Azadeh Mardani Ghahfarokhi; Reza Farhoosh; Ali Sharif
Abstract
Introduction: Hydroxybenzoic acids are a large family of phenolic acids capable of inhibiting one of the most destructive reactions called lipid oxidation. Their antioxidant activities are markedly influenced by the number and position of phenolic OH groups. Increasing the number of electron-donating ...
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Introduction: Hydroxybenzoic acids are a large family of phenolic acids capable of inhibiting one of the most destructive reactions called lipid oxidation. Their antioxidant activities are markedly influenced by the number and position of phenolic OH groups. Increasing the number of electron-donating groups in the molecule and their placement at the ortho and/or para positions of the phenolic ring, could lead to the increased ability of H atom abstraction or electron donating capacity. Gentisic (3,5-dihydroxybenzoic acid) and Alpha-resoecylic (2,5-dihydroxybenzoic acid) acids are dihydroxybenzoic acids wildly dispersed in the plant tissues with some valuable biological and pharmacological properties for human health. These compounds are different in structure and position of hydroxyl groups in phenolic ring, that may had a strong influence on their antioxidant properties. In addition of structural property, environmental interference can play an important role in the antioxidant potency. Antioxidants are found to behave differently when used in different media.
Materials and methods: Partition coefficient (log P) of Gentisic acid and Alpha-resorcylic acid was measured between 1-octanol and acetate buffers. Antiradical and antioxidant activity of compounds was investigated in different medium (solvent system, purified bulk olive and soybean oils and their O/W emulsions). DPPH radical scavenging activity of gentisic acid and alpha-resorcylic acid was measured in the methanolic solvent. Progress of lipid oxidation in olive oil and soybean oil containing 200 ppm of the antioxidants at 80 oC was followed by monitoring the changes in peroxide value (PV). PV was measured spectrophotometrically at 500 nm using a UV– Vis instrument. Oxygen depletion in emulsion systems in the absence and present of the antioxidant (200 ppm) was measured using a YSI Model 5300A biological oxygen monitor at 37oC. The effectiveness of the antioxidants in bulk oils and emulsions was estimated on the basis of the induction period (IP).
Results and discussion: The obtained results indicated that the effectiveness of the Gentisic and - resorcylic acids in free radicals scavenging, was greatly affected by molecular structure of these antioxidants and environmental conditions.
Ortho position of hydroxyl group with respect to the carboxyl group in Gentisic acid, caused higher antiradical potency of Gentisic acid than α-resorcylic acid, with meta-structure, in different used mediums.
In addition, it was found that the environment plays an important role in the free radical scavenging activity of phenolic compounds. Gentisic acid with more hydrophilic structure showed better antioxidant activity in bulk oil hydrophobic systems, than emulsion systems, while -resorcylic acid with less hydrophilic structure showed better activity in O/W emulsions. Both antioxidants showed low antioxidant performance in solvent system. The polar medium of the methanol used in DPPH assay, with enhanced intermolecular hydrogen bonds, decreased the radical scavenging potency of antioxidants.
