Collision‐induced dissociation of aflatoxins

Tóth, Katalin; Nagy, Lajos; Mándi, Attila; Kuki, Ákos; Mézes, Miklós; Zsuga, Miklós; Kéki, Sándor

doi:10.1002/rcm.6482

Cited by 7 publications

(3 citation statements)

References 22 publications

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“…Since the experimental adsorption process was carried out in acidic conditions, the first step of this research was to analyze the AFB 1 basic centers and their possible protonation structures (Figure 1). In this regard, others authors have reported the protonation of the AFB 1 molecule on the oxygen atom of the carbonylic groups (O 12 , O 14 ), furan ring (O 7 ), methoxyl group (O 13 ) and the lactone ring (O 10 ) [9,12,18], which is consistent with our findings. Additionally, a chemical structure with a hydrogen atom among the two carbonyl groups was considered (Figure 1A3,7).…”

Section: Study Of the Protonation Of Aflatoxin B 1 (Afb 1 )supporting

confidence: 93%

“…Both the furan and lactone rings are not stabilized by the protonation process, yielding the opening of the corresponding ring, as previously reported, using basic and acidic conditions [10,11,13]. In this regard, others authors have reported the protonation of the AFB1 molecule on the oxygen atom of the carbonylic groups (O12, O14), furan ring (O7), methoxyl group (O13) and the lactone ring (O10) [9,12,18], which is consistent with our findings. Additionally, a chemical structure with a hydrogen atom among the two carbonyl groups was considered (Figure 1A3,7).…”

Section: Study Of the Protonation Of Aflatoxin B 1 (Afb 1 )mentioning

confidence: 54%

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A Theoretical Study of the Adsorption Process of B-aflatoxins Using Pyracantha koidzumii (Hayata) Rehder Biomasses

Méndez‐Albores

Escobedo‐González

Aceves-Hernández

et al. 2020

Toxins

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Employing theoretical calculations with density functional theory (DFT) using the B3LYP/6-311++G(d,p) functional and basis set, the interaction of the aflatoxin B1 (AFB1) molecule and the functional groups present in the Pyracantha koidzumii biosorbent was investigated. Dissociation free energy and acidity equilibrium constant values were obtained theoretically both in solution (water) and gas phases. Additionally, the molecular electrostatic potential for the protonated molecules was calculated to verify the reactivity. Thus, methanol (hydroxyl group), methylammonium ion (amino group), acetate ion (carboxyl group), and acetone (carbonyl group), were used as representatives of the substrates present in the biomass; these references were considered using the corresponding protonated or unprotonated forms at a pH value of 5. The experimental infrared spectrophotometric data suggested the participation of these functional groups in the AFB1 biosorption process, indicating that the mechanism was dominated by electrostatic interactions between the charged functional groups and the positively charged AFB1 molecule. The theoretical determination indicated that the carboxylate ion provided the highest interaction energy with the AFB1 molecule. Consequently, an enriched biosorbent with compounds containing carboxyl groups could improve the yield of the AFB1 adsorption when using in vitro and in vivo trials.

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Section: Study Of the Protonation Of Aflatoxin B 1 (Afb 1 )supporting

confidence: 93%

Section: Study Of the Protonation Of Aflatoxin B 1 (Afb 1 )mentioning

confidence: 54%

A Theoretical Study of the Adsorption Process of B-aflatoxins Using Pyracantha koidzumii (Hayata) Rehder Biomasses

Méndez‐Albores

Escobedo‐González

Aceves-Hernández

et al. 2020

Toxins

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“…Due to limited use of LC-TOF in mycotoxin research, very few studies use LC-TOF or LC-Q-TOF for aflatoxin analysis. Toth et al [289] used a LC-Q-TOF and studied fragmentation patterns of aflatoxins under different collision energies. No quantitative analysis was performed.…”

Section: Lc-ms For Quantitative Analysismentioning

confidence: 99%

A Review: Sample Preparation and Chromatographic Technologies for Detection of Aflatoxins in Foods

Zhang

Banerjee

2020

Toxins

102

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As a class of mycotoxins with regulatory and public health significance, aflatoxins (e.g., aflatoxin B1, B2, G1 and G2) have attracted unparalleled attention from government, academia and industry due to their chronic and acute toxicity. Aflatoxins are secondary metabolites of various Aspergillus species, which are ubiquitous in the environment and can grow on a variety of crops whereby accumulation is impacted by climate influences. Consumption of foods and feeds contaminated by aflatoxins are hazardous to human and animal health, hence the detection and quantification of aflatoxins in foods and feeds is a priority from the viewpoint of food safety. Since the first purification and identification of aflatoxins from feeds in the 1960s, there have been continuous efforts to develop sensitive and rapid methods for the determination of aflatoxins. This review aims to provide a comprehensive overview on advances in aflatoxins analysis and highlights the importance of sample pretreatments, homogenization and various cleanup strategies used in the determination of aflatoxins. The use of liquid-liquid extraction (LLE), supercritical fluid extraction (SFE), solid phase extraction (SPE) and immunoaffinity column clean-up (IAC) and dilute and shoot for enhancing extraction efficiency and clean-up are discussed. Furthermore, the analytical techniques such as gas chromatography (GC), liquid chromatography (LC), mass spectrometry (MS), capillary electrophoresis (CE) and thin-layer chromatography (TLC) are compared in terms of identification, quantitation and throughput. Lastly, with the emergence of new techniques, the review culminates with prospects of promising technologies for aflatoxin analysis in the foreseeable future.

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A Fragmentation Study on Four Unusual Secoiridoid Trimers, Swerilactones H–K, by Electrospray Tandem Mass Spectrometry

Geng

Chen

2016

Nat. Prod. Bioprospect.

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Swerilactones H–K (1–4) as four unprecedented secoiridoid trimers represent a new type of natural product, which has attracted much interest of natural chemists due to their novel skeletons and promising bioactivity. In order to well understand their MS fragmentation behaviors, they were investigated by electrospray ionization ion-trap time-of-flight multistage product ion mass spectrometry (ESI-IT-TOF-MSn) for the first time. The protonated molecules ([M+H]+) of swerilactones J and K, and deprotonated molecules ([M−H]−) of swerilactones H, J and K were readily observed in the conventional single-stage mass spectra (MS); however only the [M+Cl]− ion for swerilactone I was obtained in negative mode. Based on the MSn study, the fragmentation pathways of swerilactones H and I in negative mode, and swerilactones J and K in both positive and negative modes were proposed. The neutral losses of H2O, CO, CO2 and C2H4O moieties are the particular elimination from the precursor ions due to the presence of hydroxyl, δ-lactone and 1-O-ethyl moieties in their structures, of which the retro-Diels–Alder cleavage was the most particular dissociation. The fragment ions at m/z 341 and 291 in negative mode can be considered as the diagnostic ions for secoiridoid trimers. This investigation will provide valuable information for their fast characterization from complicated natural mixtures and extensive understanding their structural architectures.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0114-6) contains supplementary material, which is available to authorized users.

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Collision‐induced dissociation of aflatoxins

Cited by 7 publications

References 22 publications

A Theoretical Study of the Adsorption Process of B-aflatoxins Using Pyracantha koidzumii (Hayata) Rehder Biomasses

A Theoretical Study of the Adsorption Process of B-aflatoxins Using Pyracantha koidzumii (Hayata) Rehder Biomasses

A Review: Sample Preparation and Chromatographic Technologies for Detection of Aflatoxins in Foods

A Fragmentation Study on Four Unusual Secoiridoid Trimers, Swerilactones H–K, by Electrospray Tandem Mass Spectrometry

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