Chromatographic and spectroscopic properties of hemiacetals of aflatoxin and sterigmatocystin metabolites

Orti, Donna L.; Grainger, James; Ashley, David L.; Hill, Robert H.

doi:10.1016/s0021-9673(00)91353-0

Cited by 20 publications

(7 citation statements)

References 14 publications

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“…The UV spectra of the AFB 2a standard and the extracted analyte both have an absorbance maximum at 363 nm, while the maximum absorbance of the AFM 2 spectrum is at 357 nm. These results are consistent with previously published UV spectra for both AFB 2a and AFM 2 (Orti et al 1989;Cole and Cox 1981). Thus, based on retention time and absorption spectrum, the species eluting at 12.8 min was identified as AFB 2a .…”

Section: Resultssupporting

confidence: 92%

“…Hutchins and Hagler (1983) showed that at lower pH, the conversion of AFB 1 to AFB 2a went to completion at room temperature. Additionally, the acidic hydration of AFM 1 , AFP 1 , and AFQ 1 to form their corresponding hemiacetals has also been reported (Orti et al 1989;Megalla and Hafez 1982). Megalla and Hafez (1982) were able to convert AFB 1 to AFB 2a using a 2% lactic acid solution and acidogenous yogurt.…”

Section: Transformation Of Afb 1 In An Aqueous Soil Matrixmentioning

confidence: 87%

“…Megalla and Hafez (1982) were able to convert AFB 1 to AFB 2a using a 2% lactic acid solution and acidogenous yogurt. Finally, Orti et al (1989) showed that the hemiacetal could be synthesized from any parent aflatoxin compound by the addition of water across the vinyl ether double bond in an acidic solution.…”

Section: Transformation Of Afb 1 In An Aqueous Soil Matrixmentioning

confidence: 99%

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Solvent-dependent transformation of aflatoxin B1 in soil

2017

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To date, all studies of aflatoxin B (AFB) transformation in soil or in purified mineral systems have identified aflatoxins B (AFB) and G (AFG) as the primary transformation products. However, identification in these studies was made using thin layer chromatography which has relatively low resolution, and these studies did not identify a viable mechanism by which such transformations would occur. Further, the use of methanol as the solvent delivery vehicle in these studies may have contributed to formation of artifactual transformation products. In this study, we investigated the role of the solvent vehicle in the transformation of AFB in soil. To do this, we spiked soils with AFB dissolved in water (93:7, water/methanol) or methanol and used HPLC-UV and HPLC-MS to identify the transformation products. Contrasting previous published reports, we did not detect AFB or AFG. In an aqueous-soil environment, we identified aflatoxin B (AFB) as the single major transformation product. We propose that AFB is formed from hydrolysis of AFB with the soil acting as an acid catalyst. Alternatively, when methanol was used, we identified methoxy aflatoxin species likely formed via acid-catalyzed addition of methanol to AFB. These results suggest that where soil moisture is adequate, AFB is hydrolyzed to AFB and that reactive organic solvents should be avoided when replicating natural conditions to study the fate of AFB in soil.

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Section: Resultssupporting

confidence: 92%

Section: Transformation Of Afb 1 In An Aqueous Soil Matrixmentioning

confidence: 87%

Section: Transformation Of Afb 1 In An Aqueous Soil Matrixmentioning

confidence: 99%

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Solvent-dependent transformation of aflatoxin B1 in soil

2017

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“…The use of pre-column TFA derivatization has been reported for their determination, 10,11 as well as halogenation using bromine 12,13 or iodine, 14 in order to improve the fluorimetric detection. Nevertheless a major common drawback of these procedures is the instability of the derivatives and the fact that the use of bromine with AFP 1 produces a damping of the native fluorescence of the compound.…”

Section: Introductionmentioning

confidence: 99%

Preliminary study on fluorimetric detection of aflatoxins Q1, P1 and B1 using heptakis-di-O-methyl-β-cyclodextrin as post-column HPLC reagent

Vázquez¹,

Fente²,

Franco³

et al. 1999

Anal. Commun.

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“…Ένζυμα ό πως ÖL οξειδάσες, το κυτόχρωμα Ρ-450, η φλαβοπρω-τεΐνη, η αναγωγάση του κυτοχρώματος Ρ-450, παίρ νουν μέρος στο μεταβολισμό των αφλατοξινών. OL ο ξειδάσες των κυτοχρωμάτων οξειδώνουν τη AFB 1 και παράγονται μεταβολίτες, όπως η AFQ 1 (αφλατοξίνη Qi), η AFM 1 και η AFB 2 , οι οποίες είναι υδατοδιαλυ-τές και αποβάλλονται πιο εύκολα από τον οργανισμό (Masri et al 1974, Orti et al 1989. Επίσης, η AFB 1 με την επίδραση των ενζύμων του κυτοχρώματος Ρ-450 μεταβολίζεται σε 8, 9 εποξείδιο της AFB b το οποίο μπορεί να ενωθεί με τη γουανίνη του DNA, με αποτέ λεσμα την αρχή της καρκινογένεσης, ή με πρωτεΐνες, όπως οι αλβουμίνες (Montesano et al 1997, Wild andTuner 2002).…”

Section: τοξικότητα των αφλατοξινώνunclassified

Aflatoxins in foods of animal origin

Govaris

2017

J Hellenic Vet Med Soc

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Anatoxins are produced by various types of Aspergillus spp. fungi in a wide variety of foods and feeds. Anatoxins are toxic to human and animals, acute and chronic. In humans, they can cause liver cancer, chronic hepatitis and cirrhosis. Among the four main aflatoxins (B1? B2, Gx and G2), aflatoxin Βχ (AFBi) is the most frequently found in feeds and the most toxic one. The most important aflatoxin in foods of animal origin is aflatoxin M4 (AFM4), which is the principal hydroxylated metabolite of AFB! AFM4 is mainly found in milk from lactating animals consuming feed contaminated with AFB^ Surveys carried on the occurrence of AFM4 in raw milk in various countries all over the world during the past 15 years, showed that contamination levels were low in European Union and USA, but high in certain countries of Africa, Asia and Latin America. Other global surveys on the occurrence of AFM4 in foods of animal origin (meat, eggs etch) showed that the level of the toxin is low as compared to milk and dairy products. European Union has set the maximum residual limit (MRL) for AFM4 of 0.05 μg/kg and 0.025 μg/kg in raw milk and milk powder for infants, respectively. In order to protect the consumer's health, control measures should be applied to avoid contamination of feed and foods with aflatoxins.

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Chromatographic and spectroscopic properties of hemiacetals of aflatoxin and sterigmatocystin metabolites

Cited by 20 publications

References 14 publications

Solvent-dependent transformation of aflatoxin B1 in soil

Solvent-dependent transformation of aflatoxin B1 in soil

Preliminary study on fluorimetric detection of aflatoxins Q1, P1 and B1 using heptakis-di-O-methyl-β-cyclodextrin as post-column HPLC reagent

Aflatoxins in foods of animal origin

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