2-2--azino-di-(3-ethylbenzothiazoline)-6-sulfonic-acid and 4-hydroxybenzoic-acid

Methanol extract subfractions of the edible white jelly mushroom (Tremella fuciformis), were assessed for the following antioxidant properties: ABTS(+) radical scavenging activity, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity, and inhibitory activity of human low-density lipoprotein (LDL) oxidation. Among the subfractions tested, the chloroform subfraction exhibited the strongest antioxidant activity, with the highest total phenolic content (66.31 μg CAE/mg extract) and flavonoids content (5.12 μg QE/mg extract). The ABTS(+) radical scavenging activity of the chloroform subfraction was 7.89 μmol trolox/mg extract, which was the highest among all subfractions. This subfraction also showed the highest DPPH radical scavenging activity and inhibitory activity of LDL oxidation. In addition, the chloroform subfraction demonstrated anti-inflammatory activity through inhibition of nitric oxide production and inducible nitric oxide synthase expression in RAW 264.7 cells. Major phenolic acids from the mushroom extract were identified as 4-hydroxybenzoic acid (323 mg/kg dry weight of mushroom), gentisic acid (174 mg/kg dry weight of mushroom), and 4-coumaric acid (30 mg/kg dry weight of mushroom).

Topics: Agaricales; Anti-Inflammatory Agents; Antioxidants; Basidiomycota; Benzothiazoles; Biological Products; Biphenyl Compounds; Cell Line; Coumaric Acids; Flavonoids; Gentisates; Humans; Inflammation; Lipoproteins, LDL; Nitric Oxide; Nitric Oxide Synthase Type II; Parabens; Phenols; Picrates; Propionates; Sulfonic Acids

The influence of pH, intrinsic electron donating capacity, and intrinsic hydrogen atom donating capacity on the antioxidant potential of series of hydroxy and fluorine substituted 4-hydroxybenzoates was investigated experimentally and also on the basis of computer calculations. The pH-dependent behavior of the compounds in the TEAC assay revealed different antioxidant behavior of the nondissociated monoanionic form and the deprotonated dianionic form of the 4-hydroxybenzoates. Upon deprotonation the radical scavenging ability of the 4-hydroxybenzoates increases significantly. For mechanistic comparison a series of fluorobenzoates was synthesized and included in the studies. The fluorine substituents were shown to affect the proton and electron donating abilities of 4-hydroxybenzoate in the same way as hydroxyl substituents. In contrast, the fluorine substituents influenced the TEAC value and the hydrogen atom donating capacity of 4-hydroxybenzoate in a way different from the hydroxyl moieties. Comparison of these experimental data to computer-calculated characteristics indicates that the antioxidant behavior of the monoanionic forms of the 4-hydroxybenzoates is not determined by the tendency of the molecule to donate an electron, but by its ability to donate a hydrogen atom. Altogether, the results explain qualitatively and quantitatively how the number and position of OH moieties affect the antioxidant behavior of 4-hydroxybenzoates.

Topics: Antioxidants; Benzothiazoles; Chromans; Electrons; Fluorine; Free Radical Scavengers; Hydrogen; Hydrogen Bonding; Hydrogen-Ion Concentration; Hydroxylation; Indicators and Reagents; Parabens; Sulfonic Acids