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Role of Some Food-Grade Synthesized Flavonoids on the Control of Ochratoxin A in Aspergillus carbonarius

1
Institute of Molecular Biology and Pathology-CNR P.le Aldo Moro 5, 00185 Rome, Italy
2
Department of Chemistry, Sapienza University, P.le A Moro 5, I-00185 Rome, Italy
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(14), 2553; https://doi.org/10.3390/molecules24142553
Received: 6 June 2019 / Revised: 5 July 2019 / Accepted: 11 July 2019 / Published: 13 July 2019
(This article belongs to the Special Issue Mycotoxins)
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Abstract

Ochratoxin A (OTA) is a mycotoxin with a serious impact on human health. In Mediterranean countries, the black Aspergilli group, in particular Aspergillus carbonarius, causes the highest OTA contamination. Here we describe the synthesis of three polyphenolic flavonoids: 5-hydroxy-6,7-dimethoxy-flavone (MOS), 5,6-dihydroxy-7-methoxy-flavone (NEG), and 5,6 dihydroxy-flavone (DHF), as well as their effect on the prevention of OTA biosynthesis and lipoxygenase (LOX) activity in A. carbonarius cultured in a conducive liquid medium. The best control effect on OTA biosynthesis was achieved using NEG and DHF. In fungal cultures treated with these compounds at 5, 25, and 50 μg/mL, OTA biosynthesis significantly decreased throughout the 8-day experiment. NEG and DHF appear to have an inhibiting effect also on the activity of LOX, whereas MOS, which did not significantly inhibit OTA production, had no effect on LOX activity. The presence of free hydroxyls in catecholic position in the molecule appears to be a determining factor for significantly inhibiting OTA biosynthesis. However, the presence of a methoxy group in C-7 in NEG could slightly lower the molecule’s reactivity increasing OTA inhibition by this molecule at 5 μg/mL. Polyphenolic flavonoids present in edible plants may be easily synthesized and used to control OTA biosynthesis. View Full-Text
Keywords: flavones; aromatic hydroxylation; Aspergillus carbonarius; ochratoxin A; lipoxygenase flavones; aromatic hydroxylation; Aspergillus carbonarius; ochratoxin A; lipoxygenase
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Ricelli, A.; De Angelis, M.; Primitivo, L.; Righi, G.; Sappino, C.; Antonioletti, R. Role of Some Food-Grade Synthesized Flavonoids on the Control of Ochratoxin A in Aspergillus carbonarius. Molecules 2019, 24, 2553.

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