Abstract
Ochratoxin A (OTA) is a mycotoxin whose dangers have been sufficient for many countries to regulate its presence in various foods. In Mediterranean countries, the black Aspergilli group, in particular Aspergillus carbonarius causes the highest OTA contamination in fruit.
Here, we describe the synthesis of three novel styryl heterocyclic compounds and their effect on (1) the prevention of OTA biosynthesis by A. carbonarius cultured in a conducive liquid medium, (2) Reactive Oxygen Species (ROS) formation, and (3) lipoxygenase (LOX) activity.
The most effective control of OTA biosynthesis was achieved with (E)-3-(3,4-dimethoxy-styryl)-thiophene. In fungal cultures treated with this compound at 5, 25, 50, and 100 ppm, OTA biosynthesis decreased by 45% to 95% until the experiment's conclusion (8 days).
(E)-3-(3-methoxy-4-acetoxy-styryl)-thiophene significantly inhibited OTA biosynthesis (about 50%). However, this effect lasted for only few days when used at 5 or 25 ppm and up to 8 days when used at 50 or 100 ppm; (E)-3-(3-methoxy-4-hydroxy-styryl)-thiophene did not exert any control on OTA biosynthesis.
The same compounds also were assayed for their ability to affect LOX activity and ROS formation. The compounds able to control OTA biosynthesis also significantly inhibited ROS formation and LOX activity. The nature of the substituent in para position strongly affects the molecule’s reactivity. Lower reactivity enhances the inhibition of OTA biosynthesis, in particular long-term. Natural compounds present in edible plants having a styryl heterocyclic scaffold may be effective inhibitors of OTA biosynthesis.
Keywords: Styryl heterocycles, styryl-3-thiophene, ochratoxin A, lipoxygenase, Reactive Oxygen Species, peroxides.
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Books
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advances in Organic Synthesis
28
1
1
1