title: Antifumonisin activity of natural phenolic compounds A structure-property-activity relationship study.
abstract: Fumonisin B(1) (FB(1)) is a Fusarium mycotoxin that has received considerable attention from food regulatory agencies, since it shows immunotoxic, neurotoxic, hepatotoxic, nephrotoxic and carcinogenic properties in animals. Although several publications have reported that some natural phenolic compounds can cause a reduction in mycotoxin production, little is known about the molecular properties related to their antitoxigenic activities. The objective of this work was to evaluate which of these molecular properties are important in antifumonisin activity, with this being the first structure-activity relationship study concerning the antimyctoxigenic activity of natural phenolic compounds. The results of the experimental determination of the FB(1) inhibition capacity for ten natural phenolic compounds revealed thymol, carvacrol, and isoeugenol followed by eugenol to be the most active antifumonisin compounds. Lipophilicity, molar refractivity and saturated area were demonstrated to be the molecular properties or descriptors which best explained the antifumonisin activity of these phenolic compounds. A mathematical expression, obtained by QSAR analysis, was able to predict the antifumonisin activity of other structurally related molecules. These findings could provide an important contribution in the search for new compounds with antifumonisin activity.
authors.affiliation: Instituto Multidisciplinario de Biología Vegetal-CONICET, Cátedra de Química Orgánica, FCEFyN-UNC, Avenida Vélez Sarsfield 1611, X5016GCA Córdoba. Argentina.
authors.forename: José S
authors.initials: JS
authors.lastname: Dambolena
authors.forename: Julio A
authors.initials: JA
authors.lastname: Zygadlo
authors.forename: Héctor R
authors.initials: HR
authors.lastname: Rubinstein
mesh_terms: D000081007:Cymenes; D005054:Eugenol / Q000031:analogs & derivatives / Q000494:pharmacology; D037341:Fumonisins / Q000378:metabolism*; D005670:Fusarium / Q000187:drug effects* / Q000378:metabolism; D008958:Models, Molecular; D015394:Molecular Structure; D039821:Monoterpenes / Q000494:pharmacology; D009183:Mycotoxins / Q000378:metabolism; D010636:Phenols / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D013943:Thymol / Q000494:pharmacology
chemical_list: D000081007:Cymenes; D037341:Fumonisins; D039821:Monoterpenes; D009183:Mycotoxins; D010636:Phenols; D013943:Thymol; D005054:Eugenol; C056933:fumonisin B1; C036643:isoeugenol; C073316:carvacrol