore aflatoxins production. Both aflatoxin B 1 and aflatoxin B 2 were detected in all inoculated samples, while aflatoxin G 2 was only detected in Astragali radix samples. Additionally, the presence of aflatoxin B 1 was extremely high compared to other aflatoxins. More specifically, the transfer rate of the aflatoxin B 1 and the total aflatoxins from original herbs to granules were both approximately 40%. These findings indicated that the preparation of herbs into dispensing granules reduced the content of aflatoxins. The high-level presence of aflatoxins in inoculated herbs indicated that attention is needed to the safety of A. flavus-contaminated herbs.

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Production of aflatoxin B1 and B2 by Aspergillus flavus in inoculated wheat using typical craft beer malting conditions

Cited by 19 publications

References 48 publications

An efficient and metal-free synthesis of 5,7-dimethylcyclopentenon[2,3-c]coumarin

An efficient and metal-free synthesis of 5,7-dimethylcyclopentenon[2,3-c]coumarin

Molecular Aspects of Mycotoxins—A Serious Problem for Human Health

The presence and transfer characteristics of aflatoxins in medicinal herbs: From raw materials to edible dispensing granules

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